In short
Episode topic: Brian O’Connor’s path from corporate strategy to entrepreneurship, using his “Choice Cascade” framework (goal, where to play, how to win, capabilities, management systems) to find product-market fit and decide when to think vs act.
Guest background
Brian O’Connor is a former banker/consultant (Deloitte management consultant; earlier banking) who worked on corporate strategy projects, including COVID PPP distribution. He later built a personal brand, coaching/courses, a fractional CMO firm serving small businesses and later billion-dollar brands, and launched a staffing company.
Key claims
A gift card followed him saving a project worth “hundreds of millions/billions” in PPP-related value; strategy matters, but early-stage businesses need tactics and delivery systems (people/process/tech). Product-market fit is “insane demand you can’t fulfill,” while monetization/business model is separate. Don’t tinker with acquisition metrics when delivery is the constraint.
Notable examples
PPP lending operations managing ~250 people; Mexico bank growth strategy targeting $300M new revenue; staffing pricing experiments (flat $4K search fee vs credit-based volume packages).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOFrom Corporate to Entrepreneur
0:45 to 2:44
Brian shares his transition from the corporate world to entrepreneurship.
“You're working with like billion dollar brands now.”
The Value of the Gift Card
2:44 to 4:42
Discussing a moment where Brian realized his worth in the corporate world.
“That was a crazy time in COVID because the PPP program was designed for these companies that are going to be shutting down.”
Understanding Fractional CMOs
4:42 to 7:05
Brian explains the role of fractional CMOs in the business landscape.
Growth Strategy Frameworks
7:05 to 10:47
Brian discusses key frameworks for growth strategy, including the 'choice cascade'.
“And for people who are listening, will you go through the five forces?”
Strategic Choices Explained
10:47 to 13:34
Explaining the importance of strategic choices and their implications for businesses.
“is like the most common thing to teach you in business school.”
Defining Strategic Choices for Business
14:01 to 16:49
Learn how to define strategic choices and management systems for business success.
“The theory is with all of these buckets, by the way, we identify strategy as different than best practices.”
The Importance of Knowing Your Goals
16:50 to 19:36
Understand why identifying goals is crucial for business growth and direction.
Balancing Speed and Confidence in Decisions
19:37 to 22:35
Explore the relationship between decision-making speed and confidence in business.
“I don't have an answer for that, but you still need to be worrying about these things.”
Launching a Staffing Company: The Process
22:36 to 25:09
Discover the thought process behind launching a staffing company from a marketing perspective.
“There's a speed confidence spectrum that like, depending on how big the bet is to you, you can, you can like kind of find your, your way into spectrum.”
Introduction to Actionable Business Advice
28:02 to 28:15
Learn about the importance of actionable advice in business acquisitions.
“whether or not the EBITDA multiple is good or there's customer concentration or there's red flags or green flags.”
Show all 18 chapters
Understanding Small Business Needs
28:15 to 28:59
Discover the distinction between strategy and tactics in small business.
“I probably failed seven or eight businesses.”
Navigating Product Market Fit
28:59 to 30:05
Explore the journey of finding product market fit in a business.
“Marketing tactics have gotten in the door.”
The Importance of Positioning
30:05 to 31:26
Understand how effective positioning can drive business success.
“He like product market fits his thing, right?”
Scaling Beyond Product Market Fit
31:26 to 32:48
Learn how to transition from finding product market fit to scaling a business.
“It's like pre when you need systems, like pre when you talk to me, it's you're you're like adjusting, slightly tweaking.”
Evaluating Business Models and Profitability
32:48 to 34:08
Discuss the relationship between product market fit and a viable business model.
“But that's where I see a lot of entrepreneurs make a mistake.”
Defining Product Market Fit
34:08 to 35:34
Learn how to assess product market fit and its significance in business.
“Cause when do you know that you have product market fit?”
Innovative Pricing Strategies
35:34 to 36:56
Explore different pricing strategies and their impact on customer retention.
“It's going to be like$8K for the search.”
Creating Value Through Advisory Services
36:56 to 39:45
Understand the importance of advisory services in recruitment and business success.
“90 to 95 % of our clients have one placement and they come back and they just keep buying more.”
Transcript
Automatic transcript. May contain errors.0:00I built an audience that had 85 ,000 followers and 14 ,000 people through my newsletter. I've got distribution. This is India proof at this point. I probably failed seven or eight businesses. So it's harder than I thought. You can have crazy product wearing a fit, but even a bad business model is a bad business.
0:17Brian, you're a prolific entrepreneur and you have kind of the target background of somebody who's listening to this podcast, which is you worked in the corporate world for a while and you had some amazing experience with JPMorgan Chase. that led you to be able to hop out on your own. And since then, you know, you've built a personal brand, you've done some coaching, you've sold some courses, but you've also built a fractional CMO company, which helps what you thought was going to be small businesses market and position themselves. You're working with like billion dollar brands now. And on top of that, you started your own staffing company.
