Over the past month I’ve been claudepilled hard and have become a power user of claude code in vscode . . . but not to work on software development.

I’m the marketing/business cofounder of a multi 7-figure, bootstrapped SaaS company. Others have used these new AI skills to move more into product/dev, but that isn’t me. I still am not touching product at all. 100% of my claude code work is marketing or running-the-business stuff like financial projections.

So I thought it would be fun to ask claude everything we accomplished in the past week. Here’s what claude provided:

15 YouTube videos produced and published

This was the big one. We went from zero video capability to a full repeatable pipeline in a week.

The pipeline we built:

• Blog post or workshop recording goes in
• AI writes a narration script optimized for YouTube retention and Google search
• ElevenLabs generates the voiceover
• Claude writes a Python renderer that creates animated slide videos synced to the audio (word-level timing via Whisper)
• Claude generates the title, SEO description, tags, thumbnail, and pinned comment
• A bulk upload script pushes everything to YouTube with thumbnails and playlists

What actually shipped:

• 14 short educational clips extracted from two workshop recordings, each turned into animated slide videos with Whisper-synced text
• 1 blog-to-video conversion (full 8-minute narration from a blog post, TTS audio, 20-slide animated video)
• All 15 uploaded to YouTube with SEO-optimized metadata and custom thumbnails

The slide video skill went through massive iteration — started with 4–8 sparse slides that sat static for 30–40 seconds, ended with 15–20 dense slides with something new appearing every 3–5 seconds. Every animation delay is derived from Whisper’s word-level timestamps, not guesswork.

Google Ads campaign rebuilt from scratch

Analyzed thousands of search terms to find what was actually converting vs. burning money. Built 15 new ad groups with targeted keywords, wrote all the ad copy, created 150+ negative keywords to stop waste, and executed the whole thing through Google Ads Scripts (automated, not manual clicking).

Also wrote an automated “Negative Keyword Catcher” script that runs on a schedule to find and block bad search terms before they waste money.

Pinterest strategy from zero

Audited the existing Pinterest account, identified 5 problems (no visual consistency, heavy repinning hurting reach, zero video pins, missing our best keyword clusters, descriptions that weren’t SEO-optimized).

Built a full strategy doc, then executed:

• Left/archived group boards that were diluting account quality
• Renamed boards to keyword-targeted names with SEO descriptions
• Created 5 new boards targeting high-value search terms
• Rewrote the profile bio for search
• Configured Tailwind scheduling (35 pins/week, automated)

Next phase: AI-generated pin templates so we can turn every blog post into 3–5 unique pin designs automatically.

Ad creative and strategy

• Designed 12 retargeting ad images (testimonial-based, 4 sizes each for different placements)
• Generated 9 ad creatives across 3 different visual formats
• Developed a new emotional angle for our lead magnet ads (imposter syndrome framing vs. the existing rational/data angle)
• Overhauled our creative testing methodology — changed from too many small-budget tests that never exit learning phase to fewer, properly-funded tests that give a clear read in 7–10 days
• Built lookalike audiences from CRM data

Cross-platform ad analytics infrastructure

• Created weekly deep-dive skills for each ad platform (Meta, Google, LinkedIn) so analysis is consistent and repeatable
• Built benchmark docs with platform-specific CPL ranges, conversion rates by time horizon, and spend ceilings
• Modeled maximum ad spend ceiling from P&L data and built a phased scale-up plan
• Fixed a bunch of spreadsheet formulas that were silently returning wrong numbers (wrong column references, data connector in append mode duplicating rows, missing ad set IDs in formulas)

LinkedIn tracking fix confirmed

We’d identified a bug where ~34% of paid LinkedIn leads were misattributing due to hardcoded UTMs in our link shortener overriding LinkedIn’s dynamic tracking. After fixing the links, verified that 100% of new leads are now tracking correctly.

Instagram carousel automation

Built an n8n workflow that scouts trending Instagram carousel formats, adapts them to our niche, generates slide copy and images, and posts a draft to Slack for review. Also manually built a second carousel in Canva via the API.

Infrastructure

• Built a Google Docs reader (so Claude can pull content from our Google Docs directly)
• Set up Google Ads API access for future automation
• Added a mandatory self-review system — Claude now runs through a checklist before declaring any code “done” (this fixed a pattern where it would write code, say it was finished, then I’d find bugs on review)
• Cleaned up and compressed the instruction files that load every session — cut context by 48% with zero information lost

How this actually works

[ Claude had the idea to add the section below, and it answers a question I get asked a lot so I’m including it . . take it away claude! ]

Claude Code runs in my terminal. It has access to my file system, APIs (Google Sheets, ActiveCampaign, Slack, YouTube, ElevenLabs, Canva), and can write and execute code. I describe what I want, it figures out how to do it.

The “skills” are reusable instruction files that capture what we’ve learned. When I say /slide-video, Claude loads a detailed skill doc that tells it exactly how to plan slides, sync timing to audio, render frames, and verify the output. These skills accumulate — each session's lessons get folded back in so the same mistakes don't repeat.

The key insight: most of this isn’t “AI doing my job.” It’s AI handling the production work (rendering videos, writing upload scripts, formatting spreadsheet formulas, generating image variations) so I can focus on strategy decisions (which angles to test, where to allocate budget, what content to produce).

If you haven’t read part one of how we built a 7-figure company with zero meetings, start here.

Let’s be honest, most people hate meetings. They’re viewed as a “necessary evil” that suck up a huge amount of the team’s time. And they quickly spiral out of control so quickly that you’re forced to squeeze in pockets of time to actually work!

But this raises the obvious question: Without meetings, how does anyone know what’s happening?

The Team Behind the No-Meeting Experiment

You’re probably wondering: are we doing this with three people or three hundred? At the time of writing, our core team consists of 9 part-time people:

• 2 full stack developers (1 is a founder)
• 1 product designer
• 3 customer service people
• 1 marketing/business operations (founder, me)
• 1 person who oversees SEO (link building, writing articles, updating article, etc)
• 1 general marketing support

No one is full-on full time, and people are varying degrees of part-time. Most work 10–20 hours per week.

Most people have their own business or other clients, but not everyone does. In the past I had the belief that you only got people’s best work if they worked only for you. I now have proof this isn’t true. Actually, I think having other clients often means even better work from our team.

We also have more regular and irregular freelancers we work with — for example, our bookkeeper and the writers who write our blog posts.

We don’t have anyone in a typical management role. We also don’t have anyone junior. I don’t think our style of running the business would work with junior people that need a lot of training and feedback — because we don’t give a lot of training or feedback! 😅

Now, let’s dive into how we actually stay coordinated without a single meeting.

How Do People Know What’s Going on Without Meetings?

Internal Work In Public

The first and most important way that people keep abreast of what’s happening is a kind of internal work-in-public. I used to think this was a given for all remote companies, until I kept meet humans who proved me wrong. Shout-out to that guy who ran his entire company on a hodge-podge of random whatsapp groups and messages! (As you can guess, we were discussing it because it wasn’t working super well.)

Our work happens in github for anything product, and clickup for everything else.

BTW I don’t think there’s anything special about these tools, and our product team doesn’t particularly even love github that’s just where other work was happening already so it just made sense to centralise everything there. ClickUp has some cool automation features, and we store our documentation there. But honestly, it doesn’t matter whether you use Monday, Basecamp, Asana, or any other tool.

The important part is having work visible to everyone. What is everyone else on the team doing? Look at the clickup boards, or search their name, or just have a poke through clickup.

Note that for this to work your system has to be full of ACTUAL work, not a bunch of abandoned tasks. I’ve seen companies whose task management systems are full of theoretical work that never gets done, while people actually work in Slack DMs and emails. We are not the same.

(I go in detail on my personal clickup/weekly planning process in this post.)

Slack Based Stand-Ups

Many people on the team also post what they’ve done each day in slack.

Here’s an example:

These kinds of ‘stand-ups,’ at the start or end of the day, are essential for remote teams. Not only do they give an update on what’s happening, but they’re an easy check to make sure someone doesn’t ghost for weeks before someone notices!

Working remotely with no evidence doesn’t work. Full stop.

One of the most common questions/complaints I get from founders about their remote team is “they just disappear and I have no idea what’s going on”. That’s why daily visibility is so important.

Our CS team posts an update in slack every day they work that often just says “emails”. It looks like this:

One big reason for this is so that, as a founder, I know the inbox is being tended to every day. If I didn’t get this update, a week could go by with nothing being answered in Help Scout, and I would have no idea. So this is something that takes 5 seconds from the team and lets me and everyone else know that things are churning along.

Weekly Summary

I post a summary of what happened the week before in slack each Monday. Here’s a snippet from a recent week (there is also a product section, and I usually include a nice thing a customer has said about us recently)

I pull the weekly update together using my clickup ‘Completed’ board and by going through Slack for the previous week. It usually takes me about 20 minutes and gives me a chance to make sure nothing has slipped through the cracks.

Public Slack Data Feeds

Here’s some of the data that we feed into slack:

• Every new customer
• Every helpscout rating
• Every cancellation and reason
• Every deploy

This kind of public data helps both personal accountability (if you get a bad rating it’s on display for everyone to see!) as well as another source the team can check to get a feel for what’s going on.

Note that no one is expected to read everything in slack, and we still follow the “calm slack” principles I laid out in this article.

In next week’s article, I’ll explain how we handle work assignments and decision-making without managers or meetings. If you have specific questions you’d like me to address, drop them in the comments!

My company Paperbell was launched in spring 2020 (aww pandemic baby!) which makes 2025 our 5 year anniversary.

It also means I’m five years into this crazy experiment of working completely a-sync with no meetings, no managers, no 1:1s and a lot of other unorthodox ways of working.

Has it been a success? For me, the answer is a huge yes. Last year we crossed the million dollar ARR mark, the business is growing and profitable, and I love this style of work. (The rest of the team loves it too!)

But of course, it has its pros and cons.

So let’s dive into how in the world we’ve operated with no meetings for five years, and why.

Why I Went From Real-Time Remote to Completely Asynchronous

My last company, MeetEdgar, was always remote. But we did “real-time remote”. We were all in the US and we had regular live meetings. We had a weekly company wide all-hands, weekly team meetings, weekly leadership team meeting, lots of 1:1s, and team daily standups. All of this was done live on zoom.

Basically, we operated like a “regular” offline company but moved the work online.

Then, I heard a conversation with Matt Mullenweg and Sam Harris about the five different levels of remote work. Wordpress is one of the oldest all-remote companies out there, and Matt laid the idea out in a blog post here.

One idea from the podcast struck me like a lightning bolt: by trying to replicate traditional office structure in remote work, we’re missing the point entirely.

Remote work offers new and different benefits that in-person doesn’t, like new levels of autonomy and efficiency. Trying to recreate an in-person office online focuses on the drawbacks of remote work instead of embracing the benefits.

I started to understand some of my frustrations with the ways we had set up my “real time remote” company. We tried to make sure the team had trust and bonding, but it always felt really forced and awkward online. And no matter how hard to tried to make our meetings short and relevant, we still seemed to spend an awful lot of time in unnecessary meetings instead of just getting on with our work.

In an in-person office you have lunch and coffee with you coworkers every day, you chat with them and learn about their lives. This is natural and it’s great and work becomes a healthy social outlet. I think when we all started working online it felt creepy NOT to do with with our online coworkers, so we tried to replicate the same thing.

But what if working online looked very different than working offline — what if working remotely meant that we just showed up at work to work, having rich and fulfilling social lives out in the real world?

So when I started Paperbell I decided to try something different — what if I ran my online business in a completely different way, eliminating everything that I found tedious or unnecessary about the way I’d worked before?

Your Business Is Your Utopia

A quote I revisit often comes from Derek Sivers’ book Anything You Want: Your business is your utopia.

The joy of being a bootstrapped founder is that we get to create the rules and do it however the hell we want! So I decided to really think about what my utopia company looked like. Here are some of the themes that came up for me:

Less Chatting About Work Instead of Doing Work

I’ve spent a huuuuge amount of time as a founder in meetings talking about work instead of just doing work. And I’ve found that setting this time aside to talk about work (in regular meetings, one-on-ones, and topic-specific meetings) tend to spin off MORE time in conversations about work.

