I have started five com-panies in education technology and have been fortunate to see several through successful exits. My latest venture launched in 2020 and is now profitable, bringing in $30 million a year.
Here’s my number-one reason for success, and it’s not something you’ll find in a business textbook — it’s a revelation that came to me at my first company, and it’s simple: I try to hire the same people.
I’m not talking about a few top executives. I mean employees at every level. My goal is to have at least 50% of my team consist of familiar faces. At Uwill, the student mental health and wellness company I lead today, we have about 100 full-time employees. Roughly half have worked with me before, and many of those who haven’t came through referrals from trusted colleagues.
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What’s the benefit of this? First, you can be up and running fast. Startups move quickly and you don’t want to waste time finding your rhythm. When we “get the band back together” (so to speak), we have people who already understand each other. They’re not waiting for someone to tell them how to do their jobs. They’re ready to play.
Second, this team has helped scale companies quickly. Whenever I start a new business, I need people who can quickly shift from “scrappy startup” to “serious scale” mode, and be excited about that. There’s a certain intensity in the way we do it. There’s also a lot of autonomy. This environment is not for everybody.
Finally, although all my companies are built with innovative technology, their missions are to contribute meaningfully to users’ lives. When I build a team, I look for employees who put that mission above everything else. Our work is meaningful, and it takes people who care deeply to achieve the impact we’re trying to make. Balance matters, but I’ve found that colleagues who are driven by our purpose and impact also appreciate that work may have to happen at unexpected moments.
I’ve developed a few other tactics to attract former colleagues. When I’m gearing up for a new venture, I’m the opposite of stealth mode. From Day 1, I’m out there on LinkedIn promoting the vision and painting the picture of the business as if it’s already done, so that people know what we’re up to. We can’t always pay top dollar for salaries, but we give equity to every full-time staffer and cover 100% of health benefits. Medical, dental, vision — no one contributes a cent.
Related: Why Your Startup’s First Hires Matter More Than Your Big Idea
The system isn’t perfect. If you want to play devil’s advocate, familiarity can mean people don’t feel the need to prove themselves — that’s real. But we do things to make sure that doesn’t happen. I don’t hire former employees for positions that don’t suit their strengths, and I make sure to bring in outside hires with fresh skill sets and perspectives. Also, part of our growth model involves acquiring smaller companies, so that means absorbing and learning from some of their talent.
We’ll be doing more acquisitions now, because our growth is accelerating. We have a partnership with the state of New Jersey to provide care to all of their higher-ed institutions, and we’re encouraged by new relationships with other state systems and leaders. We’re also seeing a rise in demand for K-12 mental health support. And we’re continuing to grow internationally and finding other new areas where we can support students.
Everyone is excited about our latest acquisition, a company called tbh, which addresses student basic needs like food, housing, and financial insecurity. It shouldn’t surprise anyone that these challenges are deeply connected to mental health.
Having worked with my colleagues for so many years, I know that these milestones are motivating for all of us. And that’s a powerful driver of success.
Related: How Employers Can Assess Job Applicants — and Avoid Costly Hiring Mistakes
I have started five com-panies in education technology and have been fortunate to see several through successful exits. My latest venture launched in 2020 and is now profitable, bringing in $30 million a year.
Here’s my number-one reason for success, and it’s not something you’ll find in a business textbook — it’s a revelation that came to me at my first company, and it’s simple: I try to hire the same people.
I’m not talking about a few top executives. I mean employees at every level. My goal is to have at least 50% of my team consist of familiar faces. At Uwill, the student mental health and wellness company I lead today, we have about 100 full-time employees. Roughly half have worked with me before, and many of those who haven’t came through referrals from trusted colleagues.
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