0:52You've really gone from, hey, I'm W2. I want to become an entrepreneur to I'm an entrepreneur living full time. You're in South America right now. you're like a digital nomad it's amazing yeah did i miss anything no i think you'll have to clarify i wasn't at uh jp morgan i was a management consultant at deloitte doing corporate i'm sorry dang it all good all good uh and then before that i was actually a banker so i did a few years of like the finance boot camp and then i did six years of kind of like traditional corporate strategy advising to corporate executives why did you leave because you like if you're six years in and you're working at those kinds of companies, you can be making freaking great money.
1:31Why did you decide to become an entrepreneur? When I was in my early mid twenties, it was about money, right? It was about prestige and money. It was the hunt, right? And so I wanted to be investment banker, private equity. I wanted to be a consulting partner, like make millions a year and just like do that in the corporate world. I hit a point where it stopped becoming about money for me and became more about like building experiences and just like kind of the love of business i'd say i had a project where i was managing 250 people at like 25 years old 26 years old you know what was the project what were you doing like managing them what does that mean so in this case this example it was i don't know if you remember the the paycheck protection program during covid where they gave a ton of money to small businesses right i was at one of the banks helping give all that money to small businesses.
2:24Right. But it was a massive amount of money where like banks aren't set up to, to deliver that much. And so they needed to bring us in to figure out like, how do we like operationally, how do we get that much money to small businesses? And so I had to see 250 people like going through and figuring out like, how do we get that money to small businesses? Yeah. That was a crazy time in COVID because the PPP program was designed for these companies that are going to be shutting down. and the government didn't really have a clean mechanism to distribute that money. And so they said, let's go through the SBA.
2:56There's already like a funding mechanism through the SBA. And then all these banks that had SBA programs all of a sudden became the PPP lenders, right? So that was you. You were like working with those teams to get funds distributed really quickly. So it wasn't just a big team and a lot of funds. It was pretty stressful. It was. I didn't have weekends. like man it was like 8 a.m to 11 11 p.m like every every day do you know how much you help distribute it's gotta be billions right yeah we were top 10 jeez dude i think we made top six yeah so do you know the number what was the number i don't remember the tomorrow okay it was i remember top of my head i could look it up but i'd be lying if i made it up jeez you've seen hundreds of businesses not just in the corporate world but after you left you became this fractional CMO, like fractional executives are kind of a buzzword right now.
3:51And I know there's stuff in between, right? Leaving and the fractional CMO. Like, how did that come about? Why'd you go fractional? Finish the first question, which was like, Hey, from that project, like why go at all? Like why leave in the corporate world at all? Right. I was at a point where after that project, like that project was going, going to hell. Right. And like, I joined, I got pulled off of a strategy project I was on, which was like, basically it was helping a bank figure out if they should launch a new investment bank in Brazil, they were like, Hey, we need a strategist to come on and like figure out how to make this a reality.
4:22And it was a point where they didn't have, and we didn't have anyone on the bench who could do that. And so the partner at the end of the project, the partner turned and said to me, he's like, do you single handedly save this project? And they gave me it. And then he handed me a gift card. And so I remember sitting there being like, the amount of value I've created for a gift card is insane. I need to take a bet on myself and get a percent the value i create what was the value of the project it was that number that i remember okay billions it was a billions that would be billions in dollars distributed sure to to the consulting firm it was probably a hundred mil i'd say okay and you saved that project for a gift card okay hey thanks for saving us a hundred million here's a starbucks gift card don't spend it all in one sitting buy yourself a nice smoke a frap or whatever exactly so in that moment i mean i had a few moments it was like it wasn't just like one moment but in that moment i was like okay i i can really create some value but i need to take a bet on myself and capture some of that value right that wasn't the moment i left that like started the question started the challenge and then i had moments a few months later that had me leave to start like advising and that kind of stuff dude why cmo because it doesn't sound like you were doing marketing at the consulting firm you're at i mean you're helping distribute ppp funds you're looking at starting an investment bank in south america cmo doesn't make sense to me from that right yeah yeah so i was part of the growth strategy team growth strategy is marketing plus positioning that kind of stuff if you're familiar with like michael porter is five forces yeah five forces i was in porter's group and so what we did was figure out what does that mean i'm sorry i don't know what that means you were important like you were in you know michael porter no i don't so michael porter started a started a growth strategy firm right i'm like how do we so the kind of stuff that we do and then i was part of that firm basically i wasn't i didn't meet michael okay but so what we did was growth strategy and so what's growth strategy it's it's like what markets do we enter what products do we launch what customers do we target like how do we basically how do we generate more revenue for a company, which includes marketing, right?
6:37So to give you an example, a project, I went to a downed bank in Mexico. And in Mexico, we had to figure out how to generate 300 million in new revenue for the bank. And so what we did was we looked across all their business lines and had workshops with each business line on how do we come up with new product ideas, right? Look for areas to came up with a bunch of new product ideas, prioritize the product ideas, launch them, and then track the launch and execution of those ideas to generate 300 million for the bank. Oh, interesting. And that was in Mexico. That was in Mexico. Yeah. And for people who are listening, will you go through the five forces?
