There are some podcast conversations where you walk in expecting to talk about one thing and quickly realize there is a much bigger conversation underneath it.
That was the case when I sat down with Gary Guseinov, CEO of RealDefense, and Sean Whiteley, President of RealDefense, for an episode of The Casey Zeman Show.
On paper, there was plenty to talk about. RealDefense has become a significant player in consumer cybersecurity, privacy and device optimization. The company says it has completed six strategic acquisitions, serves more than three million customers, has access to an addressable market of roughly one billion users through its ecosystem, and currently generates approximately $150 million per year in annual partner revenue. (RealDefense)
Deloitte ranked RealDefense #406 on its 2024 Technology Fast 500, after the company posted 267% revenue growth from 2020 through 2023. (Deloitte)
And the growth hasn’t gone unnoticed since then. In 2026, RealDefense announced that it had been ranked #129 on the Inc. Regionals: Pacific list of fast-growing private companies. (RealDefense)
But before we got into any of that, there was a much more personal reason I was excited about the conversation.
A New Baby, an Old Webinar Company and a Very Small World
I’d recently had the chance to spend some time with Gary at his home. And while Gary has spent decades building companies, making acquisitions and allocating capital, at the time we recorded the episode he had recently taken on a very different title:
Dad. Gary and his family had welcomed a baby girl, and it was fun seeing him in this completely new chapter of his life. We got to celebrate that for a moment before diving into EBITDA, customer acquisition costs, and artificial intelligence.
I think those things matter. It’s easy to look at successful founders through the lens of businesses, exits, revenue numbers, and LinkedIn profiles. But we’re all moving through different seasons at the same time. Someone can be thinking about a multimillion-dollar acquisition in one conversation and thinking about diapers and sleep schedules in the next.
There was another coincidence that made the conversation particularly interesting for me.
Gary and Sean had previously been involved with Business Hangouts—not Google Hangouts itself, but a webinar and streaming platform from the Google Hangouts era.
Gary had acquired the business, Sean became involved, and they used that relatively small acquisition as one of the places where they began developing the acquisition and operating playbook they would use later. Sean estimated during our conversation that they ultimately created roughly four times the value from that investment before moving on to additional acquisitions.
Naturally, the webinar connection caught my attention. I’ve spent the better part of my career in this industry through EasyWebinar. Then the world got even smaller.
As we talked, we realized that Gary and I had both worked with the same person at different points in our careers. Not at the same time. Not even in the same era.
Someone who had worked in their world years earlier eventually ended up working with me at EasyWebinar. There was something funny about that.
Different companies. Different years. Different paths. And somehow webinars had connected all of us. But there’s also a deeper reason that connection interested me.
Gary and Sean understand something about webinars that many people who have never operated in the space don’t immediately appreciate. A great webinar isn’t simply a digital presentation.
It is a belief-building environment.
I’ve sometimes described this as story indoctrination—not in the manipulative sense of the word, but in the sense that you are giving someone enough context, education and narrative to begin seeing a problem through a different lens.
A strong webinar takes someone through a progression:
Here is the problem.
Here is why the problem exists.
Here is what you may have misunderstood.
Here is what is possible.
Here is a different mechanism for solving it.
Here is the evidence.
And now, here is the decision in front of you.
That process is increasingly important in a world where information itself is becoming commoditized.
People don’t need another 15-second piece of content telling them what to think. They need context. They need someone to connect the dots. They need enough time with an idea to actually understand it. And interestingly, that same concept—understanding the story underneath the numbers—kept resurfacing throughout my conversation with Gary and Sean.
These Aren’t Theoretical Operators
Before getting into the lessons, it’s worth understanding the experience sitting on the other side of the conversation. Gary’s history in cybersecurity goes back more than two decades.
