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Host
Success story is a Square partner. Now your favorite neighborhood spots run on Square. You know, I was just at Panther Coffee here in Miami last week. And beyond the incredible cortado, what struck me was watching them seamlessly handle the morning rush. The barista mentioned they've been using Square to manage everything from inventory to building their loyal customer base. It's so much more than just that little white card reader that we all recognize. Square knows that local businesses can be big businesses. And as things get more complex, Square meets you at every opportunity. So whether or not you're expanding, expanding to new locations, building a loyal following, even covering cash flow gaps, Squares powering all the behind the scenes stuff that matters. They knock out today's to dos and they unlock tomorrow's what ifs. If you're ready to see how Square can transform your business, go to square.com go/success to learn more, that's square.com go/success square meet you there. In this lessons episode, explore why scaling a startup often breaks not from lack of customers, but from flawed models and weak retention. Discover how pricing strategy, expansion, revenue and customer fit drive sustainable growth. Understand the personal traits that separate high performing founders from those who stall. And uncover how choosing the right coach accelerates execution and long term success.
Interviewer
And I'm curious, where does, where does the the machine break? Where do you find entrepreneurs making the biggest mistakes when they get to that point and can't scale past that?
Guest Expert
Typically it's the reverse of what they think. So every I call it chocolate broccoli. People come to me because they think they need more customers and what they really need is a better model. So what does a better model look like? There's only three levers in SaaS. It's top of funnel, retention and monetization, right? So most of the time people have a retention problem but they don't want to admit it or they think it's good enough. So we need to keep more customers than we're losing because at scale that percent loss per month gets to the point where you'll hit what's called the growth ceiling. So retention is number one. Number two is monetization. So expansion revenue through upsells, cross sells, add ons, essentially your pricing. Most SaaS founders don't understand pricing economics in psychology and that is probably the lowest hanging fruit. Normally clients built too much stuff and they don't have a clear understanding of value drivers and how people should transition in between different plans and how to structure their plans to create that sales motion to pull people through that that Expansion. Right. So that's, that's the big thing where it's. Are they doing it wrong? Yes. Do they even know they're not doing it? No. Like, I mean these are things that if you haven't been doing this a long time, it's your first time building software company, you know, you've spent most of your time just trying to figure out how to get this thing built that you didn't spend any time on pricing optimization. And then finally once we have that, then it's all about sales velocity. Right? Like how do you pick the right customer, which I call a perfect fit customer, a ready to buy customer. So how do you decide who to focus on, who to sell to? How do you get the message in the market appropriately? What channels do you use? And then once you get their interest, what's the conversion process to get them from opportunity to customer and get that done in the shortest amount of time. So you don't have these long sales cycles. That's at a high level. And this is all covered in my ACEs growth engine framework. But most people start at the top, attract and then they go to convert, expand, scale. I almost start at the bottom because I need to make sure the model, the unit economics of your process actually makes sense to scale. Because if it doesn't, then we can waste a lot of time and money on marketing. That's just not going to produce the long term revenue retention that you need.
Host
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Interviewer
And no, I appreciate, I think that, I think that as if somebody's listening to this, even that awareness of, of what could be broken can drive them to look to the right resources and, you know, yourself or even, you know, a ton of others. But to understand all those points that you just mentioned that could potentially break when trying to scale, I think it's very important. Um, and I think that you sort of uncovered that recipe, you know, quote unquote, recipe for success when it comes to scaling startups. A lot of the things that you're mentioning I hear emulated from a lot of other very successful sales leaders. We're talking like mark Robert from HubSpot. He emulated especially the churn piece like mitigating the loss, you know, plugging that leaky bucket. That's another one that I hear a lot that people don't focus on. I've seen it a lot. And I don't want to, you know, reiterate everything you just mentioned, but I think that as people try and scale their company, it's really smart to understand, like you said, these things that are going to be huge growth inhibitors. Now I'm curious about. These are very Tactical growth inhibitors in terms of perhaps personality traits or I don't want to say that there's a perfect kind of startup founder, but what are the personal traits or growth traits that somebody should focus on internally that can allow them to be successful? Or is there just that kind of person that has the grit, determination, drive, perseverance, you know, self awareness, empathy, whatever. That is the most important trait to be successful as an entrepreneur because you work with so many.
