Navigating Uncertainty: Scott Stirrett on Turning the Unknown Into Power

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Step into the world of success with Your Brand Amplified, the ultimate podcast designed to unravel the intricacies of thriving businesses. I'm your host, Anika Jackson, and I'm on a mission to uncover the stories, strategies, and secrets that have propelled entrepreneurs and business leaders to success. What if the thing you're trying hardest to eliminate from your business and your career, uncertainty, is actually your biggest competitive edge? My guest today built a national organization from a single idea. Scott Sturritt founded Venture for Canada in 2013, grew it into a charity that raised more than $80 million, And supported over 10,000 young Canadians, and in 2026 received the Meritorious Service Medal from Canada's Governor General. Then he did something most founders never do. He walked away at the top. Now he's searching for a business to buy and run for the long term, and he's written the playbook for thriving in unpredictable times, something we all need to know right now. The Uncertainty Advantage. We're talking calculated risk, antifragility, Why following your passion might be steering you wrong, and the skills that matter most as AI reshapes work. So, let's get into it. Scott, thank you so much for joining me on Your Brand Amplified.

Thanks so much for that lovely introduction.

Yeah, well, it's all you. So, let's talk about your new holding company, Carrying Place Holdings. You know, it's after the old Canadian word for a portage, that stretch where you pick up the canoe, carry it overland to the next waterway. It feels like a pretty fitting description for where you are right now. So is that on purpose? You know, we'll get into, of course, some of the other things in your business career, but I'm really intrigued by that.

Yeah, I love the name Carrying Place for a couple reasons. One is that it is very distinctly Canadian. It's like a Canadian term that is used throughout history. There's some places that are actually like communities called Carrying Place. Like there is a Carrying Place Ontario, for instance. 2 is, I think it's a great metaphor for people who look to buy businesses from retiring entrepreneurs and carry forward that legacy in the long term. And 3, I chose the name because I found that it was distinctive. I'm not trying to be private equity. There's a lot of private equity names that are somewhat generic, like Sweeping Meadows or Blue Lake Capital. And I wanted a name that was a little bit unique and more memorable because I think what I'm trying to do around entrepreneurship through acquisition related to long-term hold, long-term value is a little bit different than what a lot of folks do when they buy businesses.

Yeah, it certainly seems like it is. We hear about VC companies, private equity companies buying, taking companies apart, Right? With a little bit of an unknown. So talk a little bit about what your search looks like that's different and what a week looks like right now in the middle of the search for a business to buy.

I am one month in almost exactly. I started September 1st, so it's a good time to ask that question. And the first way I would answer it is to say that every week is different when you are full-time searching for a business. Sometimes you might be at a conference for a couple days meeting with intermediaries or people looking to sell businesses. But Anika, I would say a typical day is a few things. Like one is spending some time cold emailing business prospects or cold calling. That is a part of the day. I'd say the second part of almost every day is interacting with an M&A advisor in some kind of way who is representing a seller. And for context that I'm dealing with both people who are selling their businesses and they're not using an advisor, and I'm dealing with people who have retained kind of professional M&A advisor. And then I'd say a third component of pretty much every day is also continuing to research and prospect kind of new industries, kind of areas of focus. And that's something that I spent some time doing today. And every day is a little bit different. If you're interested in entrepreneurship through acquisition, what I would say is one of my reflections from a month on is just the importance of like endurance. Like it takes time to find the right business. And I'd say second is that to be okay. I think entrepreneurship through acquisition can work well if you're someone who is good with spending a lot of like quiet time or solo. Like if you're really extroverted and social, which I can be, But if you really kind of struggle with like kind of working somewhat solo part of the time, I think that ETA entrepreneurship with acquisition can be perhaps a little bit challenging.

Interesting. We're going to get back to all of this, but I do want to dig a little bit into your background. You grew up from Dartmouth, Nova Scotia. You went to Georgetown School of Foreign Service and you had Goldman Sachs on your path. Pretty certain route, right? You knew exactly what you were going to do. So take us to that moment when you were going through your career and you decided to start a charity, right? That was completely unknown. What was that decision like? What did that decision teach you about risk and how did you come to that decision in the first place?

