In Praise of the Experienced (Okay, Older) Founder and CEO

Experience pays off.

That was the theme of last week's New York Times story on so-called encore entrepreneurs, which noted the impressive growth rate of founders over 50 in the state (growing at twice the rate of the 50+ population).

Please, will someone alert Silicon Valley that experienced founders can bring not a second wind, but a tailwind, to new ventures?

Let’s be frank: that Silicon Valley has a diversity and inclusion problem is not particularly new or revelatory. (Absolutely no one can say the white-Asian-male-cofounders-from-Stanford model is an untapped pool of value).

Of the select few qualities the Valley seems to prize the most, youth feels like one of the most fetishized. But being swept away by the energy and creativity of the young too often comes with a disquieting byproduct: the discounting of the experience and wisdom of leaders who happen to be older.

It shouldn’t happen that way, of course, but it does. And it’s a real problem - first and foremost for those denied funding for great ideas or rejected for opportunities that would perfectly fit their skills and abilities. But it’s also a significant misstep for VCs and founders whose companies would benefit from capable leadership born of experience.

We can imagine the reasons - conscious or subconscious - that elevate younger entrepreneurs and leaders in the minds of Silicon Valley’s kingmakers. Fewer family obligations mean more time for work. Open to working for less cash and bigger delayed upside. Unburdened by ‘big company’ experience and the old ways of doing things. More natively familiar with the latest technologies. Fresh perspective. Energy, enthusiasm and vigor.

Some of these aren’t truly upsides - for example, prioritizing hires with fewer family obligations won’t actually result in a welcoming and productive culture over the long term. Similarly the positives above (e.g. fresh perspective, energy and enthusiasm) aren’t the exclusive purview of the founder in her 20s.

I’ve had the pleasure of funding, hiring and working with highly experienced leaders (about half of my fund’s portfolio companies are run by CEOs who are 39 and up). In my experience, for every one of the (easily deconstructed) arguments you might make in favor of younger workers, there are good ones for leaders over 35.

Their networks may be deeper, broader and therefore more useful. These individuals have had time - years! - to build and nurture meaningful, long-term relationships. That translates into the ability to get really solid advice, call in favors, recruit, raise funding, collaborate and partner, and more. In contrast, a new founder at the start of his or her career is also in the first stages of constructing that network - there might be a lot of LinkedIn connections but how many of those have influence? How many of those will respond to a call? And how many of those can or will provide something of value?

More experienced workers may have pragmatism and perspective. They might not fall so swiftly into the “more hours = better work” trap, instead understanding that it’s about working smart and hard. They may be less driven by titles and more inspired by opportunities for growth and the rewards (monetary and otherwise) commensurate with stretching oneself.

Self-awareness matters. Sometimes self awareness comes after being tested in significant ways over long periods of time. Newer founders aren’t always clear on their strengths and weaknesses, the personality traits of their co-founders and leadership team that would best complement their own, and even how they might come across to investors, partners and their own staff. This can rapidly become relevant in several ways, for example, with cofounder toxicity, a start-up killer that’s fundamentally an introspection issue.

Foundational technology is useful. If some argue that newer founders are more natively familiar with recent programming languages, you might also argue that leaders with decades of experience might be deeper in foundational tech like C++. Those skills are not to be downplayed - and can support the evolution of excellent innovation.

There are instances where companies have gone (or are going) public led by older founders and CEOs - Zscaler, Workday, Zuora, and Adaptive Insights, to name a few. It’d be nice to see that number grow.