Here’s one common pattern I saw: I have a weekly 1:1 with someone on the team. We spend the time chatting about ideas for the business —sounds great! Some good ideas are emerging! But these are almost never high-priority ideas. (Because we’ve already had different planning meetings and figured those out.)

But now the ideas are in the meeting notes and “in the system”. Now we spend time and effort deciding if we’re going to do them, or another project goes off track trying to incorporate these ideas. Sometimes I had to eliminate the idea and have a tough conversation with the person about why we aren’t doing their idea.

But often no one even cared about this idea in the first place or thought it really needed to be done, we were just making conversation!

These endless conversations lead to an endless amount of low-priority, nice-to-have type of work. It’s fine. It’s not terrible. But why? Why introduce this unneeded element to the business?

Freelancers Instead of Employees

At MeetEdgar, we didn’t rely on freelancers much at all. We had a strong preference for hiring W2 full-time employees that were completely devoted to the business.

But gradually I started to notice something — the freelancer relationships I’d had in the past felt more clean, clear and direct than the employee relationships.

Surprisingly, I find its often easier to get clearly-scoped work delivered regularly from freelancers than employees. A freelancer usually has a black-and-white directive: we need 10 blog posts written by this date. They write them and get paid. Done.

Employees are usually juggling a lot more inputs, including the endless meetings mentioned above! So the deadline you agreed on keeps slipping and slipping as other things come up. Meanwhile, the freelancer would have had it all done by now!

Particularly as an American company, I also came to resent the “babysitting” aspects of running a company. We were responsible for people’s health insurance and 401k and I personally believe these basic rights should be provided by the government, not tied to your employer.

Hiring freelancers feels much more fair and even — they are running their own practice and I’m their client. If they want to raise their rate, or change their hours, or work more or less that’s a mutual agreement between us intstead of something the employer dictates.

Individual Contributor Instead of a Manager

I want to be a wrecking-ball founder. I want to rewrite our homepage whenever I feel like it, I want to change our email strategy on a whim, I want to go into canva and randomly create and launch a bunch of new ads.

I’ve run online business for 20 years and I’ve put a lot of thought into the work I love to do. Being the manager ain’t it. I love diving into the marketing and getting my hands dirty.

I’ve created situations in the past where I wasn’t “allowed” to do this stuff and for good reason — we had teams of people whose job it was to create the marketing, while I sat in the CEO seat. But I’ve found this is not my favorite role. So in my business utopia I need a situation where I’m playing with marketing.

The New Remote Vision

These ideas came together to form a larger vision of what Matt Mullenweg refers to as “Level 5: Nirvana” . Here’s how he describes it:

This is when you consistently perform better than any in-person organization could. You’re effortlessly effective. It’s when everyone in the company has time for wellness and mental health, when people bring their best selves and highest levels of creativity to do the best work of their careers, and just have fun.

Another book that was highly influential on me is Trevor Blake’s Three Simple Steps (as well as Secrets to a Successful Startup). In these books he describes running a business solely through agency/vendor partners. This idea clicked into place with a Forbes article I had read about Kylie Cosmetics. Here’s the important part:

Her near-billion-dollar empire consists of just seven full-time and five part-time employees. Manufacturing and packaging? Outsourced to Seed Beauty, a private-label producer in nearby Oxnard, California. Sales and fulfillment? Outsourced to the online outlet Shopify. Finance and PR? Her shrewd mother, Kris, handles the actual business stuff, in exchange for the 10% management cut she takes from all her children. As ultralight startups go, Jenner’s operation is essentially air.

A software business doesn’t need a manufacturing partner or a huge media buying agency. But if real businesses had created huge success with tiny teams, why couldn’t I do the same?

I’ve also learned a lot from Christine Carillo who writes about running tech startups with tiny teams and outsized results.

I had a vision of a company whose work got done by a few subject matter experts who didn’t need management or one-on-ones, who knew exactly how to do their work with excellence on day one and loved what they did.

Another part of my vision was ultimate efficiency — a company that truly eliminated any work that wasn’t important. I wanted to spend a few hours only doing the very most important things. (This has also lead to the approach of nearly everyone at the company, including myself and my cofounder, being part-time.) Zero busywork, and swift elimination of anything that didn’t create business results.

What Impact Would This Have on MRR?

As a SaaS, our core metric is MRR (monthly recurring revenue). For your company maybe you’re using profit instead of MRR, or annual growth depending on what your goals are.

The most useful filter question I’ve found is very simple:

What impact would adding this have on MRR?

or, EVEN MORE IMPORTANTLY

What impact would ELIMINATING this have on MRR?

Shit.

When I looked at how I’d been running things, using all the “best practices”, the playbooks from Scaling Up and Traction, the meetings, the OKRs, and on and on . . . a huge amount of it would have NO IMPACT ON MRR if it was removed.

None.

In fact, the harsh truth is most businesses find entire roles that can be removed with no impact on MRR. (Yes, you do not want to start this out as a team exercise because it gets very awkward very quickly.)

This filter question has been hugely helpful in continuing to refine my Utopia business model.

And Now For The How

All of this is important to set the stage for how we achieve a super-functional, efficient company without meetings.

We aren’t just taking meetings away. We’re building a company from the ground up that makes meetings unnecessary.

Part two coming soon on exactly what we do instead: the tools, structures and working practices we use to communicate and run the company day-to-day. Please leave a comment with the questions you’d like me to answer in part two!

From 2007–2015 I ran what were then called “infoproduct” businesses. Businesses where I was the thought leader, and I created online courses around my expertise.

In 2014, I parlayed this expertise into my first SaaS business, MeetEdgar. MeetEdgar was a runaway success, and the story ended for me with a successful exit.

Since the term infoproduct is pretty dead, lets call now call it an online expert business. This is a business that really centers on the creator, their skills and also their image and personality.

Experts are different from influencers — an influencer shows their life and promotes other people’s products (sometimes launching their own physical product line).

An online expert makes money from online courses (the new name for infoproducts!), coaching, consulting, newsletters, podcasts, etc. They have a certain area of expertise that they teach and create content about.

Expert businesses are ALL about the audience. In fact, they often create their audience before their product. They might create a bunch of content about their topic on LinkedIn, TikTok or Twitter then create a course or membership based on the sub-topic that their audience shows the most interest in.

This is a proven model, and because it works so well for experts the model has trickled over into the SaaS world.

If you visit IndieHackers you’ll hear the advice to create an audience first, so that you have someone to sell your SaaS to. They’ll even tell you that the audience can steer the direction of the features created in the SaaS.

But for almost every SaaS business, this is terrible advice that will lead to a huge amount of time wasted under the guise of “marketing”.

It shows a fundamental misunderstanding of the difference between expert and SaaS businesses, and how the customer’s buying process is dramatically different in each. (More about that soon.)

As someone who has been on both sides, I’ve been super surprised by some of the core differences between each model. And if you’re in one wanting to switch to the other, I want you to go in with eyes wide open!

So let’s do it — how does a SaaS business compare to an online expert business?

It’s MUCH Easier To Sell An Idea Than a Tool

This idea is so counterintuitive that almost no one sees it coming.

Before I launched MeetEdgar, a social media scheduling tool, I sold a course with a methodology for social media scheduling.

I figured if people were willing to buy the course, they’d be willing to pay for the tool to just do it for them without all the complicated spreadsheet management the course involved.

And my thesis turned out to be correct — but not for the reasons I thought.

When Edgar launched in 2014, social media scheduling tools were an established category. Buffer & Hootsuite were already popular, prospects were actively looking for a SaaS solution.

Edgar was able to enter an existing category and add an innovative take it. The business took off, reaching $1m ARR 11 months after launch.

But despite it’s fast growth, I actually found it MUCH HARDER to sell a SaaS than a course! I could not understand this at all — why would you want to pay hundreds of dollars for a course that does nothing on it’s own when you could pay $50 a month for that work to just be done?

You Pay For a Course Once, You Pay For a SaaS Again and Again

Online courses are a one-time buying decision.

If the expert can get you excited about the course and make big enough promises, you will shell out hundreds or thousands for these imagined outcomes.

They “get” you in a hyped-up launch and you buy. That’s the model.

(Speaking of that — did you know almost every course business is entirely launch-based and sells basically nothing on “evergreen”? Yeah, not exactly how they make it sound.)

A SaaS however, is an ongoing subscription (duh). If you aren’t using it, you aren’t going to pay for it. The business could use similar methods to get you hyped about all the incredible outcomes that will come from their tool, but when the next month rolls around and you haven’t actually picked the thing up, you’re going to cancel.

The dirty secret of online courses is how little they get opened.

The truth is, the course model does not rely on customers consuming the content. It’s a one-time sale. And surprisingly, you can even get customers to purchase even more programs from you, even if they never cracked open the first one! New dream outcome, new purchase.

Customers Don’t Impulse Buy SaaS

Customers don’t impulse buy SaaS (and if they do, they likely won’t stick around long).

The creator model generally works like this: create an audience, get them excited for your new thing, they buy it*.

*(Notice “make the thing” isn’t a step — that’s because that often happens AFTER the sale!)

The SaaS model works like this: create a product, explain the use case, prospects research the category and choose one.

Just think about each model from a buying research perspective.

What’s the last SaaS you purchased? For me, it was a new split testing tool after Google Optimize shut down.

Did I research options? You BET I did, extensively. I compared prices, tried out different tools, and chose a winner. (By the way, a low price point was a key factor in my buying decision.) And if I didn’t actually run split tests on it, I would cancel it straight away.

Compare this to a course. If you buy a course, you’re likely following the creator and found out about it from their marketing. Let’s say it’s a course about copywriting. When you heard them announce it, did you go out and research and price-compare other copywriting courses? The answer is likely no. You heard about it, you trusted the creator, you bought it. It’s a completely different process.

(Yes, sometimes we actively look for education in a certain area although this tends to be free resources like blogs and videos. Even then, purchases usually follow an audience-first model: we subscribe to someone’s youtube videos about the topic, get to know their content, THEN buy.)

Why It Almost Never Works to Create a SaaS Around an Audience

There was a time when every course person wanted to get into software, and I saw SO MANY half-baked software attempts that flopped.

Here’s how the story usually goes:

Let’s say the expert has an engaged audience around time management. So they think OK let’s do a time management SaaS! It can include a calendar and a to-do list, I’ll get recurring revenue and be a gazaillionaire!

Sometimes the launch even works OK — the audience is excited and wants to support their beloved creator by trying out the tool. They get some buyers.

But the buyers quickly realize . . . wait there is much better software out there for these problems (in this case, a ton of excellent and free calendars and to-do lists).

The expert did not actually work out the business case for viability around a new to-do/calendar tool and how much people would pay for it. They just tried to create “something softwarey” around their niche.

Even worse are the glorified spreadsheets — they sell what’s basically a branded spreadsheet with their special “categories” as columns. This might work as a free download, but no one is paying for it month after month!

SaaS Marketing Is Completely Different

Marketing is my wheelhouse, and I have sold $10m+ in both online courses and SaaS subscriptions.

I kinda know what I’m doing here.

And I can tell you that the marketing strategy for SaaS’ vs online experts is COMPLETELY different.

When I promoted my online courses, I followed the industry standard of a launch model. (Where you “launch” the course with a big promotion and open sales only for a limited time.) I created a schedule for the year, and put marketing budget behind these large launch events.

(I actually really miss those big wall calendars where you’d get your whole year mapped out!)

In my SaaS businesses, we don’t map out our marketing plans over the year. We create marketing flywheels that keep growing. SEO, google ads, cold outreach — whatever it is, you’re improving a marketing system that attracts qualified leads and turns them into customers.

And speaking of qualified leads, that’s a whole different game in the two models.

Because goooood luck taking someone who is mildly interested in your category and selling them a SaaS!

Let me give you an example: this year I have been working on increasing my cooking skills. I read cooking blogs, look for recipes, and follow my favorite creators on instagram.

However, I have ZERO use or desire for a cooking-based software product. They can be my favorite chef ever with the best recipes, I’m just not interested. Putting all their recipes in a database and calling it a SaaS ain’t gonna cut it.

