How to Find Your Purpose in Your Entrepreneurship Journey with Yewande Faloyin

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How to Find Your Purpose in Your Entrepreneurship Journey with Yewande Faloyin


Sean: Hey, guys. Welcome back to the show. It’s me again, Sean Si, aka Mr. CEO of 22, your host. And for today we have Miss Yewande Faloyin. She’s from the United Kingdom and she’s the CEO and founder of Otito and she specializes in coaching entrepreneurial executives and serial high achievers to accelerate into a more senior, more impactful leadership position. 

So if you are one of those people who are trying to scale up your organization, maybe you’re a mid-level manager right now or maybe you don’t have a team yet, you want to lead yourself better. I hope this episode adds more value to you. You want a thank you so much for being here on the show.

Yewande: Thank you so much for having me, Sean. I’m looking forward to our conversation. 

Sean: Hey, I’m curious what led you to found Otito? I’m interested in your entrepreneurial journey and I’m sure a lot of people are interested in what you do as well and how you got there. Can you tell us something about that?

Yewande: Yeah, of course. Um, I know journeys are always interesting, so my background is very corporate, you know, I graduated from university in London, actually did tech, I was a techie. So I was a software developer. I joined a bank, Morgan Stanley in London. Um, and it was exciting because it’s like, oh my gosh, I’m making money for the first time. Like actually having a paycheck. 

Enjoyed that for three years. And then I got bored and was like, All right, tech is interesting, but I didn’t care much about languages and stuff. And then I got poached still within Morgan Stanley but into prime brokerage. For those who don’t know much about prime brokerage, basically taking care of hedge fund clients, super smart investors, and traders start a company, but then they don’t understand business, right? So our team’s job was to help them connect with whether it was the sell side or legal stuff or product didn’t matter, but understand what our clients needed and provide for them.

And then I went, okay, that’s interesting, but I don’t care about helping rich people get richer. What do I do now? Then I learned about consulting. I ended up doing a pro bono consulting gig while I was at Morgan Stanley and thought, Oh my gosh, this is amazing. I love the idea of it as almost it feels like at every stage it kind of scaled up. But getting to the point where I was like, I love problem-solving, I love business. How can I do more about that?

I didn’t know what I wanted to do with my career, but it was a great opportunity just to understand the business more and understand the kind of challenges that businesses have. So I ended up joining McKinsey as a consultant, which I describe as the best three years of my corporate life that I would never do again because I burnt out twice in 18 months.

And that was like, okay, as much as I love this thing, as much as I love business and I love problem-solving, I love the team and I love working with really senior clients, this is just not sustainable.

So I quit my job at McKinsey, and for anyone who knows me, that is very unlike me.

Like I always have a plan. Like if I’m going to quit something, I have something to start. But I was exhausted, so I quit that.

I booked a yoga teacher training course because I love yoga. And my approach then was figuring out what my ikigai was, what’s my purpose, and What’s thing that resonates with me? And through conversations, random conversations, really just exploring, not being, not being confined by who I thought I was, but just exploring anything that seemed interesting.

I discovered this thing called executive coaching and it just clicked. It was like, Oh my gosh, this is the thing that I’ve always done. And what’s interesting is that because you talk about my entrepreneurial journey, I think because I took a slightly different approach at that time, it wasn’t that I wasn’t head-focused.

It was more about intuition and how I was feeling instead of maybe what I would have done before, which is join a company to be a coach for some reason.

And I still don’t know why because I don’t remember making the decision. It just felt natural. I just had a calling to start my own thing, to create an environment where not only was I doing this thing that I loved, but then creating a business that resonated with who I am. And that was the start of founding Otito.

Sean: That’s awesome!

I’m getting a lot of stuff that I already want to unpack from that. Let’s rewind a little bit and go back to Morgan Stanley. You mentioned that you were in the tech world, you did programming, which is very interesting that you started that way because I’m a tech guy. What were some life lessons or leadership lessons that you use now that you got out of working with Morgan Stanley?

Yewande: Lots of stuff. So I like that question. I think it’s always interesting because sometimes we assume and I loved your intro where you said something like, Oh, if you don’t have a team and you’re leading yourself because people often forget, right? It’s like, Oh, I’m not a leader because I don’t lead a team.

It’s like, No, you’re a leader because you lead every day, whether it’s whether you have a team or not. You’re leading other people, right? In some way. And often the first person you start with is yourself. So sometimes also say if you can’t lead yourself, then you can’t lead other people.

Like it’s the same thing. It’s just different, different audiences. Um, one of the things I learned a lot at Morgan Stanley. I was very fortunate with my team and the people who supported me. But two things immediately come to mind. One kind of stems from what I just said there around leadership is not about having a team because while I was at Morgan Stanley, I never actually technically had a team.

