The pitfalls of mentorship and “Smart Money” in startups

A few weeks ago I wrapped up a structured incubator cohort where I mentored the founder of a food delivery app. Let’s refer to him as “Tim.” 

Over a period of six months Tim eagerly took my advice as he and the team launched his startup. However, within a few weeks of us working together, he was deferring to me on even trivial decisions. 

I was always around to help, and he texted and emailed about the smallest things. I felt honored, but I did regularly find myself trying to empower him to rely on his own judgment. 

The app was launched, but struggled to get any traction. Instead of trusting his gut and pivoting, Tim wanted me to tell him what to do. 

This story illustrates a common pitfall in startup mentorships – an over-reliance that stunts independent thinking. While mentorship is often glorified, the truth is more nuanced.

Lets dive into the under-discussed downsides of mentorship, and how it can ultimately do more harm than good.

Effective mentorship should be a reciprocal relationship where the mentor offers guidance, not mandates. The role is to “ask questions, not give advice.” This allows founders to retain ownership of strategic decisions.

Founders who are too dependent on mentors skip critical analytical steps and simply accept whatever their mentor suggests. This prevents them from sharpening their judgment. 

A key job of any founder is to develop their own intuition, their own “spidey sense”. 

It is too often that entrepreneurs over-value the advice of brand name mentors while under-valuing market signals and diverse perspectives. Why? These mentors are also investors or people of high social standing in the startup ecosystem. They can make founders feel inadequate for not listening to their advice.

Over-reliance also fosters an unhealthy emotional and professional dependency. The founder may struggle with key decisions without their mentor’s input and defer major strategic calls to them. 

This not only disempowers entrepreneurs, but can impede necessary pivots. If the market changes or was never there to begin with, mentors become a crutch to compensate for the founders’ insecurity and lack of confidence. 

First-time founders especially have the “Impostor Syndrome” and high profile mentors can often exacerbate this issue.

I have seen this problem intensify if the mentor has an authoritarian style. Some mentors enjoy mentoring because of the hero-worship and retain power by encouraging dependence. Many of these authoritarian individuals are also the early investors in the startup that they mentor.

In the startup industry the concept of an investor who is also a mentor is referred to as “Smart Money,” and I assure you that more often than not this money isn’t really that smart.

Hare some real-world examples of “Smart Money” mentorship at work: 

• Juicero relied heavily on advice from their high-profile investors and advisors like Google Ventures and Kleiner Perkins. This led them to focus too narrowly on creating a highly-engineered, absurdly expensive, and later widely mocked juicer appliance rather than the experience/service around it. They eventually collapsed after raising $120 million.
• Theranos founder Elizabeth Holmes leaned too much on guidance from former government officials like Henry Kissinger and George Shultz as she sought to gain credibility and contacts. This prestigious advisor board failed to provide objective advice and oversight, allowing major problems to go unchecked. Elizabeth Homes is now in prison for defrauding investors.
• Social app Stamped took direction from high-profile mentors like Google Ventures, Twitter co-founders, and others as they pivoted from a reviews site to a social Q&A app. But this led Stamped to lose focus on their core value proposition. The company eventually shut down and sold in an acqui-hire deal.
• Clinkle raised $30 million from prestigious investors like Andreessen Horowitz as the startup’s 22 year old founder heavily leaned on advisors like Richard Branson. However, this high-profile support meant little oversight or practical guidance, and Clinkle burned through this capital without ever launching a product.
• Color Labs raised a whopping $41 million pre-launch while leaning heavily on mentors from Sequoia Capital and Bain Capital. But the pivots and lack of focus guided by these mentors led the photo-sharing app to fail dramatically.

This is not to say that all “Smart Money” mentors create an unhealthy relationship with the founders. But, even though almost all VC’s insist that they are “smart money,” 7.5 out of 10 venture-backed startups fail. It sure does seem that a good amount of these relationships may not be working. 

While quality mentorship can undoubtedly accelerate growth, over-reliance has significant downsides.

Seek diverse advisors, push back on advice when your gut disagrees, and become self-aware of any emotional or other dependency. With thoughtfulness, startups can reap the benefits of mentors while retaining independent strategic thinking.

I would encourage founders to insist that mentors do not give advice, but rather just ask good questions. Advice often goes against the founders own insights and market feedback, and you should be comfortable in constructively challenging the mentors guidance.

Consider advisors as input to your decision process, not the decision makers themselves. Don’t outsource your strategic thinking. And reflect on whether you struggle without your mentor’s blessing. This emotional dependency suggests an imbalance. 

Healthy mentorships empower founders with advice and confidence to think independently. But nothing hampers a startup like over-reliance on an advisor at the expense of the founder’s strategic thinking and ownership. Keep this downside top of mind, but don’t become so cautious that you miss out on the benefits. 

Always remember that there is only one expert in what your company does, and it’s you.