But what could they sell me? They could sell their audience group or 1:1 cooking lessons, or an ebook of recipes.

SaaS businesses need to target people who are either actively looking for their solution (this is always best!) or have a very strong and clear use case for it. Not people who just have a related interest. And an audience signals people who like your content, not people who have a problem that they need software to solve.

Content Marketing Still Works For SaaS

My SaaS Paperbell (c’mon over coaches!) relies heavily on content marketing. We’ve created an extensive library of blog posts that are highly targeted for our target customer, and this is a super effective discovery mechanism. I’m not saying content doesn’t work for SaaS.

What I AM saying is the content should not come first. Don’t build the SaaS around the audience, build the audience around the SaaS.

Productivity systems. Make ’em fancy, make ’em simple. At the end of the day they need to achieve one thing — making sure the reality of how you spend your time matches your intention.

You really can’t dive into productivity without first figuring out what the heck you should be working on, AKA priorities.

The absolute bible of this topic is the book The One Thing. Honestly the title alone tells you a lot, but I’ll give you the rest. The core question is of the One Thing philosophy: What’s the One Thing I can that will make everything else easier or unnecessary?

(Hint: get that done first.)

However, I don’t follow the entire system of the book — in fact I don’t really follow any of it, and I specifically am not a fan of time blocking. (You’ll see how I DON’T follow a planned ahead schedule, and what I do instead later in this article.)

Figuring out your priorities is a whoooole other topic! You can be the most productive person in the world, but who cares if you’re not getting the important stuff done. And it’s VERY, very easy to spend all day on things that don’t make a difference. I would say it’s the default human state. So you really have to be diligent about not sliding into it.

OK, so assuming you know what you want to do, how do you make sure it gets done?

Here’s how I do it.

And I have to say — I’m gonna go ahead of give myself a gold star in getting priorities done. I’m not perfect, but I’ve worked part-time since 2015 and had some pretty major success in that time.

Currently, I work 10–15 hours/week. I want to be clear this is not some “hack” for writing three books a week in just fifteen hours. I do not have a huge amount of output. What I create is results — making sure my business is a machine that’s creating an excellent product for coaches and making a great profit doing it.

I do want to state clearly that I launched my current business, Paperbell, while working part-time. (Actually not only was I working part time, but I had a two year old and five year old at home because we launched during the pandemic in 2020. So yeah, definitely not a lot of extra work hours happening.)

I’m throwing that in because something I hear a LOT is “sure, you work part-time now, but it’s impossible get something off the ground without a ton of hours”. Well, I’m living proof that it’s possible.

Monday Morning Planning

The big secret to getting the right things done is planning ahead before you sit down to work. You don’t want to be trusting your whims, your inbox, your slack, or your latest shiny object to guide your time.

I do my weekly planning on Monday morning. Some people do it Sunday night, or the end of the day Friday, that bit doesn’t matter.

Here’s my Monday process:

✅ First, I check my goals/priorities

This can be your one page annual plan, your quarterly goals, OKRs, KPIs — really doesn’t matter what system you use. What matters if you have decided ahead of time some kind of plan for what’s important. I generally like to pick three big rocks per quarter, which I put in a priority order.

I keep mine in a google doc that’s on my chrome bookmarks bar so that I can easily reference it throughout my workweek.

Here’s the thing — you usually can’t actually just keep hammering away at your One Thing until it’s done.

You’ll probably be waiting on information, other people, etc. In your weekly planning, you’re figuring out what you can do THIS WEEK to make progress on your priorities. Maybe it’s sending a follow up email, sourcing something, completing a piece of it, meeting with someone. The important part is that it’s being chipped away at.

So I take break down my “big rocks” into what needs to be done THIS WEEK and create tasks for myself in ClickUp that are due this week.

Sometimes I do it as a subtask under one big rock item, or it can be it’s own standalone task. I find details like that really don’t matter.

✅ Next, I review what else might be on my to-do list

In the screenshot you’ll see a clickup board called “current sprint”. We don’t really use a “sprint” system, I just like the name! Anyway this is kind of “current random stuff” that doesn’t have its own board (for example, our blog has its own board).

Here’s what each column means:
JAN — FEB — MAR That’s a way of saying “this quarter” — as a way of reigning myself in, I try to only put things on this board that I want to happen this quarter. Otherwise it has to go on my “ideas” board and could get pulled in next quarter.

PREP These are the items that are coming up next — sometimes I am still gathering parts or ideas for them, or this column can be a way of showing the shortlist of what will happen next.

CURRENT self-explanatory

CLOSED self-explanatory

My current sprint board is where all the random things I want to get done get deposited during the week. (They automatically go in the first column as a kind of holding pen.) These could be tasks I created, or could be pulled directly from my inbox or slack (using integrations).

So on Monday I review the state of the current sprint board to see if anything has gone overdue, and what’s on there that I have room for this week.

Notice that this happens AFTER reviewing my priorities list. This is how you make sure that your big priorities are getting space before all the random minutia. (AKA big rocks before pebbles!) This is also when I take things on the current sprint board and assign them to other people.

✅ Lastly, plan my tasks for each day in ClickUp

OK, this is where the actual “to do” list happens. I take all the tasks I want to get done this week and assign them to myself with a deadline. Then I use ClickUp’s weekly view (again, bookedmarked on my chrome toolbar) which automatically shows each task on the day its due. Now I have a rough plan for the week.

In the past, I’ve done this plan on paper but currently I’m finding using the ClickUp weekly view is the most effective for me. It gives me an easy short-hand for if something is a “real” task — if its assigned to me, with a deadline it will show up here and needs to get done. (Tasks without a deadline won’t show in this view.)

Actually Doing The Things on The Plan

MAKING the plan is one thing, FOLLOWING the plan is another!

As you can see from the above, I do pick a day for each task and spread my tasks out over the week.

But here’s something that might surprise you: I do not stick to that daily plan.

I do what I feel like in the moment — as long as it’s on the list.

For me, this is the perfect balance between making a smart plan ahead of time and being “in flow”. If I’m in a writing mood, I can pick off all my writing tasks. If I’m in a spreadsheet mood, I do that.

The other important practice I have is not making my schedule jam-packed. You can see on the screenshot above the most I have on one day is 5 things — but sometimes those things are 5-minute tasks. I try to really use the Monday planning time to filter what is essential for moving the business forward, and totally eliminate any busywork.

This means that sometimes I get my “week” done by Monday or Tuesday. If that happens, excellent. I have space to mess around with other things that I’m interested in, like writing this article!

How I Work With My Team

This article is about how I work, but I am certainly not creating results alone!

The Paperbell team is 100% part-time or project-based freelancers. We have a small team of regular part-time freelancers, and we pull in subject matter experts for one-off or sporadic projects (for example, designing a free report PDF). At my last company MeetEdgar, our team was almost entirely full-time, W2 employees. (And to be clear I worked part-time for most of my years there as well.)

At the time of writing, my work is a mix of CEO type work and marketing individual contributor work. The CEO work includes things like making budgets and projections, making sure activities are matched to strategy, keeping everyone in the loop, and sourcing and hiring people to work with. My marketing work includes activities like writing emails, giving specific direction for marketing initiatives, putting together promotional sequences, writing ad copy, and keeping up on marketing trends/strategies.

If my team sends me something to review or give feedback on, I make it into a task. Or, they’ll create a task for me directly.

More Strategies I Use To Get a Lot Done in A Short Amount of Time

👉 I use focused work session apps

I regularly use both Centered and Flow Club: these are tools that set up a container for your work session and remind you to stay focused. In flow club you join live coworking sessions, and centered is great for an “on demand” focused work session.

👉 I work in a dedicated office

Instead of working from home, I rent a private office. This is a great way to remind myself that I’m there to WORK, not mess around pinning ideas for my living room which I can do on my laptop at home. I’ve got a giant monitor and everything I need to stay productive and focused (and none of the distractions I don’t need!)

👉 I get up when I find myself “messing around”

When you find yourself messing around on random tasks I find the best way to combat it is to physically get up out of your seat. Stretch, look out the window, reset.

I check in with myself — am I done working for now? Do I want to take a walk? Do I just need to re-open my weekly plan and get myself focused again? Basically I check in with how I’m feeling and what I want. I have a little reset and stop myself before I go deep down the internet rabbit hole!

👉 I don’t have meetings

My calendar is a barren wasteland and I love it. We have no recurring meetings at Paperbell, and it’s very rare that we have a live meeting about anything. So I actually have ALL of my work time to get my priorities done, not the tiny sliver left over once the meetings are done.

We’re an entirely self-serve business so we also don’t offer any kind of sales calls or demo calls, and working with large partners is also not part of our business. I know a lot of founders get their time eaten up with 1:1 sales calls, but I’ve always run my businesses on one-to-many marketing vs 1:1 sales from day one. I’ve actually never done a sales demo for MeetEdgar or Paperbell.

👉 I‘m an Inbox Zero devotee

My inbox is always a small, and I hit zero at minimum once every week. Inbox zero stops you from “using your inbox as a to-do list” because your to-do list genuinely isn’t in there. (I alluded to it earlier, but the short version of my inbox zero system is forwarding anything to my ClickUp list that actually needs to be done. I also do a lot of deleting, and don’t share my email publicly.)

👉 I work limited hours

This one is a little snake-eating-its-own-tail, but I believe that the less hours you have to get things done the more efficient you are. I don’t know about you, but I slam through tasks when it’s that last hour before school pick-up/time to meet your friend for happy hour!

The act of limiting my work hours in itself makes me more efficient. I’ve trained myself that work time is actually for getting shit done, not scrolling twitter or sitting in useless meetings for hours.

👉 I’m a ruthless delegator

I save my time for the two buckets of work I described above — CEO work and marketing work. (To be clear we also have a ton of marketing work that happens without me, like all of our content marketing.) Everything in your business needs to get done by someone, but that someone does not have to be you!

I pass off most tasks from the start and also “stop, drop and delegate” when I find myself spending time on something that could easily be done by someone else. For example, I’m not very good at putting spreadsheet data into visual representations or figuring out a complex formulas. So if I find myself diving into one of those tasks I’ll stop, delegate those parts of the work, then come back to do the final analysis.

I also wrote about how I’ve had others handle customer service from day one here.

That’s it! Everything I do to run a successful, profitable SaaS company in 10–15 hrs/week.

If you’ve been around the entrepreneur “motivational” space for a while I can guarantee you’ve heard this type of maxim before:

Wealth is a Measure of ValueYour Wealth Equals The Amount of Value You’ve CreatedTo Make More Money, Create More Value

While listening to yet another podcast repeating this stance, I realized exactly why it irks me so much and why it can lead entrepreneurs astray.

Last Saturday, I had to cancel a party last-minute and ended up with a big catering order. I searched for somewhere that could use the food that day, and found The Clock Tower Sanctuary, an organization that supports homeless youth here in Brighton, UK. The stars aligned and I was able to donate the catered food for their lunch that day.

Does The Clock Tower Sanctuary create value in the world? Yes. A huge amount. They serve people who have nowhere else to turn. I’m sure lives have been saved due to their work.

Do they create wealth? No. I certainly hope that their founders have not gotten wealthy from the project! Their budget does not automatically increase for every person they serve. (That would be nice!)

What about my children’s teachers? I’m immensely grateful for the value they create, and in my opinion their pay check is not even close to a match for the value they create in the world. Some children will have the entire trajectory of their life changed from one teacher.

So does value create wealth? No. Of course not.

And this sentiment is inherently insulting to all the people creating extraordinary value. Value which is very often completely unrelated to wealth creation.

We can also see that the equation is untrue in the other direction — does wealth come from value creation?

Well, can people create wealth without creating value? Yes.

That’s the whole concept of rent-seeking, often discussed in Nassim Taleb’s popular books.

There’s also the good ol’ scammer/grifter/charlatan. You can create huge wealth selling people outright lies. Or you can use manipulative sales tactics to sell something that the buyer immediately regrets, like time-shares. You can definitely create ANTI-value (making people’s lives worse) and make a whole lot of money because of it.

Why “Value Creates Wealth” is Bad Business Advice

OK, so we’ve proved it untrue. But it’s also unhelpful for entrepreneurs.