It was definitely one of the biggest bets, if not the biggest bet that I've made in my career. I first had the idea for Founding Mentor for Canada shortly after graduating from Georgetown University. And I had a return offer to go to Goldman Sachs. I had interned at Goldman Sachs between the 3rd and 4th year of university. And a couple, I don't know, I'd say a month before I was just starting at Goldman Sachs full-time, I had this idea of, there was this organization called Venture for America and I thought, why not try to create a Canadian equivalent of it? So I quickly incorporated or I quickly incorporated and bought the domain ventureforcanada.com, ventureforcanada.ca. And then I just started cold emailing people and it started to kind of snowball over time. And then by, I'd say February or March of the following year, I began to realize that this Venture for Canada thing actually had legs. And at the same time, I realized that Goldman Sachs being a part of just this massive financial institution as a quite entrepreneurial person wasn't a good fit for my skills and interests. And then in April 2014, I decided to Resign from Goldman Sachs and to dive into building Venture for Canada full-time.

And what did you see that was unique about the Canadian market versus the US market? You thought, this is good. We need to do something around venture in Canada, but I can also be the one who shapes that because I know I've been, had a foot in both soils, if you will.

There were, there ended up being significant differences between Venture for Canada and Venture for America. Initially, they were quite similar though.

Hmm.

And I'll kind of walk through maybe how they changed over time. I'd say the operative distinction from the get-go between Venture for Canada and Venture for America is that Venture for America was about recruiting, training, and supporting recent grads from elite American universities to go work at startups in cities facing economic challenges across the United States. So think kind of Teach for America, except for entrepreneurs. The Canadian context, we were always about just building up Canada. And getting young people to work in enterprise and Canadian companies regardless of location. Now, over time, Venture for Canada evolved in really significant ways. In many ways, the program that Venture for Canada initially launched on no longer actually even exists. I would say a version of it kind of exists, but the organization completely changed. So today Venture for Canada has an operating budget of $15 million. It delivers half a dozen different programs. It is continuing to thrive and I'm still involved in it a little bit in terms of advising the CEO. But it was, you know, I think if I reflect back on that journey, I think one of the great things about Venture for Canada was that we didn't feel too locked into the Venture for America version. And I think the best entrepreneurs, the best entrepreneurial organizations are willing to adapt with the times. And that can include discontinuing the initial thing that launched the organization. Today, Venture for America actually doesn't exist. I would say somewhat of a successor organization to it does exist, but Venture for Canada still exists with its branding while Venture for America is extinct. And that is a testament to, I think, the fact that Venture for Canada evolved in ways that were quite different. The maybe final thing I'd share with listeners is Sometimes you might have, your idea might be sparked by someone else's idea, but it's really important to be okay with letting your idea evolve and change based on new information and to not be too beholden to your initial inspiration.

I think that's an important lesson that people lose sight of, especially in the world of entrepreneurship, right? We want to make sure that we've told everybody in our families, our friends that we're going on this venture. Maybe they think we're a little crazy, right? That we don't want the security of a steady job and a paycheck from somebody else. And they're not, they don't really understand how we're going to make this thing work. And then we do it. And so I think sometimes we feel like we have to continue pursuing a line even though perhaps we should make that shift that you're talking about just to make sure that we are proving ourselves, if you will, to those naysayers.

Totally.

Yeah.

I think that That can be a huge factor within kind of entrepreneurship. And yeah, it's important to have that kind of self-reflection as, as an entrepreneur.

And when you look at Venture Canada, where, what were some of the hiccups that you had to, you know, those bumps in the road that you had to navigate?

