If You Can't Go to Barbados, You Don't Have a Business
Brad recently had a guest appearance on Jeremy Rivera’s “Unscripted Podcast”. Below is a shortened transcript.
JEREMY RIVERA
Hello, I’m Jeremy Rivera, your unscripted podcast host. I’m here with Brad Poulos, who’s going to introduce himself. Give us a taste of his expertise and what he’s been working on recently.
BRAD POULOS
Sure. Hi. I’m an educator and a consultant in the small business space. I teach at Toronto Metropolitan University in the entrepreneurship department. I’ve been doing that for about fifteen years. I also do consulting to small businesses in Canada and the United States.
How Entrepreneurship Education Has Evolved
JEREMY RIVERA
Over that course of your career, what’s in the curriculum has just gone the way of the dodo?
BRAD POULOS
Probably the way we do business planning. If I go back to maybe just a little bit before I started teaching, when I launched a satellite-based internet product for a big company here in Canada, we wrote a business plan — it was this thick, full of spreadsheets, lots of numbers that were complete fiction, of course. I managed to raise two million dollars from the board of Bell Canada, who owned our company, so we had the same board of directors. I presented this business plan to them and they gave me the two million dollars right in the meeting. And up until that point I had never spoken to a prospective customer. Nowadays, of course, we practice lean startup and we put sales ahead of anything.
We still do business planning, but we do it in a much different way. The other thing is that entrepreneurship is just so much easier now. In that exact same project, we wanted to be able to take credit cards from individuals. In order to do so, we had to write code that interfaced with the bank. And then the bank had to approve our code. Now it’s a checkbox on Shopify. That’s a double-edged sword, of course, because entrepreneurship is a lot easier; it’s easier for me, but it’s also easier for you. It’s a much more crowded space now.
JEREMY RIVERA
So you’re trading off competition versus capital requirements. You could previously only compete if you could find that initial investment to overcome that hurdle — it reminds me of the tattoo industry where the government imposed requirements just to raise the capital cost. So we’ve traded that type of road blockage on digital infrastructure. Is it better to have more lean competitors or was it better when you had just five 800-pound gorillas running around?
BRAD POULOS
Better’s a value judgment, so I’m a little bit hesitant to make it, but I’ll do it anyway. I’d say it’s better. In the sense that it’s more democratic. It’s more available to you and to me and anybody else. In the old days, it mattered a lot more who you knew, and now it’s probably more important about what you know.
Staying in Your Niche vs. the Omni-Tool Temptation
JEREMY RIVERA
The pace of technology is improving baseline access, and we’re seeing more infrastructure marketed to small businesses. Every challenge that large digital marketing teams were facing now seems to have a SaaS offering a solution at every corner. How does that work in terms of standing out, especially when a big player says, “Don’t do that, just use my AI tool to code everything”?
BRAD POULOS
It’s tough. There’s becoming a proliferation — I’m guilty of it too. The number of different things I’m now subscribing to is starting to get silly. I think eventually there’ll be some pushback, and probably a move more toward those omni sort of tools.
JEREMY RIVERA
It’s challenging because I used to work in a large SaaS company called Raven Tools within the SEO industry. Once you achieve your core mission — for them, agency reporting was the primary piece — then there’s this pressure of “yes and.” Once you start down that path of not specializing, the expertise starts to diversify. If you add social media management and PPC management, then the specialization and the features you can release are spread across multiple types of tools. You’re right that there’s a tendency toward platformization, but it also has that wraparound effect: it does more, so now you have to support more, and you haven’t updated your original core reason that they bought the thing in six months.
BRAD POULOS
I’m a firm believer in you dance with the one that brung you. You’ve gotta make sure that you never lose focus on what your original mission was and don’t abuse the product that got you there. The other thing is that when you start to expand, you’re now competing with much larger players. They’re probably in a much better position to compete in those broader markets than you are, and perhaps staying in your niche and doubling down on that is the better strategy.
