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My 15 lessons learned from a failed startup

​​Since shutting down my first startup, I’ve spent a solid amount of time analyzing what it means and feels like to fail. I’m hard on myself and I always have been. I love to win, I love competition, and I love success in any form. And man, do I hate being told I can’t do something.

The person I compete most against is myself. And for the first time in a long time, that relationship is a healthy one. Now I still try to avoid failure, but I also actively embrace it as a tool for change and improvement.
Had you talked to me when my first startup failed, however—well, you probably wouldn’t have. I avoided the topic and spent the first couple of weeks afterwards looking for a hole to crawl into to escape startup land.

​​Now, after several years and three other projects (which are all still running!), I’m at a place where I can recognize and talk about the lessons learned through the failures of building a startup. In doing so, I figured I’d create a list because who doesn’t love a good listicle? This is a culmination of the experiences myself and many others have had venturing on the same journey.

  • Building a product that solves an actual problem for a large group of people is half the battle. You’d be surprised by how many people are willing to get on board when your mission is to help.
  • Treat the small decisions the same way as you do big decisions.
  • People are meant to be lead, tasks are meant to be managed.
  • Bootstrapping is hard. You must have vicious focus on your target group, be willing to experiment, and understand that lean and frugal is key. But most important is knowing when and where to dump the cash.
  • You have to be able to have the tough conversations.
  • Hire slow, fire fast.
  • Celebrating wins, acknowledging and analyzing failures, quick recovery, and positive patterns are critical to growing/developing a culture.
  • Sometimes you’ll have to work late nights or on the weekend. This isn’t a badge of honor or something to celebrate, but still has to be done. If it becomes a pattern, that should call for some personal or company-wide analysis. One always impacts the other.
  • Figure out who your product’s community is, tap into it and build around it. Don't go haywire with paid advertisement until then.
  • There comes a point where you have to let it go, or let it drag. Letting it drag not only makes it worse for you, but seriously tarnishes the experience you work hard to continually provide for people using the product.
  • It probably didn’t have to be a meeting.
  • You don’t need to fundraise just because you’re a startup.
  • Holacracy, when done right, is much more conductive to a successful organization than hierarchy.
  • Remote work is equally tough and beneficial. Communication skills are forced and shaped, teams need to collaborate often, and people do work better with long intervals of uninterrupted, focused time. You'll be able to discern when a meeting is necessary, it will cost you less and increases output. This benefits the well-being of the entire team. Remote work with ~two on-sites annually is truly all you need. I’m at a point where you cannot convince me otherwise. Yes, I know this cannot work for all professions or teams. I wouldn't expect scientists to cure cancer from their house. But they technically could, so... Does it work for everyone? No. But most, yes. Good data point from Ryan Hoover’s twitter survey. 8,600+ votes is a solid enough.

  • You break it, you buy it. Make sure your pace allows you to hit goals in a healthy, efficient way that keeps you responsible for what you are creating. The world doesn’t need wrong answers in record time. Or another Facebook scandal. Realistically those all started as fast-moving, well-thought-out and unchallenged ideas which eventually became unnecessarily expensive. The Big Five can afford it—you as a startup cannot.

​​In my time building companies, growing as a leader, and most importantly honing my craft, I’ve learned lessons in business and on a personal level that have naturally benefited others. In just the last year alone, I’ve spoken with and had the opportunity to learn from some of the most profound individuals of our time. I’m forever grateful for this, and know that as long as I continually have a beginner’s [student] mindset, there is nothing myself or our team(s) can’t do.
Some of the points above are straightforward and very obvious, but others come with nuances and require fleshing out on their own. Post-first-startup, I now list challenges as they occur so I can write about them in more detail. I’ll be sure to grab these, along with the lessons written here and create specific blog posts for them.​​

​​Any points you’re interested in learning more about? Let me know! Until then, I’d love to know which you’d add (or remove) if you’ve ever been in the same boat. Let’s talk shop on Twitter @imcatnoone.

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