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Scott Stirrett on Entrepreneurship Through Acquisition
Introduction
Hello again everyone. If you’re thinking about being an entrepreneur, what do you know about the game? Have you studied anything? Have you gotten any help or coaching? Well, I’ve got a guest today who’s been on a journey. He’s done quite a number of wonderful things, primarily in Canada, but no disqualify there. We we want to hear that story. There’s a lot of teaching there that will really help and enlighten, I think. My guest is Scott Stirrett. Scott, welcome to the show.
Thanks so much for having me on, Doug.
Meet the Guest: Building Venture for Canada
Yeah. Let’s talk about this venture you started in Canada a number of years ago. Tell us the whole story of that.
I grew up in Dartmouth, Nova Scotia, on the east coast of Canada, and when I turned 18, I moved to Washington, D.C., which was a huge culture shifts to move from a smaller community to the capital of the United States.
I stayed there for four years, and after Georgetown, I got a job to work at Goldman Sachs in New York City, where I worked for around a year. And right when I was starting at Goldman Sachs, I had this idea to, in essence, replicate an American model venture for America and take it to Canada.
And at the core of venture for America, recruits, trains and supports recent graduates to go work at startups across the US. Unfortunately, venture for America doesn’t really exist anymore, but it was a great initial inspiration for me.
And over 12 years, we scaled venture for Canada from just an initial idea to a national organization that has raised over $80 million of funding and supported over 10,000 Canadians to launch their careers. And of note, the initial fellowship program that we replicated from venture for America was the initial inspiration.
But today, venture for Canada does a ton of different things we do internships, project based learning for post-secondary students. We’re the largest trainer across Canada in entrepreneurship through acquisition education.
And one of my reflections from the experience is that what you start often evolves into something very different over a decade. And my experience of building venture for Canada, you know, was an amazing one. I learned so much along the way what to do and what to not to do. And that’s the 12 years of venture for Canada in a nutshell.
A Nonprofit Is Still a Business
Well, you know, clearly an entrepreneurial effort, albeit in a non-profit setting, but nonetheless, what I like to remind people, nonprofit organizations are businesses. You just have a different objective in terms of monetary gain or loss. And it’s still a business. It’s still an idea that has to be supported in some of the common standards, beliefs and practices that make businesses successful. Apply 100% to operating a successful nonprofit. So congratulations on that run.
Now, real quick, before we get into any of those other details. Scott, you were telling me in the green room, you’ve made a personal decision to make a little bit of a career pivot. You found yourself a replacement and exited that nonprofit. Now to yourself, become an entrepreneur through acquisition.
Yeah. I’m excited to dive into the next stage of my career, which is pursuing business buying. And in September 2026, I’ll start a full time search to acquire a Canadian business.
And I was attracted through ETA entrepreneurship, through acquisition for a couple of reasons. One is that I think that it’s important to reflect, as an entrepreneur, of are you somebody who is really great at kind of coming up with product market fit for a new idea that doesn’t exist, or are you better at kind of taking an existing business model and optimizing it?
And even if you look at my kind of track record with venture for Canada, it was taking a model from the US and adapting it to Canada and even the entrepreneurship through acquisition training we did. In many ways, it was taking inspiration from American models and applying it in Canada.
And as I reflected on what I wanted to do next, it was that I’m not interested in kind of finding product market fit for something that doesn’t exist.
I’m most interested in taking an existing business with an existing cash flow, existing reputations, existing employees, and grow that business and build on that business owners legacy. And as I spoke to 140 different people across Canada who’ve been involved with ETA, I increasingly reflected that ETA was the right fit for me in terms of my next step.
And that, you know, I want venture for Canada to be a part of my entrepreneurial journey, but I want to launch many things over the course of my career. And I think ETA is a great next step for me. And the funny thing I’d say too, is I think ETA is a great next step for people in my life stage.
I’m 35. I have the experience of operating a not for profit with 30 employees, multi-million dollar budget and leading people teams. I still have so much to learn, but I think I’m much more better prepared to go acquire business today than if I was like 27 or 28. That’s to say, you can still do it at 27, 28.
But I think doing ETA in your mid 30s is is a great step for that life stage too.