So many, uh, particularly in kind of the early years. I think the first was that the funding model for Venture for Canada ended up being a lot different than the funding model for Venture for America. One significant difference between America and Canada is that the government in general plays a much more active role, I would say, in a lot of Canadian society than, than in the U.S. That's to say, government has a huge impact on Americans' life. I lived in the U.S. for 5 years. I get that. But I think that there's a lot more services in Canada that are done by the government than in the U.S., where things tend to be privatized or run by private individuals. Now, where that is links to Venture for Canada is that Venture for America was able to raise millions and millions of dollars from billionaires and really rich people to fund their operations. And I started Venture for Canada. I thought, oh, I'm just going to convince really rich people to write me $100,000, million-dollar checks to get this organization going. That was not successful at all. That was partially because I was also 22 when I launched Venture for Canada. I didn't have this massive Rolodex of people I could just call to make major donations. And in general, in Canada, it's way harder, I think, to do that successfully. So one of the challenges in the early point was just having, getting the organization funded in the first year, full year of the organization. We had like $150,000 that we raised, like that was it. And that was for 2 full-time employees and running A month-long training camp with 30 people. Like we ran it on a shoestring and it was really tough and we were able to persist and kind of keep going. Now I'll flash forward to sort of a second major hiccup or challenge we had, which was that by late 2017, now hard to believe 9 years ago, the organization was at the precipice of significant kind of growth. And it was also a really stressful time for a lot of the existing employees. And we had some kind of HR challenges and all of a sudden we lost like half the team. And then the organization got all this funding and when we grew the team from like 3 people to 15 employees in the span of a couple of months, and that really almost broke the organization. It was incredibly stressful and I had to work kind of around the clock for 6 months during this time. But ultimately laid the path for the organization to be much larger, much more kind of impactful. And if I was to say maybe a third major challenge, I think that was overcome was just learning to kind of scale the organization kind of over time and building the systems to support that scaling. Like when you first start out, there's no accounting system. I remember paying the first employee of Venture for Canada via like e-transfer and then having to learn, oh wait, there's like ADP and payroll and you need to like, there was all to say is that there were so many unknown unknowns for me as a first-time entrepreneur. Now, as I do entrepreneurship the second time, it's still challenging, but I go into it with a lot more built-in kind of knowledge.

Right.

And I think one of the challenges that I had a lot is that when you're a first-time entrepreneur, you're learning so much on the fly that it can be kind of overwhelming. And that you're also in a position where you can end up making a lot of mistakes because you're in domains that, that to my point on unknown unknowns, like you don't even know what you don't know. Which makes it challenging to navigate.

Yeah, absolutely. Well, and that plays directly into what you actually say could be a superpower or strength, right? The uncertainty advantage. So, can you talk a little bit about the book and what was the decision like to say, I need to codify this, I need to write everything down, and I need to teach other people, you know, about some of the things that I've learned and some things that they can do?

I was motivated to write The Uncertainty Advantage for 2 different reasons. I think the first was that I had seen personally in my life that fear of uncertainty is one of the main things that holds me back at different points, that I've loved uncertainty at some moments in my life, like when I quit my job at Goldman Sachs to go found Venture for Canada. But in COVID, I really struggled with uncertainty. I was diagnosed with obsessive compulsive disorder. I struggled for probably around a year, went through treatment, And really built out my uncertainty muscles kind of over time gradually. And I've seen firsthand in my life that you can go from fearing uncertainty to loving it. That today in many ways I'm embracing uncertainty more than at any other point in my life, including through the business acquisition search. And that the ability to thrive with uncertainty is a teachable skill. So that's a first piece of what motivated me. The second is that I've seen that this doesn't, just apply to me, that at Venture for Canada, where we've helped over 10,000 people launch their careers across Canada, I've seen that fear of uncertainty holds people back from launching businesses, taking risks, moving to new places, trying new things. And in a world that is in many ways defined by rapid change, one of the most important skills that we can all learn to develop is the ability to cope with and thrive with uncertainty. And there are many books out there about uncertainty, about the importance of learning to thrive with it. But what's unique about The Uncertainty Advantage is it's the first book that I know of, of its kind that focuses specifically on early career professionals, people in their 20s and 30s, and advice for them at a time that is really uncertain in your life, which when you're graduating from university or college for the first time, starting out in your career of how do you navigate all the uncertainty, not just out there in the world, but in your personal life? And how do you do that as a young person?

Yeah, those are all things that I see a lot. Obviously have students who are going straight from undergrad to grad, have students who've been in the workforce and are coming back to grad school, and some of them, they already have a career, so this is going to enhance their career. For those who are trying to get into a new field, this is a really stressful time. And so I see all of that uncertainty and I see people getting a master's and going, ooh, I actually need this other master's as well. Or just trying to break through to that next level of, are they going to go work for somebody or are they going to become an entrepreneur? And are they becoming an entrepreneur because they're passionate about it or because they feel like they have to?

Yeah.