Digital Marketing for Local Service Businesses
JEREMY RIVERA
I’m curious what your advice is right now for SMBs in manual services — tree trimming like McAllister Tree Service, installing concrete walls in Florida, doing home repair in Tennessee. If you’re geo-based and doing services, what does that look like from your perspective?
BRAD POULOS
I actually love those kinds of businesses. They’re never gonna go away. A lot of digital tools may come and go, but a tree trimming service will virtually always be here. The thing that’s changed over the past ten years is that the really good players are both good at executing their trade and good at executing digital marketing.
It’s becoming necessary to stand above the crowd and to get the leads first. I’m a member of a group that has a wedding photographer in it, and that wedding photographer is spending two hundred dollars a day on Facebook ads. So you better be good at it when you’re spending six thousand dollars a month.
B2B Marketing in a Digital-First World
JEREMY RIVERA
What’s the state of play in B2B as technology increases? What’s the play for, say, an oxygen monitor company providing monitoring for ice cream shops or chemical plants? If you’re selling business to business, how has that changed?
BRAD POULOS
Targeting them is different now. If you’re in a category that’s existed for a while and people know what they want, search marketing is an option for you. But if you’re selling something that people don’t know about, you’re really looking at other forms of marketing, and it can be tough, especially with B2B. B2C is one thing because you can find people on TikTok, Facebook, Instagram. A little more difficult if you take search out of the picture with B2B — you’re looking mostly at LinkedIn, and it’s a lot harder to target people there.
One of the reasons is that people are a little more mercenary about the time they spend on LinkedIn. A serious business person might quickly browse LinkedIn in the morning over coffee, but then they go home and endlessly scroll Instagram. That’s one of the implications for B2B that’s definitely different from the past. We’ve also lost things like the trade magazine, which I used extensively twenty years ago — it’s not even important anymore.
JEREMY RIVERA
The nature of shotgun saturation attempts of remarketing programs — you visited something and it shows on totally unrelated sites until you go back and buy. But if you’re showing me stuff on Instagram that’s related to what I do for work, it’s probably not nearly as effective as it would be in a B2C niche.
The Best Marketing Channels for Early-Stage Entrepreneurs
JEREMY RIVERA
Talk about some of the different channels and the challenges you’d couch in those recommendations for entrepreneurs to understand their marketing opportunities.
BRAD POULOS
We always start with person to person, and that’s obviously the most rich. If you can do it efficiently, that’s wonderful — go where they are, meaning industry events, trade expositions, that kind of thing. For very early customer development and customer discovery, whether it’s virtual or physically in person, nothing beats that. That’s where you get the greatest insight.
Beyond that, it’s using different forums on the popular social media sites, as well as Reddit. Reddit can be very helpful because it’s very subject-oriented and one of the last bastions that hasn’t been totally ruined with ads and garbage.
JEREMY RIVERA
Reddit’s a fascinating microcosm. On the one hand, it has a very strong self-protective nature — you’re a shill, this is spam, we don’t want this. But sixty percent of the time it works every time — you’ll see very obvious commercial enterprises that everybody loves and blasts to the moon. There’s like a lottery effect of being able to sell on Reddit, but very rarely. Just enough to keep the appetite alive.
BRAD POULOS
I wasn’t thinking so much about selling as learning about your customer and the problems that they have, which is the work you’re doing during customer discovery.
JEREMY RIVERA
That’s fair. So if you use Reddit more as a way to understand how people are discussing the current ways that a problem is being solved — because at the end of the day, if you’re an entrepreneur, the question you should be asking is: how do I display empathy to the market? That empathy, that understanding of the pain, is what you’re after. It’s like white blood cells in a body — there’s a pain point and businesses coagulate, they form around that pain point to try to solve it.
BRAD POULOS
Yeah, that’s a great metaphor. I’m gonna probably steal that one.
Entrepreneurship Education in a Post-Textbook World
JEREMY RIVERA
Coming from the educator side, in SEO and digital marketing it’s very tough to have a curriculum because so much changes. Any textbook written four years ago is ridiculously outdated. Is higher-ed entrepreneurship post-textbook at this point?
