November 3

How to Find your First Mentor

Every piece of career advice you’ll ever get talks about the value of a mentor. Successful founders and business owners will often allude to their mentors in conversations.

Naturally, everybody who doesn’t have a mentor wants one.

So they approach potential mentors with emails about what they need. What they don’t realize is that the mentor-mentee relationship is something that occurs organically, when both of them have something of value to offer each other. All of the following are patterns I’ve observed over 700 plus interviews and conversations with friends about how people found their mentors.

1. Choose a Great Boss

According to Liz Wiseman, author of Multipliers, one of the most important decisions you’ll ever make in your career is the first boss you choose. This matters more than the company, the job, or the salary. I made the mistake of not choosing a great boss many times in my career.

A great boss can radically change the trajectory of your career for the better. Just ask Biz Stone. In his book Things a Little Birdie Told Me, Biz wrote the following about his first boss:

Steve became my mentor. He drove me in to work every morning, and we became friends, playing tennis together on on weekends. he was more than 30 years older than me, but were a good match. I didn’t have a dad growing up; he had two daughters and had always wanted a son… I’d ask him a million questions, not just about design but about life. How did you know when to propose to your wife? How much money did you ask for at your first job?

Choosing a great boss is one way to organically find a mentor, because you’re inevitably going to have a relationship with them. But you have to be proactive about getting the most out of that relationship.

2. Create Mutual Exchange of Value

When I found one of my first mentors in 2013, he actually approached me for help on self publishing a book about a project that was coming to an end. I’d managed to build a small platform and even self publish a book that had sold close to 1000 copies. Every week, we’d get on the phone, and I’d share my insights on what he should write about, how he could market his book, and more.

Because he’d been a guest on the podcast multiple times, I knew he carried a wealth of knowledge about how to grow a business. So during our conversations, after I shared my advice on book publishing with him, I’d ask for his advice on my business. After several months, he became my first mentor. In the 6 months that followed, my self published book became a Wall-Street journal best-seller, we rebranded the podcast, and sold out a conference in 2 weeks. He was the one who actually came up with the name Unmistakable Creative.

Here is another example of this: Ryan Holiday met Robert Greene around the time he dropped out of college. Since the publication of Robert’s previous book, the internet had evolved quite a bit. Ryan had a unique understanding of this landscape, and Robert needed to understand it. So Robert became one of his first mentors. But when I asked Ryan about it in an interview, he told me that they would go months without speaking. He was there to learn, but not in a position to demand anything of Robert.

Look at any mentor and mentee relationship and you will see this pattern play out over and over again. If you come to the table with something of value to offer, you’re going to have a lot more leverage to build a relationship with a potential mentor.

3. Go above and beyond the call of duty

Charlie Hoehn has worked for well known entrepreneurs like Tim Ferriss, Ramit Sethi, and Tucker Max. And he exemplifies what it means to go above and beyond the call of duty.

One of the first people he approached about what he could offer was Ramit. He knew that Ramit could do a great deal more with his video content, and Charlie could help. But he didn’t just say he could help. He created a detailed plan of how he could help and what he could do along with samples of his work. He went above and beyond the call of duty before he was even working for someone. He made his work impossible to resist. Eventually, he parlayed his experience with Ramit into becoming Tim Ferriss‘ first assistant.

The ability to follow instructions and do what you’re told doesn’t really cause you to stand out in any way at all because it’s a necessity, not an option. But when you come to the table with ideas and insights that go far beyond your job description, your value increases exponentially.

4. Types of Mentors

Informal: Informal mentors come in all shapes and sizes. You can find informal mentors through books, podcasts, blogs and more. All of us have access to an abundance of informal mentors. Often the transition from informal to formal happens when a mentee takes something they’ve learned from an informal mentor and puts into action.

This is exactly what Selena Soo did with Ramit. After getting to know him briefly, she offered to help him with some major changes he was making to his site. She shared the following with me during her interview on The Unmistakable Creative.

I met Ramit while I was in business school. He said he was relaunching his website, had two different versions, and wanted to get some feedback. He asked if I had a minute or two. But I literally carved out five hours to help. I went to the library, and I organized this focus group of people. We got feedback from people about the cost, copy, design, and the messaging. I put together a report and sent it off to him. He said, “wow this is amazing.”You want to be remembered. You can’t just be doing what everyone else is doing. You can’t be average. You have to do things that stand out. And that really made the difference.


Formal: Formal mentors would be people you talk to once a week, such as managers and investors in your company. Chip Conley was brought into Airbnb not only to be the head of hospitality, but also to be a mentor to Brian Chesky. The formal mentor relationship is something you can’t force. It’s up to you to pay attention for the opportunity.

Paid Mentors: A few months ago I was playing NBA 2k18 with the San Antonio Spurs. During the game, the commentators mentioned Kawai Leonard’s shooting couch. One of the best shooters in the NBA works with a shooting coach.

  • Paid mentors can have a big impact on accelerating your progress simply because they have more data points and experience to draw from. They’ve seen similar challenges and can ofter solutions. But what’s even more powerful about having a paid mentor is that you have skin in the game. When you have skin in the game, you take things more seriously.
  • I consider my writing coach Robin, one of my mentors. In the process of writing 2 books, she never sugarcoated her feedback, instead, she helped me to find clarity, and made my books much better than they would have been if I hadn’t worked with her.

For paid mentors, you want to make sure they’ve helped someone else solve the problem you currently have or have solved it for themselves. You also want to make sure your values are aligned.

Alignment of Values

One of the things that Tim Ferriss said to me in our interview on the Unmistakable Creative is that you want to “model people who not only have the success in a given field, but also have holistically the life you want because you can find people with hundreds of millions of dollars who yell at their kids or have to do tons of drugs on the weekends.”

After my first mentor and I parted ways to due to his health, and my business partner Brian and I decided it didn’t make sense to keep working together, I was on the lookout for a new mentor. I was fortunate to find him amongst the listeners of The Unmistakable Creative.

Joseph Logan and I became good friends over the last couple of years after many days of skiing and snowboarding together in Colorado. He’s been an executive coach for a number of startups in Boulder, so I asked him if he’d mentor me. He works with amazing clients, skis as much as he wants and makes good money doing it. Our values were aligned and he had holistically the life that I wanted.

Over the course of your career, you will have multiple mentors. Each one is the right person at the right time. But every one of those relationships will ultimately be built on a mutual exchange of value. Before you reach out to a potential mentor consider the following:

  1. Is the the initial ask super simple for the mentor to say yes to? The people you want as mentors have busy lives. The last thing they want is for you to create more work for them.
  2. Is it obvious that what you’re offering would make their lives easier? If you’re not bringing anything of value to the table, you have no leverage. ****
  3. Is your outreach concise and respectful of their time? Don’t write ridiculously long emails to busy people if you expect a response. Value their time the same way you value yours.


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