And I think that there are entrepreneurs of convenience and then there's entrepreneurs of necessity, and then there's entrepreneurship because someone's driven to want to do it. And all to say is both can result in kind of great outcomes. I think with entrepreneurship, sometimes people who are entrepreneurs can kind of hold entrepreneurship up as this pedestal. And it's not this question of entrepreneurship is the best path for everyone. I think it's about entrepreneurship is an amazing path for some people. And I do think entrepreneurship skills can be somewhat like learned, but I also think that some people are innately better suited to entrepreneurship than others. And with career development, what's so important is figuring out what is your career person kind of fit. And I think it's important to do that without any judgment on yourself. We all have different answers to that question. And, you know, part of my mission with Mentorship Canada was to help more people who could be entrepreneurs, who potentially it is a great fit for them, but who have never really thought about it as, as an option.

Yeah.

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Well, and, and you did mention, and it was a perfect segue 'cause you did mention your OCD and that diagnosis, and it strikes me as almost the opposite, right? Of if you have OCD, you want certainty, you're trying to create a world around yourself with certainty, yet you are also, you've learned how to thrive with uncertainty. Um, I believe part of your treatment was exposure therapy. So practicing sitting with uncertainty on purpose. Can you talk a little bit about the OCD, the exposure therapy, figuring out how to navigate wanting control and wanting things a certain way and systemized with that uncertainty?

Absolutely. And I think maybe first what I'll do is for listeners, 'cause there's a different kind of awareness about OCD, is I'll give a little bit of context about like, what is OCD? How is it treated? And what are maybe some of the broader kind of lessons for people, even if you don't have OCD? First thing to note is that OCD is a relatively kind of common mental illness that I think is estimated to impact like 1 to 3% of the population. It can be quite serious. I think sometimes people think of OCD as this thing that is just somewhat trivial and involves like washing your hands a lot or being afraid of germs.

Mm-hmm.

Certainly that can be it at the more moderate level, but also OCD can be really serious. At one point, the World Health Organization noted that OCD was one of the top 10 causes of disability in the world. And it can be linked to hoarding. It can be linked to all these things that are more extreme kind of like behaviors, people not leaving their house, uh, shut-ins. And what is OCD? I mean, it's sort of 2 core things. I think the first is that it's avoiding things that cause you discomfort, often related to uncertainties. So that could mean you're afraid of driving, so you don't drive, or you're afraid of germs, so you don't touch any doorknobs. And what happens is those things can be relatively minor initially, but then over time they become really limiting and you're avoiding a huge amount of things. The second is that you end up having compulsive behaviors. that, uh, you're due to give yourself an illusion of certainty. So I'll share one. When I was in high school, it was like before I would have major exams studying, I would do this little like jump, uh, thing where it was around like, and at the, the time I thought it was just like good luck, but in retrospect it was like, uh, more sinister. Uh, it certainly became more kind of over, over time. And that's where with OCD you have to be careful cuz there can be little things that you do and then you start to begin to realize, oh, that's actually compulsive behavior. I need to, to stop it. So how do you treat OCD? Going back to the causes, or I'd say the elements of the illness, is that you first have to confront the fears that you have. So for me, like 5 or 6 years ago, I didn't really drive. Now I drive all the time. Earlier today, I drove 45 minutes to an orthodontist appointment and back. And do I love driving? No, but I drive all the time. And that was— I mean, if I hadn't gone through the treatment for OCD therapy, I don't think I would be as active of a driver today. The second thing is that you stop the compulsive behaviors. And that means, you know, for instance, if for when I was sick, often, like if I had a cold, I would end up Googling cold symptoms all the time. I'm just getting over a cold now. And I, that comes top to mind because I remember in the past, you know, when I was having a cold, like Googling 20 times in a day, how many times do you, or how long does a cold last? And This time I didn't do that at all. All to say, sometimes I can still, and I think most people with OCD have compulsive slip-ups. Like, they're, you're not like cured of OCD. But I do think it's important though, for listeners to understand that people with OCD can have amazing, fulfilled lives. Like in some ways, the last couple years of my life have been some of like the happiest and most fulfilled. But I think what's important to note is that there's sort of, at least for me, there really truly is like life Before exposure and ritual prevention therapy, which is the name of the therapy I just described, and after. Not to say that my life— I think my life in the year or two before the treatment was not as good. But, but I think even in my 20s, I was a much more anxious person. I was much more fearful. And I think going through that treatment really changed my life. It did feel like it was like a Scott 2.0. And if you don't have OCD, it can be hard to describe. And the reason I share this is that I think maybe there's someone listening to this who will one day be diagnosed with OCD, and you might be really down on yourself and you might think, my life is never going to be the same. For me, it was really tough. The treatment, in many ways, I ended up feeling worse initially because it's like you're detoxing, right? All those compulsive behaviors are gone. You're being confronted by the things that, that scare you. I actually felt worse when I started the treatment. But it ended up on the long term, medium term, giving me, making me feel way better, really broadening what I can end up doing in my life. And the great thing about OCD treatment is that there is a ton of evidence-based research on how to treat it, and that it doesn't need to be treated with medication. I never took medication, and I did it purely behaviorally. And the final thing I share is that I think even if you don't have OCD, I think that some of the broader lessons around exposure and ritual prevention therapy relate to a much broader audience of people. And that's that the more that you try to run from uncertainty in your life, the more that uncertainty tries or begins to control you.

