10 Lessons from 10 Years of Entrepreurship

Posted on January 10, 2022.
So much has happened and nothing (except my hat and my glasses) has changed. 🙂

This week, Jan 12, 2022 to be specific, is the 10 year anniversary of quitting my last full time job. On Jan 12, 2012 I walked out of my Director of UX gig at TheLadders in NYC into the riskiest professional move I’d made to that point. With 3 months’ of financial runway I launched a tiny product studio with Josh Seiden and Giff Constable. Since then I’ve built three businesses. Sold 1. Closed 1. And now I maintain the last one. Here are 10 things I’ve learned through 10 years of entrepreneurship:

  1. There’s no good time to become an entrepreneur. You’ll never know enough, do enough or save enough for it to feel like the right time. If it feels too safe, you’re not taking enough risk.

  2. Team above everything else. You could have the best idea. You could have infinite resources. But if you don’t have the right people around you it’s all for nothing. The people you choose to build with will determine your success. If you choose wisely, they’ll build with you again and again.

  3. Your partner’s support is foundational. On the personal side of entrepreneurship is our relationships. Your partners in life need to be onboard with your decision to build something. They don’t have to like it but without their understanding and support your focus will wander.

  4. There’s nothing wrong with building a “lifestyle business.” While others chase unicorns and their abysmally low success rates, some of us chase sustainable, long-term businesses. If we can build revenue engines that support a comfortable and balanced lifestyle, we’ve succeeded at the entrepreneurial game.

  5. Community will keep you sane. Entrepreneurship is often described as lonely. It doesn’t have to be. There’s a myriad of community options where like-employed (or unemployed?) folks share, learn, vent, laugh and grow together. If you can’t find one you like, start your own.

  6. It gets easier the second (and third) time around. Here’s the good news about the majority of humans: we learn from our mistakes. The first time I wrote a book it felt like a monumental task hobbled by misstep after misstep. The second time, things were smoother. By the third time I was self-publishing.

  7. Man, I love my own ideas. Despite decades of experience, working in, teaching and writing about testing hypotheses, I still love my ideas and find it incredibly hard to let them go. It never seems to get easier.

  8. You’ve been an entrepreneur before. If you’ve ever sold candy or cookies at primary school, been in a band, started a club or sports team, you’ve done this before. You’ve had an idea, sold it to others and brought them along on your journey. Lean into those experiences.

  9. Success can breed apathy. If your business finds product-market fit you start to grow. You’re a hit! What else do you need to learn? Besides who’s got time to learn when we can scale! Resist the urge to sit on your laurels. The world and the market move fast. So do your customers. Let your enthusiastic skepticism shine through.

  10. Work from abundance, not scarcity. Working from scarcity builds panic and stress into your life. Working from abundance relieves you of this anxiety allowing you to focus that energy on nurturing and building your business. Your next customer will come. They always do.

  11. (BONUS) You don’t always have to make hay while the sun is shining. You can just go outside and enjoy the sun for a bit. You’ll be happy that you did. 

I’d love to hear your best entrepreneurship lesson. What have you learned?

One thought on “10 Lessons from 10 Years of Entrepreurship

  1. Hi Jeff, just started as an entrepreneur, so not 10 lessons but here are mine so far:

    1. It is scary until you do it. Before you make the decision and really do it, it seems scary, exciting, all that stuff. Until you do it, and then it’s not. Then it just is.

    2. You’ll quickly experience your “new normal”. When you hang around other entrepreneurs and hear how they do things, what they get paid, etc. your idea of what is normal will shift, and that will become your new benchmark. And then you have to stretch yourself again for that new “new normal”.

    3. Why do you want to become an entrepreneur? When I started I immediately took a freelance job (for some steady cashflow). Then I found out it didn’t give me the type of creative energy I was looking for, so after 2 months I quit. Now I’m focussing on what gets my juices flowing.

    4. Talk, talk, talk. I’m talking with a lot of people who just became entrepreneurs or want to become one. Everybody’s experience is different but it is useful to learn from others. Also I’m throwing my ideas out there and see what people are interested in. That is something where I can provide value.

    5. Hmm I’ll have to share this in a few months time 😉

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