I routinely run into folks working in finance romanticizing the virtues of startup culture. It’s easy to romanticize when you constantly are fed stories of a group of founders working out of a garage going on to sell their businesses for millions, if not billions. It’s the modern-day retelling of the tale of Don Quixote.
How exciting it must be to go boldly into the arena to pursue your dreams and come out the victor. The grass is always greener on the other side I suppose. When I look at the career path of those in finance, I routinely think ‘that would be nice.’ It would be nice to choose a career where you didn’t have to run the risk of burning through all your savings to launch your idea. That’s what jumping in the arena often entails.
This has been the trajectory of many of my friends who have started their own companies. It is a reality of startups. Ramping up a startup can be...

I understand how the trappings of tech culture seem alluring. Perhaps it’s the open office spaces, the ping pong tables, or the ubiquitous bring-your-dog-to-work policy.

Maybe it’s the idea of meetings with venture capitalist who are always eager to jump on a call to discuss your ‘exciting project.’ I get it. It can all seem like a high stakes role playing game that revolves around you, the ‘tech visionary.’

I am often amazed how the perception of startup culture and the actual operation of a startup are so disconnected. Creating a sustainable business, in fact, has very little to do with these trappings. It’s not VC meetings, ping pong tables, or how many buzz words you can fit into your pitch.

It has more to do with extreme discipline to keep your burn rate low and methodical attention to product development, operations, and aggressive user acquisition. It’s about getting through...

Startup growth can be painfully slow. So slow that many entrepreneurs just give up and quit when their launch doesn’t go as expected. When you think about it, who can blame them for quitting. Yes, it is really hard. So hard that you may end up in a nut house if you think about it too hard. However, that’s not why I expect that most founders opt out.

They fail because they never had a chance, not when every incentive leads them in the wrong direction. The top thought leaders and business experts deceive us with shortcuts and tricks that optimize for short term success. There are no silver bullets; there are no shortcuts.

We’re dazzled with the idea of hockey stick growth — the idea that there is an inflection point in a startup’s growth that moves the rate of expansion from linear to exponential. One day you’re working in your garage on an idea; the next day you’re Facebook, Uber, or...

Suriname is a small Caribbean nation on the Atlantic coast of South America. It has a population of a little over half a million people. If you’re like me, you had probably never heard of it. And you’ve certainly never heard of Edward Gessel.

Edward Gessel serves as the Chairmen of Suriname’s Special Olympics delegation. Suriname’s participation in the Special Olympics was nothing less than improbable. In the months leading up to the Games, Gessel had a problem. There were no funds to pay for the travel expenses for his delegation. Gessel had to stare down an ominous ledger every day, and the math was not in his favor. The $3000 plane ticket to the Games is more than the average Surinamese household income. Getting the funds to send the delegation to Los Angeles seemed impossible.

Left with no other recourse, Edward Gessel mortgaged his home. With the funds from this selfless act...

This is the age of the selfie-stick. We lionize those that clamor for our attention and impulsively beat our own chests because of an unflinching belief that we are special.

One only needs a pulse to understand the importance we place on the self. These are the fruits of narcissism. It’s easy to lament its corrosive effects on our culture; it’s much harder, however, to look inward and see how we as individuals foster and let narcissism corrode our own lives.

I think about this particularly when it comes to individuals we consider “driven”.

When we send young people out to the arena we arm them with a myth. It’s the myth of tunnel vision, of singular focus: if you sacrifice and dedicate yourself completely to an end you will emerge on the other side the victor.

Pick the arena: athletics, business, politics– within each field there exists a hero that tackles an obstacle through a...

“No man’s good by accident. Virtue has to be learnt.” —Seneca

Some of us dream of Elyssium. We point to the moon and see it in arm’s reach. We quit our comfortable jobs to embark on a new venture, or catch a Greyhound bus to Hollywood from somewhere in the obscurity of the Midwest to pursue our dreams of appearing on the silver screen, or wake up at dawn to train to compete at the highest levels. That’s the life we choose. We visualize, have purpose and execute.

These dreamers are the modern day Don Quixotes; jumping into the arena, scoffing at conventional wisdom, and taking the proverbial road less traveled. In every industry we find them and glorify their success, often times ad nauseam, but this of course is not the purpose of the blog. This is a blog about doing hard things.

When I started my company I had the fortune of befriending my own band of Don Quixotes. We were...