CAN creating more value create more money? Yes. Add more value to your offering, charge for it, if people agree to pay for it you’ve created more money.

But by pretending that statement stands alone, a lot of entrepreneurs get led astray. First, it really implies the ol’ “if I built it, they will come” doesn’t it? It makes it sound like if you just create something valuable enough the money will somehow start flowing.

In the SaaS space, I see countless aspiring entrepreneurs who want to build something cool but don’t want to tackle the marketing/sales side of the business. They’re hoping the product’s value will somehow be enough. It is not.

This advice also detracts from the very important yet often uncomfortable skill of making money.

Making money is a specific skillset that you generally need to have if you want to . . . make a lot of money.

And there are many different ways of making money — sales and marketing in your own business, buying shares of other successful businesses, salary negotiation at your job.

But looking at these things head-on often feels . . . icky? We would rather just focus on a nice agreeable concept like “value” than admit that if we want to make more money we may have to do something scary like learn how to build a business or start a new career path.

So it’s time to kill this frustrating and insulting “definition” once and for all. Value does not create wealth. Wealth-building creates wealth. Value creates value.

As a bootstrapped founder, doing your own customer service comes with the territory. When you first launch you just have to, and then it often just continues on by default. I’ve met $1m+ ARR founders who still do their own support.

Doing your own support is also part of the cannon of Known Startup Wisdom. It’s supposed to keep you close to customer requests and ensure you build what customers are looking for.

I’m now on my second successful bootstrapped startup (exited MeetEdgar, now growing Paperbell) and both times I’ve brought on customer service help within the first few months. Here’s why.

Reading every single request makes you build the wrong things

The squeaky wheel gets the grease. When you have a very emotional, strong-willed customer who insists that something is a disaster and they will be taking their business elsewhere it is VERY hard to resist the urge to build what they’re asking for. Even if they’re not even your ideal customer, no one else has brought this up, and you’re pretty sure no one else cares. (Sometimes the customer insisting upon it doesn’t actually care either! You just caught them on a bad day.)

It’s too easy to tell yourself it will “just take a sec” and that in these early days it’s worth keeping their business. This could be true if you have a big whale client, but my businesses are self-serve, “prosumer” businesses where you need volume. Every minute we spend building something that only benefits one person is a minute we spend NOT building something that would improve our core feature set for everyone else.

Always-on customer support makes deep work impossible

I have seen so many early founders brag about being on live chat all day — an instant, “always on” availability for their customers.

It’s too easy to spend all day on piddly conversations with customers that hit the chat button right away because it’s easier than looking around in the software or support docs. These conversations are not a good use of your time, and you either can literally spend all day on them OR be constantly interrupted from your flow state of all the other dev/marketing/sales work you need to do.

Even if you don’t use a live chat tool, it’s really hard to mentally tune out the support inbox and go into deep work mode for three hours when you know that customer requests are rolling in. You know you shouldn’t check, but who can resist?

Resolving customer issues is an easy dopamine hit that makes you avoid harder problems

As a small business, sometimes I need to take support back over myself when we’re in between people or training someone new. I’ve noticed that answering tickets can be addictive — it’s a tidy little problem that you can completely resolve. As a marketing-focused founder, almost none of my other work is like this. I’m doing things like trudging away at long-term content marketing plays that will sloooowly grow our search traffic a few months from now.

So I find myself constantly checking the support inbox in order to get that hit — it’s the kind of work where I can feel like I’ve resolved something, even if the business would be much better served with my time on higher-priority projects. Who has the willpower to force yourself to do something “hard” when you can answer tickets all day?

If you find yourself continuously “busy” but not accomplishing projects that move the needle forward, the first change I would make is getting someone else to do customer service.

Support help is “cheap”

Yes, I know you aren’t supposed to say it that way. But when you look at all the hats you need to wear as a bootstrapped founder, support is the one where there is LOT of talent out there.

So let’s do the math here — even if you have a very low support load (I’m looking at you, dev tools) the mental overhead and task-switching cost is still extremely high. Why would you not hire that out to focus your time on other things? As a bootstrapper, you likely can’t afford an experienced marketer or developer in your first year, but you likely CAN afford a freelancer for an hour or two a day who can handle 99% of your support tickets.

. . . And you can still stay in tune with customers

The core argument for doing your own support is to stay connected to customers. Guess what? You can do that much more efficiently by READING the messages instead of answering them.

You can have your CS team put information in a feature tool, a spreadsheet, or you can simply take 15 minutes a day to skim through the previous day’s tickets.

And don’t worry, as a small team you will still have plenty of opportunities to get stuck in! Speaking of, before I finished this article god smited me and I received a message that our freelance support person (currently there’s only one) will be off for a week soon, so the load will be back on me. Plenty of opportunity for that good ‘ol customer connection!

At the end of 2021, I sold my bootstrapped SaaS business MeetEdgar.

I had made it to “ramen profitable” with my next company Paperbell (a tool for life coaches to run their online business) and proven the model. Now that Paperbell was a go, it was time to devote my full attention to it and move on from the company I had started seven years before.

This article is specifically about the process of selling your business, and more specifically selling it to a “micro PE” company like I did.

Here’s the exact process I went through, a process you can duplicate for your own business as well.

First, Learn All The Things

Aside from selling my interest to a business partner, this would be my first “real exit”. So I wanted to go in as knowledgeable as possible.

I started out by reading all the books I could get my hands on about selling your business. I discovered that preparing your business to be sell-able is a big topic, but there are actually surprisingly few books about the actual process of selling.

Luckily, one person wrote an excellent book and one excellent book is all you need!

The first and last book you need to read on this topic is The Art of Selling Your Business by John Warrillow. The book gives a detailed overview of the process that I personally found to be very accurate. Plus, I found myself using many of the negotiation tactics I had learned in the book.

If you sell a business without reading this book, you are dummy. There, I said it!

I would also recommend the book Before The Exit by Dan Andrews. This one isn’t as step-by-step, but is particularly good for understanding the “gotchas” of different types of sellers.

I also listened to many episodes of Built to Sell Radio (Adii Pienaar’s is probably the best SaaS episode).

After doing my research, I had a pretty solid idea of the type of buyer who would be the best match for my company and how to pitch them.

A Word On Brokers

Someone who helps you sell your business could be called a broker, an advisor, a banker, an M&A advisor, etc. All of these terms have blurry definitions and can take very different approaches to selling your business. I talked to many brokers (most would not call themselves that), some who were very helpful and knowledgeable and some who were borderline scam artists.

Let me just put one clear word of warning here: there are some brokers who charge very large up-front fees ($20,000 and upwards). From what I’ve been told from others who know the industry better than me, these brokers often make more money from the upfront fee than selling businesses, and have a reputation for doing very little. Buyer beware of a large upfront fee.

Strategic vs Financial

After thoroughly researching the lay of the land and talking to several brokers, I felt I could see two differing paths in front of me: a financial sale or a strategic sale. A strategic acquisition means the acquirer has an interest in more than just the cashflow of the business. It could be a product they want to add on, or a new market they want to get into. Strategic buys often have a higher multiple, but you are also dealing with large corporations and the process involves many hours with accountants and lawyers, and generally takes at least 6 months. (Strong caveat: no personal experience here! This is what I learned from general research and talking to others who had been down that road.)

At MeetEdgar we serve only small businesses so we had no big clients to talk to about a strategic acquisition (this seems to be the most common type of strategic acquirer) and there were no obvious strategic partners on a buying spree.

A financial acquisition, however, seemed like a bullseye match for my company. We were in the right revenue range, super profitable, and I saw a group of “micro PE” firms very active in acquiring software companies like mine.

So I decided to go the financial route, AND I decided to go without a broker. If I had been looking for a strategic buyer I would have absolutely needed help, but I felt confident in my abilities to approach and negotiate a financial buyer on my own.

Please note I certainly don’t feel that everyone should go at this alone and in many cases I think you will definitely end up with a better outcome going with a smart advisor. But this is my story, and that’s the road I took.

Contacting Micro PE (Private Equity) Firms

I had a very clear ideal acquirer: a firm that acquires profitable SaaS businesses with low-millions in annual revenue. These are often called “Micro PE” but they wouldn’t all call themselves that and that can really mean lots of things. (Yes, it’s confusing.)

Since my business was under $10m ARR we were a bit small for most “regular” private equity firms. (But again I can’t emphasize enough that none of these are hard and fast rules and exceptions happen all the time.)

So how did I find Micro PE firms that are looking to buy SaaS businesses? Google! Yup, I’m serious.

But you don’t even have to do that because I’ll give you the list right now. Here is the list I was able to find in late 2021 — please add more in the comments and note these have not been vetted in any kind of way:

• BigBand (I am a scout for them, please reach out to me if you’d like a warm intro)
• TinyCapital
• Scaleworks
• Saas.group
• Ramp Ventures
• HRX Capital
• Dura Software
• Bloom Equity
• LTV Fund
• Verne
• Timberwind
• Calm Capital
• Mudbrick Capital
• Horizen Capital
• Osceola
• Organic Equity
• Fullstack Capital
• Evermore Industries
• Constellation Software
• Enduring Ventures
• Southport Ventures
• Sureswift
• itrinity

I contacted them cold, just using the public information on their website.

Here’s the thing: if they buy profitable SaaS companies of a certain size, and you’re looking to sell a profitable SaaS company of a certain size, you’re going to get a pretty great response rate.

Here’s the initial email I sent:

Not that hard, right?

If they replied with interest, I sent over some very topline numbers like number of customers and annual recurring revenue, and from there we set up a phone call.

I was very transparent about all numbers right from the beginning — I didn’t want to end up in a situation where the buyer would find surprises during due diligence that would cause them to look at the deal in a different light.

In many acquisitions there are all sorts of “special” spreadsheets and financial reports created to slice and dice the numbers in different ways. I didn’t bother with any of that, in fact I never created any custom reports for this process! I just sent over our usual P&Ls, stats from profitwell, etc when they time was right.

During this phase I was also interviewing lawyers so that I would be ready to go when an LOI (Letter of Intent AKA the offer) was sent.

Levelling Up My Negotiation Skills

Before this process I would have considered myself an average negotiator. At MeetEdgar we’ve always been self-serve so I’ve never done a single sales call, much less in-depth negotiations. So I definitely wasn’t any kind of seasoned negotiator.

At the same time, it was a skill I was interested in leaning into and getting better at. In the past I had read a few of the sales/negotiation “classics” like Spin Selling and The Challenger Sale. But during this time I read ONE book that hugely helped me up my negotiation game.

It’s called Winning Through Intimidation! Yes, either the best or worst name ever depending on your perspective. It’s actually not about how to intimidate others, but how not to let others intimidate you.

The Art of Selling Your Business also has some excellent negotiation tips. One that I used directly from the book was to make sure to have a “no re-trading” conversion before due diligence kicked off. (“Re-trading” means changing the terms of the deal during the due diligence process.)

By far the most useful concept that I went to again and again in the process was the idea of BATNA. BATNA stands for Best Alternative To A Negotiated Agreement. Basically, your BATNA gives you the ability to walk away from any one deal. In my mind, my BATNA was actually holding on to my company. Edgar was profitable and we had a team running it that required very little of my time, so it was “easy money”. It only made sense for me to sell if the sale price clearly exceeded that reliable “easy money” reliable paycheck.

When you’re selling your business, you have to hype yourself up a bit. As entrepreneurs we generally spend our days looking at everything that’s wrong with our business so that we can work on making it better. But when you’re selling, you have to flip the script a bit and focus on this incredible asset that you’ve built.

The truth is there are a very finite number of companies worth buying. I reminded myself of this a lot — if they wanted a profitable, bootstrapped (the bootstrapping is attractive because there’s only ONE owner to negotiate with) SaaS company of a certain size ready to sell now, I was hands-down their best bet!

Honing In On a Buyer

I’m not going to detail the entire process I went through with potential acquirers, because Warrillow’s book does a very thorough job of that.

In my case, I had several parties interested right from day one but one stood out as the most serious: Sureswift. (Since I sold my company to SureSwift the leadership team that I worked with has left and are now with BigBand — reach out to me on twitter if you’d like me to make a warm intro for you.)

