🔒Q&A: Inside Rucker Investments

The Worcester business community was largely unfamiliar with Clifford Rucker when he launched Worcester Railers Hockey Club in 2016. Now, his Beverly-based company Rucker Investments has become one of the most prominent firms in the region, with stakes in real estate, sports, event venues, restaurants, a startup accelerator, and – as of May – the publications Pulse Magazine and CM Pride Magazine. Jacob Rucker, son of Clifford and one of seven Ruckers at the firm, serves as its private equity analyst. He sat down with WBJ to offer some insight on family, finance, and why Rucker Investments keeps choosing Worcester.

What does your average day look like?

My day-to-day varies, which is why I love it so much. I get to work with my family, which is a blessing and a curse. The family office is a traditional one; we don't manage anybody else's capital. We use our own balance sheet to take risks. Sometimes those risks work out; sometimes they don't. We have residential holdings, operating businesses – a lot of which are based in Worcester – and then an alternative asset portfolio that includes real operating businesses and venture capital. One of our biggest holdings in the City is Auxilium Worcester, which is effectively the only incubator and accelerator in Central Massachusetts with private capital backing.

How has Auxilium been developing since its launch?

We’ve made great strides, and that credit really goes to the team. Worcester isn't very well known, to be honest, even though it's New England's second-biggest city. We're working step by step to take down some of the roadblocks the industry has faced, working through investment and community, and working alongside the people who are physically there. There's the Massachusetts Biomedical Initiatives incubator with Jon Weaver. He's been in Worcester a long time and is really excited about the momentum in the biotech and healthcare space. I went to an event in Cambridge that he put together, and it was really cool to see that even in Cambridge, folks are interested in Worcester. That was a reassurance that we're ruffling some feathers.

What has driven the firm’s consistent interest in the Worcester market?

The community has welcomed us, kept saying they support us, and want to see us make an impact. That's really what keeps us interested in Worcester. At the core of it is the Worcester Railers. That hockey team and the community that followed it – the fans, the people that come to games – that was the nucleus of our involvement in the city. It all stemmed from that. I like seeing new people come into the city and experience it for the first time. Every new person that comes into Worcester is a win for the whole city.

How do you go about discovering investment opportunities?

It's opportunistic. There are always people looking for capital, and Worcester has largely been a drought for capital. If I see an interesting company, I have no problem reaching out. Usually, folks realize we are not a venture capital firm. We're not a private equity firm. We are local investors, and we believe in community as much as we believe in return. Those are hard to come by, especially in the financial services industry. Not all private equity people are bad, not all venture capital people are bad, but there aren't a lot of them on Wall Street with that mindset.

How does geography play a role in your investment decisions?

My preference is New England investments. I'd love to be able to drive to our investments. My generation has largely lost the face-to-face piece. I personally like being with people – at the factories, at the real estate, with the teams – because that gets lost on Zoom. But like I said, it's opportunistic, if there's a community investment somewhere else that just feels right. There's actually a consumer-packaged good (CPG) investment, a Mexican family-owned coffee brand in Washington, D.C., that I really like and is a feel-good investment.

What spurred the interest in purchasing Pulse Magazine and CM Pride Magazine?

Central Massachusetts has long been an under-represented media market, and Pagio's titles already carry real trust in the community. The chance to build on that foundation and give the region a stronger platform for its own lifestyle, culture, and entertainment is what made it compelling. Having Kate McEvoy lead Merit House Media means it's in the right hands to grow the right way.

Why did the firm choose Boston as the place to expand Off The Rails?

The Worcester location has shown there's genuine appetite for a great gathering spot tied to live experiences. Bringing that to Boston felt like a natural next step. With Chris Besaw leading the charge, alongside the hardworking team that keeps the food and service top notch, it should be an exciting one.

Are there other investments Rucker is particularly excited about right now?

I'm proud of all the investments we've made, whether they've done poorly or done great. But there is one I really like: A woman named Joanna Shu in Marblehead created a startup that deals with lice spray and prevention kits. She launched in 6,000 Walgreens nationwide, and she's doing really well. We closed on that investment in December, and I'm happy with her progress so far. It's an example of the kind of CPG investments we want to continue making. It's about backing the jockey, not the horse.

Was it always your plan to work at a family office? What's that dynamic like?

After college, I wanted to work for a corporate company first, to get a feel for whether I liked it or not. I worked at some of the big banks and felt that it wasn't me. I wanted to take a more creative path that felt a little restricted in that environment. Working with my family is awesome. There's a fine line being upset with your brother for not doing the dishes at home and bringing that up in a meeting. It's a balance, but I like it. I'm very grateful and blessed to have the ability to invest where I want and in what I want.

Is there a roadmap for your future at the company, and how do you divide things up among the siblings?

We all have our own personal interests. My brother Josh has a portfolio company he works with at the family office; he has a watch boutique that's doing really well. My younger brother Jared works with me in the CPG space. Jenna is part of the logistics team of a portfolio company. Jess is very much involved in real estate. We're not going anywhere anytime soon. We're still very interested in Worcester and New England. We all tackle different things, and so far it works out really well. EDITOR'S NOTE: This is a extended version of "Inside Rucker Investments," which was published in WBJ's June 22 edition.  This interview was edited to length and clarity by WBJ Managing Editor Eric Casey.