Why I Left my Startup

A 100-days later, from the other side

Update Nov ‘13 — Happy ending to this story. Tunezy ended up getting acquired by SFX Entertainment not long after I wrote this post. A great outcome for the entire team!

In a world of never-give-up, persist through the trough of sorrow start-up cliches, I quit mine 100 days ago. It was a very painful and personal experience — I left the company I co-founded, said goodbye to the team I had been in the trenches with for two years, and simply moved on.

Despite a new job and reinvigorated social life, in the time since, there hasn’t been a day I haven’t thought about it. Feelings of remorse, betrayal, and cowardice are mixed with those of reason, courage, and optimism. It has been a roller coaster of emotion; but in a hundred days, I have finally built some perspective on why I quit.

I chose life over glory, and I admitted to myself that I was losing passion for my startup.

Passion

“One of the huge mistakes people make is that they try to force an interest on themselves. You don’t choose your passions; your passions choose you.”
- Jeff Bezos

Having passion for what you’re doing is probably the biggest entrepreneurial cliche of them all, but I’ll go on the record saying that it’s 100% true.

I know this because at the beginning, I did have passion. What I eventually realized, however, was that I confused my passion for building a business with that of solving a problem.

2 years ago, I was comfortably climbing the corporate ladder at a Fortune 500 company. Having just been promoted to the amorphous ‘Associate Finance Manager’, I was by many measures doing well. I was happy there — the work, the company, and the opportunities were great.

The problem then? I wasn’t being challenged.

You know that voice in your head… the one that imagines you’re a hero in an epic movie, and have enourmous potential to fulfil? The one that says “you were meant for bigger things”?

Yup, that voice was screaming inside of me.

Like a naive child, I was ready to latch onto anything epic, and when my eventual co-founder — an even more ambitious individual in a similar situation — ended up living in the same building as me, it didn’t take long for us to whip up ideas together on evenings after work.

It was literally a napkin idea at first, something about a music social network, where users earned points and would democratize the industry. We built out a model, a deck, and even got some contractors to start building a prototype for us (we were both non-technical).

Things got crazy when we pitched at a local start-up competition and won, banking $5k and some credibility. I quit my job the next day, we raised some angel funds, and I began the greatest learning experience of my life.

False Positives

In all worldly things that a man pursues with the greatest eagerness he finds not half the pleasure in the possession that he proposed to himself in the expectation. — Robert South

Throughout the next year, we hit a lot of milestones:

• Growing the team from two to nine
• Moving from a living room to an office
• Launching the product
• Hiring interns
• Raising more money
• Hosting launch parties and mixers
• Getting written about in the media

These were all the things that I dreamed about when I first took the plunge, and the fact they were all happening was really gratifying.

But those feelings came and went.

The work was not easy. We were building a new market, catering to a fickle customer, and generally struggling to achieve product/market fit. We pivoted the business three times, had multiple redesigns, and had to restart work quite often.

Eventually, we developed a clear direction (“fan experiences”), built some traction, and even generated revenue. We were finally adding features rather than throwing out whole concepts and starting from scratch. It was an important step for a startup, but I was curious to find that it wasn’t bringing me as much joy as moving into an office did a year earlier.

Over the 6 months leading up to my departure, I hid my feelings from the team, and fought off the negative ones as hard as I could. I felt, and was, responsible for keeping us focused and building the right things. I constantly reminded myself,

“It’s just a rough patch…startups are hard, you knew this already…keep going.”

So I did. I worked even harder, and longer. I pushed myself to learn programming so I could help more, and was eventually pushing code to production. The team pushed harder still, and our development cadence was faster than ever. We built our first external API, added new features, and quickly iterated on feedback. We built more in the last three months than we did in the previous year.

I didn’t burn out from the hours (the work was challenging), but after a while I knew my soul was no longer in it. I didn’t spring out of bed or have the same energy in the office, and I started walking to work instead of biking because I wanted more time alone. My resolve to go the extra mile for the customer was diminishing, and so was my zeal for the music industry in general.

After the novelty of entrepreneurial ‘firsts’ wore off, all I had left was that eroding resolve to fight.

But that was not enough to make me give up.

Life over Glory

“Success is not the key to happiness. Happiness is the key to success. If you love what you are doing, you will be successful.”
- Albert Schweitzer

Some people can persevere the hardships of entrepreneurship despite a lack of passion for the problem they’re solving. Their sheer will to win, and want of glory, is enough to keep them going.

It turns out, I’m not one of those people. At least not for this problem.

You have to give up a lot to be an entrepreneur, most importantly time from your relationships. More than just less time together, the cognitive saturation from running your own company means that you’re often distracted, even when you’re with people. Either out of curiousity or support, your friends and family will always ask, “how’s the business is going?”, so even the most self-disciplined can’t avoid the subject.

Your business is the first thing you think about in the morning, it’s the last at night, and it creeps into your dreams, to boot.

Life was also not slowing down for the sake of the company — It was my first year as a married man, I had a nephew on the way, a loving family, and friends who were all entering exciting stages of their lives. But over the course of building the company, I felt myself losing them.

On the financial front, it was very difficult for myself and the rest of the team. Some of us had gone a year without any income. We had originally planned to take salary by then, but hey, shit happened. I thought about my wife, how I told her I would quit my job only months before we got married (she was still supportive), and I felt an immense sense of guilt that I was denying her some stability.

My health was degrading. I ate horribly, dropped out of the sports I was in, and simply didn’t have the drive to hit the gym outside of work. You can blame it on lack of will power, but I’d argue willpower is, in the short term, a finite resource.

All this considered, I started asking myself what I really valued in life.

Was the chance for glory, and my loyalty to the team worth losing a lifetime of cherished relationships and further loss of health? Was the hardship of startup life worth a business I had lost passion for?

Given the cost, was success even going to make me happy?

It took some time, but I realized it wouldn’t. I had the difficult conversations with my co-founder, and told him I was leaving.

No Regrets

“A man has cause for regret only when he sows and no one reaps.”
—Charles Goodyear

100 days ago I quit my startup.

I’m still a shareholder and believer in the business, and I admire the team that chose to stay. They will succeed and do great things.

Thinking back now, I see how far I stretched myself. With the experiences I accumulated and the gains I made in character, I have no regrets.

Looking forward, I’m not done with startups. I’m not done growing, and I’m not done learning —in fact, I’m just getting started.

The last two years exposed me to things I never would have otherwise seen. Witnessing first hand the way technology and design is changing the world has forever inspired me.

It bridged me into a product management career, and renewed my passion for learning.

It showed me what I was capable of, and exposed how I could be better.

Onwards.