11 Startup Lessons Learned Building 3 Companies in 5 Years

Here's a look at some of the bigger epiphanies that have changed how I think about startups and life.

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I’ve started three completely different companies in the past five years: BlogDash, Feast and CMX Media. Each one has taught me a great deal. I’ve learned a lot about myself, about building a company, about other people, and about the world. When exploring and moving quickly through new terrain, we often don’t stop to look back at what we’ve learned. Here’s a look at some of the bigger epiphanies that have changed how I think about startups and life:


  1. You don’t have to raise money.

    There is this unspoken belief in the Valley that in order to build a successful company, you need to raise money and grow it to massive scale. That’s just not true. Many companies have been able to build massive scale without raising money, either by being scrappy or by building revenue-first companies. For instance, we haven’t had to raise money for CMX because we started with a product that makes it organically (e.g. conferences).

    If everyone is trying to build something massive, who’s going to take care of the smaller problems — the problems that are very real, but may not have a massive market size? Build what you believe in. If it happens to be something that needs investment, then great — raise money. If it’s not, that’s okay. Don’t build something to raise money. That’s a backward mentality. Almost every major business started with something very small and focused.

  2. You can ignore most advice.

    Other entrepreneurs love to give advice, but many usually aren’t very good at it. People don’t want to give bad advice. It’s just that they often don’t have enough context to really understand your problem. What’s worse than taking advice from any entrepreneur is taking advice from most investors. Whenever I speak to investors, they tell me what I need to do in order to succeed, which is usually for their benefit only. They’ll tell you what you need to do in order to be worthy of their investment. This may or may not be in line with what you believe in.

    Of course, there are some investors and entrepreneurs who give great advice. From my experience, they’re the exceptions. What makes them great is that they ask a lot of questions and help you come to your own conclusion. Just remember, no one knows your team and your business as well as you do. Use advice as a source of inspiration or new perspective, but never let it drive your direction. That decision has to come from you and your team.

  3. The worst-case scenario is better than you think.

    Most entrepreneurs fear they are taking on more risk than they actually are; never really address worst-case scenarios. Instead, they remain this dark, ominous concept looming in the back of our minds. Is our company is going to fail? Are we are going to be broke — living on the street, ashamed, ridiculed and depressed? It feels like a nightmare and it can prevent you from really going for what you want. But when you actually think about your options, you will realize that you have a much better worst-case scenario that you might think.

    If your company fails, you can get a job (entrepreneurs are actually employable), live with a friend or family while you get back on your feet, try a unique profession like working on a farm or working at a library, travel on an extreme budget, consult, join a friend’s company, etc. There are so many options, all of which are far from the depressing end you might imagine if you don’t address the idea of your worst-case scenario.

  4. Do what you believe in.

    Do you believe in what you’re doing? This is the single most important question for any entrepreneur. If the answer is no, nothing else matters. If the answer is yes, then nothing should stop you from moving forward. As long as you believe in what you’re doing, you stand a chance of defying the odds and succeeding.

  5. Don’t compare yourself to others.

    I’ve made the mistake of looking too much to competitors to guide certain decisions. It’s easy to get so caught up in the success and failure of other companies, and it can really mess with your emotions. Their success is not your failure. And even if it were, success itself is relative. People define success in a number of ways. So don’t get caught up in what other startups are doing. Focus on what’s in front of you. The only thing that matters is executing on your vision.

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