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Paul left his job at Dell 4 months ago.
He’s been building Quizlink, an AI-powered learning tool, for less than a year total.
On launch day, two complete strangers - consumers - paid him money.
Real customers who had never met him before.
But Paul still doesn’t have a single enterprise client.
That’s his target market now - companies with compliance requirements and actual budgets for training tools.
He’s spent 2 months planning this pivot.
Building admin dashboards in his head.
Researching cold email tools and LinkedIn outreach strategies.
But there’s something Paul is avoiding.
Something scarier than building features or writing cold emails.
What happens when I challenge him to face it today?
FULL RECAP
“Hold on, are you talking about adding features before you’re talking to clients?”
Paul had just explained his plan to build an admin dashboard for cybersecurity companies before approaching them with his learning platform, Quizlink. As a software engineer he was doing what felt natural: building.
“We procrastinate by building software. We procrastinate by adding features. We procrastinate by planning things. We procrastinate endlessly, because the act of selling and especially the specific circumstance of being rejected is very, very unpleasant and scary.”
“Thing is, you need to get rejected. You need to talk to people who will tell you, ‘Listen, we will never buy this in a million years because you’re not SOC 2 compliant, or some other b******t.’ But you need to hear them say that, and then you need to ask them, ‘Hey, and if we’re SOC 2 compliant next month, let’s hypothetically assume that we get this done. Are you buying?’ ‘Oh, no, not this year, not this budget.’ That means the SOC 2 is b******t. That’s not the reason.”
Paul nodded along. Like most technical founders, he was replacing the scary, valuable work of customer discovery with the fun, less valuable work of feature development.
This is the central tension in technical entrepreneurship: the skills that make you an excellent engineer are often the very things that prevent you from building a successful business. Code is logical, predictable, controllable. Customers are none of these things.
...
“The biggest challenge I have right now is niching down,” Paul had told me at the start of our conversation. His learning platform could theoretically help anyone learn anything - a classic problem for most startups.
“When we started, we were trying to target students, that’s really not a good target market,” Paul explained. “When we started talking to a lot of students, we realized that yes, they want to study too, but more than anything, they just want something to help with homework. They don’t want to learn more, or know more, they want to pass things with less effort.”
Based on advice from Neil, a cybersecurity entrepreneur who’d reached out on Twitter, Paul was now considering pivoting to cybersecurity training. It made sense on paper - constantly changing compliance requirements, companies with budgets and legal obligations to train their people.
“You haven’t got your first cybersecurity client, right?” I asked.
“Yes, that’s why I’m not sure about the niche of cybersecurity because we haven’t been able to secure any deals in that space.”
This revealed the deeper issue. Paul had identified a promising niche two months ago but hadn’t truly tested it. Instead, he was planning features and researching tools like Apollo for cold email outreach. The engineering mind wants to prove the niche is working, but the scientific approach is to disprove that it’s not working - to get to a definitive yes or no as quickly as possible.
...
“How do you get the first cybersecurity customer?” I asked.
“LinkedIn and... Apollo, that we’re trying to use for email outreach, and then even with LinkedIn, we’ve got a lot of tips on how to approach leaders or decision makers at companies, like how to warm up, how to before you even approach them, just make sure the couple weeks leading up to you connecting, you’re posting content that’s close to what they’re doing...”
“It’s a long-term thing, it’s a slow thing, and it’s absolutely unnecessary for your first client.”
“How many people do you know who are engineers?”
“A lot. Most of my friends are engineers.”
“Right. How many people they know, that’s like to the power of two of whoever you know. That’s a lot of people. That’s a lot of reach into the industry. All you need to do is figure out who of these people works for a company that has some cybersecurity requirements.”
This is where I see the biggest missed opportunity with technical founders. They’ll spend weeks setting up complex cold outreach systems, learning about exponential back-off sequences and A/B testing subject lines, when they’re sitting on a goldmine: their existing network. Paul knew dozens of engineers, each of whom knew dozens more. That’s not 2-3 contacts - that’s potentially hundreds of connections into companies with cybersecurity needs.
“I don’t think reaching out is... if it’s your first network, like someone you know... I think most of the people I know aren’t really at the decision-making level.”
“Yeah, no, of course everybody you know are individual contributors, and they do the groundwork. That’s cool. But they work at companies where they themselves needed to pass, perhaps, needed to pass a security certification exam or thing. Therefore, you can talk to them about what was it like, how did they prepare, was it easy, was it hard, who administered it, and who’s the team lead who actually runs these things? And can they connect you to the person?”
