I grow people and businesses.
I led M&A for a billion-dollar company, helped scale a bootstrapped business to the top of the Inc. 5000, and now run Outperform Ventures. This is where I write down what I've learned about business, investing and leadership.
One email a month. Unsubscribe anytime.
Answers in a few minutes
All toolsThe questions founders ask me most. Free, no sign-up, no email required.
- Exit Math
What would I take home?
Work out what lands in your pocket if you sell.Get your answer - Valuation
What is my company worth?
See the range a buyer or investor would likely pay.Get your answer - Idea Grader
Is my idea any good?
Score your idea on the things that predict whether it works.Get your answer - Raise or Bootstrap
Should I raise money?
Compare the real cost of outside money with growing on revenue.Get your answer - Founder Diagnostic
What's capping my growth?
Find the one constraint holding the business back.Get your answer - ICP Builder
Who is my ideal customer?
Define the customer you should be selling to first.Get your answer
Latest posts
All writingOct 22, 2026
What Are My Stock Options Worth?
Your stock options are only worth something if the company is. If it isn't growing fast and profitable, or on a real path to profit, your equity is likely worth zero. Spend less energy on strike prices and percentages and more on helping the company grow.
Oct 8, 2026
Where I'd Put Money Instead of the Anthropic IPO
Anthropic has built one of the fastest-growing companies ever. I'm still passing on the IPO. As models get cheaper, I think the money in AI moves to the businesses using it and the companies that own the physical side. My guess is the IPO lands after the November midterms.
Oct 4, 2026 · Update
AI Agents Are Shopping for Apartments
Renters now send AI agents to compare prices and book tours. Most property websites were built for people. That gap is why I invested in Multisites.ai.
Oct 3, 2026
Recurring Revenue Is About to Get a Lot Less Recurring
Recurring revenue works because people sign up on impulse and cancel on procrastination. AI agents remove the procrastination. Great products will grow faster because of it, and poor products will churn faster for the same reason.
Oct 1, 2026 · Update
Listen Labs Sold for 67x Revenue. Airtable Sold for 2.7x.
AI-native companies are valued on their data and their models, not their revenue. A database with a dated interface for humans is valued like what it is.
Sep 30, 2026
Your Identity Was Never What You Do for a Living
AI is changing every job title, including the CEO's. Your job title is what you do, and it will change. Your identity is who you've always been. I grow people and businesses, and AI changes how I do that.