How to find your next mentor, with Janice Omadeke

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1:26I 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. Janice Omadeki 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. Entrepreneurs were stubborn. We are a stubborn lot. And I think also part of me was very ego-driven of like, let's get that next round. Like, let's go. Like, why not? And everything inside me told me to explore an alternate route.

2:12You've got to have incredible talent at every position. It's like this huge push. There are fires burning when you're going home. Can you believe it? Such an idiot. and then you go back to, this is totally going to be amazing. There are so many easy ways. I have no idea what to do. Sorry, we made a mistake. But you have to time it right. Oops. Working as a three-bedroom apartment. Stuff that just seems absolutely nut balls. Ten years later, we're like, well, that's just how you do it. We haven't made it just how you do it.

2:42This is Masters of Scale.

2:47I'm Jeff Berman, your host. This week on the show, serial entrepreneur and author Janice Omadecki. 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' 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.

3:31Janice, welcome to Masters of Scale. Thank you. Thrilled to be here. I cannot wait to have a conversation with you. Thank you for having me. I have been so looking forward to this chat. Before we dive in to 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? 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, you know. 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.

4:12And 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 11-year-old Janice was locked in.

4:52That 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. Janice, do you remember any of the businesses that you thought about starting or the problems you wanted to solve at 11? I hated the way that it felt on a rainy day or a snowy day in DC when you would wear jeans and then get on the bus and the bottom of your jeans were just, just not a comfortable feeling.

5:38So 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. 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 like 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 like desperately trying to figure out how to occupy time and not be on screens all the time, we invented a game called Netflix or Startup, where I would give the kids four totally like random disconnected elements.

6:24So it would be like kangaroos, naval oranges, airplanes, and the country of Chile. And you have to pitch either a startup or a Netflix show with like one minute to prep. It's still like 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. My parents, having both immigrated from the Congo to the United States through college scholarships from missionaries. You know, 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.

7:13Those 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 headspace of this is a problem that I need to solve. And of course, I'll find a way to solve it. You referenced being a management consultant, being in defense contracting. Where did the switch flip for you to say, I have to go do this thing? I myself had several Steve Jobs quotes in my dorm room and, you know, in various apartments And so follow your heart and dreams and do what you love and everything.

7:57But I was also very intentional about wanting to pay off student loans and just be strategic with it. And 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.

8:41And 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 20s and default to something that doesn't even matter in the long-term landscape. Just because you happen to be a Black woman. 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.

9:34Yet 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. 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?

10:14One person. Who is that person and how did you find them or they find you? 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. Not an industry well-known for its high EQ and yeah. Not quite, 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.

11:06It 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. How did you go about finding the people, the mentors, to get to actually launching and then building the company? 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.

11:49And 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 know that feeling. It's all consuming. So every question that I had, every thought that I had, every time I left my townhome 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?

12:27And 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 kind of 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.

13:08So 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 in 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. They were 100 % 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.

13:48Like, 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-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.

14:25These 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? In 2018, I got accepted into the Mass Challenge Accelerator. I made a very specific Mass Challenge 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.

15:11I 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.

15:53onboarding. 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.

16:37So 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, you know, strategic partnerships. And just over time, coming in through the headspace 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. Still ahead, how a tragic loss changed Janice and her approach to business.

17:30Real leaders don't back down when the stakes are high. They innovate, they push forward, and then they take the stage at the Masters of Scale Summit. Join us in San Francisco, October 7th to 9th, to hear from the CEO of the New York Times, scientists using cutting-edge technology to find cures, the leader of crypto powerhouse Coinbase, a retired four-star general, and many, many more. Apply now at mastersofscale.com slash apply25. That's mastersofscale.com slash apply25.

18:31aws.amazon.com slash activate and start building. Expanding your business in the U.S. can feel like a maze. Every state has its own payroll, benefits, and compliance rules, which can pull your focus away from growth. That's why founders use Deal. Deal is the professional employer organization, or PEO, that gives you a dedicated HR expert plus Fortune 500 level benefits for your team. The National Association of PEOs says businesses can grow twice as fast if they use one. So if you're scaling, make it simple with Deal. Go to deel.com slash mos and get up to three months free. Welcome back to Masters of Scale.

19:18You can find this conversation and more on our YouTube channel. 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 curveball, the 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? 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.

20:11And 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. You know, 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 Mass Challenge. I called my mom, asked for her blessing. And she said, absolutely, this is what I immigrated for. Like, you have to go.

20:55And 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 Mass Challenge. My parents were very much like, okay, we want you to do this, but also what is this?

21:38What is this risk? We had no idea that you were this entrepreneurial, right? And so I wanted like a massive win for her. I wanted her to just see it while she still could. And, you know, 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 kind of that one-on-one time with mom, right? So it was my turn. It was like three in the morning. And I just remember having this like whispering conversation with her of like, I'm going to do this.

22:13I'm sorry I didn't do it in time, but I'm going to do it. just like keep watching basically it was like keep watching i'm so sorry thanks and she must be so proud of you oh absolutely there's no doubt um so the way that mass challenge 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 Mass Challenge. 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 and the situation, managing director and just some members of the team that knew.

23:06So 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 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.

23:49And 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 an 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 helped 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.

24:37So mother passes. Continue to grow. Janice, 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? 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 kind of what was going on, and thankfully they shared their wisdom. So immediately found therapists and, you know, 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.

25:25And 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.

26:10So 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. book 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, you know, 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.

26:59So I didn't know what she was picking up on. And so at that point, you know, reading it made me feel like I was catching on fire. So I just brought it home with me. I wasn't ready. And 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?

27:36Did 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 guisence and wisdom as if she knew seven years later that I would randomly reread this, you know, 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. Thank you for sharing that. It's beautiful. And I want to come back to the turning point you're at now.

28:16But in 2022, you decided to sell the mentor method. It's a critical and often really difficult moment for entrepreneurs, right? Do I keep going? Do I sell? There's an opportunity. Sometimes you have to sell. Why did you decide to sell the company? The same voice that told me to build it told me it was time to let it go. So it was 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.