How to Know When Your Business Is Ready to Scale

How to Know When Your Business Is Ready to Scale written by John Jantsch read more at Duct Tape Marketing

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Overview

Scaling too fast kills companies. So does scaling too slow. But most business owners never stop to ask whether they have actually earned the right to scale at all. In this episode of the Duct Tape Marketing Podcast, John Jantsch sits down with Mark Roberge, co-founder of Stage 2 Capital, founding CRO of HubSpot, and author of The Science of Scaling, to unpack one of the most misunderstood decisions in business growth.

Mark helped take HubSpot from zero to IPO, then spent years at Harvard Business School teaching founders why so many fast-growing companies implode. His framework asks a different question: instead of “how fast can we grow,” ask “have we proven we deserve to grow?” The answer requires evidence, not instinct, and not pressure from investors.

This episode is for small business owners, agency owners, and entrepreneurs who are thinking about adding headcount, launching new channels, or entering a new stage of growth. If you want to scale without destroying what you built, this conversation is your roadmap.

Guest Bio

Mark Roberge is the co-founder of Stage 2 Capital and the founding Chief Revenue Officer at HubSpot, where he grew the company from zero to IPO. He later joined Harvard Business School as a senior lecturer, teaching founders and operators how to scale with discipline. He is the author of The Sales Acceleration Formula and The Science of Scaling, and has spent the past decade as an investor, board member, and advisor helping companies navigate the gap between early traction and sustainable growth.

Key Takeaways

• Product-market fit is not a revenue number. It is a retention metric. If customers are not staying and using your product, you do not have it yet, regardless of how many you have signed.
• Go-to-market fit is the second gate before scaling. It is measured by unit economics, specifically whether you can acquire and serve customers profitably.
• Scaling revenue too fast is a structural problem, not a motivation problem. Hiring 27 reps when you only have one requires 270 qualified interview screens, management infrastructure, and demand generation that most companies simply do not have.
• Build a monthly hiring pace instead of a January 2nd headcount dump. Steady, intentional growth gives you time to build the systems that support each new hire.
• The CRM funnel should not end at closed-won. Retention, engagement, and expansion are stages, not afterthoughts. The Marketing Hourglass is the right model.
• Leading indicators of retention can be defined simply. Slack tracked whether 80% of customers sent 2,000 team messages per month. You do not need a data science team to build a version of this for your business.
• A feature is not a moat. If a competitor can replicate your advantage in six months, it is not long-term defensibility. Founders need a vision for what makes them unbeatable over time.
• The ability to up-level the executive team around you as the company grows is one of the strongest predictors of a successful exit. It is also one of the hardest skills to develop.
• Sometimes the business outgrows the founder. The COO or president model is not failure. It is graduation. The reframe: someone else does the work you hate so you can focus on the work you love.
• AI is accelerating faster than society can adapt. Mark is donating book proceeds to McLean Hospital for mental health research, because the people building this technology have a responsibility to help manage its consequences.

Great Moments (Timestamps)

[00:02] — The opening question that reframes every growth decision: are you betting on a business that is not prepared to win?

[04:04] — Mark defines what it actually means to earn the right to scale, and why most founders get this wrong from the start

[06:25] — The two-step framework: product-market fit and go-to-market fit explained clearly

[09:51] — Half scale too fast, half too slow. Mark explains the Groupon and WeWork examples as two failure modes

[11:40] — How to measure product-market fit without a data science team, using Slack and HubSpot as real examples

[13:29] — John and Mark align on why retention and advocacy belong inside the customer journey, not outside it

[16:31] — Why a feature is not a moat, and what long-term defensibility actually requires

[17:43] — The London School of Economics study on what predicts a strong startup exit (the answer will surprise most founders)

[20:33] — The mental health connection: Mark shares why he is donating proceeds to McLean Hospital and what the AI era demands of technologists

Memorable Quotes

“The decision on when to scale is usually when someone hands you a fat check, which doesn’t sound that strategic.” — Mark Roberge

“Do not let the dashboards and sales funnels in your CRM end at closed-won. That is literally step four of seven.” — Mark Roberge

“A feature is not long-term defensibility. If your competitor can build it in six months, you don’t have a moat.” — Mark Roberge

“We’re basically offering to pay for someone to do all the work you hate so you can do the work you love.” — Mark Roberge on helping founders let go

“We as technicians need to diversify our efforts away from just building and profiting toward helping society adapt to this new world.” — Mark Roberge

Duct Tape Transcript

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John Jantsch (00:02.19)

So what if every time you hired too fast, launched a new channel or added a service line, you were making a bet that your business actually wasn't prepared to win. Hello and welcome to another episode of the Duck Tape Marketing Podcast. This is John Jance and my guest today is Mark Roberge. He's the co-founder of Stage Two Capital, founding chief revenue officer at HubSpot and the author of a book we're going to talk about today, The Science of Scaling.

Mark helped grow HubSpot from zero to IPO and then brought what he had learned into Harvard Business School where he taught founders how to grow without blowing up what they built. His framework gives business owners a way to use evidence rather than instinct or outside pressure to decide when they've truly earned the right to scale. So Mark, welcome to the show.

Mark Roberge (00:53.259)

Thanks, John. That's not my copy and I love it. Seriously, I love how you put it.

John Jantsch (00:59.105)

Awesome. good. Well, you know, we were talking before we got started, you and I met some 20 years ago when HubSpot was a nascent business. think maybe the first conference there were 500 people, something of that neighborhood.

Mark Roberge (01:04.916)

Yeah.

Mark Roberge (01:11.393)

Yeah, I was like in a Marriott in Cambridge. I have like, I remember specifically a couple of things about you. I think you were the most famous one of our early partners. I think I remember my last in-person chat with you was in some steakhouse in like South Boston or something. Cause I remember two people came up to you and asked for your autograph and you were like super humble about it. And I'm like, oh my gosh, this is crazy.

John Jantsch (01:21.271)

Ha ha ha!

John Jantsch (01:27.438)

You

John Jantsch (01:35.288)

Well, I'm glad I wasn't a jerk. That's for sure. Awesome. Well, let's get into your book a little bit. So I mentioned HubSpot, Harvard, now you back companies as a VC. Did something you learned or showed up across all three of those roles kind of make you say, I need to write this book?

Mark Roberge (01:37.365)

Hahaha

Mark Roberge (01:54.207)

Yeah. Yeah. It's like, it's kind of funny that we can unpack as much as you want, but in reflecting the last 20 years of my life professionally, I've given up on having a plan because I never intended to go into sales. I never applied for HubSpot. I never applied or intended to be a professor at Harvard. I never intended to start a venture capital firm.

