Older Entrepreneurs

I Co-Founded a Silicon Valley Startup in My 50s. These Are All the Lessons That Brought Me to Where I Am.

Older entrepreneurs know a lot about how business, culture and leadership work.
I Co-Founded a Silicon Valley Startup in My 50s. These Are All the Lessons That Brought Me to Where I Am.
Image credit: Caiaimage/Lukasz Olek | Getty Images
Guest Writer
Co-Founder and CEO, NakedPoppy
7 min read
Opinions expressed by Entrepreneur contributors are their own.

Thirty years have flown by since I landed in Silicon Valley, where I've been an executive at companies like OpenTable, Amazon, Eventbrite and Upwork.

Related: Success Can Come at Any Age. Just Look at These 6 Successful Entrepreneurs.

Here in the Valley, the narrative of the young entrepreneur has taken hold, while older people fear aging out. It saddened me recently to hear a 50-ish CEO refer to himself as a "dinosaur" while an entire gaggle of workers flourished outside his office.

So, I decided to tell my story.

I just turned 59 and am co-founding a company.

Does this surprise you? If it does, consider this: We're living longer, healthier lives. Does passion age out? Does good work go bad? In fact, studies show that the average age of successful founders is 40, and twice as many founders are over 50 as are under the age of 25.

I'm starting a new business because the idea has wrapped itself around my soul in a way I've never experienced. And my children are grown, so I can work as long and as energetically as I want.

Related: I'm in My 60s -- Proof That It's Never Too Late to Launch a Startup

But there's another reason. It's so simple, it might seem stunning: When you're older, you understand business, culture and leadership in a deep way. You've seen more, period.

More success and more failure.

More of what inspires spectacular work.

More growth surges, layoffs, acquisitions, IPO filings, melodrama and calm.

More ways to skin a cat.

To anyone of age, here's my question: Have you ever been more qualified to run a company than you are now?

Related: Mid-Life Founders Aren't the Exception, They're the Rule

Of course, I'll make plenty of mistakes. But armed with many years of observing how companies are built, my judgment has been honed by invaluable lessons along the way. These include:

1. It begins and ends with people.

The people may not be the only criterion for joining a company, but it's hands down the most important one. Great people love working together. They remember each other. They intersect and re-intersect through the years.

And when you're in the presence of a great leader, you get to observe what makes him or her successful. Put your finger on it. Write it down to make sure you can describe it. Jeff Bezos, for example, elevated customer obsession and creative problem-solving into the stratosphere. What was it worth to observe that up close? Priceless.

Once you understand it, you can figure out how to become it.

Related: How Older Entrepreneurs Can Turn Age to Their Advantage

2. Culture is set at the top.

Anyone who's been through a CEO change knows that a new person can flip the culture, sometimes overnight. 

Microsoft founder Bill Gates used to famously rock when deep in thought. Observers noticed that his deputies rocked too.

I've seen it. If the CEO has loose morals, it'll filter down. If she's constantly brimming with new ideas, the culture will tend toward frenzy. If she's thoughtfully prioritized, it will lean toward calm. You get the idea.

If you're starting a company or leading a team, your behavior sets the tone. If you're deciding whether to join a team, investigate the leader.

Related: One Day, You'll Be 50 or 60 or 70, and You'll Either Have Achieved Your Dreams -- or Not

3. Humans need their work to matter.

Every team member must believe -- wholeheartedly -- that his or her contribution has meaning.

At Upwork, for example, we could have said we were building the best freelancer platform. Instead, we described how freelancing offers freedom and opportunity the likes of which the world has never seen. Which is more likely to make you walk through walls for the customer and business?

4. They also need to know that they matter.

I recently got the following email reply from someone I'd thanked for her brilliant work: "Thank you for your thank you. I'll only say it once since it's kind of silly, but it's important to let you know that something so basic goes a long way."

Wow. How much fabulous but unthanked work is out there? How often will your employees and colleagues reach for the stars if they feel underappreciated?

People know when their managers genuinely care about them. The late Bill Campbell was the first Silicon Valley CEO I worked under. He famously knew the names and concerns of everyone in our 300-person company. I was a product manager but convinced I was his most important employee. In fact, I was sure of it. I left no stone unturned in order to impress Campbell.

Related: Midlife: Time for a New Start, Not a Crisis

5. There's no shortage of ideas, just a shortage of excellence of execution.

Think of all the work you do. How much of it meaningfully changes the trajectory of your business? 

Twenty percent of the work drives 80 percent of the result. Of course, this is not a quantified fact, but a framework for thinking about priorities. Identify the "20 percent" that matters and ruthlessly prioritize only that. Call the long list of remaining ideas "very nice to have" and let them go. I know it's painful. It's far more difficult to narrow your priority list than to lengthen it.

In the early days of OpenTable, for example, we made a tough decision. Instead of continuing to pursue endless opportunities, we focused exclusively on four cities. No matter the temptation outside the four cities, we resisted. It was difficult. But the company succeeded, one city at a time. The same team that was once overwhelmed became calmer -- and their work got better.

Related: Older Entrepreneurs Who Fight Fear Find the Bravery to Embrace Hope

6. Talking to customers constantly is part of the "20 percent" in point 5.

The mark of a great brand? When your customers believe, "This company understands me!"

How do you get into your customer's DNA? You're always, always talking to them. Understanding their motivations. Feeling their pain. And artfully mediating the difference between what they say they need and what they actually need.

At my new company, NakedPoppy, we did three customer studies before we raised our first dime. We now try to talk to customers every day. Sticky notes with their comments are all over the walls. No friend, family or neighbor is spared the questioning. Still, we should do more.

7. If you're the next Mark Zuckerberg, ready to found a company at a tender age, have at it. Otherwise, start by learning from others.

If you just emerged from college and feel pressure to start a company, you might just exhale instead. Of course, you don't need to take as long as I did. But you can use your youth to hone your skills at someone else's company.

Inhale the experience. Observe and articulate what makes your favorite colleagues and leaders great. This knowledge will help make you great.

As for me? I've never felt more ready or excited to start a company.

Related Video: Why It's Never Too Late to Start a Business

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