The market changed, so we changed our pricing, and then we had a good quarter. That is how many CEOs tell the story of a hard decision, and it is the example Jeff Holman, host of The Breakout CEO, uses for the version that falls flat. Every fact in it can be true. It still teaches the audience almost nothing.
The sentence reports an outcome. It leaves out what a team, a board or a room of peer CEOs needs to hear: how the CEO recognized the problem, what limits shaped the response, and why the call went the way it did. That reasoning is the judgment, and the judgment is what the audience came for.
After 62 CEO conversations across 99 episodes, Jeff found that strong CEO stories follow a recurring four-stage structure. He calls it the Breakout Arc: Build, Break, Breakout and Breakthrough. His diagnosis for the stories that fall flat is short. "You might be missing a piece of your story."
The Breakout Arc is a structure for telling decision stories, not a method for making decisions. Its value is diagnostic. A stage left out means a piece of the story is missing, and the missing piece is usually the part a listener could have used.
A scaling CEO tells the same decision story many times. Jeff names the rooms: the team, investors, peers, an event audience, a podcast interview. None of those audiences lived through the decision, and every one of them needs the story to make sense without the CEO's context.
Under that pressure, the story comes out as facts and outcomes. What gets cut is the reasoning between the problem and the result, which is the part Jeff hears CEOs gloss over most often. The outcome survives the retelling. The judgment does not.
The cost accumulates. Each untold stage leaves the audience without context it needed. Peers cannot learn from the CEO's thinking because the thinking never reached them. And the CEO's own leadership shift, the change in how they now operate, goes unstated. A team hears that pricing changed. It does not hear how the CEO saw the problem or why that response won out over the others.
The Breakout Arc began as a pattern Jeff kept seeing across 62 one-on-one CEO conversations. His guests came from the US, Israel, England, Germany, Ireland, Costa Rica, Canada, France, Australia and elsewhere. Different markets and different businesses produced stories with the same underlying shape.
It also began with criticism of his own interviewing. Early on, Jeff asked friends what they thought of episodes. They liked them, but wanted more of one thing or lacked context for another. When he had AI review past episodes, the assessment was blunter: "Jeff, you didn't do enough of the build discussion. You didn't talk enough about what that CEO is building to know what went wrong and how it got fixed."
That origin shapes how the framework should be read. Jeff found the missing piece in his own interviews before he named it in anyone else's story, and he credits guests and listeners with shaping the arc as much as his own observation. He is also direct about its limits. It is not the only framework, and he expects CEOs to adapt it to their own style.
Build answers a plain question: what were you building? Jeff treats it as the necessary foundation for everything that follows. Without it, the audience has no way to judge what broke, why it mattered or whether the fix was sound.
He works through Build with two factors. The first is the business: the products, services and team, and what was actually going on inside the company at the time. The second is the leader: how the CEO got to that point, and the history that shaped how they would respond.
The discipline in this stage is selection. Jeff is explicit that the story is not about the CEO's whole background. The task is to bring in the relevant parts of the leader's history and the relevant parts of the business, enough to show what was being built. Too little context, and the break has no weight. Too much, and the story stalls before the conflict arrives.
If Build is momentum, Break is the moment that momentum stops, and it stops for a reason. The market drops out. A key team member quits. The product fails. A required FDA certification does not come through. Funding falls away. "Like whatever it was, something broke in the business."
The first factor is the obstacle itself, and Jeff's instruction is blunt: "You gotta name what the break was." He has sat through conversations where a CEO talked at length and he still had to stop and ask: "Like tell me what went wrong. What was it that went wrong?" A story that circles the problem without naming it forces the audience to guess at the stakes.
The second factor is recognition, and for peer CEOs it is often the most useful part of the story. Jeff wants to hear "how did you recognize that something was broken?" The signal can be obvious or subtle. The CEO may have caught it, a team member may have raised it, or a customer may have said plainly that something was not working.
Recognition is where a listener finds something to apply. The specific break belongs to one company. The way a CEO noticed it, and who in the organization surfaced it, is a pattern another CEO can watch for in their own business.
Breakout is not breakthrough. Jeff separates the two deliberately. Breakout is the behind-the-scenes work that may lead to a result. Breakthrough, the fourth stage, is the result itself. CEOs who jump from the break straight to the outcome skip the stage audiences most want to hear.
