The Power of Niching Down, Adding Instant Value, and Vulnerability in Content Creation

Callan Harrington 0:00

The big win was that I finally made the decision to 100% focus on insurance and niche down. You’re going to attract more of the right clients and repel more of the wrong ones. That doesn’t mean you won’t still get some people outside of that niche, but you’ll grow faster as a result. It was a hard decision for me to make.

You’re listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out the key insights that led to their success. I’m your host, Callan Harrington, founder of Flashgrowth, and I couldn’t be more excited that you’re here.

Callan Harrington 0:30

Sullivan, welcome back to the show.

Sullivan Finlay 0:33

It’s good to be back! It’s been a minute. August of last year was the last time we recorded—whoa.

Callan Harrington 0:41

That’s actually shocking.

Sullivan Finlay 0:43

Yeah, that’s multiple quarters.

Callan Harrington 0:46

You assess that in quarters, huh?

Sullivan Finlay 0:48

I mean, it’s probably our core audience—people who think in quarters, not days or weeks.

Callan Harrington 0:54

Thirteen weeks at a time, 100%. Alright, let’s kick this off with “Hot Off the Press.” So, DeepSeek—the Chinese AI company—is everywhere. You can’t miss it. I haven’t messed with it yet, but I want to check it out. They’re talking about how AI could rapidly decrease the time until knowledge workers are no longer needed, and humans will just focus on living their lives. If you had said that a few years ago, it would’ve sounded insane. Now? It’s kind of interesting and also scary. Work and career have been such a big part of my life—what does it look like when that’s no longer the case?

Sullivan Finlay 1:40

Has there been any talk on how quickly we could get to that point?

Callan Harrington 1:45

Everybody says “rapidly.” Every time a breakthrough happens, they say it’s coming faster. But if you ask ten different people, you get ten different answers. Is this going to be like VR? Everyone thought VR would be Ready Player One instantly. The first time I put on a VR headset, I was like, “Whoa, this is incredible! Everyone’s going to do this.” But it never really took off. I think AI is different, but I don’t know. On the one hand, it’s exciting to think about how this will impact our day-to-day work. But what does work even look like at that point? Some people will have to learn how to have fun.

Let me give you an example—at a company I was with, we were going to sell to a private equity firm. At the last minute, they pulled out. I was devastated. I had been working essentially two full-time jobs for 90 days straight. After that, we decided to wait before going back to market. So, no big growth was happening, and I went on autopilot. I picked up playing squash and got obsessed with it. I had to focus on something. If AI replaces knowledge work, I think a lot of people will turn to recreational activities like that.

Sullivan Finlay 3:20

The headline from this conversation: “Callan Harrington says this will all happen in six months.”

Callan Harrington 3:26

Six months! Six months! Anyway, yeah. What about yourself? What are you seeing out there?

Sullivan Finlay 3:30

A lot of my focus, especially being someone on social media, has been around the TikTok situation. The ban got delayed, and now there’s this bidding war over it. Major players—Microsoft, Elon Musk, Frank McCourt, Kevin O’Leary, MrBeast, Perplexity AI—they’re all interested.

The most interesting proposal I’ve seen is giving the U.S. government up to a 50% stake. That’s wild. I’ve had a theory that this would become increasingly political, and I think we saw that with Twitter when Elon bought it. Half of the country was fine with it; the other half was concerned. One key thing: the proposed sale agreement would not include the algorithm. That’s the most valuable part of TikTok. If they don’t sell that, what are buyers actually getting?

Callan Harrington 4:47

So are they just buying the user base? The value of TikTok is the algorithm. That’s why I don’t download it—I know I’ll get sucked in.

Sullivan Finlay 4:58

Yeah, 45 minutes minimum, easy. I’m curious if the government thinks there’s a difference in security between TikTok now and a version where they sell everything except the algorithm.

Callan Harrington 5:19

You have a big TikTok presence. Does this stress you out?

Sullivan Finlay 5:27

Not really. People will always want social media. If TikTok disappears, something will replace it—Instagram, YouTube Shorts, or some new platform. What does worry me is that brands are hesitating to invest in TikTok right now. They’re shifting budgets toward Instagram. That’s a double-edged sword.

Callan Harrington 6:15

Yeah, TikTok has always been interesting from a business perspective. The argument is always, “Are your buyers there?” TikTok skews younger, but I don’t think that’s the case anymore. I told a friend recently—he was making a lot of videos and putting them on LinkedIn. I asked if he’d tried TikTok. He wasn’t sure if his audience was there. I told him, “One of the great things about TikTok is that you don’t need a huge following to get distribution. If people like it, the algorithm will push it out. If they don’t, who cares? Hardly anyone will see it.”

