The Power of Improv, AI-Driven Content, and Buying Back Time for Growth

Sullivan Finlay 0:00
Even when it’s a sketch that you think, “Oh, this is so dumb, we could never do this as written,” there’s usually a nugget of something, some kernel of an idea where you’re like, “Okay, that’s what this is. The premise is fun, or this angle on it is fun.” And then, that’s where you can kind of still come from the mindset of, “This is so dumb,” and then it ends up being really funny and fun to—

Callan Harrington 0:23
You’re listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items 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.

Sullivan Finlay 0:42
All right, boys and girls, ladies and germs, we are back. We’re back.

Callan Harrington 0:47
Hot off the press. We’ll start this here. Unfortunately, like every single one of these, it’s AI-related. Crowd goes wild. “Oh, more AI, that’s just what I wanted." So, in the Pavilion newsletter, they had a big topic they called the “AI Shakeup.” And there were some interesting things they noted in there that caught me off guard a little bit. One of them—I think this came from a SparkToro study—said that more than 60% of search queries on Google now result in no website visit at all.

It’s because when you’re searching, you’re looking at what the AI says in the quick AI summary before the search results. And the way that I’m thinking about this is, every single website is going to have a lot of content, and it’s actually going to look pretty good. In the past, that was an absolute advantage because you would rank in the search engines. But now, what this is essentially saying is that’s not going to matter. That very generalized, evergreen content—nobody’s going to care. People are just going to assume it was done by AI, even if it wasn’t. They’re just going to assume that it was. So, influence and building trust are going to be the absolute keys. And I’m curious if that will make businesses like yours become infinitely more important.

Sullivan Finlay 2:07
Kind of tapping in again, like the human element, and that you know that you can trust that this thing that’s created is coming from a real person. Yeah, same thing for me. I use the AI summary a lot more than I used to, and it’s because I feel like it’s far more reliable than it used to be. I’m not shocked by that 60% figure. Maybe the human element is what differentiates it. But I also wonder, at a certain point, do people—especially newer generations—just trust AI so much that it starts to be just what people accept and go to? And it’s not even that the human element is as important as maybe it is to older generations.

Callan Harrington 2:41
I think it’s going to drive people toward trusted sources. AI will be able to give quick answers, but when it comes to major decisions—although, I don’t know, maybe AI will only get stronger—I think it’s going to drive people more toward events, communities, things like that, where they can hear how other people are doing things, as opposed to just blindly trusting one source, that source being AI. I think it’s going to drive a heavy reliance on very unique content that can’t just be generated by AI—research studies, stuff like that. Not to say AI won’t help in crafting that, but it probably can’t generate it on its own. So anyway, what are you seeing in your world?

Sullivan Finlay 3:21
Something I saw this week was an article about corporate improv. It was really interesting to read through different instructors talking about their experience teaching corporate teams, but also teams of ministers. They even talked about an FBI crisis negotiation unit that did improv. And it was cool to hear different things like collaboration, taking yourself less seriously, being less anxious, agility, and being able to adapt to changes in your environment. In a corporate setting, I think about those things more, but also in some of these other examples. Like, they mentioned working with ministers, training them, and one of them reported taking less intensive notes on their sermons as a result, just being more conversational and natural—which congregations seemed to like.

One of the instructors taught the game First Word, Last Word to FBI negotiators. It’s basically a scene where if you say a sentence, your last word has to be the first word of my sentence. And what it taught these FBI negotiators to do is better listen to understand, not just to respond. It allowed them to be more tactical and more empathetic, and they attributed this to their improv training. It was really cool to read through and refresh myself on the different skills improv has taught me and how it affects my daily life. I’ve long said that I think everyone should take an improv class. It’s just so helpful. I find I’m a lot less stressed about things I used to be more stressed about before.

Callan Harrington 4:48
I very much agree with that. It just makes you a better leader, in my opinion, because of what you mentioned. You are more likely to listen and see, “Okay, how can we build on this?” as opposed to, “How do we shut this down?” I agree as well. The only caveat to that is you’re going to weird some people out. People are probably not going to be ready for Improv 101, right? That first class is usually the one that you’re the most uncomfortable in. But as you go to the second, third, fourth class, most of the people in there really, really enjoy it and take it seriously.