Hmm.

Yeah.

As Robert Frost once said, the only way out is through. And in a world where there's a lot of change, I think you need to be intentional about building your uncertainty muscles, just like going out in the gym or maintaining physical fitness. Even if you have a good relationship with uncertainty today, that skill can atrophy. And everyone needs to be intentional about building that uncertainty muscle. And I think that that's one of the unique messages of The Uncertainty Advantage. It's somewhat trite to say that the ability to thrive with uncertainty is important today in a world that changes. But what is, I think, less trite is this emphasis that the ability to thrive with uncertainty is this more broad, cross-cutting kind of skill, and that everyone needs to develop this across 6 different dimensions, which I talk about in The Uncertainty Advantage.

And let's talk a little bit about The Uncertainty Advantage. Self-compassion is one of the pillars in your book. Business culture right now, we're seeing so many different things, right? We're seeing people who are going towards the grind. We're seeing a lot of people are saying, no, that's not the— especially younger generations, right? They're not standing for that. They're saying, no, I need to take care of my mental health. I have these other things. I see it as both in my own experience as a business owner and going through health issues and realizing, oh, I can't work as much as I want to. I'm not going to be able to deliver the things that I promised myself and my team I would be able to, and having to do complete resets this year even. And I see it in my students with maybe they can't get something in on time because they're dealing with a mental health crisis or somebody in the family, something's happened. Or we have fires or, you know, all of the different things that are happening in the world. So I do, I agree that self-compassion is something that's sorely needed, but I'd love to hear a little bit about what it means to you. And then also what are those pillars and what are those things that people will learn in the book?

So there are self-compassion, I think is arguably the most important thing that you need to thrive in an age of uncertainty. Because self-compassion is what keeps you going when you eventually face setbacks, which we all do in life. And we all have bad luck and we all have ups and downs. And I share this because at times in my life I have been incredibly unselfcompassionate and I can be a huge perfectionist. And that's something that I can still struggle with to this day. But I think sometimes being kind to myself, even this week when I had a cold, to be like, hey, you know what? Let's like dial it down a little bit. Like, let's heal, let's feel, feel better. Or even I was training for a marathon and I had this back spasm a couple weeks ago and I couldn't do the marathon even though I'd been training for 6 months. The back spasm was really bad. Like I couldn't barely get outta bed for a couple days. The back's now, my back's all better. But that, that was, uh, but I was, I felt really sad for myself and then I was like, you know what, this is, this is annoying and it's okay to feel, this is bad luck.

Yeah.

And, uh, it's okay to feel some compassion for myself and, and what would a friend say to me going through this? And Eventually I kind of got over it and started feeling a lot better. But in an age of uncertainty, I think the ability to kind— be kind to yourself is really critical. And one of the most important, I think, takeaways for a listener is just when you're to foster more self-compassion, think about how you would talk to a good friend when they're going through a challenging time and try to do that for yourself. In terms of the latter part of your question, which are is what are the 6 core pillars of the uncertainty advantage? They are self-compassion, which we've talked about, but also adaptability, which is important in an age of uncertainty. And one of the things I think is maybe a little bit more novel on that point is that I think it's really important in order to be adaptable, to be really clear about what is your life purpose and mission. And that's because otherwise, You can be too adaptable. The third pillar is around antifragility, which is the importance of not just tolerating disorder, but actually benefiting from it and becoming someone who grows stronger in the face of setbacks. And I think we all know people sometimes in our lives who seem like they emerge stronger from these storms. One of the tangible pieces of advice I talk about in the book is just the importance of building your risk-taking muscle every day because How do you build your uncertainty muscle? You build your risk-taking kind of capacity. And that can be as much as like asking a stranger out for coffee. Like there's lots of little things that you can do to, and everyone has their own risk-taking capacity and starting points and socioeconomic realities, but building your risk-taking muscle is really important. The fourth is around the importance of entrepreneurial mindset of just being able to identify and act upon opportunities to create value for others. And that this isn't just about launching a business, it's about constantly experimenting, and especially in a world where there's new opportunities emerging all the time. And the 5th pillar is around the importance of generalist skills, which are essentially some of the skills that are valuable across a wide range of domains, whether that's public speaking, emotional intelligence. And a core piece of advice is just picking one of these skills and thinking, okay, this is one thing that I really want to focus on. To become 20% better at this year. And the final pillar of the uncertainty advantage is network building, which is really important in an age of uncertainty where who you know is more important than ever. And one piece of advice that I have in there is the importance about building a network that is both wide and deep. Your acquaintances are people who will most likely help you get a job or sell a contract, but your friends are the people who are really going to help you In terms of advice, uh, socio-emotional support during the ups and, uh, and downs. And I think sometimes advice around network building can be too polarized and extreme of invest in only deep relationships or invest in only building a really wide social network. Both are, are really, uh, important.

