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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  1. Competitors can become friends.

    Startups change frequently. Someone you consider a direct competitor can one day become a great partner. A great partner can one day become a competitor. The best thing you can do is treat everyone you meet with respect and be helpful to competitors and partners alike.

  2. Create space for honest reflection.

    It’s easy to have your head down for long periods of time and never come up for air, talk to your team or see the bigger picture. When I was working on Feast, my co-founder Nadia Eghbal and I often worked remotely. We made it a habit to meet every week just to talk. We shared our feelings and our fears. We gave each other brutally honest feedback. We talked about the direction the company was moving and whether or not it felt right.

    The hardest and most important decisions we made for Feast came from those talks. They led to some of the most successful strides and always left us with greater business clarity. If you can do it in person, then leave the office, go for a walk, or sit in a park. Create physical, mental and emotional space where you can have an open and honest conversation.

  3. Ask customers to pay as soon as possible.

    If you plan on selling a product, it’s never too soon to ask customers to pay. It’s too easy to continue building great things while gaining an audience and delaying the uncomfortable task of asking for money. But you must do it. It’s the only way you will really know if your business is real. If you ask for money, people will either say yes or no. If they decline, you can learn what you really need to build in order to solve a problem worth paying for.

  4. Grow your culture organically.

    I used to try to think strategically about what a healthy company culture would look like for the companies I started. I’ve since learned that great cultures form on their own. They aren’t planned. They start with the founders and translate to the team. You can find culture in everything from the subtle interactions and habits that form amongst the team. I think that’s why it’s difficult to develop a real culture when you hire too many people right away. As a result, the company will try to manufacture a culture instead of growing one naturally.

  5. You have to take care of yourself in order to succeed.

    The startup world is so focused on speed. You work hard for long hours and you work late. You might fail, but it certainly won’t be due to a lack of hustle. That’s all good and commendable, but I’ve found it to be completely unsustainable and inefficient.

    There are some really successful people who are workaholics. But there are also a lot of really successful people who build daily routines so they can take time for themselves and their families. They ensure they’re emotionally, mentally and physically healthy. If you want to help the world, you have to help yourself first. For instance, at CMX we encourage members of our team to travel, work on their own schedule, and build their daily routine around what will make them healthiest and most productive.

  6. Learn from personal experience.

    You won’t truly understand what I’m sharing until you experience it yourself. So, if you take one thing away from these lessons it should be this: continue to experiment. Put yourself in uncomfortable positions. Take risks. If you don’t know anything about fundraising but you think you need to do it, just start. You’ll learn quickly. Just take that first step and you’ll learn along the way.

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This article has been edited and condensed.

David Spinks is the CEO of CMX Media, hosts of CMXSummit and CMXHub, the world’s largest conference and online publication for the community industry. A version of this post originally appeared on the author’s blog. Connect with @DavidSpinks on Twitter.

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