Setting The Stage

Graduating with a 1.92 GPA from high school in 2001, my mother encouraged me to apply to as many colleges as I could, with the hopes that at least one would allow me to show up in Fall. I applied to 10 state universities in Ohio (…known as the “spray and pray” technique). Through my Mom’s diligence my application arrived via UPS 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. OSU chose to accept me via their Early Acceptance Program which was designed to “look past” things like low GPA’s.

For some reason I assumed my lack of interest in formal education would fade and I would make all those around me proud in college. Higher education turned out to be the same process of “sit in this chair, face forward, memorize this info, and regurgitate it onto an exam”. High school all over again.

At 20, I entered my third and final year at “THE” Ohio State University. It was obvious that I wasn’t college material. In my first two years my largest college related accomplishments were joining a fraternity, Alpha Epsilon Pi, and the fact that OSU accepted me in the first place, considering my academic record. 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 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, in my room alone, only to emerge, binge drink, and 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 awful electronic music, and eating endless amounts of Hot Pockets. Upside: Learning how to build websites shaped so much of my life and success. Downside: I was intensely lonely and riddled with guilt over once again failing academically.

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, except for 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 is better than fiction. We met through private messages, then through a quite random mutual sorority connection we had, and then finally in-person over take-and-bake pizza. 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. Even though I had built up a pool of a dozen clients (most of them auto repair shops) I could tell early on that the web design business was a miserable way to make money.

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 (this was 2003). When that fell through, I tried to sell pet urns online. Just like dogs & cats it served, that business met its demise. It’s quite hard to launch a startup alone. So, I vowed to find a cofounder to build something with and then luckily stumbled upon a young Russian immigrant dude that changed my life forever.

Lev and I met for the first time at a rush event at my fraternity. I thought he was an asshole and was glad when he didn’t return again. Fast forward several months and via serendipity we met again through a mutual friend. Lev was told that I was a “computer guy” and he wanted to run some “insurance marketing” (lead generation) idea past me. Yay………. (There aren’t enough dots I can put here to explain how boring I thought this idea sounded.)

However, upon meeting again I realized that I had gotten Lev all-wrong. This guy had a fire inside of him like no other. He was the same age as me, but had already built a $200,000/yr revenue insurance agency in less than 18 months. Pure hustle is the only way to describe him. Lev can sell anything to anyone, any time. I had found my business partner.

In 2004, InsuranceAgents.com was born. **Although it wouldn’t be officially called that until late 2009, back then it was a collection of ugly websites designed for one purpose only: traffic generation. Lev had figured out ways to game Google, Yahoo, and MSN for tons of cheap 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, and the industry was boring. Somehow, I was the happiest I’d ever been.

We moved into a windowless hovel of an office in downtown Columbus in 2005 (The most exciting part of the day was when the our office neighbor did nude photo-shoots on the empty floor above us). Then we moved into hovel with windows (sans nudity) 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 so my ex could enroll into a PhD program here.

Two Roller Coaster Years That Would Change Me Forever

Entering 2008, life was at a peak in so many ways. The company was now named 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 almost $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. On the home front, I was enjoying the married life in Chicago and finally feeling that I had arrived.

This was the moment you spend all those 16-hour days hoping for and why you tell yourself those little white lies every miserable morning about how “one day we will make it big and this will all have been worth it!” My ego was growing by the day. We were making more and more aggressive decisions for faster revenue growth. We would Google things like “process for filing IPO”. At home my ex and I were thinking about buying a huge condo downtown! Yea!!! I AM THE MASTER OF MY FATE, I AM THE CAPTAIN OF MY SOUL!!!

(….imagine an impending sense of doom style soundtrack playing in the background as you read on….)

At the beginning of 2009, we set our yearly revenue goal at $20MM. Lev and I both felt that there was nothing in our way from getting there other than that “pesky technology platform” we ran the company off of. We decided to rebuild our entire IT infrastructure from scratch. Even though we both suspected that the development of the platform was rushed and wasn’t ready to go live, we decided, “Fuck it. We’ll do it live!!(NOTE: Audio includes swearing.)

On July 1st, 2009 we told the dev team to push the various, different new systems into production. It’s so easy to look back and say, “wow, that was stupid…“, but our heads were buried in the roll-out process with tunnel vision engaged. We wanted growth at all costs, so it was simple to ignore the warning signs. We were confusing brash carelessness with decisiveness; oblivious to our own ignorance as how to handle a company at this scale and revenue growth.

On my end of things, I had personal issues fueling the need to relaunch quickly. I had consumed myself into the business and was desperate for good news because my marriage had fallen apart in the months leading up to February 2009. 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 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 “functional” with a ton of errors. Our original six person web dev team, except one developer, had abandoned ship. Lev and I burned through over $1M in 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 October, we had lost quite a few employees, burned millions of the company’s and our own personal funds, lost hundreds of 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 (I’d show up at 8am one day, 2pm the next, sometimes not for days at all) and verifiably insane at worst (randomly starting bar fights or making some dangerous decisions few know about). 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. This is one of the best decisions I have ever made and I strongly encourage anyone suffering to consider to it. 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…) All that was designed to break me out of my introverted shell and learn how to interact with other humans. Step three was I wanted to feel healthy and proceeded to drop 20lbs.

With the company in stable, but guarded condition, there was small window for me to come up for air. 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 slightly 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.

Closing Out The Decade

From the first moment Lev and I met to talk about insurance, the boredom set in. I loved the idea of building a company and watching it grow, but the world of insurance was not for me. 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 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 were small pockets of entrepreneurship going on around the city, but no sense of community (“A rising tide raises all boats.”). 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. We only filed the LLC paperwork because we wanted liability protection for holding events. 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. Luckily early 2012 would see the sale of InsuranceAgents.com to Bankrate (NYSE:RATE), and the emergence of Technori as an actual startup.

The exit was a positive end to the experience, but still bittersweet since the seven years our insurance startup took to scale, shaved 20 years off my life via stress and heartache. This period of time encompasses some of the best and worst moments of my life. I know I’m supposed to say, “It was all worth it and I would do it again in a heartbeat!” #learningexperience #thickskin…. That’s not respectful of the way I feel though. It was a mixed bag, that I think the meaningful results of it will only come if I understand what I learned and put it in practice. It’s entertaining to see how my twenties seemed to line up with me entering entrepreneurship and exiting, with a strong dose of love and heartbreak interjected.

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.

(**Originally posted 01/15/2013. Edited and updated 01/06/2015.)