A few days after graduating high school in Florida I moved into a "coliving space" called Founder House in downtown Brooklyn. It's no longer around, but it was a 4-story townhouse where ~20 tech people lived: software engineers, product managers, designers, etc. (There were also some aspiring filmmakers and doctors.)
My roommate Ben and I started a tech startup called salesperch (intentionally lowercase), which was something like a plug & play multi-level marketing pyramid scheme for major brands like Coca-Cola (people get paid commissions to recommend products to their friends).
We were going to change the world, but we needed money. A few hundred thousand dollars at least, to start––enough for a few years runway and a small team.
One day we found out about an event at the Princeton Club of New York in midtown. It was about networking with Ivy League startup people and learning about fundraising. We thought "yeah we want to raise some money let's go tell them our idea man."
The only problem was neither of us went to Princeton––or any Ivy League school for that matter; and that was the only way you could get in.
While Ben had graduated from college a few years prior, I was only a month out of high school, and was fresh to say the least.
Despite this glaring issue, we went to the event anyway. We had a pretty solid plan. I was going to puff out my chest and flash my expensive watch I stole from my mom's ex-boyfriend. Ben was going to pretend to be in a very serious conversation with me.
We went in, nodded at the guards, and walked right by.
"What the fuck that was easy."
For someone who grew up in a small town in Montana, this place was nuts. You know how fancy churches have those really nice, dark, shiny wood pews that look kind of like caramel apples? This place had that everywhere: the floors, the walls, the ceiling, you name it. Shit was nice. They even had oil portraits of dead people on the walls.
Anyway, we made it up to the room where the event was happening. There was maybe 10-15 people there.
"Alright guys let's get in a circle and introduce ourselves."
"Fuck, shit, okay, yeah let's do it." Ben and I went to the far end of the circle.
"We're um working on this startup called salesperch and uh, yeah we're going to help brands spend less on advertising by leveraging consumers to market products for them."
The room didn't care and we moved on. After an hour or two full of unmemorable talks the event ended, and everyone stayed to gossip with each other. We used the opportunity to tell people about our startup, hoping to get connected with an investor.
We went up to the fanciest guy there. He was in his 50's or 60's with a full head of white hair. He looked like Mr. Burns from the Simpson's, but in an endearing way.
He said his name was "blah blah [very famous last name you would definitely know]." Ben asked more questions, and it turned out this guy was an heir (?) to one of the most famous American business families of all time.
I won't say which family he came from, but they're up there with the Rockefellers, Vanderbilts, and Carnegies. Movies had been made about his family and at their height they were worth billions.
Ben's eyes widened and he whispered to me "My mom literally works for his company, and his dad was our governor."
He was very polite and respectful, and he treated us like we weren't some stupid kids that snuck into the club from off the street. He invited us to his office for a private meeting the following week.
Ben and I were pumped. We left the club and got back on the subway to Brooklyn. We started scrolling through Wikipedia, and found out about how [famous Hollywood actor] was nominated for an Academy Award for playing his brother in a huge movie a few years back.
We also found out that his name wasn't just [first name] [last name], it was "[first name] [last name] the fifth."
As far as we could tell, this was big time and we knew we had a real shot of saving salesperch from imminent death.
We got researching, coding, building, planning, writing. "How much money can we make?" "How do you make a pitch deck?" "Why would he invest?"
We perfected our deck and made a demo of the product. The next week we showed up to our meeting early, right on the corner of his dystopian concrete office building in midtown Manhattan.
We waddled in––a couple of schmucks in dress shirts––and were immediately stopped by the doorman.
"What are you doing here?"
"We have a meeting with [Mr. Burns]."
"Are you sure?"
"Yes I'm Matt Henderson and this is Ben Wang and our meeting is in 15 minutes."
"Do you know where you're going?"
"Have you been here before?"
The doorman, confused how these assholes got a meeting with Mr. Burns, escorted us to his conference room and closed the door.
This room was the size of a small bedroom. It was fancy in a Connecticut country club kind of way, and the walls were covered in green felt like a pool table. There was a boujee coffee set and intricate carvings on the ceiling.
There were no windows, and we were getting nervous. "We prepared for this!"
Suddenly the door opens and a maid walks in, fills the coffee pot with coffee, then leaves.
We twiddled our thumbs in silence expecting him to show up any second, and we didn't want him to walk in on us midway through an existential crisis.
Minutes passed until the door finally opened. He walked in, quietly. He said hi, went straight to the coffee pot, poured us each a cup, then poured himself one.
He asked us if we wanted cream. "No thanks."
We looked at him with cheeky grins, "So, we've been working really hard on this and we're excited to share it with you."
He sat down slowly, paused for what felt like a minute and said:
"Listen, I'm not going to give you any money."