And I never intended to write either the sales acceleration formula 12 years ago or the scientist's killing last year. These were all things that like people were like, would you be willing to do this? So they did, they do just like show up and the way that this one, as both books unfolded was a, like you, I am blessed with the opportunity to do a number of keynotes every year. and I, for the big ones like saster, I tended to try to do something fairly original for the year.

So I've, you every year I do something original. So I've given like 20 to 25 brand new speeches over the last decade. And this one was just like a pattern I saw after like eight years of being out of HubSpot as an independent board member, as a professor, as an advisor, as an investor, in why companies, the few that went IPO and billion dollar valuations versus the ones that went bankrupt was just this.

really non-strategic, non-rigorous perspective on when to scale and how fast. And half do it too early, too fast. Half of them wait too long and go too slow. It's more about going the optimal time. I started speaking about it and I'm like, it's ridiculous how many classes and rigorous frameworks we have on accounting for and accruing revenue, but not on scaling revenue. And it just went viral and kept speaking about it, kept writing about it. And then Stanford was like, hey, can you write this up?

And here we have it.

John Jantsch (03:47.128)

So the term, you kind of alluded to it, but I'll say it directly, earn the right to scale. It does a lot of work in your framework and your talk. So what does a business owner actually have to prove or do to prove that's true? Like, when do they know I have the right to scale?

Mark Roberge (04:04.286)

Yeah, it's kind of interesting how it unfolds right now. I I've done this with like tractor companies in Brazil and pharmaceutical companies in Japan, but mostly with software companies in Silicon Valley. And it's kind of funny how it's decided. Like the decision on when to scale is usually when someone hands you a fat check, which doesn't sound that strategic.

And so I try to unpack it as two steps that are sequential. One is product market fit and the other is go to market fit. And usually you're like product market fit, like duh, product market fit, duh. But like, what is product market fit? You know, I think a lot of people will say I'm ready to scale when I have product market fit, which I think is a great answer. But then when I ask them what product market fit is,

I get a lot of different answers, most of which are about a certain revenue number, a certain customer number, a certain number of inbound leads. And then I'm like, well, okay, cool. Let's say that you have 200 customers or like 500 inbound leads and everyone's buying, but like people stop using the product. Do you have product market fit? And they're like, okay, no, but

I'll just start, I'll just listen to them and build the product to appease their needs. And I'll be like, okay, well, how will you know when you've achieved it? And they'll be like, when they keep using the product and don't churn. And I'm like, exactly. So like that, that's like the first kind of like pivot mentally for folks is I encourage you to define product market fit, not as a revenue acquisition.

metric, but as a revenue and customer retention metric. And the book talks about how to extract that long-term lagging indicator back to something that you can evaluate in the first week of a customer being with you. Okay, so that's step one, product market fit. And then if you think about it, once you've achieved product market fit, all that means is that when you sign up 10 more customers, they're gonna see value that you promised and stick around.

John Jantsch (06:00.866)

Yes.

Mark Roberge (06:25.372)

It doesn't mean that you've proven that you can acquire and serve them profitably. And that's what go-to-market fit is. And it's measured by UNEconomics. So that's really the, probably the simplest way to describe the work is these two sequences of product market fit and go-to-market fit as measured by retention in the first one and positive UNEconomics in the second.

John Jantsch (06:29.506)

Mm-hmm.

John Jantsch (06:46.018)

Well, since we're defining terms, we probably better step back because I bet you if I asked 100 people, 10 people, 100 people sounds like too much work. If I asked 10 people what the word scale means, we'd probably get a bunch of definitions, more leads, more staff, more tools, but how do you define it?

Mark Roberge (06:59.21)

Sure. Sure.

Mark Roberge (07:07.528)

Yeah. So once you are ready to scale the way and that to your point, yeah, that can mean a lot of things. It could mean how do we scale our culture? How do we scale our engineering team? How do we scale our office space? Blah, blah. First off, I'm, I should be more clear that I'm talking about scaling the revenue. And to your point, scaling revenue, the inputs to that vary quite a bit by business by business. if you're a consumer business, you may just have to spend more on marketing. Something that you know a lot about Joan. if you're a B2B.

John Jantsch (07:15.094)

Mm-hmm.

John Jantsch (07:21.92)

Okay.

Mark Roberge (07:37.513)

sometimes you have to scale fancy outside salespeople if you're selling like rockets to governments. And sometimes you do it through PLG. And again, it's more of like a marketing exercise. So I really talk about scaling the revenue and the principles, apply, whether you're doing it through pure marketing or through, through sales head count. let's for simplicity, let's just talk about scaling through sales head count and the

Big pothole that people make there is even if they follow the guidance of like, let's achieve product market fit first and then go to market fit, and it could take a day, it could take a week, it could take a month, it could take a year, whatever, and now we're ready to scale, they raise money and then they have a target for the year and they hire like 27 reps the next week.

even though they only have one on the team today. And there's just no appreciation of the new capabilities that are needed to hire and onboard and manage 27 reps. Like just like, let's take one piece of it, which is let's kind of pontificate that the hiring quality might be correlated to the number of interview screens we do, qualified interview screens to the hire. If I do,

two interview screens and make a hire, I'm probably not gonna make as good of a hire as if I did 10 interview screens and make a hire. So if we're trying to do 10 and we're making 27 hires, that's 270 qualified interview screens. Where are we getting those candidates? Who's doing the interviews? Nevermind, where's the demand gen gonna come from? Who's gonna ramp them? What about the managers? It's just too driven from a Google Sheet or Excel, and so the simple pivot philosophically is,

Don't think about it as putting the annual plan together and hiring all those reps on January 2nd. Think about it as establishing a hiring pace every month or every quarter. 10 reps a month, boom, boom, boom. As opposed to like 37 at the beginning of the year.

John Jantsch (09:51.791)

So there's all kinds of horror stories of companies that blew up because they grew too fast. Would you say that they scaled too fast or they didn't scale fast enough?

Mark Roberge (09:57.47)

Yes.

Mark Roberge (10:04.928)

Both. have, like I said, it's about half and half. I mean, I would say like the classic examples out there, like an old school one is Groupon, which I think if you look at it from this lens, never really had product market fit. they just like, the promise was like, if you're a Chinese restaurant and give these coupons away, you'll get new customers, but it was really just the existing customers. And then maybe like WeWork never really had go-to-market fit. And that was pretty famously documented story.

John Jantsch (10:21.486)

There's Buzz. There's Buzz.

