Why I Joined Fundfly

April 8, 2021

"I have this idea for an app."

I glanced to my left, to see if there was a clear path to the bathroom. Perhaps I could fake food poisoning and make a run for it.

Standing in the middle of my step-brother's 40th birthday party, I knew I'd simply have to endure another "pitch." Ugh. OK, let's see what this one is.

You might be thinking I'm a Venture Capitalist, with millions of dollars in a bank account just to drop fat checks on the next would-be Uber or Spotify. In fact, I'm just a guy who grew up on a farm, who curiously found himself in the middle of the tech world.

Anyway, back to the pitch.

"I want to make an app that calculates overtime."

"Well, couple of things. The first is that the app market is now so crowded that it takes a tremendous effort to get noticed. You either get REALLY lucky and catch lightning in a bottle, or you spend a LOT of money on advertising an PR."

"But what if it's something a lot of people could use."

"I'm game. What's your idea."

"An app that calculates overtime."

"That's already on your phone. Take your hourly wage, multiplied by 1.5, multiplied by the overtime hours you worked. If you want, there are more complex calculators online that will even deduct the taxes and show you your take home check for that pay period."

The would-be tech entrepreneur walked away deflated, which wasn't my intent.

I probably could have broken the news that his...ummm...invention? was already a basic feature on every phone in the world. But at that point, I'd hit total burnout from hearing ideas.

Twenty years ago, every 19 year old in the world wanted to be a pro athlete or movie star. Today, everyone dreams of being the next Zuckerberg or big thing on TikTok.

And there's nothing wrong with that!

However, my early days in Chicago radio and network TV taught me that I couldn't keep up with reviewing aspiring musicians demo tapes that were pitched to me (due to literally thousands of requests)

After a decade in tech related jobs in the corporate, nonprofit and venture backed spaces, I hit the same place where I just couldn't fit in the Starbucks meetings or phone call requests for "tech pitches" from well meaning individuals who genuinely wanted critique or perhaps a word of encouragement.

The "Offer I Couldn't Refuse."

When Drew called me for (what would eventually become) Fundfly, I took the idea a little more seriously, because I knew my old friend did not approach ideas lightly. When Drew and I first met, he considered buying a business before deciding it wasn't for him.

Mentally, that was the first hurdle cleared, as the vast majority of "pitches" from friends and acquaintances assume a tech startup "can't be that hard." That attitude is a sure fire way to A). hate it or B). fail spectacularly from throwing in the towel at the wrong moment.

"Well, let's test out the idea" I replied, after hearing his concept to disrupt the crushing student loan debt market.

At the time, I assumed that's as far as it would go.

We set up some initial meetings with top minds in business, legal and finance. The whole point was just to find people to tell us this wouldn't work. (I've got a pretty full plate by day and a two year old daughter, so I wasn't exactly looking for "one more thing" to occupy my time and pull me away from Netflix).

Then the funniest thing happened. We couldn't find anyone to give us a reason why crowdsourcing student loan debt wouldn't work. The biggest pushback we got was "I paid off my loans, why should someone else have help?" (Response: you don't have to participate).

I believe the reason no one has tried to build a startup around one of the biggest (or, the very biggest) financial crisis facing Americans today is because...it just seems impossible.

But that's only if you look at the staggering amount of debt.

If you zoom in to individuals, families, friend groups, local communities, a solution to the student loan crisis seems much more possible.

After 500 pitches, I finally heard a startup idea that A). could change the fabric of the nation and B). presented a workable solution to a problem everyone else was too intimidated to take on, making a complex issue simple and solvable.

Which is the one pitch I just couldn't refuse.


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