Writing this Article Cost Me a Million Dollars

Dan Bender / October 25, 2017

18 months ago, I was living the life that was the envy of all my friends. I was working for a retired billionaire, getting paid in the high six figures, and was living with my beautiful family in a gorgeous home on a golf course just outside of Aspen, CO. My daily commute topped out at about 15 minutes, I spent nearly every winter weekend running laps on some of the best ski slopes in the world, and I even bought my own barrel of whisky at the local distillery that was kind enough to serve me a pour every time I stepped foot in their tasting room. I was weeks away from my 40th birthday and, although everyone I knew would make comments like “sounds like a rough life” or “I’d kill to switch with you for a day,” neither them nor I had any idea that my life was about to make a seismic shift.

There was no tragic event that forced the shake-up. No one got cancer and/or was in a sudden car accident that made me think about mortality. I didn’t have some epiphany where I talked to God at the top of a mountain and I didn’t see my future laid out before me in a dream. I’m also 99.9% sure that my decision to disrupt everything wasn’t the result of a mid-life crisis. It was actually quite the opposite. My perception of someone who has a mid-life crisis is some guy who feels stuck in a life he doesn’t like, a job he hates, a family he’s annoyed with, etc., and wants to drastically shake things up by doing something nutty that everyone knows will lead to dangerous results. I experienced none of that. I enjoyed the work I did, although not the feeling of being held captive to the whims of another human. I did then, and I continue now, to adore my amazing family. I had a decent amount of money in the bank and had traveled enough in my youth to have scratched that itch.

For me, it was a strange sensation of wanting more and wanting less at the same time. Wanting to be challenged and to relax, wanting to experience discomfort and, well, comfort at the same time. I kept catching myself deep in thought about weird circular logic that didn’t make sense to me. It took a while to process, but I eventually figured out what it all meant.

My mind was clearly telling me that I needed to take control of my life. I wanted to put my knowledge and experience to work by building something meaningful for me and less of doing that for someone else. I wanted the ability to work really hard and pull all-nighters when I needed to, but also to take 3- week vacations and coach my kid’s soccer team when I wanted to. I wanted to remember what it was like to feel the burn of earning peanuts while I worked my way up the ladder, but knowing that I could tap into my savings account if I needed to and not feel guilty about it.

So, I did what any sane person would do. I asked my wife to kiss her dream house and 5-star vacations goodbye so that I could rip off the band-aid and start over at 40, because it just felt right.

After a couple of months of working through various opportunities in various places, I decided to head back to the Washington, DC area where I spent the most of my career. I was fortunate enough to have been introduced to Abtin Buergari and Ashtan Moore, through a mutual acquaintance, CJ Jensen. The other three guys had been working on some business plans for a few months, and it just so happened that they needed someone with my skill set. After spending a total of 4–5 hours on the phone and a having a couple of in-person meetings, I convinced them to carve up the cap table 4 ways and let me join in on the fun.

We thought about the early successes of the great industrialists like the Wright Brothers, Henry Ford, Andrew Carnegie, etc., and the various iterations of the things they built. There was usually a prototype, followed by a Model A that was produced for sale. But the real money maker would be the Model B, which was often mass produced after the kinks had been worked out with the Model A. Our mission was to take something other people were already doing, but refine it and do it better. So, in that same vein, our company, Model B, was born.

It all seemed so easy when we were finalizing the business plans. Step 1, come up with a name. Step 2, tell everyone you started a business. Step 3, make a billion dollars. Easy peasy, right? Actually, we’re a fairly seasoned executive team, so we weren’t really that naïve. However, we did build out a financial model that was supposed to be our downside case, but would have proven to look like a home run when stacked up next to our actual year 1 financials. The challenges of going into business with people you don’t really know all that well eventually come to light. It’s kind of like getting married after you’ve been on one or two dates. You might be really attracted to the other person and have a hell of a good time on those excursions, but living with that person in sickness and in health is a whole other side of that coin.

