From Corporate Founder to Leadership Coach: Matthew Lindsey’s Journey

In this episode of Career Coaching Secrets, Pedro sits down with Matthew Lindsey, a leadership coach helping founders and teams tackle misalignment, burnout, and unspoken tension. Matthew shares his journey from corporate founder to solo entrepreneur, the pivotal lessons that shaped his coaching business, and how he helps clients align heart and strategy to scale successfully. Discover the power of accountability, building a tribe, and taking small steps toward massive growth.

Whether you're a career coach, entrepreneur, or leader seeking clarity, you'll gain actionable insights on mindset, sustainable growth, and unlocking true leadership potential.


Connect with

LinkedIn: https://www.linkedin.com/in/matt-lindsey-b37933b8/
Website: https://mattslindsey.com/

Transcript

Matthew Lindsey 0:00

One of the things that I'm very clear up front is especially in those discovery calls, all the way to the maybe the second or third session. So giving ourselves, you know, three to five hours of work together, I'm very clear from the get-go. They might come to me for marketing strategy, sales strategy, big, you know, operations or trying to scale their business. A couple of my current clients right now are trying to go from like 1.2, 1.3 million to three plus million this year in their businesses. Sure, you got to have the smarts, as Patrick Lincioni might say, you have to have the smarts of the business. You got to couple that. You've got to have that synergy or the cogs of both those wheels have to connect with the heart and the smarts.

Davis Nguyen 0:38

Welcome to Career Coaching Secrets, the podcast where we talk with successful career coaches on how they built their success and the hard lessons they learned along the way. My name is Davis Wynne, and I'm the founder of Purple Circle, where we help career coaches scale their business to $100,000 years, $100,000 months, and even $100,000 weeks. Before Purple Circle, I've grown several seven and eight-figure career coaching businesses myself and have been a consultant at two career coaching businesses that are doing over $100 million each. Whether you're an established coach or building your practice for the first time, you'll discover the secrets to elevating your coaching business.

Pedro 1:10

Welcome to Career Coaching Secrets Podcast. I'm Pedro, and today's guest is Matthew Lindsay, a leadership coach who helps founders and teams address the real reasons companies stall misalignment, burnout, and unspoken tension. After more than 12 years inside a mission-driven startup that scaled into a public company, he understands firsthand the pressure, loneliness, and complexity that come with leadership at scale. Today he works with leaders who are ready to tell the truth, realign around what matters, and lead with clarity and trust. His work supports teams in moving past performance for appearances' sake and into leadership that's grounded, human, and sustainable. Welcome to the show, Matthew. Thank you, thank you. Appreciate that. It's great to be here. Yeah, it's great to have you. And I like to go back to the origin story a bit. You know, I'm I'm kind of a nerd, so uh into comics and all that, the first edition, you know. So every coach has that moment where they look at their life and say, Yeah, I guess this is what I'm doing now. You know? So when was that for you, man?

Matthew Lindsey 2:24

Wow, very clear marker for me was in uh 2023, November. I read a book called Trillion Dollar Coach about Steve Jobs Personal Coach. And I had been doing a bunch of leadership development work in the corporate world, organizational health, passionate, very passionate about organizational health. And my the CEO I was working for at the time suggested the book because he knew I was really into all of this stuff. And I've had my own coach now going on eight plus years. So I've had my own business coach a few of them. I've got two coaches right now that I've uh one that I'm paying and one that's mentoring me. But in 2023, reading that book about how Steve Jobs and all these Silicon Valley executives, right? We're talking about the executives at the highest upper echelon of impact, uh global impact, in terms of how they shape and move those companies, all pointed back to this one guy, Bill Campbell, who said without his leadership, coaching, calling out the elephant in the room, really bringing teams together, really helping people find that clarity. Without him, there wouldn't be the companies that we know today. They wouldn't be as successful as they are and as they as we know them today. And reading that, I saw so many pieces of myself. Now I didn't see myself as Bill Campbell, I'm not there yet. I aspire to be like that in terms of impact, but there were so many pieces of the way he lived and operated, and the way that the authors, the three different authors, uh wrote the book and articulated who he was and his impact, just spoke volumes to me. I remember sitting at my kitchen table with my father, they were over for dinner, and I was showing him this book, and I had tabs and marks all over the book and underline, and I was just going through a few things with my dad, and my dad just looked at me and said, Why aren't you doing this full time? And that was the first aha moment. It was like the shining light from heaven coming down and just like glowing on me, saying, Here we go. This is something I've been preparing you for, Matt. So it was November 2023 where that light bulb just clicked, and I was like, Yes, I have to move in this direction.

