@markmacleod_

26 years · Ex-CFO, Shopify & FreshBooks · $1B+ in exits · Helping tech founders scale without burning out. Subscribe to the newsletter. ⬇️

Join other Limitless Founders
Joined December 2007
I wrote a book. With 26+ years at the right hand of startup CEOs, this book is everything I've learned about scaling without burning out, in one place. The same principles Limitless members live by every day. It's called Limitless. Out this Fall. I've got 4 cover options and can't decide. Which one makes you want to pick it up? Drop your number in the comments, please. Thanks!
7
1
11
2,234
Most founders think a jammed calendar is a time problem. It's an org design problem wearing a scheduling costume. Find out where yours actually breaks: Take the Founder Energy Assessment: form.typeform.com/to/dFu6Xdb…
1
140
The old trade-off is dead. You CAN scale a massive company in founder mode.
1
3
173
Most founders design their calendar around what's urgent. The ones who make it to eight figures design their role around where their best thinking happens, then let their leadership team cover the rest.
1
3
190
Mark MacLeod retweeted
Founders: when things are going badly, your investors already know. * The updates slow down. * The numbers get vague. * You disappear for a while. Silence communicates plenty. Usually something worse than the truth would have.
5
2
13
741
Past seven figures, the job changes. Find one piece of friction today. Remove it. Repeat tomorrow. That's the whole system.
2
315
Play one point at a time. Every day is a point. Win today's and tomorrow takes care of itself.
2
279
Hustle culture is the biggest driver of startup failure.
1
327
Hire people who feel your company's mission as deeply as you do. Missionaries, not mercenaries.
2
4
349
You'll ask your team how they're doing in the 1:1. When's the last time anyone asked you the same question, and you gave a real answer?
1
2
333
Mark MacLeod retweeted
I’m slowly realizing that a peaceful nervous system might be a bigger flex than a perfect morning routine.
15
27
2
619
12,841
Gratitude is easy to feel on vacation. The real test is whether you feel it on a random Tuesday.
1
5
355
Every CEO drifts from the customer as the company scales. Calendar gravity, not apathy. Fix it with one recurring block: an hour a week on a real support call, not a report about support calls.
1
2
285
You already know the version of yourself that makes your best decisions. You just haven't built a life that enables that person to show up every day.
273
Mark MacLeod retweeted
Protect a little energy for the things you care about. Leave a gap between appointments. Get outside. Make time for a meal away from the desk. Filling every minute is not the same as using the day well.
1
3
326
Are today's 3 priorities in your calendar? If not, they won't happen.
273
Losing your clarity by 3pm every day is a recovery problem, masked as a productivity problem.
2
314
Most founders can tell you their revenue growth rate to the decimal. Almost none can tell you their energy trend over the last 90 days. Limitless members now have an app to track this every day. Your energy drives the numbers you actually track.
1
2
239
How athletes prepare for the biggest match of the year: Rest the day before. Fuel the body on purpose. Show up with a clear head. Compete, then recover again. Most CEOs skip straight to competing. Then they wonder why they don't deliver.
3
309
Your health is more important than your company.
1
6
371
Great analysis!
The Oura IPO is a great example of how venture fund math works. Forerunner led Oura’s ~$29M Series B in 2020. Those shares sit in its Fund IV vehicles, with the flagship fund being just $360M. Fast forward six years: Forerunner owns 28.7M shares, or 9.3% of Oura, and is selling its ENTIRE remaining position in the IPO. At the $42 midpoint, that’s ~$1.2B of liquidity, after already selling $65M back to Oura earlier this year. The main Fund IV entity owns ~88% of the position, so one investment could return roughly $1.1B+ to a $360M fund. Very roughly, that’s 3x+ the entire fund gross and potentially ~2.5x net DPI to LPs after carry from Oura alone. That makes selling a lot easier to understand. The funding history is also pretty wild: 2014/15: ~$2.4M Seed — Lifeline 2016-19: ~$17M Series A — David Shuman 2020: ~$29M Series B — Forerunner 2021: ~$255M Series C — Bedford Ridge 2024: $200M Series D — Fidelity/Dexcom 2025: ~$908M Series E — Fidelity led 2026: IPO at $40-$44/share What’s interesting is who is selling. Forerunner: selling 100% Lifeline: taking hundreds of millions in liquidity but keeping a position Fidelity: selling 0 Bedford Ridge: selling 0 And 73% of the base IPO itself is secondary shares. Existing shareholders are selling ~$1.5B at the midpoint, with Forerunner accounting for ~$1.2B of it. You can look at Forerunner selling everything and wonder what that says about future upside. But from a venture perspective, the math is pretty simple. If one investment can return ~3x your entire fund in cash, you take the DPI. Could Oura be worth $30B or $50B someday? Sure. But VCs ultimately get paid to return money to LPs, not hold paper gains forever.
1
585