Why Entrepreneurship Through Acquisition (ETA) Works
Yeah. In to your point, you know, thinking about the difference between coming up with an idea and finding that product market fit versus identifying and already healthy cash flowing business that might be available for acquisition is is two very distinct strategy differences. And we call the latter, you know, ETA or entrepreneur through acquisition.
And if you can identify that business. And there’s a lot of press about baby boomers wanting to exit these businesses, and they’ve created great wealth opportunities in good, healthy operating businesses. But the practical reality is that business might have plateaued. It’s cash positive. There’s a healthy EBITDA that’s being generated on a regular basis. But the owner, quite frankly, is just tired. They don’t want to implement something new. They don’t want to innovate with maybe a new product line or an expanded market. So there’s opportunity on the vine.
Yeah, totally. And I think, you know, in a lot of businesses, there’s a lot of opportunity to continue to build on entrepreneur’s legacy and to create kind of new value.
I do think a lot of people pursuing ETA sometimes overestimate how easy it is to do value creation, that sometimes you think, oh, this person’s been operating this business for a long time, it’s easy to just come in and make all these changes and like double the EBITDA. And I think what I’ve heard from so many acquisition entrepreneurs is it’s often a lot more complicated than that.
But I think that there, you know, so many opportunities with ETA and it is now much better known and there’s much more support. But I still think that a lot more people should consider ETA as a career path, because it’s a great way, I think, to kind of get into entrepreneurship.
Yeah, I haven’t looked into the university level in Canada, but I know here in the US a number of universities with the bigger, more prominent business schools have actually started teaching ETA courses in their undergrad work and definitely in their graduate work. And they have, you know, adjunct programs as well to help expand the principle and ideas.
There are many pertinent and very vital steps in the acquisition journey, so I’d like to kind of highlight some of those. You again, you mentioned to me some of the things you’ve begun while we were in the green room, but through your venture for Canada experience, what were some of the early steps that you encouraged people to consider if they started going the ETA route?
The Early Steps: How to Start an ETA Journey
Yeah, a couple of points. I think the first is that it’s important to really familiarize yourself with the essentials of ETA at the beginning, and that can be in reading some of the most popular and well reviewed books on ETA. So like the Harvard Business School Guide to Buying a Small Business, I remember I read it in like 2020 during the beginning of kind of Covid, and it’s a great book as an initial primer just to learn the basics of ETA.
There’s also a great book by Yann Simon called Entrepreneurial Acquisitions that is more about not just about a variety of ways that you can kind of buy a business. It’s much more kind of in depth. It’s like a 500 page book, if I recall. But I really recommend that as well.
And then I’d say once you’ve done the reading, I think what’s really valuable is to then go out and start talking to people who’ve done, etc. I had the good fortune because of designing venture for Canada’s ETA Academy that I spoke to like 140 people across Canada. You know, dozens of people who bought businesses, brokers, lawyers, accountants.
And I think if you’re going to do ETA, it’s good to do some kind of equivalent, like you really want to go out and talk to a lot of people about their experiences, because that’s how you learn about what ETA and you can read the textbook, but really learning from others experiences is really important.
Then I’d say potentially it’s valuable to take a course on ETA. In the US you have like acquisition lab in venture. In Canada, you have entrepreneurship, the acquisition academy. But taking some kind of formal course I think can be really valuable just to kind of help get in there.
And then I’d say if you’re like, hey, now I really want to keep on considering ETA as a career path. I would say one of the things you want to do is figure out what is the kind of ETA that is the right step for you. Are you planning to launch a search fund, or are you planning to launch a self-funded search?
Most people who do ETA are not search funds. They’re self-funded searchers. So you want to have a fair amount of your own capital, I think available if you’re going to really seriously consider ETA. And I think one of the things that you want to do is build relationships with investors or people who could kind of work with you on deals.
And then once you have that set up, what I would recommend is beginning to think about like, what is your investment thesis? As one private equity investor recently said to me, like the best PE firms or acquisition entrepreneurs have some kind of investment thesis, I think that they’re not just saying, I’m looking to buy like a good business, and they have an idea of how they’re going to create value.
And that’s to say you can still be pretty flexible in the context of your search, but having some sense of what your general direction of what you’re looking for in terms of EBITDA, revenue sector. And then I’d say once you reach to that point, is building relationships with your advisor team. So securing a lawyer that you’re going to work with, securing an accountant you can support with quality of earnings and then potentially launching a website that sellers can kind of go to, to find you.