Mark Roberge (10:35.36)

The ones that didn't scale fast enough, we just don't know, right? Cause they're like, I can name some in our portfolio or people I've worked with over the years, but the reason why we don't know them is cause they just sat there and they were like, they had something, but the co-founders just like wanted to just go too slow and continue to do founder selling and wanted to run a profitable business when it needed to be a blitz scale business. And there's nothing wrong with running a profitable business. just, if you're trying to win in the AI customer support,

John Jantsch (10:38.702)

Yeah, yeah.

Mark Roberge (11:05.258)

category today, you can't be profitable right now. Like there's just certain blitz scale risk that you have in your category that needs to dictate how fast or slow you go.

John Jantsch (11:06.638)

Yeah.

John Jantsch (11:16.056)

So one of the key elements in science of scaling is evidence over instinct. So if I don't have a giant data team, and I know AI is actually solving some of this right now, but what does evidence actually look like at a startup or smaller business level?

Mark Roberge (11:29.768)

Mm-hmm. Yes.

Mark Roberge (11:40.117)

Yeah, I mean, you don't, you definitely don't need like a sophisticated data science team. You don't even need AI agents doing this stuff. Let me just give you like a really simple example. So we talked about product market fit is where I'm, I'm proposing to everyone that it's more about customer value and retention as opposed to customer acquisition. And obviously you need to acquire customers to eventually make them valuable. So it's an input to it.

John Jantsch (11:48.526)

Okay, all right.

Mark Roberge (12:08.34)

The retention is a lagging indicator. So we needed to find a leading indicator of retention. We can't wait a year to know if we have product market fit. I need to know like the week after I acquired the customer or the month after. And so what the book and the work I've been doing with companies for last decade is to help them define their leading indicator of retention. What is it that we can observe in the first month of a customer's experience with you, your product, your service, whatever.

that if we see that, they'll be with you forever. And if we don't, they'll probably churn. And so like, I frame it as P percent of customers do e-event every tee time. Okay, so that sounds like the programmers on the audience are like loving this right now. The history majors are like totally lost, right? So like, just to bring that to life, Slack, 80 % of customers send 2000 team messages every month. HubSpot, 80 % of customers use five or more features in the platform every month, right?

John Jantsch (12:53.55)

You

Mark Roberge (13:08.564)

These are things that can be measured in the first month to give us insight. If we're at 80%, we probably have product market fit. If we have 10%, we definitely don't. I don't need a data scientist to evaluate that. Okay, so these are not overly complicated, like PhD math type things.

John Jantsch (13:20.174)

So.

John Jantsch (13:29.922)

One of the things I've been preaching for 20 years is that when we talk about the customer journey, that retention and advocacy and all the things that come after somebody becomes a customer are part of the customer journey or should be part of the customer journey. And for so many people, it's let's get a customer. And I think what you're really certainly hammering home here is this idea that you're not going to scale without retention and without

Mark Roberge (13:44.234)

Yes!

John Jantsch (13:59.382)

know, referrals or whatever you call it. Yeah.

Mark Roberge (14:01.984)

Spot on. mean, when I hear people like you say this, the conviction continues to escalate, right? Because it's like, another way to say what John is saying here is, let's just talk really tactically. Do not let the dashboards and sales funnels in your CRM end at closed one. That is like literally step four of seven, right? Like let's just like really step back, like very, very like basic, like.

John Jantsch (14:20.468)

Yeah.

Mark Roberge (14:31.654)

know, opportunity stage one is, you know, business, like discovery call and like business and you know, metrics definition. Step two is product validation, demo, blah, blah. Step three is closed one. Step four is set up. Step five is regular engagement. Step six is retention. That's the funnel.

John Jantsch (14:52.558)

He

John Jantsch (14:59.438)

Yeah, yeah, yeah, yeah. I actually refer to it, have been referring to it as the hourglass, you know, with the idea being that, the funnel, right, but then it goes back out again. Yeah. Yeah.

Mark Roberge (15:06.26)

Totally. And expands. Exactly, because you expand more and like lot of people like winning by design with Jaco and like that's just a great way, the bow tie. A lot of people like it's a really good way to think about it because that usage, it represents that the usage and should grow.

John Jantsch (15:16.589)

Yeah.

John Jantsch (15:23.576)

So you were at Harvard and name a dozen schools, Stanford, that a lot of people go to those because they've got a big idea or they wanna have a big idea. They wanna turn out the next Google. I'm sure you encountered many founders or would be founders in those environments. What would you like if you were, I'm sure you did this in your class environment.

tell them they're gonna get wrong or how would you coach them of how you think they're thinking about it incorrectly?

Mark Roberge (15:58.009)

I mean, there's a lot to that. I think we covered a lot of them related to the work in terms of like, you know, being more precise around having the business fundamentals in place to be prepared to scale and how you go about scaling. I would say,

I guess I'll add two more to it that come up a lot, one that's related to revenue development to some degree and one that it really isn't. The one I'll mention is having a plan for a moat. And I would say like, when I ask people what their long-term defensibility will be, they often tell me about a feature.

John Jantsch (16:31.992)

Yes.

Mark Roberge (16:45.468)

And when I asked them if they are correct and they start crushing it and start winning, and then the competition realizes it, how long will it take them for them to build that feature? And they say six months. And I say, that's not long-term defensibility. So, so you really have to like, you don't have to prove it on day one. Cause oftentimes it might take something that you have to kind of take one of those design big start small approaches to it.

John Jantsch (17:02.58)

Hehehehe

Mark Roberge (17:14.464)

but you really need to have a vision around if you are right, there will be lots of copycats and the incumbents will try to take you out and you need to make sure that you win there. The other one, unless you want to talk about that, John, I have one more that I can throw out that's pretty popular. Yeah, yeah, the other one that's interesting, I think it was a study done at London School of Economics where they looked at like, I don't know, 5,000 seed funded businesses like 15 years ago and.

John Jantsch (17:22.637)

Yeah.

Yeah.

John Jantsch (17:31.17)

Yeah, yeah, go for it.

Mark Roberge (17:43.282)

and tried to evaluate the commonalities for those that like exited at, you know, very strong exit. The number one correlation was the founder's ability to up level the executive team around them as they went through the various phases of growth. And it's like, it's so pronounced in my journey with some of these folks. It's like, it's so hard to do too. Like it's so hard for like a founder to like stare someone in the eyes who've been there in the trenches with them from day one for three years.

and be able to communicate that they are over their head and that the business needs someone ready for the next stage. How you deliver that, how you recognize it, how you have the guts to say it, how you like move through that and still feel like a human and still feel like that person has been made whole. Like that's such a difficult skill to build, but that there's so much correlation with successful founders and CEOs and in

developing and executing that skill.

John Jantsch (18:43.372)

Well, and let's take it up one level. Many times the business outgrows the founder, right? So they may be having that conversation with themselves, right? Yeah.