Breakout carries up to five factors. The first two are reflection and insights: what the CEO concluded once they saw something was wrong, and where those conclusions came from. An idea may have come from someone else, which is fine. What matters is the CEO's reaction to it, what seemed to be working, what did not, and how their own perceptions formed. Skip this, Jeff warns, and "people won't understand what you were thinking in the moment."
The third factor is constraints. "You don't have unlimited resources, you don't have unlimited time." Jeff adds emotional capacity to the list. Constraints are what make a decision story credible to other operators. They explain why the CEO did not take the textbook path, and they show the actual tradeoff the CEO was working within.
The fourth factor is the decision. "There's a moment, right, where you said, this is what we're doing." It can take several forms. The CEO announces it to the team. The CEO agrees with what investors proposed. Or, as Jeff has heard from some guests, the CEO takes a call investors do not support: "Well, that's my decision as the CEO. I'm moving forward with it." Each version tells the audience something different about where authority sat and what the CEO was willing to own.
The fifth factor is action: how the decision was implemented with the team, with customers or wherever it had to land. Decision and action are closely tied, and both build on the reflection, insights and constraints that came before.
This stage is what separates a usable story from the pricing example. A market change, a pricing change and a good quarter add up to a decision and a result. Breakout supplies what was going on in the CEO's head, what was going on around them, which factors shaped the call and how it was carried out. Jeff believes that is what CEOs come to the show both to share and to learn from their peers.
Breakout
Breakthrough is the result of the first three stages, and Jeff splits it into two factors. Not every story reaches one. Guests on the show have described stalled and failed attempts, including bankruptcy. But when a breakthrough comes, it has two dimensions.
The first is the business. Revenue grew, the customer base expanded, or the team became more unified in its culture. This is the factor CEOs rarely forget, because it is the outcome they already lead with.
The second is the leader, and Jeff argues it should not be left out. He reduces it to a single statement the CEO should be able to make about themselves: "okay, this is what I do different now." The full version runs: I used to operate one way, and having gone through this process and made this decision, I am a different leader in this specific way.
That statement is what separates a leadership story from a results recap. A revenue number tells the audience the company changed course. The leadership statement tells them the CEO did too, and it gives peers something concrete to compare against their own practice. Jeff describes the breakthrough as the point where the business has a new trajectory and the leader has one as well. Both give the story depth.
The practical use of the arc is as a check before a story is told. Take the last account you gave your board, team or investors about a hard decision. Write one sentence for each stage: what you were building, what broke and how you recognized it, how you worked through it, and what changed in the business and in you. The sentence that is hardest to write marks the piece your audience has been missing.
Each stage exposes a common gap. CEOs skip the context of what they were building. They leave the break unnamed, or name it without saying how they recognized it. They compress reflection, constraints and the decision into a single line between problem and result. And the statement of what they now do differently goes unsaid.
None of this changes the decision itself. The arc does not make a call better or worse. It determines whether the judgment behind the call reaches the people hearing about it. Whether the room is a board reviewing a hard quarter, a team being asked to follow a change in direction, or peers comparing notes, the facts establish what happened. The four stages show how the CEO thought, and that is the part an audience can carry into its own decisions.
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Jeff Holman is a CEO advisor, legal strategist, and founder of Intellectual Strategies. With years of experience guiding leaders through complex business and legal challenges, Jeff equips CEOs to scale with confidence by blending legal expertise with strategic foresight. Connect with him on LinkedIn.
Intellectual Strategies provides innovative legal solutions for CEOs and founders through its fractional legal team model. By offering proactive, integrated legal support at predictable costs, the firm helps leaders protect their businesses, manage risk, and focus on growth with confidence.
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The Breakout CEO podcast brings you inside the pivotal moments of scaling leaders. Each week, host Jeff Holman spotlights breakout stories of scaling CEOs—showing how resilience, insight, and strategy create pivotal inflection points and lasting growth.
Listen and subscribe on your favorite podcast platform:
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Want to be a guest—or know a scaling CEO with a breakout story to share? Apply directly at go.intellectualstrategies.com.