7:16Actually, so what's interesting is, so this is one framework we use in every growth strategy project, right? And then within the framework, we plug in these other mini frameworks. We actually didn't use the five forces right which is so interesting that is so like yeah there's a difference between academia and reality right and so like what we did and i'm sure like there's other like there's the seven powers there's the five forces there's all these like frameworks we can use but the one framework that we use in every corporate strategy project where i use today with my cmo clients is called the choice cascade yeah i'm obsessed i love the choice cascade uh the book if you're if if you want to deep dive in it there's this book called playing to win which is one of my favorite books on strategy and all it does is explain how the choice cascade like works in reality right uh and they use like procter and gamble as an example fascinating book anyway so the choice cascade what it is is anytime if you're trying to launch a new product you're trying to enter a new market penetrate a market more but the biggest thing is you're trying to create a competitive mode right if you're like if you're like playing in a red ocean let's say and you're trying to make sure.
8:23I'm so sorry. What is a red ocean? Okay. You keep dropping these words and I'm like, man, I thought I was an idiot before this podcast. And now I'm like, geez, Louise, 85 IQ. I've heard of a blue ocean. A blue ocean strategy is like just a ton of, it's a massive market, a ton of opportunity that you're launching into, right? Yes. It's the same. It's the exact same framework. Well, next month, it'll be a year since I started this podcast. I've had over a interviews. It's been a ton of fun, but I promised my wife at some point I would decide whether or not this was going to be a business or we would just continue to pay for it out of our pocket.
8:57And I'm exploring monetization, to be honest with you. There's not a ton of costs, but I do want to figure out a way to cover the editing and the packaging and the promotion costs of putting this podcast together. So I am looking for sponsors. I don't know what that looks like. If you've enjoyed this podcast and you've ever found some value and you want to sponsor, reach out to me, nickatcofounders.com, and let's get back into it. So if you think of that blue ocean, which is the, I believe it's BCG. It's a framework that basically says, Hey, it's a framework that my opinion, it's a book that could have been an email in my opinion.
9:28And that email subject header is just playing places. Other competitors aren't. That's really it. Right. A blue ocean is just a fancy word for a market where there's not a lot of competition. Okay. And the reason it's called blue ocean is there's the opposite of that, which is a red ocean. and imagine a red ocean is a bunch of sharks just biting each other there's blood everywhere in the water right the sharks are your competition those are highly competitive markets exactly a ton of sharks just by biting each other there's blood everywhere that makes a red ocean right and so the blue ocean is the absence of blood okay all right okay so now i'm up to speed the choice cascade yes okay so the choice cascade this is what we do basically i pull this out anytime time someone's like, I need to create a company advantage.
10:15I need to launch into a new market, which means either a new customer group, a new product, a new country, a new geography, et cetera. And so what that is, is it's five buckets. One, the first thing you do is you say, what's your goal or what's your aspiration, right? What's your goal for the business? Why? Because a strategic choice that you make for your business only makes sense relative to your goal, right? Which is why hot take SWOT analysis, strengths, weaknesses, opportunity, threats is like the most common thing to teach you in business school. Why? Because it's only a strength relative to your goal.
10:54I'm making this up. It's going to be a bad example, but we're really, really slow moving organization, but slow moving also means deliberate. And so if you're in insurance, that might make more sense because you like every bet you make is a big bet. But if you're in a SaaS product where you have to like constantly iterate and move fast, that's a weakness. And so every strategic choice that you make for your business only makes sense, whether it's a strength or a weakness relative to your goal. And so one rule of thumb that we have for is something a strategic choice is invert it. Take the opposite of that choice.
11:31And if it's stupid, then it's not a strategic choice. It's just a best practice. Here's an example. So if I were to say to you, our competitive advantage is that we love our customers, right? We have the best customer service. The opposite of that is we have the worst customer service. So like, is that an advantage or is that a best practice? Like, should we just take everything? Should we just like, it should just be industry standard to treat your customers well? And so like another example of that would be, hey, our organization is really deliberate versus our organization moves really fast.
12:04like on its face that isn't necessarily a good thing i mean yes most of the time you're like yeah we want to move fast right but if you're dealing with if you're in the fda you probably don't want to move exceptionally fast uh to get stuff through because you've got a bunch of testing criteria etc so it's so your goal when you're when you're talking about your competitive advantage and your is that your goal and your competitive advantage kind of one in the same no so let me Just high level go through the five buckets. So what you do is you first, you identify your goal. One, right? That's your aspiration.
