From Dorm Rooms to Boardrooms – Josh Greenberg

Josh Greenberg has known Alpine Founder and Managing Partner Graham Weaver since their days at Stanford GSB. He still remembers when building a people-focused private equity firm was more dream than reality. Now, after a successful company exit and a stint outside of Alpine, he’s back in action as CEO of TEAM Services Group, a provider of household employment and home care solutions through a family of companies across the U.S. Josh shares why he took a risk with Alpine in the early days, why the CEO-in-Training program is “pure gold,” and how aligning business wins with impact on individuals is the goal that inspires him most of all.

Tell us about your background. How did you discover Alpine?

I never thought I would go into business at all. I grew up in Boulder, Colorado. I had longer hair. I thought I was going to do ski patrol as a long-term career. I worked in public finance right out of undergrad, raising money for government institutions. Then I started working at Charles Schwab and got really interested in business. So I applied to the Stanford Graduate School of Business. I had this feeling that I  wanted to be a part of something special and to write my own story. And I had an aversion to being part of the machine, like a cog in the wheel of a much larger organization.

Then I met Graham Weaver. Graham followed a similar track at Stanford, and we both admired one of the professors there, Irv Grousbeck, who pioneered entrepreneurship through acquisition. Irv was definitely a very formative professor of mine, and we bonded over that.

Graham believed that if you find the right people, put them in the right seat, and give them the autonomy and tools to be successful, you’ll win.

Meanwhile, Graham was building Alpine. I remember having this great discussion where he was sort of laying out the potential groundwork of us partnering together in the future. He took almost an academic approach to it. He had a winning formula and did extensive research on people like Warren Buffet. Graham believed that if you find the right people, put them in the right seat, and give them the autonomy and tools to be successful, you’ll win.

What drew you to working with Graham?

Stanford was a remarkable experience, because it’s a curated existence. People took the time to consider who they wanted to be during their time in business school. In a lot of ways, I know Graham took something  from that, because it’s the way he built Alpine. He’s been so deliberate and thoughtful about the way Alpine hires and retains talent.

I think we also gravitated toward one another because we have complementary skill sets. As an operator, I really wanted a seat at the table and to actually try my hand in general management. Graham approached building Alpine from an investor’s perspective. He’s great with sellers, tax orientation and motivation, and negotiating. By that point, specialization had become a mantra for my career. Graham assured me that together, we could find a great company and structure it so that I could take an operating role. I was excited about Alpine’s deep, embedded respect for the managers and operators of the business. I think that’s why Alpine has such a leg up in buying founder-backed companies. The Alpine team relates to founders.

I think that’s why Alpine has such a leg up in buying founder-backed companies. The Alpine team relates to founders.

Leaving business school often feels like a career-defining moment. How did you decide to take a risk with Alpine, a brand-new private equity firm at the time?

I remember reflecting on my life based on my resume. I had this great list that included student body president, varsity athlete, good college, good extracurricular activities, and then Stanford. I remember feeling like I was on an attractive track, but if I looked up that track, I didn’t have a fire in the belly enthusiasm about my future. I didn’t see the story I wanted to write about myself.

With Alpine, I would have the chance to partner with somebody who I really respected, and I would have true ownership over something. It was scary. I realized we might buy something that was working, and if it stopped working, we would have broken it. I knew I was taking a lot of risk, but if I was going to take risks, I wanted to surround myself with great advisors.

I partnered with another friend from business school, John Fowler, to search for a company to buy. Graham seeded our search out of Alpine’s first fund. We bought Aero Logistics, a specialty shipping company, and he invested as the anchor tenant in the company. He invested in Aero out of Alpine’s fund two, so we got to work together right out of the gate. At the time, I had no idea that you could put yourself in a position of general management at an early age and surround yourself with the right resources, all with the backing that comes from a good investor group.

Describe those early days running one of Alpine’s first-ever portfolio companies.

The seeds that make Alpine unique today were planted back in the beginning. I never felt like I was working for an investment fund or private equity firm that was going to just call the shots. Every call was collaborative. Even big, internal decisions like when to sell the company were conversations. When it came time to discuss selling, Graham called and said, “Hey, I’ve never seen such an attractive window. You’re really thriving. It would be a great time to sell, but what do you guys think?” We had a much better outcome because we were so engaged in and enthusiastic about the process.

It felt like Graham had my back, not just as an investor, and not just for the financial return, but as a person. I felt like he cared about my professional development. Graham and the rest of the team approached each deal like servant leaders. They invested in each team, and their job was to help that team succeed. Their approach had an intangible, softer element that felt truly motivating; it made me want to walk through walls. Alpine backed up their emotional support with tactical support, too. I felt like I had good instincts on people management, financially managing the company, selling, and all the blocking and tackling of operating the business. But Alpine could dig in and provide a force multiplier in the areas where I felt less comfortable.

