LinkedIn Isn’t a Selling Platform: The Human DM System That Converts | Ep. 64 w/ Troy Hipolito

LinkedIn is loud. AI made it louder.
 So how do you cut through without becoming another copy-paste bot?

In this episode, Troy Hipolito (aka “The Not-So-Boring LinkedIn Guy”) breaks down how he built real momentum on LinkedIn — and how he used that momentum to launch a profitable SaaS without spending a dime on ads.

Troy is the founder of The Troy Agency and creator of Skoop (a personality-driven AI content + DM system designed to help people write like themselves, sell like humans, and follow up consistently).

What you’ll learn:

• Why LinkedIn is a networking platform — and how selling too early kills trust
• The “slow dating” approach to business (support → alignment → referrals)
• Troy’s video DM “sandwich formula” to increase booked, vetted meetings
• How to personalize fast (because people scan, not read novels)
• The right way to use AI: draft + structure…while humans keep the trust

Connect with Troy:
LinkedIn: https://www.linkedin.com/in/troyhipolito/
The Troy Agency: https://thetroyagency.com/
Skoop: https://www.skoopapp.com/

Host: Adam W. Barney — Transition Leadership Coach
Transition Leadership Foundation Call: https://calendly.com/adamwbarney/foundation-call-20min

Creators and Guests

Host

Adam W. Barney

Adam W. Barney helps transitioning leaders navigate career and leadership inflection points with clarity and momentum. Author of Make Your Own Glass Half Full and creator of EnergyOS. Based in Boston, fueled by family and music.

What is Is Anything Real??

Is Anything Real? is the Reality-First Leadership podcast for builder-leaders who want outcomes, not optics. Each week, Adam W. Barney sits down with founders and operators to unpack positioning, marketing, community, energy management, and influence - plus the numbers behind what actually worked.

You’ll hear: a quick Reality Check, a practical Proof Stack (inputs → actions → outcomes), and one EnergyOS habit you can run this week. Specifics over slogans; humane systems over hustle cosplay.

New episodes every Wednesday at 12:00 PM ET.

👉 Book your 20-min Exploration Call: https://calendly.com/adamwbarney/explorationplugin-20min

[00:05.4]
What if you could build a profitable SaaS without spending a dime on ads? Today's guest did exactly that, and he's about to tell us how. He's known as the "The Not-So-Boring LinkedIn Guy", the founder of the Troy agency, and the creator of Skoop, a platform powering over 300 users through personality-driven AI content and DM systems.

[00:28.7]
This is Troy Hipolito, and his story proves momentum beats marketing every time. Welcome back to "Is Anything Real?", the show where we unpack what's real in growth and what's just noise. I'm Adam W. Barney, energy coach and host, and if you've ever spent a fortune on ads and wondered what actually works, this conversation's for you.

[00:49.4]
Troy Hipolito, again, is a marketer turned SaaS founder who skipped paid ads altogether and built Skoop, an AI powered LinkedIn system that again, writes like you, sells for you, and helps you sound more human at scale. We're going to dive into how he did it and what it says about the future of real connection in B2B marketing.

[01:09.1]
Troy, welcome. Thanks a lot. And I also want to thank you for that great intro. Like I said beforehand, before we clicked on the show, send that to me because I would have to pay a writer to write it as well as you did.

[01:25.1]
So thank you for having me on this show. I appreciate the kind words, Troy. Awesome. So let's start here. You call yourself "The Not-So-Boring LinkedIn Guy". What's the origin story behind that brand and what was boring about LinkedIn that you wanted to change?

[01:41.2]
Well, previously I had a better title and my title previously I used to have a gamification company and I had a company called ISO Interactive. We did a bunch of cool work. All the agencies hired us when I used to live in Atlanta at the time, so we did a lot of Coca-Cola work.

[02:01.2]
Got pulled in from Chicago work, Xbox Mobile, Coca-Cola's enterprise website. Back then, they had all the AT&T's and Cingulars and all those different companies, and Cricket and all that. And we used to get a ton of work from all that.

[02:19.3]
And so my tagline, at the point. So I'm. Well, let me start with this way. Sure. I'm of mixed race, so, my mother's from Switzerland and my father's Filipino. Right. So at the bars, I used to say I'm the number one Swissopino game designer in the world.