TRANSCRIPT SUMMARY:
00:00 Episode 100 and the Start of Season Five
00:29 62 CEO Conversations Reveal the Breakout Arc
02:03 Why CEOs Tell Better Stories With a Framework
03:31 Show Recap: CEO Episodes, Advisory Insights, Global Guests
07:18 From Podcast to a Community of Scaling CEOs
08:40 The Breakout CEO Awards and Why CEOs Deserve Recognition
10:16 A Missing Stage Means a Missing Piece of Your Story
11:26 Stage One, Build: Business and Leader Context
13:31 Stage Two, Break: Name It and How You Recognized It
15:36 Stage Three, Breakout: Reflection, Constraints, Decision, Action
19:09 Stage Four, Breakthrough: New Trajectory for Business and Leader
21:33 Eight Past Episodes That Illustrate Each Stage
FULL TRANSCRIPT:
Jeff Holman (00:00)
Hey everybody, welcome to episode 100 of the Breakout CEO. Can you believe we made it? 100 episodes, and here we are. So we're we just started our fifth season of the show. We basically just do seasons by quarter. You don't need to remember that, there's no quiz here. But we're in our fifth season now, and we've been doing 99 of these episodes. So today I thought I'd do something a little bit different. You're gonna get me talking about a little just about the show where we've been and where we're going.
And one of the things that I've come to understand after talking with, let's see, about sixty-two CEOs over the last ninety-nine episodes. The rest were all advisors and people who work with CEOs, but sixty-two CEOs sharing their breakout moments led me to understand what I've now come to call the breakout arc. It is the pathway that people go through, that companies go through and leaders go through to you know.
get to their breakthrough moment. And that's not always an easy path, as as you've heard in prior episodes with a lot of our CEOs describing what they've been through. But if you can get through that path, there's a break, the breakout leads to a breakthrough often. And so there's a there's a happy ending in these stories. Now, of course, not always not every story has a happy ending. And our guests have shared many of their failed attempts, their stalled attempts that
Things that have taken them through bankruptcy and and maybe worse. And and yet here they are. They're they've persevered, they've they've used their grit, they've they've pushed through, and they've found their breakout and breakthrough moments. So it's been it's what a pleasure it's been for me as the host to bring you those moments and to help share those with the audience. Now, today I'm gonna go through and it's just gonna be me on this episode. Don't get bored.
But I want to share with you the breakout arc that I've developed, that I've just realized exists with these, with these CEOs. So why am I sharing this breakout arc with everybody right now? There's really a simple, a simple answer to that. And that is, as I've talked with CEOs, I've seen that it's easier for CEOs to share their story when they have a bit of a framework. Whether you're coming onto this show to share your breakout moments, or whether you're going, you know, in front of,
Another audience, speaking at an event, talking with your team, talking with your your investors, whoever it might be, your peers, sharing your story with your peers. Like the breakout arc is just a natural flow to share with every to share your story with the people around you. Now it's not the only framework, and you can of course adapt it to your style, however that fits you. But I'm gonna I'm gonna outline what that breakout arc is in case you wanna use it. We'll get to that in a little bit. Before we do that.
I want to just review a few things with you. Like I said, we're at episode 100 now. It's a big milestone for us, but it's just the beginning. We're this is not the end, this is the beginning. This is way too much fun talking with all of our wonderful guests about the experiences that they've been on. And how blessed are we, right? To to hear their stories, to get some behind the scenes insights, emotions sometimes about where they've been. Some of those things might feel relatable to you as you're building.
And scaling your own business. So, what are we going what are we going to talk about today? Let me give you just a few things that we've done and where we're headed, and then we'll get into the breakout arc and we'll call it a day. It'll be a shorter episode, but I think you're gonna enjoy it. So let me recap a few of the things that we've done so far with the show. We've had 99 episodes, as I mentioned already. 62 of those have been CEO episodes, meaning we've had a CEO on, we've had a one-on-one conversation with them.
We've talked about their journey. We've talked about their breakout arc and where they ended up as both a company and a leader. We're so, we're so blessed to be able to have these insights and behind the scenes moments from these CEOs and grateful for them participating and sharing these so openly. So the rest of the episodes that we've had, which basically has turned into a pattern of one week a month, we have advisory insights episodes where we invite advisors, mentors, coaches,
people who work with scaling CEOs, people who share frameworks with companies that are scaling, we bring those people on and we do two or three or four episodes with the advisors to get another perspective in addition to the CEO's own perspective. In fact, it's been fun as I was looking back, not only do do we have these advisors on, but we've I've had several books sent to me by different advisors. this was Andrew Ackerman came on
Ricardo Garcia just sent this one about his new book that launched about a week ago. James Graham also just sent this. This is his OS the Freedom Point, the the Scalify OS operating system. I'm sure I'm messing that up, but go back and listen to the episode with with James Graham, the recent one, and and you can get that. So it's it's so fun to celebrate these accomplishments, the books that are being written and shared, and and to bring these advisors on. And I can't.