You brought Aero Logistics to a successful exit, and then you left Alpine. What factors informed that decision?

When we sold Aero, there was no question in my mind that I would work with Graham again. Alpine gave us the space and autonomy to do what we could do best, which was just to sell things and grow the business. We grew it five times in a period of about four years. I was proud of the great outcome for investors, and I was energized by the massive validation of how you can do things the right way and succeed.

I was excited to do everything I needed to do to get the maximum value for Alpine, which included continuing to run Aero Logistics after they sold. I ran the business for a while, but because I had stacked the deck with amazing people, I was  quickly able to leave the business in good hands.

At that point in my career, I made a commitment to start working on things for which I felt a personal passion. I fell in love with an investment thesis in the healthcare space. John and I founded a healthcare services startup, HealthCPA. I also served on some boards and got exposure to other institutional capital. We had good outcomes and learned from a number of different industries.

How did you choose to return to Alpine to run another portfolio company?

I always knew I would work with Graham and Alpine again. Fast forward through those four-or-five years of management, and we sold HealthCPA in 2014 to a large-revenue-cycle management company. I realized it was time to get the band back together. Around that same time, we found TEAM Risk Management Strategies, a provider of outsourced employment and risk management services, which was a perfect overlap of what I’d been doing in healthcare. TEAM had elements of risk management and insurance. It was a unique opportunity for me to take the helm, and it was a perfect opportunity to get back to Alpine.

You’ve hired several CITs as part of TEAM. What stands out about the CIT program?

The CIT program takes people who are younger in their management careers and gives them the resources and more importantly, the opportunities to show up as CEOs in their own right. The first CIT that I hired at TEAM was Rachel Green. She joined six months into my tenure, and we immediately fit. She has great instincts and a hunger to learn.

At the same time as Rachel joined, Cullen Knights came to TEAM through Alpine as well. The combination of Rachel, Cullen, and then eventually Marcus Bradley created an unstoppable management team. I remember a really proud moment at a meeting with a group of very traditional bankers. One banker said, “That was remarkable. There were basically three CEOs in that room.” For me, that was the most wonderful testament to our team. To be surrounded by people who could do my job equally, if not better than me, was a wonderful affirmation of their relationship to the company and their readiness to take on CEO roles.

That feedback proved the value of the CIT program in my eyes. You take individuals who are earlier in their careers, surround them with the resources and more importantly, the opportunity, and all of the sudden they show up as CEOs in their own right.

Rachel took over your role as CEO of TEAM. How did you know it was time to hand her the controls?

Alpine was investing in Rachel, too. I love the fact that my professional development work with her was augmented by the CIT program. I think the support that she got from me and from Alpine allowed her to do what she was going to do anyway, which was to be an incredible leader and addition to the team.

Rachel was rigorous about professional development. We talked all the time about getting her experience and filling in the gaps. We talked about what worked and what didn’t work, and we always discussed lessons learned. Our partnership made it remarkably easy for her to take over as CEO of our fast-growing, dynamic business serving a big bank institution. It’s a big job. She’s hanging out in the boardrooms of the U.S. Trust Company, Bank of America, and Wells Fargo. But I had zero hesitation about putting her in the CEO seat.

Alpine is so good at assessing a person’s internal horsepower, drive, and talent. There’s something special about giving CITs room to run and never stifling their drive. The CIT program is solid gold.

What do you love about TEAM and the home health industry? What are you most proud of over the past five years?

I feel personally engaged in our mission—to provide care to people in a home or community-based setting. We have the opportunity to make a massive, notable, societal impact and to improve people’s lives. Our model has saved many lives in the COVID-19 environment by keeping people in homes instead of institutions, and by providing one-to-one relationships with caregivers.

The stories of our customers are incredibly motivating. There’s a young man who was spending his life in a hospital bed. We moved him to Colorado and got him set up with his own place and his own care team. Now he’s out and about in the community every day, and he works for our company. Now he has a fulfilling, meaningful life.

Beyond impact, this is a scalable model that’s going to have wind at our backs for decades to come. I’m motivated to deliver value to Alpine, and I’m also committed to the colleagues who have given their time to be in the trenches with me and to help build this business. They are my winning formula.

What’s next?

If you find something that’s working, I am always a fan of pouring more fuel on the fire. TEAM scaled by over 10 times in revenue over five years, and we continue to grow. Today, we’re serving 20,000 families across the country.

A company is only as good as the people.

A company is only as good as the people. People can scale only so far. In order to continue to grow, we need to keep back-filling, and we need to give good opportunities to great people. The most rewarding thing for me is to get out of someone else’s way and to let them take the helm. We’ve had a pretty remarkable story over the past five years, and there is a lot I’m proud of from a financial perspective. I’m much prouder of the footprint we have, the communities we serve, and the actual people that we care for. The fact that we generate profit by doing good work is, in my estimation, a pretty exceptional opportunity.