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put your oxygen mask on first
The worst day of my entrepreneurship career was laying off the team of my failed startup.
In a moment of post-mortem reflection, I realized the horrific irony. Had I simply taken care of myself first, I could have prevented hurting the rest of the team.
Because if you don’t take care of yourself first, it’s easy to suffocate while trying to help everyone around you.
Side note: this is a bit of an insane topic to write about as I’m about to board an international flight but yolo.
Over the past decade I’ve had the misfortune of building multiple companies at once. It sounds impressive, but it’s a curse.
There’s a saying in start-ups: starting a company is like throwing the pieces of an airplane off a cliff and assembling it on the way down (another airplane analogy - nice).
If that wasn’t challenging enough, at my previous start-up we threw all the parts off the cliff -except we didn’t even have a complete plane in the mix. We had parts from four different planes, and as we plummeted, we scrambled between the four piles trying to build them all at once.
Spoiler: none were a success.
Even worse, we had real early traction with 1 of the 4 projects, but figured there were greater riches elsewhere and lost all focus. The core idea (helping business owners sell their business more easily) was the winner, and it’s what we do at Breakwater today. But it conflicted with another one of our projects, so instead of doubling down, we kept reinventing the wheel and launching new ideas.
The team felt it worst. They were constantly whipped into new ideas and new directions, never given the chance to master their craft. How frustrating.
It’s the same as fad diets and workout trends. Everyone gets excited by the new idea, but not by the strategy that actually works: doing the thing with traction, every day, for decades.
The greatest form of self-improvement is compounding daily discipline across a lifetime. But there’s a strange paradox in how entrepreneurs relate to discipline. On one hand, we’re some of the hardest working people alive, with decades of sacrifice to show for it. On the other, shiny object syndrome makes us incapable of focusing on the ‘boring stuff’ that actually drives success.
So put your own mask on first. Protect your health, your focus, and the one plane worth building. You can’t help anyone if you’re the one gasping for air.
idea of the week 💡
Credit: ideabrowser.com
Winpick — the launch and distribution service for indie Windows tools
Problem: solo Windows developers build the tools power users love (think: a clipboard manager that beats the paid one), then hit a discovery wall. GitHub pulls stars but not one paying user, a Reddit post dies inside an hour, and direct downloads trip a SmartScreen warning that kills trust on sight. The Microsoft Store lists ten thousand tools and surfaces none — a good app drowns beside dead ones.
Idea: a curated first-customer channel. Winpick hand-reviews each submission on a clean machine, publishes a demo page with an install walkthrough and a plain-English description, and sends three to five vetted tools per week to IT admins and power users who actually pay for Windows software. Curation is the product.
How it works (wedge): hand-pick twenty solid tools from GitHub, indie forums, and Show HN. Test each on a fresh Windows install and write plain descriptions. Launch the newsletter on Beehiiv, seeding subscribers from r/Windows11, r/sysadmin, and power-user forums. Run the first issues free, then charge for a featured spot once open rates hold.
How it makes money: $99 buys a developer a launch package with a listing and a written review, $10/month keeps them visible between launches, and a 10% cut on each sale Winpick sends ties revenue straight to a developer's real outcome.
Why it might fail: trust is the whole business. It takes months to earn and one bad pick undoes ten good ones. Monetization from a small developer supply side is unproven, and the editorial workload doesn't scale without diluting the very curation that makes it valuable.
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workouts this week
at-home
16-minute AMRAP:
10 burpees
15 air squats
10 push-ups
40-second wall sit
gym
Strength + conditioning. 5 rounds:
Front squat: 5 reps (moderate-heavy)
Incline dumbbell press: 10 reps
Barbell row: 8 reps
Ski erg or assault bike: 45 seconds hard
Rest 2 minutes between rounds.
outdoors
10-minute easy jog (warm-up)
8 rounds: 30-second sprint, 90-second walk (recover)
10-minute walk (cool-down)
new videos on youtube
I am back to (try) and post more regularly on YouTube focused on buying & selling businesses. If that's of interest, make sure to subscribe:
tweet of the week
Moses Kagan on the tunnel you enter at ~15 that shoots you out at ~35 — and how much of the rest of your life is determined by the choices you make (and the luck you have) inside it.
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every second counts