Pedro 4:27

I like how your father coached you. Not sure if you agree with me. But it's about making the right questions, right? It's not just about, hey, you should be doing this full time. It's not like that. It's like, hey man, what's up with you? Why don't you just go and do that? You know, it's just awakening that that was already in you, but I love that. And just so I can understand, when did it shift from I'm helping people, this is my calling, to I'm building a real business around this.

Matthew Lindsey 4:56

Yeah, man. So leaving the corporate world was the big, the big kick out of the nest. I won't talk too deeply about that. It's a beautiful part of my story personally, but being kicked out of the corporate nest, being kicked out of the company, a company that I helped found. Like I was the last founder working in this organization. And um, the company was going down, down in revenue, and 40 people got cut in July of 2024. And I was one of those first 40 that got let go. My whole team did. But I kind of knew it was coming. I had that premonition, I had some insight from one of the one of my team members. I kind of knew, but I was already unsettled on the inside, knowing that there was something bigger calling me, and I need to leave this nest. I just didn't know how to do it. And the universe sort of helped me out of that nest. And so when I was sort of falling out of the nest in a in a beautiful good way, nothing scary. I was able to handle the transition really well. Thankfully, I'm really grateful for a mindset that moved me quickly into okay, what's next? I know what I feel called to do now. Let's just move into it and take the first steps. So, securing my education certification program, but one of the biggest things that really made the biggest difference for me, Pedro, was having a mastermind group. So my coach, Mike Green, had brought me into a small circle of other coaches and leadership development people before I had even left my corporate career. And I was already a part of this group. And so when this experience happened and I was kicked out of the nest, I had this group of really powerful individuals around me already. And like you pointed to just a few seconds ago, they started asking me really great questions, incisive questions, as Nancy Klein would say of how will you go forward? What would you like instead, Matt? Like, how are you going to make this happen? What steps do you need to take? And having a feedback loop of really good questions coming in set me on the path to make make sure that not only was this a dream, but no, this is a practical, tangible goal. And if I put steps forward, I can make this happen.

Pedro 6:57

That's so powerful, man. I love it. You know, it's like turning that hardship. I mean, it was your baby, also, right? And you got kicked out of the nest, and turning that hardship into an opportunity. And it really is about mindset and how you saw that and how posit positive you were about it and you are about it, you know, and how intentional it sounds like. So, but I gotta ask that after you got rolling, you know, who are the people that kept showing up, and you know, the ones you realize, okay, this is my tribe. Because and and the reason I asked this is because we see a lot of coaches that are trying to embrace the entire world, right? And it comes and goes. Sometimes it lands, sometimes it doesn't. I'm not sure if you went through that route, but who are the people that you felt like you clicked with the best, you know?

Matthew Lindsey 7:42

Hmm. That's that's an interesting question. When I'm surrounded by people that are motivated on their own path, when they're they're driving forward in life despite whatever obstacles they're facing, despite the chaos around them and their context, but they have a mindset of growth, opportunity. I'm going to make action. So one of my mantras currently is just one small step, Matt, one small step every day. And for me, I have this analogy in my head. I I love to backpack, I love to be in the mountains, I love to go out and do adventures. And so you put your backpack on. And when I go live live outdoors for a week or so by myself or with a few friends, I have everything I need on my back. So to me, that's a signal. I have all the resources. I have it all inside. I have everything I need. Do I need to sharpen skills? Do I need to grow in certain aspects? Sure. Do I need to gather some more tools along the way? Absolutely. But do I have everything I need right now to take a step today? Absolutely. There's no denying it. It's undeniable, I think, for most of us, if we stop and ask the question, do we have what it takes today to make one small step? And so that's been my mantra is Matt, put your backpack on. I'm climbing a big mountain, both to backfill my financial, you know, the the salary I had once had in the corporate career. I'm still working towards filling that and then hopefully exceeding that over the next few years. But that's a big financial goal. And then it's solo entrepreneuring, building a business and all the components that come along with that. There's a lot of different pieces to the current life I'm living and the goals I've set before myself that cause me to at one point look up the mountain go, wow, this is a big mountain, but I know I have what it takes. I know if I take step after step after step, I will get there. And so for me, surrounding myself with people that have that same mentality, no matter if we're doing, walking a similar path or not, it's just the inspiration and motivation. I need to have positive mindsets around me, people that are people of action doing it. And then having those people have a level of accountability that I can have accountability to them, meaning I need to be open and vulnerable and transparent enough and receptive enough to receive those tough questions, right? To get those tough questions back from my accountability mastermind group or from my wife or from good friends, people that can just hold up a mirror in the most loving, graceful, generous way and help help me see myself for what I'm what I'm actually doing that causes me to like continue to move forward, take that step, even when I'm feeling down or feeling frustrated or feeling overwhelmed, when I have a community around me, even if it's just a few people, that for me is the biggest difference.

