10 Lessons from 10 Years of Entrepreneurship

It's been 10 years since I quit my last full-time job. Here are 10 short lessons I've learned the hard way.

Hey folks --

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?

New on the blog:

3 Frequently Asked Questions about OKRs Regulated environments, multi-nationals and unclear leaders are 3 topics covered in detail in this blog post when it comes to setting proper goals.What is Agile? You can laud the idea and still be critical of the implementation. That is the true spirit of Agile. Here’s how I came around to this idea.

What I'm up to:

Season 2 of my podcast, Forever Employable Stories continues to put out episodes weekly in the new year. So much to learn from these super interesting folks from various walks of life.

What I'm liking at the moment:

Listen: About 1000 years ago I went to see a show at the legendary 9:30 Club in Washington DC. The opening band blew me away. They were called The Zutons and I listened to them on repeat for a year. And then I forgot about them. I recently re-discovered them and they still live up to the hype from that show all those years ago. Check them out.

Watch: The Expanse is back! Season 6 and it's back on as good as ever. This is one of the best sci-fi shows around. It's gritty, real and messy. I love it.

Read: If Then by Jill Lepore -- Just getting into this one so don't have a full review yet but this book details the early days of data collection and harvesting and how we ended up with the whole "if you're not paying, you're the product" word we live in now.

(FYI, I'm now booking into Q2 2022 since Q1 is completely booked.) As always, if you want me to work directly with your company on training, coaching or workshops on the topics of organizational agility, digital transformation, product discovery and agile leadership, don’t hesitate to reach out.

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