I was growing my newsletter list one DM a time when I shot Steven Charlap a message at 12:54 PM on a Saturday afternoon in October.

"Steven, I'm writing a newsletter about founders who built their company and are still the face of it. You're exactly the founder whose take I'd value. Open to connecting?"

One minute later I get a one-word response.

"Cost?"

I wasn't even pitching him. I was just trying to get him to subscribe, and he jumped way ahead of me.

I told him there's no cost, the newsletter is free. He said sure, and at 1:16 in the morning he sent me his email with one more line.

"You should do one on Medome."

So I took a look at his socials, and he agreed to hop on a call that Friday. I would soon find out why he jumped immediately to the question on price.

A Harvard MBA who wanted a cockroach guarantee

I came to that first call to hear his story, and he was ready to talk numbers.

Before I’d said a word about what I charge, he laid out his terms. “If a guy pitches me $2,000, I expect to see $4,000 in revenue.”

He’s had guys come to him and say hey, give us $50,000 and we’ll guarantee you $250,000, we’ll even put it in escrow. And then they ended up chickening out.

Then he told me about a Harvard Business School case study on an exterminator called “Bugs” Burger Bug Killers. They guaranteed a restaurant would never see a cockroach, as long as they kept the lids on tight and took the trash out every day.

“Be my partner, not a vendor,” he said. To him, a partner stands by his work and guarantees the results.

And he lives by it. He tells his own customers if Medome doesn’t help you, it’s free, and even lists his cell number right there on the website.

He trained as a doctor at NYU, got his MBA at Harvard and then co-founded HealthDrive. They went on to serve over 5 million patients and made the Inc. 500 twice before he sold it. This is not a guy who is going to fall for an agency pitch deck.

He's in his late sixties and Medome is his legacy project. He lost his brother, a cardiologist, to a misdiagnosis 13 years ago. Since then his life mission has been to make sure that doesn't happen to anyone else. And he puts his money where his mouth is.

He's invested $6 million in Medome, his AI-first primary care app, 4 of his own money and 2 from outside investors.

"I'm an animal," he laughed. "I work seven days a week, 12, 13 hours a day. And I still have time to watch TV for a few hours at night before I fall asleep."

In one of his recent LinkedIn posts he put it this way, “Building it was Herculean. Getting anyone to give a damn is Sisyphean.”

Steven wanted guarantees. I wanted to figure out why all the content he was pumping out wasn't turning into sales.

He wasn't going to take my word for it. He needed proof, so he told me to book another session once I had something to show him.

After that first call I spent the weekend going through all of his content and built him a diagnostic. I DM’d him the link that Sunday evening and suggested a second meeting to go deeper on it.

Everybody runs for the hills

Monday morning he wrote back. "Nice analysis. I'm looking for a partner, not a vendor. That means you get paid more from success and less from effort. Can you work on those terms?"

He agreed to hop on a call later that day, and right off the bat he cut to the chase.

"I appreciated the analysis," he said. "What you identified is well known to me, that it has been helter skelter in the way that we have marketed."

Then he went right back to his posture.

"I get approached every Monday and Wednesday by marketing people," he scoffed. "And Monday, Wednesday and Friday is being underrepresented. It's every day, marketing. And I say the same thing to everybody, and everybody runs for the hills. Be my partner, not a vendor."

The way he saw it, I was asking for guaranteed payment without a guaranteed return. "Take the risk with me, earn a much greater reward," he said.

The minute he asks a marketer to get paid on results instead of a retainer, they run for the hills.

Then he asked me if he'd already told me the story about the bug killers. I nodded, as my mind wandered and imagined the cockroaches scurrying away from the exterminator.

On paper, Steven should be crushing it

He recently sat down with a senior hematologist who tested Medome on 28 really difficult cases, using patient history alone. Medome got all 28 right, and the hematologist was blown away. Now they're building a case study together.

He's been on about 18 podcasts and written two books, and he's got almost 18,000 followers on LinkedIn. He's proud of that number, and he has every right to be.

He’s posted 457 times on LinkedIn alone, but his content isn’t drawing in any customers.

