It’s Lonely at the Top

Seek out mentors to avoid a chief pitfall of the job

A few years ago we asked founders we invested in to tell us what was on their minds. We were planning a summit with them and sought their feedback on what we should discuss.

One topic bubbled to the top: mentorship. It’s perhaps the most important topic for startup founders that hardly anyone talks about.

When you’re a startup CEO—whether you are a first-timer or grizzled veteran—it’s easy to find yourself alone. The reasons for the isolation are multifaceted, ranging from a CEO’s need to carry on appearances that “everything’s great here” to the stealth nature of startups.

If you look around Silicon Valley, though, you’ll notice most successful founders don’t get there alone. They have great mentors.

We encourage all founders we invest in to get proactive and seek out mentors outside of their company—and to confront the obstacles that might hold them back from doing so.

Some founders, like Ooshma Garg of Gobble (who we wrote about in “Founders Come First) set up formal relationships with advisors early on that serve them well throughout their journey. Others, like Jonathan McQueen and Nima Kievan (“Talking AI Robots”) come around to the value of mentors after some growing pains. 

At some point, most great founders find what works for them.

Mentors come in many varieties

A mentor can mean many things.

It can be as simple as a casual relationship with another CEO or experienced business person who doesn’t know you or your business or you that well—but is there to listen. It’s a shoulder to lean on, a sounding board for airing things you can’t say to your employees, a guide to warn you “don’t cross the streams!” from time to time.

On the other end of the spectrum, it can be a formal board of advisors or a formal relationship with an executive coach you hire to get deeply embedded in your business and serves as a Yoda of sorts. 

And it can be anything in between.

Why so lonely

Let’s take a step back and examine the reason founder CEOs find themselves so isolated in the first place.

There’s personality at play. It’s common for startup founders to think they can do everything on their own. After all, they’ve been told all their lives that they can’t!they won’t!they shouldn’t! do something. And all their lives, they’ve proved the doubters wrong. All their lives, they’ve confronted problems head-on and figured it out on their own. If a problem arises, no matter how complex or out of their wheelhouse, they figure it out.

There’s the reality of the position. When you’re a CEO, the buck stops with you. You are responsible for inspiring the team, making the right decisions, hitting your marks. Your confidence in the company’s direction is paramount in recruiting and keeping top talent. There is little room for uncertainty. A seed of doubt can grow to a beanstalk that chokes a fledgling company, almost overnight.

But you are human, and there is uncertainty. 

As CEO, you have a full view into every aspect of the business—which means many opportunities for those seeds of doubt to fester. If you have uncertainty about your ability to raise the next round, you can’t let that impact the product team that’s working to deliver on promises. The realities of your position force you to compartmentalize: things I can say to my team and things I simply cannot.

Outgrowing your mentors

If you’re a first-time CEO, you may have a peer group that has served you well up until this point—people you learned from and consulted in prior roles. Your college roommate may have been great for learning about programming or sales, but if they aren’t waking up in sweat-soaked sheets at the thought of keeping 10, 50, or 100 people’s livelihoods on track, they may not be your best sounding board anymore.

Similarly, if you are an experienced CEO, you may have outgrown the peer group that you navigate the early stages. Managing a team of 1,000 people is a different ballgame than managing a team of 10. This is a common experience because of the accelerated growth of many startups.

There’s also the nature of the startup ecosystem. It’s a cutthroat world where companies operate in secrecy. You don’t want to broadcast your deeply held concerns for your company to people you don’t know. You can’t just put a billboard up on the 101 “STRUGGLING CEO IN NEED OF MENTOR.”

Mentors won’t find you

So what do you do?

The first step is understanding the reality of your position and that there are many others who feel the same—many, many, many others. There is no lack of founder CEOs in Silicon Valley, or elsewhere, to seek out. Similarly, there is no lack of highly qualified executive coaches or veteran executives willing to help a founder fly.

The trick is getting out there. On any given day in Silicon Valley, there are formal and informal gatherings of founders, investors, and others embedded in the startup ecosystem. Get out and find someone who both understands the issues you face in your business and is looking to help. Build mutual trust and gradually peel back the layers of your doubts and frustrations.

If you’re not looking for it, it will not find you.

Our mentors

We’ve been fortunate to have outstanding mentors in our lives. When we were both at Yahoo! we were encouraged us to seek mentors.

For Ash, Farzad “Zod” Nazem, then the chief technology officer, laid out the fundamentals to building effective teams that to this day serve him well. We’ll outline “Zod’s Axioms,” as they became known, in a future article. 

For Mike, weekly meetings with Jeff Weiner, then the head of search and marketplace (now the CEO of LinkedIn) transformed the way he thought about managing teams and complex processes. To this day, Mike continues to get value from weekly discussions with Jeff.  One specific piece of advice he offered: Look for opportunities for ownership. In corporate development, it was difficult to directly “own” anything, because business unit leaders were typically the executives who had the ownership. As a result of the advice, Mike headed the creation of a new executive approval process for acquisitions that made the company significantly more nimble in its decision-making process.

For those feeling lonely at the top, or wherever you might find yourself on the corporate ladder, there’s a lot to learn from Mike’s experience. Companies can play a role in helping their leaders—and future leaders—seek out mentors.

But you don’t have to wait for your company to nudge you. Let us do the same favor for you: Seek out a mentor, formal or informal.

You aren’t alone.

About the Authors

Ash Patel and Mike Marquez are co-founders of Morado Venture Partners, a seed venture capital firm dedicated to capturing investment opportunities in emerging technologies and data-fueled businesses.