Mark Roberge (18:48.714)

Sure. It's very rare that they're there. Totally. Yeah. And that lots of times the board has to manage that. think we, we went from an, like a culture or like a tactic around that. would say in the eighties and nineties when venture capital was much smaller and startups were, it just, was a much smaller portion of the economy. VCs were notorious for investing in these young technicians and then

fire in them. And I think in the early 2000s, venture took a different approach. They didn't want to get a reputation for firing CEOs. So they did what I call the Sheryl Sandberg, which is to like bring in the, the operator, but keep the CEO, which is good. think that's great. think a lot of times that CEO can sort of graduate up to being a

face to the organization, a driver of the culture, a person to be in key meetings with customers, to be on the road, but like don't have to be or nor qualified to be like the day-to-day operators, hence like today's COO president role. So, but yeah, sometimes founders, they're like not willing to let go. And I have to be like, I have to be like, do you even understand that you have graduated to an era and scale that every CEO

John Jantsch (20:00.782)

Yes, yes.

Mark Roberge (20:15.519)

founder dreams of, we're basically offering to pay for someone to do all the work that you hate and have you just do the work you love, which is product vision, talking to customers and talking to the market. So it's like, it takes a little reframing, you know.

John Jantsch (20:17.56)

Yeah, that's right.

John Jantsch (20:23.598)

You

John Jantsch (20:33.16)

Yeah, yeah, yeah, yeah. So you, I think your PR people mentioned this, they're donating the proceeds to the book to McLean Hospital for Mental Health Research. Is there an intentional connection of the subject of scaling to mental health?

Mark Roberge (20:42.014)

Yeah.

Mark Roberge (20:48.113)

my gosh. Huge. Well, not so much. It's very light. It's more of an intentional connection to the author. and it's just something as you've experienced, John, it like you get up, you get up in the morning and do these things three times more aggressively when you have a cause like this around you. And there's two personal reasons and thank you for providing a platform to talk about them. The first one is mental health has played an enormous piece in my own life.

John Jantsch (20:55.992)

Yeah.

Mark Roberge (21:18.259)

I have been a caregiver, a direct caregiver to many loved ones and I've been a patient. And I can stand here and say this because I've been blessed with certain resume wins that society values and I can be braver than most. And I'm sure by saying that some people may be hesitant to work with me. And I just think we need to fight that stigma more. Like we've come a long way in a generation, but

Even to this day, I think a lot of people will be interviewing a candidate and find out they survived cancer 10 years ago and it will elevate their perception of them versus if they found out that they overcame a serious mental illness, they may have some concern and both are just a disease. They're often genetic. So that's part of the personal driver. And the second one is I think in this moment in tech, there's a hundred times more capital talent.

John Jantsch (22:02.03)

Yes.

John Jantsch (22:07.308)

Yes.

Mark Roberge (22:17.009)

an effort going into building AI and next to nothing in helping society adapt to the world that about to become. And I think we as technicians need to change that. We can't delegate this to Washington or economists. They're just not close enough to it. And we just need to like really diversify our efforts away from just building and profiting toward

John Jantsch (22:25.347)

Yes.

Mark Roberge (22:44.265)

helping society adapt to this new world. like with every tech revolution, we ended up better as a society, but there are scars along the way. It happened with the internet. They're about to be really bad with AI if we don't do anything. So I think we all need to find a little thing to do. And right now that's my little thing to do.

John Jantsch (22:51.734)

Yes.

John Jantsch (22:59.914)

Awesome. Well, I appreciate you taking a few moments to stop by the Duct Tape Marketing Podcast. Any way you'd invite people to connect with you, find out more about your work as well as your latest book.

Mark Roberge (23:11.315)

Yeah, I'm all over. mean, LinkedIn is probably where I'm most at. I'm trying to hang out on TikTok more, John, just to like, because I need to like talk to these 22 year old founders as well, which is awesome. So I'm trying to find where they are. But I'm mostly on LinkedIn if folks want to go on there and collaborate.

John Jantsch (23:25.55)

Well again, I appreciate you stopping by and hopefully we'll run into you someday in a steakhouse in South Boston. I don't know how much that'll be worth to you, if you got a pen, I'll do it. All right. Thanks, Mark.

Mark Roberge (23:32.305)

I'd love it and maybe I'll ask for your autograph, John.

Mark Roberge (23:42.578)

All right, it's great to see you. Thank you.

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Before You Touch Your Marketing, Do This First

Before You Touch Your Marketing, Do This First written by John Jantsch read more at Duct Tape Marketing

Most founders come to a marketing conversation with a tactic already in mind.

Better website. More leads. A LinkedIn strategy. Maybe an AI tool that’ll finally make content easy. The tactic changes. The assumption underneath it doesn’t: the marketing needs to change.

After 20 years doing this work with small businesses, here’s what I’ve actually seen. The marketing is rarely the first thing that needs to change. The founder’s clarity is.

Not because anything is wrong with the founder. Most of the founders who ask for marketing help are working hard and carrying a lot. The problem isn’t effort. It’s that they’ve lost the ability to see their own business clearly.

Why that happens

Five years in. Ten years in. You’ve absorbed a hundred opinions about what your business should be, and somewhere along the way you drifted from what it actually is.

You’re making decisions based on the business you remember, or the one you wish you had. Every new strategy you install inherits that confusion.

I watched a founder last year build out a full content strategy, hire a new agency, and rewrite their website. Same results they’d been getting for 3 years. The strategy was fine. The clarity underneath it wasn’t there.

The Founder Portrait: 4 questions most founders avoid

Before you touch strategy, before you change anything about your marketing, do this. One hour. A blank page. Four questions.

What’s actually working right now, and how do I know?

Not what you’re doing. What’s working. There’s a difference, and most founders can’t answer it with specifics.

“Working” has a real definition: it produces revenue, a measurable input to revenue, or it reduces what you’re spending to acquire revenue. Everything else is activity. If you can’t name what’s working and point to the evidence, that’s a starting point.

What am I doing out of habit, guilt, or optimism that I should stop?

Every business carries weight it doesn’t need. A service line that never quite worked. A customer segment that costs more than it pays. A channel somebody told you to be on 3 years ago.

The honest answer is almost always 3 to 5 specific things. Naming them is the hard part. Stopping them is what creates room for real growth.

Where is my business actually making money, and where am I pretending it does?

This one requires looking at revenue by segment, by service, by customer, with gross margin attached. Most founders have a story about their business that’s drifted from the numbers. The numbers don’t drift.

I’ve seen this pattern enough times that I look for it now. The founder thinks they run a 3-service-line firm. The numbers say they run a single-service-line firm with 2 expensive hobbies attached.