So I went through all of it that weekend. All 9 accounts across Medome and Medome Men. His LinkedIn posts, both company pages, YouTube, TikTok, Instagram, Facebook, X, Threads and both websites. I even signed up for the free trial to understand the tool myself.

And the same three mistakes showed up over and over again. They were so common that I ended up writing a LinkedIn post about them.

Too much time in the editing chair

On our second call I asked him how he was producing his videos.

“Oh, I just put my phone up, and I do a video,” he said.

“But who edits your video?” I asked.

“Nobody.”

He adds the captions and the music himself, and then the same videos go out across TikTok, Instagram and YouTube.

That’s the animal in him. But every platform has its own native language, and if you don’t get it right, your content gets punished.

He filmed, edited and posted 11 Shorts to YouTube, got 1 subscriber and stopped. On X, the Medome account tweeted 334 times in 11 months, and most of those tweets never got a single like.

That’s a lot of hours in the editing chair for very little return. And for a guy already working 7 days a week, those are hours he could be putting back into Medome.

Two companies under one name

Steven doesn’t think of Medome as one company. He thinks of it as two.

“We’re really in two different camps,” he told me. One is AI-first primary care for everyone. The other is Medome Men, built for men’s sexual health.

When I went through his socials, I identified 8 different audiences across his 9 social media accounts. He’s even got 2 LinkedIn company pages for the same company. Every post skips around to a different buyer, so no one buyer ever feels like he’s talking to them.

And the thing is, his sharpest message is already written. On our first call he told me men won’t talk about this stuff with their best friend or their partner, but they’ll go straight to ChatGPT and start taking Viagra or testosterone without understanding the risks. His Medome Men website nails it. “ED pills turn off the warning light. They don’t fix the engine.”

That’s the buyer. Every post should be talking to that guy.

Don’t let your balloon pop

As JK Molina says, “Likes ain’t cash.” Great content with no offer never converts.

Steven told me he rarely includes a CTA because when he does, his posts get fewer impressions. He even pulled one up a post about Medome Men that  got 188 impressions.

So I had him scroll down to his red balloon post. The one that ends with “Don’t let your balloon pop!” There wasn’t a link anywhere in it, and that post got about 3,300 impressions. That’s 10x what his posts normally get.

I asked him where he sent that reader. “Set the, uh...” he started, and I jumped in before he could finish, because the answer was already clear.

He was going for the impressions, and not the buyer. The thing is you never know which post is going to pop off. That’s why most posts need some type of CTA or PS so the reader knows where to go. For him that’s a free trial or a free assessment. If you’re worried the link hurts your reach, pin it in the comments.

Still rooting for Steven

After a few conversations, Steven and I weren’t able to come to terms. That being said, I’m still rooting for Steven and Medome. So I followed up and asked if he’d be open to being featured in the Path to Pipeline, and he said, “Yes, I would.”

And he’s not standing still. About a week ago he posted this.

“I’ve posted about Medome Men every single day. LinkedIn. Instagram. All of it. It’s felt stagnant.”

So he’s changing course and going straight to urologists who’ll recommend Medome Men to their patients. A few days later he followed up. “Zero comments. That’s what my posts about men’s sexual health get.”

He’s right that no one is going to be liking and commenting on a post about ED on LinkedIn. But more people are seeing those posts than are publicly letting on. On our call, the post he’d put up that same day already had 266 impressions. Those men are reading in private, and they just need somewhere to go.

He thought nobody cared. The reality is he was looking at the wrong number. He just never gave those silent readers a private way to raise their hand.

Steven already has a serious body of content. He’s got the product, the pedigree, the podcasts, the books and the followers. He’s got a lot of things to work with, and this is really about putting it all into practice.

If that sounds like you, you’re probably closer than you think. You don’t need to post more. You need a way to turn the people already reading into buyers.

Pull up a chair on Nov 10

On Monday, November 10 at 11 AM ET, I’m hosting a fireside chat with my friend Arturo Del Rio Jr., founder of Stacked Growth, on how to turn webinars into clients.

As Arturo likes to say, “people don’t wanna be sold anymore. They want to be educated.” A webinar lets them see you do your thing before they buy, without the pressure of a one-on-one sales call. That’s what’s been working for me.

If you're a founder with an audience and no system to convert it, save your seat at this link.

- Antonio