Co-Founder Conflict & Why I Quit my Startup | How to Fix a Dying Company | Founder’s Journey: Ep.2

Key ideas

Using his resignation from his first startup, Tan argues co-founders can fail through too little conflict as well as too much, and gives a remedy for each.

From a machine transcript of the audio. Quotes link to the moment they are said.

1. 1

   Too little conflict can also kill you

   Tan says he and his co-founder were friends for years, yet stopped spending time together to avoid conflict just as growth flatlined. He blames himself for giving way on product, personnel and strategy in order to look like a good co-founder, and says resentment grew until he could not sleep or eat. He treats keeping contact to a minimum as a warning sign, and says he resigned at the end of 2010.

2. 2

   Stay in the room until it resolves

   For founders who avoid conflict, Tan advises refusing to end a disagreement without a resolution, even if that means cancelling a weekend or going on a retreat. He says some of the best founders he knows did this. He also urges erring toward giving more feedback, and making sure you are heard when you have a point.

3. 3

   Too much conflict usually means unclear roles

   Tan lists the signs of too much conflict: factions, horse trading, long acrimonious meetings and decisions reopened again and again. He says this usually means nobody knows who owns what. He cites Heroku's founders, who he recalls listed every company task and gave each one owner, who gathers feedback and makes the call while others disagree and commit.

4. 4

   Listen well enough to state their case

   When conflict feels fundamental, Tan says the loudest person should not automatically win and suggests repeating back the strongest version of the other side's argument. He cites a thread by Shreyas Doshi on why listening is hard, and admits he is bad at it himself, especially when he hears things that go against his convictions.

5. 5

   Bring in outside help early

   Tan advises talking to other founders, friends and executive coaches, and involving your board, investors and advisors despite the embarrassment. He says third-party help can save a startup at an intractable point, and that wrong decisions can cost you the company, so this is no place to cheap out. He names Torch, which he discloses he funded at Initialized and which was founded by his own first coach.

In Garry’s words

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