While others would wait a week between calls, Sureswift was always great about keeping the process moving and scheduling the next point of contact. When I spoke to them they had already acquired 40 SaaS companies which meant they had the process down cold (which made things a lot easier for me).

I ended up in a situation where Sureswift was ready to send me an LOI and two other companies were “maybes” — they were interested but not at the LOI stage yet. This might seem like bad news but I actually used it as a negotiation point — I told Sureswift that I would abandon my “maybes” but it had to be at a price that I LOVED, otherwise it wasn’t worth my while to lose the chance that my maybes would send an even better offer.

Sureswift was able to make moves in days which gave them a huge advantage over other slower companies. And after some back and forth they sent an LOI that was a “hell yes” for me. I would say negotiating the offer and receiving the LOI was the most exciting part of the process, for some reason it was even more exciting than the actual close!

Due Diligence And Close

Due diligence was REALLY easy and straightforward. We had a 30 day period which also gave my lawyer time to review the purchase agreement (there was very little that needed changing or discussing). All of our code was in Github, all of our transactions were in Stripe. We have no custom features for certain customers, no one with their own special price who mails us a check every quarter, no shenanigans of any kind! Self-serve SaaS is truly a beautiful model.

The Sale . . . What Was The Big Number?

Doing everything online meant the actual close was pretty anticlimactic! In my case it looked like constantly refreshing my screen waiting for the escrow company to release to my bank account.

The day the money hit was a weekday and my husband and I got his mom to watch the kids after dinner so we could walk to a local bar on the beach and have a few drinks. Yup, that was it! Everyone asks what we did to celebrate but with two young kids we’re not exactly dashing off for a glamorous week in Paris.

I agreed to a six-month transition period where Sureswift can ask me any questions needed to transition the business to their ownership. This has been an incredibly painless process and we’ve always been good about keeping processes and information clear and organized so there wasn’t a ton to ask about.

As for the price, I’m not able to disclose the price or multiple. On the podcast Startups for The Rest of Us (here’s a great acquisition episode) I’ve heard host Rob Walling ask founders if their exit was a “life changing” amount of money: my answer is yes.

How I’m Spending My Time After The Exit

The week after the acquisition closed I took the week off but didn’t go anywhere. I just lived my regular life without work for a week. I choose to do this to see what life without work would be like, and to remind myself that this is an option for me — I no longer need to work for money.

Of course after the week was up, I was right back at it! I love running a business and we’re at an exciting growth stage with Paperbell.

I did get a lot of clarity from the exit on the path that I desire as an entrepreneur. I absolutely plan to sell Paperbell, and I can now see clearly how much I love the launch and initial traction phase. I don’t have a desire to get to $100m ARR or build a massive team. If I can keep building, launching, and getting to product-market fit I think I’ll be a pretty happy camper.

I love podcasts, but I hate interview podcasts. I know, it’s weird! But I can’t be the only one.

When it comes to podcasts, I’m looking for an incredible story. A narrative thread, some cliffhangers, and to really capture my attention it has to be a true story.

The defining podcast of this genre is the very famous Serial (which is excellent, for the record). But it’s a murder podcast. And sometimes you just don’t want a story about a real human being killing another real human being, ya know?

So, straight from a professional podcast listener, here’s my list of excellent, gripping narrative format podcasts that are NOT about murder. (And are all 100% true!)

These are vaguely ranked from must-listen to meh. But I only included podcasts on this list that I finished and would recommend. (Believe it or not, there are a ton more I listened to that didn’t make the cut!)

The Dream Season One
I haven’t met a human yet who didn’t absolutely love this podcast. Listen to Season One. LISTEN TO IT. This is at the top of the list for a reason!

The Trojan Horse Affair
DAMN this was good, and co-created by the creator of Serial you expect nothing less. Education is a common theme on this list, so a podcast that follows an education story with some truly jaw-dropping moments is sitting right at #2. I don’t even want to tell you what it’s about because the topic doesn’t sound that juicy, BUT IT IS. Just listen.

The Missing Crypto Queen
This is one of the most bananas real-life podcasts you will ever hear, so many great cliffhangers that left me dying for the next episode. The Bulgarian crypto beauty pageant is too good to be real, and a scene you will never forget.

The Retrievals
Does anyone else associate books and podcasts with where you were when you consumed them? I listened to this one while wondering around Tokyo so it has a deep association for me. Anyway, this one hit me hard. It kind of manages to capture what’s F’ed about being a woman in America. I’m not even going to tell you what it’s about. Must listen.

Exit Scam
I had to put this one below Crypto Queen because the stories are bizarrely similar. This is a different shady crypto founder who also disappears. The production value isn’t as excellent as Crypto Queen, but still a really interesting story.

The Gateway: Teal Swan
This podcast absolutely haunted me and I still think about it (and get mildly creeped out) all the time. It’s a deep dive into Teal Swan, a “self help” leader who focuses on suicidal people. She is a deeply fascinating character, and since I’m a big self-help reader myself I loved exploring some of the darker sides of this world.

No Compromise
I would honestly say this podcast is a must-listen for every American, especially if you feel confused by Trump supporters. No Compromise reveals a LOT about America, including how many of our state representatives are “out” white supremacists. I was also fascinated to learn about Christian Reconstructionism. (Google it or listen to the podcast!)

Chameleon: Hollywood Con Queen
This is one of the most “holy shit that’s too incredible to be true” stories on this list. Plus it has a great surprise twist!

The Shrink Next Door
A top pick because it’s so fascinating and insane it’s hard to believe it’s real!

Believe in Magic
I’m putting this above Scamanda because no one does audio storytelling like the BBC and this is a very similar story that got way less press. Some absolute jaw-dropping moments here. Just full on banger of a scam podcast!

Scamanda
Oh this one was GOOD. Lots of deep juicy interviews, lots of WTF moments, and it just keeps getting worse and worse. If you love scams it’s a must-listen.

I’m Not a Monster
This one is pretty unforgettable — a white American mom joins ISIS and takes her kids with her — WTF? This is a really well done podcast with in-depth reporting of what happened, including recordings of propaganda videos made by her kids. Disturbing AF . . . but no one (OK, none of the main characters) gets murdered, hey-o!

Gangster Capitalism: The College Admissions Scandal
I find “gangster capitalism” a really dumb name, don’t let it deter you from listening to this excellent podcast!

California City
I LOVE A GOOD SCAM. And this show is all about a scam that’s gone on for decades (and still goes to this day!) selling land with no value in the middle of nowhere. The best part was probably discovering how the company lets the useless land go to auction when the taxes are no longer paid, buys it again, then sells it to another sucker.

I Was Never There
What if you were raised on a hippie “back to the land” farm and then in a punk house? And then, as an adult, you made a podcast about it with your mom? That’s basically what the score is in I Was Never There. Ostensibly about a missing person, but I loved diving into the mother/daughter relationship and portrait of a unique place/time/movement.

Uncover Season 1: Escaping NXIVM
Cults are right up there with scams on my favorite topics list, and I gobbled up stories from a few different sources about NXIVM. This one was the best — a great, creepy, complex story told right from how it started.

Startup Season 1: Gimlet
There have been a lot of seasons of Startup, some much better than others. This is the original, and the best. Truly captured the raw emotions of the emotional journey of starting a company.

Startup: Success Academy
This is the second best season of Startup, even though it’s one of the least “entrepreneurial” seasons. I found learning about Success Academy fascinating

Shell Game
AI talking to customer service, AI talking to children, AI talking to AI! The premise of this one is a journalist makes an AI clone of himself and releases it into the wild. Definitely gave me a deeper understanding of how AI works, and had a lot of funny moments.

The Mysterious Mr Epstein
Hey I said these didn’t involve murder, other horrific crimes are fair game!

Hoaxed
SATANIC PANIC. Another fav topic right up there with cults and scams! This podcast from Alexi Mostrous (see also Sweet Bobby) covers a modern Satanic Panic case set in the London suburbs. Includes a fun chase through Morocco!

Filthy Ritual
If you loved Hoaxed, listen to Filthy Ritual next. It’s very glam with Hampstead Heath and Suriname. Memorable characters, wacky hijinks and scams, scams, scams!

Surviving Y2K
I have to say this one falls under the “Dan Taberski podcasts where nothing much happens” umbrella. However the narrative arc weaving his coming out with Y2K is just some of the finest podcasting of all time. And that’s from someone who (clearly) LISTENS TO A LOT OF PODCASTS.

Dolly Parton’s America
Honestly I’m cheating by including this one as I doesn’t really have a strong narrative, it’s more of a collection of Dolly-related themes. However, the lesbian interpretation of Jolene is one of the many shining moments that make the whole series well worth a listen.

Sick: Season 1
I like creepy stuff, what can I say? This one is a fertility doctor who used some “unorthodox” methods, and what happened in the aftermath.

Rabbit Hole
Honestly this one starts out really captivating then fizzles a bit, but I still made it to the end. It’s basically an exploration of how some of the extreme right-wing ideas on the internet spread, with a Q-Anon primer thrown in for good measure.

Tiffany Dover is Dead
Oh, you like podcasts about Q-Anon? Then you’ll probably be into this one about Covid misinformation! This goes deep on how a verifiably false story is able to spread deep and wide on the good ol’ internet. A great reminder not to believe everything you read (or see) online. (See also Death by Conspiracy on this topic.)

Heaven’s Gate
OK I’m stretching the “not about a murder” definition here a bit, but I will maintain that this is about a cult, not a murder. Really well done and gave me a deeper perspective on something that felt like just random odd news trivia before.

Nice White Parents
I had a strong personal interest in this one as I attended schools just like the ones discussed on the show, where “nice white parents” go in to change (and insert their children) into schools in low income communities. The show explored a lot of interesting themes on race, class, and how they get tied into education.

Sold a Story
Throwing another education one in — this one isn’t the most exciting on the list (if you want the most exciting education one it’s DEFINITELY The Trojan Horse Affair) but it was a pretty interesting story about how these big decisions get made like how to teach kids to read.

Sweet Bobby
Sweet Bobby is basically the ultimate catfishing story. Plus it’s kind of a follow-along whodunnit, as I’ll give a minor spoiler and let you know the catfisher is someone we are introduced to in the story. It was pretty painful at times to listen to the “mark” insist that she was not gullible, as she was incredibly gullible and believed some absolutely outrageous stories from the catfisher. Ultimately it’s a twisty story about someone who had years of her life taken away in a very strange way.

Do You Know Mordechai
I’m sticking this under Sweet Bobby because it’s the same topic but I thought Sweet Bobby was a bit better (sorry!). Still, this story is well worth a listen and a different slant than Bobby because this one leaves you feeling quite sympathetic with the catfisher. Best moment is all the victims of the catfisher banding together to make their own crackpot detective team!

Defining Diego
Probably the most wholesome one on my list. This examines all different sides of international adoption, from an American mother and grown son who was adopted from Guatemala. I learned a ton and there were some really unforgettable deeply emotional parts of the story. Definitely cried while listening.

Sent Away
Teen treatment facilities! Scams, abuse, craziness — so up my alley. This podcast explores the whole industry from the insane way kids are kidnapped in the middle of the night to the lack of government oversight on the facilities.

The 13th Step
The title refers to the “13th step” of 12 step programs which is hooking up with people from 12 step programs! This contains some disturbing stories of sexual assault, fair warning. The podcast covers a lot of ground of the underbelly of treatment facilities, how they’re run, government programs, and the whole drug treatment world. Super interesting.

Dear Alana
Again we dodge the not-murder classification just barely with one about suicide. But really it’s about conversion therapy which I generally find fascinating. This one is unique as they had a lot of the main character’s journals that the show recreates with an actor.

Toxic
This one could have gone a bit deeper in the storytelling and journalism, but still worth a listen overall to understand more about the insanity that is Britney Spears’ conservatorship.

A Very British Cult
About a cult that got people to . . . sit on zoom calls all day? Made me think damn you really can get people to do ANYTHING, how boring! A different cult angle from the others on this list that’s, well, Very British. Also if some of the others are too intense for you, this one stayed pretty tame.

My Year in Mensa
I suspect you’ll either find the host of this podcast hilarious or outrageously annoying. I’m on team hilarious, and the air horn never got old. This is the only one on the list that would also fall into the comedy genre. Not my usual thing, but entertaining overall.