Sullivan Finlay 5:26
Yeah, and on that note, beware of how you then interact with the people around you in your daily life. When I first started taking improv five-ish years ago, I was still working in public accounting, and that is very much not an improv environment. I would have team members ask me how we should do something, and my improv brain would just think of the first answer that popped into my head. And they’d be like, “Okay, yeah, that doesn’t make any sense.” And I’d be like, “Well, you’re a bad scene partner. Not very yes, and of you.”

It changes the way you approach things in really interesting ways. A few years ago, I had a chance to teach a corporate training with our friend Lindsey Marie, and it was really cool to see a team transform. They were very engineering-heavy, so think of engineering stereotypes—more introverted, hesitant to play along. But by the end, everyone was just being bonkers and having a ton of fun with it.

Callan Harrington 6:23
It’s one of those things where you just have to get through that initial friction of the first class and keep going. It’s easy to say, “Oh, I’m not doing this,” but to your point, by the time you get to the end of it, you feel totally different about it. I think it’s a great experience. All right, moving on to Work in Progress. So, I have been reading Dan Martell’s book, Buy Back Your Time. This book has been awesome. One of the biggest challenges I’ve been having is that as this business has been growing and we’ve hit some bigger clients, it’s pulling a lot of my time into it.

Great problem to have, but I’m like, How do I prevent myself from just getting caught in the absolute weeds? This book was recommended by a couple of people, and one of the key takeaways is: hire to buy back your time first, then hire for growth. I’ve always looked at it as the exact opposite. So I’ve been working specifically on tracking my time and asking, Could someone else be doing this? Do I have to be the one doing this? And I realized that for a number of tasks, the answer is no—I don’t need to be the one doing this. And just in a couple of weeks, it has had a pretty significant impact.

Sullivan Finlay 7:34
Mine is basically copy-paste, and it’s about buying back my time as well—specifically in video editing, which I kind of teased a little bit last week. Video editing is something I’ve been reluctant to outsource because I like the control of knowing exactly why I’m cutting something, how I’m putting it together. But when I really think about it, there are videos I make that are very text-heavy. And platforms like TikTok especially reward native text, so for those kinds of videos, I probably still need to do the editing myself.

But for other things, like choosing between 20 nearly identical clips where the differences are negligible? That’s something I don’t need to spend time on. It’s kind of exciting to think about how this could unlock my time and what I could fill it with instead. I’m still in the early stages—reaching out to editors and seeing what my options are. But to your point, it’s something I don’t have to do. And I really like the framing of buying back your time first and then hiring for growth. Because I definitely used to think of it the other way around.

Callan Harrington 8:31
Was it hard to let go of because—kind of like Jerry Seinfeld—you needed to micromanage every single piece of the process to make it exactly how you wanted? Or was it more of a feeling like, If I outsource this, is this still totally mine? Because for me, it was the latter. That was the one that really bothered me, and I eventually realized that was foolish. It’s a team effort. If you look at the top comedians, content creators, or whatever, there’s always help involved. But I’m curious—what was it for you?

Sullivan Finlay 9:00
Honestly, I think it was just me making a series of excuses at different points. Early on, when I was starting to get some momentum financially, I’d ask myself, Is the cost really worth it? Then it was the control aspect—thinking, I know exactly how I want this to look because I’ve done similar videos before. And a lot of times, when I’m editing, ideas will spark in real-time about how to reorder something, cut it shorter, or tweak it. So I’d tell myself, Well, because I’m doing the editing, I can make sure it turns out exactly how I want. But now I’m realizing that the extra value I get from that level of control probably isn’t worth the time investment. What about you? When you started tracking your time, what were the first things that jumped out as obvious tasks to delegate?

Callan Harrington 9:46
Perfect segue to my first win: inbox management. I had started to pass this off a bit, but I did it in a way where Donette—my assistant, who I’d honestly say is more like my operations manager—would categorize emails using the Getting Things Done methodology.