And then I’d say dive in to do a full time search. That final thing I would say is that I think one of the most important things in doing acquisition entrepreneurship to be really successful likely is you have to treat it as a full time job in terms of buying a business.
So I think building in time to go full time search for a business for like six months to two plus years is really kind of important, I think, to be more successful because it’s hard to like. One of the hardest things about ETA is finding a good business. It is a full time job to often find and acquire and ultimately operate a successful business. So that is a very detailed answer to your question, but it goes into all the steps.
Why Asking Price Often Misses the Mark
And I agree wholeheartedly with everything you’ve said and what you’ll find. Speaking to those who might be listening and intrigued by this is that what might be listed for sale is only the rudimentary beginning. Because often what does happen, at least here in the United States, it happens frequently. Brokers agree to take on a listing without doing their own due diligence on the deal, and really setting a marketable price expectation for the seller.
And I’ve seen this happen where a seller literally is out playing golf with a bunch of his industry buddies, and he says, I think I’m going to sell my business. And they’ll have a chit chat around the 18th green and they’ll say, oh, you know, you ought to get 7 million for that business. Well, that becomes his magic number. And there may be no valid rationalization or justification for a price that high.
And it will be easy for them to find a broker to list at that number, but it’ll sit there in the listing for sometimes several years, not getting any serious takers, because serious buyers on first blush will realize that 7 million is an invalid number, and even if they try to go lower on their bid, they’re going to be rejected for no good reason. And it just goes on and on.
So often, what I encourage clients to consider is find a broker who will explain their process to you on how they accept listings and if they’re not doing the work with a seller. It’s not a lot different from good real estate brokers who will work with a seller to optimize the offering price for the property they’re trying to sell. And if all the comparables in your neighborhood say your property is only worth $200 a square foot, you can’t ask for $300 a square foot because you’re it’s not going to appraise properly and people aren’t going to go, you know, at a 50% premium just because you think your house is pretty.
The Best Deals Are Sold Off Market
Yeah, that what you said rings true in Canada too. I think a lot of the times the most of the highest quality deals are not publicly listed for a variety of reasons, partially because there’s a lot of challenges for business owners to publicly list their business in terms of spooking employees or customers clients.
And as a result, the best businesses tend to be sold off market, which is why, you know, brokers have off market deals. There’s proprietary search where people are just cold emailing business owners. And that’s a common way that a lot of searchers successfully acquire businesses.
I’ll just say is, I think building relationships with brokers are really important, and brokers have access to a lot of deal flow, but a lot of the deal flow, the highest quality deal flow that brokers have is not necessarily transparently listed on any kind of website. It is shopped around, but it’s shopped around privately amongst their contacts.
Yeah. Totally agree. And that same thing happens here. I recall a story of a young man who had made the commitment to turn his career toward ETA and was driving by a property, a business, in his community.
Just the signage intrigued him. He pulled in to get information about the owner, and owner was not on site, and he didn’t tell anybody what he was asking about. He just wanted to know who the owner was. He did the research, found the owner’s home, went up and literally knocked on the door and said, hi, I’m so-and-so. I’m a private investor. I drove by your business. I’m interested. Is there any chance you might be considering selling it?
And the guy said, wow, this is spooky. Yes, as a matter of fact, my wife and I just started talking about it and said, you seem like a nice guy. Come on in and let’s talk. And they began the discussion, and next thing you know, there was a letter of intent exchanged and totally private deal. Never got anywhere close to listing. And it became exactly everything this person wanted in their investment thesis.
It’s a great story. And it was also an example of where non-traditional engagement with sellers can often be such a differentiator, like just going through the traditional routes. That’s what everyone’s doing.
So I think having that personal touch and building relationships ultimately with people is something that is so important. And that’s a great piece of advice that I will definitely keep top of mind as I consider a search. While as I consider the strategies in which I engage with sellers as part of my search.
Do You Want to Buy a Business, or Need To?
Yeah, and I want to hit on another point you made about really committing this as a full time job as clients have approached me over the years expressing an interest in going this route. I ask him a fundamental question do you want to buy a business or do you need to buy a business? And those are two significantly different ideas. If you really think about them.