[02:36.1]
And that would be my pickup line there. You know, I was much younger and a little more handsome back then. They're like, oh, really, you know. So I really love that tagline, you know, the number one Swissopino game designer in the world.

[02:52.1]
But it didn't translate when I was converting to LinkedIn, and people would not get it. It would just be too confusing. You know, the interactions are much different than, you know, in person, on the high-end restaurants and bars and social networks and all that stuff, in-person networking and all that.

[03:10.3]
And I said, you know what? I barely have a personality because I was a programmer previously and a software architect and all that stuff and designer and developer. And I said I have a lot of A traits, you know, like, I'm really not that exciting.

[03:28.4]
I'm really boring. So what if I was the "Not-So-Boring LinkedIn Guy". Flip it on his head. So, I'm totally dry as toast, you know, other than my robot dancing, so that's where the title came from. I wanted something rememberable and something that would stand out just enough and just make them smile.

[03:50.2]
If you look at my LinkedIn profile, they also have an option for your, what is it, the gender reveal thing? I don't know what it's called. Sure, the pronouns. Yeah, I call it gender reveal. And so I was like, people don't know I'm a man.

[04:09.0]
Like, you know, so what I did is I say, oh, I need to identify. I said, I'm, I said 5 foot 6. Identify as 6 foot 5. And so I put that in there as a laugh because I'm a giant in the LinkedIn world.

[04:25.7]
Although I'm five foot seven. That's actually not very tall either, but it wouldn't have flow, you know, so five foot six, identify as six foot five. And then one out of every 20 meetings, they see that, and they laugh. And so my thing is that when you're driving business, you have to have some kind of personality.

[04:46.1]
Even if you have dry humor, you should bring it out there so people can know you as an individual because they have to relate to you. And that's the story on that. And I know that led you, of course, to max out LinkedIn connections without ever spending a single dime on ads and, you know, turned a social system approach to drive your growth engine.

[05:13.0]
I didn't even know you can buy ads to add connections. I've never even heard of that. So, I guess my ignorance really helped me out to be to build relationships. Because, before I was not very good at relationships.

[05:28.5]
I saw something, I went and I got it, You know, and if I got blocked. But in real life, it's not good for business and it's not even good for dating business or dating in real life. Because let's take the real-life example of you're going out there and you find this beautiful partner, and she's everything you want physically.

[05:50.8]
There's a probability that maybe she's an awful person.

[05:58.1]
There is a purpose for slow dating. And so when you slow date in real life and slow date in businesses, you actually slow down and get to know that individual. Because you want to know is, not if you want to buy my stuff.

[06:14.1]
I want to know if I can support you or we are match in how we think. Are we on the same page? Is there something that I can really support you with? If I can't support you, I have a lot of great connections. Maybe I could help you by introducing you to someone that's an expert in that particular problem.

[06:34.2]
And so the idea of always coming with the idea of support and helping people is the key to driving a lot of those relationships. And again, a lot of times people say they go on LinkedIn and you ever get those messages saying hey, I can build you a new website?

[06:53.8]
Well, as a LinkedIn expert, I get messages all the time saying hey, I could help you with your LinkedIn. I'm like, you can help me with my LinkedIn? And they don't spend the time to even look at it. And so there's so much noise. All you got to do to differentiate yourself is personalize, take a look at the profile, engage, and be human.

[07:18.6]
Because most of the deals on on LinkedIn are high-value type situations. So. Yep. Well and I mean I think that weaves into Troy, you know, building Skoop and how you designed it to analyze the user's LinkedIn personality, you know, help generate ideas and even clone their writing voice.

[07:38.5]
I also know in that realm, instant video messages tend to convert up to six times better than text DMs. Why do you think, you know, in that realm of what you do here with Skoop, people still ignore that that as a tactic or a channel to leverage.

[07:54.1]
Oh, it's. That's the human element. So everyone is looking for the magic bullet. And that does everything and they don't have to do anything. Right? Well, if you are networking, there's the word work in networking; you actually physically have to show up and engage.

[08:13.2]
And for some people it's easier than others, but you have to put your best foot forward. So it's like, let's just use this analogy. Say there was this red button, big old red button that was stuck to the wall, right? Yep. And I said in order to be successful in business, at 8:00am, all you have to do is click the red button.