Who am I as a founder, and what do I want this business to give me?

This is the question most marketing work completely skips. Growth is one possible goal. Some founders want a business that supports a specific life. Some want an exit. And those are different businesses with entirely different marketing systems.

If you don’t know which one you’re building, no strategy can serve you. It’ll always optimize toward the wrong target.

What the Founder Portrait actually does

These 4 questions together produce what I call the Founder Portrait. It’s not a document you share or hand off. It’s the ground you stand on when you do the strategic work that comes next.

Without it, every downstream decision is made from an unstable position. The messaging, the ideal client definition, the channels, the campaigns: all of it inherits whatever you were confused about when you built it.

You can only build a system on what you actually know. The Founder Portrait is how you find out.

One thing to do this week

Sit down for one hour with a blank page and answer the 4 questions. No team. No advisors. No AI. Just you and the page.

Don’t try to turn the answers into a plan yet. The work this week is to see the business clearly. Everything else comes after that.

---

The Founder Portrait is the starting point. The rest of the system is what comes next. I’ve put the complete framework in a new ebook: “7 Steps to Small Business Marketing Success.” It covers everything from defining your ideal client to building a referral engine that actually runs. Grab it at dtm.world/7steps.

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Why the Smartest Leader Usually Fails

Why the Smartest Leader Usually Fails written by John Jantsch read more at Duct Tape Marketing

Catch the full episode:

Overview

Most companies hit a ceiling not because of strategy or market conditions, but because the leader is still trying to be the smartest person in the room. In this episode, John Jantsch sits down with Jason Wild, executive advisor and co-author of Genius at Scale, published by HBR Press, to make the case that the lone genius model of leadership is not just outdated. It is actively holding companies back.

Jason spent more than 20 years in senior roles at Microsoft, IBM, and Salesforce, leading projects across 40 countries. He watched brilliant people pour their careers into innovation efforts that succeeded at rates of five to fifteen percent, not because the ideas were bad, but because the conditions around those ideas were never built to support them. Genius at Scale is his answer to that problem.

This episode covers the shift from pathfinding to wayfinding, the three leadership roles that drive repeatable innovation, why most good ideas die in integration rather than ideation, and what small business owners can do right now to build a team that does not need them to be the source of every good idea.

About Jason Wild

Jason Wild is an executive advisor, co-founder of Wild Innovation Consulting, and co-author of Genius at Scale: How Great Leaders Drive Innovation, published by HBR Press. He spent more than two decades in senior leadership roles at IBM, Microsoft, and Salesforce and has led projects in 40 countries. Earlier in his career he had television and film credits, including a co-starring role opposite Mr. T in a CBS movie. Learn more at geniusatscale.com.

Key Takeaways

• Stop hiring for the A player. Build the A team. The distinction sounds small but it changes everything about how you lead, hire, and structure work.
• Innovation is a social process. You cannot mandate it. You have to create the conditions where people feel safe enough and inspired enough to want to co-create the future with you.
• Most innovation stalls at integration, not ideation. Good ideas are not the bottleneck. Getting them through the seams between people, systems, and teams is where everything falls apart.
• Language shapes culture more than most leaders realize. The Pfizer VP who banned the word change and replaced it with evolve saw an immediate shift in how his skeptical team responded to new initiatives.
• The most dangerous place to make decisions is your office. Getting out and experiencing what your customers actually experience is not a nice-to-have. It is a leadership practice.
• Celebrating individual achievement sends the wrong signal. If you want collaboration to be the norm, recognize teams, not heroes.
• Wayfinding is replacing pathfinding. In a world changing this fast, the job of a leader is not to set a fixed destination and remove barriers. It is to figure out where you are going while you are already moving.
• Self-awareness is an underrated leadership skill. How you make people feel when you give feedback shapes whether they will ever bring you their best thinking again.
• Small business owners are better positioned for this than they think. Smaller teams, less bureaucracy, and closer proximity to customers are advantages in building cultures of repeatable innovation.

Timestamps

[00:02] Opening hook: the reason your company hits a ceiling might have nothing to do with strategy.

[00:53] Jason’s first career in Hollywood and co-starring with Mr. T in a CBS movie of the week.

[01:44] The core premise: why the lone genius model of leadership fails and what replaces it.

[03:33] What Jason saw at IBM that shaped his thinking about why smart people accept such low innovation success rates.

[06:37] Why small business founders are wired to be the genius in the room and why that eventually becomes the ceiling.

[07:19] The ABC framework: architect, bridger, and catalyst unpacked.

[10:07] Why the architect role is really about culture and psychological safety.

[11:03] The bridger as the unsung hero of innovation and why Death Valley is where most good ideas go to die.

[13:04] The role outside consultants and third parties play in bridging across boundaries.

[14:03] What catalysts do differently and how movements start with people and ideas, not companies.

[16:35] The Pfizer story: how banning the word change helped get a vaccine out in 266 days instead of eight to ten years.

[18:25] What we typically celebrate about leadership that the research says is actually wrong.

[20:31] How writing the book as a collaborative team proved its own thesis.

Memorable Quotes

“Stop trying to hire the A player. Focus on building the A team. It sounds subtle but it is a fundamentally different way to lead.”

“Innovation is not about coming up with the best idea. The organizations that innovate time and time again focus on the conditions and the environment around the idea.”

“Most innovation stalls not at the ideation phase but the integration phase. That is where good ideas go off to die.”

“Self-awareness is one of the most undervalued skills in leadership. How you make people feel when you give them feedback determines whether they will ever bring you their real thinking.”

“If the billionaire founder can make time to stand in line at a bank branch, everyone else can practice empathy too.”

---

Learn more at geniusatscale.com.

Duct Tape Transcript

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John Jantsch (00:02.083)

So what if the reason your company hits a ceiling has nothing to do with strategy, funding or market conditions and everything to do with who you think the genius in the room is supposed to be? Hello and welcome to another episode of the Duct Tape Marketing Podcast. This is John Jantsch and my guest today is Jason Wilde. He's an executive advisor and co-author of a book we're going to talk about today, Genius at Scale, How Great Leaders Drive Innovation. was published by HBR Press.

Jason spent more than 20 years in senior roles at Microsoft, IBM, and Salesforce and led projects in 40 countries and co-founded Wild Innovation Consulting. And this wasn't in your bio, I don't think, but I found you had some television credits, movie credits. So can we start there?

Jason Wild (00:53.47)

We can start wherever you want, John. It's great to on your show, yes. My first career was Hollywood. My mom was the classic stage actor, stage mom, trying to get me and my brother to be famous. So yes, believe it or not.