12:38Who do you want to be when you grow up, right? What's your revenue goals, strategic goals? Like, where do you want to play? Where do you want to win? I'm sorry. What are your strategic goals and who do you want to be? Two, what markets do you want to play? Where do you want to play? Right? So that's what customers do you want to target? What industries do you want to be in? What products do you want to launch? What countries, geographies do you want to be in, et cetera? Three, how will you win? right and the important part one tip you do not do your where to play choice and your how to win choice separately they have to be combined right because every time you say we will play in the i don't know computer mouse market right there's no point in doing that without a winning and winning play and so you have to say we will play in the computer mouse market and we will win by distribution or whatever is that number three well where will you play and how will you win that's like correct the third question okay correct yep they are two different buckets but they have to be treated together right each where to play choice has to have a competitive advantage so one aspiration two where will you play three how will you win four what capabilities do you need to build or buy to make your strategic choice a reality and then five what management systems you have to put in place to ensure that the the strategy continues it doesn't like die after you're like six months of implementation i'm a chimp so i'm going to try to repeat this back to you all right well here's here's what i have here are my notes who do you want to be that's bucket number one right like aspirationally where do you want to be yes number two where do you want to play so what who's your target who's your icp who's your customer like what markets are you trying to play them the third one how will you win so what's your competitive advantage in that space in order to achieve those things what capabilities will you need to either buy or build to make it a reality and then the last one what management choices or what i guess systems we need to implement in order to realize that goal i guess the last one's really interesting i haven't thought about that what management choices like talk more about that last one i'll tell you the theory and the reality, right?
14:48The theory is with all of these buckets, by the way, we identify strategy as different than best practices. So if it's a best practice, we don't write it down. We just assume it is what it is. And that's just table stakes. That's not a strategy, right? So for example, a management system, we have to have EOS in place, entrepreneurial operating system, right? I'm making stuff up. We have to have meetings every week to talk about this thing, right? That's a best practice. You can argue it's a best practice or not, but like those are things that we just table stakes we're not going to talk about that in the strategy right but as an example here's an example four seasons four seasons the hotel right they go they say hey we are going to our product is our people not the hotel itself right yeah we're going to win by having incredible like having a client experience a luxury client experience right and so what are the management systems you need to have in place to make the luxury client experience a reality.
15:47Well, one example of it is that you give each employee a thousand dollars spend a month or whatever it is to be able to spend on, on their own discretion, at their own discretion. And like the KPIs you put into place that track client satisfaction are going to be different than if you emphasize something else. Interesting. Yeah. Yeah. So that makes sense now, right? Because I was thinking, oh, what's the management system you're going to have in place? It's like, okay, you have to put EOS or you have to put whatever they use in scaling up or, but that's table stakes. You should be doing that anyways.
16:24Yeah. If it's table stakes, that's not part of the strategy. That's just table stakes, right? That's just good best practice. If it's above and beyond table stakes, then it's a strategic choice. What's the book called again? playing to win fire book highly recommend yeah and it's the easy read too as i'm listening to that i didn't worry about these questions until years into my like journey as a leader manager entrepreneur because for me in the beginning it was like that question well who do you want to be it sounds so pie in the sky it's like i don't have time to waste on that i gotta close this customer i gotta hire this person i gotta whatever make the widget and it feels like you're wasting time however i've come to realize like if you don't know where you're going right if you don't know what your goals are then you are wasting your time like you're just running around like a chicken with your head cut off so finding these things early on is really important yeah and it also it depends on the size of your business too and what your goals are which ironically we're talking about identifying goals because like usually i get the call at the cmo business i get the call three million ish really five because like what happens is below one mil like you're still kind of just like finding out the systems and the strategy and stuff doesn't come into place until it comes into place earlier but it doesn't become mission critical until usually i get the call around three three to five is probably the low end of where we get the call um because like if you think about what strategy is from this perspective it's sitting there and like big brittany the thing like thinking about like your like your chest place pieces and wearing a play stuff right when you're still just kind of like constantly iterating and getting feedback loops at the speed of like a few hours or a day like your strategy is going to change all the time and so i think it's a function of sustainability once the business becomes more sustainable and predictable it's not fully sustainable predictable but like as it becomes more predictable than like when you're still trying to find market fit you can then start to like make more choices but then the other thing is the bigger the risk the bigger the investment like we're doing like three month strategy projects but because we're gonna put hundreds of millions of dollars on the line right and like when there's like multiple business units like the ripple effects are insane and so it's basically the bigger the bet the more the more thought you put into it that makes sense versus doing and finding out what i've always thought was interesting is you kind of think before you get into it that it's this clean process i think of the idea and then i got i have my positioning statement and we have our team and we do these meetings and whatever but the truth is you can't make decisions without data and you can't get data without doing but we're afraid to do until we feel like we're totally prepared so it's it's kind of this oxymoron is not the right word but this paradox right that many people fall into and that's where they get like too nervous to actually make a move but you actually find your product market fit in the process of doing it and i i'd say this a lot too if you're under a million or two million depending on what your business is depending on where your margins are is kind of my number eos doesn't matter right like pulling in your leadership team who's your leadership team when you're under a million right like your assistant or like you know your warehouse manager that's not really your leadership team like the point of these exercises is to get everybody on board because as you grow it gets harder and harder to maintain that core message and philosophy and so you need to get everybody on the same page right so you really don't get to those conversations beforehand, sub a million, even sub two million, again, depending on the business, like you're saying, you're just data gathering.