[08:36.8]
And then this is excuses that you will hear from a lot of these so-called entrepreneurs. I don't know, I don't think my arm reaches that far. The red is a little off. I'm not sure about the button. I don't think I can click the button hard enough.

[08:55.3]
So you get a lot of excuses because people don't want to really build a relationship. They want to sell stuff. Right. And LinkedIn is not a selling platform, it's a networking platform. So instead of trying to sell, you need to create a buying environment.

[09:15.6]
And part of that buying environment is building relationships. So say I build out LinkedIn and sales systems. That's my main part of my business. Right. And if someone comes to me with the problem, I'm not gonna sell them my service if they ask me how much it costs.

[09:35.9]
And that's a different thing. But usually it depends on what they need. My only job is to get to know them and solve their immediate pain. And so if my program's up here and they just need this type of help, let me help them where they're at.

[09:55.1]
So, meet them where they're at. Because there's having a good meeting. Of course, you want to have the right meetings. I had over 50 meetings a week until I lowered the number of meetings. I cannot handle more than 23, 25 meetings a week max.

[10:13.2]
So I have to reduce the number of meetings and I do that and I have certain filters on that. So make sure I reduce the tire kickers. But when you're talking to qualified individuals, all you want to do is listen to see how, what synergies happen.

[10:30.6]
If there's something that you can assist with for free, just do it. You know, unless there's a cost or something associated with it. And there's only one of three outcomes. Number one: they speak good about you and never speak bad about you.

[10:46.6]
You have to get 10 good clients to avoid one bad client. Right? Right. Number two: they like you so much they end up hiring you and working with you. Right. Number three: is maybe they're not the right fit, they can't afford it, or whatever the case may be, but they can recommend others.

[11:07.0]
If someone recommends you, that's much more powerful than you tooting your own horn. And in order for people to actually get the meeting in the first place, that's where Skoop come came in. And so we looked at the problem.

[11:22.9]
I said, well, on LinkedIn for B2B services, and consultants, and all this stuff, there's really only two places on LinkedIn that generate that kind of business.

[11:38.4]
It's in your content and your DMs. Your emails come from your DMS, your InMails come from your DMs, your conversations for your bookings come from DMs, content, your LinkedIn newsletter, your streaming events, your PDFs, your regular posts, all that is on your post.

[12:06.1]
And there's systems to generate business on both of them, but there's problems with both of them. And the biggest problem is you need to distinguish yourself from all the spam. And so I don't know about you, and everyone has different numbers, but I know that on a single message, if I connect with someone, I only have about a 3% conversion to a vetted booked meeting.

[12:33.1]
That means someone I want to talk to that's on the same page. That's not very good. That's why people do multiple messages and all that stuff, right? And we realized what you mentioned, that if done properly, you can bump that up to about 21% by 6 times.

[12:52.0]
So, let's just say you have 10 connections come in a day, 10 new connections a day. Right. You have a daily process and you create this video. And there's a form that's a sandwich formula. I'll just explain it.

[13:08.2]
On Skoop, most of your conversations are predetermined to a certain extent. So there's a welcome button, I click it, it drops welcome text in it, and I make a minor change. It's just two or three lines of text.

[13:23.6]
Then I do a 30-second video that welcomes them, and then I title the video, make sure it has their name in it. And so one video for one person for 30 seconds, maybe up to a minute. Right. So what that means is think about the thought process of a person.

[13:41.4]
As a product, I want to increase vetted booked meetings. Well, If I got 21, that's two to three people. Extra meetings a day. Vetted meetings a day. That's huge.

[13:57.0]
Right? Because if you're trying to close one deal a month, or one deal over three months, or wherever the case may be. It's a gold mine. And so, when they connect with you, you move from level 0, to, say, level 1 out of a 1 to 10 scale They knew enough to say, okay, I'll accept his connection or I will connect with him.

[14:22.9]
And so at level one, you go as a daily process, and you go back and say, who connected with me yesterday? Not today, yesterday. Because I don't want to be blasting them messages right away. Give them some breathing room. So at least a day. Two days.

