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A Guide To Bridging The Generation Gap

by Ben Kubic

I’m 28 years old. My co-founder is 3 times my age (Jude: Shut up Ben. I’m 52, not 84). I have an MBA from Harvard. Jude never finished her college degree. Jude started her first company with a typewriter. I just learned what a typewriter was while writing this article (Jude: You know that’s not true).

On paper, Jude and I embody the “generation gap”, a struggle discussed ad nauseam in corporate HR departments: Millennials and Baby Boomers are too different to work together effectively. Millennials are the self-absorbed generation that thinks a Masters in Social Media is a real degree. Baby Boomers are antiques who still use MSN email addresses and have landlines.

And yet, a year and half after founding Virgent Realty, Jude and I have one of the strongest co-founder relationships I know. We share excitement in the company’s successes, talk each other up after our failures, and provide direct feedback to each other, no matter how uncomfortable, while still maintaining mutual respect and enthusiasm.

So how have we bridged the generation gap in a fast-moving startup?

Assume Good Intentions

Given that Jude started her career communicating via telegraph (Jude: Why did I let you write this article) and I’ve been coding since I was 10, it should come as no surprise that Jude and I sometimes disagree on how the company should run. However, even when we disagree vehemently, we always manage to maintain a good relationship because we assume good intentions.

This outlook is much more of a mental shift than most people give it credit for. Assuming good intentions means, no matter how upset you are or how wrong you think your partner is, knowing with certainty that their actions come from a belief that what they are doing is best for the company.

Assuming good intentions is why I can tell Jude, a seasoned executive 25 years my senior, that she needs to spell check her work more. It’s why she can tell me, an experienced manager with a master’s degree in Management, that I need to be better about respecting work-life boundaries. When you know that your partner means well, it’s difficult to get upset to the point that your working relationship falls apart.

Play to Generational Strengths

While much has been written on the differences between Millennials and Baby Boomers, few articles have highlighted how this diversity can play to your advantage, especially in a startup where resources are tight.

I’m recently engaged and just over a year out of graduate school. I’ve never owned a home (some irony there) and don’t have any kids. Jude, on the other hand, is recently divorced, has owned multiple properties for decades, and has children in both high school and college.

At first glance, this it would seem like we’d speak two different languages – but it has been a huge asset given the breadth of people we’ve had to work with to get where we are. When we have a first meeting with a potential partner who’s in his 50s and has two kids, Jude can break the ice by talking about the school system. When we work with a client selling his bachelor pad, guess who takes the lead?

Millennial founders often struggle to connect with vital partners and investors at senior levels because they don’t have common experiences in common. Having a co-founder who can both reach and relate to those partners can significantly reduce the barriers to getting a company off the ground.

Baby boomer JudeSet Priorities

As a Millennial, I grew up in an instant gratification world. But when Jude first started in real estate, the Multiple Listing Service — the database of all homes for sale in an area, which of course is now updated online in real-time — was literally a book that came out once a month (Jude: This… is actually true. I’m really old).

If the book came out on the 1st and your home was listed on the 2nd, almost no one would know about it for 30 days.

These backgrounds have led Jude and I to prioritize differently. When I first started Virgent, I thought everything was urgent. Every email needed an immediate response, the feedback we saw most recently was top priority. Jude saw timelines as more malleable. My attitude drove Jude crazy because it meant we were always in demand, even for unimportant things; she frustrated me because I felt like communication delays would result in missed business.

Things improved significantly after we discussed priorities. Now I send emails on the weekend knowing that most don’t need a response until Monday. Jude knows that when we promise a home valuation within 24 hours, 26 hours isn’t good enough.

Interestingly, these generational differences also had a big impact on our product. Younger homeowners are used to getting information on-demand, which is why we built our valuation dashboard technology to deliver information instantly. Even though our company culture blends aspects of both generations, our product can still be generationally targeted.

Our experience has shown that the generation gap doesn’t have to be a detractor, but a strength. By erring on the side of over-communication and establishing shared goals up front, Millennials and Baby Boomers can overcome differences in their working styles to form functional teams and exceptional startups.


Ben Kubic is the co-founder, along with Jude Rasmus, and CEO of Virgent Realty, the better way to sell your home. Read more about them here.

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