Startup success rooted in connections

Business People and Community

By Michael R. Malone [email protected] 07-13-2026

Bennett Richter's first job-as a teenage ice cream scooper in Minneapolis, Minnesota-taught him all he needed to know about the challenges of working for someone else.

"The work is hard, I don't get paid enough, and my schedule is so restrictive," he complained to his mother about his summer job.

His mother, who had traveled quite a bit and was no stranger to adventure, leaned on the family ethos-take risks and push boundaries-and challenged him. "Why don't you start your own company window or power washing for people who have summer homes?"

"That's where it sparked-I got my first taste of entrepreneurship," Richter said. "I ended up servicing nearly 100 homes with two employees working for me over four or five summers. That first taste addicted me to what it felt like to control your own business."

Richter, who graduated from the University of Miami in 2022 with a B.B.A. in entrepreneurship, has followed his entrepreneurial spirit ever since. After garnering sales experience for a few years after graduation, he moved to San Francisco to join Lassie, a Silicon Valley startup. In his 19 months there as the founding sales lead, he's helped the company grow from six employees meeting in a garage to 20, inspired by its AI-powered medical office automation systems.

The company recently announced a Series A funding round led by Andreessen Horowitz (a16z), a venture capital firm known for bold investments in firms such as Airbnb, Instagram, and Meta.

"When you get Series A from a company like Andreessen, it changes things overnight," said Richter. "Now we need to go from 20 to 100 employees within months in order to be one of these hyper-growth companies that go viral in terms of revenue."

The adventurous spirit he had demonstrated as an entrepreneurial teen prompted Richter to leave the Midwest to attend the University of Miami. Once here, he vigorously pursued networking opportunities and credited his professors and classes with honing the skills, tools, and confidence that have buoyed his professional success.

Susy Alvarez-Diaz, assistant professor of professional practice in Miami Herbert Business School's Department of Management and former director of the entrepreneurship programs, remembered Richter as a stellar student. She highlighted, too, that his success in securing backing from such a notable firm marks a milestone for the business school's reputation as well.

"Bennett was very much an intellectual, not in the book sense, but in his curiosity in finding the why of things and always questioning: 'How can this be done cheaper or faster or structured differently?'" Alvarez-Diaz said. "When I see that, I know that here's a student who's going to do great things."

Alvarez-Diaz highlighted the role of another exceptional former student, Jason Shuman, who graduated in 2013 and has developed a key mentorship relationship with Richter.

After graduating, Shuman went on to become a partner in New York City with Primary Ventures Partners, one of the world's largest early venture capital firms. Like many alumni, he returned to Miami Herbert to lecture and meet with students.

"Back when our entrepreneurship program was starting, all the industry success was from the Ivy League school grads-and we were committed to change that," Alvarez-Diaz said. "Jason was the first one to get his way in. 'Okay,' I told him, 'You're my inside man. We're going to be tossing students to you-you have to set 'em up.'"

When Shuman visited his senior class and shared some of his insights and experience, Richter was immediately impressed and knew that he was someone to learn from.

"I called him the next day to meet for coffee, and he was pretty much 'I've got 20 minutes, and I'm up in North Brickell,'" Richter remembered. Richter ordered an Uber and was at Shuman's hotel in short order.

At the time Richter was interning with Boat Setter, a startup like Airbnb for the yachting and marine industry. He was learning a lot but felt the need to push his boundaries more. The two established a good rapport and agreed to stay in touch.

A few months later, Shuman called him. One of his better portfolio companies was growing and needed their founding salesperson. Was he interested?

"I took the job and that was where the mentorship really fully kicked in," Richter said.

Richter flourished under Shuman's guidance, using his communication and sales skills to support several ventures. Through one of the initiatives, he developed a close relationship with Jake Butler, one of the early sales hires for DoorDash and who was starting an incubation company under Primary Ventures Partners.

A few months later, Butler offered to introduce him to the Lassie team in Silicon Valley. Richter declined at first, not wanting to compromise his allegiance to Shuman, but-after accepting an invite to meet with the founders-was ultimately convinced by the exciting new vision.

"It goes back to my earliest point of my mom saying, 'Jump into unknown waters,'" he said. "It's just like a giant tree of connections, and to navigate it, you have to be pretty strategic."

Richter knew he was entering a new professional arena.

"I realized I had the chance to join one of the best technology operators in Silicon Valley, with ambitions to build a multibillion-dollar business," he said. "Suddenly, I was in a different ball game, surrounded by Ivy League graduates and world-class operators."

Not long after joining Lassie, he brought another Miami alumnus, economics major Jamie Aijala, to the team.

"Jamie is a huge part in this and one of the most important pieces to Lassie's success so far," Richter said. "We wouldn't be here today and be able to raise from such a good investor if it wasn't for our combined impact."

Richter highlighted that Lassie's ability to secure major funding signals a new inroad for Miami Herbert.

"What excites me most about this milestone is what it represents for UM," he said. "Too often, the conversation around entrepreneurship, venture capital, and AI is dominated by alumni from places like Stanford, Harvard, and MIT. This is one of those moments that shows University of Miami graduates can compete at the very highest levels, build world-class companies, and earn the trust of the most respected investors in the world.

"In many ways, this is exactly how schools build their reputation over time-through the accomplishments of their alumni," Richter added. "Jamie and I are incredibly proud to be part of that story and to help put Miami on the map as a place that produces ambitious founders, operators, and innovators capable of competing with the best."