I Once Told An Investor They Shouldn't Give Me Money
Believing in yourself is freaking hard
2015 was a crazy year in many ways for us.
(From left to right: Jeff our developer & employee #1, Vinnie, me and Meghan the co-founders)
We launched our product (Followesports.com, the TV Guide for esports)
Won $25,000 in a local business plan competition
I quit my job, with the blessing of my wife (also a co-founder), to chase this startup thing full on with her and Vinnie
People were actually using our product
Investors were asking us when we were going to raise money
Sounds like an aligning of the stars, by most metrics. We had it made. All we had to do now was keep following the path and we’d be successful beyond our wildest dreams in no time, right?
Wrapping my mind around this idea of investment was incredibly hard for me. People could have enough money that they would happily give some of it to another person who they barely knew based on some Powerpoint slides? This just seemed absurd to me, a kid who grew up in a small town where you feel upper class if you can afford to buy a new car instead of a used one.
How could people be so reckless with their money?
This conflict between the Marty who started working at age 9 and the 35 year old Marty who was going to ask people to trust him with a sizable amount of their money became a bigger and bigger anxiety inside of me. Who were we (and really I was saying “who am I?”) to be trusted to take hundreds of thousands of dollars that someone else earned and turn it into something of value?
Don’t get me wrong, I come from a long line of hard working people. That’s always been our edge. A resolve, a grittiness. All kinds of shit happens in life, and my family has always been good with taking a hit, getting back up off the mat and keeping at the grind. My grandfather, my father, my uncles, me - we all learned to build things with our own hands. For as long as I can remember I was learning how to do it myself. You could rely on yourself to do it right and inexpensively. That wasn’t something you could look to other people to do.
So it made me suspicious throughout the process of learning to fundraise. Suspicious of what I could expect from myself and what other people could expect of me. This grew to be pure terror, as I could only picture things going wrong. Eventually it all came to a head when the pitching process started.
I had this really great mentor from our local incubator Venture Creations. Bill Jones had been working with companies for a lot of years. He was the reason I even began to take the business seriously in the first place. When at first we were just thinking of this as a side project for fun, he convinced us that we should join the business plan competition and see where it took us. So he’d been right before, which gives him the benefit of the doubt.
We spent a few months crafting our deck and our pitch, with Bill as our guide. He’d get other folks to come listen to our pitch so we could see how it would land on new ears. Every draft of the deck I drew up he’d sit down and work through with me slide by slide to get it just right. I needed introductions to VC’s and angel groups? Bill was on it. Without that guidance I’m sure I wouldn’t have even been able to start down a fundraising path at all. After all the prep, I finally knew what I was doing as I began to fundraise.
Until I didn’t.
Our very first VC meeting was with a friendly fund, who Bill knew very well. It was setup by Rich, one of the head guys at the incubator, so it was a very warm intro. I was well prepared for who I’d be meeting with, how I could best present my case and had a leg up because of the relationship with the incubator. This was going to be the freebie in a long line of what was likely to be difficult pitches. I walked into the meeting with confidence, gave what I felt was a really solid pitch and left feeling ok. I did what I set out to do, and now it was out of my hands.
After Rich and I touched base on how it went, I headed home for the night. This is where the self doubt set in. I was completely overwhelmed. These guys might give me a million dollars? Why the hell would they do that? All we did was write some code for a website that made no money and had a small user base. They must be crazy. Or wait, maybe it’s me who is crazy? Have I tricked them somehow? That must be it, because no rational person would be considering handing over a million dollars to us based on the slide show I created. I was just some kid who grew up next to a cornfield.
The really insane part of all of this is it was just a pitch. Just a regular, ordinary normal pitch in which the guys heard me out, asked some questions, we parted ways and they probably hadn’t spent much time thinking about for the rest of the day. But in my mind this thing was massive and catastrophic. This was the end all be all.
The first thing I did the next day was call Rich and tell him to let the VC guys know that I was pulling my pitch. I could tell that Rich hadn’t ever had a call like this before. Was I sure I wanted to do this? (I was) Did I understand what this would mean? (I did) After our conversation, Rich called them presumably and that was the deflated balloon of an ending for my first VC pitch. In a span of 24 hours I went from excited to tackle the day and push this startup into the future to terrified little boy who was overwhelmed by imposter syndrome.
Bill wisely gave me a couple of days before he asked me to come into his office to meet. I remember this overwhelming feeling of embarrassment that I had, and how it disappeared almost immediately upon sitting across from Bill. If there’s one thing I always recommend to new founders it’s to find someone you can turn to in moments like this that gets it - really gets it. They don’t have to be tech royalty who can phone their huge network of Silicon Valley CEO’s or some coding genius who can help solve your most difficult product problems. Bill and I often laughed about how little he understood what our company was building at the time because it didn’t really matter if he knew esports. What Bill brought to the table was empathy and guidance. I sat down across from him, held it all together for about thirty seconds before I burst into tears. I told him how insane it seemed to me that someone would willingly give me their money and how I would surely waste it.
Throughout the next hour he brought me out of the deep end and back to a level understanding of realty. Investors understood the risk they were taking (far better than founders do, in all reality). They wanted to find founders like us, who cared that much about how we treated their money. We were a good choice for them to invest in.
Needless to say, I didn’t get a chance to pitch that first VC again and get them to go all in on us. However I did walk away that week with a much needed change in perspective about what it was that we were doing. We were building a company. It was going to be hard and it probably wasn’t going to work and people were likely to lose money by betting on us. All of that said, people were still going to bet on us and come along for the ride because they did believe in us.
There’s one final lunch I wanted to recall to bring this all home. Josh, one of our early angel investors took me out to lunch to kickoff our relationship. We sat and talked for awhile about lots of things unrelated to the investment itself while we ate. We finally came to a point where he was giving me the check and he said something that has been a powerful force for me over all of these years: “Truth be told, I don’t really understand what you guys do, nor do I think that I will learn to understand. I’m doing this because I believe in you. I have a feeling that betting on you is the right move.”
In that one moment, those words changed my trajectory forever. I finally understood what I was doing when I was raising money. I was meeting people who could believe in my co-founders and I as people. They were investing in us.
YOU ARE A HUGE SUCCESS! I'M PROUD OF YOU! BTW, WE LIVED NEXT TO AN APPLE ORCHARD NOT A CORNFIELD. LOL!