23,000 LinkedIn connections.
Zero messages sent.
Ignacio needs 16 new clients per month to replace his $180,000 product manager salary.
He’s charging $500-1,000 per automation project.
The math is brutal: 4 new deals every single week.
He’s got the skills.
He built an AI agent for a Miami law firm that books meetings on WhatsApp.
He’s creating custom automations for businesses.
His wife supports him.
He even built a 7-agent blogging system that runs itself.
But he won’t tap into his biggest asset.
He’s sitting on a mountain of curated connections—founders, entrepreneurs, even a Hollywood actor.
Yet he’s waiting.
Refining his offer.
Perfecting his positioning.
Preparing to scale before he’s even started.
There’s a Word doc full of LinkedIn posts he hasn’t published.
He hasn’t even told his network he lost his job.
What’s really holding him back?
And what happens when I challenge him to post something right now, live on the call?
FULL RECAP
“So, I’m going to ask you my first question,” I told Ignacio as we settled into our conversation. “Tell me what’s going on, what are you doing, what’s working, what isn’t working. Let’s find something we can fix together.”
“I was working for Corporate America and was fired a couple of months ago,” Ignacio replied. “I was a product manager. I’m happy, because I was expecting it. I was responsible for a SaaS app, and the company decided to end-of-life it. Three days after the app was dead, they fired me. I was expecting that, because there was no place for me.”
Ignacio had that particular kind of entrepreneurial energy that comes from being knocked down but not out. At 40-something, this was his third attempt at building his own business. He’d started offering AI automation services to small businesses in Miami, leveraging his product management background and technical skills. On the surface, everything seemed to be going well - he had clients, he was building solutions, he was excited about the possibilities. But as we dug deeper, the real challenges emerged.
“I want to scale, I want to get more businesses, and that’s the challenge that I have now,” he continued. “Building the solution, that’s not a problem. The problem is finding the right customers.”
I was curious about the numbers. “Are you currently making enough to live off it, or is it still building up?”
“No. I was making $180,000 as a product manager, and I want to have the same or more.”
This is where things got interesting. I pulled out my calculator.
“So $180,000, that’s like $12,000 or $14,000 per month in profit, not in revenue. The revenue goal is somewhere around 20K, right?”
“Exactly.”
I asked about his pricing structure. He charged between $500 and $1,000 for setup, then $250 to $1,000 per month for ongoing automation services with a three-month commitment.
“Did you run the math on how many clients you need?” I asked.
“16. I need 16 new customers per month.”
“So you need to be closing 4 new sales a week, every week, for this to work.”
The mathematics of his situation painted a stark picture. At his current pricing and close rates, Ignacio would need to spend essentially full-time on sales just to replace his corporate salary. This is a common trap I see entrepreneurs fall into - they focus on building the perfect scalable system when they haven’t yet figured out how to succeed at a smaller scale.
“You’re basically looking at half-time sales,” I explained. “If you need 4 more clients every week, and you’re really good at sales, you might close half the people you talk to. That’s 20 sales calls per week. That’s a full-time sales job.”
“100%, I agree.”
This led me to one of my favorite concepts in entrepreneurship - the order of magnitude problem.
“The thing that I’ve noticed in entrepreneurship in general is that we progress in order of magnitude leaps. If you’re making something like $500 or $1,000 from your business, then getting to $2,000, you maybe can do it linearly. But getting from $500 to $5,000, you can’t do it linearly. There’s a leap there.”
“One of the hardest leaps is from zero to something, and you already did that. You’re in a ‘something to more’ phase.”
Ignacio had been thinking about this the wrong way. Instead of focusing on systems that would work when he had hundreds of clients, he needed to focus on getting his next 10 clients through methods that absolutely don’t scale.
“With that in mind, what have you been thinking about getting the next 10 clients - not 20 a month, but just the next 10 clients?”
He outlined his strategy: hyper-customized cold email campaigns, AI-powered blog content, and eventually referrals. All solid approaches, but all requiring significant time and money to work at scale.
I’ve seen this pattern countless times. Entrepreneurs prepare to scale before they’ve learned to walk. Cold email can work, but it requires massive volume to be effective - thousands of emails per week. SEO takes months to show results. These are tactics for the 200th customer, not the 10th.
“The first customers typically come from things that absolutely don’t scale,” I told him.
“Referrals, I would say. My first customers were friends of a friend, the boss of a friend.”
“Exactly. Your referrals, your case studies, even the materials you would need to prove to other people that you can do good work - you usually bootstrap all of that with people you meet and know.”
Then he mentioned something that changed the entire conversation.