John Jantsch (01:09.562)

That's awesome. So you started with Mr. T in something? Is that one I found maybe? Was he? Yeah.

Jason Wild (01:16.238)

I did. did. It's, yeah, going back to the eighties, but at the peak of his his fame in the 18, I did co-starred a movie was the CBS movie of week called The Toughest Man in the World that you can find on Amazon or YouTube. I think actually a few years ago, I found a YouTube clip where whoever uploaded the clips said it was the worst fight scene in Hollywood history. And I agree.

John Jantsch (01:43.081)

Well, you have that permanent record for you. All right, so let's dive into the book. The core idea is that the idea of the genius at the top, the boss, is really now out of date and what's needed now is genius at scale. Can you make that concrete really for a business owner, say, running a team of 10, 20 people?

Jason Wild (02:08.046)

Yeah, absolutely. this is a book that when my co-author invited me to write the book almost 10 years ago, I kind of thought it would be the book writing version of the Gilligan's Island, right? It'd be maybe a two, three year tour. And here we are, believe it or not, almost 10 years later and thousands and thousands of hours and worth every minute. So basic premise was I was not interested. I'm a practitioner. You know, I've been leading projects in teams.

trying to do meaningful work around technology, digital transformation, cultures of innovation around the world with large companies as well as startups. honestly, at this point in my career, John, I was not interested in just writing a book to write a book. But I was really lucky to start my career at IBM when Lou Gerstner was still CEO there and got to interact with Lou a little bit and

And it was a really important moment, I think, for me at that part of my career, because IBM was very client focused, very customer centric. And that was ingrained deeply in my brain. I was surrounded literally by geniuses. I was there when IBM did Watson on Jeopardy. I got to know the guy who invented the relational database, eventually a small company called Oracle monetized and created a nice little business around.

John Jantsch (03:30.042)

You

Jason Wild (03:33.711)

You know, as I was working on these projects, long story short, I was seeing these incredibly talented people literally pour their life into these projects or whatever it is they were working on, but accepting very low success rates, 5%, 10%, 15%. And, you know, I bought into the same notion that innovation was all about coming up with the best idea, that it was about the lone genius.

John Jantsch (03:58.329)

you

Jason Wild (04:01.672)

I'm the person with the biggest title and power. But over time, I became really curious about what really did set out in a small company or a big company. You why did some ideas, you know, go far enough along to actually change the way that we live or work or change the system? And others didn't. And it kind of became a little bit of my career and life passion. And I saw so many of these people that I really looked up to just approaching it kind of the wrong way.

falling in love with the ideas, focusing on the world of innovation. And maybe they get lucky or there's some heroic result, but the real organizations or teams that were great at innovating time and time again, were the ones that really focused more on the conditions and the environment around them. And so, we started talking about Mr. T, it took me 40 years for my life to come full circle away.

But, know, genius at scale in some ways is meant to kind of put down this notion of, you know, senior leaders stop looking to hire that A-Team player and instead focus on building an A-Team. And I think it sounds very small and subtle, but it's a big part of the difference. And then when I looked at it, there are lots of books on innovation, of course, and lots of books on leadership, but there are no books about how do you actually lead innovation.

John Jantsch (05:25.433)

Yes.

Jason Wild (05:25.486)

which to me was really really fascinating because it's one of those words or topics that lots of people lean forward, they're interested, they're curious, but there was a lot more opinions than actual science around how do you actually create those conditions as a leader for people to be willing and able to want to innovate. In my co-author's last book that was published about 12 years ago, focused a lot on companies like Pixar and eBay.

right, super creative, know, digital native companies where innovating is not easy, but it's certainly easier than being, you know, a mom and pop small company, right, or a legacy company that, you know, was founded 80 years ago. So in Geniuses Scale, the book that we wrote, we, you know, we focused on companies in regulated environments, healthcare, banking, you know, as well as startups, startups in Africa and Japan to really shine a light on, you know,

Everyone's context is different, but really the role of leaders is to create the environment where innovation organically thrives as a result of the community versus constantly trying to chase the next shiny object.

John Jantsch (06:37.322)

So, a lot of my listeners are small business owners, mid-size business owners, founders. And I think the very nature of that is like, I created this thing, I'm the genius, it starts there. And so then I'm going to build a team and everybody looks to me to continue to say, what's next? And you really introduce the evolution, I guess, that that leader needs to go through and even some roles that they need to take on. You're ABC, you've got a good, like all consultants, you have a...

a good framework there for architect, bridger, and catalyst. Walk me through a little bit of what those roles are and maybe the challenges for lot of business owners to step into those roles.

Jason Wild (07:19.446)

Yeah, no, absolutely. I think, you know, for small businesses, you know, even large businesses these days, you know, doing business in the past was, don't think it was ever easy, but it was, it was, it was easier. And, you know, and literally the world is shifting two or three feet underneath our feet, you know, every single week. So there's so much to keep up with and

Yeah, you know, so legacy leadership was, you know, some would call kind of pathfinding to your point, whether you're, you know, the owner of a small business or a 4,200, 500 company, right? And that legacy kind of leadership is change management, setting the direction, right? Articulating the vision, hopefully very, very clearly, and then convincing as many people as quickly as possible to get in the car and follow you to that, to that destination. And maybe that was okay, right? When you had the luxury of time.

But the world is changing really quickly and you could argue that it's never going to be as slow as it is right now. It's only going to accelerate. So part of what the book is about is this what we're calling wayfinding. If classic leadership was pathfinding, setting that direction and trying to remove those inhibitors and barriers, which is even more important as a small business owner because your margin of error is even less than a large company.

It's very uncomfortable for many leaders, regardless of your pedigree and your background. But I do think that small business owners are going to be more ready and in a better position to be able to pursue this. And what we talk about is more wayfinding. And part of the uncomfort is, how do you lead when we're surrounded by fog? Because it's not just artificial intelligence that's changing the world. There's geopolitical aspects, there's supply chain.

There's other technologies, quantum, 5G, blockchain, all of these things are like feeding off of each other that makes predicting the future even more difficult than it was before. So this notion of wayfinding is figuring out what the destination is while you're on the path. And to your point, we identified common patterns and three very distinct roles that leaders play.

