3 Things I Learned From Interviewing 27 Mentors

This summer I completed a project for which I interviewed 27 of the JuntoMentors. The purpose was to understand why they decided to become - or continue being - a Mentor in our Chicago program, and in what ways have they benefitted from the experience. It can be challenging to find startup advisors who are not only experienced but skilled as mentors; we're fortunate to have so many involved with Junto.

Being the newest member of the JuntoTeam, I was excited to get the chance to have short one-on-one conversations with the Mentors who have made this program what it is. They provided some terrific insight into their mentoring experiences and I learned a great deal by listening to them.

There were many things I learned from the interviews, besides a strong appreciation for what Raman and Catherine have done with Junto, some of which we will share on our blog in the coming months. For now, here are my three main takeaways.


Andrea Moran said “If you don't show up and learn something everyday, what are you doing?”

This is something that really stuck with me because I’m a firm believer in learning something new everyday. In a community that is full of experienced entrepreneurs, it’s easy to learn something new everyday. Just by taking the time to sit down and talk to each of the Mentors, I have learned so much about business and life as an entrepreneur.

A common response I heard from the Mentors was that they benefit from being a part of the JuntoTribe because they get to learn in addition to the companies. In fact, Stuart Baum said, “I forgot I wasn’t the one being mentored.”

We structure the mentoring program in a way that Mentors share experiences and ask questions. While it may be easier to give advice, this approach is to let others learn from one’s prior experiences or stories. And when one Mentor shares an experience, it often triggers a response in another who then has an additional experience to share. In my interviews, many of the Mentors said that, with this approach, they pick up tips on how to handle current problems they are facing within their own companies.


For most CEOs, there are overarching issues that are bigger than the industry in which they operate and their depth of experience. CEOs can often feel lonely at the top. Our Mentors are seasoned entrepreneurs and CEOs who have plenty of experience being in the shoes of the Apprentices. These examples provide a sense of relief and support to those who feel like they may be alone in building their business or facing certain situations.

A big topic that often comes up is about employees and how to manage them. This can range from hiring to training to firing. Each Mentor has an experience around how they or their companies have managed their employees. I have realized that it is extremely beneficial to hear experiences and stories from Mentors who are in a completely different field because they bring in a different perspective that may not have otherwise been brought up. Kevin Turner summarizes this by saying, “It provides the leadership team with access to a lot of business people [and] insights to help companies address their challenges and opportunities.”

Each Mentor has his/her own network of people they can tap into separately to pull in even more experience. If a Mentor is not necessarily an expert at one topic, they likely know the right people to reach out to. Because of this, the Apprentices have access to many networks of people who can provide more specific help with an issue.


Alan Yefsky states, “Good ideas can come from anyone.”

While the Apprentices are the ones who are being mentored, a lot of their insights help the Mentors as well. These are entrepreneurs who are starting their companies in the current marketplace, so they have experiences that some Mentors may not be familiar with. Young entrepreneurs can bring a fresh perspective to the table which can be undervalued at times.

Advancing one’s business and learning does not only occur from the most seasoned professionals. Anyone can have a great thought or idea that can change the course of a business. It’s important not to shut anyone’s ideas out because that limits the amount of growth someone may have. Instead of it being a strict “teacher-student” relationship, our Mentors treat the Apprentices more as peers and colleagues to enable mutual learning.


When I started on this project, I had no idea how much I would learn from having short, 15-minute conversations. I was also excited with how many Mentors were eager to share their thoughts with me. The JuntoTribe is full of wonderful people who are always willing and eager to help.

The insight I have gained into the Mentor’s minds is something I am extremely grateful for. Having these one-on-one talks with them helped me see just how incredible each and every one of them is as a startup advisor. No two Mentors are the same nor do any of them have the same experiences to share, making Junto even that much more diverse. There is a strong willingness to learn from each other as well as pass on wisdom to Apprentices and fellow Mentors.

As a part of my role, I get to sit in the meetings and take notes. Because of this, I am actively listening and soaking up the knowledge and experience the Mentors have to offer. I am learning first hand what has worked and what hasn’t worked in forming a successful company.

When I asked the Mentors why they continue coming back to Junto to be a Mentor, a lot of them have said that they do it because they want to give back and they wish they had a program like this when they were building their businesses. These are Mentors who have a deep appreciation for helping fellow entrepreneurs and who continue to grow and learn themselves.