Stephen Ajayi is the cofounder and CEO of YearOne, a startup designed to help graduates of code school programs find the guidance and mentorship they need to land incredible jobs and succeed in their careers in tech companies. We sat down with Stephen to get his perspective on mentorship and how startup founders can more effectively manage a mentor-mentee relationship.
How mentorship shaped an entrepreneur
Microsoft for Startups: Through your work with YearOne, you’re an active proponent for the value of mentorship. We’d love to hear more about how mentorship has played a role in your growth as a founder.
Stephen: When I think about my own entrepreneurial journey, there are clearly several people — whether I specifically referred to them as mentors or not — who I can readily identify as critical components driving my growth and the success of YearOne. They were individuals who really helped me get to the next level.
And I think that’s an important aspect of mentorship to specifically call out. These people weren’t just interested in startups or my company. My best mentors have also been deeply invested in helping me in my personal journey as a founder and leader. In fact, some of my earliest mentors continue to mentor me, today. I feel like they’re supporting me, even though the business I’m building has gone through a variety of changes.
Looking back, I think a lot of my growth came from focusing on the right people at the right time. Choosing to engage with mentors who had the experience and insights that could truly help me move from where I was at that time to the next milestone that really mattered. And taking the time to identify those opportunities.
In my experience, mentorship is all about helping you figure out where you should be going and then supporting you in the process to get there. Especially when your mentors are other founders. Mentorship is best when it’s a combination of aspirational thinking and tactical advice from people who have been in a similar position.
Finding a mentor
MfS: How did you go about finding mentors?
Stephen: At the beginning of my journey, I sought out mentors through connections in the startup community. Sometimes, it was simply talking to other founders at a coworking space. And that conversation would sometimes result in an ongoing dialogue with other founders working out of the space. Or sometimes those conversations would lead to “You know who you need to talk to…?” moments where folks would make introductions or connections that were helpful.
As my company started to take shape and we were beginning to actively pursue product-market fit, I moved on to startup accelerators, like Techstars, which tend to be highly focused on providing mentorship for early-stage companies. I had the opportunity to participate in multiple programs. And they each brought a unique aspect of mentorship to my journey.
If you’re a founder struggling to find mentors, I’m a firm believer that accelerators can help you. I know they played a significant role in providing access to the mentors who helped me take YearOne to the next stage I was seeking, raising venture capital.
And now that we have raised capital, I find our investors to be great mentors as well as an effective conduit for getting introductions to other founders or mentors that could be helpful. Our lead investor Zeal Capital Partners, for example, is super helpful in navigating our growth and how we think about our seed round.
I can’t really name all of the mentors who had an effect on me and my company, because it takes a village, right? I can say that putting myself in situations where I had the potential to access other mentors and founders has been a key to my personal success.
Establishing a strong relationship with a mentor
MfS: You’ve touched on the concept of mentorship as a long-term relationship. And you’ve clearly had success in establishing those relationships. What advice would you give to other founders in terms of establishing and maintaining an ongoing relationship with a mentor?
Stephen: I think the most important thing to understand about the mentor-mentee relationship is that it’s built on the assumption of a natural “give and take” dynamic. This can feel uncomfortable and transactional to founders. Especially in the early going, when you don’t feel like you’re contributing much to the mentor relationship. That exchange can sometimes feel unequal.
So when you’ve asked for something—you asked for an intro as an example or for connection somewhere—it feels uncomfortable to ask them for something again. But the thing that I have learned is that those networks will eventually become more equal in the value they provide over time, even if it feels “all take and no give” at the outset. Just because you can’t necessarily do anything to be helpful in the current moment does not mean that will be the case in the future.
But you should also have empathy for the mentor. It doesn’t feel great on the mentor side to feel like you’re constantly being asked to go above and beyond in terms of effort. Mentor relationships tend to feel better for both parties if you’re meeting each other halfway. for things.
You should feel comfortable asking for what you need. And often if you’re asking too much, people let you know.
Meeting your mentor halfway
MfS: Can you give some examples of how to meet the mentor halfway or help take on part of the work that needs to be done?
Stephen: Over time, I have become better at doing that. And what I’ve learned is that the act of taking on some of the effort and meeting them halfway is what makes mentors feel like you value their time.
Instead of going to someone and saying, “Hey, I need help with something.” I think that you can do some work and then have a conversation more like, “I’ve compiled a list of people I would like to talk to and you appear to have connections to several of them. Is it possible for you to help me connect with any of these people?”
That’s a very different conversation than “I want to connect with [company].” And expecting the mentor to do that for me without doing any legwork or helping that person be helpful to you. Now you’ve created a chore for your mentor. You’ve created work for them to do. Unknowingly you’ve turned something that could be accomplished in a few seconds and clicks into an hour of your mentor’s time, which is expensive for the person.
I’ve learned that if you can send someone something that they could just pass along, then it feels like you’re not asking for very much. It’s like “Hey, I would love to have you send this along to one person. It will take like two seconds.” Versus “I need you to think about the context of all this stuff and how you would then state this to a specific person.”
Make it easy for mentors to be helpful. That’s the key. Create simple asks, prepare them with the content they need, and they’ll be far more likely to be helpful. And far more likely to continue the relationship with you.
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