From personal business to family business — my story

Roger Ehrenberg
8 min readDec 27, 2023

Life, even in the most fortunate of circumstances, can be both head-spinning and anxiety inducing. And the more in touch you are with those feelings, the more intense things become. I’ve always valued self-honesty, even if it is painful — which often it is. Even at age 58 I’m still trying to figure stuff out, perhaps even more so as the degrees of freedom associated with life have exploded due to economic independence, striking out on my own and with my kids firmly entering adulthood. When I’ve experienced major life transitions, such as leaving Wall Street in 2004 or IA Ventures in 2021, I have found grounding in talking to lots of smart people. Smart, interesting people, with life experiences and careers different than my own. It is through these conversations along with my own hypothesis-testing that has narrowed the range of future possibilities and brought focus to the proceedings. It was this way when I decided to embark on my two decade journey in technology venture investing, as well as my relatively new vocation of investing in sports franchises, sports technologies and related businesses. Develop a list of areas of interest. Create a set of hypotheses. Road test these hypotheses with lots of smart people. Refine the hypotheses. Garner additional feedback, continue the refinement process. Rinse, repeat. From this process came my thesis around the “Entertainment-ification of sports”, something that has guided my thinking and investing approach since launching Eberg Capital with my sons.

And we’re off…

Now, I get lots of people saying, “Wow, being in business with your kids, that must be a dream come true!” Well, not really. To be honest, it was among the last things I ever thought would happen to our family. I was raised by a guy, rest his soul, with whom I had a terrific relationship the last 15 years of his life but a less-than-terrific experience in the time prior. My dad was brilliant, and at times charming, but was raised by immigrant folk who didn’t do a great job with the parenting thing. He was brash, arrogant and headstrong, and not a very good listener. I wasn’t necessarily an up-and-to-the-right “normal” kid during the years I lived under his and my mom’s roof, and this did not endear him to me at all. In fact, I couldn’t wait to strike out on my own and never look back, to be my own man and to not owe him or anybody anything. I had a chip on my shoulder a mile tall, and boy, was I driven. I still am. But how is this relevant? Because he told me on any number of occasions that he wanted me to work for him in a family business, which is certainly the last thing I’d ever do. In fact, it soured me on the notion of families working together, and it just reinforced my notion that we all needed to do our own thing, have our own victories, develop our own strong self-esteem and be self-actualized adults through our own efforts. And then one day our boys came to me and asked if we could work together. Gulp.

We are a very close family. I met my wife Carin in college. It’s the greatest thing that’s ever happened to me. She has been the great unlock to my potential and has helped me to become the man I couldn’t imagine I’d ever be. She has given me a level of empathy, tolerance and joy in celebrating life that was completely missing from my childhood, and it is she and my therapist (whom I saw twice a week for four years in my 20s) that helped get me beyond the pain and clinical detachment from my most difficult feelings that were holding me back. We’ve been together for more than 36 years. Our two sons are fine young men, ages 26 and 23. We took them to school, got involved in school leadership, coached their sports teams and, in Carin’s case, even ran the entire Little League where they played ball. We were engaged and involved parents to say the least. I am grateful that I was able to shape my career to have the flexibility to do these things, and part of what drove me was not only the love for my children but to be a better father to my sons than mine was to me. I loved it all and it made me proud to feel like a good father and a good man. But the notion of extending this closeness to working with my children was never on my radar screen for the reasons mentioned earlier. I didn’t want to squash them, detract from their victories or to possibly damage the close familial relationship with work conflict. This just seemed like an awfully risky trade and one that I had blocked out of my mind — until I couldn’t.