“Before we started recording, you mentioned that you had quite a following on LinkedIn.”
“Yeah, I haven’t tapped into LinkedIn yet, to be honest. I don’t have followers, I have 23,000 connections. So it’s people I can send a personal message to, it’s even better.”
I nearly fell out of my chair. Here was an entrepreneur struggling to find customers while sitting on a mountain of 23,000 professional connections.
“You are sitting on a mountain of gold. Not just in potential customers, but in customer research. You have an unlimited amount of people to talk to. At 20,000 people, you could sell your access to a huge audience as a business at that scale, because you could even sell market research.”
“But it sounds like you’re waiting until you have the right thing, so you can announce it to your LinkedIn audience. What you actually need is to start talking about this, about your experience, about what you can do. You should be able to get into conversations with people who are like, ‘Wait a second, what is this AI automation that you speak of? What’s possible?’”
But there was something holding him back, and as we dug deeper, the real issue emerged.
“I’ve been shy with LinkedIn, I’m not gonna lie. I don’t know how to position it.”
“What’s your intuitive worst-case scenario for doing the wrong thing on LinkedIn?”
This question unlocked something deeper.
“I’m gonna be completely honest. If I fail again - when you’re an entrepreneur, the chances are against you. I’m not 20 anymore. Every time I had to look for a corporate job, I used LinkedIn, and I got it. I’m afraid that if I go full entrepreneur and then fail in some ridiculously massive way, I could never get a job again.”
Here was the real problem. Fear of burning bridges was preventing him from using his most valuable asset. It’s a version of what I call the “backup plan trap” - having an escape route often prevents you from doing what’s necessary to succeed.
“This is the third time you’re doing entrepreneurship. You’re not a young kid anymore. Does it sound like you would want to go to a corporate job?”
“No. No. To be honest, no.”
“When you’re not using what you have - and it really is an incredible asset - because you don’t want to burn the bridges, that actually reduces your chances of success tremendously. Not just for one reason, but for two reasons. One, you’re not using the best asset you have. And two, there was this Roman technique where they burned the ships so that the soldiers couldn’t back out of it. When you burn the ships and you don’t have anywhere to retreat, the things you’re willing to do for your business increase tenfold, a hundredfold.”
I shared my own experience with the stress and uncertainty of entrepreneurship, and how having a backup plan, while it sounds rational, often slows you down.
“The kind of people who would see you fail at entrepreneurship and say, ‘I don’t want to hire Ignacio to do a product manager job because he failed at entrepreneurship,’ are not people you would like to work for anyway.”
The conversation shifted as Ignacio began to see his situation differently.
“You wouldn’t be able to get a job that assumes you would want to stay there for a decade and climb the corporate ladder. But you would not want to get a job that assumes you want to be there for a decade. Worst case scenario, you get a job for 6 months, a year, 2 years, and then the itch comes back.”
“If we were the kind of people that were climbing the corporate ladder, we would have been pretty high on it by this point. We’re not on the corporate ladder because we’re kind of crazy. And that means if you do need a backup plan, you just need one job. Out of your highly curated, very large network of connections on LinkedIn, if you need a job, you just need one.”
I got into a roll outlining all of this, but luckily I could see Ignacio nodding. By the end of our conversation, the path forward had become clear.
“I’m going to challenge you to something practical, right here, right now. You can open up LinkedIn and say, ‘Hey guys, lost my job about a month ago, working on something new, I’ll keep you posted.’ That’s it.”
“I think I will do it, but I need some time to think about the writing, not just impulsive.”
“You’re carrying the weight of not having admitted that you lost your job and you’re working on something new, which makes it much harder. You post something like ‘I lost my job, I’m working on something new, I’ll keep you posted’ - all you’re going to get is upvotes and thumbs up and ‘this is awesome’ and ‘congrats’ and ‘looking forward to seeing what you build.’ It is impossible to get a negative reaction online for that kind of thing.”
As our conversation wound down, I could see something had shifted for Ignacio. The tactical problems he’d been wrestling with - how to find customers, which niche to serve, how to scale his automation business - were still there. But now he could see that the real barrier wasn’t strategic, it was psychological.
“I’m gonna sit down and write the post,” he said finally. “You made me realize that LinkedIn is something there that I need to discover and leverage.”
Sometimes the biggest breakthroughs in business aren’t about finding new strategies or tactics. They’re about recognizing what you already have and giving yourself permission to use it. Ignacio had spent months trying to build scalable systems to find customers while sitting on 23,000 potential conversations. The solution wasn’t in the next marketing automation tool or the perfect cold email sequence. It was in admitting he was human, sharing his story, and starting real conversations with real people.
