"seo doesn't work"
In 2019 HeyTutor was growing fast, and I reached out to over 100 investors. Most of it went nowhere. Analyst meetings, polite passes, wasted time. Then I found a small fund called O'Connor Ventures, which was Kevin O'Connor's personal investment vehicle. I sent our pitch, and Kevin himself replied. One or two sentences, all lowercase, the way he always writes when he doesn't feel like trying. It basically said: seo doesn't work.
SEO was one of the biggest drivers of our business at the time. So I wrote back a long email explaining why he was wrong, along with everything we were doing right. What I didn't know was that I was arguing about internet advertising with the founder of DoubleClick, the company Google bought for $3.1 billion to run its ads.
To my surprise, he sent his son, Cormac O'Connor, to come see us. Our office was an apartment with about 30 sales and operations reps packed inside. Cormac walked into that and probably wondered what he had gotten himself into. To his credit, he was respectful from the first minute, and I've liked him ever since. I showed him everything, and he said he'd have to run it by Kevin. I was raising $1M.
"you need to become a better negotiator"
Months of back and forth later, Kevin wanted to meet. I call him "Mogul," by the way. Not "a mogul" or "the mogul." Just Mogul. He pulled up to our apartment in a Ford Focus, which is hilarious when you consider his net worth, and I pitched him HeyTutor. It was a much tougher meeting. Kevin is very hard to read. He doesn't say many words, and the few he says carry a lot of meaning. And when he's thinking hard, his eye twitches, which honestly scared me.
They decided to go into diligence. We didn't have enough money for a lawyer, so I brought in a friend I did MMA with, Dylan Lojac, who was still in law school at the time. He worked for next to nothing and got us to the finish line. Fun fact: Dylan is at Latham & Watkins today.
The deal closed in my bedroom. Literally. Me, my cofounder Ryan Neman, Kevin, and Cormac, negotiating a valuation. We shook hands at $8M. Then Kevin looked at me and said, "you need to become a better negotiator."
The worst pitch of my life
Fast forward four years. HeyTutor had transitioned into high dosage tutoring for school districts. Long, sticky government contracts. But growth had slowed, we were burning money, and the new model had a brutal cash problem. Winning a district contract meant paying to train tutors, deploy them, and pay them every two weeks, while the district took 90 days to pay us. We were winning contracts we didn't have the money to service.
There was one option: go back to Mogul. This time it was different. He wasn't confident more money was a good idea, and he told me plainly that if I wanted it, I would have to convince the partners at ScOp Venture Capital, the fund his personal investing had grown into. That's how I met Ivan Bercovich.
I pitched ScOp the next day, and it was the most embarrassing pitch of my life. I was unprepared, and they questioned everything. Ivan led the room, asked the hardest questions, and left the second the meeting ended because he had somewhere to be. Afterward Kevin called me and said, "wtf was that."
The next morning I got an email from Ivan. They wanted to invest another $1.5M. I accepted in a heartbeat. From there HeyTutor thrived, all the way to the acquisition by ESS in 2026, an above market return for the firm.
Last updated September 1, 2026