Our original business concept was to build out a suite of professional services that we could offer to startups that would help them accelerate their growth. A few of us had made some angel investments in a number of startups to limited success and, in each case, the investments were passive — meaning that we couldn’t exactly call up the executive team and tell him or her that they were doing it wrong, and that we were the saviors if only they’d let us jump in and fix everything. We thought that if we could get startups to pay us as consultants for the things that we were really good at (digital marketing, financial management, data analysis), we’d have the inside track to see how effective the management teams were and ultimately have better insight as to what the growth potential looked like. From there it would have been as simple as investing in the next round or converting our fees to equity instead of cash.

However, we all know that Murphy’s Law is a scientific fact, and easy-peasy makes lemon squeezy, which in case you’re wondering, tastes awfully sour.

About three months into our venture, we came to the stark realization that startups don’t have any money, virtually all of them think that they are the next Uber, and most would rather drink a gallon of Hulk Hogan’s sweat than to give us a meaningful share of their equity. Sales were slower than anticipated, which meant that we’d be experiencing some financial discomfort. You remember when I said above that I wanted that? Yeah, I found out I didn’t really want that. Anyhoo, about three months later, my long-time friend that brought me into this thing, CJ, got some really exciting news that he was being awarded a business license that effectively gave him a monopoly in a very hot industry. It was bittersweet, but we all knew what was coming next. He quickly rounded up a killer management team and some core investors and moved onto his next venture. The rest of us were able to slow the cash burn, and the Fab Four became the Thrifty Three.

Along the way, we managed to find a couple of brave souls who believed in us and our ability to muscle through the difficult times. Our first employees, Ben Huizinga and Tony Kurilla, slowly worked their way into the boardroom where they found the courage to make their voices heard. The feedback was well received, and they’ve never been shy about sharing the hard truth with us when we need a reality check. They helped us reshape our service offering and dial into what we were exceptional at. Our earliest customers who took a chance on us when no one else would will always hold a special place in our hearts. A few of them naturally bowed out, but those who stuck around have seen a massive uptick in the quality of our work, have now become our biggest evangelists, and continue to graciously refer us more business. Our internal processes became tighter by the day and we now have a development team in place that is making great strides in automating our work.

As things improved, we added a couple of more hires. Hibby Zubairi came on about 6 months ago to lead our sales team, and most recently, Ryan Peper joined us as our Operations Manager to ensure high quality work goes out the door on budget and on top. In a little over a year we went from being a day 1 startup to having real revenues from high quality clients, a solid team, tight operations, and a really nice service offering. I am incredibly proud of what this group of humans has accomplished, and although things are definitely trending in the right direction, we’ve still got much to do.

When I made the decision to leave Aspen, I wanted more, and I certainly got it. I’ve gained a sense of comradery in my team that I’ve never experienced in my professional life before. Those guys are like brothers to me, and I love that we’re in the trenches together day in and day out, building something that is personally meaningful. I wanted less, and I certainly got that as well. By my estimate I will have given up more than a million dollars in wages from the time I made the decision to leave Aspen to where I can begin to pay myself something approaching market rate. I wanted to be challenged, and anyone who’s ever been a founder can certainly attest to how hard all of this is. I’ve lost countless nights worth of sleep worrying about how I was going to pay the bills. I wanted to relax and was able to do so when I spent a month with the family in California this past summer. I still worked from the road, but I could have never gotten away with being gone for a month while working for someone else. I wanted to experience discomfort, which for the reasons noted above, I obviously experienced. And I still wanted the comforts in life.

Now let’s be honest. None of the things I’ve talked about are real problems. I’m not going to pretend that my life has been exceptionally hard or I’ve faced real world struggles like other folks have, and I’m thankful for that. From a young age, I worked my ass off for other people so that they would reward me with dollars. I made smart investment decisions and lived within my means. I planned for my future, and as a result of that, was fortunate enough to get to the point where I was able to parlay my experience and money into this entrepreneurial pursuit and still have a safety net.

So while the journey I have been on and the words I write sharing that story have cost me a million dollars, I have no doubt that I will eventually be writing an article that I hope to call “Writing this Article Made Me a Million Dollars.”

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