BRAD POULOS
Absolutely post-textbook across most of the courses I teach, for the reasons you pointed out. As educators, we can’t keep up ourselves, so we use subject matter experts — we bring people in. SEO is a great example: I have one of our grads, he graduated about ten years ago and he’s a sought-after SEO marketing specialist, and every year I bring him in and every year I hear new things. Now some things don’t change — physics probably doesn’t change a lot — but digital marketing? Absolutely post-textbook. In fact, there’s one course where I’m mandated to use a textbook prescribed by the curriculum committee, and none of the other courses I teach even have one.
The Psychology of Entrepreneurship
JEREMY RIVERA
You have to wear so many hats to be successful. What do you teach about psychology and mentality? What do you teach on the human side of being that person wearing all those hats?
BRAD POULOS
There are a handful of characteristics of successful entrepreneurs at any level. I’ll preface this by saying that the household names had some luck as well — that’s what differentiates the billionaires from the millionaires.
For any entrepreneur, having a high internal locus of control is very important. Believing that you are the driver of the bus that is your life — they’re not passengers in their life, they’re very much driving it. There’s actually a book we use in our program about effectual thinking, and one of the five themes is the pilot in the plane — you’re in charge of where your life is going.
As it relates to life balance, I have to admit we don’t spend a lot of time on that. You’ve got me thinking maybe we ought to, because I’ve certainly seen what you’re talking about. Almost all of the household name entrepreneurs are on at least their second marriage.
Do You Have a Business or Do You Own Your Job?
JEREMY RIVERA
That discussion revolved around one core concept: structuring your business isn’t successful until you’ve structured it where you are not the primary and singular activator of revenue. If you are the singular junction for generating revenue, then you don’t have a business — you have a consultancy. You’ve just hired yourself.
BRAD POULOS
One of the things I tell my students all the time is: if you can’t go to Barbados and sit on the beach and you’re making money, you do not have a business. You own your job. Which is better than having a job.
JEREMY RIVERA
That’s it. I’ve fluctuated back and forth over my twenty-year career in SEO — freelance consultant, in-house with SaaS, at an agency, subcontracting, spinning up my own projects, affiliate revenue, referral revenue. There were moments where I realized: I am paying myself so poorly as an employer. I’m putting in so much and getting so little out because I’m the only person working in this shop.
Delegating Outcomes: The “Most Problems Solve Themselves” Philosophy
BRAD POULOS
You’re sort of segueing into one of the books I recently released: Most Problems Solve Themselves. It’s a book of fifty-two articles — I chose what I thought was one of the more provocative titles to put on the cover. What that article is really about is two things.
One is: when I was really busy working on a project in my corporate life, if somebody who wasn’t my boss or a direct report asked me for something, I made them ask at least twice. What I found was that a lot of times I never got the second email — I just considered it a problem that solved itself.
But the other way I look at it is about empowering employees. I used to travel a lot when I had my own businesses — they spanned all of the Americas.
When somebody would come to me with a problem, I’d say:
“Last week I was in Vancouver — what would you have done?”
And they’d say, “Well, I would do this.”
And I’d go,
“I think we should do that.
” What I was doing was putting the decision back on them, empowering them, showing them they have the autonomy and the intellect to make good decisions. When you let go like that, it frees up your time and also helps develop really good employees. Good employees want some autonomy — if they don’t have it, they’re going to leave.
JEREMY RIVERA
I think you could state it as: don’t delegate tasks, delegate outcomes.
BRAD POULOS
Great way to say it.
JEREMY RIVERA
Because LLMs and AI tools right now are definitely B or sometimes C-level players. I can recall when I was managing a team of twelve — there are people who will do exactly what it is that you say, specifically how you say it, and nothing more, without thought of the consequence or what comes next.
“Turn the pipe seven times. Done.”
