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Resignation of a Startup CEO

Resignation of a Startup CEO

Brand Building

Life is hard. Starting a business is hard. Raising money is hard. Operating a business is hard. Being CEO is hard.

But resigning from the startup company I co-founded was one of the hardest decisions I’ve ever had to make.

Some entrepreneurs hate the idea of going back to the corporate world, the 9-5 “rat race”. Some cringe when thinking about having a boss and losing their autonomy. And others only want to be known as “bootstrapping bandits”. There’s nothing wrong with self-identifying as an entrepreneur.  But none of these reasons are why I anguished over my impending tough decision.  Heck, I’ve gone back and forth between corporate America and entrepreneurship a few times.  No big deal.

What’s the big deal?

You see, when starting a business, you go from an idea in your head that solves a problem to putting it on paper, from talking about it to dreaming about it, then obsessing about it.  You start making plans and executing and pitching and revising and pitching again. You lose sleep because you’re so focused, and you find out that you focused on the wrong things, so you lose more sleep and you don’t care because you can see the future.  You work for shit pay (or no pay) because you have a solid plan that you will execute flawlessly (or fail often) until the big payoff (the exit).

You spend less time with your wife and family because you’re dedicated.  “They’ll be glad you did one day.” That’s what you sell them on.  You’re the leader so you’re “setting the example.” You recruit smart people to work with you and get them to believe in your vision. You convince them to work for less pay because they’re getting options! You recruit more smart people to advise you. You sell the future. You make commitments. You pitch. You get punched in the face. You revise. You execute. You pitch again.

You convince suppliers to let you pilot your product. You overcome objections and sell the future. You pitch and revise and pitch again. You do whatever it takes.

You hustle and pitch the media and network and talk to hundreds thousands of people and lose sleep because you’re focused. And your number one supplier pulls out right before your beta, so you spill your guts and pitch and sell the future and spill your guts some more and they agree not to pull out.

You talk to customers and potential customers and take notes and make changes and you thank people because you owe them.

You travel thousands of miles to speak and build a brand in your industry and you listen to people and discuss and take notes.  You talk to your team, you talk to your advisors, you re-read your notes, you sleep on it…then you pivot!

You re-focus to solve a bigger problem and lose sleep and see a better future, and you make better plans and you execute and create budgets and you pitch. You tell a story, the problem, the solution, the market. You’re changing an entire industry! You sell your product, your brand…but you’re really selling yourself.

The hardest part

You’re the brand. People believe in you because they like you. They see your vision. They want to support you. You commit to them, they commit to you.

Your vision, your company, your solution, your future, your commitments, your passion, your baby.

And you walk away like it never happened.

The right decision

On August 2, 2013 I resigned from the startup company I co-founded like all of it never happened.

But it was one of the hardest decisions I’ve ever had to make.

For professional reasons, I cannot go into the reasons for my resignation, but it was the right decision.

For now, I’m taking some time off to decompress, reflect and consider what’s next.

This blog

Through my own wins and losses, advice from mentors, and discussions with other founders I’ve learned some valuable lessons.  I plan to use this blog as an outlet to share my experiences and encourage discussion on the topics I write about  so others can learn as well.  Please join in on the discussion by reading and commenting on my posts, and if you feel the content provides value to you, please share with your networks.

If you want to connect with me online or in-person, here are some quick links to do so:

12 thoughts on “Resignation of a Startup CEO

  • >> I resigned from the company I co-founded like all of it never happened.

    I’d have to disagree with this statement. You now have years of new lessons learned and hundreds of new connections–including Glen and myself! Your next venture as well as everything else you do will have the added advantage of the experience and wisdom you’ve gained from this one!

    • You are absolutely correct Aaron, and thank you for this comment. The statement was meant to infer that while the lead up to the decision was tough, the decision in itself was swift.

  • “You travel thousands of miles to speak and build a brand in your industry and you listen to people and discuss and take notes. You talk to your team, you talk to your advisors, you re-read your notes, you sleep on it…then you pivot!….You’re the brand. People believe in you because they like you. They see your vision. They want to support you.”

    Caleb, I hope you look at this excerpt I took from your post, and look at it often. You left a lot of sweat and blood on the field, and no one can fault you for the final outcome. You’ve turned a lot of heads along the way, and left a positive mark out there for your brand. This is just the next pivot in a long career. Looking forward to seeing where it takes you buddy.

  • Great read and thanks for sharing. I can only imagine what it would be like to make that decision, but as long as you know you made the right decision then in the end you did what was best. Best of luck in your next venture and looking forward to seeing what comes next.

  • “What lies behind us, and what lies ahead…..are tiny matters as compared to what lies within us”. One of my favorite quotes. It takes courage to do what you did. Just remember, the journey is a big part of the reward.

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