[14:38.1]
Three days. Whatever old. And all I did was send them a welcome message. Thank you for connecting. You know, hey, Adam, thank you for connecting so much. I really appreciate it. Welcome to the network. Notice you're doing a podcast.

[14:54.8]
I said, that's pretty unique. That's the whole message. Because people don't read. They scan. So if you write a novel, I hate to tell this to your whole audience. People don't read novels on LinkedIn. LinkedIn is like a text.

[15:11.6]
And so texts are meant to be very short, so they want to know what is it about. So those two to three lines tell that, the video says, hey, Adam, thanks for connecting. I appreciate it. I'm looking at your profile right now, and you have an interesting podcast.

[15:28.2]
I also have a show. I don't have a podcast. Love to know more about the podcast. I have a monthly show that I run interviews. I talk about systems and processes for sales. All pretty boring, nerdy stuff. But just sharing that with you.

[15:43.7]
I'm not sure how I can support you. But you know what, Adam? I have a really awesome network. I tell you what, if you have a chance, take a look at my profile, and if you see any dots to connect there, send me your booking link.

[16:01.1]
and I'll schedule on your booking link. I'm always open for a conversation. Thanks a lot. Have an awesome day. Now, what I said within that, it was really, like, 45 seconds. But what I said within that time period is: I called you by name.

[16:16.9]
I thank you for connecting. I talked about you, I let you know just a little bit about me, but I'm not going to all my services. And hey, I'm I'm creating this and this and this and this and all that stuff. Hey, buy my stuff, by the way, right? I didn't ask, but I did have an ask.

[16:33.9]
And the ask was if you have a moment, take a look at my network, right? And take a look at my profile. Excuse me. And they'll make a decision. And I also said, send me your booking link.

[16:50.5]
I'm not sending the link out. By doing that, you're putting the ball in their court. So systems with psychology make a huge difference. And then when they book a meeting with you, like, yeah, I totally want a meeting with this poor guy. Or I don't. And if they don't, then great, you saved yourself some time, right?

[17:09.1]
And you want to reduce that time. So that's the sandwich formula that Skoop is really effective with. And it allows you to move from person to person really quick. You get in, get out, take care of it. Hyper personalize. And if you have say, automation that does the connection or whatever or afterwards, that's fine.

[17:28.3]
But I tend to, I would say, have a six day gap. So you have enough time to personalize it, and then your systems can take over because the systems will just enhance that because not everyone will see the message. But if you send a secondary message six or seven days later, they'll bump it back to the top.

[17:48.7]
And so that's really kind of what you want to do. And that message has to be value driven. And so that is the secret sauce. And creating the system to solve that makes a huge difference. Now your question is, why don't they want to do it? Well, people don't like change, they don't like putting themselves out there.

[18:07.7]
It could be cultural, too. I had a good friend of mine and he's ethnic Russian, he's a US citizen, but, you know, he has a heavy accent and everything. And he says to me, his name is Max, great guy.

[18:24.6]
He's another developer partner of mine. And he says, Troy, how long does it take you to do the video? I said, for what? What are you talking about? He goes, the welcome message. Oh, the welcome message.

[18:40.2]
Yeah. You mean the 30-second welcome message. Yes, yes. It takes me 30 seconds. Right. He says, it took me two hours to do It. And so, he was positioning himself, and talking, and doing it, so the flow was off for him.

[19:00.3]
And so it's harder for some people to just create a message, almost like a voicemail. You have to think about, like, you're just a human. You're a person talking to another person. And so he had cuts in and out. And I told him, hey, this is what you need to do.

[19:17.2]
And I was partially joking, but I was totally serious. I said, okay, go to the side three quarters, and get that bottle of vodka, and put it right on the table. Right? And then look at it to the side and do the video that way.

[19:33.6]
He didn't understand, but it's like, it would be so funny because he would be serious. Because this is Russian, they drink clear liquor and all that stuff. And he would be looking. Yeah. That would have been a personality grab.

[19:51.4]
I said, just do it for fun, and they'll love it. They'll just laugh, and then you'll get more business that way. I said, because people have to like you. They have to. Because 80% of the decisions for all business is, do I know, like, and trust this guy enough.

[20:09.0]
That's it. Your services are a checklist. You have to get that personalized part. Anyway, when people receive this message, they're like, oh, I know what it is. He sent. Oh, he created an original.