He originally founded the business that became CyberDefender in the early 2000s. According to a case study from RealDefense financing partner Sunflower Bank, CyberDefender went from essentially zero to approximately $70 million in revenue in roughly five years before Gary ultimately took the company public on Nasdaq. (Sunflower Bank)
Years later, after the company had changed hands and declined, Gary came back. In 2017, he assembled a group that included Sean, Corbel Capital Partners and Broadstream Capital Partners and bought the business back, rebuilt it as RealDefense and returned it to profitable growth. (Sunflower Bank)
Since then, RealDefense has used acquisitions as an important piece of its model, adding businesses and brands including USTechSupport, iolo, STOPzilla, SUPERAntiSpyware and Support.com. (RealDefense)
In a March 2026 interview with SaaS entrepreneur and interviewer Nathan Latka, Gary said RealDefense finished 2025 with roughly $60–70 million in top-line revenue and $20–25 million in EBITDA, with approximately 300 people supporting the business. Those figures were self-reported by Gary in that interview, but they provide a useful sense of the scale at which he and Sean are now operating. (Latka)
Sean brings a different but equally impressive operating résumé. Before RealDefense, he served as COO of Cargomatic and TigerText, Vice President of Operations at News Corp’s Slingshot Labs, CEO and co-founder of RealtyTracker, which was acquired by Guthy-Renker, and Vice President of Operations at Xdrive Technologies, which was acquired by AOL. (Marine Electronics)
So when Gary and Sean talk about moving from startup mode into mature operating discipline, they’re not describing something they read in a management book. They’ve lived it repeatedly. And several ideas from our conversation stood out.
1. Growth Doesn’t Eliminate Risk. It Multiplies It.
Founders tend to imagine scale as the point where the business finally gets easier. Gary sees almost the opposite.
As a business grows, different categories of risk begin compounding. Infrastructure risk. Fraud risk. Competitive risk. Pricing risk. Fulfillment risk. Marketing risk. Organizational risk.
There isn’t some magical revenue number where those disappear. In fact, as Gary put it, the bigger you become, the more relevant those risks become.
The job changes from simply reacting to problems to conditioning the organization to recognize what might be around the corner. That is a very different type of entrepreneurship.
At the beginning, founders often win because they are willing to move faster than everyone else. At scale, you also have to learn how to see farther than everyone else.
2. Eventually, CAC Comes for Everyone
Gary then moved into one of the most important pieces of business math in the entire episode.
Customer acquisition costs tend to rise as you scale. Your first customer is not necessarily as expensive to acquire as your 100,000th customer.
Early in a market, you may capture people with the greatest urgency, strongest product awareness, or highest willingness to act.
As you expand, you begin reaching customers who require more convincing. Meanwhile, competitors are entering auctions for the same clicks, impressions and audiences.
That puts upward pressure on CAC. And that means your business model has to be designed to survive it.
Gary’s argument was that companies need elasticity in their monetization.
If your entire business depends on selling one $29 product, but eventually it costs $70, $90 or $120 to acquire a new customer, the math will begin working against you. Instead, the strongest businesses create multiple ways to increase the economic value of a customer.
Maybe there is a $29 entry product. Then a $50 product. Then $100. $500. $1,000. Or perhaps recurring revenue, higher-tier plans, services, cross-sells and additional solutions increase lifetime value over time.
The specific prices aren’t the point.The spread is. Your monetization has to create enough room for customer acquisition costs to increase without destroying the economics of the business.
This is especially relevant to anyone in the EasyWebinar world. We can become obsessed with metrics such as: cost per webinar registration, show-up rate, conversion rate, cost per booked call, and front-end ROAS. Those metrics absolutely matter.
But none of them independently tell you whether you have a great business.
The larger question is:
How much economic value can you responsibly create from every customer you acquire?
Because in most competitive markets, one of the strongest advantages belongs to the company that can afford to spend more to acquire the right customer—and still remain profitable.
3. The Bigger the Spend, the Deeper the Data Has to Go
Sean made a related point that I thought was particularly important.
In a small company, your analytics can sometimes be relatively crude.