Sullivan Finlay 6:42

Exactly. If people don’t like it, maybe five people see your video—probably four of them are your mom. A lot of people DM me saying, “I want to start creating content, but I’m scared about putting myself out there.” I always tell them, “You think people are going to care way more than they actually do. Just start.”

Callan Harrington 7:15

No one cares—except the 1-2% of trolls. And the trolls are always there.

Sullivan Finlay 7:20

Yeah, but interestingly, I’ve found that many trolls aren’t trying to be mean. They genuinely believe what they’re saying. They feel obligated to share their opinion.

Callan Harrington 7:47

Yeah, and they’re wrong.

Sullivan Finlay 7:51

Exactly. That’s important to note—if they disagree with me, they’re wrong.

Callan Harrington 7:55

That’s very clear. Alright, let’s move on to Work in Progress.

Sullivan Finlay 8:01

Sure. So, for me, I’ve been trying to launch my voiceover career as part of my broader work in comedy and acting. I’ve completed a voiceover demo, I’m reaching out to agents, and I’m trying to break into commercial work. The long-term goal is acting in animated shows, films, etc., but commercial voiceover is the first step.

Right now, if a brand wants to create a commercial, they go through an agency that works with talent. Meanwhile, in the social media space, brands go through my management company to work with me on social ads. I’m trying to merge those two areas—so instead of working with separate people for voiceover and social ads, brands could just hire me for both. It’s not how the industry typically works, but I’m trying to make it happen.

Callan Harrington 9:35

That’s interesting. I’ll share my Work in Progress because it’s kind of similar but in a totally different space. The book I’m reading right now is called Never Say Sell, and it’s all about growing business from existing clients. It sounds similar to what you’re trying to do—taking your current clients and expanding what you can offer them.

You’re already doing social ads, and now you want to add voiceover. You’re working with big brands—Delta, Gillette, etc.—but they’re so siloed that getting one department to introduce you to another can be nearly impossible. So, are you able to network within those companies? Or do you have to rely entirely on your agency?

Sullivan Finlay 10:30

It’s a joint effort between my agency and me. Some brands I’ve worked with for years—even before I had an agent—so I already have relationships there. The challenge is getting these different teams to collaborate. Maybe the best approach is starting with smaller brands that are newer to commercial advertising.

Callan Harrington 11:24

Yeah, that makes sense. At a marketing agency I worked at, we wanted to be a one-stop shop—handling everything from advertising to local marketing for individual agents. On paper, it sounded great. In practice, the big insurance carriers we worked with had separate budgets for creative, paid search, and agency marketing. Everything was divided. For you, I think starting with smaller brands—especially ones where you already have a direct relationship—could be key.

Sullivan Finlay 12:10

Yeah, exactly.

Callan Harrington 12:12

Going back to Never Say Sell—has it made you think differently about how you can expand your business?

Sullivan Finlay 12:18

Definitely. One of the biggest takeaways is how important it is to listen—for problems, for opportunities. For example, we have a client outside the insurance space who recently launched an insurance product. That’s a perfect opportunity for us, since we have so much expertise in that area. Rather than trying to sell them a full go-to-market strategy upfront, I approached it differently—offering to help fill specific gaps immediately. That way, they see our value without committing to a huge project.

Callan Harrington 13:00

That makes sense. The key is being already in with a company when they need help.

Sullivan Finlay 13:07

Exactly. It’s the same reason people go to their existing gym when they want personal training—it’s just easier than searching for a new place.

Callan Harrington 13:14

Right. But the challenge is that your main contact in a company might not introduce you to the right people—or they might not even know them. Back in the day, we called it walking the halls. Just being on-site, bumping into people in the cafeteria—that’s how you meet the decision-makers you wouldn’t have been introduced to otherwise.

Alright, let’s move on to One Win, One Loss. I’ll start with my loss. A couple of months ago, we lost a big deal—a great company, a major project, and a step up to that next level. We were in the driver’s seat, but ultimately, we didn’t win. When I looked back, I realized: We didn’t have our shit together. Years ago, at my old marketing agency, we lost a deal, and our CEO told me, “Callan, we lost that because we didn’t have our shit together.” At the time, I didn’t get it—I thought I was personally responsible. But now, I see it clearly.

There were little things—how we presented, how we approached the process—that cost us the deal. So, the win that came from this loss? I finally made the decision to fully focus on insurance. I tell people all the time—niche down, focus, don’t be everything to everyone. But I wasn’t fully following my own advice. Now, we’re 100% insurance-focused, which will help us grow faster.

Sullivan Finlay 18:34

That’s huge. Do you think those mistakes happened because you weren’t paying attention, or was it just moving too fast?