Well, I wanted you to turn the pipe seven times so that this nuclear bomb didn’t go off, but this next thing over here also needs to be turned.
“Beyond my pay grade,” they’d say.
BRAD POULOS
Right — not every pipe is exactly seven times. Some of them need seven and a half turns. We kinda want people who can figure that out on their own.
Organic vs. Mechanistic Organizations: Right People, Right Seats
JEREMY RIVERA
As an entrepreneur, is there sometimes a need for B players? At the end of the day, sometimes you just need somebody to turn a wrench at a particular time and place. Is it really about having that awareness that there are different types of employees?
BRAD POULOS
There’s probably now sixty or seventy-year-old theory about how you organize your company. The two extremes are mechanistic and organic. In an organic organization, you want people who show a lot of proactivity — you can basically give an outcome to them and they’ll figure out the tasks.
Lots of communication going in every direction.
A mechanistic organization is more like the military, where communication is up and over and down, decision-making is pushed up not down, and we don’t encourage thinking out of the box.
A good example is a McDonald’s franchise. You don’t really wanna hire super entrepreneurial people to work in the back — they’re going to want to tell you a better way to cook the fries.
The fries have been figured out. In that organization you want consistency, not just in your own operation, but between your location in Toronto and the one in Shanghai. You can actually have portions of your organization that you run mechanistically and others more organically.
Knowing which ones are which and then being able to find the right values in people to get them in the right seats on that bus — that’s what makes a really good leader.
JEREMY RIVERA
Agree or disagree: is scaling truly the enemy of creativity in business?
BRAD POULOS
In many ways, yes. That’s why big companies purchase a lot of their innovation. Companies like Procter and Gamble are buying creative people because they don’t have them inside the organization.
The things that come with getting big — having to create some level of bureaucracy, otherwise you’ve got pandemonium — can tend to stifle creativity. It’s an inevitable outcome. You can probably mitigate it somewhat — Google used to have that ten percent of your time toward a Skunkworks project — but it’s tough, there’s no question about it.
The Profit Motive, Bootstrapping, and Smarter Funding Paths
JEREMY RIVERA
This is probably controversial, but do you think one of the fundamental problems with business is that when companies are chartered, there isn’t a thought as to how the thing ends — and so you end up with the singular driving line of profit?
BRAD POULOS
Especially once you bring in outside investors. If you can manage to stay bootstrapped and founder-owned, or at least family-owned for some period, you can probably get around that profit-only motivation.
But even in a family business, once it gets to a certain size, you end up with family members who are owners but don’t work in the business — they’re just demanding their quarterly dividend check. It’s certainly true of the public markets.
The profit above all else motive doesn’t serve society particularly well. It serves investors well. It doesn’t serve employees well. Read more about Brad’s perspective on bootstrapping strategy on his post Bootstrapping: Building Your Business on Your Terms.
JEREMY RIVERA
In what way should a SaaS consider transitioning off of bootstrapping? I know that lure — hey, make a deck, approach some VC folk, get funding, get runway. But it’s a carrot on a stick held by somebody very willing to beat you with the stick. Once you give them that power, they hold the stick and they direct you.
BRAD POULOS
Maybe less modest growth but still scaling through using an angel investor, and you search one out that has a similar mindset to yourself. A lot of angels are investing not just for a financial incentive but also to give back — certainly more than the VC community. That’s maybe one way.
JEREMY RIVERA
Good advice — knowing there are different mechanisms for funding. I was at a backyard barbecue and talking to a guy in the restaurant industry who said, “Man, I’d be free if I could just get a million dollars.” My mind was like: there are so many different ways to get funding, and do you actually need a million dollars? Probably not. It doesn’t take a million dollars anymore to launch your stuff.
BRAD POULOS
You could probably test the concept in a much more modest fashion for sure. Maybe it’s not exactly the space you’d like, maybe it’s not as large as you want, but you can test your concept. It’s only a pretty elaborate restaurant or bar club that needs a million bucks to get off the ground.
