The Best Mentors Fade Away
We've got to GTFOOTW so they can take their own Hero's Journey
Welcome to the latest entry in The Captain’s Log. You’re in good company with thousands of fellow entrepreneurs and innovators who have subscribed!
I’m your host, Bob, and my mission here is to share personal, behind-the-scenes stories of ups and downs from my career leading tech startups and corporate innovation.
I write to make you think, smile, and discover a shortcut to success or a trap to avoid.
Here we go…
First-time startup founders feel a lot of pressure to “listen to their elders” when they begin their journeys. It seems the whole startup ecosystem encourages a kind of apprenticeship program.
Many head into accelerator, boot camp, and incubator programs where they are paired with mentors and frequently hear from guest speakers who have been there and done that. Investment firms pitch their teams’ expertise and networks, then promptly set up a board for monthly advising as soon as their checks clear. And you feel like a loser without an Advisory Board comprised of industry experts and potential clients.
Most of these mentors are eager to give advice. They want us to succeed and enjoy telling stories of their battles. But a founder’s head swirls with so much competing input. It’s even tougher when you are counting on these elders for your next round of funding or an introduction to a potential customer.
And there’s a sad tendency to follow all that advice—right out the window.
That’s why the most successful founders learn to figure stuff out on their own. They realize the journey is theirs and theirs alone.
And the best mentors get the F out of their way. More of us need to act like Obi-Wan and honor the Prime Directive. Yeah, I’m risking nerd apocalypse by mixing Star Wars and Star Trek references to help you remember this important point the next time someone asks to pick your brain.
Advising For a Living
Starting in October 2011, I spent roughly a year in an early-stage VC firm. I had left the digital agency where I was a partner after we finished the sale of our company. I had always been close to the startup scene and hoped to launch my own eventually. But at that time, I needed a break from the grind of building and saw this part-time VC gig as a great way to help companies and gain insights.
The job was interesting, rewarding—and pretty damn fun!
I spent my days listening to pitches from startup founders and coaching those our firm had invested in. In every case, I would listen, ask probing questions, and provide feedback from my perspective of a career spent building a tech agency and launching new products at a big CPG firm.
Pitches came and went, but the companies we invested in kept returning. At a minimum, we had quarterly board meetings, but several founders would book time with us between meetings to get additional advice and share more detailed progress. My VC partners and I rarely asked for these meetings, but we would always find time when founders requested it.
As the months came and went, I started to notice a pattern: Some asked for more time than others. And since I saw these founders more often, I felt more personally involved in their businesses. My feedback became more direct, and they followed it more directly. It started to feel like I was part of their team.
Unfortunately, it led to another trend: The companies that asked for the most time struggled. And they all ended their runs a few years after we funded them.
I believe they stopped thinking for themselves and began taking my words as gospel. Some worried that they needed to do what I said to keep me happy so that I would fund their next round. Others bought into the idea that I was an expert. But my words were just…words. I had little skin in their game. I didn’t live in their businesses. And I never spoke with their employees or customers. I was just giving my opinions and moving from meeting to meeting. Looking back, I wish I was less of an enabler.
Meanwhile, the companies that we barely spoke with seemed to perform the best. We joined their board meetings each quarter and sat in awe as they showed off impressive progress—that we had zero impact on. When these founders asked for advice, it was specific, probing questions. They pushed back and compared my responses to what they heard elsewhere. I could see their minds weigh competing perspectives to pick the right decision—their decision.
These founders figured a lot of other stuff out on their own, too. They didn’t ask for a bunch of customer introductions or expect them to happen. They built a compelling product and sales engine to put it in front of the right audience. And instead of relying on the Board to drive their strategic decisions once a quarter, they built strong executive teams that made big decisions daily.
It’s Their Hero’s Journey
The funny thing is I had to re-learn this lesson when I launched my own startup. My co-founder and I took our investors’ and all the other experts’ words as gospel. We built a SaaS tool because that’s what investors wanted, and we stopped reporting our (lack of profit) because “no one looks at profit.”
Eventually, my co-founder left, and I slid into the CEO seat. My kick-ass exec team and I looked at each other and realized we’d have to figure things out for ourselves as our burn rate ballooned. We decided that nobody knows what they’re doing. We shifted from SaaS to service—which our customers were eager to pay for. And we got profitable—so that we could control our own destiny.
Our investors were caring and helpful, but they didn’t have the fingertip feel for our business—after all, they had to manage a portfolio of dozens of brands and got pitched hundreds of times each year.
Today, I see so much of the startup path in the classic Hero’s Journey, popularized by Joseph Campbell. It is considered an archetypical story model because it has been repeated so often in recorded human storytelling. My favorite example is in the original Star Wars trilogy, where Luke Skywalker heeds the call to adventure and ends up saving the galaxy.
A key role in the Hero’s Journey is that of a guide or wizard who presents the “call” to the protagonist and acts as an early guide and teacher. In Star Wars, this is Obi-Wan Kenobi. He tells Luke that his destiny is part of something bigger, introduces him to the lightsaber, and helps him get off-world and into the mix.
But there is a point in the stories where the teacher withdraws. After all, the Hero must make the journey alone. This happens when Obi-Wan allows Darth Vader to send him to the great beyond, allowing Luke to fulfill his destiny.
That’s what we mentors need to remember when founders come to us for advice. We can open some doors and provide encouragement, but we must take that lightsaber hit and disappear into the ether before we muck with their heroic journey.
Or, to put it in Star Trek terms, remember the Prime Directive—the rule that we must not interfere in the natural development of a planet. Or, in this case, a startup. If we have too much of a hand in things, we’ll screw it up. The right way to mentor is to be kind, bring encouragement, and present any advice with the disclaimer that “this worked for me but might be the absolutely wrong path for you.” And sometimes, when they ask for more advice, we need to decline politely.
Startups are hard. That’s a feature, not a bug. Founders need to get their asses kicked day in and day out through their own personal experiences and decisions. That’s the only way to learn. Advice is too easy to give and almost always wrong. Remember that even the most successful startup role models got to their successes through a combination of luck and decisions that were made at a different time and place than yours.
Now get back to your journey…we’ll be watching!
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BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
A growing chorus of thought leaders and investment analysts are looking at the potential impact of GLP-1. That’s not a misprint—it’s the name of the class of weight loss drugs that includes Ozempic, and it seems to be eclipsing ChatGPT on the hype meter.
This post by Josh Barrow offers interesting insights into how our human programming might get an upgrade thanks to this new class of drugs—even while some “consumption-heavy” companies see their stock prices fall.