[20:25.0]
And the video looks raw on purpose. It doesn't look polished. Oh, he made it just for me. I know it's for me because it has my name on the bottom of it. They click through it. And even if they don't have a booking link, your video will have your booking link right there.

[20:41.2]
You gotta think about it. So you're just moving small steps that have less friction. that build a relationship. Now, on the AI side, we purposely didn't add the AI to the video. We didn't want to do that.

[20:57.9]
If we did that, a lot more people would use it, but a lot of people would hate it, as well. Because people know AI. They'll notice it. Yes. Yeah, they notice it. Yeah. And they get the names wrong 20% of the time. So if you're gonna get it wrong, just get it wrong as a human, you know?

[21:17.0]
You know? The other side was content. I said, oh, they always have these great video people. They have people that know how to use Canva. They have the ideas. I said, but what is the thing that kind of sucks a lot of time up?

[21:34.5]
It's the actual written content. So on average, it takes 45 minutes to write that content. I said, well, we had Skoop absorb your profile, and it looked at it. It ran a DISC analysis, which is a personality set of traits, and it understood how you thought, how you wrote, and then it also absorbed your last 10 posts.

[22:00.7]
So I had a knowledge base. And so when you're creating new content, it gives you, like, here, here's five different posts. We think you just click it and it will generate the whole post, and it'll even separate it out in bullets and stuff like that. And then instead of spending 45 minutes, you spend five minutes to edit the hook to verify it, and move on.

[22:22.8]
And if you have something like a talking head video, you just talk. You just take the caption, drop it in there, and say, hey, just break it up this way, and it will generate an entire post for you. And plus, we added a CRM.

[22:37.9]
I forgot to mention that. So most people just forget to follow up. Right? And the key is in the follow up. Right? Yeah, the money is in the follow-up. So, we just add a CRM with a sales pipeline, and in case you didn't have anything.

[22:54.0]
Yeah, so we just did that. And I think next year we'll do a full video editor. But you get the idea. And it works with systems, or sales processes, or individually. So if you have some kind of outreach system, you can use it.

[23:11.0]
It works with email, works with Gmail, 365, you name it. And we're plugging it into, like, multiple social platforms as well. So, anyway, enough nerd talk. But you get the benefit. You get the idea of the benefit there.

[23:26.7]
Troy, this is one of these rare conversations where you provide that really deep truth behind the hustle. And it's incredible how you've built your momentum through authentic connection, not ads. And that's a message the whole industry needs to hear. Where can listeners learn more about you and Skoop?

[23:44.9]
Yeah, so you just look me up on LinkedIn. It's just my first name, last name, and it looks like me. There's another Troy Hipolito out there. That's my brother. He's actually my brother. He's full Filipino, but he's actually six-foot-tall and full Filipino.

[24:00.7]
I'm the shorter guy, but I look mixed, of course. So now I usually have an orange or blue background or something like that. LinkedIn is always good, and for Skoop, it's skoopapp.com, so, skoopapp.com and it's a K instead of a C because I couldn't buy the domain.

[24:21.7]
And as far as the doing that, I just used my systems to reach out to people, and when I had meetings with them, they always had that problem. And so I got my initial 500 test users through LinkedIn, and now we're targeting group users, so resellers, and then CRMs, and partnerships like that, which all of them are on LinkedIn as well.

[24:47.7]
And so that's one way we diverted the advertisement arena at first anyway, and we may pick up some other ideas on it. It's been a little hand-to-hand combat, but so far it's been pretty successful. It's profitable, and we're gonna move towards 5,000 concurrent users over the next 20 months.

[25:09.1]
That's incredible. Well, and that just goes to show everyone listening today, you don't need ads to build that momentum. You really just need energy, clarity, and a message that moves people. I'm sure our listeners can, you know, see, Troy, that your story is proof that that AI momentum actually just starts with human discipline and a clear North Star.

[25:28.5]
So thanks for joining today, Troy. Thanks so much, Adam. I really appreciate it. You got it. All right, thanks everyone for listening to "Is Anything Real?", where we cut through the noise and find what's actually working in growth. If this episode sparks something, share it, leave a review. and plug in next week.

[25:45.6]
And until then, stay energized, stay curious, and keep your momentum real.