Well, that was interesting… (A look back at my twenties…)
Setting The Stage
Graduating with a 1.92 GPA from high school, my mother encouraged me to apply to as many colleges as I possibly could, with the hopes that at least one would allow me to show up in Fall. With the exception of my hometown Youngstown State Univ, I applied to nearly every state university in Ohio. Through my Mom’s diligence my application arrived the morning of the first day Ohio State University admissions opened. Her persistence, plus the four times I retook the ACT to better my score paid off, when OSU chose to accept me via their “Early Acceptance Program”.
For some reason I assumed my lack of interest in formal education would fade and finally I would make all of those around me proud. At 20, I entered my third and final year at “THE” Ohio State University and it had become obvious that I wasn’t college material. In my previous two years my largest college related accomplishments were joining a fraternity, Alpha Epsilon Pi, and quite honestly the fact that I was accepted in the first place to OSU. I was drinking two 24-packs of Natural Light a week and no longer showing up for class. No beer gut though, I looked like a human lollipop at 6 feet tall and 140lbs, with my giant balloon head floating above.
When you only appear at the exciting moments in the people’s lives around you, it’s fascinating how you can develop a reputation for being outgoing, while also being widely made fun of as a shut-in. Many who know me now would not have recognized me then. No, not because I’ve gained 80lbs, but rather that I was fiercely introverted with occasional explosions of a personality. Many times I would spend three to four days indoors, mostly in my room alone, only to emerge and binge & party for two days. Then back to my room (…or “the cave”, as everyone called it) and rinse and repeat for week after week. I’d pass the time building websites, creating really awful electronic music, and eating endless amounts of Hot Pockets. Upside: I learned the skill that has shaped so much of my life. Downside: I was intensely lonely.
Spending a majority of my time online forced me to create a social life there as well. Your options back then were extremely limited, so I spent most of my time in internet forums and IRC, with the exception of one website, HotorNot.com. Not sure if anyone remembers, but HotorNot used to have a dating function that allowed people to not only rank “Hot” people, but also connect with them. This is where I would meet my future ex-wife. Truth tends to be so much better than fiction.
We met through private messages, then through a quite random sorority connection we had, and then finally in-person. Your classic Junior hits on Freshman type of relationship, just minus the sleaziness. At the same time, I decided that if I was going to be a hermit and build sites all day alone, I at least should build something that I own. Something that could have a life of its own and much bigger than just one website for some local business.
With some inspiration and swift kick in the butt from a friend, I launched a flash memory store online. It failed after six months, so I tried to launch a 3D modeling company. When that fell through, I tried to sell pet urns online. Just like dogs & cats it served, that business met its demise after a few months. I realized that it’s quite hard to launch a startup alone, vowed to find a cofounder to build something with, and then stumbled into a connection that changed my life forever.
Lev and I met for the first time at a rush event for my fraternity. I thought he was an asshole and was glad when he didn’t return again. Fast forward several months and we met again in a meeting setup by a mutual friend, this time to chat about something he wanted to build. Lev had been told that I was a “website dude” and he wanted to run some insurance marketing (lead generation) idea past me. Yay… Upon meeting I realized that I had gotten him all wrong and this dude had a fire inside of him like no other I had met. Lev is the kind of person you immediately recognize: this guy can sell anything to anyone, any time. I had found my business partner.
In 2004, InsuranceAgents.com was born. Although it wouldn’t be called that until 2008, back then it was simply a collection of brutally ugly websites designed for one purpose only: traffic generation. Lev had figured out ways to game Google, Yahoo, and MSN for tons of traffic via PPC, while I was busy building dozens of sites. We were ramen-profitable by our second month, operated out of Lev’s parent’s basement, the sites were hideous, the industry was boring, and I was the happiest I’d ever been. We moved into a windowless hovel of an office in downtown Columbus in 2005, then into hovel with windows, and finally there were five us at the beginning of 2007 on the brink of building something big. On the home front, 2005, 2006, and 2007 would bring engagement, marriage, and a move to Chicago.
Two Roller Coaster Years That Would Change Me Forever
Entering 2008, life was at a peak in so many ways. The company was now called InsuranceLeadz (yes, I hated the “z” as well) and we were growing fast. Really fast. Really, really fast. In 2007 we had done $750,000 in revenue and at the beginning of 2008 we were projecting to do $3MM in revenue for the year. We did nearly $12MM instead, at awesome profit margins. Keep in mind, we were bootstrapped, having not taken a penny in funding. When something works out dramatically different than you expected, but in a good way, it’s a feeling unlike any I can describe. I was enjoying the married life in Chicago and finally feeling that I had arrived. This was the moment you spend all of those 18 hour days hoping for and why you tell yourself those little white lies every morning about how “one day we will make it big!” My ego was growing by the day. At home we were thinking about buying a big condo downtown!! Yea!!
