The First Rule of Startup Mentorship: The Entrepreneur Is Never Wrong

All first-time entrepreneurs have one thing in common: They have never built a startup before. As they progress from launching to growing a company, it’s common for them to want to benefit from the experience of others, and for people with experience to want to help young entrepreneurs. In fact, I believe that everyone, at any level, should be surrounded by the right circle of mentors to help them think through various aspects of their lives, both personal and professional.

I have been fortunate to call a number of people mentors throughout my journey. In recalling the five and a half years since joining WeWork, I can point directly at amazing advice I received from my mentors that resulted in practical changes in my behavior or decisions that I may have otherwise made differently. At times the advice focused on high-level, strategic thinking. At others, it was as simple as taking a day off so I could return to the battlefield refreshed.

The advice ended up shaping my journey and, as a result, the journey of WeWork. But it didn’t come from random conversations. Instead, it came from a deliberative process of me meeting, on an ongoing basis, with people who I look up to and are interested in engaging in the art of mentoring. Some of my mentors are current or past managers, and others are people I’ve encountered along the way and reached out to for feedback.

In the past few years I’ve been fortunate to call the legendary Lew Frankfort (pictured below) my personal mentor. Lew is the former Chairman and CEO of Coach, with vast experience in management, product, and the balance between physical experiences and the digital world. The story of how and why he decided to “professionally adopt” me is a good one but we’ll keep it for another post…

With that said, it should be no surprise that at WeWork Labs, a platform for early-stage startups and entrepreneurs around the world to pursue their dreams, we are passionate about how we think about mentorship at scale: how to open up opportunities for entrepreneurs to connect with mentors and for mentors to connect with entrepreneurs. The process of “democratizing mentorship” is a beautiful endeavor we have embarked on.

The most important thing to remember when you’re mentoring a startup

As WeWork Labs scales across stage, experience, industry, and other axes, it’s important to remember that not all advice is the same. The ability to be a good startup mentor is a skill that has emerged only in the past few years. (Mentorship has existed since the dawn of humankind, but startups, as we have come to define them, are a more recent human development.) And yet, having spoken to many mentors and entrepreneurs receiving mentorship, and having observed many mentoring sessions, I’ve noticed a pattern that is destructive to the purpose of mentoring itself.

Imagine a situation:

Entrepreneur: “There’s this thing I want to do, X. Dear mentor, what do you think about it?”

Mentor [thinking to themselves: Oh boy, I’ve seen this idea fail a hundred times before. Please God, I hope they don’t do that]: “I think this is a bad idea. You shouldn’t do it and here’s why.”

First and foremost, the mentor must come with an attitude that the entrepreneur is never wrong. That is not to say that entrepreneurs cannot be wrong, but the job of the mentor is not to have black-and-white opinions, right-or-wrong perspectives. It is to help the entrepreneur fulfill themselves and come from a place of openness, humility, and empathy. The entrepreneur “always being right” as an approach to mentoring can mean multiple things, but at its core, it is based on two philosophical pillars:

  1. No one really knows: There is no absolute truth, and if there were an absolute truth, it is the job of the entrepreneur to feel and know what it is, not the mentor. Every revolutionary in the field of entrepreneurialism has been thought to be wrong by many more smart people than those who thought they were right. So for the sake of humility, imagine yourself sitting in front of a young Steve Jobs being pitched the Apple II. Who knows? Definitely not me.
  2. Failure is a learning experience: Some of the most important learnings in life come from failing at something that you thought you were going to succeed in. One of the most destructive things a mentor can do is steal the entrepreneur’s opportunity to fail and absorb every drop of learning from such an experience. This can create a dilemma: If you are certain they are going to fail and they end up failing, then what is your role? But this only calls for a more nuanced and creative approach to being a mentor. It does not eliminate its basis for existence.

Your role as a mentor

So if your role as a mentor is not to tell the entrepreneur whether they’re right or wrong, then what is it? It is to help drive them towards their destiny, whatever that may be. Here are a few things that I recommend a mentor think through.