You spend $10,000. Customers come in. You look at the resulting revenue. The math works. Great. But increase that spend dramatically and suddenly the question isn’t simply:
Did the campaign work?
You have to know:
- Why did it work?
- Where did the best customers come from?
- Which keywords create the highest-LTV customers?
- Which acquisition sources result in the lowest churn?
- Which customers subsequently purchase other products?
- Which media sources appear profitable initially but fall apart six months later?
Sean said RealDefense had increased its online media spend by roughly three times over the prior year leading into our conversation.
At that scale, averages can hide expensive mistakes. RealDefense therefore has to know much more precisely which traffic sources, keywords, channels and customers are generating the economic outcomes the company wants.
I think this represents an important transition every founder eventually has to make.
At one level, data tells you whether something is working. At the next level, data tells you what specifically is working, why it is working and whether you can safely do more of it.
That’s a much more sophisticated question.
4. AI Isn’t the Strategy. The Process Is.
This led into AI.
And this was probably the portion of the conversation most relevant to where businesses are right now.
There is an enormous difference between telling your company:
“Everybody needs to start using AI.” And actually developing an AI strategy. Gary used the example of a marketing department. You might already have a media buyer. A copywriter. A designer. A content creator. Someone handling compliance. An analyst. Simply handing all of them Claude or ChatGPT and telling them to “become more efficient” doesn’t redesign the system.
Gary’s approach is to first examine the existing process, then identify where AI can create new leverage inside it.
For example, suppose you have an advertisement that’s working. Traditionally, a marketing team might create five or ten variations.
AI potentially gives you the ability to generate hundreds or thousands of highly specific variations targeted toward narrow demographics, psychographics, problems or use cases.
The human strategist is still there. The media buyer is still there. The judgment is still there.
But the volume of testing that person can intelligently manage expands dramatically. The same applies to competitive research.
Instead of simply asking AI to “write me a landing page,” you might ask it to analyze a market, identify messaging gaps across competitors, map those gaps against a specific customer profile, help develop variations and then allow humans to make the strategic choices.
That’s a very different use of AI.
The goal isn’t:
Do the same mediocre work faster.
It is:
Make previously impractical levels of analysis, personalization, iteration and testing economically possible.
Gary gave another example that stayed with me. If a skilled media buyer can responsibly manage $10,000 a day today, what happens if AI-assisted systems allow that same person to intelligently manage $100,000—or potentially far more?
That’s not merely productivity. That’s leverage. And I believe that distinction is going to separate companies that truly benefit from AI from companies that simply accumulate more AI subscriptions.
5. AI Doesn’t Remove Humans. It Changes What Humans Are Capable Of.
Gary also pushed back on the idea that we’re already at the point where businesses can simply hand entire departments over to AI. We’re not.
In his words, you can’t simply say, in effect, “AI, handle it,” and walk away. AI today is a new category of tools with extraordinary access to data and extraordinary capabilities in particular areas. But tools still require architecture. They require judgment.
They require someone to understand what result the business is actually trying to create. This is something I have been thinking about a lot with EasyWebinar as we move more deeply into becoming an AI-first platform.
AI should eliminate friction. It should shorten the gap between an idea and execution. It should help a business build webinar assets, analyze data, create campaigns, repurpose content, respond intelligently to customers and uncover things humans might miss.
But mastery still matters.
AI plus someone who doesn’t understand marketing is not automatically great marketing. AI plus someone who deeply understands persuasion, customer psychology, unit economics and strategy can be something altogether different.
That combination is where I think the real opportunity lives.
6. What Makes You Fast at $1 Million Can Make You Reckless at $50 Million
I asked Sean how they balance planning with execution. His answer was essentially: That’s a company-size question.
When Gary and Sean were sitting together in a room building a smaller company, one could yell an idea across the room to the other and they could try it. There was almost no organizational cost.
That’s one of the superpowers of a small company. But as an organization grows, every new idea consumes resources.
