How to find your next mentor

Note: Transcripts are automatically generated from episode audio, and are not fully corrected for spelling, grammar, and formatting.

JANICE OMADEKE:  So if you can just give me some advice on why it will work, why it won’t work. I promise you, coming from defense contracting, I have a very thick skin. So if you think that this doesn’t have legs or my baby is ugly, tell me why, so I can fix it.

JEFF BERMAN: Janice Omadeke has always been hungry for feedback. It’s one of the reasons she wrote a book and built a platform to help people find mentors. Like so many of us, Janice personally appreciates the power and potential of a truly great mentor.

OMADEKE:  Entrepreneurs were stubborn. We are a stubborn lot, and I think also a part of me was very ego driven of, like, let’s get that next round. Let’s go, why not? And everything inside me told me to explore an alternate route.

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BERMAN:  I’m Jeff Berman, your host. This week on the show, serial entrepreneur and author Janice Omadeke. Janice is no stranger to breaking barriers. She ranks among the first hundred Black women to raise over a million dollars in seed funding, and was Austin, Texas’s first Black woman to secure a venture-backed tech exit. Her book is Mentorship Unlocked, the Science and Art of Setting Yourself Up for Success. Mentorship has played an incredibly important role in my life too, so I was eager to get into this with Janice. Janice, welcome to Masters of Scale.

OMADEKE:  Thank you. Thrilled to be here. I cannot wait to have a conversation with you. Thank you for having me.

Copy LinkJanice Omadeke’s entrepreneurial bug

BERMAN:  I have been so looking forward to this chat. Before we dive into mentorship and the company you built, I’d love to just start with, where did you first get the entrepreneurial bug? Where did it come from for you?

OMADEKE:  Being a proud daughter of immigrants, my parents always taught us to think about how we could amplify our lives, and live as big as possible. And while my parents did face hardships, they always instilled the importance of education and problem-solving, and how you can continue to work to improve yourself. And so around the dinner table, my dad would ask myself and my two siblings to play this game of, what was a problem that either you or your peers encountered at school, or you saw on the bus home, wherever, that you would want to build a business around? What problem would it solve? Who would you sell it to? I mean, he would ask questions around — not realizing what it was, but just — what would be the go-to-market strategy? How big do you think the TAM actually is, and things?

And out of myself and my two siblings, they definitely were kind of rolling their eyes at it and weren’t as enthused, but eleven-year-old Janice was locked in. That was my favorite time of the day, because I’ve always thought in an entrepreneurial space, I’ve always come from a space of empathy and wanting to help others. And the way that my brain would light up in solving those problems, and getting that sort of dopamine response of, “Okay, I might be 11, but my contributions to the world could be much bigger than that, if I really refine these concepts.” That was extremely powerful.

BERMAN: Janice, do you remember any of the businesses that you thought about starting, or the problems you wanted to solve at 11?

OMADEKE: I hated the way that it felt on a rainy day or a snowy day in D.C when you would wear jeans and then get on the bus and the bottom of your jeans were just not a comfortable feeling. So I wanted to create some sort of device that, you could clip your jeans and roll them up, without taking up too much space in your backpack. And then once you’re back at school, then you just unclip them and you’re good to go, without that feeling of wet denim around you.

BERMAN: Since I grew up in the DMV as well, and we had a lot of snow days back then, I have a sense memory of that musty smell of the wet jeans as everyone’s clamoring onto the bus and all of that. So I love you bringing that back. I have three kids, and in COVID, as we were desperately trying to figure out how to occupy time and not be on screens all the time, we invented a game called Netflix or Start-up, where I would give the kids four totally random disconnected elements. So it would be like kangaroos, naval oranges, airplanes, and the country of Chile. And you have to pitch either a start-up or a Netflix show, with one minute to prep. It’s still so much fun to play this game, but I love the idea of games as a way to inspire entrepreneurial thinking. I love that story from your dad, what a wonderful set of seeds he planted with you through that.

OMADEKE: My parents having both immigrated from the Congo to the United States, through college scholarships from missionaries, learning to make it on your own, learning the importance of community, learning how to believe in yourself, that even when things are hard, you will find a solution, and one that builds a better life for yourself. Those are all transferable skills into entrepreneurship, and so seeing that across my parents and the communities in which they were a part of, to me, when I had the idea for the Mentor Method, or even in my earlier career days in management consulting and defense contracting, I always approached it with that head space of, this is a problem that I need to solve, and of course I’ll find a way to solve it.

Copy LinkIdentifying gaps in mentorship & sparking the Mentor Method idea

BERMAN: You reference being a management consultant, being in defense contracting. Where did the switch flip for you to say, “I have to go do this thing?”