Callan Harrington 18:49

A mix of both. I was pushing to move quickly, but I should’ve slowed down and ensured we were presenting ourselves properly.

Sullivan Finlay 19:23

I’ve been thinking about time a lot lately. My win this week is that Hallie (my wife) and I did an off-site—a weekend away to reflect on our personal and professional goals. It’s been incredibly valuable to just think. Taking time to strip away distractions and focus has helped me prioritize what truly matters.

Callan Harrington 20:31

Tell me more about this retreat. Is this based on Greg McKeown’s Essentialism off-site?

Sullivan Finlay 20:36

It is! Shoutout to Greg. I’ve done a personal retreat for years—taking time at the beginning of the year to reflect on the past year and set goals for the future. It includes reading, praying, and deep thinking. This year, Hallie and I decided to do it together.

Callan Harrington 20:56

What does that look like? Do you limit tech access? Do you structure it in a certain way?

Sullivan Finlay 21:07

Yeah, so we went to Lake Geneva, just over the border in Wisconsin. Being in nature helps me think. We structured it with individual reflection time first—about three to four hours each—where we focused on our personal goals. Then, we came together for another three to four hours to discuss our goals, how we could support each other, and what we wanted to accomplish as a couple. We also talked about long-term vision—who do we want to be at the end of the year? What values do we want to embody?

Callan Harrington 21:51

That sounds awesome. I always say I want to do something like that, but I never actually do it. Alright, what about your loss?

Sullivan Finlay 22:20

I touched on it earlier—some of my worries around TikTok. Brand hesitancy has definitely been a loss. Some brands are holding back on TikTok spend because of the potential ban. Others are reallocating budgets to Instagram or YouTube Shorts. Typically, when my social media growth spikes, brand interest follows. Lately, growth has been strong, but brand deals are coming in more slowly than usual. That’s been frustrating.

Callan Harrington 23:47

Yeah, one thing about social media—no matter how good you are, in 30 years, you’re still looking for work. Is there a most stable path in this industry? Like, is podcasting more sustainable?

Sullivan Finlay 24:00

Nah, I’m just rolling with it. No, but seriously—there’s always variability. TV, film, stand-up, social media—it’s all unpredictable. The most stable thing is probably establishing a personal brand that carries across multiple platforms.

Callan Harrington 24:44

How do you manage personal finances with that uncertainty? Do you save a specific percentage?

Sullivan Finlay 24:50

Yeah, it’s really boom or bust. My team just gave me my annual marketing report, which includes a financial breakdown. You can see months where income booms and months where it busts. So, I save aggressively. I also track my business pipeline closely to ensure I have enough lined up. Hallie and I have a solid emergency fund, and I try to add multiple income streams—voiceover, merch, etc.—to keep things diversified.

Callan Harrington 25:46

I struggle with this too. 2024 was our most profitable year yet, and I’ve been debating whether to take a bonus. But I never do. I pay myself just enough to cover my living expenses, and I reinvest everything back into the business. I guess I’ve become less risk-averse over the years. Alright, last segment—Spicy Hot Takes. I had ChatGPT generate some contrarian business takes, and the first one it gave me was: “Firing your best salesperson could be the best move for your company’s growth.”

Sullivan Finlay 26:25

If I were writing a sketch, this would be a boss who’s personally threatened by the top salesperson, so they fire them.

Callan Harrington 26:36

Right? The insecure manager move. I disagree with this take overall, but I do see a scenario where it makes sense. The issue isn’t necessarily the top salesperson—it’s how they operate. If they’re a lone wolf who doesn’t follow processes, isn’t a team player, or constantly over-promises, they can hurt long-term company growth. At one point, I had a high-performing salesperson who was toxic to the team. I kept them on for too long, and it hurt morale. When they finally left, overall team performance went up. So no, I wouldn’t say “fire your best salesperson” as a rule, but if they’re a cultural problem, it can be the right move.

Sullivan Finlay 28:27

Yeah, temperament matters. If they’re a problem, they’re a problem—regardless of results.

Callan Harrington 28:42

Exactly. There’s another type of salesperson I call the Talented Slacker. They have all the natural ability but just don’t put in the effort. As a manager, you spend so much time trying to “motivate” them—coaching, pushing, hoping they’ll turn it around. But if they don’t want it, they won’t change. It’s a huge time sink.

Sullivan Finlay 29:41

That’s the kid in school who aces the test but gets a C in the class because they don’t do the homework.

Callan Harrington 29:56

Yep. And in sales, effort is non-negotiable. Alright, that’s a wrap. Sullivan, thanks for coming on again.

To everyone listening—if you liked this episode, leave us a review on Spotify, Apple Podcasts, or wherever you listen. We’ll see you next week!