- Engineering time.
- Design time.
- Management attention.
- Media spend.
- Product resources.
- Legal resources.
- Capital.
- Opportunity cost.
Suddenly, moving quickly isn’t free anymore. Sean described the shift as becoming much more “measure twice, cut once.”
At RealDefense’s current scale, initiatives need a thesis. They evaluate expected economic outcomes. They look at level of effort. They compare the opportunity against other projects competing for the same resources.
Gary said they now plan roughly a year ahead while measuring performance daily and conducting more formal reporting monthly and quarterly. That inevitably requires saying no more often.
I told them during our conversation that I’ve watched entrepreneurs build what I call half-built bridges. They get excited about an idea and start building a bridge. Then another opportunity appears. So they begin another bridge. Then another.
Eventually there are five bridges under construction, enormous resources have been spent, and none of them have reached the other side. Mature companies still generate ideas. They just become much better at deciding which bridges actually deserve to be finished.
7. AI May Make Original Thinking More Valuable, Not Less
One of Gary’s most provocative ideas involved what happens when everybody eventually has access to similar AI capabilities.
AI is extraordinary at analyzing patterns. It can study what exists. It can synthesize enormous amounts of information. It can discover relationships between things humans might never have had enough time to analyze. But much of that is still based upon what already exists.
Gary believes this could make asymmetrical thinking increasingly valuable.
If every competitor uses similar models to analyze the same Google Ads, the same competitors, the same Meta campaigns and the same market data, eventually a lot of “best practices” begin converging. That creates an opportunity for people willing to look where everyone else isn’t looking.
Maybe that’s a marketing channel everyone has ignored.
- Maybe it’s offline advertising.
- Partnerships.
- Events.
- Direct mail.
- A media property.
- A community.
- A strange creative concept.
- A new distribution model.
- A strategic acquisition.
- Or an offer structure that doesn’t look anything like what the rest of the category is doing.
In a world where competent execution becomes easier to produce, different thinking becomes harder to commoditize. That’s a fascinating consequence of AI that isn’t discussed enough.
8. The Best Growth Opportunity Might Already Be Inside Your Business
The best story of the entire episode came near the end.
Gary and Sean had acquired another company. After closing the transaction, Gary began reviewing some of the contracts more carefully. He discovered an agreement with a major partner.
The contract was already signed. The relationship already existed. The opportunity was sitting there. But very little was happening with it. Gary asked the team why. Essentially, it hadn’t been made a priority. So he made it one. What happened next is remarkable.
According to Gary, revenue from the relationship went from essentially zero to around $50,000 in a month. Then approximately $300,000. Eventually, it reached roughly $1.5 million per month.
Stop and think about that. They didn’t invent a new product. They didn’t discover a new ad platform. They didn’t need a new funnel. They didn’t need to manufacture demand out of thin air. The asset was already there.
Someone simply had to recognize its potential and execute. Sean added an interesting detail.
Their original plan had actually been to shut that B2B2C side of the acquired business down because it wasn’t producing enough value.
Gary wanted to look more closely at the contracts first. That decision ultimately helped reveal what would become a major area of RealDefense’s business.
Today, partnerships aren’t an experiment for RealDefense. They’re one of the central growth engines of the company. In May 2025, RealDefense announced that its Partner Program had surpassed $100 million in annual recurring revenue for partners. Its current corporate site now reports approximately $150 million per year in annual partner revenue. (RealDefense)
That’s a pretty extraordinary evolution from a contract somebody almost ignored.
9. Distribution Can Be More Valuable Than Another Product
This part of the conversation hit home for me personally.
Partnership growth was one of the most important things that allowed me to scale EasyWebinar.
Entrepreneurs tend to ask:
How do I get more customers?
But another powerful question is:
Who already has the customers I want?
Those are fundamentally different questions.
The first forces you to acquire customers individually.
The second allows you to potentially acquire distribution.
