The Strange Value of Getting Old

Entrepreneur Office Hours - Issue #330

Inside the Office

-Aaron Dinin

Not Jon, but hopefully it’ll get his attention if he reads this newsletter. Photo by Tim Mossholder on Unsplash

Earlier this week we celebrated the retirement of Jon Fjeld, one of Duke Innovation & Entrepreneurship’s former directors and someone who spent a lot of years with me serving as a boss, mentor, and reliable source of advice.

At the end of the event, as people were saying their goodbyes and filtering out, I mentioned I’d love to grab lunch sometime soon. Jon and I hadn’t caught up in a while, and I had a couple projects I’d been meaning to get his perspective on.

Jon laughed and said something along the lines of, “Happy to help, but I’m not sure how useful my thoughts are anymore. I’m getting old.”

It was clearly a joke, but it stuck with me because, the older I get, the more I appreciate the value of “getting old” in a way I just couldn’t seem to understand as a young entrepreneur.

Back when I was first starting my entrepreneurial career, I was convinced I was the smartest person in every room. I thought I understood how things worked. Or, at the very least, I assumed I could figure anything out if I just tried hard enough. As a result, whenever someone told me I lacked experience, I usually heard that as a limitation I needed to push past rather than something I needed to respect.

Fast forward two-plus decades, and even though I almost certainly do know more than I did back then, I feel like I know so much less.

Or, more accurately, I have a much clearer sense of how much I don’t know. I see the edge cases and the tradeoffs that are likely to impact every decision. And I understand how often things that seem obvious at the beginning turn out to be far more complicated in practice.

Thanks that heightened awareness, I find myself craving the perspective of people who’ve been through it before — people like Jon.

And, yes, I promise, there’s an entrepreneurial lesson buried in this shift. It’s a lesson about learning to prioritize experience as quickly as possible, which is something young entrepreneurs struggle with.

Heck, it’s something young people, in general, struggle with. Just look at how quickly they ignore everything their parents say (myself included!).

While I realize, in some respects, that confidence of youth is an asset. After all, in the startup world, you kind of have to believe you can do things you’ve never done before, or you’d never start. However, over time, the skill that starts to matter more than confidence is judgment. And good judgment tends to come from a mix of experience, reflection, and, maybe most importantly, listening to people who’ve already seen versions of the problems you’re trying to solve.

-Aaron

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Worth Your Time

-Shep Moyle

Harvard Business School professor Karim Lakhani is researching how AI is transforming work, companies, and strategy. He argues AI is more than just a tool you use; it’s a teammate you collaborate with. And this goes far beyond automation or efficiency; it changes how decisions are made, how organizations learn, and how startups can compete at scale.

As part of that work, in this video Lakhani posed a provocative idea for entrepreneurs about how AI can drive the marginal cost of expertise down toward zero. In practical terms, that means the smartest and deepest knowledge in a domain is no longer scarce or expensive — it becomes more widely accessible through AI assistance. And when expertise becomes abundant, competitive advantage shifts from having knowledge to knowing how to apply it faster and more creatively than anyone else. He also highlights research showing that individuals working with AI can be as effective as entire teams working without it—a transformative insight for startups where resources are limited.

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Tools We’re Tinkering With

-Jamie Jones

Editor’s note: All resources suggested in this section are based on our opinions. These aren’t affiliate promotions and we don’t generate commissions.

As Duke I&E’s programming has grown, so has the complexity of keeping it all moving. At some point, managing workflows out of our inboxes, spreadsheets, and Slack messages stopped scaling (and adding headcount wasn’t possible… or even the right answer). So, we introduced Basecamp, a project management tool that has been just the right fit for our team. Sophisticated enough that it does the job, but simple enough that we’ve been able to drive adoption across the organization.

All of our information for each project is stored in a single location that anyone on the team can access. The portfolio view allows me to see where every project across the team stands. All of this without chasing anyone down for a status update or annoying them for a lost bit of information I can’t find in my inbox.

The real kicker is the ability to template recurring projects/tasks. We’ve built out SOPs for our major programs — pitch competitions, workshops, mentor office hours — so if someone’s unexpectedly out the week before a big event, the playbook already exists. Someone can step in without starting from scratch.

Having the right infrastructure in place has allowed for less scrambling and enabled smoother and more consistent workflows.