You know, the idea of wanting to buy it almost suggests this is a side hustle. If it works, great, if it doesn’t, that’s okay too. But if you really need to buy a business because you have jumped out of the plane without the parachute, and you are now all in for finding this business. To replace your income, you need to buy a business. You need to make that happen.
And yes, you want to do it too, but you really now need to. You can’t let it go on indefinitely. You have to be intentional about doing the work and managing it accordingly.
Also really great advice and I think in ETA there can be a lot of like tire kickers who just like look at online postings and dream about one day buying a business. But very few, if almost none of those people end up actually buying a business.
It requires, to your point, like a ton of dedication and to buy, especially a good business. And you really have to put, you know, if you’re going to buy a business, you’re putting a huge amount of risk as a buyer, often a personal guarantee, a lot of your net worth, if not the majority of it into this deal. So you have to treat it like it is the deal of your life, because it is the deal of your life.
And that means treating it with the level of focus that’s really important. You know, as I think about doing the search, one of the things I’m doing is winding down a lot of my other, most of my other commitments, so that in the the sort of parlance of the day, I’m locking in into the search and that I don’t have that many other distractions going on for me while doing it.
Because I think it applies broadly to entrepreneurship. Like when I look at some of the most successful entrepreneurs, when they’re first starting, they cut out a lot of things from their life to go buy this business. When I think about my startup venture for Canada, I cut out a lot.
That’s not to say everything, like there will be some little side things that I will continue doing. Even once I began the search. But I think my mindset is to try to cut like 60 to 70% of the discretionary things I do to go be as focused as possible in terms of buying a business. And likewise, I think when I once I actually buy a business and operate it, I’ll need to be as focused, if not even more, in the first couple of years.
And I think that focus is often underappreciated. I find a lot of entrepreneurial people can maybe have a tendency to like bright, shiny objects and maybe not be as focused. But if there’s a piece of advice I would have for people who are entrepreneurs, having done it once with venture for Canada now, doing it a second time is that I think focus is like a really superpower that can differentiate successful entrepreneurs from unsuccessful ones.
Bring Your Leadership Skills — and an Owner’s Mindset
I totally agree with you. And I had another client one time that made a declaration. He said, you know what’s ironic here? I’ve been a senior executive in the corporate world for some time, and I’m feeling the need to go this direction and make a career shift. He said, why shouldn’t I apply all of my management leadership skills that I leveraged in my corporate role? Why wouldn’t I do that for my own company? As I’m searching to buy a business, to set up the mindset that I already have a company?
And by the way, you know, at least down here, we encourage people in the early going to go ahead and set up an LLC to frame their business, and you don’t have to know the name of the business you’re going to buy. You can bolt those together pretty easily with the right attorney. But go ahead and set up that LLC and, you know, book some of your expenses for your search effort and your coaching and advisory work.
Go ahead and run it through the company account. You know, fund it with personal money, but run it through the company account and begin the journey. You know, go ahead and keep that going and develop that mindset that this is my company, this is my new company. This is what I’m doing.
Yeah. And that’s pretty common in Canada too, because our tax system is different. Asset purchases are quite unusual in Canada, but share purchases are very common. And people will often incorporate an entity around buying those shares in the company that they do choose to buy.
And I actually just came up with the name of the company that I will incorporate as the holding company for shares and yeah it’s important. I think as searchers, it’s also good to think about the branding of like what is your Holdco kind of name going to be? What’s the website? There’s a lot of these searcher names that are really generic that could just sound like anything.
And one of the things I really tried to think about is what’s something like a unique name? I’m not going to share it on this podcast yet just because it’s not.
Yeah, I get it.
I don’t have it launched yet, but I do think that like anything, thinking about the branding of this business, what’s the branding of your search? What’s something that is unique, differentiated, specific to you is really important.
And to your point, treat the search like a full time job because it is a full time job. And it’s really hard when you first are starting anything. Like, I’m having a lot of flashbacks now to the early days of venture for Canada 12 years ago, because I was in the same situation. Well, similar. I now have a lot more experience under my belt.
But you know, I’m dealing with the skepticism of some people of like, well, why would you want to buy a generator maintenance company when you’ve done this not for profit or, you know, the loneliness of doing a search as well? And I’ll say is that I think discipline is so important, particularly when you’re doing what can be a lonely kind of journey and as much as possible, creating structure that supports discipline is really important in any kind of entrepreneurial journey.