At the beginning of 2009, we set our sights on $20MM. Lev and I both felt that there was nothing in our way from getting there other than our pesky technology platform we ran the company off of. It was time for a major technology overhaul it took until July for our web dev team to prepare the new platform. Even though we both sensed that the platform had been rushed and probably wasn’t truly ready to go live, on July 1st, 2009 we told the dev team to push it out anyway. It’s so easy now to look back and say, “wow, that was fucking stupid…”, but when your head is buried in the process, it’s all too simple to ignore the warning signs.
Feeding the need to relaunch quickly, was that at this point in the year, I was really desperate for good news. My marriage had fallen apart in the months leading up to February 2009 and by July I was divorced and alone in a city where I had relied on my wife’s friends to be the only people I knew. There was no way I was going to delay a relaunch of the site, which was the last thing I had left in my daily life keeping from the very edge. Again, quite easy to look back now and recognize irrational behavior.
In the 45 days following the relaunch of the site, every single system the company depended on to operate had failed, was currently still failing, or was just barely working. Our original six person web dev team, except one developer, had abandoned ship. Lev and I burned through over $1MM cash trying to keep the company on life support and pay salaries. Through the incredible kindness of a close friend, we secured a huge temporary loan to float us until we could repair our leaking ship. By the end of the year, we had lost quite a few people, burned millions of the company’s and our own personal funds, lost hundreds off customers, damaged our reputation in the industry, and morale was that of a funeral home.
Sept and Oct 2009 I hit bottom. I’ve heard from those around me then that my behavior was erratic at best, certifiably insane at worst. To start the year married, full of hope, financially awesome, and then end the year divorced, angry, and bankrupt was a bit too much to handle.
Things had to change and they needed to change now.
Step one was beginning to see a psychologist to get an objective third party view of my past and present. Step two was joining a bunch of Meetup groups, taking speech & singing lessons, and I started going to events with the intention of forcing myself to walk up to people and say “Hi”. (terrifying… every moment…) Third was I wanted to feel healthy and proceeded to drop 20lbs.
With the company in stable, but guarded condition, there was enough of a window for me to come up for air. In November I decided it was time to at least go on a date and started the search. Where else, but the internet of course. This time on a somewhat more respectable site, OkCupid, I met my love, Taryn :) We dated for a while, moved in together, and have been at each other’s side every moment since. She is the reason I’ve been able to recover, rebuild, and keep my life together.
From the first moment Lev and I met to talk about insurance, I was bored. I loved the idea of building a company, watching it grow, and potentially exiting it at some point, but I never was interested in the world of insurance for a second. It was approaching six years since we started and 2009 showed me how messed up my life priorities were. I needed something that I could sink my teeth into and it needed to be in an industry I actually enjoyed. On top of that, it needed to be something community related, because I refused to ever be in a situation again where I was alone and without any local friends.
In 2010 it was becoming obvious that something amazing was happening in the Chicago startup world. There was a ton of action happening, but very little sense of community. Out of that opportunity, Technori was born. Five of us started it as a passion project, with no intent to turn it into a business. It was something we could all throw ourselves into and each of us found our own purpose in it. Through 2011 Technori would grow to the point where as a passion project, it was taking up more and more of my attention and cutting into my InsuranceAgents.com time. Additionally, I was tired of digital startups in general and I needed something tangible. I would step down from my role at the company in Oct 2011 and focus all of my effort on a new startup, Bow Truss Coffee Roasters.
“Why Coffee?” is a question I get frequently. For the same reason as “Why Insurance?” An opportunity presented itself at the right moment in time and I pounced. I could care less about ideas or industries; I only care about the founding team. With that mentality this is not the first or last time I will fundamentally switch industries or mediums.
2012 would see the launch of our roasting house, the sale of InsuranceAgents.com to Bankrate (NYSE:RATE), and the emergence of Technori as an actual startup. Having my birthday be at the beginning of the year allows me to associate a specific age with its corresponding year. Coming back from the edge to stability in my life and business in 2012 is the biggest accomplishment of my twenties and a wonderful way to close out 29.
In a separate post I’ll detail out the next decade and my thoughts on how it may play out.