Pedro 10:20

That's interesting, man. I like that. So I gotta ask you one thing. You mentioned climbing up the mountain, right? And what a big goal that is, and what a task that is, how hard it is. So let's say you're looking over your shoulder, right? And you're looking past it. So there's a potential client there. So how do people usually find you, you know, the marketing aspect to it, like while doing that, while doing that climb, you know, how do they actually connect with you?

Matthew Lindsey 10:48

Yeah, the the biggest way, and I I don't know how it is for other coaches. I think statistically it might speak towards what I'm about to say, but my network, right? Like the people that know me. And I think the majority of clients from here forward are gonna come because somebody else has been with me, has been served by me, with me, has worked alongside with me on a project. That's one thing I'm very proud of. Not that I was perfect in the corporate world. I did make many mistakes, but I always owned up to those mistakes in the corporate world, whether I spoke out of turn, whether I overstepped or overreached, or maybe I just didn't perform the way I thought I could have. I would go make amends. I would go talk to people. I'm the kind of person that I just don't want that burning in my in my skull. I don't, I don't want unsaid, unu-cared for pieces of me to be left out there. So I didn't burn any branches, bridges in the corporate world. And I've I've left a, I would say I have a legacy of service, of care, of showing up when it matters and of follow-through. And for me, that that speaks volumes. And so currently, as I'm building, all my clients have come from people that know me so far. I've not had one client so far come to me because of my website or because of a LinkedIn post. They've come to me through my business network. So it's it for me, that's the most powerful testament to what I'm building. And it gives me confidence as I put that backpack on to go, you know what? Like, I know I serve well and I know I have a good reputation in the marketplace, so to speak. I'm gonna trust this process. I'm gonna trust that my character will show up in spades. And so I would say like my biggest sort of asset is trust building, something that I've done my whole career in knowing now it's gonna continue to pay dividends in the future. Okay, that's awesome.

Pedro 12:30

I like that. All right. Now let's talk business for a second. Okay. So people find you through your networking, through the years that you've worked in corporate, referrals, right? And they resonate with your work. And eventually they want to know what working with you actually looks like, Matt. So everyone builds their coaching business a bit differently, I would say. So when someone actually becomes a client, what does that experience look like right now?

Matthew Lindsey 12:55

I love that question. So one of the things that I'm very clear up front is especially in those discovery calls, all the way to the maybe the second or third session. So giving ourselves, you know, three to five hours of work together, I'm very clear from the get-go that they might come to me for marketing strategy, sales strategy, big, you know, operations or trying to scale their business. A couple of my current clients right now are trying to go from like 1.2, 1.3 million to three plus million this year in their businesses. So sure, you got to have the smarts, as Patrick Lencioni might say, you have to have the smarts of the business. You got to couple that. You've got to have that synergy or the cogs of both those wheels have to connect with the heart and the smarts. Meaning, and these are my words. I'm paraphrasing Patrick Lincioni for sure. I'm sure he would say it much much more succinctly and more beautifully. But when you have leaders that are geared towards interpersonal development alongside knowing that they have the right people in place, the right people, right seats on the bus, and they have all of the business things, you know, buttoned down and cared for, you bring all of that together, you have a winning recipe. So when my clients first come in, we talk straight up about those types of things. So my clients know that we might be having a base level work on strategy and ops and all the things that go down to the smarts of the business. But right here in the center of our lives, of our being is our our values, our purpose, what we're about, our character, what we hold dearly, what what aches us, what causes us to stay up at night? And when I hear leaders speak, they might say one word about, we might be talking about ops, but they might say something in a way that causes me to go, okay, wait, you said it this way. Can you tell me more? Or why did you use this particular word? Or what does this word mean to you when you articulate X, Y, and Z? And invariably, it's those questions and those little threads always go back to center of who this person is, what they're about, and what really is nagging them, or what has really been a stumbling block to them. And so not every session gets this deep, but many, many sessions come back to this individual's heartbeat, what they're about, what they're afraid of, what what they're confused about, what they're unclear of. And I love that because you pull on one of those threads, you might head down, they might have come into this session to talk about strategy, but by the end of the session, we're talking about things of the heart or what's going on in their personal life or how they're not taking care of themselves, or you know, negative ways they might be thinking of themselves or imposter syndrome. A lot of different scenarios come up. But those threads are keys to unlock clarity for strategy, clarity for sales, clarity for leadership, clarity for managing others, for teams to come together. It all starts here. So my clients know that well about me. I'm not shy about calling out the elephant in the room. I'm not a confrontational person. In fact, I spent many years trying to avoid all confrontation. And over the years of my own healing and growth and maturity as a person and as a leader, I realized over time you got to lean into those conversations. And when you do that, wow, just so much breakthrough happens, so many epiphanies, so much clarity, so much movement and room to move forward happens. And so I love that. And my clients know that if you're gonna work with me, and that's something I'm learning really quickly now, is what clients I want. Are they resourceful? Are they able to grapple with the difficult questions? Are they able to sit in the uncomfortable silence of the session? Are they am I okay to sit with that uncomfortable silence uh silence as a coach and allow them to explore something that might be really deep? And I want to be very clear, I'm not, I'm I don't see myself as a counselor or a therapist in any way. And I I would encourage any coming coach, and I think most seasoned coaches really understand this. That's not what we're about. We're not trained in that way. That does not mean, though, that we can't lean into these deeper wells, these areas that cause us to really connect with our character, our values, our purpose in life, in in ensure that there's alignment internally so that we can then go out and do what we're doing on our day-to-day job.