I can't not mention that Jim Tracy, one of our CEOs, also sent out an awesome book, Building Men. he's he's got a great episode in there too. So go and check those episodes out. maybe we'll have the the episode numbers in the show notes for you to make it easy to go link back to these episodes with these guests. Anyway, so we've done the advisor app advisory insights episodes. We've done the CEO episodes. We're now at at episode 100. And as I look back, I I just think how how fun it's been.
I've talked with guests from around the world, literally. many here in the US, of course, where I'm located, but we've talked to people in Israel, we've talked to people in England, Germany, Ireland, Costa Rica, Canada, France, Australia, and other places. I'm forgetting some, I'm sure, but we've talked to so many people around the world about their businesses and their insights and experiences. And and even then, you know, all the different cultures, all the different businesses.
And we see so many patterns that come together, like the breakout arc that I'm going to share with you here in a minute. If you haven't noticed, also we recently launched our email newsletter. If you'd like to get in on that, you know, we'll put the link in the show notes. Sign up. We sent send out a weekly recap of at least one of our episodes from the current season. And so we'd love to share that with you. Love to have you on that list. Lastly, you can also follow along on LinkedIn. I post very regularly our LinkedIn.
Podcast page for the breakout CEO is up and running. You can go catch a ton of clips of past episodes there. Hit the subscribe button if you like and follow along there. We're trying to make it easy that you can join this community, become a part of what we're building. Whether you're a CEO, an advisor, or someone who's just interested in the topic, we'd love to have you join. So go ahead, follow us, send us an email. Heck, let us know if you want to be a guest on the show and
And we've got a whole process for that. My team would love to explore the options with you. That's a little bit about where we've been. But I I don't think it's nearly as exciting as where we're going. As I think about where we're going, I'm going to share a few things with you just briefly here. But but the theme really is we we're not just a podcast. We're not just sharing a story here and there. This is a community that we're building. Now, we've got to do some more work on our end, and we'd like your involvement too on your end to help build this community. But as we as we get
Going into 2027, I'd like you to think about the types of things that you'd like to see in this community and share those with us. What we're thinking is we're gonna, we're gonna build an online community. We'll have that more details about that as we get that up and running. we're also gonna be doing some some virtual and maybe even in-person events. I've got a a good buddy Tyler who'd like me to bring a couple groups of CEOs down to
Lake Powell on his nice houseboat, if you've ever been there. It's a it's a large, large lake on the border of Utah and Arizona and we spend a week down there at times and and just hang out with good people and share good stories and good experiences. We might do something like that. So we'll have some events coming up. We'll we're gonna get those planned and announced and if you'd like to be involved in those events in any way, shoot me an email, let our team know, and we will we'll you know, we'll involve you in the process of
how we plan and and carry out those events. Another thing I'm really excited about, and we're we're putting the details of this together still, but it's gonna be an exciting award program. I mean, does anybody need more awards? No, but there's a part of me that as a as an attorney working with CEOs, like I know CEOs get a lot of both a lot of what do you call it? They get a lot of praise and they get a lot of crap from people, right?
There's there there you kind of either love or hate them a lot of times. I I look at it as CEOs are really the driving force behind a lot of the innovation, a lot of the courage, a lot of things that are positive happening in the world. And and it's a lonely place to be. So do we need more CEO awards? No. But do we do we want to recognize you for what you're doing? Absolutely. So we're gonna tie this in with the breakout arc that I'm gonna tell you about here in a minute.
