Working on a startup with best friends — the biggest mistake

September 15, 2022

Junior year at Stanford I cofounded a startup with two friends, Sarah, and Lainey. We had all committed to working on the startup that summer in lieu of an internship, but in May, Sarah said she wanted to do an internship and the startup at the same time.

Lainey and I felt that this was unfair because Sarah wouldn’t be able to contribute as much time and energy to the startup as us; after all, both the internship and startup were full-time. We tried compromising, saying that Sarah could work on both, but it would mean a lowering of her equity share, or that this summer wouldn’t count towards her 1-year vesting cliff we agreed on. However, Sarah refused and insisted that it would be fine and she could handle working on both at the same time.

This is where the first mistake occurred — instead of making the conversation about us and how we felt, we instead tried to prove that Sarah would not be able to handle working on both at the same time and convince her otherwise.

We pointed out her GitHub line contributions — since we were all coders — and showed her that since she had contributed less to the project than Lainey or I, we didn’t think she would be able to handle working on both the internship and the startup at the same time. After all, she was already contributing less than either of us even now, working on just the startup.

Our actions backfired immensely, because she didn’t see two coworkers trying to give her statistical proof about why her claim was false, she saw two friends telling her that she wasn’t good enough, and despite her best efforts, was still “worse” than both of them. At this point, she started crying and revealed that she had been recently diagnosed with ADHD. She had very low self-esteem and her whole life, it felt like she struggled more than everyone else at school, but her diagnosis didn’t feel validating. Instead, it felt like something that she now had to deal with on top of everything else. Her doctor said she could take medication to help, but she was scared to because her dad said when he tried it, he had horrible side effects.

This is where the second mistake occurred — instead of being purely empathetic and supportive, we also suggested that if she were concerned about the ADHD, it might be a good idea to give the medication a try.

Again, our actions backfired. Sarah did not see our words as the suggestions of two friends who cared for her wellbeing; for her, they felt pressuring and coercive.

Sarah was very hurt by how we handled the situation, and ended up doing the internship, leaving on bad terms. She later refused to give up the intellectual property of the parts she coded, meaning lawyers had to get involved. More importantly, I lost a close friend.

As for learnings, I think there are several things. In this specific context, a legally binding founder contract would be the obvious solution. We had actually agreed to a contract earlier, but because it wasn’t legally binding, Rachel brushed it aside. However, even though this would’ve helped the business, Sarah still would’ve left resentful and I still would’ve lost a friend.

So more importantly I think, we should have made the conversation about how we felt (i.e. “I don’t feel comfortable working with a cofounder who is also doing an internship because I need to — for example — have someone who will respond quickly during the day,”) instead of whether or not she was able to handle both. If she insists that she can do both and still respond quickly during the day, then we should have made a list of needs that both parties agree to, and an agreement that if these needs aren’t met then she needs to pick. Whereas our actions presumed that she wouldn’t be able to do it, this solution presumes trust. It says, “Hey we believe that you can do both. Here’s what it would look like to do both. Now you get to try to do both. Here’s what happens if you can’t do both.”

Additionally, I think there was a friend-business component that made communicating really difficult. I think it’s perfectly valid to discuss poor performance in a professional context, and talk about potential medical solutions as a friend, but these lines were constantly being blurred. I think what would’ve helped is more statements clarifying intentions: for example, “I don’t want to give you any medical advice. I do want to see you thrive and make choices that make you feel empowered.”

Finally, overall throughout the conversations, we should have focused on making her feel heard and supported. In hindsight it was clear that she was very insecure about her personal abilities and contribution, and needed our reassurance. By making her needs feel met, it would’ve been more likely that she would also be willing to meet our needs as well (like “I don’t feel comfortable working with a cofounder also doing an internship.”). Instead, we did the opposite, and made her feel even more insecure about herself, which in turn, made her even more defensive and combative.

So, key learnings: use I statements , clarify intentions, and focus on making both parties feel heard.

Maddie Wang founders of founders cafe solo founder
Maddie Wang
Gay / Solo-Founder / Stanford Dropout

I'm building Founders Cafe because as a solo founder, it can be very isolating. Last year, I lost 4 co-founders and a best friend on a previous startup.

Previously built a Minecraft Server ($61k), Amazon Store ($120k), and Queer Chart, where I met my girlfriend & close friends.

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