OMADEKE: I myself had several Steve Job quotes in my dorm room and in various apartments, of: follow your heart and dreams and do what you love and everything. But I was also very intentional about wanting to pay off student loans and just be strategic with it.

So when I had the idea for the Mentor Method, I was in year two of my strategic management graduate certification from Harvard, in my disrupting technologies course. And the final project was to, similar to my upbringing, pick a problem, disrupt the industry, how would you do it? And build out the complete business plan. Coming from defense contracting, which was predominantly the all boys club, and coming from management consulting, which was very similar, I was always eager to expand my learning in any way possible. And so within that space, I did find that it was extremely difficult to find mentorship. Oftentimes people would want to match me to the only underrepresented professional that had made it to the top. And that felt odd to me, that a large corporation would take a high performing, over eager, very moldable talent that I was in my early twenties, and default to something that doesn’t even matter in the long term-

BERMAN: Just because you happen to be a Black woman.

OMADEKE:  Exactly, exactly. And this was around the time where Bumble, Tinder was just blowing up, and I couldn’t understand how I could theoretically meet someone for a larger relationship, just by using my phone, yet I had to beg people and hunt them down in their offices to try to find mentorship. That felt way too hard and too difficult for me. And so looking at the market, seeing that there was space to make building meaningful connections accessible, as it was in say, the online dating space and the dating app space, to me it felt like a no brainer. Thankfully, I’d already studied entrepreneurship from MIT, and so started following a lot of their process, but that’s really how it started.

BERMAN: Notwithstanding the ineffective, perhaps unhelpful, even, attempts at pairing you with mentors, had you found great mentorship along the way before you started the Mentor Method?

OMADEKE: One person.

BERMAN: Who is that person and how did you find them, or they find you?

OMADEKE: Her name was Amy, and she was the creative director of the team I was on. So it was myself and then my manager and Amy. And I met her during the interview process at PWC, and she was so unapologetically herself. She practiced a high level of self-awareness and approachability, which I hadn’t seen, yet, coming from defense contracting at that point.

BERMAN: Not an industry well-known for its high EQ and … yeah.

OMADEKE: Not quite, good reason to get out, but there was just something almost Noxzema-refreshing feeling about being around her, and the space to ask questions and not have to worry if they were dumb questions. It was just such an important season of my life. But that was the first and probably the only, until I started venturing into entrepreneurship networking groups when I was still working nights and weekends on the Mentor Method, and it was essentially a PDF and a dream. That’s where I really started meeting my mentors.

Copy LinkInside Janice’s strategic networking framework

BERMAN: How did you go about finding the people, the mentors, to get to actually launching and then building the company?

OMADEKE: To this day, I still have several Google docs with running lists by category. So individuals I hope to have the opportunity to learn from one day, companies that I hope to contribute to their growth using my strengths and backgrounds, as I know that I will one day. And then there’s also one of, these are the problems I’m seeking to solve right now, broken out into different categories.

Now at the time of the Mentor Method and building that, that was all I was thinking about, you that feeling, it’s all consuming. So every question that I had, every thought that I had, every time I left my town home in Old Town, Alexandria at that point, was spent on learning how to move the Mentor Method to the next step. So my first set of questions weren’t even to other entrepreneurs, but just, what is the market? What are the incumbents doing? What are my core differentiators, and why do I feel that I could take this forward? And how come other incumbents and other businesses haven’t done it this way? And if they have, why did they fail? Why did they grow? Just getting a sense of where the landmines were, so I could mentally prepare for what I was going to get into.

From there, when I saw it had legs and I was like, okay, let’s continue taking this on, then I started going into networking events, and my questions were around, “Where else should I be spending my time?” While I am technically classically trained in entrepreneurship from MIT, we all know there’s a difference between a case study and actually getting into the arena. So what don’t I know? At this point I was still teetering the line of trying to decide between a B2C concept of going straight to consumer, or going enterprise, and I just wasn’t sure which one. I actually felt more passionate about the B2C, but quickly realized, and talking to people in a similar space, that B2B was the right way to go. And I said, “Thank you for that feedback,” tested it myself, and  they were a hundred percent right.

So there were a lot of questions around what industry I should focus on, because mentorship is just so broad. I didn’t want to boil the ocean, I was really urgently seeking my beachhead market. Where would I go first? So I was exploring Ed Tech in the university system, from a B2B perspective, management consulting of course, and various other places. So my questions were to leaders and CEOs that were dominating in those industries, with their respective businesses, what their go-to go-to-market strategies were, how they were communicating with their buyers, how long it took them to acquire their first set of customers, how they did it, if there were prospective customers that maybe we could collaborate, which is such a sweet thought now, looking back with that level of gumption. But that was my first set of questions.

