2/ Sometimes they fail because they were poor matches to begin with. - Values mismatch: e.g. One never wants to sell, another wants to sell early. - Skills mismatch: e.g One scales as the co grows, the other was only helpful in the beginning.
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3/ Other times it’s because they had different expectations and never had the tough conversations early. Admittedly, these differences are difficult to assess. Until you are faced with a truly challenging decision, you may not be able to understand where/how you disagree.
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4/ To combat: Talk early and often about: - What success looks like (outcomes, culture, roles) - What are non-negotiables - Who’s in charge in case of disagreement. On this last point: Make sure there is a clear CEO / tie-breaker. Not having one is a red flag IMO.
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5/ Other times they’re aligned and complement each other, they just can’t work together - Different work-styles - Different communication styles - Conflict breeds more conflict or distance, instead of addressing concerns and bouncing back.
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6/ Cofounder relationships are like marriages, and should be treated as such -- something you have to work at consistently. - Read relationships/communication books (eg Nonviolent Communication & Gottman) - See a coach for both of you - Date first and don’t do a shot-gun wedding
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7/ Some general principles: - Don’t assume intent or have contempt - Rescript + see with fresh eyes - Refrain from passive-aggressiveness - Have an individual coach or someone else to vent to. - Proactively communicate concerns. - Make + keep commitments - Honor when not present
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8/ You don’t need to be best friends. (Or even friends at all.) You need to respect & trust each other, communicate effectively, and work well together in accomplishing company goals. And not hate going to work every day.
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9/ For all the people in crippling cofounder relationships out there, all the best to you. Hope you have someone to talk about it with. Someone not in tech, like a therapist or coach, because you want to respect everyone's privacy.
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10/ If you have a bad break up, try to leave on as good terms as you can. You want to honor the sweat you put in together, and, more practically, you will forever be a reference for that person, so, at the least, its worth coming to some prisoners dilemma-like understanding.
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11/ Co-founder struggles are where integrity is tested + where character is built. How you handle it will show to teammates & investors how you’ll handle everything else. Be charitable+compassionate yet resolved, not dismissive + bitter + indecisive. You’ll also be happier.
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12/ Something of a (non-comprehensive) litmus test for choosing a co-founder: “Pick a co-founder who you’d be OK breaking up with.”
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