Pedro 17:03

Yeah, man. I I have the sense that most people have like a surface level goal, you know, but when they really think about it, they have no answer to it. It's like, hey, I want to buy a new house, I want a new car. Yeah, but what's the purpose of it? I mean, what's the real drive behind it? And when we you at least looks like doing your practice, start pulling up the thread, right? You got that aha moment, the revelation of why am I really doing this, right? So that's pretty cool, man. But I gotta ask you, I guess your work seems pretty hands-on. We're talking about discovery calls, we're talking about uh the practice itself, coaching clients, right? So, and I know you're still building this, right? So, how do you think about capacity? So you don't stretch yourself too thin, right? There's marketing, that's all sorts of stuff that coaches have to deal with.

Matthew Lindsey 17:53

Yeah, no, absolutely. I've lived the burned out life before, and that's one of the one of the reasons that moves me back towards the corporate world in the work that I'm building right now is to help support people that are stretched super thin, that are, are, are confused, that are overwhelmed, that are are feeling like they have to fake it till they make it, that mentality, which I think is a very stressful way to lead. I I I've been there before personally. In my in my growth curve within the corporate world, um, there's a lot of pressure, especially inside public companies, to perform, to show up to work as I would say corporate cosplay, where you you put on the suit, you put on the shirt, you put on the attire, whatever it is, and walk into the corporation, but then you're checking out your humanity and at some level, and it's not allowed in that corporate world. And so people get burned out really quickly. So knowing those types of things, as I've been a solo entrepreneur, which is a whole different thing than being an entrepreneur with a team, being a solo entrepreneur is really difficult in a way that I didn't really quite understand until I started on the path. But capacity is huge. And for me, the thing about that for me is I gotta protect my time with my family. I've got to protect my time with with my own self, my healing, or the energy I need to refill my buckets of energy. I know what that means for me personally. And so right now it's easy to understand, yeah, I do want a more full schedule. I do, I don't necessarily enjoy currently opening up my calendar and seeing, wow, I have a lot of white space right there. That that is for on one hand, is super motivational to continue to putting the backpack on and taking those steps. On the other hand, slow growth for me, my mentality is long term. I know that it takes statistically a couple, two, three years for a coach to build a really solid business where they have an income coming in that's supporting themselves and their family or whatever their needs are, and then a pipeline that's being backfilled. I know that's gonna take a few years. Some people do it quicker than others. Kudos. I'm gonna try to do it quicker than three years. However, I'm also not going to sacrifice my mentality or my energy or my family or my life for the sake of a salary or a full calendar, right? I don't, to me, that trade-off just doesn't meet up. The math doesn't work out. I don't want to work 60 hours a week ever again. Am I capable of doing that? Will I do that if if need be to support clients or whatever? Yes, but I will always try to bring that back into some sort of balance for me personally. So it's it's about sustainability for me. What can I sustain on the path of growth? What what at what speed can I do that efficiently yet thoroughly and not in a way that sacrifices any of that energy or that time with the things I know are that really matter in my life? And and then that long-term peace, knowing that no, I'm in this all in. I've put all the chips in the center of this table. This is what I'm doing until the universe says otherwise, this is where I'm going. And so for me, that is there's a limitless time. Like it's indefinable. It's uh it's a long-term mindset that I have to accept. And for me, that gives me a ton of peace because it's one small step a day. It's put the backpack on. And again, that's not being passive for me. That's about building long-term capacity. It's like someone who may be out of shape. You don't send them to the gym for the first day back into the gym and say, go work out for the next two hours and then come talk to me. No, you, hey, let's go do a 10-minute walk. Let's go do it the next day, let's do a 30-minute walk. Or you know what I mean? You just step slowly into these things. For me, that's the mentality I'm taking into this business is work hard, be diligent, be mindful about all these things, do everything I can to move the needle while not burning out and not comparing myself to the other coaches that may be further ahead, you know, on the road than I am. Okay.

