Chewing on Failure

Over the past 18 months, I've supported numerous founders through the difficult reality of their startups not succeeding. I've noticed that when their startup fails, many founders often jump straight into the next thing—another company, a new job, a better pitch. But real learning comes from pausing, reflecting, and learning from it.

When meeting repeat founders, I always ask: "What's the biggest lesson you learned from your previous company?" For founders close to me who've experienced failure, I encourage open-ended reflection as a pathway to growth.

Recently, I realized my open-ended approach, while helpful, could be more structured. And so I built out two sets of prompts—one for the business, and another for you, the Founder and the human behind it. Think of this as a post-mortem, not just for your startup, but for the version of you who built it.

Part I: The Company Post Mortem

This section is for interrogating the business with honesty and precision. No fluff. Just signal.

1. Did we solve a problem that was real, urgent, and painful?

• Who really needed this?
• Did we validate the pain—or assume it?

2. Was the market ready—and was I right about timing?

• Did we show up too early? Too late?
• Were we building in-market, or in-theory?

3. Did our product create real value?

• What usage patterns proved we were essential?
• What signs did we misread as traction?

4. Was our go-to-market repeatable?

• Did we discover a scalable engine—or just hustle our way to early wins?
• When channels plateaued, did we adapt?

5. Did we use capital wisely?

• Was our burn rate justified by progress?
• What tradeoffs did we avoid making?

6. Did I build and lead the right team?

• Were the right people in the right roles?
• Did I cultivate clarity, ownership, and accountability?

Part II: The Founder Reflection

This one’s about you—the person who dreamed the dream, raised the money, led the team, and made the calls. The startup didn’t make it. But you’re still here. So ask:

1. What was I chasing—beyond the business?

• Was I building to solve something in the market, or something in myself?
• Where did my identity and the company start to blur?

2. When things got hard, how did I show up?

• Did I lead with courage, clarity, and care?
• Or did I avoid, delay, and rationalize?

3. What feedback did I ignore—and why?

• Was it ego? Insecurity? Hope?
• What was I afraid might be true?

4. What patterns in my decision-making need attention?

• Did I move too fast? Over-index on consensus? Avoid conflict?
• Where did I lead from fear instead of conviction?

5. What am I grieving—and what am I proud of?

• What hurts the most to lose?
• What do I want to remember about this chapter?

6. Who was I in this company—and who do I want to become next time?

• How did this experience change me?
• What will I carry forward—and what will I leave behind?

You don’t get better by moving on. You get better by looking back. These questions won’t fix what happened. But they might make you sharper, humbler, and more dangerous in the best way.