I watched Paul’s expression change as this clicked. “Now you mention it, I actually think I might... someone just popped in my mind that might be good to...”
“Probably somebody like that.”
“Yes. And she’s not even an engineer. I think she works at HR for the company.”
...
The conversation had shifted from complex automation strategies to simple human connection. But Paul was still thinking small.
“I’m just thinking maybe like 5, but I’m sure if I reviewed and went through LinkedIn, especially recently, because I’ve been going out for a lot more events now...”
“Why are we talking about 2 or 3 people? When you’re talking about 20, or 30, or 40, now we’re starting to talk about a surface area that should create something.”
This is the mathematics of early-stage sales that most founders miss. Cold outreach might get you a 2-3% response rate if you’re lucky. Warm introductions through your network can get you 50-80% response rates. The difference isn’t just efficiency - it’s the difference between getting definitive market feedback in weeks versus months.
“I’ve been discovering, to my deepest surprise, that outreach and this kind of business activity has this completely weird dynamic. You don’t get the contacts through the people you reach out to. But suddenly, people start finding you. People that you need from completely different areas. It’s like you have a garden, and you water one spot, and a tree sprouts in a completely different spot.”
“It’s the algorithm, right?” Paul said, understanding immediately. “It just notices that these are what your interests are, and then it learns from that, and next thing you know, it comes to you, and you start attracting it, and after a while, you don’t have to go look out for it.”
“Exactly. And therefore, the more you put out the thing that you... this should start happening to you today. Because it can, because you have the entire day in front of you.”
...
“This is not a tremendous amount of work. This is a today kind of thing. And since this is a today kind of thing, then by the end of today, you will be in a different spot compared to the spot you’re in right now.”
Paul had gone from planning features for hypothetical customers to realizing he could validate his entire cybersecurity niche in a matter of weeks, not months. The shift wasn’t just tactical - it was philosophical. Instead of hiding behind code, he was ready to have the uncomfortable conversations…
TL;DR
160,000 monthly users.
€0 in revenue.
Akash built a thriving Urdu poetry platform that became a massive success in his niche community.
Hundreds of thousands of engaged users.
Strong social media following.
Zero clue how to monetize it.
Now he’s in Berlin with one month of savings left.
He’s juggling three different business ideas - an AI agency, a home services marketplace, and desperately searching for freelance work to pay rent.
But there’s a pattern emerging that he can’t see.
When it comes to finding clients, he won’t spend €20 on a premium platform membership because “too many people are competing.”
This is the same entrepreneur who built a community of 160k users from scratch.
The disconnect is staggering.
And it reveals something deeper about why talented people stay broke.
What does it really take to go from survival mode to success?
FULL RECAP
Sometimes the most obvious advice is the hardest to take. Last week, I had a conversation with Akash, a 20-something entrepreneur from Berlin whose story perfectly illustrates why most people stay stuck despite having all the tools they need to succeed.
Akash: “I am a product designer. I’ve worked in design for about five years now. I did my first startup in 2019 when I was in college with my friends. It was a poetry platform, a UGC platform, so it has about 160k users still monthly visiting, more than a million Google events happening still, more than 140k on Instagram.”
Eli: “Is it making any money? Because the numbers are great.”
Akash: “There’s a bit of a gap there. It’s doing well, but the only way we could figure out to make money was advertisement, and Google doesn’t pay that much if your audience is from a certain country. We were targeting very niche poetry, Urdu poetry, which is called Shayari, which is like a dying art.”
Here was my first surprise. Akash had built something remarkable - a thriving community around Urdu poetry with serious engagement numbers - but he talked about it like a failure. In the world of online entrepreneurship, getting 160,000 monthly active users in any niche is extraordinary, especially on a first attempt.
The conversation continued as Akash explained how he’d burned out from juggling the platform, a full-time job, and freelancing, eventually discovering he had ADHD. He’d handed over his shares to his co-founder and moved to Berlin to start fresh. There, he’d launched an AI agency and planned a home services marketplace called HealthWell, modeled after India’s successful Urban Company.
But now he was running out of money.
Akash: “I realized we are running short on money, and investor money is not going to give us runway. We need to prove some traction before we raise money. So I posted on Reddit, and I actually took advice from people which says you need to freelance, build up a stable income and then look out for these ventures in your free time.”
Eli: “How badly do you need freelancing gigs? How long can you live without it?”