So we had:

• Reference – Not important, just saved for later.
• Important but not urgent – Needs attention but not right away.
• Urgent – Requires immediate action.

If anything fell into the urgent category, she would send me a screenshot on Slack. That cleared out a lot of little things like calendar acceptances, declines, and minor tasks. But even with that system, I still found myself checking my inbox all the time and responding to emails all day. So I implemented something from the book called Email GPS.

Here’s how it works: we created a few different folders:

• “My Name” – Emails I personally have to respond to.
• “To Respond” – Emails she can handle.
• “Respond Later” – Emails that can wait.
• “Review” – Emails she’s unsure how to respond to, so we review them together.
• “Responded” – So I can see how she’s handling responses.
• “Waiting On” – Emails where we’re waiting for someone else to reply.
• “Receipts/Financial” – Anything finance-related.
• “Newsletters” – Things I want to read later.

And here’s the rule: I can’t check my inbox until she has processed everything into one of these folders. Now, every time something lands in “My Name,” she sends me a Slack screenshot. And the most surprising insight? There aren’t that many of those. So many of the emails I was responding to were quick, routine responses that could easily be templated. I’ve saved so much time. But even more importantly, I’m not checking my email constantly anymore.

Sullivan Finlay 12:05
That’s awesome. For my win this week, it’s pretty simple: I’ve been writing long-form sketches again, and it’s so, so fun. For Corporate Takeover, the show we talked about last week, I’ve been writing for that. I’m also collaborating on video content for social media that’s multi-character, similar to long-form stage sketches. It’s been a fun muscle to flex again because I’ve gotten used to just doing short, 30-second to one-minute sketches. So, stepping back into long-form writing—figuring out how to write for different people, leveraging their strengths, and incorporating my own style—has been a big win for me.

Callan Harrington 12:52
Oh man, and we talked about this before recording, but anyone who has written comedy knows this: When you describe your sketch as “dumb,” it’s either really good or never going to work.

Sullivan Finlay 13:12
Right! Even when you think, Oh, this is so dumb, we could never do this as written, there’s usually a nugget of something—some kernel of an idea—where you’re like, Okay, that’s the real premise. And that’s where you can still come from the mindset of, This is so dumb, but then it ends up being really funny and fun to do.

Callan Harrington 13:34
I think this applies to any kind of writing—whether it’s comedy, business content, whatever. One of the best but also most frustrating feelings is when you write an entire sketch, get to the very end, and that’s where the real idea is. You suddenly realize, Oh, this is it. This is the actual premise. Everything before this is pointless. And then you have to go back and rewrite everything around that one key insight.

Sullivan Finlay 14:17
100%. That just happened to me last week when I was collaborating on something. We were pitching ideas, going down the track of one idea, and then toward the end of the call, my collaborator says this one line. And immediately, I was like, That’s it. That’s the whole sketch. Like, that’s what I would name the sketch. That’s the core of it. It’s kind of frustrating because you realize, Oh, we need to rebuild this entire thing around that one line, but it’s also fun because you’re already excited about it.

Callan Harrington 14:18
Exactly. Because by that point, you’re already fired up, so it doesn’t feel like work. The pen doesn’t weigh 5,000 pounds anymore. All right, moving on to my loss this week. My content creation for Flashgrowth has totally hit the floor. The podcast is still going, but when it comes to posting regularly on LinkedIn and other social platforms, I’ve let it slip. I’m still getting some posts out there, so it’s not completely evaporated, but it’s nowhere near where I want it to be. And that ties back to something we talked about earlier: influence and trust are going to be the keys moving forward. Content is still important, but how you deliver it and what that content consists of is changing. So, a big goal of mine is to get my content output back to where I want it to be.

Sullivan Finlay 15:02
So, are you thinking about it through the lens of trust—like, How do I create content that makes people rely on me as a source of truth?