just recognizing people for their breakout moments. So watch for the breakout CEO awards coming out. We'll be doing that in 2027. More details to come. If you think that you or another CEO you know should be recognized for their breakout moments, for their breakout insights, you know, just let us know and and we will of course get you involved in that too. So the theme really is community. We're looking to build a strong community of scaling CEOs
insightful, successful people who follow along and and love to hear the behind-the-scenes moments of their peers and love to share their behind-the-scenes moments with their peers. So we're really looking forward to building the breakout CEO community going forward. Let's talk now about the breakout arc. This is, of course, a framework that you can use to tell your breakout stories. You don't have to use this framework, but I think it's a really good format to think about because if you're missing a piece of this,
You might be missing a piece of your story. How do I know that? Because when I first started telling, interviewing guests and talking with CEOs about their stories, I said I asked some friends, I'm like, hey, what'd you think? And they'd be like, hey, I liked it, but I, but I wanted a little bit more of this, or or I I didn't have context for that. And so this is not just my insights, but this is feedback and from guests and from listeners saying, hey, this is this is what I would like to see, or this is what I wanted to hear in that episode.
And it all kind of culminates in this breakout arc framework that I'm going to share with you right now. Okay, there are four parts to the breakout arc framework. I'll give you the four stages of the breakout arc, and then we'll also talk about the factors that I like to think about for each stage. Then I'll give you a few of the episodes from the past 99 episodes that you might want to listen to as a good example of those stages of the breakout arc. So the four stages at a very high level are the
are build, break, breakout, break through. Again, that's build, break, breakout, and break through. Okay, let me tell you about each one of these. just at a very high level, build. What are you building? Right? This is this is the background, the the necessary context for what you're gonna tell in the rest of your story. Early on, if you go back or if you do like I did and you say AI, hey
Assess how this, how these episodes, these past episodes might have gone. A lot of those will say, Jeff, you didn't do enough of the build discussion. You didn't talk enough about what that CEO is building to know what went wrong and how it got fixed. And so the the build is just that necessary foundation. I like to think of two factors when I'm thinking of the build stage of the breakout arc. Factor number one is the business.
What in the world were you building as a business? You know, you could talk about your services, you could talk about your products, you could talk about your team, but what was going on in the business itself? That's factor number one. Factor number two of the build stage is you as a leader. What were you doing? How did you get to the point where you were? What was the history that you, you know, that you went through? Did you start selling when you were eight, like a lot of our CEOs did?
Did you have multiple jobs? Like where did you live? What was your family like? Now you don't have to bring it all in. The entire story isn't about your background, but bring in the relevant parts of your background and the relevant parts of the business background to say what was being built at the time. That's going to give you a solid foundation to grow off of as you get into what broke, what your breakout moment was, and what your breakthrough eventually was. So that's the build stage. Build.
has business and your own personal story in it to give context for the rest of the breakout arc. Now the second stage of the breakout arc is break. Now I like to think of if if stage one is building momentum, stage two is that momentum breaks. Now that momentum breaks for a reason, right? And so this the factors that I like to think of in the in the break stage of the breakout arc are number one,
you know what broke, first of all, something didn't work. You know, the maybe the market dropped out from under you. Maybe the the you know, a team member quit. Maybe the your product broke. Maybe you didn't get your your your FDA certifications that you needed. Like whatever it was, something broke in the business. You know, this is the the classic story arc conflict. You're building something, everything's going well
You know, you're the guy to do it. You're the lady that's that's brought it to life. And then boom, something stopped working. The something fell out, the funding fell away, like something didn't work. And that momentum, that building got disrupted with a break. So what was it? You gotta name what the break was. Sometimes I've I've had conversations with CEOs and we talk and talk and talk. And then I have to go back and say, Well, I don't really what I don't really know what went wrong in your business. Like tell me what went wrong. What was it that went wrong? So you gotta
Just name the break that happened. and then talk about I think it's I think it's very interesting to talk, especially for our CEO audience listening to these stories, to hear not only what went wrong, but how did you recognize that something was broken? Right. Those are sometimes the very obvious or very subtle signals that are are occurring in your business. Now maybe you noticed it, maybe a teammate member noticed it, maybe a customer pointed out to you, hey, this is not working, right? So
not only listing what broke, but how you recognize that break is a is I think a very insightful way to position yourself when you're kind of reflecting back on your own breakout story. So we've got build, we got break. The third stage of the breakout arc is breakout. Now you might think, this is where I, you know, did all these wonderful things and and my business is doing awesome now. Not yet, right? Breakout is more about the behind the scenes moment.