Akash: “To be honest, it’s very urgent. One month, one and a half months.”
This is where things got interesting. I offered Akash three paths forward: figure out how to monetize his existing poetry platform, focus on getting his marketplace to the 200 bookings he believed would attract investors, or solve the immediate crisis by landing freelance work. He chose the third option.
Eli: “Look, you’re a talented, well-spoken, and very experienced developer. What’s the problem? What’s going on? Why aren’t you overwhelmed with opportunities right now?”
Akash: “I tried going on to different platforms, and I see there are already so many people competing from Brazil, India, Pakistan, Vietnam. I cannot compete with their prices. So I tried niching down on European platforms for freelance, like Malt.de, Freelancer Map. But they also want me to upgrade to premium, to apply to more jobs. They just let me apply to one job, and they want me to upgrade. One job is nothing.”
Eli: “How much is the platform fee?”
Akash: “It’s 20 euros per month.”
Eli: “And you’re telling me that with your back against the wall, you apply to one project because to apply to more projects, you need to pay €20 and that’s too much?”
I couldn’t believe what I was hearing. Here was someone who’s obviously an entrepreneur in spirit, one month away from financial disaster, refusing to spend €20 - less than what he probably spent on food in a few days - to access more job opportunities.
...
Eli: “If a platform allows 10 people to apply for free, then anybody who’s offering a project on that platform is going to get a lot of low-quality applications. The moment you pay 20 euros for this, you are in the top 1% just through the willingness of taking the risk. And if you then apply to 500 projects and you do it 8, 10 hours a day until your fingers bleed, you are in the top 0.01% and you’re guaranteed to get something.”
Akash: “I think it’s also inside me a bit of fear that what if I get the membership of the platform and there’s no new jobs posting regularly. Like I just see two jobs, I don’t get any.”
Eli: “That means you take a risk and it doesn’t pan out. Man, you’re a month away from being out on the street. What are you talking about? You’re an entrepreneur. This is what entrepreneurial life is like. You do many, many things and most of them don’t work out. That’s the point. If you wanted things to work out, you’d get a job.”
This moment crystallized something I see constantly in my coaching work. Akash was willing to spend €60 on a cold email automation tool - something with much lower odds of success - but balked at spending €20 on a platform where people were actively looking to hire someone with his skills. The psychology was backwards.
Eli: “What you get paid as an entrepreneur for is your capacity to take risk. Not your work. Not the hours you put in. How far are you willing to stretch out your neck under the knife? That is what you get paid for. And right now, you aren’t pushing it far enough to spend 20 euros.”
Akash: “Yeah, that’s a very interesting point. And the only thing that I think that’s like a brick in my head is like so many people like me, 100, 200, 300 people are applying for the same thing.”
Eli: “They are not, because most people are exactly like you. They don’t want to pay €20. The question is not how to do it as cheaply as possible. The question is, how do you do it as quickly as possible? If you apply to 500 jobs a week, because you’re all in, and you pay all the platforms whatever they need to get paid, and it’s sweat, blood and tears, and it takes a week, then that’s it. And you start to make money.”
I realized we’d hit the core issue. Akash wasn’t really willing to be uncomfortable, even when comfort was no longer an option. This is the fundamental misunderstanding most people have about entrepreneurship - they want the upside without the downside, the freedom without the risk, the rewards without the uncertainty.
...
By this point, I could see the conversation was more valuable as a wake-up call than as strategy session. We talked briefly about his other ventures - I was genuinely impressed by what he’d built with the poetry platform and offered to connect him with people who might help him sell it or the marketplace. But the real work was simpler and more urgent.
Eli: “In fact, I want to end this call early so you could go and do it. We can talk here for an hour and it will not provide the same benefit as you going and doing it. And then in a couple of months, we can do another podcast and you’ll tell me how wonderfully overwhelmed you are with freelance work and how much money you have to invest in your startups.”
Akash: “Yeah, it makes sense. Let’s get off the call. You will hear a message from me like whenever I do this. I did it, and fingers crossed, now I’m going like 10, 20, 30 applications every day, and let’s see how it goes.”
After we stopped recording, I reflected on the pattern I see constantly in my work. We want something, but we don’t actually go the distance to get it. We le…
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 busines…
Ben charges $120-160 for oil changes, but shops sell them for $60-120.
He can’t compete on price.
He’s a mobile mechanic in Flint, Michigan with three years of experience.
Ben knows he’s good at basic maintenance but feels like an imposter when customers need complex repairs.