Death by Conspiracy
OK this one is clearly about a death . . . but it’s not a murder, he died from Covid! Gotcha! This was an interesting exploration of someone who fell into the covid conspiracy rabbit hole, and it definitely gave me insight as to how it happens. If you’re into this topic, you may also want to check out We Were Three, but honestly I didn’t love it enough to make this list.

Betrayal
Not about murder, just sexual assault of a minor! This is like listening to outrageously juicy gossip, and I love how the wronged wife banded together with the victim of her husband’s abuse instead of blaming her. If you think YOUR ex is bad, this podcast will cheer you right up!

Southlake
This one caught my attention because everyone who went to the University of Texas like I did knows someone from Southlake, a suburb of Dallas. If you’ve ever wondered how people started the wild theory that “critical race theory” is being taught in elementary schools, this podcast gets to the bottom of it.

Inconceivable Truth
This paternity mystery had some good twists and turns as well as really lovely heart-warming moments. It just didn’t linger with me as much as some others on this list, but if you’re interested in DNA/family stuff give this one a listen.

Missing Richard Simmons
I have to spoil this one in advance and warn you that nothing happens. This a podcast with no resolution, not even close. But at this point I am a Dan Taberski superfan and will listen to anything he does, and this was no exception.

Fed Up
This is a fun one but at the bottom of the list for a reason. I definitely enjoyed the drama of two influencer’s instagram feud, but the podcast is about as surface as it sounds and the story doesn’t really go anywhere. Still, this is one of the only podcasts mentioned that contains zero dark themes so I thought it deserved a place on the list!

Added in December 2024: Shell Game, Defining Diego, Sold a Story, A Very British Cult, Filthy Ritual, Scamanda, Believe in Magic, The 13th Step, The Retrievals, Dear Alana, Inconceivable Truth

Plus, Two Honorable Mentions That Didn’t Fit the List

In The Dark: Season Two (Curtis Flowers)
This one is sort of about murder, although gory details never appear. It’s really about the complex, incredibly length case of the man who was tried six times for the same crime. It’s riveting storytelling about race and the criminal justice system in America, and it’s a true must-listen.
Bone Valley is another excellent one if you’re interested in social justice.

Beach Too Sandy, Water Too Wet
And on a very, very different note (what was I thinking putting this after the Curtis Flowers podcast??) this is one isn’t about murder, but it also isn’t narrative. It’s a brother and sister reading yelp reviews, and it thoroughly cracks me up every time.

This article was initially published on the Ropig blog on February 15, 2018.
Ropig was ultimately shuttered in 2018, you can hear that story here.

By November 1, 2017, I know one thing for sure: we’re going to run out of money.

We were supposed to have launched by now, but things got a little off track. And while no product is ever done exactly on time, this one had actually gotten pretty close!

My husband and co-founder Chris and I had decided to invest $500k of our own money into our latest project, a developer alert tool we call Ropig, but we knew that if we didn’t put a hard cap on that investment, it could easily turn into a money pit.

So with our launch just out of reach, the numbers were clear: on Jan 31, 2018, our $500k would be gone, and that would be that.

It left us with about three options:

1. Break our commitment to ourselves and go beyond our budget? No, we’d set a hard cap for a reason. This business needed to prove its own viability, not turn into a pet project that constantly drained cash with no output.
2. Go the true bootstrapper route and just work on it ourselves, for free? No, it would slow down the project too much — and that would mean taking even longer to get to a healthy monthly revenue. (And honestly, we’ve gotten used to working with an amazing team at MeetEdgar, and going it alone doesn’t sound like much fun.)
3. Raise money from outside investors? Ding ding ding! It quickly became the obvious choice — the one thing that would allow us to keep going down the path we’d always envisioned and planned for Ropig.

But there was one huge problem with fundraising: I’d always been vehemently against it.

I believed, and still do, that the traditional Silicon Valley model of fundraising is badly broken, and leads to the goal of growth at any cost.

Not exactly how I like to run a business.

So the question became: is it possible to raise money without compromising my own integrity, and the integrity of how I run my companies?

Is there a way to raise money without saying we’ll sacrifice all our morals for the sake of growth?

A way to raise money without committing myself to 80-hour work weeks until we just get acquired and I can finally step off the hamster wheel?

I was about to find out.

My first foray into fundraising

In late October, I’d been serendipitously invited to a dinner here in Austin, where I met an investor who was pursuing a new model: a way for startups to raise money while also prioritizing profitability, instead of just growth that burns through cash until they’re acquired.

In December, I approached them with our product.

Ropig was, in many ways, the perfect fit for their portfolio, so even though they didn’t love that we were still pre-revenue, it felt like it could be a slam dunk.

They were open to writing a check for every dollar we needed — another $500k — and the calls we had once or twice a week always ended the same way: they thought they could make the investment, but couldn’t confirm just yet. Every time we scheduled a call, I thought it would finally be the one where I got my answer, and every time, it remained a maybe.

During this time, I made the mistake of not pursuing other funding options. I was overwhelmed by the prospect, and having had little success talking to traditional VCs and seed funds in the past, I had no confidence in my ability to do it again.

In my head, this investor was one inch away from saying yes, so I figured in a worst-case scenario, I’d come up with a few Plan B options and go from there.

But with December coming to a close, I still didn’t have an answer — and I might be stuck in these conversations until my bank account hit zero. So I gave him a deadline: I needed an answer by December 31st.

I got it on December 29th.

It was a no.

With my best prospect gone and $500k to raise by January 31st, the clock was ticking — and that meant I went into action mode.

But when fundraising isn’t your thing, where do you even start looking?

Initially I considered some kind of equity crowdfunding campaign through a platform like WeFunder. If there’s one thing I know, it’s online campaigns and launches, and I had been behind the scenes on successful crowdfunding campaigns before.

But the amount we were trying to raise — half a million dollars — made this option pretty daunting. With public campaigns like these, people are often putting in tiny amounts — closer to $1,000 each — so we’d have to find 500 funders within just one month.

Adding to the problem, Ropig is in a totally different space from the online audience I’ve built up over the years — it’s a tool for software developers, whereas my existing audience is largely creative entrepreneurs — and that means the people most likely to invest would have no interest in or use for the product.

As someone who’s been working for herself for the past 10 years, though, I’ve built a strong network of colleagues over time — many of whom are entrepreneurs that have not only built significant wealth from their businesses, but successfully raised investment capital for them, too.

So after a few calls to get the lay of the land from friends who had raised successful angel rounds, it was time for me to start knocking on doors. (Or in my case, typing up emails.)

Over the last few days of the Christmas holiday, I scrambled to put together the deal structure and investment information for investors.

On January 2nd, 2018, I sent my first pitch email.

In the first two weeks of January, I pitched 250 people over email — there were a few new people I was introduced to, but the 250 was 99% existing connections. (Hey, I’ve been going to conferences for 10 years — I know a LOT of entrepreneurs!)

Setting the minimum investment at $25k, I’d need 20 takers to meet my goal. Believe it or not, though, that list of people I emailed didn’t include everyone I know. (I’ll tell you in a minute how long it took to narrow it down.)

Because Ryan Delk, who became one of my first investors, gave me some advice I would not forget: this is a long-term relationship. Never accept money from anyone you don’t actively want to be in business with over the long haul.

So before sending each email, I asked myself if this was someone I would be genuinely happy to make a part of my new business. And honestly, some contacts, even very “important” ones who seemed likely to invest, did not pass that test! My circle is mostly founders, not investors — and while some of those people have done a little investing anyway, some had never done it at all.

When my January 31st deadline arrived, I had closed $300k. (Another $50k would trickle in after.) I hadn’t met my original $500k goal, but I had come damn close — and most importantly, raised enough for the show to go on.

Here’s how I did it:

My Seven Steps to Raising $300k in 30 Days

Step 1: Figure out your general terms and legal structure

The two most common choices for a seed round are SAFE (Simple Agreement for Future Equity) or convertible note. (Go ahead and Google those if you need to. Before January, I didn’t know any of these terms!)

A convertible note has a hard date by which you need to either raise your next round or repay investors, which didn’t offer me the flexibility I wanted for future fundraising decisions — so that option was out.

Based on some Googling and conversations with other entrepreneurs, I decided to do a SAFE, with no discount and a $5m cap. SAFEs don’t actually require you to set a date when your fundraising round ends, but I set a close date of January 31st anyway — not only for my own sanity, but to help motivate potential investors and keep moving toward our launch.

But here’s one thing I wish I’d known.

While my lawyer had said I could do a SAFE with an LLC — the structure of the company at the time — I didn’t realize that the standard Y Combinator SAFE would have to be modified pretty heavily to make sense for that structure. This didn’t come up until the middle of the round, which meant some quick and extensive research with CPAs and lawyers to determine if I should switch to a C corp, which is more common in Silicon Valley startups.

I ultimately kept the LLC structure — but it would have been a lot smarter to sort all this out BEFORE I started fundraising in the first place!

*** Note added in Oct 2024: you should most likely do a C-Corp due to QSBS

Step 2: Put together your deck/investor information

Most people use a deck format, but I actually put everything in a Google Doc instead.

Here are the sections my doc included:

• Round details (how much I was raising, what structure, when it closed)
• Overview of the product
• Overview of the founding team
• Go-to-market strategy
• Competitive landscape/market opportunity
• Where we’re at now (in my case, explaining that the product was complete, and that we’d be launching in February)
• The future (what we expected the future of the company to be/how they’ll make their money back)

This was a fairly unconventional choice. I didn’t create a traditional deck, complete with pretty charts and stats that — in my opinion — would sound impressive but not necessarily be all that useful.

Honestly? I have no idea if approaching things this way helped me or hurt me! But also, those templated decks bragging about billion-person market size and making big promises make me want to hurl, so I figured my investors might feel the same way.

Step 3: Pitch (almost) everyone

Like I said, my process was very different from what you often read about pitching angels — especially because I was only pitching people that I knew. That meant the first step was to rack my brain for anyone who might be interested.

Here are a few things I did:

• Looked through my friends on Facebook/people I followed on Twitter
• Looked through the speaker lists of conferences I’d been to in order to jog my memory of speakers/attendees that I had met
• Looked through my phone contacts
• Looked through everyone I had ever emailed from my work account (this one meant I read through 1,236 names, one at a time!)

Emailing one person would often remind me of others to reach out to — maybe mutual friends, or people I had spent time with at the same conference.

I set a deadline for myself: I was going to email my entire list of 250 names by January 15th — and this process was 100% on me. I had a template to work off of, but I sent every individual email myself.

This process was surprisingly exhausting.

It was emotional, and I constantly had to work up my nerve to hit send on the email. I was asking people for a LOT of money — people who may or may not have any interest — and I had to constantly remind myself that I was offering an amazing opportunity, not asking for a favor!

During this period, I also reached out to and was introduced to a few traditional seed or VC funds — but unsurprisingly, none of them panned out.

It’s very unusual to meet a firm and have them write a check upon meeting you — it’s usually more of a long-term relationship, and frankly, that makes sense. Also, not clearly committing to raising a series A within a certain time frame meant I was generally a no-go for traditional VC. (Yes, I could have BSed about that — but I just don’t have it in me.)

Step 4: Follow up like your life depends on it

My follow-up system was to use Boomerang to send emails back to me a few days after I sent them.

This system wasn’t 100% foolproof, and a few fell through the cracks, but in general, it worked well. I didn’t want a completely automated system, as I was also talking to some people via other means, like text, and wanted to make sure I could customize everything before sending if I needed to. This also allowed me to follow up more with people who I thought were likelier to invest, and bother the people who seemed like long shots a lot less.

(By the way, the longshot category generally meant that they had never done a startup investment before. Most people who ultimately said yes had done at least one startup investment before, and were generally already familiar with the process.)

I followed up 3–5 times with each person I pitched — and you wouldn’t believe how many people wrote back on the third email thanking me for following up. Most people give up too soon, but the people you’re reaching out to are busy, and you are not their first priority! And really, even if someone had zero interest in hearing from me, receiving five emails over a few weeks and then never hearing from me again is not that big a deal.

