How to fail at starting a startup


  • Solo founder + first venture, full-time, technical background
  • ~1 year of runway
  • Operating for ~3 months, no real product + users, still largely operating in the idea generation + validation phase
  • 2 years of work experience at a SaaS startup (Vanta) going from < 10 employees — 80 employees
  • Graduated from Brown University
  • Worst outcome is to live with my parents, and find some job at a FANG/equivalent company

Building or getting to a working product sucks for early learning, but is worthwhile to feel excited.

Only build when that’s what’s required to validate a hypothesis. After working on Passionfruit and Starview in a pretty significant capacity, I think that in all cases, building a working product is something that has not helped me validate my most critical hypotheses in any real capacity. Oftentimes, I think that I need to build a working product in order to get my foot in the door, but I should try to opt for easier ways to get there i.e. ask to interview them for some piece of writing.

What’s worth building during idea validation?

I’m finding that what’s worth building is to build just enough so that someone can understand when they would use your product and for what purpose. This could just be a sentence like: “Pay per view for Netflix shows,” or some clear UI/UX mockups for something more unfamiliar. The gut check I’m going to be working with is:

How do I know if I’m on track?

At this stage when I don’t have invested users, simple gut checks have turned out to be fairly high signal. What’s helpful for me is keeping something that’s easy for me to assess quickly and clearly. More specifically, I’m operating on two “sheesh” metrics (call them whatever you want, but “sheesh” is the best thing that’s come out of me “researching” TikTok):

  • Am I “sheeshing” when I work on this idea each day?
  • How often are the people I share this with “sheeshing”?

Grit, focusing on the work, and focusing on focus

Each time that I’ve found myself facing some significant lack of response from my peers or my cold outreach, or I was just feeling like I wasn’t moving as quickly as I’d wanted, man has it sucked. Not only because I wasn’t getting the results I’d wanted, but because I’d want to continue doing that work even less. The more I got caught up in “why don’t people respond” — the more I’d tend to try to shy away from reaching out more, and think about what else I should be doing. This usually is good — reflect on what’s not working so you can iterate. The problem arises when mental wavering and low morale gets in the way of getting the work that needs to be done, done. When approaching cold outreach, I have to internalize that it’s a numbers game. When I suck at Figma, I need to roll with the punches. When I’ve made a well-reasoned plan for what I need to do, and how much effort it will take to pay off, I need to have the grit to believe in the plan and execute. If there isn’t significant new information that clearly changes how my plan will play out, stay focused on the work. Stay focused on focus. Here’s one checklist I’ve put together to help:

  • Do I need internet?
  • Do I need to be at home?
  • Do I need my computer?
  • Do I need my phone?

Hodgepodge of things I want to keep written down and aren’t clearly contextualized. Blabla grains of salt.

  1. Be disciplined and rigorous about walking through the foundations of what I’m putting together. Make the 1 pager. Write down a few critical hypotheses and then get going talking to folks.
  2. Really cheaply go through and interview people who I suspect might have the problem that I am interested in — when they’re people I know. Just DM them quickly!
  3. When evaluating ideas, another point to evaluate is how quickly can I validate hypotheses around it? What’s my access to the people who have these problems?
  4. I’m pretty freaking slow at testing and validating hypotheses so far. I should weigh my ability to validate hypotheses/access to the right audience significantly. Access to this = distribution = feedback = progress.
  5. Hypothesis based approach is really powerful! Stay focused on this.
  6. Go through a socratic method on WHY I think things should be the way they are, or will get me to where I need to go. Think about why not and be my own devil’s advocate.
  7. Sitting and thinking a lot has usually been my best friend. It’s hard to feel like there’s a right time to do this though meaningfully. You have to gather critical thought mass, where you think something is working well or not working well to make the most of this. I think a regular check in where you do some light version of this, that may reveal that I should do a heavier version of this — where I’m naturally more unsure, and naturally having more thoughts running wild — is reasonable.
  8. Know that focus and capacity for “hard work” are seriously limited.
  9. Don’t underestimate how hard it is to deliver something valuable. Even incremental value requires work. It doesn’t mean it has to take a lot of time though — just don’t think it’s easy.
  10. Twitter is poo. Spending time here is not worthwhile.
  11. Iterate on a 1 week time scale. Believe in myself and believe in the work. Thrashing around too much on a shorter than 1 week time scale makes for not a lot of work getting done so that there’s a very low probability that any of it will be meaningful.

Memory garden

Hodgepodge of documents that I’ve been using

A few thousand words



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Christopher Chen

Christopher Chen

1. Tech. Maybe it's stockholm syndrome, but coding is fun. 2. People. What makes you tick? 3. China + East Asia. What freakin' cool place.