Drew Chapin: Young Tech CEO From Peak to Valley
“Suffering ceases to be suffering when it finds a purpose.”
What kid doesn’t want to grow up and be a tech entrepreneur CEO in San Francisco? That’s exactly what Drew Chapin did. He built an innovative ad platform at Binga Network that let users buy products directly from digital ads, no redirect required. The idea was solid. The execution was promising.
Then he started lying to investors.
One lie became five. Five became hundreds. By the time the FBI knocked on his door at 6 AM on Thanksgiving week 2020, Drew had committed securities, bank, and wire fraud trying to keep his dream alive.
The Kid Who Was Always Building Something
Drew grew up in New England with entrepreneurship in his blood. His dad ran a small business. His mom was an artist who ran galleries. He was reading PC World magazine at 10 years old, watching Bill Gates and Steve Jobs change the world.
He went to college in Vermont, became president of the student body, earned a business degree, and started working at Microsoft before graduation. But the big tech corporate life felt too slow. He was a tiny cog in a massive machine.
“My biggest issue working for a big tech company,” Drew told me, “was not knowing if you made any kind of impact. I was really seeking the opportunity to have a bigger impact.”
So he jumped to startups. Progressively smaller and smaller companies. Some wins, some colossal failures. He loved every minute.
The Cash Incinerator
In his late twenties, Drew and a talented developer struck out on their own. They built an ad platform that could replicate a mobile shopping experience inside any display ad on any website. Click, swipe, buy. No redirects.
The unit economics were clean. Money in, money out. One problem: they paid for ad placements upfront but didn’t get paid by advertisers for 90 to 150 days. During growth, every dollar went out the door and didn’t come back for months.
An investor called it a “cash incinerator.”
Drew needed to fundraise. But the ad business isn’t sexy. It doesn’t attract the big investment rounds that AI or crypto gets. So he’d go out, pitch, and hear the same thing over and over: “We like the business, but we want to see you get to this number first.”
When One Lie Became a Thousand
Burnt out from running the company 60 hours a week plus a full-time fundraise, Drew started showing investors what they wanted to see. One small fib. One exaggeration. Keeping a partner’s name on the deck even though they’d canceled last month.
“One lie leads to five lies leads to dozens of lies leads to hundreds and thousands of lies,” Drew said. “I was just being reactive. But when I read the discovery after the FBI woke me up, I looked at the totality of what I did and went, wow.”
He knew the books were sideways. He was working on fixing it. His logic was that everyone, investors, banks, everyone, had an interest in seeing the company through. Why would anyone flip the table?
But someone did.
6 AM on Thanksgiving Week
Monday morning, 6 AM. Dead asleep. A knock at the door. A dozen FBI agents with assault rifles. They’d scaled the back of his house to block his escape. They put him and his fiancée in handcuffs.
Drew was thrown in county jail with no idea what would happen next. Would he be there for months? Years? He had no clue how any of this worked.
“Very fortunately, I had a lawyer to call,” he said. His dad was incredibly supportive, immediately action-oriented. “That’s for another day. Let’s focus on getting you out of county.”
Drew spent a night, got in front of a judge, and was released. Then came 13 months of limbo between arrest and sentencing. A lost year. Floating. Waiting for the next call from the lawyer.
”You Just Didn’t Know How to Fail”
Drew knew from day one he wouldn’t go to trial. He’d done wrong. No point in wasting everyone’s time.
His lawyer was brutally direct: wire fraud means prison time. It’s about minimizing damage and moving through quickly.
The judge at sentencing said something that stuck: “It appears you just didn’t know how to fail.”
Drew got three years. He served 14 months at FCI Lewisburg in Pennsylvania.
21 Days in the Hole
Drew reported in February 2021, during COVID protocols. Even though he tested negative and had his vaccination card, Lewisburg put him in quarantine behind the wall of the medium security facility.
A 5x7 cell. 24-hour lockdown. No clock. A tiny window where you couldn’t tell if it was light or dark outside.
He thought it would be three days. Then five. Then seven. Ten. Two weeks.
On day 22, they opened the door. His whole body was shaking. Total nervous system reaction. Then they walked him down to the camp.
“That was my nice little COVID introduction to my BOP experience,” Drew said.
Finding Meditation Behind the Wall
Drew wasn’t particularly religious when he went in. But Jeff Grant from the White Collar Support Group had told him before he reported: “Well, you might want to think about it.”
So Drew started exploring. He got into meditation. It became core to his daily life. By the time he left, he was running the Buddhist meditation group on Sundays in the chapel.
His mantra: radical acceptance. When crazy things happened, fights, program shutdowns, everyone’s release date getting pushed back 30 days because of one person’s misbehavior, Drew accepted it.
“These are the facts. Accept it. Be a little more patient with the things you have control over and the things you don’t.”
Making Good Use of Time
Halfway through his bid, Drew was walking the track with two guys who were leaving the next day and the next week. He was trailing behind, listening.
One asked the other: “Do you think you made good use of your time?”
That simple question stopped Drew cold. He had goals, sure. He was working out, reading. But was he really being tenacious? Checking every box?
He finished his sentence with 100 books read. He left knowing he hadn’t wasted the 14 months.
Back in Startups
Drew left Lewisburg in April 2023. After a month in the halfway house and three months on home confinement, he spent the summer getting his feet under him. A lot had changed, OpenAI, Elon buying Twitter, the whole tech landscape shifting.
Then he turned up the job hunt. He wanted back into early-stage startups. It’s exciting. It’s what he does.
He found founders willing to give him a shot. Open-minded people who understood that his crimes were a series of mistakes he’d learned from. He’s back in business development, building again.
Now he wants to work with young entrepreneurs, especially in tech, to share what he learned. He thinks about all those founders at incubator demo days putting slides on screen, not knowing they’re committing securities fraud with exaggerations and embellishments.
The Takeaway
Drew’s biggest lesson is about intention.
“When I was committing securities, bank, and wire fraud, I just wasn’t being very thoughtful. I was being careless, not just with my own life but with all these people around me.”
Now he wakes up and makes sure everything serves a purpose. He thinks through how it will impact others.
“I would have said a couple years ago that if this blows up, it’s just for me to deal with. Not that simple. We’re all interconnected, the people close to you and all the ripple effects outside of that.”
He’s 35 now. He’s got his brain. He’s got his experience. And he’s got a story that might keep some young founder from making the same mistakes.
Drew can be reached at drewchapin.com.