Copy LinkFinding and persuading mentors and advisors

BERMAN: These are busy people, so can we just spend a minute on how you persuaded them. You don’t have a product yet, you have an idea, you’re super compelling, you’re energized, you’re fired up, but to persuade people to come be an advisor to a company that doesn’t really have a product yet, and help you shape it, how did you get them to do that?

OMADEKE: In 2018, I got accepted into the MassChallenge Accelerator. I made a very specific MassChallenge list, looking at previous sponsors, looking at partners, and looking at those who were in the mentor registry of where they were working. Cross-referenced that with HR leaders within those organizations, made a spreadsheet in my Google Doc, so that I could go to specific mentors. I also cross-referenced with things like Best Places to Work, and wanted to make sure from a values perspective that I was only speaking to companies where they, either in the press or in some way, shape or form, have indicated an interest in an enjoyable work experience.
So by having that list, anytime I was meeting with a mentor or there was some energy around like, “Oh, how can we help?” And otherwise, I knew exactly who I wanted to meet from that first conversation. I sequenced a lot of my mentor conversations, based on the companies that I saw were hiring pretty aggressively at that point, and thinking, “Okay, well there’s a use case there around new hire onboarding.”

So five of the 10 people I want to meet, I’ll pitch that concept and see what they think. I also think too, I never came in thinking that I was going to save an entire company’s problems. I always approach these leaders as, “Can I have 15 minutes of your time? I am too early for you to purchase this. Just so you know, I’m not selling you yet. I know we’re too early, but I know that I can come back and pitch you in a year, two years with your guidance, and that this really has legs. So if you can just give me some advice on why it will work, why it won’t work. I promise you, coming from defense contracting, I have a very thick skin. So if you think that this doesn’t have legs or my baby is ugly, tell me why so I can fix it. So that in the next several meetings, we’re building out that pipeline towards yeses, towards sponsorship, towards strategic partnerships, and just over time coming in through the head space of, I want to learn from you, I want to listen, I want to hear what your experiences are, why is your job so hard? Those sort of real questions without any other ask, but just tell me about your day.”

BERMAN: Still ahead, how a tragic loss changed Janice and her approach to business.

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Welcome back to Masters of Scale. You can find this conversation and more on our YouTube channel.

Copy LinkCoping with loss & channeling grief into leadership

So Janice, you’ve got your first paying customer. You get into the accelerator program, you move to Austin, you’re building and you’re scaling, and then you’ve got a curve ball, a pretty big one that comes in your personal life. Can you tell us what happened there, and how that changed your trajectory and your path?

OMADEKE: Yeah, so at the end of 2017, my mom grew gravely ill, and then top of 2018, January 3rd, she was diagnosed with pancreatic cancer, stage four. So we’d anticipated about four months based on what the surgeon said, but we were very fortunate and grateful to have had eight months before her passing. And I always try to find some type of movie analogy when I talk about this, but there isn’t one. Someone who has loved and lost a core piece of themselves through a parent, knows that there isn’t an equivalent to it. I used to call it my sort of Christian Bale Dark Knight origin story, and in a way, yeah, it is, but it was really a strong motivator in reflecting on the power of what I was building, and what it could do for an individual. So I get into MassChallenge, I called my mom, asked for her blessing, and she said, “Absolutely, this is what I immigrated for. You have to go.”

And so I was going back and forth between DC and Austin during that four month period of the program, making sure I could go to chemo appointments, and I was still getting that quality time, at the same time, pitching the business, continuing to grow. I don’t have an explanation for the way it felt to see my star rising and my business starting to grow, as my mother and the nexus and the reason I even was empowered to do this, her health declining. It was something very motivating for me, because I wanted … at the time, I didn’t have a win outside of getting into MassChallenge. My parents were very much like, “Okay, we want you to do this, but also what is this? What is the risk? We had no idea that you were this entrepreneurial,” right? And so I wanted a massive win for her, I wanted her to just see it while she still could.

And she passed away in August of 2018, and that was a pivotal moment for me. Our last conversation the night before, my siblings and I all took shifts, because at this point we were doing at home hospice, and we all wanted that one-on-one time with mom. So it was my turn, it was like three in the morning, and I just remember having this whispering conversation with her of like, “I’m going to do this. I’m sorry I didn’t do it in time, but I’m going to do it. Just keep watching.” Basically, it was like, “Keep watching.”

BERMAN: I’m so sorry.

OMADEKE: Thanks.

BERMAN: She must be so proud of you.