Protecting the Seller’s People and Legacy
I totally agree. And you know, the other thing, when you do begin the search and start making contact with potential sellers is the opportunity to represent yourself as a true and legitimate private investor, you know, to, in the minds of a lot of owners that are thinking about selling, when they hear about private equity or venture capital, they immediately think about dismantling and abandoning people.
And it on one hand, it’s unfair to cast everybody in that sector in that way, but it’s an undeniable reality that most private owners think of it that way. So their first question is, what are you going to do to my people? And what are you going to do to my customers? Because they still, you know, it’s the child they birthed and raised up. And they have an affinity for the people that have been loyal to them, both employees and customers. And they are very, very sensitive to adversely impacting those folks on their exit.
Totally. And that’s, you know, one of the things I’m looking at in buying a business is to continue that business owners legacy. It’s not about doing kind of a pump and dump and run a business for a couple of years and do some financial engineering and then sell it. It’s to run it for the next part of my career.
So that could be 20 or 30 years of running and owning this kind of business. And that’s very different than a lot of other kind of financial investors who are just kind of looking for kind of a quick return.
And I’d say one of the things I’m trying to differentiate myself as a searcher is that I built like a community based organization venture for Canada. I know what it means about giving back to community, and partly what attracts me to ETA is owning and operating a business that contributes to communities, that contributes to my country.
And yeah, and that and to sort of view business ownership as a way around wealth creation, but also as a way to help provide people meaningful employment and quality of life and a good workplace. And that’s one of the things I think, that really attracts me to entrepreneurship. And to your point, I think can be a big differentiator between a private investor and a large investor.
Behind the Scenes: The Pivot Points of a Founder
Yeah. I want to shift gears a minute, Scott, if I may, I want to go back to your venture for Canada creation and growth over those years that you first created and then grew that organization for you as the founder. What do you see as a couple of key pivot points, in your own view of who and what you were supposed to be for the benefit of that company?
There were a couple of big pivots that happened. I’d say one was that in early 2018, adventure for Canada received a lot of funding from the government of Ontario and the Government of Canada. And we really scaled our kind of team from like three people to 15 people.
We launched our first program separate from our original fellowship program, and that was really the path to venture for Canada as this organization quite different from what the initial venture for America idea was. So I’d say that that was one pivot point of not necessarily just being beholden to the initial idea, but to let venture for Canada continue to grow and develop.
Let’s say a second major pivot point was embracing the ETA training part of venture for Canada, which today is a very significant part of Venture Canada’s work. There was even a lot of internal resistance, because a lot of our programs before were about connecting young people to work at startups.
So a lot of people sometimes within the org were like, this is random, why are we doing business, buying education? This is completely different. And it took a lot of change management and persistence. And I think to some extent like longer term vision. But today ETA is a huge part of the GFC and I think the organization is a lot stronger because of it.
And I’d say a third pivotal movement was me deciding that it was time for me to move on. After doing much for Canada for 12 years, I could just feel my heart wasn’t in it. In the same way I was feeling the desire to do something new. I knew that if I had spent another ten years doing venture for Canada, I would have regret that I wanted to do for profit entrepreneurship and that if I never did that, I would always look back with regret upon my life.
And ultimately that I think myself and venture for Canada will be more successful if ultimately we transition to getting a new CEO in place. And Doug, that was a really tough decision. Like when you built something since you were like 22 and your identity becomes really a part of it. Like giving that up optionally is not an easy thing to do at all.
And I had an option to join the board. I said no, I want the new person to run and to not have me kind of trying to control things from behind the scenes. I have a great relationship with the new CEO. I talked to him a lot, but he is the CEO and I’m not running venture for Canada.
And you know, one of the that was I think a pivotal point. I think hopefully for Venture Canada to be more successful long term. And also I think for me to be more impactful so that I can pursue ETA and some of my other dreams and aspirations. But it was that was a I mean, we can talk more on that, but choosing to give up something that you founded and then stepping away when you’re used to being the CEO to then starting from scratch where you have no team and you’re doing it all over again.