Yeah. I would argue as an educator, that's probably one of the most important parts of why my students choose to go where they're going, right? Is that network, is the network that they're going to build. Yes, they're building skills. Yes, they're working a little bit on their passion, perhaps coming up with something entrepreneurial, but that network that they have is, I would say, our, probably our, our biggest selling point. So I absolutely agree with that. And I, I am curious a little bit on the passion question, right? Because we want people to love what they do. But there is that moment, you know, ikigai is something that we talk about a lot at the university and making sure, yes, it's something that you're really passionate about, but you also have a skillset and it's also something that can make you money. So where do you see people going wrong? I want to hear your pushback on the follow your passion advice.

I think follow your passion is often very poor advice. It's kind of Cal Newport popularized in his book, So Good They Can't Ignore You. I think that it can be bad for a couple reasons. I think one is that our passions change over time. So follow your passion is kind of somewhat of a misnomer because there is no set passion. It is ever-changing. 2 is that some often the advice, follow your passion implies one passion.

Yeah.

When in many cases we have multiple passions. And 3rd is that a lot of times, to your point, passions aren't necessarily monetizable. So just purely following your passion can result in negative outcomes for a lot of people. I think what Cal Newport talks about resonates with me, which is that we often need to focus more on how do we develop skills that make ourselves useful for other people, useful to the world. And in doing so, we discover our passion. Like my passion for entrepreneurship acquisition started to evolve from like a university class at Georgetown 13 years ago. And then Through Adventure for Canada, we launched a program to train people to buy businesses. And then I thought, I interviewed all of these people who didn't, and then I kind of fell in love with the idea. Now, 20 years ago, could I have known that this would be the path that I would do? No, but it evolves gradually. Likewise, when I was 17, I probably, I would have no idea that I would've ended up to go found Venture for Canada or that I would end up writing a book about The importance of uncertainty for early career professionals. And likewise, there's things that maybe I'm going to do 20 years from now that I'll have no idea about that I have a passion for it today. And I think that sometimes we really want to control our lives and kind of careers. And to say, well, it's not like we are just fate and we have no control over our trajectories. We do. But also I think sometimes letting things like flow and letting passions emerge and kind of change and having this experimentation mindset is actually far more liberating than this somewhat didactic and rigid advice of follow your passion.

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And, uh, you talked about building little risks, right? So that we have that muscle. I'm wondering what's a small risk that anybody listening could take right now this month to start building it?

I've done—

asked this question to dozens of different sessions interactively, and the one that comes up by far the most is Going and getting coffee with a complete stranger, which is one I mentioned earlier, but many people have a huge fear of it. It's funny, like I was sur— I don't have as much a fear of this, but I think it is something that for most people, it is actually a huge thing outta their comfort zone and that it can really reap a lot of professional benefits, like long-term. I think a lot of people, like most people out there do not do this. They'll get coffee with an acquaintance, but they won't do it with a true stranger that they do not know. And the reason I kind of harp on this is that I think that if I was to pick one piece of advice that I think maybe would resonate with the most number of people, it's this, because I think it's relatively easy to do. It doesn't take you that much time, and it can maybe genuinely make you feel out of your comfort zone in a way that also adds value to you and your life and career.