Pedro 21:39

Yeah. Well, that was a lot. I'm still processing it, you know. Especially, I think that that this is not a race. I love it. And also the fact that you're in for the long run, you know. So it sounds like this is going to happen. And yet there is no plan B, you know, because at at a certain level, having a plan B is actually. Accepting the A is not gonna work, you know, at a certain level to some extent. I love the fact that you're just like, this is happening, man, and I commend you on that. And I need to tap into your experience a little bit, you know. Pre-podcast, we were talking, I remember we were talking about pro bono, right? And one thing every coach wrestles with at some point is pricing and how to package their work. So how do you think it about it today? And were there any lessons along the way that shaped how you landed here? And and the reason I asked this is because coaching sometimes it's like a self-worth path. I have all this, like I said, I have all these lots. Should I offer my services for less? You know, that type of mentality. So how does that play out for you today?

Matthew Lindsey 22:44

Man, that's that's the million-dollar question, right? I remember coming out of my certification schooling and and having these conversations with colleagues that are also on the similar path. How do you do this? And what's the pricing? There's no magic answer to that. What I've come to, what I've come to accept and believe about myself is that I have a body of work, right? I have a lifetime of work that has shaped me and moved me to this position that I'm in now. And that for me means there's a ton of different assets I'm bringing to the table that are extremely unique. There's no other Matthew Lindsay like me on the planet, at least that I know about. Maybe I have a doppelganger in in Brazil somewhere that I have yet to meet. But as far as I know, there's no other person like me exactly on this planet, which to me means I have unique assets and a unique way of seeing the world and a unique ability to support and help others along the way. That's deep value. Does that mean I'm gonna go out of the gate and charge what maybe some of these high-end coaches that we all see online are doing? Probably not. I'll work towards that, depending on where, again, where where my heart leads me in my own craft, in my own, again, going back to my values and what I hold dear and what I how I see the world. I'm weighing all of that out. But I know that I think a lot of coaches need to hear this is that we are worth a tremendous amount. Not necessarily we don't have to always put money to we are worth a tremendous amount, but we we shouldn't be shy about what we're offering, where we come from. Accreditation is important. Is it everything? International coaching federation, or UICF certified it, you know, I'm working in the business world again. That matters to an extent, but by and large, most people don't even understand what that means in terms of what the clients, the coaches and understand that, but clients don't really know. Some of them don't care, some of them do, very few do. But my point for me is I'm not gonna undervalue myself. And going back to your original question about pro bono, I think for me that's important. I come from a philanthropic background and worked in nonprofit for a long time before the corporate world. And I get the value of giving back generosity. I believe in that, and I believe that that plants seeds for the future. And the the the the crux of that is you can easily give away your give away the farm, as they might say, and sacrifice your whole family or your your own experience or your own livelihood for the sake of supporting others. We unfortunately need money in this life to do good. Not that that's the only thing we need to do good, but if we really want to make huge impact, it's great not to have a financial burden on top of our backs. That that really slows people down. So I'm working towards a place of knowing that I'm valuable, that I'm worth it, that I've done the training, that I have tons of experience under my belt in the corporate and business world and nonprofit world and everything else I've done in my life that all feed into supporting a client where they're at on the path. And again, that's a unique value. So for me, depends on the the now when we're talking about actual price structure, depends on who I'm working with, right? If I'm working with a large business and we have a six-month or 12-month contract, that's gonna look a lot different than me working with an individual who might be making, you know, less than six figures a year. Uh maybe it's a young man from my jujitsu community, uh, which I do work with a handful of those guys. They just, they're not at capacity, they're not at, they're not at the level of these corporations. So I have to adjust my pricing to work with those individuals. But back to pro bono. I'm at this place, Pedro, where I I know the the value of giving is good, but also skin in the game matters. What I've learned the hard way, I've done close to 100 hours of pro bono work in the last year and a half, and I'm grateful for that. But I I've I've changed my mindset around that, where I will charge, no longer will I do free work inherently, but I might charge people just a few bucks. So they have a mental psychological skin in the game, especially if it's one of these, let me just use the jujitsu community as as sort of an archetype. But uh just imagine an avatar of these jujitsu guys 25 years old, or they're they're they're entering the the their career, they're just starting off. They might be living in an apartment by themselves. They have a heart for leadership, they're one of these people that I want to work with. They have they're hungry, they want to grow, they want to be a better leader, a better man, whatever it is for that person. Yet I know their income, basically. They're they're driving Uber Eats and they're living in an apartment and they're doing jujitsu, and that's kind of their life. It's really basic. And and that's not a bad thing. That's not a judgment. That's just where they are at. But they're hungry and I'm there and I want to work with them. So I'm gonna adjust my payment stream for this individual based off where they're at. Am I gonna undervalue myself in some way? Maybe. But to me, that's like the balance of doing good work and being of service, which is my primary, my primary sort of leading edge of my business is is serve. I am exist on this planet to help people come into true alignment so that they can find out what matters most to them. To me, that's just an act of service. So I'm going to serve and I'm going to help them understand you have to have skin in the game at some level so that you show up, so that you feel like this is of value to you, so that you have follow-through. I think that psychological shift on the client side makes a massive difference. And when they're paying, guess what? I show up different as a coach. I mean, I show up full as fully as I can in the pro bono context, and I feel like I've done that really well. But man oh man, as soon as I started shifting into a payment model for all even the guys that I thought couldn't pay or I thought couldn't afford, everything changed for me as the coach. I started showing up different, started preparing more thoroughly, started showing up more powerfully, more intentively, and doing that that sort of mental and spiritual preparation before a call or before they come to my home office in such a way, even at a really low, low rate, right? There's a psychological shift there. So I hope that makes sense.