Callan Harrington 15:10
Yeah, in a way. Previously, I was creating all original content. I was posting big, long-form posts five to six days a week, plus a long-form newsletter. And none of it was team-curated—it was all my writing or responses to specific questions that a ghostwriter would then format into a post. But the way I’m thinking about it now is: How do I make this more scalable? For example, let’s take this podcast. We have multiple segments—why can’t each one of those segments be turned into a LinkedIn post and a video? Why can’t those same insights be repurposed into a newsletter That way, it’s still original content, but it’s structured in a way that’s easier to maintain. The other piece is research. AI can summarize existing studies, but what it can’t do is generate new research. So I’m thinking about how I can layer in unique insights—things like interviews, studies, or perspectives that AI can’t replicate. Think about the kinds of deep research reports that McKinsey or Accenture put out. I think more businesses are going to have to lean into that approach to create truly valuable content.

Sullivan Finlay 16:28
So, what I’m hearing is that we just need to generate soundbites here for LinkedIn posts. Okay, LinkedIn, here’s your soundbite. Nailed it. Big time. Crushed it.

Callan Harrington 16:35
All right, what about your loss this week?

Sullivan Finlay 16:37
My loss this week has been small issues pointing to a larger problem. I’ve had a bunch of little things pop up that, in isolation, aren’t a big deal, but together, they’ve been incredibly frustrating.

For example:

• I was working on a brand video where I needed to use their product and show it in the video. But I kept running into tech issues, which made the whole process frustrating.
• My standing desk broke at the worst possible height—somewhere between sitting and standing—so I couldn’t use it properly.

Individually, these things are whatever. But when you step back, you realize that they’re causing unnecessary frustration. And I think the root issue is that I’ve been hurrying too much. I’ve been reading a book called The Ruthless Elimination of Hurry by John Mark Comer, and it’s been eye-opening. He talks about how constantly rushing creates the perfect conditions for frustration and irritability. And I’ve definitely been feeling that. He has this line in the book: “If the results you’re getting are lousy, the odds are very good that something about the system that is your life is off-kilter.” So I’ve been trying to slow down and recognize that these little problems don’t have to derail my day.

Callan Harrington 18:01
Is this more about context switching or scheduling too much? Are you realizing you’re overloading your schedule, or is it more about jumping between too many things at once?

Sullivan Finlay 18:10
I think it’s more about switching contexts too often. For example, if I’m working on a creative project like a sketch, and then suddenly I have to switch gears to troubleshoot tech issues, it completely disrupts my flow.

Callan Harrington 18:29
Have you figured out what triggers that? For me, it was my inbox. If I checked my email before a meeting and saw an annoying email, it completely threw me off.

Sullivan Finlay 18:35
I think it’s just about better allowing myself to be interrupted without getting derailed. Going back to the improv point—it’s about agility. Being able to pivot without it ruining your focus.

Callan Harrington 18:45
All right, time for the Spicy Hot Take. We put this into ChatGPT: “Most thought leaders on LinkedIn are just unemployed people with good personal branding.” Whoa. Okay, you know what’s interesting? I feel like people expect me to agree with this, but I actually disagree. I think ChatGPT is exaggerating the “unemployed” part. If anything, people who are unemployed—especially after a layoff—are usually the most professional on LinkedIn because they’re incentivized to put their best foot forward. To me, the real group that pushes this narrative is solopreneurs. They’re the ones who lean really hard into personal branding. That said, I think there are some truly great people on LinkedIn. The key is, if you just scroll your feed, you’re going to get the engagement-driven, clickbait-style posts. So, what I do is bookmark the people whose insights I actually respect. Then I just open those tabs, read their posts, and I’m done.

Sullivan Finlay 20:19
I’m actually going to agree with ChatGPT more than disagree.

The two types of people who post on LinkedIn are:

1. The solopreneurs—the ones with titles like Founder, Disruptor, Ninja, Empath.
2. The “I create streamlined solutions” crowd—the ones whose profile pictures say “Open to Work.”

But yeah, I think ChatGPT was being extra spicy with this one.

Callan Harrington 22:56
All right, that’s a wrap! Sullivan, plug your stuff.

Sullivan Finlay 23:13
You can find me at @SoliFinlay on Instagram, TikTok, and other social platforms. More announcements soon!

Callan Harrington 23:23
Thanks for listening! Please leave a review on Apple Podcasts or Spotify, and we’ll see you next week!