Startup Lessons Growing from 10 to 100

As I approach my final days at PlayHaven, I’ve spent a bit of time reflecting on the mistakes I’ve made and lessons learned since joining the startup three years ago. I’m incredibly fortunate to have been a part of the journey. There were layoffs, heated debates over company vision, and other dramatic events worthy of a separate blog post (or two). But in the end, we found success, growing from a team of 10 to 100 since I joined.

Inspired by Sam Altman’s Startup Advice essay, here’s advice I wish I had three years ago.

IMPORTANT: I jotted these down between commutes from my apartment to the office. As with anything I write, take my advice with healthy skepticism. It’s all about context and admittedly these quick notes lack much of that. This record of learnings is written for myself more than anyone else. If you have specific questions or would like to swap stories, don’t hesitate to send me an email ( or ping me on Twitter (@rrhoover).

  1. Don’t be so clever. Obvious is usually the better product decision. (tweet this)

  2. Have a vision and thesis of the future but don’t overshoot the market, ignoring what people ask for today. (tweet this)

  3. Error on over-communication (easier said than done). (tweet this)

  4. There will always be low hanging fruit but the ripest is often further away, harder to reach and see. (tweet this)

  5. Product complexity isn’t just a technical burden but an education hurdle for customers and new hires. Just because it’s easy to implement doesn’t mean it isn’t costly. (tweet this)

  6. Recognize we have a bias for hiring people like ourselves. Diversity is good. (tweet this)

  7. Hire people that intimidate you. (tweet this)

  8. Make ownership and responsibilities clear. (tweet this)

  9. Build a culture of accountability. (tweet this)

  10. Not every decisions can or needs to be defended with data. (tweet this)

  11. Intuition is underrated. (tweet this)

  12. It’s natural to feel under-qualified, in over your head in startups. That may be true but also recognize the Impostor Syndrome. It’s generally better to be overconfident than under confident. (tweet this)

  13. Momentum is key. Stagnation of innovation and constant negativity is draining and demoralizing. (tweet this)

  14. State the obvious, especially if it’s uncomfortable. (tweet this)

  15. Sometimes it’s ok (and unavoidable) to accumulate tech debt but make it a strategic decision, not a surprise. (tweet this)

  16. Fire quickly. There’s a reason this advice has become cliche. (tweet this)

  17. Who you hire ultimately defines your culture. (tweet this)

  18. The people that got you to phase A may not be the right people for phase B. (tweet this)

  19. Heroes - team members that do most if the work and hold most of the knowledge in a particular domain - are amazing and a huge liability. Heroes don’t scale. (tweet this)

  20. Have fun but maintain a sense of urgency and thirst. (tweet this)

  21. Celebrate awesomeness all the time. Especially the small things. (tweet this)

  22. It’s far better to be vocal and controversial than quiet and safe. (tweet this)

  23. The last 5% often makes all the difference. Follow through. (tweet this)

  24. Timing can be your best friend or worst enemy. (tweet this)

  25. Engage and include engineering very early in the product design process. (tweet this)

  26. In the words of Kanye, “Everything I’m not, made me everything I am.” If you’re saying “no” infrequently, you’re probably making bad product decisions. (tweet this)

  27. Product design and usability is important for any product. B2B companies don’t get a pass. They serve people too. (tweet this)

  28. Stay positive. Negativity is a cancer that will spread. (tweet this)

  29. Stop hating on competitors. Learn from them. (tweet this)

  30. Do “shitty” work. We naturally tend to prioritize the things we like to do over the things we should do. (tweet this)

This essay is a part of this week’s Startup Edition topic, “What lessons have you learned building your startup?” Read responses from other entrepreneurs at Startup Edition.

Subscribe to my blog for more essays on startups, product design, and personal growth.

Photo credit: quinn.anya


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