My Failure Resume
Everyone publishes the wins. This is the other list — the ventures, investments, pitches and projects that didn't work, and the lesson each one left behind.
Things that didn't work
- 2014Content
First content channel — abandoned
Launched a motivational YouTube channel in college. Posted for months. Audience stayed flat.
Lesson: Don't copy a format you admire — find an angle only you can own. The channel failed because nothing about it was specifically mine.
- 2017Ventures
Early D2C experiment — shut down
Tested a consumer product line under the family manufacturing umbrella. Margins worked on paper, distribution didn't.
Lesson: Manufacturing strength is not a distribution moat. Owning the factory means nothing if you can't get the product to the shelf the customer is already standing in front of.
- 2019Speaking
Speaker bureau pitch — rejected
Pitched a structured corporate speaking circuit before the audience numbers justified the fee. Most decks went unanswered.
Lesson: Pricing precedes positioning only if the proof is already there. Build the proof in public first; the inbound replaces the cold pitch.
- 2020Podcast
Podcast v1 — quiet failure
Started a short-form interview show before Figuring Out. Twelve episodes, modest reach, never found a loop.
Lesson: Long-form works when the conversation is allowed to breathe. Cutting to 15 minutes killed the only thing the format had going for it.
- 2021Investing
Investments that didn't return
Multiple early cheques into companies that ran out of runway, pivoted away from the original thesis, or shut down quietly.
Lesson: A great founder pitch in a meeting is not the same as a great founder under pressure. Reference the operators, not just the deck.
- 2022Brand
A brand collaboration I should have walked away from
Took on a paid collaboration that didn't fit the audience. Engagement tanked, trust took a hit.
Lesson: Money is the easiest yes and the most expensive one. The audience pays attention to who you stand next to, every time.
Why publish this?
Because the highlight reel lies. Every founder I admire has a list twice as long as this one — they just don't publish it. The point isn't to celebrate failure; it's to make the lesson cheap enough for the next person to learn without paying for it again.
Hear founders unpack theirs on Figuring Out