20:16Like, okay, what's working? What's not working? How do you balance that though? When you're under a million? I don't have an answer for that, but you still need to be worrying about these things. However, it shouldn't cause you to be paralyzed, right? Yeah. And we say worry about these things. It's the strategic choices and where you're going. Yeah. Like, like sitting down and I think it's important for you, let's say before you even launch a business? Hmm, where do I want to be? What market do I want to play in? How will I win? All those are really good questions to answer. However, you don't just do that once before you start the business.
20:47And then it's like, and then I became a billion dollar company. It might change when you get to 50 ,000 a month, it may change when you get to$100 ,000 a month, it's going to change again, when you get to 500 and 100 ,000. Like, there are different questions that sort of pop up at those points that you didn't even understand when you're getting the business started so as a cmo right like how have you seen what's the best way to balance the need to continually revisit these questions with you you also just need to get data so you can understand where your product market fit is yeah no that makes sense let's use that example of like when when we were launching uh those business units in mexico right those products uh we came up with like 40 to 60 different like products and like process optimizations and all that kind of stuff right But you're not going to test all of them.
21:36And so what you're saying is, how much research and thought should I put into before I make a business decision? It's basically what I'm hearing you say. It's basically, yeah. Yeah, it's great. And so there's a spectrum. And we literally draw the spectrum out on every product. Where it's like, you can be super confident, but it takes forever to get that level of confidence. And you can't be fully confident before you launch product. And so there's a confidence level versus speed. And so what we did was we would do, if we were to say, I don't know, we had one product that was a big bet and another was a small bet.
22:13The big bet, we would say, okay, we're going to go out and have customer interviews and we're going to do a market sizing. And we're going to do the full cascade where we come up with competitive advantages. And maybe we get all the executives and we bring in experts and do expert interviews. right and that takes a month for a month we're just sitting there maybe more month and a half where like we're just sitting there thinking right trying it basically it's like all we're trying to do is like find the spots we hadn't thought about like what mistakes can we avoid what landmines can we avoid and you sit there for a month and a half and think about it because it's a big bet right but there's other bets that aren't that big and we're like look we want to put all our resources a big one let's just put this in the market and test it and so i think like the spectrum.
23:00There's a speed confidence spectrum that like, depending on how big the bet is to you, you can, you can like kind of find your, your way into spectrum. As you're talking, I want to, I'll say it. And I wonder, I want to give you feedback. I wonder if it's when you're doing a couple million dollars a year and you've got a management team, you're paid to think that's your job, right? You're a thinker, you're a problem solver. Sub a million, you're not only paid to think like you're also the one who's doing the work so it just it gets it gets really hard i think if you're optimizing for speed in particular sub a million and then as the bets become bigger and you've got a management team right like then you're optimizing maybe for confidence i'm not saying you're ever on one side of the spectrum or the other no is is probably the maturation of a normal company right is it like yeah that's how they typically operate when you're small you need to optimize for the fast speed like feedback which is possible right but i think that's a false dichotomy where people say like yo you you have to just do and it's like you you can't think like i don't know i think at night sometimes you know like i'm in the shower thinking like oh am i doing the right advantage okay let's ask let's let's ask this so you have your cmo business and then recently you've also launched a staffing company And staffing companies are, we think in our own little bubble of Twitter that like, oh, everybody has a staffing company, but everybody doesn't have a staffing company.
24:26Like overseas talent is not a saturated market at this point. How did you think about launching that? Were you like sitting there overthinking it and getting the plan together? Or were you like, all right, speed to close. Let's just hop on this and start getting the feedback loop. Because this is essentially in practice what we've just been talking about. What did it look like for you? Yeah. So it's interesting because it's kind of a bit of both, right? So the backstory is I had my CMO business first. And I was building marketing strategies and marketing plans, everything we were just talking about now, right, for small businesses.
25:04And so the business would go, hey, that's great. But who's going to run it? Who's going to make it a reality? And so just to clarify, a system, when I say the word system, what I mean is three parts. People, processes, and tech. So at the time, my business was processes and tech. I was heavily focused on processes, like some tech, but people just wasn't as much of a thing. I was like, yeah, I got some friends doing this. They can do it for me. I knew in the back of my head the future state I want to get to, which is I want to have the three legs of a system. I need to have that capability. At the time, I had a friend I met at Neil Patel's mastermind.
25:44And he texted me and he was like, hey, I'm building this thing, which was the people side. And it fit perfectly into the business. And I was like, okay, do I want to build it myself or build it with a friend? And so I decided to go in with him. It was a natural outgrowth from the CMO, like you said. Correct. If they didn't have the systems to implement the recommendations you were making, and systems being people, processes, and tech, then you could be giving them recommendations till you're blue in the face face they may not see the results correct so when did you launch when did you launch the staffing company launch i don't know how to define launch because we started probably like june i would say of last year like we kind of like soft launched at jan fed did you do this process were you like all right let's sit down who do we want to be where do we want to play how will we win did you do this no so here's what happened so what actually yeah well kind of now i've done it so much that it's like always in my head like i can't like i can't turn that off right so if you tell me something i immediately think is that a strategic choice like how does it plug in like it's just kind of on autopilot now so it's all yeah but here's the interesting thing so this is the fascinating part i think so in when i first started even cmo business took so many iterations like i think when I, the biggest, the biggest surprise for me when I switched from corporate to entrepreneurship is how hard it was to find product market fit.