That might lead to the breakthrough. Breakthrough, remember, is the fourth stage of the arc, not the same as breakout. When we talk about the breakout stage, we're really talking about up to five factors here. We're talking about what was the reflection or the insights that you gained as you were sitting there saying, I gotta, you know, something's wrong. I gotta give attention to it. And how did you reflect on that moment? And what insights did you get? Those are the first two factors: reflection.
and insights. If you gloss over those, people won't understand what you were thinking in the moment. And people come to this show because they want to hear what was the CEO actually thinking? Not what, you know, it might be that someone brought an idea to you. That's fine. What was your reaction to it? What seemed like it was working? What seemed like it wasn't working? Where did you get your own, you know, perceptions of what was going on to add to the things that that were happening around you?
So reflection and insights. The next part of it and the next factor is constraints. Every business has them. Somebody you had you had a moment that broke, you reflected on it, you had all these insights, but then you got to work within your constraints. You don't have unlimited resources, you don't have unlimited time. You don't have unlimited emotional capacity. What constraints were you dealing with when you were when you were trying to come up with a way to navigate?
The issues or problems in your business. So far, we've got in the in the breakout stage, we've got the first three factors. We've got reflection, insights, and constraints. The fourth factor is decision. We want to hear what is the decision that you're making in your business. There's a moment, right, where you said, this is what we're doing. Hey, team, I've made a decision. Or the investor said this and I agree.
Or as some of our CEOs have done, I went and told the investors, they didn't really agree. And I said, Well, that's my decision as the CEO. I'm moving forward with it. So there's the decision that happens. It's a critical moment, but we can't leave out the fifth factor, which is what was the action that was taken, right? Decision and action highly related, also building off of the reflection, insights, and constraints that you have. All of that goes together to really bring, you know, the the
the life to your story, not just, hey, we were doing this and then the market changed. And so we, you know, so I decided we should change our pricing. And then we had a good quarter. So you can tell us a short story and you can give the facts of what's going on, but you really want to dig into the breakout, the what was going on in your head, what was going on around you, what you what were the factors that were influencing how you navigated that decision, how you implemented that decision.
That's what people want to hear. That's what I believe people come to this show to both share and to learn from from other CEOs that are their peers. So if you do all that, if you talk about what you're building, you talk about what broke in what you're building, and then you go through the breakout process of how you navigate that decision. The result of all that is your breakthrough, right? Eventually, maybe not every company, but eventually the company that you're working on has a breakthrough.
And that can be one of two things. The obvious one is what happened with the business. Did the revenues go up? Did the customer base increase? You know, did the team grow closer together, more culturally unified? What happened to the business to make it a breakthrough in your business? That's one factor. The other factor that I don't think you want to leave out. I think you want to add this, especially if you're coming onto this show. You want to talk about your own breakthrough as a leader. And it comes down to really one statement.
If you look back at what you went through as a leader, your your building break, breakout, and breakthrough, your breakthrough is where you would say, okay, this is what I do different now. I used to do all this other stuff, but having this experience, going through this process, making this decision, I am a different leader in this way now because I do these things differently. So the breakthrough really is in in my opinion.
The most fun to talk about when you say the business has a new trajectory. And as a leader, I have a new trajectory. And I think that those are two things that give better dimension and depth to your own story as a leader. That is, in a nutshell, the breakout arc. And I'm just going to repeat it again so it's easy to easy to have. It's what are you building? And it's building in the business and your own background as an as a leader. What building
Breaks in the business. That is, what is the actual thing that created an obstacle? What broke? What was the disruption that happened? And how did you recognize it? The third stage is the breakout. Again, that's the that's the internal insightful moment. You're reflecting, you're sharing insights or gaining insights and sharing where you got those insights from. You're dealing with the constraints in your business, you're making a decision and you're implementing that decision.
In your team with your customers or wherever that decision gets implemented. The fourth and final stage is the breakthrough, which is what's the new trajectory of your business and what's your new trajectory as a leader? It's pretty simple. I think it's very useful. And I hope that you like that. I hope that you can pull some things away from that and use as you think about how to tell your story going forward. Okay, let me give you just a couple of examples of episodes that you might want to listen to if you're interested in one of these types of.
in one of these particular stages, the build, break, breakout, or breakthrough. If you want to listen to a couple stories about the build stage, a few of our guests that did a a phenomenal job doing explaining how they built their company, listen to episodes 34 or 85. Episode 34 is Shay Levi. He's no name security, now unframe, and he raised a bunch of money. He talks about how he and his co-founder built this API security business.