The Controversial Take: An Enfeebled Generation?
JEREMY RIVERA
What’s your most controversial take at the moment in the entrepreneurial world?
BRAD POULOS
A lot of people might not like this, but: the generation of students we’ve created post-pandemic is nowhere near as good as previous generations at solving problems. I blame the parents primarily. I also blame the public school system, but the combination of those two has produced an enfeebled generation. It’s tragic. In our department we try to beat it out of them, but it’s tough love — and the world is tough. Once you get out of university, accommodations go away, and you’re going to be expected to solve problems or you’re gonna have to find something else to do.
JEREMY RIVERA
As a millennial, there was so much scorn handed down to my generation — “suck it up, buttercup” type rhetoric. I questioned that until I volunteered for our homeschool co-op to teach a science fiction club.
Challenging them to take the next step each time, it took a lot of effort to engage that creativity. From my anecdotal experience, it is striking. Is that reversible? Have we programmed this in with social media?
BRAD POULOS
I think there are a few factors. The pandemic didn’t help — locking kids down for a few years had an impact. But mostly I think it’s over-parenting. I’m from the generation where we had two rules: be home before the street lights come on, and don’t come home in a police car. We had no devices, so we were left to our own devices. We were out in the forests building forts.
In each subsequent generation we over-parent. The idea of a play date — can’t kids figure out how to play themselves?
And what we see in universities is that it’s not even helicopter parenting anymore — it’s bulldozer parenting. They bulldoze every problem out of the way of their kids, so by the time they get to me, they can’t solve a problem. They think rules are a list of things you’re allowed to do, as opposed to a list of the things you’re not allowed to do.
There’s a book by Jonathan Haidt — The Coddling of the American Mind — where one of the major themes is this notion that we treat children as fragile, when actually they are anti-fragile.
Like this cup — if I drop this cup, it breaks. If you drop a kid metaphorically, it gets stronger. You don’t break them by exercising them. You make them stronger.
Brad’s Books, Products, and Where to Find Him
JEREMY RIVERA
Transitioning toward the end, I’d love to hear about the projects you’ve been working on — books, speaking engagements. Who are you hoping to speak to?
BRAD POULOS
My primary market is small business owners that have built the business — somewhere in the roughly five to fifty million dollar range, a couple dozen employees. I recently released a digital product at confidentoperator.com called The Operator’s Cadence, which helps small business owners who have grown their business without a lot of structure find themselves in a more chaotic situation than expected.
It helps take away some of that chaos through a planning cadence that works right down from a ten-year vision to a daily planning cadence.
I also mentor at several Ontario-based incubators — most of that is for free, just giving back. And I’ve got three books on Amazon: Most Problems Solve Themselves, The Small Business Operator’s Manual, and earlier this year I released with a co-author From Pitch to Payoff, which is about venture finance aimed at the startup operator — a space where there really wasn’t a book that covered it.
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Key Takeaways
Lean startup has replaced the traditional thick business plan — customer validation before capital was fictional on paper but is now table stakes for every entrepreneur.
Local service businesses won’t be disrupted out of existence, but to win leads you must master digital marketing just as much as your trade. Spending $6,000 a month on Facebook ads without skill is a fast path to loss.
B2B marketing without search intent is hard. LinkedIn attention is limited and mercenary; the trade magazine is dead. Prospecting tools that worked in person or in print haven’t found clean digital replacements.
You don’t have a business until you can go to Barbados and still make money. The difference between owning your job and owning a business is whether outcomes can be delegated — not just tasks.
Organic vs. mechanistic organization structure isn’t about headcount — it’s about knowing which parts of your operation need autonomous A-players and which parts genuinely need consistent task-followers, then hiring accordingly.
Scaling tends to kill creativity; big companies buy innovation they can’t generate internally. For bootstrapped founders, consider an angel investor with aligned values before reaching for VC funding that trades autonomy for runway. Brad’s book From Pitch to Payoff covers the full landscape of startup financing options.