OMADEKE: Oh, absolutely, there’s no doubt. So the way the MassChallenge works, there were about 80 entrepreneurs whose businesses were chosen. And so the Mentor Method, and I was part of the top eight. So four days after my mom’s passing, I was flying back to Austin because it was the finals, and we got our first win, the first big win, a $25,000 non-dilutive investment from MassChallenge. And that win means the most to me more than anything, because the only people who knew that I was suffering going through this emotional turmoil in this situation, managing director, and just some members of the team that knew. So to have received that win, and to see the joy on their faces, and to just feel energetically the source of that win, you can’t replicate it.

And so since then, I’ve really reflected on my mother’s journey and I’ve reflected on her experience, and it was baked into both the DNA of how I built the team for the Mentor Method, but also how I built out the product, and how I’ve just operated as an entrepreneur. I saw her so afraid during her chemo process, because her boss and the culture of her employer, she was in finance, even in her chemo appointments, she would still be on her laptop answering questions, because she didn’t want to lose her benefits in healthcare. And that was a heartbreaking thing for me to see, but then I also took that consideration into how employees experience work. That is a terrible and disgusting culture, for somebody to be losing their life and still feel like they need to answer any email or be in a spreadsheet. Absolutely not.

Within my sphere of control, I promised myself that I couldn’t save my own mother from that experience, but if I can help somebody else’s child not feel that, because they got connected to a mentor, which gave them a new career opportunity outside of where they’re currently working, or help them see that there might be another team or opportunity where they can continue expanding, then I’ve at least done something to make the world a better place.
So mother passes, continue to grow.

Copy LinkThe lasting impact of support and guidance

BERMAN: Can I just ask, when you say continue to grow, were you, if you’re comfortable talking about this, working with a therapist, with a coach, how were you processing your grief and also your ambition at the same time? Who was helping you through that?

OMADEKE: I stayed very curious about my own well being, so the first thing I did was find a therapist; I also had a leadership coach. I let very few mentors know what was going on, and thankfully they shared their wisdom. So I immediately found therapists, and the power of journaling, and just keeping track of how my body was responding to things. And knowing when I was feeling flooded, like, “Okay, maybe I need to just work from my apartment, and maybe today is just sending out the cold pitch deck emails for today, and then tomorrow let’s go out and do networking when I’m not necessarily in as much of a grief hole.” But I really optimized the way that I worked with stakeholders and teams and advisors and business partners around that, and people that I worked with were understanding, because I was always consistently professional and I never made my grief somebody else’s problem. I knew that was mine, and I knew that the people I had the opportunity to work with had their own things going on. So I never wanted to monopolize a situation, but I also didn’t want to be one of those people that just self-sabotaged and just completely ignored the most detrimental thing in my life.

So mom passes, pandemic happens, I hadn’t been home because it wasn’t safe to fly. I come back home September, 2021, visit my dad, and he tells me that my mom wrote me a letter that I didn’t know about, her last month or so with us, and at the top, it’s labeled “For Janice” and the Mentor Method. And it’s just one page, front and back, from a notebook, and it’s just the most detailed information of like, “Well, when you’re stressed, X, Y, and Z, think about these things.” 

And I didn’t know that she was seeing it, because I’m on my laptop and I’m hustling and doing all of these things, but I never allowed myself to be seen as an entrepreneur in those moments, because I just wanted to be her daughter. So I didn’t know what she was picking up on, and so at that point, reading it made me feel like I was catching on fire, so I just brought it home with me, I wasn’t ready.

Then about two months ago, I was just doing general spring cleaning and organizing, and there was just a voice, similar to the voice I felt when I needed to start the Mentor Method, that was just like, “Go read that letter again. Why not? Let’s just see, you’ve grown a lot. Just read it.” And so I did. And the synchronicity of it was just unparalleled, where I think sometimes in those moments, people can ask themselves, “Did I do the right thing? Did I prioritize my time accordingly? Am I making that individual proud?” And just based on that letter alone, I know that she saw it. There was so much guidance and wisdom, as if she knew seven years later that I would randomly reread this at 37, in a very pivotal kind of turning point in my life that I’m in right now. And that’s been just such a gift, and almost a continuation of that origin story, and why I’m so passionate about advancing others and continuing to evolve in my career.

Copy LinkRecognizing the right time to exit

BERMAN: Thank you for sharing that, it’s beautiful. And I want to come back to the turning point you’re at now, but in 2022, you decided to sell the Mentor Method. It’s a critical and often really difficult moment for entrepreneurs. Do I keep going? Do I sell? There’s an opportunity, sometimes you have to sell. Why did you decide to sell the company?