Pedro 28:32

It makes perfect sense. I'm gonna tell you why. I used to play Taxes Holdem with my buddies, and that was in the I would say high school time, you know, era, and I were we were like playing for zero dollars right in the pot. And if we added five bucks, man, the game changes entirely. You know, it was a diff whole different game because of a dollar per head. So yeah, before they were all ins, and you know, everyone's bold, everyone's courageous, and then you have some skin in the game as as not as much as it sounds like, but you know, any skin in the game, that what I would say is the key word is potentially commitment, right? Because there's some commitment involved. People tend to change their behavior. So yeah, I get that 100%. Now, Matthew, I'm curious about where you're taking all this, man, looking ahead. Where do you see the business going? Are you thinking about scaling, hiring, or is there a next step you're excited about?

Matthew Lindsey 29:28

Oh man, yeah. So the beginning of this year, I spent the first four or five days of the business week in January, the first week of business, uh doing my Q1 through Q4 plan. I just had the premonition of like, Matt, you you really need to be accountable to yourself. Of course, I have this mastermind group, but how are you building your business? So, what I did is I imagined I had to report to a CEO, to someone that was in charge of my business. And their question to me was, Matt, how are you growing your business this year? Show me. So I did a Q1 through Q4 plan, set my own KPIs, my own metrics in which I'm going to weigh myself against and measure each quarter of growth to set those achievable goals. I made them a few of the goals are stretched goals. I'll speak to those first. One is is income and where am I trying to build? Yes, I'm trying to scale. I I want three more bigger corporate business clients this year. By the end of 2026, my goal is to have four or potentially five larger businesses that I'm working with where I can work in it in and really expand and grow my capacity to support teams, to sort support executive leaders, founders, and entrepreneurs. I'm I'm just so passionate about that world from where I come from. So there's that. And and along along with those clients, I want to have a few individual clients that I'm working with. And then the third tier would be the pro bono work. That pro bono work is really shaped into something unique, though, for me, as I've done a majority of the pro bono work came from the jujitsu community and a few outliers from different parts of my network is uh a men's group. Something that was an idea that came to my head last year through part of my training, through different conversations where I was having with other colleagues and with female colleagues about what men need today in our world. Uh to grapple with topics about emotional intelligence, to grapple with topics around emotion, how how to operate as a male. What is healthy masculinity look like? What is male leadership within the family context look like in our world today? Uh, what does male leadership look like for single men who are trying to date, who are trying to build a family or trying to find a partner in their life? There's there's a whole ball of wax that I'm I'm really I feel really compelled to meet and be a part of that conversation and work with that community. So for me, one of those, one of the pieces of my business this year is exploring and learning how I can serve men better. So I launch actually this this month on the the the end of this month on the 28th, I'll be having my first meeting with the men's group that I launched uh starting actually in December of 2025, just a few months ago. I I reached out to my jujitsu community and just did a poll. Who would be interested in a men's group with a with a small subscription payment? Again, going back to skin in the game, the difference of, and it'll be $10 a month. It's not much, it's not really a business play for me at all. In fact, most of the money that I'll that'll be coming in from this community will be going back into this group of men, uh supporting retreats and and snacks and drinks and those types of things just to keep us engaged together. Uh, but I think there's something there. I think there's something because there's 22 guys that immediately signed up to be part of this men's group. And I don't know what that again, Pedro, I bring it up because I'm super passionate about it and I'm super curious about where it's going because I just don't know. I've never led a men's group like this. I've been a part of different men's groups, but hearing, especially from female colleagues that are either married or single or dating didn't matter, but they have a perspective and they have an opinion around what this means. To see their exuberance and to see sort of their passion rise up and really push me, saying, Matt, go do this. We need more men to step up and help other men. I heard that loud and clear from the females in my life that I really respect and look up to. And so I've I've taken that as just another sign that, man, there's something deep here. So I'm excited about what this could become. I don't know if it'll be bigger than what it is right now, but I have a feeling it might be.

