Give Me 30 Minutes, and I Will Kill Your Entrepreneurial Dream

“I had a boyfriend who told me I’d never succeed, never be nominated for a grammy, never have a hit & hoped I’d fail. I said to him someday, when we’re not together, you won’t be able to order a cup of coffee at the fucking deli without hearing or seeing me.” — Lady Gaga

What makes an entrepreneur? Nature? Nurture?

80% of what it takes to win the entrepreneurial lottery is engrained deep inside ones mind and cannot be taught or learned. The remaining 20% comes from starting, trying, failing and getting your junk kicked in until you have a chance to do better the next go around. And even then it requires powering through hundreds of ‘I lost’ moments before you’ll see real success.

This isn’t just my crazy theory. Smart people like Harvard Business School Professor Shikhar Ghosh have done studies to identify the exact reasons that more than 96% of businesses fail within 10 years. Many of the core reasons are simply non-entrepreneurs trying to be entrepreneurs. The remaining are a lack of experience.

Throughout my 20+ year entrepreneurial career, I’ve met a lot of entrepreneurs, and “entrepreneurs”. Many have asked to meet me and talk about an idea, pitch me for funding, get advice, etc.

I finally discovered the greatest service I can do for anyone over a 30 minute meeting.

Give them sound advice from a guy who has been through it all? No.

Make some connections that could help them succeed? No.

I spend all of my available time trying to kill their dream.


Entrepreneurship, especially in tech, is one of the most toxic environments that exists today. There is no industry producing more billionaires and billion-dollar returns. It’s the only place that some kid with a good idea can go on to change the fabric of the connected world in a matter of years and become incomprehensibly wealthy. What no one wants to talk about is the price us entrepreneurs pay in the pursuit.

It isn’t for lack of trying. There have been a lot of great exposés in to the dark side of entrepreneurship. Tragic articles hit the wire seemingly weekly of the meltdown or demise of yet another bright star. The suicide rate in Silicon Valley is 4x the national average. Mental illness rates are off the charts.

The reason these tragic realities aren’t discussed more openly is because entrepreneurial leaders are held to insane standards of invincibility and perfection. Showing vulnerability, admitting fear, seeking help—all of these could make investors, employees or partners lose faith in our ability to lead, so we are inherently encouraged to suppress everything and fight our demons behind closed doors; maintaining and perpetuating the image of perfection in entrepreneurship.

This bliss becomes a draw for non-entrepreneurs to try their hand at this crazy world. “Why would I be an accountant when I could just start an app and be a billionaire?”

The prevalence of this is alarming and insane. The pursuit of riches, freedom and fame completely obfuscates the realities of what is really means to start and run a business. This naiveté puts people in positions they never intended to get in to, sometimes putting their wellness, finances or lives at stake.

Dream Killer

So what do I do when I meet a young entrepreneur? I exhaust all of my available energy dishing out the real facts on just how brutal and taxing the journey can be. The pitfalls. The pain. The realities that the media doesn’t talk about. The crazy game of poker, with the highest odds, that is entrepreneurship.

I tell them they will very likely fail.

I tell them they will have to take personal risk after personal risk, that could have debilitating effects long after the company is gone.

I tell them that even if they do find success, life can actually get a lot harder. Success is not easy to deal with.

I tell them the startup graveyard is littered with ideas just like theirs.

I’ve killed the “dreams” of many entrepreneurs in such sessions.

Why do I do such a thing, especially as an entrepreneur myself?

Because if a stranger can kill someone’s dream in 30 minutes, it’s not a real dream. And I probably just saved them an incredible amount of heartache.

Real entrepreneurs can’t be swayed, especially by a stranger over a coffee. My words of warning will be adrenaline to their heart. My facts about failure will be a dare for them to prove me wrong. My dosage of truth about their idea probably not being as good as they think will be motivation to improve it.

Real entrepreneurs (in the same way I used to react to all of the people telling me I can’t do it) want to prove the world wrong. All I am doing is validating that urge, and giving them some helpful insight that I wish someone had told me at that age.


I’ve recently finished a book about my entrepreneurial journey (publishing this year, click here if you want an early copy). Unlike other business memoirs, this one is raw, dark, hyper-honest and pulls the blindfold off of a number of topics that we aren’t really supposed to address.

One colleague read an early draft of the book and gave me very unexpected feedback: he loved the story, and it made him not only reconsider his new business idea, but ultimately not pursue it. “I’m just not up for all of the bullshit,” he said to me.

I felt bad at first. Did my story just change someone else’s?

But I then realized, the book served the same purpose as my coffee meetings with young entrepreneurs. While my story reads like A Wolf of Wall Street meets the Social Network, it is oddly representative of millions of other entrepreneurs stories. If other startup mavens were allowed to be honest about what really happens in positions of young leadership, power and success, many stories would probably make mine sound like amateur hour. It is an insane journey at the best of times.

I realized that for an honest dose of reality to have the effect on someone for them to say “you know what, this isn’t for me”, is actually the greatest endorsement I could receive. Non-entrepreneurs will get to the end and say “good lord. I am glad my life is more normal.” Real entrepreneurs will have that familiar fluttering in their heart, and despite the downfalls, warnings and tragedy, will be even more motivated to dive in to the black hole and make their dreams a reality.

Catch me on Twitter and Instagram.


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