Today marks the 4-year anniversary of Late Checkout, the holding company I co-founded. Time flies when you’re having fun.

We raised $0, we have 8 figures of yearly revenue, 120+ teammates and have been profitable since day one.

I left my cushy corporate job to start a holding company in 2020. People told me not to.

“Focus on stability.”

“It’s too risky.”

“You’ve got a good job, why rock the boat?”

I'm so darn glad I ignored them.

Here are some raw lessons from the journey (and takeaways for your business):

1. Press doesn’t really matter. We never pitched to journalists once. We are our own press. When you have a product to promote, create meme pages, not press releases. Virality is the new credibility.
2. My love/hate relationship with investor updates. I used to dread writing updates to venture capitalists, fearing their reactions. I felt that if they read it the wrong way, I’d lose their trust. Now, I miss the thrill of the feedback loop. The fear (and accountability) kept me sharp. Bootstrapped founders could use some of this. You might put together an advisory board. I might.
3. The age of arbitrage/idea guy/gal. People say ideas are useless, execution is everything. I don’t know about that. If you’ve found a killer idea with a marketing channel, you’ve got arbitrage. And arbitrage for startups is massively underrated. Arbitrage is your oxygen. Ideas are useful, execution is key arbitrage is essential. Our best businesses found arbitrage.
4. What gets measured gets managed. When we had a clear owner and clear metrics, we usually did well. Focus on a couple of key metrics and have a clear owner for momentum. Without that, we underperformed. Without that, you’ll have a bunch of products in startup purgatory.
5. Being vague about your customer is a death sentence. When we nailed down our customer segment, magic happened. Margins soared, conversion rates spiked, and the team was pumped. When we were vague about our customers, and let anyone be a customer, problems would compound. Leave products for everyone to Google, but if you want a profitable internet startup, know your tribe.
6. The tax man cometh. In 2023, out of nowhere, our accountants informed us we owed a 7-figure check to the IRS thanks to new tax laws (section 174 for the US tax nerds). It sucked, but it’s a reminder to always be prepared for the unexpected. We give profit shares twice a year. Didn’t account for this. So, it was a good reminder to have professional accountants/legal you can trust and that something like this can occur at any point.
7. Build your recruiting machine. Most companies have sales machines or marketing machines, but building a recruiting machine is a nice to have. We were the same. Now, we take attract top talent so seriously. And affordable talent. We limited our hiring from NYC/SF because it kept me up at night. Just because they worked at Twitter in SF doesn't mean they are worth the cost. Build a recruiting machine for affordable, top talent.
8. From business to empire. BoringMarketing.com was just an AI-assisted SEO firm. Now, it’s Boring Holdings, with BoringAds.com under its wing. Lesson: build entities that can scale into empires.
9. I went into business with friends. They say don’t get into business with friends. How does that make sense? My co-founder and I went to high school together. We have a wonderful relationship. We both know each other well, our goals, and it makes for a productive relationship. And to be honest, it’s just more fun. I wish I had gotten into business with friends earlier.
10. I never knew of the productivity zone concept. I became 2x more productive when I found my productivity zone and designed my days around that. I’m able to work less and get more done. For me, this means doing creative work in the AM with my coffee, meetings only on Wednesdays, and having EA/operations support for repetitive tasks.
11. Obsessing over competition turns you into a clone. The more we paid attention to competitors, the more consciously our products began to look the same. That wasted time and money. Stay aware, but blaze your own trail. Innovation isn’t born from imitation.
12. Cash flow is king. I started to forget about enterprise value. Cash flow is the measure of a business I most care about. If it produces cash, it’s valuable—end of story. I removed the word valuation from my dictionary, replaced it with cash-flow and good things started happening.
13. Start with traffic, then build a business. Build a directory, build a meme page, build a community. Start there, and then go build a business afterwards, not the other way around. Note: for SEO hire BoringMarketing.com ​
14. Solve simple, everyday problems. Whatever you’re creating, the best businesses solve simple problems and explain it simply. Some businesses we created we're just too complex. They boiled the ocean. The best businesses go back to basics.
15. Ignore people. I tweeted about microsaas the other day. Some people chirped that building a microsaas is a waste of time. Disagreed. We’ve seen that "small" can be big. Ignore the people that try to convince you that you're building a small business.
16. Build the businesses one at a time. It’s tempting to build five at the same time. But in the early days, build an audience, build a community, build a product, get to $1M/year revenue, and then hire a GM. Then (and only then!) you can focus on building a new business.
17. Freedom is worth more than anything. When I was building VC-backed startups, I never fully felt free. Multipreneuring with no investors, I feel free. Do things that make you feel free. Whatever that is.

Next up, bookmarks I saved this week worth reading

#1

Dylan O'Sullivan @DylanoA4 Schopenhauer, write it down https://twitter.com/DylanoA4/status/1796126385569706454 Dylan O'Sullivan @DylanoA4 Write it down. You will forget it. You think you won't, but you will. Write it down. 9:19 AM • Jul 2, 2024 1264 Retweets 7623 Likes Read 34 replies

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Write it down. You probably know I love ideas. But the reality is I forget some of them. As soon as insight strikes, write it down. I even recently switched from Notion to Apple Notes because I find Notion lags a little. Can't waste a second when ideas strike.

#2

ST @seyitaylor I believe this very strongly. All consumer apps will be games. The biggest apps in the world are already games. https://twitter.com/asallen/status/1808161709536039172 Andy Allen @asallen I gave a talk at Config about play and building @notboring software… 12:34 PM • Jul 2, 2024 8 Retweets 82 Likes Read 7 replies

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I couldn't agree more. I design most of the apps I work on like games. Levels, status, leaderboards etc. It just works. It's human nature.

#3

Jay Clouse @jayclouse "For You" feeds are not for you. 8:13 AM • Jul 3, 2024 14 Retweets 144 Likes Read 29 replies

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Touché.

#4

George from 🕹prodmgmt.world @nurijanian Startup Playbook by Sam Altman (first published a month before the founding of OpenAI in 2015) Out of all the parts, great execution is my favorite (and is also the hardest) 1:15 PM • Jun 30, 2024 391 Retweets 3771 Likes Read 18 replies

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This pretty much has it all except for every company is a media company, hire affordable top talent and be profitable.

Thanks for reading Greg's Bookmarks.

Next up new startup ideas podcasts worth listening to.

New Startup Ideas Podcast (SIP) episodes 🧃 Brett walks me through some SaaS app ideas that would do really well. Also a dating app idea. ​Apple Podcasts, YouTube, Spotify​ A fun episode with Jonathan Courtney talking about how to avoid burnout and 1 local startup idea. ​Apple Podcasts, YouTube, Spotify​ ​ ​

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Thank you for reading Greg's Letter. I hope you found it valuable.

And don't forget to subscribe to my YouTube if this gave you any value. You'll get free startup ideas every few days.​

Until next week.

Be well,

© 2023 Late Checkout LLC
113 Cherry St #92768, Seattle, WA 98104-2205
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