Yeah. Okay. So everybody heard it here. Do that coffee with a stranger, whether it's virtual or in person in this world. Uh, you've worked with more than 10,000 emerging leaders. Can you talk about someone who did turn an uncertain moment into an advantage?

Yeah, uh, absolutely. I would share one specific Venture for Canada fellow alumni. Who he was working in a really kind of more like chaotic workspace and he had done really well within that company. But then he ended up quitting because he was just kind of frustrated with the company and he said, I'm going to go and be an entrepreneur. And he explored a bunch of different ideas. He ended up selling a company for like tens of millions of dollars, did well, and now I think will eventually go launch another company. But he took a moment of uncertainty of kind of a career setback of dealing with a more frustrating workplace situation, and he channeled it into a ton of entrepreneurial success. And I share this too because I think there's a lot of entrepreneurs, like you look at Michael Bloomberg, where he founded Bloomberg was that he got fired from Salomon Brothers and then ended up going to found that company. I think a lot of great entrepreneurs go and create these companies after experiencing a moment of significant uncertainty and then saying, you know what, I'm going to bet on myself and I'm going to go build something great.

Yeah, that's a great example. And I think another thing, you know, yes, that happens often. And I will say that I've had businesses that I've merged with other big— bigger companies thinking it was going to be a better experience. I've ended up leaving those and going on to say, okay, what's next? What am I going to do next? So I think I have had a career that's always been in that zone of uncertainty a little bit and figuring out what is that what next. But I'm curious because we also as founders and entrepreneurs often get that shiny object syndrome. We see something and we're like, oh, we love these things and we're skilled at them, but there's this other thing that we should maybe be trying because we see You know, for instance, oh, everybody needs to learn about AI. Maybe we should move and shift to teaching people about AI. So I'd love to hear a little bit about your perspective on that. How do we become adaptable without constantly being, you know, changing direction, looking at that next shiny object?

Yeah. And I, I think some really entrepreneurial people can really struggle with that. And then they end up never building anything great because they're too distracted all the time. So I think one is really locking in to say, this is like the one big, hairy, audacious goal that I'm trying to accomplish. And that's to say that there can be other things in your life, but focusing as much on that one goal. So even in my case, like I'm quickly, as quickly as I reasonably can, scaling down other things in my life in order to focus. So I've resigned from boards. I have ended most consulting engagements. that I was doing. I am continuing to scale down all of my kind of commitments in order to go all in in the search. And it's to say, the advice that I would have for people is it's not like a switch. Like focus, like it takes the time to sometimes disentangle yourself from things. But if you're going to go all in to try to build something, go all in. And over a period of a couple months or 6 months, resign from as many different kind of those things to create the space to really kind of focus and recognize that it's— there's a great book, Time Management for Mortals, and in it the author talks about the— one of the main things is about embracing the finitude of life that we can't do it all. And I think likewise recognizing like when you say yes to something, What are you saying like no to? So I'll share an example is that there was an organization I was on the board of for 3 years, learned a lot, but it also, this board could take up a lot of time and I saw that and that was fine in the past 'cause I had more flexibility. But now I was like, okay, by saying yes to this, what am I saying no to? I'm saying no to more outreach to business owners. And when push comes to shove, that outreach to business owners matters more. That is my top priority.

Yeah.

So I think the yes within the no is really important and it's a great question. Like, there's a lot of people I know that are incredible entrepreneurial people and they really do struggle with this like distraction. And I think that some of the people who are just like these amazing entrepreneurs are just like dogged and they think in terms of decades and they really just zoom into their companies and they build amazing things.

Yeah, that's great advice. The yes within the no, something for us all to write down if you are taking notes during this episode. Scott, I'm really curious. We've talked a little bit about some of the things you're doing to scale down parts of your life so that you can prepare yourself for this acquisition and the business that's going to be the thing you do for the rest of your life in theory, right? I'm a little curious, In terms of how you're deciding what kind of business you want to buy, did you have something in mind? Are you exploring a vast landscape?