Guest Expert
Yeah, no, I don't. I think, I think these traits can be developed and taught and learned. I think there's a natural, like, you know, you need to be a certain type of person to build a Mark Zuckerberg equivalent. Right. So there are, there are these like outliers in the data set, but there's this like very large medium, the mean of people. And when I look at that, most of my clients are bootstrapped, you know, incredibly successful. They all have a lot of characteristics. One is they're very growth minded, meaning that they're willing to invest in themselves, hence why they're coaching with me. They're willing to invest in themselves because they have confidence that with that knowledge they can do better than without it. Most people don't trust themselves. When you ask somebody like why do you not hire a coach? They'll make up a bunch of reasons. But the truth is, is they don't trust themselves to get knowledge, to implement, to get a return. That's the, that's the only reason why you wouldn't hire somebody who's been there before to help you. Because if I was going to, you know, climb Everest, you'd be an idiot. To not want to go learn from people that have been to the summit of Emir or Everest before you attempt it like that would just be honestly suicidal. Anybody trying to do it. Yet people do that every day in their business. And I think the reason why is they just don't have a lot of confidence in their abilities to translate that information into execution. So that's one thing. So the people that are going to succeed have a level of confidence about their ability to execute that most people don't. They're very much in tuned with feedback. What does this look like? It means that they're willing to pick up the phone and call customers to get feedback. They're willing to call, talk to their team and ask them their team questions like what do you need more from me as a leader? They're willing to instrument the metrics to know what's really going on in the business. A lot of founders that don't have the product or financial metrics around their business. I believe it's because they just don't want to know. They'd rather not know. Right. They put their head in the sand than actually pull that together because literally, there's so many tools out there that'll give it to you for free. That for you not to know what your churn or your expansion revenue or your activations are, your trial conversions or whatever they are, it's really just ignorance around, you know, getting that information and being scared to know. I mean, it all comes down to fear. I mean, Scott, that's the reality. So. But the traits is those things. They're curious. Curious is a big one. They're driven. They have a. They have a vision. This is a big one. They have a vision for their future that's way bigger than where they're at today, and they're able to expand that as they expand. You know, I think what happens sometimes people peter out because they actually hit. You know, I would just love to make 100 grand a year, and then they hit it, and then they just stay there forever, which is fine. Just not what I do. What I do is push people way beyond what they think's possible by showing them examples of that and reinforcing within them that confidence and courage and clarity of execution to make sure that that comes a reality.
Interviewer
And when they're looking for someone like you, there's a lot of coaches out there. How do they find somebody who's right for them? How do they audit that coach?
Guest Expert
Yeah, I mean, I had a lengthy discussion. One of my clients, Liam, is the founder of Time doctor And he actually interviewed me. So if people want to search that interview, like, I don't know him too.
Interviewer
He'S coming on for it, too.
Guest Expert
Yeah, yeah, but he. He's the one that asked me that question. I mean, here's how I hired my coaches. I want somebody who's been there before. Okay. Marcy, for example, one of my coaches back in the day, she built a company, brought it public. 5,000 employees, right? So been there before, has had, had results with other people. I think a lot of people are idiots of bonds in the sense that they know they can do it themselves, but they're not really good at getting other people the same results. I want to. I want to know that they've been able to get other people. I would reference, check the crap out of who they are. I think you should back channel. So if you see somebody on a Facebook ad, you should, like, see if you have mutual friends, reach out to them. Is this person a good person? What have you heard? How long have you known them for? A lot of fly by night coaches in the industry. It's unfortunate part that I, you know, I'm okay with because I understand that you know, performance over time is the best, the best example of success. It's just keep being consistent, do, do what you do over long periods of time and eventually you'll separate yourself from everybod else. But yeah, there's a lot of coaches out there that you know, come off and they're very flashy and they're, they're, you know, they're, they're selling with material things but when it comes down to it, their, their students results should be speaking for themselves. And that's, that's a big thing that I pride myself on is is client wins on a monthly basis and progress over everything than really good marketing per se. So I don't know, I think is a personal decision if you don't resonate with the person. If you're listening to me and you don't like the way I talk, you really shouldn't work with me because that's not going to get better. That's probably going to get worse. And I think that's important to know is is you need to find the person that you vibe with and that you feel is going to provide you with honest, direct, clear feedback. And, and if you don't feel that, don't force it. I think it's, it's a very personal decision on who you coach with.