Jason Wild (09:39.119)

in cultures that have proven that they can innovate routinely in time and time again, and not just get lucky once or in the right place at the right time. So the ABCs, which yes, are convenient and memorable, but did kind of like surface naturally, you know, out of our research and work. So first and foremost, the foundation is the architect. And the architect's job is really about building community. And what I touched on a little bit earlier,

John Jantsch (09:52.218)

you

Jason Wild (10:07.118)

it recognizes that innovation is a social process. And especially in small companies, you can't mandate innovation. You have to invite people to want to co-create the future with you. And we define innovation very broadly, not just disruptive innovation, but anything that's new and useful, which I think makes it even more applicable to the world of small business. So architects do a good job of creating environments where people are both willing and able.

to want to contribute, there's a psychological safety. They don't feel like there's going to be a negative reaction when you challenge, right, or come up with a new idea. So that's why that's the foundation. And it is, it's a lot about culture. It is totally about culture. And I think in a way where the culture is continuously learning and experimenting too. And I think especially for small business owners,

John Jantsch (10:47.064)

That sounds like culture to me.

Yeah.

Jason Wild (11:03.5)

Right, your business is not too big or too small to at least have a couple of working hypotheses. And I think that's what great architects do is they have working hypotheses and they encourage and empower others to have working hypotheses of at least one or two big questions this calendar year that we want to get smarter about. And those questions will lead us to better questions. So architect is a foundation and I think we realize that

You know, that's important, but it's not enough. And then the next one is the Bridger B. Bridger is really about focusing on building partnerships and Bridgers, you know, tend to be more junior people in the organization. And I really feel having been a practitioner and out there like doing the work, the Bridger is the unsung hero of innovation where the architects maybe get, you know, the award and the Steven Spielberg and the Oscar.

And then we'll get to the catalyst, which is about igniting movements that literally change the world. The bridgers are usually behind the scenes doing really tough work and recognize that, recognizing that most innovation stalls, not at the ideation phase of coming up with the ideas, but the integration phase, human integration, system integration, integration with partners. So these bridges are, you know, focus on these boundaries or these seams.

where lots of good ideas go off to die. And one of my previous employers actually called this area Death Valley, as if it was a place that was a badge of honor if you survived it. So great architects and bridgers kind of flip the lens and create environments where it's not about surviving Death Valley, but it's about creating conditions.

John Jantsch (12:32.09)

Yeah.

John Jantsch (12:46.03)

Well, so what role then does like outside consultants and third parties play in that too? I've said, when you talk about partnerships, you're kind of focusing on internally, but bringing in great talent from the outside is probably a part of that bridge, isn't it?

Jason Wild (13:04.994)

Yeah, it is. It can be internal and external. can be sales and marketing, business and tech, right? A lot of it is people who speak different languages, have different objectives, feel that they're part of a different community. And, but you got to get them to kind of work together. They may not want to like hang out together at the end of the day and be best friends, but you know, the role of that leader and that bridger is getting the collective value out of them that individually never would have happened. So.

Absolutely, there's a lot of focus on partnering externally. And I think what Bridges, Bridges are good at many things, but one of things that really good at John is building trust in low trust environments, being proactive at mapping the ecosystem and places where, hey, if this goes well or not well, we think we're going to need some solutions or partners here and not waiting until it's a five alarm fire. And they give credit to others and go out of their way.

John Jantsch (13:45.338)

Mm-hmm.

Jason Wild (14:03.192)

to make others the hero and not about themselves. And then C is the catalyst, C is about really igniting movements, movements that become bigger than the individuals. And I think this is where it's not every day where people wake up and say, hey, John, I want to ignite a global movement, right? Because it just seems so far away.

And, but you look, I I worked at Salesforce for many years, which is one of the CRM platforms for small business. And, you know, what's interesting about a place like Salesforce is it's become kind of the de facto movement for CRM and cloud computing. So a lot of people associate the companies with those movements, but movements are really started by people and ideas. And so part of the reason of the book is to give hope.

to people that it may seem very difficult or impossible, but anybody can ignite a movement that changes how we work and live with the right focus and other best practices that obviously we would love for you and people to read the book and learn about.

John Jantsch (15:13.478)

Well, so the ABCs basically add up to what you're saying is we need to have collective genius in order to have innovation. how do, I mean, do people resist or maybe misunderstand that idea?

Jason Wild (15:29.656)

Yeah, think there's resistance everywhere. one of the things that I think in writing the book, we wanted to write a book that is educational and inspiring, but also a business book that doesn't put you to sleep and has an element of entertainment because we're so fortunate and privileged, John, to be able to have studied for years some of these leaders and be a fly on the wall.

And one of them was the leader of clinical supply chain at Pfizer, who was a relatively new executive. And it's the story behind what he and his team did to get the vaccine out there in 266 days, in usually what would take eight to 10 years. And one of the things that they did was a real focus on language. And it's a reminder that every detail matters if you want it to.

And Michael Koo, this Pfizer VP, he inherited the team that was skeptical of almost everything, just because of past failures and attempts and other leaders and the usual stuff inside of a big company. And one of the things that Michael decided in his first few months of joining Pfizer was he banned the word change. And it sounds very petty, but...

John Jantsch (16:52.346)

Hmm.

Jason Wild (16:56.386)

I think it represents a bit of the genius of him understanding the environment that he was parachuting into. And instead he said, let's talk about evolve. Cause when people would talk about change, immediately it would be a negative reaction, more change. We went through a change management program last year. I'm tired of change, but who doesn't want to evolve, right? Who doesn't want to keep up with the Joneses? And so there was something psychological there about

You know, everyone should want to get better, better, better at their craft. And if you don't, why are you here? And I think you again have less luxury in a small business. So language matters. And I think self-awareness is one of the most undervalued skills of leadership. How you make people feel when you give them feedback.

And these soft skills now with the arrival of AI, you you hear lots of people saying they're not soft skills anymore, right? Because, you know, getting the most out of people and tapping into as Pixar would say, everyone has their slice of genius is not the responsibility of the individual worker. It's of the leader to activate that and figure out what it is individually.

John Jantsch (17:58.614)

You

John Jantsch (18:11.918)

Yeah, I'm curious because you studied so many exceptional leaders, are there things that we typically celebrate that are wrong about leadership and leadership culture that your research found?

Jason Wild (18:25.294)

Oh yeah, know lots of things. One of the things that's a pet peeve of mine is celebrating like individual awards. And I mean, even like Thomas Edison said, it's like, nobody did anything alone. And whether it's intentional or not, just putting someone up on stage as an individual, it sends their own signals of, right, be an individual hero and be like this person, right? And you'll get to lift the trophy too.

and instead recognize teams. And that might mean that sometimes you're recognizing people who, you know, aren't pulling their own weight. But the real message you're trying to send to the organization is collaboration is not optional. And even better, get great at collaboration because that's how like meaningful value creation happens. I think the second thing is, that back to stop trying to be the smartest person in the room. And instead,

try to activate that collective intelligence of the entire team. And I think the third one, and I'm not as worried about this small business, but I'll say it anyway, is what do you think is the most dangerous place to make a decision,

John Jantsch (19:39.81)

in a meeting.