And they grew it really fast in four years and it got acquired for about $500 million shortly after he left. So he does a phenomenal job talking about how he went through the build stage of the breakout art. Also, the other episode you can listen to is episode 85 with Scot Cohen with Wrap Technologies. He did a phenomenal job describing what he was building there, going into detail about the technology, the the nonviolent restraint technology that they built and the way that.
he actually does a great job across all of the stages of the the breakout arc. but but he he goes into great detail telling you how much money he put into this, how everything got started, how you know, why he was the right person for it, and and the background building up to eventually what was the rest of the breakout arc. So those the build stage again, episodes thirty four with Shai Levy and episode eighty-five with Scot Cohen. Okay, moving on to the break stage.
Here are two episodes that you might want to listen to to hear people talk about that disruption moment in their business. What actually broke and why? Episode 33 with was Keith Norris with KPI Fire. He talked about hitting a hitting a moment in his business where it was basically they were going to shut down and he had to make a decision with people on payroll and you know, money, revenue coming in, but expenses mounting and investors, you know, pressure. This was the moment.
that that broke in the business. And then he goes on to describe how he man managed to navigate that successfully. Another episode is episode seventy-nine with Vikas Sehgall. he was with HyperDart and some other companies before that. And and he talks about when the 2008 financial crisis hit and banks were failing, clients were slamming the brakes on things, and what he did in the moment that everything, if you remember 2008, everything
was breaking around him. Okay. If you want to listen to a couple episodes that describe the breakout stage really well, listen to first of all, listen to episode 48 with Michael Chaput. He's with Insight and he and he talks about how his business was going well, but s recognized that some of the some of the core values of the company weren't weren't working well. And so he describes the process of making
the uncomfortable decision to reopen and rework those values from the ground up. He saw that the strategy they were in wasn't going to work long term, even though it had been working short term. And he describes a process of of just reorienting the entire company after recognizing that flaw in in the approach. Another episode that that shows the breakout stage really well, in fact shows all the stages of the breakout arc really well is episode 99, our most recent episode right before this one.
Jared Shepard with Hypori, which he spun out of his other business, Intelligent Waves, he just describes going through that process of recognizing and realizing that there was a huge opportunity to take one technology that was meant initially meant to be a you know a subset or or a part of the other business, but realized that there were some bespoke cases, customer cases where he could.
Take this out and it was way bigger than it had originally been imagined. So we hired a CEO to run Intelligent Waves, his his original company. He spun out Hypori into its own company to pursue this larger market. Okay, the last one is the breakthrough stage. This is the this is where the business or the leader or both find that new trajectory after the breakout moment. So I'd I'd recommend that you give a listen to episode 42 with Draven McConville.
He was with Klipboard. Draven, he talks about being homeless at 18 and other things that he dealt with, but he scaled his field services software business through the whole Brexit and COVID issues and eventually sold it in 2024 to another company, to a billion dollar company. So that's, you know, talks about where he landed in his business after doing these things. The other episode that I'd recommend that you listen to for the breakthrough stage.
Is episode 77 with Fletcher Wimbush. He talks about having a business where they're building assessments and they're doing recruiting and they're building this kind of unified business all together. And then after recognizing in his in his breakout moment that this these businesses should actually be separated, by separating the businesses into their own teams, even each of them doubled revenue year over year for the next few years.
So he taught, he does a great job talking about the result of the breakout decision and implementation that he that he put in place. So, anyway, that's eight examples of episodes that you might want to listen to that give you a couple examples for each of the stages: the the build stage, the break stage, the breakout stage, and the breakthrough stage. That's it. We're gonna leave it at that for this episode. I hope you've enjoyed it. Again, sign up for our newsletter, join us on LinkedIn.
Comment, email, reach out to our team. We really want to invite you into the into the community that we're building. Love having you here. And thanks again for listening to another episode of the Breakout CEO. Be sure to follow or subscribe on your favorite podcast platform. And if you enjoy the show, a rating or a review goes a long way. Our mission is to promote the stories of breakout CEOs in scaling SaaS, e-commerce, and tech companies.
To equip peer CEOs with valuable perspectives and confidence. Thanks again for joining us on this episode of the Breakout CEO. I'm Jeff Holman, and I'll see you next time.
