Cross-Generational Cofounding Teams

Updated: Jun 24, 2018

My cofounder Alan and I walk into a small conference room to greet a reporter. She’s interviewing us about the technology startup we’re building, called

As we shake hands and exchange polite smiles, I notice her glancing around the room before she looks back to us. It’s clear from her intrigued expression that we’re not the cofounders she was expecting.

We can’t blame her, though, because we’ve seen it before. It’s a common reaction to the unusual dynamic that makes up our team. Alan and I both attended Washington and Lee University. I graduated in 2014. Alan, in 1970. Cofounders Dillon Myers (left) and Alan Gibson (right) pictured above.

“I may have gray hair,” Alan says to break the ice, “but I self-identify as a millennial.”

She laughs. It’s not so much that Alan is older or that I’m fairly young – tech entrepreneurs span every generation - but she’s captivated by the idea that we’re partners.

Millennials vs. Boomers

Every generation has its own merits as founders, specifically in tech. There have been numerous studies and analyses by VC firms, business schools and think-tanks to determine whether age and experience are indicators of success, but the results are conflicting.

If we’re judging by frequency, entrepreneurship among 20 – 30-year-olds is at an all-time low, despite increasing interest in the field. In the same report, the Kauffman Foundation finds the tech entrepreneur’s average age skews older to 39 years, and baby boomers (ages 52 – 70 years old) are twice as likely to launch a new business as millennials.

However, if we take a look at prominent successes, the largest tech companies today - Google, Facebook, Apple and Microsoft - all had founders under 25 years old at their outset. Even within Silicon Valley’s most prominent incubator, Y-Combinator, the average age of their recent class of founders is 26 years.

There are a few more indicators from Crunchbase, a well-regarded source that tracks startup information. Older founders tend to be more successful at raising money, while companies started by younger founders exit more frequently.

Breaking Down The Generations

Despite the lack of consensus over which generation is better suited to start a technology company, there is consensus over the unique benefits and challenges for each generation, and why a difference exists.

I’m a “millennial”.

My first two years out of college, I was fortunate to be a part of Venture for America. Working within this community was an opportunity to experience the best of the young entrepreneurial spirit. We’re native to technology, have an immense drive to create an impact, and we work tirelessly when building ideas and products that align with our values.

Michael Moritz, Chairman of Sequoia Ventures, describes himself as “an incredibly enthusiastic fan” of talented millennials starting companies. His reasoning is they “have great passion. They don’t have distractions like families and children and other things that get in the way of business.” In other words, they can throw themselves into their work.

Naturally, a young founder’s shortfall is experience, and the most difficult question can be: where do I start? This question can lead to more innovative thinking, but it also presents challenges. Younger founders tend to lack a strong network, financial resources and domain expertise – all assets that generally come with experience.

The Boomers

Through collaboration with Boomers, I’ve realized how much value there is in extensive experience. It may sound obvious, but having already started a company, faced similar decisions and overcome comparable challenges grants a type of wisdom that first-time founders can’t possess.

Straight out of college, I came on board as the first full-time hire for a serial entrepreneur’s new endeavor. Through our collaboration, I watched how he navigated the nebulous fundraising process and I learned the importance of maintaining a strong network. There were even great takeaways in the small details. Through his guidance, I better focused my energy and drive on specific tasks that produced the most value for our company’s growth, while avoiding costly rabbit holes. It’s an efficiency that comes from knowing what has and hasn’t worked in the past.

The challenge for this group of founders is time and energy. Boomers are working till later ages in life than prior generations, but the amount of time spent on their work tends to diminish. According to data from the Kauffman Foundation, the percentage of Boomers working less than 35 hours a week has grown to 48% (from 19% at earlier ages).

Merging Youth With Experience

If cross-generational cofounding teams are not becoming more common, they should be. There is little written on age diversity among tech cofounders and no readily available studies. This is surprising because it’s an intuitive and powerful dynamic: merging youth and energy with the wisdom of experience.

I know this dynamic has been incredibly valuable for my current venture, and not just for the aforementioned reasons. As we continue to find ways to build value for our users, we know that incorporating diverse perspectives, skills and cross-generational understanding will help us reach our full potential.

Younger generations are more interested than ever before in entrepreneurship, but are less likely to actually start a company. Older generations are continuing to work later in life, but are less focused on putting in the long hours. If more collaboration occurs between the generations, everyone wins.