OMADEKE: The same voice that told me to build it, told me it was time to let it go. So it’s 2022, we had just graduated from Techstars, continued through the fundraising process, and then July, 2022, I was at happy hour with a friend, fellow entrepreneur, and there’s nothing better than being able to talk about pipeline and deals and what you’re going through with a fellow early stage entrepreneur in the trenches. So what’s typically an enjoyable conversation for me in 2022 turned into my very first panic attack, when I started discussing the future of the Mentor Method. I’d never felt that before.

So Velma, my friend, quickly got to my car, after 20 minutes of the AC and calming myself down, I just said, “Okay, I surrender. I’m hearing the wisdom, I get it.” Entrepreneurs, we’re stubborn, we are a stubborn lot. So I had ignored that voice for quite some time, and I think also a part of me was very ego-driven of like, let’s get that next round. Let’s go. Why not? And everything inside me told me to explore an alternate route. And so after that, I talked to my mentor and business partner, Joseph Kopser, who has been instrumental in every step of the way of this business, since we connected in 2021. And he was like, “Trust your gut. Follow the process.” He had gone through his own acquisition process several years ago. I spoke to several CEOs in the Austin community about some of the indicators I was seeing and what my gut was saying, and everyone was very supportive of that decision, because they had also gone through it themselves in earlier chapters of their lives, before I knew them. So I felt very empowered that it was the right thing to do. So started exploring relationships with our strategics and other opportunities, and the acquisition was just the perfect opportunity in September of 2022.

BERMAN: You mentioned that you are at a pivotal moment in your career now. Can you tell us what’s going on?

OMADEKE: When I started the Mentor Method, we were at the beginning of this current, what we’ll call a president’s first term, and I’d been reflecting on who I was then. And while I’m a completely different person, as time does, that fire in seeing the bigotry and the hate, the misinformation, the intentional emotional abuse that is being distributed globally now, I can’t sit with it and I can’t live with it. And so I am now actively interested in collaborating with builders and visionaries who are really going to co-create the world that I want to live in. I’m very motivated by that. How can I use this experiential scar tissue as an entrepreneur, to amplify those that need a voice? And that takes multiple forms. That looks like being an angel investor for Black women led businesses, and providing that mentorship and information of, “Okay, I started a business under this person’s first administration, so here’s how I did it. Here’s some ways that you may be able to get grants and other opportunities, but don’t lose focus. Don’t let that distract you. That’s an important piece of it.”

But then also in philanthropic endeavors where I choose to work in the future, just really evaluating how I can use those strengths to amplify the businesses that are optimizing other people’s way of living, and not just in the traditional kind of going to mentorship to another talent management company. There’s a lot of diversity of thought and perspective that is kind of untapped power.

So for me now, having mastered that particular space, I’m eager to learn again. I want to get into a new industry, I want to continue expanding, because that neuroplasticity, it’s hard to shake.

BERMAN: Does that mean you have another start-up in you? Is there another start-up coming?

OMADEKE: I am thoroughly enjoying being the one holding the microphone and kind of holding the spotlight to other founders and leaders right now. But that entrepreneurship bug, I’m sure we will talk again.

Copy LinkThe one thing people should know about mentorship

BERMAN: Last piece of advice for someone seeking a mentor, what’s the non-obvious thing that people should know, as they’re trying to find someone to help them on their journey?

OMADEKE: You know 75% of what you need to do already, your gut is telling you. Do not build an emotional dependency on your mentors, your mentors are not a place for your codependency, they are not a replacement for a parent, let’s say. Your mentor is there to support, advise, and guide you to become the best version of yourself. So don’t lose sight of that when you’re building those mentor relationships. Make sure that when you’re approaching a mentor relationship, you have other avenues of building connection, and get very clear on the objective of what you want to work on with that individual, and be okay with the relationship lasting three meetings, three years, 30 years, who knows? But be open to allowing that relationship to run its natural course, however long that may be, instead of always trying to force the individual to fit and meet you where you are, that’s just not human condition. And the more that you can stay open to receiving mentorship, open to receiving wisdom from all sources, right? Not just a mentor, but just anywhere that you find that educational moment, take it, take it and run with it, and study it and do what you can. Integrate that into your life, and you will be unstoppable, easily.

BERMAN: Great advice. Janice, thank you for being on Masters of Scale.

OMADEKE: Thank you for having me.

BERMAN: Janice Omadeke’s advice about mentorship is spot on. She’s living proof that proactive, intentional focus in this area can create monumental ripple effects in your career. We can’t wait to see what she does next.

I’m Jeff Berman. Thank you for listening.