Step 5: Track and close your maybes

If anyone responded with any kind of follow-up question, or any response other than “no,” I added them to a spreadsheet. A better salesperson probably could have converted some of those initial no’s, but I just thanked those people and moved on.

If someone made it to the spreadsheet, I followed up every few days and tried to schedule a phone call. From those initial 250 emails, I ended up with a spreadsheet of 46 people, and my goal was to get a clear yes or no from every single one.

(And for what it’s worth, at the time of posting this, I still have three maybes hanging out on the spreadsheet! Sometimes it’s hard to get a response.)

Out of my final 12 investors, all but two wanted to get on the phone to discuss things further. I ended up doing one casual in-person meeting with someone who happened to live here in Austin, but I never had to travel.

Something that I didn’t expect was the huge outpouring of support I received from the pitches.

So many maybes said they’d like to invest later, and so many initial no’s wrote me lovely messages of support! One of the unexpected upsides of fundraising has been the small army of people I’ve gathered that have actively told me they’d love to help make the product succeed however they can.

Although some people introduced me to new potential investors, I ended up with only investors that I had strong existing relationships with. The shortest relationship was about a year, but I’ve known most of my investors for more than five years. So while I raised $300k in 30 days, the groundwork was many years in the making — and a real testament to the importance of networking!

Step 6: Send paperwork for signature and wire instructions

By this point, you’ve hopefully discussed the details with your lawyer and CPA and have all of your paperwork ready to go. In my case, the paperwork was just a three-page SAFE agreement that myself and the investor each needed to sign.

Once I finally had the LLC thing sorted out, I sent the agreement out to be signed digitally via HelloSign and emailed my bank details for wire instructions.

That’s it!

(These things always feel like there’s supposed to be something more official to mark the occasion than there actually is.)

Step 7: Keep your investors in the loop and get to work!

Your investors are excited about what happens next, so don’t forget about them once the money has landed! I started by sending them an overview of the launch plan, and will send updates as the launch goes on.

While fundraising was a relatively painless experience in the end, it is not something I hope to repeat anytime soon. (And since it introduced me to a few people who were interested in writing larger checks post-revenue, if we end up raising again in the future, those will be the people I go to.) For now, I’m grateful to be 100% focused on our launch, which is scheduled for February 21st.

What I Should Have Done Differently

As a first-timer — and one on a serious deadline — I can see now that there are things I could have done differently.

Things like:

My pitch could have been better

A friend gave me the feedback that my pitch doc lacked passion, and I think he was right.

To be totally honest, I was scared and uncertain when I started this process. I didn’t know if the product I had worked so hard to create had a future, or was about to die a sad, broke death. I think this lack of confidence sometimes came across, and I wish I had gotten myself in a better headspace before I started.

I doubted myself constantly

Similar to the point above, I was constantly second guessing myself for two very big, very different things — one, raising money at all, and two, not taking the typical VC path.

When you talk to a VC, they obviously believe that their way is the best way — and they can make that argument fairly convincingly. Was I making a huge mistake by not pursuing millions in funding right off the bat? And on the other hand, was this whole thing a waste of time? Should I just go back to bootstrapper land where I belonged? Fundraising is emotionally exhausting, because you’re constantly trying to prove your worth.

I didn’t ask for more from investors

In retrospect, when someone said yes, I probably could have pitched them to invest more — after all, I knew they were interested! This is just a missed opportunity I never pursued.

I didn’t try to create hype or scarcity

While I used my January 31st deadline as a bargaining tool, I never used the typical tactics of acting like we were oversubscribed, or as though investors would lose their spot if they didn’t give me an answer in the next two hours. Since I was pitching people who weren’t professional investors, it was really important to me that they not feel pressured, and feel 100% comfortable with spending their money.

From a marketing point of view, though, I could have done a better job creating excitement and sharing reasons to get involved throughout the process. I had some maybes that probably would have turned into definitelys if I had tried a little harder to paint the picture.

At the end of the day, I’m glad I embarked on a process that gave me experience in a major aspect of business ownership that I hadn’t encountered before.

(And most importantly, it allowed Ropig to live on!)

Will I fundraise for my next company? (Which I hope doesn’t happen for a loooong time!) Maybe, maybe not. As smart as I think it is to leverage other people’s money, I still love the bootstrapper mentality.

Ultimately, though, Ropig was a more expensive product to build than MeetEdgar, which we didn’t raise money for. Some products naturally need more money to get off the ground, while some can be built by a single programmer!

In the future, though, I’ll be less dogmatic about fundraiser vs. bootstrapper — and I’ll certainly have a better view of how many different paths you can take to build an incredible company.

I did a double-take when I read that a pair of self-made brothers were purchasing Asda.

If you don’t know Asda, it’s a massive British grocery/everything store, kind of the “Wal-Mart of the UK” (in fact, Wal-Mart is exactly who they’re buying it from).

For entrepreneurs who started their own business from scratch, with zero family wealth, and have only been in business about 20 years, this is an INSANE accomplishment.

So of course I had to read more about the Issa brothers and their story.

The short version is, they started by saving up enough money to buy a petrol station in 2001. Fast forward to today, their business owns over 5,000 petrol stations, control of Asda, 110 Starbucks stores, and 125 KFC’s.

It made me reflect on the lesson here for a much smaller business like mine.

So many entrepreneurs have big dreams. We want to turn our smoothie shop into the best known smoothie brand in the world, we want to be the top speaker on our topic commanding $50k for every talk. We want to grow our software business to 100,000 customers.

These are our DREAMS, but are they really what we’re going for?

When I think of the Issa brothers owning that first petrol station, I think about how many other petrol station owners would LOVE to have the same kind of accomplishment. Let’s say it’s owning 1,000 stations all over the country.

Now, in order to own 1,000 petrol stations in let’s say 5 years, what do you need to do?

There’s a pretty clear path forward — first off you’re going to need a LOT of capital, so that means you’re going to spend a lot of time securing funding.

You’re going to need to do bigger deals, acquiring multiple locations at a time. You’re going to need solid systems for management and operations, and great people on your team to be able to run and train this many locations effectively.

And yet the “regular” business owner, dreaming of owning their own petrol empire one day, isn’t doing any of these things. Not a single one. They’re spending their days running their one station.

They might dream of the empire, but they aren’t actually GOING for the empire. You wouldn’t observe them doing any actions that will lead to the empire.

Now, there could also be an entrepreneur doing everything the Issa brothers did but falling short of their incredible outcome. That happens all the time.

BUT, at least that person has a shot. If someone is spending their time raising money, actively looking for deals, and creating scalable systems they have a very good shot at achieving their 1,000-station goal. (Or at least making very strong progress.)

The person doing none of these things has almost no chance.

I think this is a lesson we can all apply to our goals, no matter what the size.

There’s what you say you want.

But what are you actually GOING FOR?

Have you read those “here’s how we got the .com” sagas?

Like the one Jason Fried recently published about buying hey.com. Or the classic tale of how Noah Kagan spent over ONE MILLION FREAKIN DOLLARS on sumo.com.

While these tales are impressive, I did NOT want to be one of those stories!

When I was doing the name research for my new startup, I wanted to make sure I could nab the .com right from launch day, without having to spend a million bucks in the process.

I did that by using a counterintuitive process that I’ve never seen anyone talk about. And you can use the same process to make sure you never get stuck bidding for an expensive .com after you’ve launched.

Most people go about naming their startup absolutely BACKWARDS.

Here’s the usual course of events: you come up with a ton of names, do a bunch of research, then narrow it down to a winner that you’ve fallen in love with.

THEN you start searching for domains based on the name you’ve chosen (can you get name.io? name.co? or maybe one of those domains where the extension becomes part of the part.ofthe.name?)

This is exactly how you fall into the trap of spending six figures (or more!) on the .com of your dreams.

But there IS another way.

Start with the .com, NOT the brand.

Here’s the step-by-step process to to grab a branded, (sort of) affordable .com right from launch day.

Step 1: Set Your Budget

OK, I know what you’re thinking: well this article is dumb, because no good .com’s are still available.

You would be right about that in the sense that no good .com’s are unregistered. But there are plenty of excellent .com’s that are available for sale.

The cheapest you can go for a decent .com is about $250. I set my budget at $2,000. I haven’t raised money for my new startup, but I am funding it with my own profits from my other business, MeetEdgar. (Which is exactly how I bootstrapped MeetEdgar as well.) I believe that a great, memorable .com brand is well worth a few thousand.

My $2,000 budget was plenty to have a lot of excellent domains to choose from (and remember, you may be able to negotiate below “sticker price”). I searched for domains with a published price of $2,000 or less so that I knew for certain I’d be able to get the domain for that price.

Step 2: Brainstorm Your “Branded” Words

OK, before we get here we have to take a little detour to what I personally believe makes a great startup name.

Here are some current naming trends that I think absolutely suck:

• Common object/word name. This one is SO POPULAR right now. Examples include Clubhouse (wait, do you mean the voice chat app or the project management tool?) Spoke, Blush, Finder (how the hell is anyone going to be able to “find” finder??) and about a million others because I just grabbed those from a recent producthunt search. They are hard (or impossible) to google, there are already a bunch of other things with the same name, and the .com is usually ridonkulously expensive. NO THANK YOU.
• Common sounds to make up a new word: This is better than the above because you can get the .com, so this is a path I initially went down myself. BUT the problem is these names are often notoriously difficult to remember. I recently tried out Sunsama which I thought was freaking amazing, but when I tried to tell someone else about it I found out I had no idea what the name was. Satsuma? Sumsama? Samsuna? The familiar sounds make it easy to spell, but don’t create an “anchor” of exactly what it is in your mind. Other examples of this type of name: Besedky, Elocance, Ameeolio (which looks like a really amazing project by the way, but has a very difficult name).

Now I’m not saying YOUR STARTUP WILL DEFINITELY FAIL if you use one of these kinds of names. I think many startups have and will succeed even with difficult names. But why not try to avoid these problems from the get go?

So what should you do instead? My preference, as you can guess, is exactly what I did with Paperbell — a combination of real words. These kinds of names are easy to spell, easy to remember, and easy to find because you can come up with one that’s actually unique. Other examples of this kind of name: Helpscout, RightMessage, ConvertKit.

Using real words will also give you a starting point in your name search. You may not end up using an “only real words” name — slightly modifying a short real word, like Trello or Pinterest, can also be a great option.

These “branded” words can have something to do with what your startup does, or can be more random. I would advise coming up with a ton and then playing around.

Step 2: Use Your Words To Search For Domains For Sale

There are endless domain name generators out there, here’s a great list to start with. I also found some of the larger domain marketplaces and sellers and used their searches. There’s no quick and easy way to do this, it’s just a ton of brainstorming and playing around.

Step 3: Save Your Top Contenders

For this step I just used a big, messy google doc which worked fine. I saved everything that I sort of kind of liked, and was for sale for $2k or less. Now you have a starting point of startup names where you know you can grab the .com for a price you can afford. Nice!

Step 4: NOW Do All Your Name Research

See how we’re doing this at the end, not the beginning? This is where you search to see what other businesses or projects are using this name, talk to people about the name and see if they remember it, play with what kind of images or symbols would be associated with the name.

This way you can “fall in love” with a name that you know you can buy, instead of falling in love with hey.com ;)

(If you’re curious, I ended up buying Paperbell.com for $1,795 from HugeDomains. I found they have a ton of great .com’s available for less than $1k.)

By the way, my new startup with the best name ever, Paperbell, just launched! Check it out if you could use an easy way to sell coaching services online.

After I retired from my business, the questions poured in about how I did it. It was a long process over 5 years but one key to making this happen is to start taking time off TODAY.

But is it really doable to take extended time off from a service business? (Without tanking your income?)

I’ve also gotten many comments and questions from people who see how this can be done in a software business, but not a service business. So today, I will address how you can start this process off taking significantly more time off in a service business — specifically, coaches and consultants.

Many service businesses think that extended time off is impossible for them, but the truth is its just a decision you make. The general strategy here will work for any kind of service business, though tweaks need to be made depending on what kind of service you’re delivering.

First, get out your yearly calendar and pick the two months you would take off in your DREAM scenario. No reality allowed.