The boys grew up around a dinner table replete with stories of Wall Street, venture capital, struggling and victorious founders, hard conversations at all points of my career and loads of macroeconomic perspectives from yours truly. This was buttressed by my wife’s highly educated perspective (a practicing Ph.D clinical psychologist) on how psychology — empathy, power, insecurity, and more — played a role in how my stories played themselves out. So our sons really got a nuanced sense of how to think about investing and business building, not merely from a quantitative perspective but from the human vantage point. They witnessed my rise on Wall Street, the massive risks associated with striking out on my own, the unrelenting stress I felt during the darkest days of the GFC (when we had no money coming in and lots going out while seeing if I was any good at seed stage technology investing), and finally the evolution into a venture capitalist who started a successful firm with wonderful partners and a high-integrity approach to doing business. The financial success of IA Ventures, together with my stepping back from the firm, afforded me the resources and the time to begin investing in one of my passions: sports. And this happens to be a family passion shared by my wife and sons alike. So once I embarked on this new career path, following the process of discovery described earlier, I began generating some very interesting deal flow. And I wanted to share this deal flow with my sons to get their perspective, as they are, in many ways, the “voice of the customer”, so richly valued by businesses in and around sports: franchises, sports betting, media and more. And so, unwittingly, I had planted the seeds throughout their lives which culminated in that moment: can I, and should I, work with my children?

Suffice it to say, something this big had to be processed in depth between Carin and me. It wasn’t merely me and my sons working together; it was a shaking up of the family unit. We are already three males and one female in what I’d say is a “boy boy” house: lots of discussions about sports and pop culture; sizing up each other’s muscles and fitness; and “horsing around”. While this isn’t the sum total of our family culture, it is certainly a 30 thousand foot representation. Carin, who herself is an excellent athlete, knows a ton about sports and loves both watching and playing them, is still not crazy to the same degree as we three. And if you add the fact that I am the boys’ role model in work and in life — you can see how introducing a professional working relationship between me and my sons might strain the family dynamic. How do Carin and I maintain enough space for ourselves, avoid family time being dominated by boy-business talk while giving the Eberg business a chance? Oh, and did I mention that our children are themselves very different people: different ages, different strengths, different academic backgrounds, different (but overlapping) interests and different styles. In IA parlance we would describe businesses that had a series of contingent probabilities necessary to achieve greatness as requiring “a cascade of miracles”. Well, it started to look to me like success at both Eberg and with our family would require such a cascade, and my historical baggage and aversion to such an arrangement, together with the obvious family dynamics made the undertaking quite daunting. But in the end Carin and I felt that it was worth the risk. The boys both clearly had deep interest in my work, and would likely have pursued careers in sports or related fields regardless. So if they were going to be in the field and pursuing the goal of becoming investors and business builders, why not learn from their dad who has done it successfully for decades? So we, as a family, decided to embark on this journey provided that: (1) there were frequent check-ins on how things were going; (2) we established a culture where problems and conflicts would be sufaced quickly, and; (3) acknowledged that if we couldn’t effectively handle the needs of business and family at the same time, that it would be the business relationship that would go. And this is how we’ve been operating at Eberg Capital ever since.

But let me be clear: it has been hard. Richly rewarding, a ton of fun, but very difficult to be sure. I am my sons’ manager and mentor. I am responsible for their professional development and growth as investors, networkers, business builders and as relentless, hard workers. I am also their father and their friend. Each boy is different and I am trying to set paths for each of them that leverages their particular strengths, while having them tightly integrated with me and with each other. I am figuring out how to stop feeling worried with the ominous sense that failure is just around the corner and to enjoy the process. It took me a while to “burn the boats” and to stop viewing Eberg (with my boys) as being an experiment but a real business built to endure. There have been bumps along the way but so far we’ve handled it quite well as a family, but it requires vigilance. Now that I feel like we’ve proven we can work together successfully, while maintaining our intimacy as a family, I’ve come to reflect on this process as a healthy one for all of us. And I am so grateful to my wife for having the strength and the perspective to help us all through this. Because Eberg wouldn’t be Eberg without Carin. And I wouldn’t be the man I am without her, either.



Roger Ehrenberg

partner @ebergcapital. owner @iasportsteam & @marlins. founding partner @iaventures. @thetradedeskinc @Wise. @UMich @Columbia_Biz. family man. wolverine. 〽️