27:07In my head, I was like, I've created so much value for businesses. I understand the full life cycle. Like this business thing's going to be easy. Right. Which I'm glad I thought that because I wouldn't have done it otherwise. So, so yeah, I built an audience. I had like 85 ,000 followers, right. And 14 ,000 people reading small business owners reading my newsletter. Right. So I'm like, okay, I've got distribution. Like this is idiot approved at this point. Like I'm leaving and I'm just going to do this full time. Right. So I took the jump before I had like trash. The CMO jump. Yeah. So I'll tell you the full start.
27:38So before CMO, it depends on how you define a business in air quotes, but like, all right, now's the part of the show where I feel the most uncomfortable, but my therapist says I need to face my fears. So here we are. I've started a newsletter and I want you to subscribe. And what you're going to get every single week are the aggregated conversations from that week that I have on this podcast with an overview of what their business actually looks like. I'm also going to throw in a review of one or two businesses that are listed for sale. I'll give you my opinion on whether or not the EBITDA multiple is good or there's customer concentration or there's red flags or green flags.
28:07And then lastly, I'm going to give you one piece of actionable advice every single week on how to buy your first business. So click the link below, subscribe to my newsletter, and let's get back into the show. I probably failed seven or eight businesses. I define a businesses like i'm gonna launch an ebook ebook launch field all right i'll try something else right but so what happened was i i was talking about all the stuff i was talking to you now right strategy and then i went and tried to sell strategy to small businesses right but small businesses care more about execution and strategy i don't think they realize how important strategy is because they're kind of falling deaf ears right and so what i ended up finding out fast forward a bunch of iterations, I ended up finding out that I need to get my foot in the door with tactics.
28:55And then once I have them, I can explain to them what the strategy stuff is and go, oh, interesting. Wait, that's important. I've never thought about this before. Marketing tactics have gotten in the door. Marketing strategies will allow me to raise my prices and keep me there. Interesting. And then as you've been going, you found, hey, it doesn't even matter. I'm putting words in your mouth but you tell me yeah it doesn't matter how good my recommendations are doesn't matter how good i am if they don't have the people to actually implement these processes they're not going to succeed and that's why you've gone all in on this staffing company is that fair yep can i get meta with you get meta bring it it's like brian o 'connor was on his own product market fit journey i will i will but seriously right like it's you're just trying to figure it out yeah and like i think the the biggest thing that i wasn't prepared for is that like strategy makes sense for big businesses it doesn't make sense when you're finding product market fit right product market fits its own beast and like it was having like the difference between me and my co-founder is my co-founder was an entrepreneur through and through, right?
30:08He like product market fits his thing, right? Whereas I'm a strategist through and through, right? Like once you hit one to three, then I take over and I'm like, ah, this is my wheelhouse. And so I had this skill gap that I had to like overcome from when I left consulting. So now on how do you take a business from zero, right? To product market fit. And that was like, I didn't know how hard that skill gap would be. You know, I didn't know it was a skill gap. Yeah, you thought you had it. You thought you had it in the bag. Yeah. Yeah, I was celebrating before I crossed the finish line, right? That's a good analogy.
30:44So it's harder than I thought, especially because one of the things I focused on in consulting was, so part of strategy is positioning, right? And so remember, if you recall back to Choice Cascade, right? Where are you going? What marketing are you focused on? How will you win, right? But that's kind of your positioning. And positioning, to me, is the intersection of three things, right? Who's your customer? What's their pain? And how do you solve that pain better than anyone? And my belief is that is a hunt for product market fit, where it's like all you do is pull on one of those three levers 100 times until it matches and you go.
31:20And then when you go, you go really hard. Yeah. Then you build systems and scale. That's the main thing. It's like pre when you need systems, like pre when you talk to me, it's you're you're like adjusting, slightly tweaking. It's like you're slightly tweaking the customer. Right. Then you're slightly tweaking the pain that you're focused on. And then you're slightly tweaking the solution that you do that. Right. And then eventually it's like messaging that that positioning, all that kind of stuff. Right. But once you can like find the right intersection of those three things and message it in a way that the customer sees and goes, holy shit, that makes sense.
31:52I need that, then boom, you're off to the races. And it switches from a finding product market fit demand problem to do you have the systems to actually scale this thing problem? That's I see a lot of entrepreneurs run into this problem. I wonder your opinion on this is they get to the point where they've iterated, they've pulled the levers enough where they've gotten product market fit, but they just can't stop tinkering. Like there comes a certain point where you get product market fit and you see, oh, we're growing. And then you kind of stop tinkering with the offering. And you, like you said, you build systems around it.
