7 Rules of Success from iMentor CEO Mike O’Brien


Mike O’Brien is a nice guy. His employees testify to this truth in a way that feels like testimony rather than obligation. And it’s easy to see why. O’Brien has a quick smile but is measured in his speech. He’s a listener. He’s caring. Perhaps that should come as no surprise. Under his stewardship as CEO, iMentor, a program that matches students from low-income communities with mentors who help them prepare for and succeed in college, has grown from a social-good start-up into a national non-profit juggernaut. Why? Because Mike O’Brien is a nice guy, but he’s also an intense guy. He is ambitious for himself, his employees, and the organization he leads.

O’Brien possesses what venture capitalists call a “growth mentality.” He thinks huge, but also tactically, articulating future goals in terms of donors, donations, headcount, program expansion, mentors, and mentees. He wants to reach more people, to change more lives. iMentor has helped some 30,000 kids prepare for higher learning over the course of 19 years. O’Brien hopes to duplicate that in the next five years by adding three new cities and expanding its partnerships with Big Brothers Big Sisters in 11 new cities.

Naturally, this requires a certain amount of relentlessness and a hell of a lot of discipline. As such, O’Brien has guiding principles he holds to closely. These rules for success have allowed him to not only pull himself up, but to do so for the young people iMentor serves.

1. Find a Mentor

“When I came to iMentor I was young and I’d never had an office job. There was an incredible leader here, Caroline Kim Oh, who saw that I was very passionate about our work and raw in every other way. She believed in me and gave me opportunities and we sat seven inches from each other over a four year period. I heard every phone call she made and was briefed on everything she was thinking through.

The level of candor was incredible and presented all of us with a huge learning opportunity. I came to really respect that transparency and I’ve tried to practice it with my employees.”

2. Understand Your Organization and Your Place in It

“While teaching in East New York, I got really interested in the role relationships played in the classroom and the way they showed up to class. I believe that was an undervalued insight in education so I started looking for an opportunity to work in that space. I found iMentor, which was small at the time — just a couple hundred students and mentors. I came in as a case manager and worked a series of jobs over the following few years. I wrote curriculum. I did fundraising. I worked on our first software platform. When I took over as CEO a decade ago, I’d had almost all the roles in the organization. I understood how everything worked.”

3. Relationships Take Time

“When I was teaching, I had five English classes. There were 150 students in those classes. I also had the opportunity to coach the boy’s basketball team. There were 12 young men on that team. And I taught an afterschool creative writing workshop for four young women. Every single day, I’d go from 150 students to 12 to 4. I started to understand that the relationships I was developing with students played a role in how people showed up — their aspirations and performance in school. People don’t talk about the importance of relationships. I think that’s true in educational settings and workplace settings.

Now, iMentor has offices across the country. So, how do I build relationships and trust with people in those offices? That’s a new challenge for me because we used to be a small organization. The strategy that seems to work the best is spending consciously unstructured time with the entire team. We’ll have a meal together. You simply have to make time to get to know people and lead with curiosity about their day-to-day experience and believe their perspective on work is important.”

4. Build a Shared Vision, Then Share It

“My first charge when I took over as CEO was to figure out how we were going to scale and the most strategic way to do that. I spent my first nine months in the role putting together a five-year vision of what we could accomplish that was predicated on us raising a lot more money than we ever had. Ultimately, that became a galvanizing vision that set us on the path that we remain on today.

More recently, my team and I spent about 15 months creating the 2018 to 2023 vision for iMentor. We walked away not only with a vision, but with a financial model and programmatic strategies. That worked. And, perhaps most importantly, there’s now a whole community rallied around a vision. We’ll chase it together.”

5. Be Good, but Not for Goodness’s Sake

“What I do is not purely altruistic. I really value that the work I do is urgent, important, and challenging. I wanted to do something hard and I wanted to do something important. You can’t get much harder or more urgent work than working in education.

There have been years where we’ve had hundreds of mentors on the waiting list. There’s pent-up demand for this kind of opportunity. Seeing the impact on an individual’s life, watching people change their perspectives, playing a role in putting all the pieces together, and scaling that in a significant way created this work experience that’s incredibly rewarding. I kind of live at the bleeding edge of my professional abilities. It’s always a challenge. I’m incredibly grateful for this opportunity.”

6. Work-Life Balance is Not a Problem to be Solved

“I have an incredible wife who enables and supports me to both be everything I can be to this place and then also to try to do that on the home front. The other thing I would say is this: You have to get really organized and commit to trying to be as good as you can be in both places. Beyond that, it’s chaos.

I have two boys and they are so ridiculous and bring me so much joy that just their presence brings balance to my life and I deeply, deeply appreciate that. There is no defense for their creativity. They break you out of your day. Watching how quickly they grow up gives you a sense of the urgency of this work. We’ve got one shot as young people come up to get it right.”

7. Recognize the Gap Between Potential and Achievement

“Our students are incredibly ambitious and hopeful. What they often don’t have is equitable access to experiences that can transform their potential. What we can do is validate that student’s aspirations and help them connect to opportunities that will push them forward. The closer you get to schools and students, the more optimistic you get. You realize how much is up for grabs at any given moment in a young person’s trajectory.”

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