Boy, it has not been easy. Like, it’s a tough psychological kind of thing. And sometimes I feel for people who are like, let go or things because like that would be even more like I, I made the choice to do it, but it’s still not easy to kind of give that up to then say, I’m going to start all over again and start this lonely journey of acquiring a business.
Knowing When Your Time Is Up
Yeah. Well, you highlighted a couple of the very things I was thinking about, and the point being that it’s so vitally important for owner founders to have their own awareness and willingness to make those mental changes that might be required for the better of the organization, because the thing you create, if you’re in that founder mode, may grow into a life of its own.
And you have to periodically ask the question, am I the one that still needs to be at the tip of this mountain and being willing to make those calls, whether it’s a total exit and extraction of yourself, or more of a delegation and relenting of power to others to run the business.
I tell the story. I had an entrepreneur on my show a couple of years ago who described a three way partnership he had with two others, and they built a small restaurant chain in California and had great success and finally got to a place. They were having a meeting one day and said, I think we need to hire a CEO. I don’t want to be CEO and somebody else. The other two partners said, I agree, I don’t want to be CEO. You know, let’s let’s go find one.
We will pivot to be more the visionary holders of the truth and more oriented toward investing in the business rather than running the business. And that’s what they did. And the guy they found was a force in the restaurant world, grew the chain to 100 locations, you know. So they had a nice payday on the exit, much more than they ever would have had on their own.
It’s such an important point. Like as a CEO, it’s important to always ask the question, am I the right person to still be in the driver’s seat. Yeah. I realized at a certain point I wasn’t for adventure for Canada.
And I think when you get into a lot of, like, corporate messes is when you oversee overstays at a time, there’s very few CEOs that are like, should stay. I think in a role beyond like 12 or 15 years. Lots of data backs this up that there’s often diminishing returns at like the 10 or 12 year mark for a lot of CEOs.
And you even see this sometimes in people’s like corporate their impact like that they a lot of CEOs peak at like year six seven, eight. And then there can be sort of diminishing returns post kind of year 10, 11. And it’s healthy for an organization for there to be renewal and a change in leadership. And it’s like anything, if you do any job too long, you become kind of stale over time.
That being said, there’s some great leaders who can be 20 years as a CEO, 30 years as a CEO. But I do think that in most organizations, it’s healthy for there to be kind of turnover at that approximately kind of ten year ish kind of mark.
And yeah, I mean, it’s important in so many different kinds of settings. It’s important for families or family owned businesses to sometimes ask the question like, should a family member be running this? Or should there be a outside person who is running? I know that’s one of the things that family businesses really kind of grapple with.
And it’s really hard to sort of remove yourself and to ask objectively what is in the best interest of this organization. But that’s what I think you have to do. You have to try to remove yourself from it and say, like, who is the actual best person to do this job anymore? And if it’s not you, it’s time to, you know, get out of the way.
And to your point, it’s not binary. Sometimes it’s not about completely exiting. Sometimes it’s about becoming an advisor to the new CEO or chairman of the board. There’s a lot of different paths, but knowing when your time is up is an important skill that I think a lot of people often don’t appreciate.
Closing Thoughts
Well, speaking of, time is up. I think this is a good stopping point for us. Scott, thank you so much for sharing this. I wish you nothing but the best in your journey with ETA. I’m going to make a mental note to check back with you toward the end of the year, once you start your search in September. Hope all things go very well for you. Really appreciate it.
Thanks so much, Doug.
All right, folks, I think that’s going to wrap it up. I hope you found this helpful. We do have a video version of this which will be appearing on YouTube, a channel by the same name. Leadership powered by common sense. Please join the channel. Drop us a note, leave us a comment. Let us know if you’ve got any ideas for things we should be talking about next. But for now, I’m going to say goodbye. Go out there and make it a great day.
Meet Our Guest
Scott Stirrett is a Canadian entrepreneur, author, and social impact leader whose mission is to help people reach their full potential. He is the Founder of Venture for Canada (VFC), a national charity that has supported over 10,000 young professionals since its launch in 2013 and raised over $80 million in funding.
Before founding VFC, Scott worked at Goldman Sachs in New York City.. He has been recognized as a Telus LGBTQ Innovator of the Year, an Action Canada Fellow, a Globe and Mail Changemaker, and an Ashoka Fellow, among other honours.
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