Cofounder Twiage, participant Blueprint Health class of 2014, MassChallenge 2014, Village Capital 2014
Cofounder ROAM Data, acquired by Ingenico 2012
Cofounder Radius Partners, acquired by Fundtech 1995
I've been technical cofounder at multiple ventures, some successful, some not and built startups from concept to acquisition. Made all the mistakes and invented some new ones.
Serial technical cofounder with exits, acqui-hires and flameouts. Done no-process, waterfall and Scrum. Built teams from 1 (me) to 20 people. Made all the mistakes, invented some new ones. Blunt to a fault.
Been through Blueprint Health, MassChallenge and Village Capital accelerators as cofounder.
I've been involved with a couple of chapter 7s and chapter 11. There is not enough money in the world to make me consider touching one. Just off the top of my head:
1. If a company's already run into bankruptcy then you're not joining as a co-founder, no matter what anyone says.
2. Bankruptcy makes enemies. Join as a C-level and you inherit those enemies.
3. The debts discharged in bankruptcy are only the most obvious 'debts' owed by this entity. Technical debt, management debt, favors owed ... all this stuff becomes your problem the minute you sign on.
4. Everyone still associated with this venture, formally or informally is trying to recover sunk cost. Startup failures, at the end, are a swirling mass of schemes and every individual player sees himself and his scheme as the center of the company's resurgence.
5. The more compelling the original vision of the company, the worse all the other problems it has will be. Why? The vision is what keeps the swirling mass of recovery schemes going. So your in-depth research validating the original vision is actually a HUGE red flag because it guarantees that all the other players trying to make something of this mess will never give up.
My advice? Find the nugget of good this mess will spawn and attach yourself to that. Start with the people. Who are the quality people here, the ones who've done the right thing in difficult circumstances. Cross off the list anyone who's still participating in the recovery schemes. The smart ones cut their losses cleanly. Find out where they're going and follow them.