Pedro 33:27

That sounds exciting, man. I wish Kevin uh would hear this episode. His the other podcast host, his like 13 years in jiu-jitsu. He's like super into the thing. And I'm I'm Brazilian, so he eventually he tries to talk with me about Brazilian jiu-jitsu, but that's not really happening, Kevin. Sorry about that. I'm more into soccer or football, as they call it in the UK. Okay. Yeah, man, that's exciting. Just by hearing you, I got I got excited. You know, I got goosebumps. And of course, whenever we're aiming towards the next chapter, man, there's always something we're refining in the present. Like, what are you currently trying to improve or tighten up in your business that are I'm not sure if they serve our KPIs or how does that play out?

Matthew Lindsey 34:11

Yeah, uh, so yeah, accountability around my structure plan. So I meet every two weeks with my mastermind group of coaches and leadership folks. And each each two weeks, every two weeks I have to report back to them where I'm at on my Q1 plan, because we're currently in Q1 2026. And so I get every two weeks to go to them and say, here's where I'm at, here's what I've done, and here's what I'm going to do in terms of my action steps following the next two weeks. So having that sense of accountability is massive for me because it keeps me focused, it keeps me driving forward, it keeps me in sort of a creative mindset too. It's not so much pressure that I feel overwhelmed by it. It's just enough pressure for me to go, you know what, I have other people that are going to ask questions. And so that accountability is huge for me. And then it's also just like continues to put me in an innovative creative mindset of, okay, cool. Let's think about what are creative ways to build this. How can I tap into my network? And so going back to your question of how what am I working on this year's, one of those big things is tapping into that network in a strategic way. In fact, in our upcoming call, this this coming Monday will be our group call, our mastermind group call. And this is the topic that I'm bringing to the table is using our network in a strategic way, not overusing it, not abusing it, not fleecing it, not going out and just kind of blasting everything out into the ether and hoping something sticks, but really being mindful about, okay, I have a big network. Who are the key players? Who are the first people I should really talk to? That's one thing I haven't done yet, Pedro, right now in the business building side is really lean into that corporate network. I've been saving it. I've been savoring the fact that I have a great network and I have a great community around me in the business and corporate world that I've built over many, many years. Like you were saying in the intro, 12, 13 plus years of doing that. And I'm excited about this year learning how to utilize and collaborate with my network. One of the ways I want to do this is in Denver, Colorado, where I live, in Boulder, Colorado, is a very famous town just north of Denver, about 45 minutes north of where I live. There's huge entrepreneurial hubs, a lot of startups, a lot of founders, a lot of people in the world of building new businesses, tech, a lot of tech around Colorado, is they have business weeks and tech weeks and startup weeks and entrepreneurial weeks where they have conferences and people come together and they're networking and they're they're listening to web uh to speakers and webinars and all sorts of modalities. I'm one of my goals for Q1 is to submit a proposal to Denver Business Week to have a group of coaches host a panel. I'll be the host, or one of us will be the host, and we'll share with these entrepreneurs and these founders what is coaching in the business context, what it's not, what the data shares around. There's a there's a plethora of actually really good hard data from Harvard and Deloitte and McKinsey and all sorts of different institutions that have utilized the data resources around what effective coaching looks like and what the return on investment, the ROI, looks like within that context. And from some basic studies that Harvard put out a handful of years ago, for every dollar invested into coaching, there's a $7 return on that investment in the business world. This is coming from big data sets and from large companies that actually do this work and actually invest into third-party executive coaches to come in and support that. A lot of entrepreneurs and founders don't know that. A lot of investors don't know that. But imagine entrepreneurs and investors that work together saying, you know what, the investor says I'm going to protect my investment by getting you all a third-party coach to support the team. Because 65% of all startups fail because of founder contention, because of relationships. But when you have that Bill Campbell, that Steve Jobs kind of persona within the network, within that group of team, or within that team embedded in some way, wow, that that individual can help really smooth and down the rough edges, bring people together, help bring that clarity so that the founders and those teams and those investors can really see the return on their investment. So that's another, another, another huge business goal for me this year is getting in front of that audience, using my network, getting in front of those audiences and really sharing out this message of no coaching is real, it works, and it's incredibly valuable for everybody involved.