32:25You throw gasoline on the fire so that you can really scale. But some owners, some entrepreneurs, they love the tinkering. So even when they've got something that's like, oh no, you've got a winning bid here, double down, put money into it. They're like, no, but I could make it better. No, our open rate's still not where it needs to be. Oh, our conversion rate's still not. Oh, we could still do this better, right? Like it's a really hard balance. But that's where I see a lot of entrepreneurs make a mistake. Do you see that ever? Yeah. I mean, I think that's just not prioritizing the right initiatives.
32:56What I mean by that is if you're tinkering with the open rates, when the real constraint on your business is like, we can't deliver that much, right? Like, let's say you have a, you found part of Margaret Fit, now you have a flood. You have a hundred clients. We're just begging to, right? In this imaginary world, you have a hundred clients begging for your offer, right? At that point, the constraint in your business is no longer the, like, I think of the, there's two parts of the business, right? One is like the delivery engine. You know, there's the, I'm sorry. One's the acquisition engine. You know, there's the delivery engine, right?
33:25If you're tinkering on your open rates, when the delivery engine is the constraint in your business, like you just haven't prioritized correctly. You know what I mean? It's that old adage, right? Like when you're a hammer, everything looks like a nail. And when your business gets to a spot where it's like, oh, the delivery. Yeah. The delivery piece of it isn't working. Well, it's like, I'm not good at that. I'm just going to continue to focus on the thing I'm good at, which is the customer acquisition. Right. Lots of people kind of fall into that. I want to ask you this question. So you named three things that make up product market fit, which is who's your ideal customer?
Read the full transcript
33:58What's the problem you solve? How do you do it better than anybody else? I'm wondering though, should there be a fourth where it's like, can you make money at this? That feels to me like an important thing. Cause when do you know that you have product market fit? Do you know at a hundred, it's like at a hundred thousand dollars a month. Cool. I, yeah, I have customers and I'm solving a problem and I'm doing it better than other people. Right. At this point, but maybe the market's not big enough to support a real business. Does that, does that make sense what I'm asking? So like, how do you think about knowing when, when you have product market fit versus when you're still figuring it out?
34:32Is there a framework you have for thinking about that? Well, I would actually separate those, those few, right? Because I think, well, I think positioning is one part of product market fit, right? That I tend to focus on positioning just because I understand the world better. I think what you're referencing is business model, right? So if I define product market fit, everyone's got a different definition of product market fit. It's that like elusive word. But I think of it as like when your offer has just insane demand, right? When there's just so much demand you can't fulfill. I separate how your offer is so good that you get so much demand from can you actually capture a percent of the value you create right that's your business model like you can have crazy product market fit but even bad business model it's a bad business you still have primary fit though but it's a it's a bad business idea okay so for you the the the monetary piece of it doesn't really fit into how you define product market fit correct yeah that's how i think about it i mean it's important i'm not actually trying to avoid that because then you'll make any money but i think i see it as this separate separate exercise for you it's like okay the the monetization piece is figureoutable what's not figureoutable is like if if you have something that people don't want that's not figureoutable it's like people don't want that so you gotta like you gotta change something within your product right yeah and that's always changing i'm i'm changing my offers we speak what do you mean what like what do you how are you changing it there's two parts that i'm thinking so i have two offers right so one is i'm compared to other uh talent agencies like i'm i'm ecstatic with how we structured ours right like most talent agencies, if you're like, hey, I need a customer service rep, I need an account manager, I need a graphic designer, et cetera, they'll charge you on average 20 to 30 % of the total compensation.
36:13It's going to be like$8K for the search. But at the same time, incentives are weird because then I'm incentivized to find the most expensive person or the best person. And so we have two options, two offers. One is flat fee. Instead of the percent of salary, we just charge a$4K search fee. And the reason I'm sad about that is because it's not just the the search like we also do that advisory like the advisory stuff we were just talking about with like hey are you making the right business decision or like we help you design and advise you on the rules right and so you basically get consulting with this search because i'm a huge fan of like uh one thing that we want to do is have reoccurring revenue right not where like basically like i place one talent you have such a good experience to come back for more i think like 90 to 95 % of our clients have one placement and they come back and they just keep buying more.
37:04We had one today put in their 15th placement, right? Dang, that's awesome, man. Yeah. So super happy about that from that perspective. So we have the flat search fee, but then we also have the volume play, right? And the volume play is basically like, hey, if you're going to do more than three hires in a year, we'll give you a package. It's basically a thousand dollars a month and that gives you five credits to the place for the year right what we're tinkering with now is is it works and clients love it behind closed doors i don't think it's the right pricing model oh yeah and the reason i don't think it's the right pricing model is because what happened is if i were to give you in my head it's a membership right where it's like You pay monthly.
