1. Founder, Round 2Back in the arena
   • Pick a vertical with real tailwinds (AI infra, fintech, defense)
   • Assemble a small founding team, raise a seed
2. Exec, AI Growth Co.Product, etc
   • Join a rocketship as CPO/CTO at growth stage
   • Learn from someone else's playbook for a few years
3. VCValue-add, obvs
   • Go back to the investing side with operator cred
   • Focus on seed/Series A in AI + fintech
4. Lifestyle Co.Niche but nice
   • Build something profitable, keep it small
   • Optimize for freedom over scale
5. HoldCoCliché AI rollups
   • Acquire 3-5 niche SaaS products
   • Apply AI automation to expand margins
6. Wild CardSomething completely different
   • This is a much longer bullet point that should wrap to a second line to test whether the wrapped text aligns correctly with the start of the text on the first line, rather than going all the way back to the bullet marker
   • Another long sub-bullet to make sure the text wrapping behavior is consistent across multiple items — if this second line starts under the bullet instead of under the text, we have an alignment issue that needs to be fixed in the CSS

After selling Commonstock to Yahoo Finance in 2023, I spent 18 months doing absolutely nothing productive. Traveled, played a lot of golf, and convinced myself I was “recharging.” In reality I was just avoiding the question: what do I actually want to build next?

The Honest Assessment

The truth is that founding a company from zero is the only thing that's ever made me feel fully alive. The early days of Commonstock — shipping features at 2am, watching the first users trickle in, the terror of running out of runway — that was the best professional experience of my life. Everything else has felt like a compromise.

The best time to start a company was 10 years ago. The second best time is now.

What I've Learned

A few hard-won lessons from the Commonstock journey that I'll carry forward:

• Distribution beats product. We built an incredible product that nobody could find. Next time, distribution strategy comes first.
• Raise less, keep more. $40M raised sounds impressive until you realize how much dilution that represents. Bootstrap as long as possible.
• Pick a market with paying customers. Social networks monetize through ads. That's a terrible business for a startup. Next time: SaaS or transactions.
• Nested complexity matters. Sometimes the details have their own details:
  • Revenue model validation before product-market fit
  • Unit economics at every stage:
    • CAC payback under 6 months
    • LTV:CAC ratio above 3:1
    • Gross margins above 70%

The Technical Side

I've been writing a lot of code over the past year. Here's a quick example of the kind of thing I'm building — a simple API call using fetch:

const response = await fetch('/api/portfolio', {
  headers: { Authorization: `Bearer ${token}` },
})
const data = await response.json()
console.log(data.positions)

The positions array contains each holding with ticker, shares, and avgCost fields. Simple but effective.

More to come. For now, read the full breakdown on my site or check out the project roadmap for what's next.