That might mean:
- strategic affiliates,
- software companies,
- integration partners,
- creators,
- associations,
- consultants,
- agencies,
- communities,
- enterprise relationships,
- or another company whose customer base naturally overlaps with yours.
For RealDefense, that model now includes embedded partnerships with software companies, cybersecurity platforms, telecom providers, OEMs and other organizations. The company says its current ecosystem offers access to an addressable market approaching one billion users. (RealDefense)
That’s leverage. And there is an important connection here back to webinars. Because a partner can give you access to an audience. But access alone doesn’t necessarily make people buy. You still have to create belief. You still have to educate. You still have to tell the story. You still have to move someone from:
“I don’t know why I need this”
to:
“I understand the problem, I understand this solution, and I want to move forward.”
Distribution gets you in front of the room. Story converts the room. That’s why I’ve always believed webinars become particularly powerful when combined with partnerships.
10. Sometimes the Next Stage of Growth Requires a Different Version of the Founder
There was another conversation I wanted to have with Gary and Sean that we simply didn’t have enough time to fully explore.
And I’m hoping we’ll get into it next time. How did they have to change?
Because this is something we don’t talk about enough. We talk endlessly about product-market fit. Channel-market fit. Hiring. AI. Sales. Funnels. Capital.
But sometimes the biggest constraint in a growing company is that the person running it is still behaving like the person who ran the much smaller version of it.
The founder who succeeds through improvisation eventually has to learn planning. The founder who touches everything eventually has to delegate. The founder who says yes to everything eventually has to become exceptionally good at saying no. The founder who used instinct to understand ten customers eventually needs systems to understand ten thousand.
Early entrepreneurship rewards motion. Mature entrepreneurship increasingly rewards judgment. That’s an entirely different muscle.
What I Took Away From Gary and Sean
The more I thought about our conversation, the more I realized there wasn’t one single “growth hack” buried inside it.
There was something much more useful. A picture of what mature scale actually looks like.
- You need a product people want. But then your unit economics have to support increasingly expensive acquisition. You need data. But the sophistication of your measurement has to increase with the amount of capital you’re deploying.
- You need AI. But AI needs to be inserted into intelligently designed processes instead of becoming a substitute for strategy.
- You need speed. But eventually speed without prioritization becomes expensive chaos. You need marketing channels.But sometimes your greatest opportunity lies outside the same four platforms everyone else is using.
- You need new customers. But sometimes the fastest path to them is a partner who already has them.
- And you need creativity. Because as AI makes average execution increasingly available to everyone, the companies willing to think asymmetrically may create the biggest advantages.
There is also one final point I keep coming back to. Gary discovered a relationship inside an acquired company that eventually generated roughly $1.5 million a month.
The opportunity was already there. Nobody had prioritized it. I suspect there are far more businesses sitting on opportunities like that than we realize.
Maybe it isn’t a multimillion-dollar enterprise agreement. Maybe it’s 2,000 old customers nobody has spoken to in three years. Maybe it’s an affiliate relationship that was never developed. Maybe it’s a webinar that worked once and was never turned evergreen. Maybe it’s intellectual property buried inside your business.Maybe it’s a customer segment you’re ignoring. Maybe it’s an offer that should have another tier. Maybe it’s a piece of technology that could become an entirely different product. Maybe it’s simply a relationship you haven’t called.
Before asking what you need to build next, it might be worth asking: What have we already built that we haven’t fully valued yet?
That may be the biggest lesson I took from my conversation with Gary Guseinov and Sean Whiteley.
RealDefense hasn’t grown simply because Gary and Sean learned how to acquire companies.
They’ve learned how to see value inside assets other people underestimate—and then build the operating discipline required to unlock it.
Technology accelerates that. AI amplifies it. Capital increases its reach. Partnerships multiply it. Webinars and storytelling help communicate it.
But none of those things replace the underlying skill. The real competitive advantage is learning to see opportunity clearly—and then having the discipline to actually execute on it.