Pedro 38:29

I love that, man. And especially the fact that you mentioned networking, right? So that reminded me of a guest we had here. That's a shout out to Anthony Harris. I was talking with him uh about his origin story, just like I did with you. And he was like, you know how I developed myself into a coach? We have this quarterly meeting of just my family. And once in a while, one of a family members introduced how they can support the family, right? And he he said, he said he'd like he did the presentation about how he could support them into their resumes, right? And that landed. He actually helped a family member on more than one occasion to land a better job. And that's what made him a coach. So it's networking, you know, and it's a and it it can be with your family as well. So I love that, man. That is so cool. And if someone listening wants to connect with you or follow your work, Matthew, where can people find you and connect with you?

Matthew Lindsey 39:24

Yeah, I would say my website and LinkedIn are probably the primary ways currently. I am actually going to do another stretch goal that I didn't mention this year, and that that is to get involved in more social media for two reasons. I I don't believe social media is going to be a way for me to gain more clients, but it's a way for me to share my heart, to share my message, to talk about things like organizational health and leadership and masculinity and some of the things that we talked about in this podcast so far. For me, and I would encourage other coaches to potentially explore this for the reason of people need to hear. Not everybody's gonna hire you, not everybody's gonna know about you, but the more that you can expand your message for again the unique, unique way that you do it as a coach, who you are, how you're built, people need to hear that. And maybe there's only one, two, three, or four people in the whole world that'll resonate with that message. But guess what? Their life might be changed and that ripple effect might go out in a way that you never understand. But for me, it's it's both also a way to stretch, right? Because I'm uncomfortable in front of the camera. I'm uncomfortable on social media. I'm not a big social media person. I barely get on it. I try not to. But there's there's an interesting change in what's happening with AI, with, with the need for connection with real humans and with real community. And so I I really feel like that's a that's something that I'm gonna be leaning into more and more over over the next that's part of my Q1 goal, is is building this channel, getting out there more and expressing myself more because I know that's gonna change me personally. So eventually we'll have that. But right now it's Matt S. Lindsay.com and my LinkedIn as well. Okay.

Pedro 41:01

Awesome. You know, there were a few things you share today that really stay with me. I would say that Bill Campbell book, you know, in a way everyone talks about Steve Jobs and all of that, but looking behind the curtain or who's really making the difference. I really like that you did that and and how that uh in a way inspired you to become a coach, right? Also, I'd say you have one at home, right? Your father asking you, hey man, why don't you just do this full time? In a way, it is coaching because he gets you, you know, and he didn't tell you what to do. So I really like that. I had a pinpoint also, the fact that you were kicked out of your own business that you founded, you know, with over 40 layoffs, and how you turned that into an opportunity. And you're not just sobbing in a corner, you actually made that a real opportunity and shifted your career. So, yeah, that's awesome. I really like that. And you mentioned something that really sparked my attention, which is the corporate cosplay, right? The Comic Con corporate cosplay. Which and that's funny because uh I was reading about this a while ago. How teens on school they tend to have, you know, that lack of identity, and they have a somewhat of a tribal movement towards, oh, I'm gonna be a punk or I'm gonna be an aw or whatever, you know, and they tend to move towards a group until they build their identity. It's somewhat like that. I may be rephrasing it wrong, but the whole point is we go through that and we go to college just to get back into that old way, you know, of trying to get into corporate, suppressing who are who we really are, who who and try to cosplay at something and adapt. I get it. We want to adapt, we need to pay our bills. I 100% get it. I worked on corporate, but I like the way you framed it, you know, because there is uh our true self, they're they're hidden out there and and they're still there, you know. You're not uh X, Y, and Z company, just to put it out there. I also commend you on the Pro Bono uh the Jiu-Jitsu community, you know, the healthy masculinity and all of that. So, man, I appreciate what you do, and I appreciate you being here and sharing so openly today. It was great having you on, Matthew.

Matthew Lindsey 43:16

Well, Pedro, I appreciate all that encouragement. I I receive it and uh it's just made my day to hear that reflection back from you. And I just want to say thank you to you and the purple circle community for what you're doing, what you're building. I'm excited about what you guys are about and and giving a platform like me and and for so many of your guests that you've had on before a way to explore and express and just be part of the conversation. So thank you for that.

Davis Nguyen 43:42

Appreciate you, man. That's it for this episode of Career Coaching Secrets. If you enjoyed this conversation, you can subscribe on YouTube, Spotify, Apple Podcasts, or wherever you're listening to this episode to catch future episodes. This podcast was brought to you by Purple Circle, where we help career coaches scale their business to $100,000 years, $100,000 months, or even Hundred thousand dollar weeks, all without burning out, and making sure that you're making the impact and having the life that you want. To learn more about our community and how we can help you, visit join purplecircle.com.