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March 10, 2026
Hyperbolic Founders
I’m watching a favorite anime with my kids. Obviously had to turn it into a startup analogy....
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Real stories and hard-won lessons from the startup trenches. Learn what works, what doesn't, and how to navigate the founder journey.
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January 29, 2026
Swords and teacups
If you walk into our family home, you’ll see a set of shelves that hold swords and teacups....
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January 20, 2026
How (Not) to Newsletter
Quick update on the future of the How (Not) to Founder newsletter, including a new name and adjusted focus....
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November 12, 2025
The Skip Button Is a Trap
The real danger isn’t AI, it’s our impulse to skip the work...
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September 2, 2025
Princess Ride or Die
Our fintech startup had survived a broke Christmas, launched on a fancy stage, and now had some revenue coming in....
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August 6, 2025
Crashing Cannes to Save My Startup
I’m on a triple-decker yacht in the South of France, dressed to fit in while servers offer champagne and caviar. No one knows I'm broke!...
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June 9, 2025
Scouting Reports vs Funding Decks
This week, a basketball player recently rated the “most overrated” by NBA peers led his 4th-seeded team into the NBA finals and took an improbable game 1 victory from the jaws of defeat....
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April 16, 2025
7 things you should know about a potential co-founder
I was fortunate teaming up with my first co-founder. Here are seven areas (with actual questions to ask) I would dig into before teaming up with a co-founder again....
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March 19, 2025
How the tech do you build a roadmap in 2025?
Trends to watch, and a practical exercise for determining how to ship product efficiently in an AI world...
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February 24, 2025
Beyond the Scorecard: The Story You Own Shapes Your Leadership
My wife and I have four young kids at home, so I get to see a broad range of human behaviors and emotions every day....
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February 6, 2025
If Referrals are Gold, Then Partnerships are Fool's Gold for Early Stage Startups
I recently mentioned that attempting partnerships was one of the 7 tactics I employed to avoid real sales effort while building my proptech startup, and I think that deserves some clarification....
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January 16, 2025
Why Good Strategy Takes Time to Measure—On the Court and in Business
This past Fall, my wife and I coached our children in youth sports. That and lasagna taught me a valuable leadership lesson....
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January 14, 2025
7 ways I avoided founder-led sales, and which ones (didn't) work
It was a big warehouse in Brooklyn with hundreds of startup booths inside. I ran into one of my own angel investors. What he told me next stuck with me....
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December 30, 2024
What would you do if you knew you had 3000 weeks left to live?
How I'm learning to prioritize time and projects with my mortality in mind....
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December 16, 2024
How (not) to grow your startup: optimize the wrong thing
Focusing on what you like to do instead of attacking your growth bottleneck can distract you to death...
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November 29, 2024
How (not) to find your marketing groove
Shouting about features doesn't help your message resonate with users....
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November 11, 2024
How (Not) to Launch a Startup
Coverage vs Crushies...
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September 27, 2024
No One Will See the Founder’s Full Vision, and That’s OK
It was a 20-minute time slot with a strict cutoff to move to the next investor speed meeting....
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September 9, 2024
How (not) to Win as a Founder: Holding Bad Expectations
Holding bad expectations hurts you... a lot more than what happens to you from the outside...
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