I’m a believer we should always start by aiming for our absolute dream, ideal scenario then work backward from there. So, when would you loooove to take off?

Maybe it’s December when you just want cozy time with family. Maybe it’s May, your favorite time to visit your favorite travel destination! Maybe it’s July and August so you can just spend the summer playing with your kids.

How does your dream schedule compare to your real schedule?

Compare your dream months to the reality of your business. If you coach mall Santa Clauses to up their game (hey, ALL kinds of coaches are out there), December is probably not the best month for you. Or if you find you get a flood of new business every January, you should probably pick a different month.

So, now that you’ve compared your dream to your business realities, you know your two months.

Of course, two months is arbitrary. I picked that number because it’s a dream that many coaches have. But you can use this process for one month, four months, or taking a week off each month off all year long. Whatever floats your boat!

OK, but how do you take more time off without losing money?

Service businesses like coaches often struggle with taking time off because it’s essentially a “dollars for hours” model — the more time you coach, the more clients you have, the more money you make. So, taking time off can mean an unwelcome dip in income — but NOT if you plan ahead for it.

Let’s say you work 12 months per year and earn on average 4k per month. (By the way, most coaches do not earn the exact same amount every single month, so don’t stress if that’s you. This idea still works out, stick with me.)

4k/mo (on average!) x 12 months is $48,000/year.

So, if you want to earn 48k in 10 months (2 months not working), you must earn $4,800 per month. Going from working the full year to 10 months a year will always require a 20% increase in monthly earnings to work out the same.

So, what’s the easiest way to make 20% more? Raise prices by 20%.

That means if you charge $100 hr, charge $120. If you charge $25/hr, charge $30. Notice when you drill down to your hourly rate, this increase does not feel like that much. I’ve yet to meet a $75/hr client that cancels their contract when the price goes up to $90/hr.

It’s just not that big of a difference to your clients, but it can mean a huge change in lifestyle for you!

Of course, there are other ways to earn that 20% as well — opening an online course an additional time per year, doing another group program, etc. But that 20% increase is the simplest. And I LOVE a simple solution!

Don’t forget to account for this fluctuation in cash flow — if you charge hourly, you may be making zero money during your months off. As long as you plan ahead and put money aside, you’ll be fine — read the book Profit First, if you want to dig into the best way to do that!

Now let’s get into the logistics of making this real: telling your clients.

You want to let your clients know about your schedule as early as possible — this is another benefit to mapping out your entire year early. It lets both of you plan for the interruption in service. I’ve found that if you treat it as no big deal, your clients will follow your lead. People are used to their providers being off for vacations, illnesses, or various life events. This is just another version of that.

You’ll love how many people say, “Wow, that’s so cool, I want to do that too!” when you tell them you take two months fully off work every year. Let’s make this a thing!

Here’s an example of language you can use.

“Hi, Client! As we schedule our upcoming sessions, just a reminder that I take off the months of March and July.”

Seriously, don’t make it any more complicated than that.

Don’t ignore providing some kind of support for your clients while you’re away.

For most coaches, you don’t need to provide any kind of “fill in” service. They’ll simply be without you while you’re away. (Yes, they will survive.) If you want to get fancy, you could schedule check-in emails in advance they write back to. You can do this using the “schedule send” feature right in Gmail. Just make sure to manage expectations you will not be reviewing their replies until you’re back at work.

This can be a great way to be an “offline accountability coach” for your clients, even during your time off. For example, if you’re a business coach, you could schedule a simple what went well, what didn’t, what would you like to improve on email every Friday as an opportunity for your clients to reflect on their week.

If you have online courses, this could also be a good time to remind clients to lean on those. (And yes, you are completely allowed to be absent from your Facebook groups and online communities during your time off. Again, just clearly set the expectation ahead of time.)

If you feel you need someone to fill in for you, look for a coach with the same certification or training as you as they will likely use similar methodologies. You can either just refer your clients to them while you’re away or subcontract their services. (Meaning your client pays you, then you pay the coach a percentage of the hourly rate you were paid.)

A final word: don’t apologize.

When we do something bold for ourselves, it often makes us uncomfortable. Stand confident in your decision. Don’t start apologizing, bringing up how inconvenient you know this is or how difficult you think you are making their life.

AND watch out for a tendency to overcompensate! If you feel uncertain in your decision, you’ll try to throw in the farm for free — an extra session when you return, free access to a product you normally charge $500 for, you know the drill! Notice when you’re feeling this way, take a deep breath, and hit the pause button.

Ed note:

Hi! I’m launching a new business for coaches in 2020 — find out more right here.

Does something you’re doing for your business feel really hard? Like a constant uphill battle? Like you have to hustle your face off before you make any progress?

Then quit!

…no, I’m serious. Quit.

Quitting can be really, really good

Got an employee whose job feels like a constant struggle no matter what you do? Stop trying to make it work. They’re not a fit.

Got a marketing channel that STILL isn’t paying off, and you just can’t seem to find the right angle? Stop trying to make it work. That angle probably doesn’t exist.

Got an entire startup that can’t find that elusive “traction,” or even find the right product/market fit? Stop trying to make it work! Freakin’ QUIT, and move on to a better idea.

When I find myself struggling to “make it work” in spite of everything, that’s usually a red flag — a sign that I’m on the wrong path entirely. Because honestly, there are always so many alternatives out there that happen so much more naturally!

Good challenges vs. bad challenges

You know how sometimes you meet someone new, and they feel like an old friend right from the first conversation?

That’s how I want my whole life to feel. I want to to work with people who do great work, and to work on projects that I think are interesting and engaging.

That doesn’t mean there are never any struggles. That doesn’t mean there’s no hustle required, and no hard times to push through!

But in my experience, when you’re on the right path, the hard times feel very different. They don’t feel like fighting to “make it work” — they just feel like a natural part of the journey. Of course there’s still struggle, and of course there’s still uncertainty! At the end of the day, though, it adds up to something that’s ultimately rewarding.

And when you’re on the wrong path? Those hard times never get easier. Every decision sucks. There’s no light at the end of the tunnel.

Whatever it’s adding up to, it doesn’t feel good.

The myth of being a “real” entrepreneur

The truth is that I don’t actually find running my own business to be this gut-wrenching, stressful, anxiety-and-depression-inducing thing. If I did, I wouldn’t be doing it! But the culture of startups and entrepreneurship has reached the point where I actually feel a little nervous — a little guilty, even — admitting it.

I’m as worried about being struck down by my own hubris as anyone, but my startup has never consumed my entire life. It doesn’t make me question myself all day or keep me up all night. And I’ve been told over and over, and am still told to this day, that this somehow makes me not a “real” entrepreneur.

(Which would be news to me — my company is doing just fine!)

So I’m writing this to publicly offer an alternative. To say you CAN do things your way, and that if a decision is going to make your life incredibly stressful, you don’t have to do it. That in fact, that probably means it’s not the right path for you at all!

That doesn’t mean there will be no wrong turns. It’s taken me 10 years and four businesses to get to the place where I actually feel like my work is really reflecting my most valuable skills! It’s a constant process, no matter how far you go.

But in a culture that romanticizes hustle, struggle, and sleepless nights, I want to offer you the radical idea that feeling good is a GOOD sign. When things work out, when they fall into place, when you actually enjoy your work every day — keep doing that! (It doesn’t mean you’re not doing enough.)

And when you’re depressed, when you’re anxious, when everything feels difficult — you have permission to quit what you’re doing and try something different.

Honest.

More and more, though, people are taking this idea to the extreme. It turns what COULD be a decent holacracy into a total hot-mess-acracy, eliminating departments, managers, and a lot of the structure that makes workplaces actually work!

I get where the idea comes from. Everyone hates pointless rules and red tape, and bureaucracy slows down the speed of execution.

You know what else slows down the speed of execution, though? Forcing everyone to make a bunch of decisions every day that they’d rather not think about!

Stuff like:

Your working hours

Don’t you wish you could just make your own hours? “Get your work done, guys, we don’t care when!” Ahh — smells like total freedom.

Until you have to actually work with other humans, anyway.

Who’s online at what times? When are they available to meet with you? Can you expect them to be on this afternoon, or do they do their best work around 3 am? You’re waiting to hear back on some little detail before you can move forward, and nobody is around!

Now every person on your team isn’t just in charge of their work — they’re in charge of tracking the unique daily schedules of everyone else they need to interact with! So convenient, right?

The idea of total scheduling freedom has its perks, but it also adds massive administrative time even to tasks as simple as scheduling a meeting. You’ve avoided the bureaucracy of working hours, but by removing the simplicity of having the smallest clue as to when the people you need to talk to might actually be at work!

What we do instead:

Everyone at MeetEdgar works during normal working hours, relative to their own time zone, Monday through Friday. We keep a chart of what those hours are in every time zone, so it’s super easy to know when to expect people.

You naturally overlap with some people more than others, but you know who’s working and when, every single day. Plus, you never have to worry about if you’re working “enough” — actually, let’s talk about that some more in this next part!

Your paid time off policy

“Unlimited” vacation SOUNDS amazing, but in reality, it just means that you’re making everyone guess how much the people at the top secretly think they deserve. (Yes, this is as stressful as it sounds!)

Because “unlimited” isn’t REALLY unlimited, is it? Can someone take off 350 days? 35? Do they have any idea of what you expect is normal? Stop making people nervous that they’ll be fired every time they take a vacation, and just tell them how many days they have to work with.

What we do instead:

Simple: we offer a real vacation policy. Retro, I know! Not “minimum” vacation, not “suggested” vacation, none of that vague stuff — just four weeks of PTO at your disposal, and plenty of encouragement to use it. (Because taking time off should feel good, not stressful!)

Speaking of encouragement, though…

The stuff you’re supposed to actually work on

Imagine going to a restaurant, sitting down, and asking for a menu.

They don’t have menus. Order whatever you want!

Well, okay. Can the server make a suggestion?

“Nope, you have total freedom! Be in charge of your own restaurant experience, we’re not here to babysit you.”

You finally give in and order a steak, but it turns out they don’t have it. So you order meatloaf — they don’t have that, either. And, well, they SAID you could order anything, but they actually sort of frown upon people eating meat. So, don’t do that.

This is what it’s like when you’re in charge of determining your own work every day. First, there’s the politics of figuring out what you’re “supposed” to be working on. (Because while it’s technically up to you, nothing’s ever THAT simple.) Then when you DO figure out something that The Powers That Be secretly wanted you to work on — but didn’t tell you, of course, because it’s all up to you! — you also have to handle all of the project management. From scratch. Every time. How liberating!

What we do instead:

Managers exist for a reason, and it’s to make everyone’s job easier, not harder! Our managers (who we call advocates) work with their teams to set priorities every week, month, and quarter.

You aren’t handed a to-do list by your advocate every day — you still own your area of expertise, and are in charge of optimizing it. (If we hired you to do something, we trust that you know how to do it well.) But you also don’t have to guess at what you need to work on in order to be as valuable as possible to the rest of the team, either — there’s a dedicated person in place whose job is to keep the wheels turning smoothly. That’s why we call them advocates — they’re there to make your life easier!

The decision-making hierarchy

“We’re a flat organization — no managers to answer to here!” Cool, so does that mean I can change the price of what we sell? No? Who does? The founder? Okay, so we say there are no managers, but only because there’s one manager, and now every decision has to go through one person and everything is so hopelessly backed up that nobody can get anything done? Cool, this flat organization thing is very empowering.

What we do instead:

Decision-making power is distributed, and everyone knows how and why. Everybody on our team has the power to make the decisions that will allow them to get their work done, but our advocates are in charge of managing resources and coordinating logistics.

Like Zack Urlocker says, approval doesn’t add value. Knowing where to turn with ideas that could change the company, however, can make a big difference!

What does all this have in common? Structure!

When you run a business, it’s tempting to want to reinvent the wheel and turn it into the flattest, most liberated, most empowering workplace on the face of the Earth. But there’s something to be said about giving people structure!

Sure, we could do the whole flat management thing. But in my experience, I’d rather just set boundaries, let people know where those boundaries are and why they exist, and let them do their thing. They’ll spend a lot more time doing what you hired them for, and a lot LESS time trying to figure out how!