37:50If I were to give you that membership option, most of our clients use all five credits in like a month to two months. And so what that means is that all the value from that membership is generated in the first two months. And then the whole rest of the year, you don't get value unless you buy another membership, which most people do. Most people are on like two, three, four memberships, right? And so because of there's a difference between payments and value, and I thought it was a membership, I actually think it's more of a financing and I'm not getting paid for financing. So I'm just, I'm doing a financing with a shitty bank.
38:24I think what's interesting about what you've described though, is that, cause you talk about in the positioning, what do you do better than anybody else? That, that last piece, like the advisory piece of helping somebody understand what they need. Many business owners know they need something like I'm too busy. I'm doing too much work, but what is that position that they need and how does it look and what are their duties and what are their responsibilities? Right? It's like before you even put up the job posting, that's like putting it up on LinkedIn or putting it up on indeed that's not the hard part it's crafting the job posting it's it's being clear and specific about who's doing what what the responsibilities and expectations are etc so I think your company offering that is really I think it's a really cool value proposition look most recruiting firms will just like connect you and they're done right I believe that if I can like give the talent the best likelihood of success yes, you'll grow.
39:15And when you grow, you need more. And so I'm so incentivized to help you grow because you come back and get more. And so what we do is we've realized the mistakes where people make the most mistakes in terms of their systems, their hiring, et cetera. They shoot themselves in the foot and they don't grow. And then we don't get another recurring customer. And so what we do is we hop on the kickoff call. And as part of the kickoff call, we go through the mistakes most people make, you know, when they're managing talent, when they're onboarding talent, the hiring talent that just gives them a lot of friction means their business slows, the results aren't what they want and they don't come back for more.
39:51And so I'm able to help them. The cool thing I like about this story is that obviously you're passionate about the question cascade. And we were able to walk through like a real example of how you did it in your own business, right? Like how did you think about positioning? How did you think about what you do better than anybody else? And you've actually launched, like you have a real business that you've launched us around that's doing well. It's freaking cool. No, it's exciting. I mean, definitely, I think the advisory, consulting, making sure you have a good business, these are definitely our advantage because of the background.
40:24And so we want to embed that deeply in the business to make sure anyone works with us. It's more likely to have a business that grows and their talent is actually used in a way that gets the most out of everyone. They don't have to get frustrated by lack of communication and lack of not doing the right tasks and actually help the business grow.
From the publisher
MY NEWSLETTER - https://nikolas-newsletter-241a64.beehiiv.com/subscribe
Join me, Nik (https://x.com/CoFoundersNik), as I interview Brian O'Connor (https://x.com/BrianFOConnor).
In this episode, I sit down with prolific entrepreneur Brian O'Connor to uncover how he walked away from a high-stakes corporate strategy job at Deloitte to build his own business empire. Brian reveals the exact breaking point that pushed him to leave the corporate world, it involves single-handedly saving his consulting firm $100 million and receiving a coffee gift card in return!
We dive deep into the brutal reality of finding product-market fit, why traditional SWOT analysis is completely useless, and the secret corporate frameworks like the Choice Cascade that can help you create an unbeatable competitive advantage.
Brian also shares the crazy story of managing 250 people while distributing billions in PPP loans during the pandemic, and how his journey ultimately led him to start a highly successful fractional CMO company and a unique staffing agency. If you want to know how to transition from a W2 employee to a thriving business owner, or how to navigate a highly competitive Red Ocean, you won't want to miss these insights.
Questions This Episode Answers:
- Why is traditional SWOT analysis considered a waste of time for most businesses?
- What is the Choice Cascade, and how can it give you a massive competitive advantage?
- How do you know when you've truly found product-market fit?
- Should you prioritize deep strategy or raw execution speed when your business is making less than $1 million a year?
- How can rethinking your business model and adding an advisory component completely transform your customer retention?
Enjoy the conversation!
__________________________
Love it or hate it, I'd love your feedback.
Please fill out this brief survey with your opinion or email me at nik@cofounders.com with your thoughts.
__________________________
MY NEWSLETTER: https://nikolas-newsletter-241a64.beehiiv.com/subscribe
Spotify: https://tinyurl.com/5avyu98y
Apple: https://tinyurl.com/bdxbr284
YouTube: https://tinyurl.com/nikonomicsYT
__________________________
This week we covered:
00:00 Introduction to Brian's Entrepreneurial Journey
01:23 Leaving the Corporate World
02:10 Managing a Massive COVID-19 Project
03:40 The Decision to Become a Fractional CMO
05:48 Understanding Growth Strategy and Competitive Advantage
07:42 The Choice Cascade Framework
10:42 Strategic Choices for Business Success
16:41 Balancing Strategy and Execution in Early-Stage Businesses
20:47 The Evolution of Business Questions
21:46 Balancing Confidence and Speed in Business Decisions
22:07 Launching Business Units in Mexico: A Case Study
24:51 The Role of Strategy and Execution in Small Businesses
27:26 The Journey to Product-Market Fit
30:44 The Importance of Positioning and Iteration
34:56 Innovative Pricing Models in Talent Agencies
38:58 Advisory Consulting as a Competitive Advantage
