How Entrepreneurship Showed Me Love

Shawn Carolan
· 3 min read

One year after laying off team Handle (now back in business thanks to @kgellci) and six months after rejoining Menlo Ventures, I’ve taken heart in how much the experience taught me about company building, life, friends, family, myself, and even love. A token of my gratitude this Valentine’s Day.

To this former entrepreneur, proud to be back in venture capital, love is…

  • Napkin-sketching an idea to solve a problem you feel acutely every day, have thought about for years, and finally see an approach.
  • The support from your firm to move it forward, when they all know it will mean more work for them and that the odds are never in your favor.
  • Learning new things each day in a founder’s role you knew from afar, but find so different walking in the shoes.
  • The good wishes of a spouse who knows they and the kids will miss you in your 80 hour weeks, but want to support your dream. <sobbing begins>
  • The angels who believe in you and invest their hard-earned money to give you a shot at cracking an important but challenging problem, putting their faith in you.
  • The inner voice, who through tears, allows you to leave to pursue the dream, despite the costs, risks, and colleagues you are leaving behind.
  • The team mates who believe in the mission, and work tirelessly to try to bring it into reality despite seeing the size of the hill you have to climb and your deficiencies as a leader daily.
  • The friends who like, tweet, congratulate you on, and promote your product knowing firsthand it’s quite not ready yet.
  • The powerful but fleeting bits of positive feedback you get from the universe when souls you don’t know on the other side of the globe validate what you’ve built.
  • The countless hours of grinding when metrics go down and stay down, but you still believe in the mission.
  • The early customers who pay you, despite the product’s shortcomings.
  • The team mates that accept layoffs with grace, and in their pain, support the go-forward crew when it becomes clear there is more to do than runway to do it.
  • The team that stays, passing on outside opportunities, to fight despite grim prospects and uncertainty until the bitter end.
  • The wife who cares for you during the shame when it’s time to give up fighting, despite the brunt she bore.
  • The kids who talk to you, play with you, and listen to you as if you were never gone, just happy to have their Dad back in body and, most importantly, mind.
  • The investors, who through each 1:1 delivering the bad news, openly express understanding, appreciation for your honesty, and even willingness to invest again.
  • The friends, who take you out for a beer and get your mind off it.
  • The parents and siblings, who could care less what happened at work and just want to be with you because you are family.
  • The authors like Brene Brown and Cal Newport who have taken the time to write down the advice you needed.
  • The profound gratitude you feel when you realize others draw closer when you share your shortcomings and weaknesses, not pull away.
  • The acceptance of self, the way you are, deficiencies, faults and all.
  • The 10k+ customers who keep using the product with no updates for months.
  • The incredibly talented torch bearer, Kris Gellci, who quits his job to keep the dream alive, moving with the speed of a two-pizza team all by himself.
  • The colleagues who welcome you back, despite your attempt not having succeeded.
  • The best friend, who could have (and maybe should have) abandoned you long ago, yet continues to spend countless hours investing in your relationship to help you sort through it all, learn more about yourself, and progress on your journey to become a more whole person.
  • Learning, having encountered the nearly worst-case scenario, that the pain was well worth the realization that joy in life derives from relationships, and that just my engaged presence is enough.
  • God, who offers a new opportunity, each morning, to start fresh and do better. <sobbing ends>

Thank you friends, the experience has meant the world to me.


thought pieces at the intersection of consumer tech investing and entrepreneurship.

Shawn Carolan

Written by

VC, founder & believer that consumer tech can improve everyday lives. Investor in Chime, Roku, Uber, IMVU, Siri, JUMP Bikes + +.


thought pieces at the intersection of consumer tech investing and entrepreneurship.

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