At 22 years old Enrico Palmerino had sold his first company ThinkLite, bought himself a Maserati, and had already met the love of his life (now wife) Carlie Palmerino.
Accomplishments most of us won’t achieve in a lifetime.
Yet he wasn’t completely happy.
“After I sold ThinkLite I went through a bit of depression,” Palmerino told me as we sat at WeWork where he is currently building his new business, BotKeeper (more on that later).
“Enrico and ThinkLite were synonymous,” he said. “I identified myself as my business and I didn’t know what to talk about anymore or how to hold conversations with people.”
These feelings of depression are not unusual for entrepreneurs. Watch CNN’s Silicon Valley’s Secret and you’ll see a much darker side to a lifestyle that from the outside often seems glamorous and exciting.
“After the sale I bought some toys. But the Maserati wasn’t about possessions, it was about idolizing that car as a kid, and working hard enough to be able to get myself one,” said Enrico. “But after about 6 months it’s just a car. I mean I bought some really nice things but I had to find my purpose again.”
Palmerino’s feelings post-sale are sadly not uncommon for startup founders, but bouncing back from that to build not one, but two more businesses by age 28 is. To get answers as to how he pulled this off I asked to meet with his wife and partner of 7 years, Carlie. Upon meeting her I immediately understood.
Carlie is energetic and warm. She’s the kind of person you feel like you’ve know forever. She’s also incredibly hard working. The two met when Enrico was a junior at Babson College. Having just started traveling around to meet with potential investors for ThinkLite, Enrico found himself in need of a car. Carlie was paying her way through school by working at the dealership that Enrico would purchase his “Mini-Cooper S, stick, sunroof,” said Carlie.
“We love cars,” she added.
Carlie has found success in pharmaceutical sales and though the travel sometimes gets to her she loves her career seemingly just as much as Enrico. I wanted to dig in a bit more to find out what it’s like to live with a serial entrepreneur/boy wonder.
“That man would work 24 hours a day if he could,” Carlie told me. Enrico described a typical work day as up around 5 a.m. working by 6 a.m. and not home again until 7 or 8 at night often staying up until the wee hours of the morning (I’ve personally received multiple 3:00 a.m. emails from him) and starting it all over again.
“We live in downtown Boston because we tried living outside of the city and we literally never saw each other," said Carlie. "Now, some days we can at least have a cup of coffee together in the morning but for the most part I don’t expect to see him during the workweek.”
Carlie has set up days that are specifically for the two of them to spend time together. For the Palmerino’s, Saturdays are for each other. “We really don’t see our friends because that day is really the only day we spend together,” Carlie adds.
This is just one of the sacrifices the two make for each other and for the business.
Through my conversation with Carlie, it became very clear to me that this unwavering support and dedication must have contributed to Enrico’s ability to successfully move on from ThinkLite and start all over again. She has zero resentment towards his work schedule and talks about his work with pride.
“I’m Enrico’s biggest fan,” Carlie stated with a smile. “I’m in awe of everything he’s built and accomplished.”
Today, Enrico runs Botkeeper, which automates bookkeeping for startups and small businesses. Botkeeper uses combination of skilled accountants and automated data entry through the use of machine learning to keep the books for its clients. He started the business because frankly he hates accounting and struggled with it at ThinkLite. In the last year alone, botkeeper has grown to provide bookkeeping to over 160 companies in 4 countries making it the fastest growing accounting firm in the Northeast. Inc., Forbes, and Entrepreneur have recognized botkeeper as a disruptive force and leader in automated accounting.
“He’s made bookkeeping sexy and I’m so impressed by it,” said Carlie.
I asked Carlie if she ever wishes Enrico had a regular job and she replied “yes” but only on vacation. “I just feel so badly that he doesn’t get to enjoy every second of our trips the way that I do,” she said. “On our honeymoon he would wake up four hours before me to work.”
“My wife puts up with a lot,” said Enrico. “She worries about my health and she reminds me that there’s more to life than just business.”
For Carlie’s part - she serves as a sounding board for Enrico and offers him as much help as she can. She did mention that should Enrico get the opportunity to ring the bell at the New York Stock Exchange one day he must thank her first and foremost.