Jason Wild (19:41.635)

Yeah, in the office, right? In the comfort of your office. So I'm a big believer in getting out there and walking a mile in the shoes of your customers. Do it sometimes with purpose. Do it sometimes with a blank sheet of paper. I worked at Salesforce. Mark Benioff, the founder, co-founder of Salesforce, is a billionaire. know, famously ahead of a big meeting with one of the big American banks.

John Jantsch (19:52.792)

This is

Jason Wild (20:08.77)

He wanted to go to a local branch, wait in line, to see the experience. And Yad helped him prepare for the meeting, but it was more about sending a signal to the whole organization that if the billionaire founder can care about time to do it, then everyone else can practice and develop empathy. So those are a few things off the top of my head.

John Jantsch (20:31.406)

So this book, you had a co-writer, so this book in some ways was collective genius. Do you think that that collaboration itself made for a better book or at least a different experience than writing a solo book?

Jason Wild (20:45.442)

I think so, for sure. And we're still friends, thankfully. so yeah, it's a multi-generational team. I'm in the middle. know, two academics with me as a practitioner. And yeah, I think it was just a phenomenal experience that I think we all agree that there's no way we would have ended up where we got to if we tried to do this alone.

And I think the most important thing is that, you you write a book, but you never know how the world is going to respond. And, you know, I think some of the things like wayfinding is in the epilogue. And we wanted to write a book that was meant to be timeless, because I have some friends writing books about AI. You know, one was the former chief AI officer at NASA. And like tongue in cheek, I tell them like, good luck, hopefully it's still relevant by the time it's published. And

John Jantsch (21:40.806)

Yeah, no kidding.

Jason Wild (21:42.286)

So it's interesting that we didn't write a book about AI, but a lot of people serendipitously are saying that the ABCs represent a really interesting operating system, right? Because organizations, you need some structure and predictability, but again, you need to adapt and flex and morph your value proposition like great startups do. And so I don't think we would have landed there without this,

two exceptional co-authors that I've had the privilege of working

John Jantsch (22:15.578)

Well, and I think you also surfaced in this day and age, what are probably going to be the human skills that are going to remain the most valuable, I think, in the long run as well. Well, Jason, I appreciate you taking a few moments to stop by the Duct Tape Marketing Podcast. Is there a place you'd invite people to connect with you and certainly learn more about Genius at Scale?

Jason Wild (22:35.756)

Yes, thanks for asking. yeah, it was just published a couple of months ago. We've got a wonderful website in multiple languages, genius at scale.com, genius at scale all one.

John Jantsch (22:49.144)

Awesome. Well, again, I appreciate you stopping by and hopefully we'll run into you one of these days out there on the road.

Jason Wild (22:53.977)

Sounds great. Thank you so much, John.

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The 5 Stages From Operator to Owner

The 5 Stages From Operator to Owner written by John Jantsch read more at Duct Tape Marketing

Catch the Full Episode:

Overview

Most agency founders think becoming CEO is the finish line. Jason Swenk says it is actually one of the traps. In this episode, John Jantsch sits down with Jason Swenk, founder of Agency Mastery and author of Operator to Owner, to walk through the five stages every agency founder has to climb and why so many get stuck long before they reach the top.

Jason built and sold his own digital agency after working with brands like AT&T, Hitachi, and LegalZoom. Now he works with seven and eight figure agency founders who are still doing too much, holding on too long, and wondering why the business cannot run without them. The conversation covers the identity shift required at each stage, why founders are usually the worst managers, and what it actually looks like when you finally get out of your own way.

This one is for agency owners and consultants who know the business depends on them too much and are ready to do something about it.

About Jason Swenk

Jason Swenk is the founder of Agency Mastery and host of the Smart Agency Masterclass Podcast. He built his own digital agency from scratch, working with clients including AT&T, Hitachi, and LegalZoom, before selling it. He now advises seven and eight figure agency founders on building businesses that run without them. His book, Operator to Owner, maps the five stages every agency founder must navigate to build a business they actually own. Find the book and a free diagnostic at operator2ownerrevolution.com.

Key Takeaways

• Being the CEO is not the finish line. Most founders mistake the operator or manager stage for success and never push through to genuine ownership.
• The agency owning you is a choice you keep making. You started a business to escape the nine to five and accidentally created a 24 by seven. Getting out requires an intentional identity shift, not just better systems.
• Founders are usually terrible managers. Hiring people without systems, clarity, or defined outcomes is why you end up doing their work on top of your own.
• The bottleneck is almost always the founder. Until you build decision-making layers that let your team act without coming to you, you are the ceiling on your own growth.
• You held on to sales too long. Almost every agency founder does. And competing with your own sales team for leads is not a strategy.
• Do not hire a salesperson before you have a system. Giving someone a quota with no context, no stories, and no process is like prompting an AI with no instructions.
• You do not have to reach owner level. Architect is a legitimate destination. Know what stage you want to reach and build toward that intentionally.
• Picking a niche takes time and that is fine. Treat it like a Vegas buffet. Try things, notice what works, and ask yourself who you would serve on a performance-only basis.
• AI adds work before it removes it. If you do not build decision systems and layers first, AI will amplify your bottleneck, not eliminate it.

Timestamps

[00:01] Opening hook: being CEO of your agency might be the trap you mistook for the finish line.

[00:40] The moment Jason’s wife told him to shut the agency down and get a job, and the two questions from a NASCAR interview that changed everything.

[02:25] The five stages: operator, manager, architect, CEO, and owner, and why most founders stall in the first two.

[04:24] The rubber band effect: why founders sabotage their own teams to feel important again.

[06:20] What the agency actually needs from you at each stage changes. Most founders never update their job description.

[08:29] Why hiring a salesperson never works until you have systems and stories behind them.

[11:34] Throwing your team into the deep end without floaties, and why fender benders are acceptable but train wrecks are not.

[13:34] The E-Myth reference and why most agency owners start a business to be free and end up less free than before.

[14:08] The niche question: why forcing a niche too early backfires and how to find the right one over time.

[16:11] What a true owner’s week actually looks like day to day.

[17:52] The one thing Jason held on to too long and what finally changed when he let it go.

[19:46] One move agency owners can make in the next 30 days based on which stage they are in right now.

Memorable Quotes

“We start an agency to leave the nine to five and end up starting a 24 by seven. It does not make any sense.”

“It is not about who you need to hire. It is about who you need to become.”

“If you are not evolving, you are not doing anything. Especially now, more than ever.”

“I held on to sales too long. I was even competing with my own sales team, which is completely unfair.”

“If you had to be paid on performance only, who would you do it for and what would you do for them? That is how you find your niche.”

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