Host
Thanks for tuning in. If you found this valuable, don't forget to hit that subscribe button so you never miss an episode. And if you want to dive deeper into this conversation, check out the links in the description to watch the full episode. See you in the next one. Monarch Money is a success story. Partner now. You know, it's weird. I'm doing well financially, but I have this constant low level financial anxiety that I was missing something because I have crypto on all these different exchanges. I have multiple Investment accounts, old 401ks, savings scattered everywhere. See, I knew the pieces were fine, but I had no idea if the whole picture made sense. I finally got Monarch Money to pull everything into one view. And the first thing I noticed, I had $10,000 sitting in a temporary savings account from eight months ago when I sold some stock. That's eight months, $10,000. It could have been working instead of just waiting for me to remember it existed. Also, it showed me that I was spending tons monthly on all these subscription services that I couldn't even remember I signed up for. Every Sunday morning it takes me five minutes to check everything. All my financial stuff in one place. No more wondering, no more anxiety. The Wall Street Journal just named it the best budgeting app of 2025. But honestly, it's more about finally having control. So don't let financial opportunity slip through the cracks. Use Code success@monimal money.com in your browser for half off your first year that 50% off your first year@monimal money.com with code success. Incogni is a success story partner now. Have you ever wondered how all those scammers get your phone numbers? All those telemarketers, how you're always drowning in all these spam calls? It's data brokers. Right now hundreds of companies are collecting and selling your personal information without your consent. Your address, your phone number, even your family members names to anyone who's willing to pay. And this puts you at risk of identity theft, scams and harassment. And that's where Incogni comes in. They contact over 230 data brokers on your behalf and legally force them to delete your personal information. No more spending hundreds of hours doing it yourself. Incogni handles all the paperwork, follows up on objections and keeps your data off the market with repeated removals. I've actually been using Incogni myself. It's scary and also incredible to see how much of my data was out there. But they get rid of it. They've got a 30 day money back guarantee, so you can try it risk free. Use my code success@incogni.com success to get an exclusive 60% off their annual plans. You have to take back control of your privacy today.
Date: September 6, 2025
In this "Lessons" episode, host Scott D. Clary sits down with Dan Martell, a serial entrepreneur and founder of SaaS Academy, to dissect the realities and challenges of scaling SaaS startups. The discussion delves into the misunderstood pitfalls founders face when trying to scale, the three crucial levers for SaaS growth, the psychology behind successful entrepreneurship, and the criteria for choosing the right mentor or coach. Martell's own journey from juvenile detention to building and exiting five companies underpins his hard-earned advice on business, leadership, and personal development.
Misconceptions About Startup Problems
Three Core Levers in SaaS
Martell outlines his ACEs growth engine framework built around three levers:
Top of Funnel (Attraction)
Retention
Monetization
Sales Velocity
Inverted Approach to Growth
Growth Mindset & Self-Investment
Willingness to invest in themselves reflects confidence in their ability to apply knowledge gained.
Martell draws a vivid analogy:
Execution Confidence
Feedback Orientation & Self-Awareness
Curiosity, Drive, and Vision
Key Criteria for Selecting a Coach:
Red Flags & Personal Fit
On the Hidden Growth Ceiling:
"Most of the time, people have a retention problem but they don't want to admit it or they think it's good enough.... at scale that percent loss per month gets to the point where you'll hit what's called the growth ceiling."
— Dan Martell (02:16)
On Pricing Being Undervalued:
"Most SaaS founders don't understand pricing economics in psychology and that is probably the lowest hanging fruit."
— Dan Martell (02:36)
On the Fallacy of DIY Approaches:
"If I was going to, you know, climb Everest, you'd be an idiot to not want to go learn from people that have been to the summit... Yet people do that every day in their business."
— Dan Martell (08:50)
On Personal Growth Traits:
"They're curious. Curious is a big one. They're driven. They have a vision. This is a big one. They have a vision for their future that's way bigger than where they're at today, and they're able to expand that as they expand."
— Dan Martell (10:36)
On Picking Coaches:
"I want to know that they've been able to get other people [results]... I would reference, check the crap out of who they are."
— Dan Martell (12:03)
End of summary.