1) Quitting my last job was one of the hardest things I ever did.
Before founding Pristine, I worked for my father. The longer I worked for my father, the more I realized how much I couldn't stand working for him. For months, I grew increasingly depressed. I wasn't able to focus at work for more than 20 consecutive minutes. I would constantly come back to TechCrunch and refresh the page looking for a startup that would inspire an idea for me to pursue in health IT. I had a few ideas, but I knew they were all crap.
In February of 2013, Google announced Glass. Fireworks began erupting in my brain. It was just too good to be a true: a new platform that presented a new blue ocean of opportunities backed by one of the world's most reputable companies that had an obvious place in healthcare. It was a match made in heaven.
By May of 2013, literally I could do was think about Glass. I had hyped it up so much in my mind that I couldn't even think straight. Then I played with Glass for the first time. I was let down. The screen was abysmally small. And the battery life sucked. The trackpad was terrible. And there were no built-in voice APIs. What the fuck was I supposed to do with that in healthcare? That's useless (later we realized we didn't need any of those things to build a compelling business around Glass).
Meanwhile, things got worse at work. I literally couldn't think about my salaried job at all. My roomate was in the process of launching his own startup. The only thing I could think of was freedom. My dad knew that I wanted to do something around Glass in healthcare, and he berated my constantly. Why leave something proven for something mythical? And why Glass? What a silly, useless piece of shit.
On June 7th, he forced the issue and asked me to quit or drop all of the Glass stuff. My last day at work was June 14th, 2013.
Out of dumb luck, Patrick and I got offered $100,000 a couple of weeks later by an anesthesiologist in Phoenix that we connected with through my blogging (blogging was a new years resolution for 2013 that accomplished exactly what I intended it to: it created luck). 24 hours after being offered our first $100,000, I went out in New York City to celebrate my funds raised with my friends and lost my only Google Glass device. I woke up the next morning with the worst hangover in my life, and without the single most important thing I needed for my business. I don't know what caused more vomit: lack of Glass or the hangover.
A few months later, after increasing our burn to $75,000 monthly, we were about to run out of money. Being the naive entrepreneur that I am, I didn't realize when we only had 3 months of cash remaining. For the 3 weeks leading up to that payroll, I could barely sleep. I threw up at least twice thinking about what I would tell my investors. I let 2 empoyees go. And I couldn't raise enough money. We missed payroll. Well, kind of. Miraculously, Bank of America let us dip into our credit card to cover payroll.
Since then, we've signed half a dozen clients, and raised boatloads of money. The future looks remarkably bright.
My only advice to (prospective) entrepreneurs is to persevere like a mother fucker. The world will fuck you unless you fuck it back.