Learnings from Trestle  

From 2018-2019, I worked on Trestle, a company intranet product designed to help you find out who knows what inside your company. It was partly inspired by Stripe Home. After spinning down the product in 2019, I wrote a twitter thread about why it failed and my experience. I’ve copied the thread here for posterity

Trestle primarily suffered from a buyer/user mismatch. I still believe the problem I was solving is a huge opportunity - I had so many conversations with engineers, designers, salespeople, managers, etc. about how hard it is to figure out who knows what in large orgs.

As a directory, Trestle was only useful when it provided information about people across the org, so it was hard to avoid a top-down distribution strategy. HR was always a key stakeholder and unfortunately, we never solved a deep enough pain point for them.

A big lesson I learned was to focus on solving the weakest point of your company. I kept building cool features for users which didn’t move the needle with HR. You need to focus on getting the product into users’ hands first - it won’t matter if you make a great product if no one can use it.

Secondly, it’s brutal being a solo founder. Juggling building product, sales, investors, legal stuff, design, and managing your emotional state is pretty overwhelming. The amount of context switching also kills a lot of your momentum which is critical in the early days.

Thirdly, never rewrite your product. I thought if I could rewrite everything in React Native (including web), I would get a mobile app and be able to write once, run anywhere. The rewrite took months, killed momentum, and the unified codebase didn’t help future dev work

The mistakes listed above may seem familiar. They have all been made by others and the lessons I iterated have been repeated ad nauseam by YC, podcasts, medium articles, and other blogs like this one. This was a meta-failure on my part: I thought my situation was special and justified to myself why these lessons didn’t apply to Trestle. I’ve been seriously humbled by this experience and my hope is that others can learn from this without having to totally fail first.

As for what’s next for me - I’m excited to get back to work building something new! I’m exploring a few ideas that interest me. And who knows? Maybe I’ll revisit this problem someday :)


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Learnings from Comradery

From 2019-2020, I worked on Comradery, a community platform. After spinning down the product in 2020, I wrote a twitter thread about why it failed and my experience. I’ve copied the thread here for posterity. Comradery now lives on as an... Continue →