Towards the latter part of my career, there was a point where I had one person reporting to me, but the way that our department worked was that there were a lot of different departments that had to work together, especially in my role, because I wasn’t the expert in anything. I wasn’t an expert in legal, and I wasn’t an expert in sales, but my hedge fund clients and the CEOs who I worked with expected that I would understand what they needed. I would come back to the firm and then work with and influence people too.

To get what? To create something and then deliver it to them. So I often had to work with people who were a lot more senior than me. 

So one of the biggest leadership lessons for me was really. Learning and understanding how to influence people irrespective of seniority and do it in a way that’s not where either. I don’t feel doubt in myself or I don’t feel like I’m being combative, but bringing people along. 

And a lot of the lessons that I think about my leadership and my style now really stem from that. It’s about the partnership with others and leading them towards the goal and the destination that we both agree on.

Sean: And is there any book or podcast or YouTube or mentor where you learn that because it’s a very hard thing to learn, not everyone knows how to get along with someone else. Whether you are a leader with a position or you are a grassroots-level personnel who’s trying to get your colleagues to rally around a certain project that you need to get done, it’s not easy.

We have weaknesses as people and a lot of us are blind. That’s why we call it a weakness. We’re usually blindsided by these weaknesses. How did you learn that? Can you take us step by step? Or maybe it’s not a step-by-step, like with your yoga time, right? It was a series of serendipitous events. Can you share something about how you learned this with us?

Yewande: Sure, I’ll share how I think I learned it back then because it’s all in hindsight, and then I’ll share a little bit more about what I do now and often what I do with my clients, which is a little bit more strategic.

So I think again, I was very fortunate because I had a great group of managers, mentors, and sponsors around me. And so I think with some of it I think it is maybe my intuitive style. Um, but I know a lot of it was watching and seeing the way that other people responded and almost going, all right, that feels like I responded to that so someone else might respond to it. I think I’m saying this like it was very strategic.

I don’t think it was. I think it was kind of osmosis. And also my style is generally listening. I think that’s something that I have a natural strength in, which probably made it easier for me. So I would be the person who comes into a room and I’m just like, You need to do this because it’s on a list and my client needs it.

Like I often listen a lot to these other partners that I had to work with. I mean, partly because I didn’t have a choice. I didn’t have any. I didn’t hierarchically; they were often more senior than me, and I had no right to be like, do this. So I think that helped me. Um, but a combination of the environment I think was really important because now that I look back, had I not had as supportive a team and people who I could watch and go, Huh, that’s the way that they’re responding to clients.

That’s the way they’re responding to people. That’s the way that they’re engaging. I don’t know that I would have learned as quickly what I often do now, which is very different, from your point, the clearer we are about who we are and what our preferences are, what our strengths are or weaknesses in my language don’t usually use weaknesses.

I sort of see them as development points. The clearer we are about that, the easier it is to get there. So I have a model that I always think about because a lot of the work that I do is mindset based, both in terms of my mindset and other people’s. So if, for example, I go into a room and so let’s say, I think I need to lead you to agree with something that I want, right? If my mindset, when I go into it, is, Oh my gosh, Sean’s never going to agree. Like he just always has the opposite view. He never agrees with me.

Like, what’s the likelihood that I’m going to say something like that? I’m going to listen to you or that I’m going to say something that’s going to pull you forward? Probably not, right?

Because I already have that barrier. But if I shift to and they’re like seven different mindsets, but if I shift to and I’ll give you another example, one where I go, actually, Sean’s very discerning.

We don’t agree, but that’s because he takes a different view.

And my role is not to try to convince him or for one of us to win, but it’s to partner with him and better understand what his view is and help him understand how we can meet in a way where I get what I want and he gets what he wants.

And we are excited to find that solution together. Now, the way that I ask questions, the way I come about, it’s very different, right? And it doesn’t matter whether you’re more senior or more junior than me.

The point is I’m clear about what I’m trying to achieve and how I want to show up in that conversation as opposed to the default, which may just be, Oh my gosh, I’m freaked out because it’s not gone well before.

Sean: Yeah, that’s. I’m taking notes and I’m getting it. When you were starting with your support team, you mentioned you intentionally took notes and not a lot of people do this. By the way, how do your superiors or your higher-ups, or how your peers would communicate and influence others to their cause? That’s very, very important right there because people would usually go about their day-to-day not taking notes on how to improve, but just trying to do their jobs and keep their heads low. So that’s very, very important what you said.

Yewande: I completely agree with that because I think a lot of us don’t. What I would add to that is take notes and then actually practice and see it as an improvement, because I also see some people who take notes and then they sort of go, okay, that’s a thing I should do, but I’m too worried about it. But actually, go. All right. I’ve noted this now, so let me try it. Okay. It worked. Let me do a little bit more. Okay. It didn’t work. Let me stop doing it. So I just wanted to add that little piece.

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