  1. Push the entrepreneur to develop a mission or set of objectives that can help them imagine what success looks like. The ability to articulate a future that encompasses what the startup is aiming to achieve, and the impact it will be able to make if it is successful, is one of the most common missing pieces a mentor can help fill.
  2. Help drive towards action. Action can take many forms. It doesn't necessarily mean doing before thinking—the thinking itself is a form of action. So is research. Bias for action means asking yourself the hard question of whether you are being efficient with your time and that of the people around you.
  3. Try to understand which people or companies the entrepreneur may benefit from connecting with and create some of those connections.

But what do you do if you really think they are totally, utterly, completely, brutally wrong? My best advice here is twofold.

First, this may be an unhealthy mentoring relationship, and you should consider severing it. Not every mentoring relationship is destined to be successful. Even if you bring your most evolved self into the conversation and are asking questions meant to help them realize that a different path may be better, if the discord is absolute, then you need to acknowledge that this may not be a very good fit. Realize that it is just as likely that the issue is with you as it is with them.

Second, be a mentor to yourself and ask yourself the following questions: In what ways is this a bad idea? In what measurable sense does the “badness” of it manifest in a way that contradicts the objectives the entrepreneur has? Try to understand the thought process the entrepreneur took to get here. You might realize that it’s actually the right thing, given more context, or at least you will have exposed them to the fact that they have not been thoughtful enough in the decision-making process. Frame questions about the startup’s objectives so that they can understand that their approach may be misguided. But herein lies the challenge for you: If you are not able to clearly articulate that, then maybe it’s time to find a mentor for yourself.

Even if you speak to the entrepreneur and discover a fundamental error in their plan, beyond stepping aside and saying to yourself, “That may be my personal opinion, but no one really knows,” remember that there is a way to guide this conversation to an empowering place that results in the entrepreneur’s growth. If they do not feel empowered and encouraged by you, then you have not done your job as a mentor. There’s room for “tough love,” but it should be directed against objectives you define together.

When the rule doesn’t apply

All that being said, and in the spirit of there being no absolute truths, there is a situation where I would advise an entrepreneur not to pursue an idea.

Entrepreneurship is a force that should be used for the greater good: creating jobs, fighting inequality and famine, reducing health risks, improving quality of life for people in need, and so on. It shouldn’t be used to take money from unsuspecting consumers without providing any real value. It shouldn't be a tool to feed off of people’s weaknesses, abuse them, or otherwise profit off of them in sneaky ways. And, of course, it shouldn't be used for violence, terror, or the tools that support such activities.

What should you do if you’re mentoring someone who you feel is working on an evil project? Should you encourage them with questions, or try to gently steer their objectives towards a more positive path? Or would you do everything in your power to help them see the damage they could cause? Most entrepreneurs are neither saints nor villains, but it’s an interesting spectrum to consider.

Of all the entrepreneurs I’ve met, those working on harmful ventures have been a tiny minority, and most of them never fully realized their vision. But there’s a basic moral litmus test I use to spot these situations. As a mentor, ask yourself whether this startup is contributing in any way to the greater good or will end up making people’s lives worse. If it’s the latter, there are two simple questions I ask the entrepreneur: First, what kind of impact do they want to have on the world as an individual? Second, do they feel their venture will make the world a better place? Very often, people will work on an idea that doesn’t contribute to the greater good without ever asking themselves these questions. As the mentor, you simply need to put a mirror in front of them to help them see things in this light.

Early-stage startup entrepreneurs are a unique group of human beings. Some of them are going to end up changing the world in profound ways, but we don’t know which ones  just yet. One of the greatest gifts a person can receive is for an up-and-coming entrepreneur to trust them to lead them towards their destiny. If you happen to be the recipient of such a gift, treat it with care. This gift is not about you, your beliefs, or your opinions. It is about them, and how you become a 1,000 percent positive force who helps them craft their journey. Do not steal experiences from them. Do not let your past experience and background cloud what may be a fundamentally different future. Above all, there is no such thing as right or wrong.

Live long and prosper,


Author image

Roee Adler

Global Head of WeWork Labs
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