I'm exploring a relatively kind of broad landscape, but I'll kind of give more context. I think the first one is that as a broad comment, if someone is considering entrepreneurship through acquisition, is there's 2 big factors that determine your search. A, the extent to which you focus on geography. And B, the extent to which you focus on specific kind of industry or type of business. If you are really specific on geography, it limits your ability to focus a lot on a specific industry. In the US, you have so many people that there can be people who do a search on a really specific kind of company if they're willing to move anywhere within the United States. But I think where people can trip up is that if you're really specific on industry and on geography, it's tough to transact. So for me, I am somewhat specific on industry and somewhat specific on geography. So what I'm looking for in terms of geography is any business in that is predominantly in Nova Scotia, New Brunswick, Prince Edward Island, and Ontario, which are 4 provinces in Canada combined. These provinces have a population of around 18, 19 million people, so decently sized, but not like huge. And, uh, so like half the size of California, it'd be like if you, if you were doing the search basically in all of South, you know, the, the southern part of California.

Los Angeles and, uh, yeah.

And San Diego, right? Like it's like, uh, and so that, that, so all to say then that means I can focus a little bit, but not that much. Uh, cause I'm also interested in sort of the $1 to $3.5 million EBITDA range. So businesses, not really tiny businesses, not. Quite large businesses. And then in terms of what I'm most interested in is these businesses that are B2B services businesses, often in a more traditional sector where there's a degree of like, there's recurring revenue or there's like a path to creating recurring revenue kind of within the business. And there's like a retiring kind of owner. And ideally most interested in businesses where the work is like required through like compliance or kind of like law insurance. And that is as a result of perhaps a little bit more AI proof than some like white collar work. And yeah, those are the types. So I'm looking at a really wide range of businesses and kind of firms. And reason I gave that sort of context at the beginning is I do think, you know, your, your, the, your answer to the geography question impacts your answer to the, to the businesses question. But when you're going into a search and before you start doing a search, I think it's really important to. be clear in terms of your answer of those 2 questions, because otherwise it's really hard to be strategic about how you're going out and approaching M&A advisors and business owners.

Yeah. Yeah.

I'll be interested to have you back on once you've created, built, bought a company and started building into whatever, you know, it's going to be the next iteration of that company. So just earmark that. For your own schedule. You have a quiz that people can take. Can you talk a little bit about what they'll find out by taking it?

Thanks, Anika. Yeah, I would love to do a follow-on episode once I have the second kind of major entrepreneurial experience of buying and then growing a company. Yeah, I have a short quiz that just takes a couple minutes to fill out and listeners can access it by going to scottstewart.com/quiz. That's scottstirrett.com/quiz. And the quiz gives you a score of 0 to 48 in terms of how comfortable you are with uncertainty today. And I think one of the first steps of learning to develop a better relationship with the unknown is learning to understand your current relationship with uncertainty. This quiz gives you that score. That score is not life-defining. Your score changes and evolves over time, but I think it is really critical in terms of helping you better understand and gain more self-awareness and ultimately help you put on, put you on the path to figure out where and how can you improve your relationship with uncertainty today.

Wonderful.

We could continue this conversation for hours, and I love it when I can say that when I'm speaking to somebody. Because it means that we are going to have further conversations and there's a lot left for the listener to learn from your book, from your quiz, from just reaching out to you. Scott, I'm also going to take this time to invite you onto my other podcast, Practical Pedagogy: The Art of Teaching for the Future of Work, because I think we'll have a little bit of a different discussion and be able to pick up some of the things that I didn't talk about here, which is, you know, for instance, talking about the AI conversation, what people need to be skilled for what that looks like for the youth who you've written this book for as well. So I really appreciated having this conversation about turning the unknown into an edge, thinking about how we can make those little risks, take those little risks every day so that we get more in tune with antifragility and with being in the unknown. So we will have, of course, the link to your book, to your Substack, and all those other ways to reach out to you and the quiz in the show notes. So Scott, I always ask if you have one final piece of advice and also do you have a quote, mantra, verse, poem, a family motto that continues to inspire you?

Well, first off, yeah, I'd love to be a guest on your other podcast as well, and thanks for the invite. I'd say the second piece, if there was one saying I would leave someone with, is that I think increasingly your ability to handle not knowing is more important than what you know.

That's a big one. That certainly gives us a lot to think about. So Scott, again, thank you so much for coming on Your Brand Amplified, and thank you to everybody who's listened to this episode or watched on your favorite platform. Share it with a friend and think about your own world and your own uncertainty and the uncertainty perhaps in your industry, what you can do to feel freer, In that world of uncertainty and what you can do to make changes in your business right now. Don't forget to leave us a rating or review on your favorite podcast listening platform. And if you want to learn more, check us out at yourbrandamplified.com.

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