“I made a decision last {year} that I would die for it” -Drake

So, the actual lyric by Drake on his song entitled “9” is this: “I made a decision last NIGHT that I would die for it”. What Drake is referring to, at least my interpretation of it, is his commitment to his craft and doing what he has to do to become, and remain, the best. Additionally, he’s willing to go through the inevitable pains that come with this journey, “just to show the city what it takes to be alive for it”. Although Drake is talking about his music career, his feelings are parallel to mine as a first-time tech startup founder! I made the same decision in 2015.

Last year, November, I was at a very critical cross road in my life. A couple months prior, I had begun messing around with an idea that quickly created a fire in my belly. Things were getting serious and I knew I needed to leave my current job if I was gonna make this start up thing really happen; this was my only purpose for moving to the Bay Area in 2014!

My Instagram post the exact night I came up with the concept for Win-Win

With 2 beautiful, growing kids and an amazing wife working within the education system (CSUEB), I was fully aware of how my current income enabled us to live quite comfortably. Without it, we’d barely be getting by — remember, this is the Bay Area! Anyway, my plan was to stay at work a few more months, save a little more money, and then I’d leave in late January to start my own company! As life would have it, things didn’t play out exactly how I imagined. In November 2015, things were rough. My wife’s father suddenly passed away (the day before my 29th birthday) and I was trying my best to comfort her and the grieving family. After spending a few weeks in my wife’s hometown of Detroit, MI trying to be a source of support, I returned to work only to be shown the door — “Mike we’re going through a company restructure and we’re gonna have to let you go”. WTF!?

As they say, when it rains it pours! Remember those beautiful kids I mentioned earlier? Well their little tummies didn’t care if daddy was laid off; neither did their expensive pre-school. I needed to make something happen, and very quickly. So, here I am at this cross road… Do I go out and hunt for another job so I can ensure the comfortable lifestyle my young family had just begun to really enjoy? Or, do I use this opportunity to focus on my own idea and try to make something happen? The latter was extremely risky — and the risk I’m referring to had nothing to do with the idea or viability of the business, but only the fact that I had a family where I was the primary bread winner. When you start a company from scratch, ain’t no salary bihh!

My goal when we moved here was one thing and one thing only, build my own startup. 18 months later, here was an opportunity to do so. Usually an entrepreneur will have some money saved up (or borrow from friends/family) to cover their living needs and initial startup costs until they get far enough along to attract investors… or paying customers. My wife and I were just starting to rebuild a steady savings since the mayhem of relocating and having back to back newborns. However, we didn’t have enough money saved to sustain our family of 4 at our current expenses — especially since we had just moved into a new house. We wouldn’t have lasted longer than a few months.

Michael Jr & Leila

Decision time.

Imagine jumping from the roof of a skyscraper with the goal to land on the roof of the next building, but you can’t even see the other building, at all. You’ve heard it was there and you can only hope that you jump far enough to reach the next building. Additionally, you know there’s a real chance that you could totally miss and fall to your demise — and you’ve heard about the many others who have already (9 out of 10 startups fail). So, with the decision to jump to entrepreneurial glory knowing that I’ll potentially miss, “I made a decision last night that I would die for it, just to show the city what it takes to be alive for it”.

9 by Drake — “Views”

Yes, I took the leap but only after closely assessing the feedback I was getting from potential users and fostering strategic relations that could help me on this journey. One of the primary reasons I was able to “go for it” was because my wife supported my decision to jump. She adamantly believed that, if I put my mind to it, I could jump to the moon and back, let alone this unseen “rooftop”,

Since “jumping” in December 2015, I’ve made good distance but I’m still in the air right now and from this angle it’s hard to tell if I’ll land on that “rooftop”, or go tumbling down to startup death. Either way, my decision was made.

Since making the decision:

  • Named “Most Innovative Fantasy Sports Business” by the Fantasy Sports Trade Association (FSTA)
  • Awarded $150K in dev resources after beating 15 Silicon Valley startups in the STRV pitch competition
  • Featured in Forbes
  • Successfully raised $1M in funding in ~120 days
  • Launched on 9/1/2016

Be sure to check out Win-Win — your support will be the wind beneath my wings that will carry me to the other side :)

-MTB