His business is barely covering his bills.
He’s stuck between two problems: not enough customers and not feeling qualified enough to market himself confidently.
Then we dig into who’s actually buying $160 oil changes.
The answer changes everything about his business model.
What if the problem isn’t his prices?
What if he’s targeting the wrong people entirely?
By the end, Ben’s thinking about a completely different type of service.
One that could charge $500 for what used to be a $100 job.
But can he find customers who would actually pay that much?
FULL RECAP
“I think a good order to tackle these things would actually be to start from the second and then move to the first, because if you are walking around with, like you said, imposter syndrome, then everything you do in terms of marketing, getting the word out, getting people to be interested in you is going to be tainted with that, because it creates this sort of timidity in us.”
Ben, who runs Wrench Wagon LLC, a mobile mechanic service in the Flint, Michigan area, had come to me with two problems: not getting enough customers to make ends meet, and feeling like an imposter compared to mechanics with 20 years of experience. Like many entrepreneurs, he wanted to jump straight to marketing tactics. But I’ve learned that when someone is walking around feeling like they need to hide something about themselves, no amount of marketing strategy will fix the underlying issue.
“So the things that I know I’m absolutely confident in are oil changes on just about any vehicle, any American, Japanese, most European. I can do brakes on American cars, Japanese cars, without issue, and most European, those are a little spotty, because some of the German engineering gets a little crazy, but for the most part, brakes. As well as diagnosing engine problems, I’ve gotten pretty good at spotting and addressing the concerns with engines, or at least finding and separating out the more simpler repairs from the things that need to go to a real engine specialist.”
I noticed something interesting as Ben talked through his competencies. His voice became more confident when discussing oil changes, slightly less so with brake work, and noticeably more tentative when he got to diagnostics. This wasn’t about his actual skill level - it was about his certainty in different areas. And that certainty, or lack thereof, would come through in every customer interaction.
“If what you proposed you did to people was oil changes while they’re at work or otherwise busy with their lives - you pick up their car, you do an oil change, you return the car, they pay you, that’s it - would your imposter syndrome come into play at all?”
“No. Not a lot. I feel that confident.”
This was the moment I saw Ben’s shoulders relax. When we stripped away all the complexity and focused on what he genuinely knew he could deliver flawlessly, the impostor syndrome evaporated. But I could sense resistance building.
...
“My big no is the fact that for what I want for my business, if I were to just focus heavily on oil changes, regular shops like your regular mom-and-pop shops, or places you go to get your oil changed, even the dealership, they specifically make oil changes, they sell them at a loss, a small loss, or a break-even point. So they can bring their prices down to a point where I could not compete.”
This is where most business conversations get stuck - in the weeds of cost-plus pricing and competitor analysis. Ben was thinking like someone who had to compete on price, but he was offering something fundamentally different. I needed to help him see that.
“An oil change happens, what, once a year, twice a year?”
“Two to four times a year.”
“In practical dollar terms, the difference between a $100 service once a quarter and $200 service once a quarter would only be significant for a person who really makes very little money. It’s within the realm of going to a restaurant with the family, right? It’s not a crazy difference.”
I was watching Ben process this. He’d been so focused on the shops selling oil changes at cost that he’d forgotten his service was completely different. He was solving the problem of time, convenience, and hassle - not just automotive maintenance.
...
“At the low end, pricing is about whatever services and products you provide, plus a little bit of a margin. But at a different point, at a different price point, it’s about the value that the customer gets. You have a very specific thing. You drive around, you pick up the car, you do the work, you get the car back, it’s completely transparent to them, they waste zero time on it. And that is the key, the core of your service. It’s about convenience.”
This is one of the most difficult transitions for people stepping into business - moving from cost-plus thinking to value-based pricing. Ben was still thinking about what his time and materials cost him, rather than what the solution was worth to his customers.
“Let’s look at a lawyer, right? Somebody who charges maybe $1,000 per billable hour. If they don’t need to go have their car oil changed, and they don’t need to send their assistant to go have their oil changed, that might be worth a lot more than you’re considering to them because of convenience.”
“Funny enough, what you’re pointing out is actually something I’ve been planning. I’ve been working out pricing and planning of a subscription service, because I see how much would someone who has more expendable income value just not having to think about their car, because there’s probably a lot of people that don’t want to have to think about their car.”
Now we were getting somewhere. Ben had been thinking about this subscription model but hadn’t connected it to his imposter syndrome issues. The beauty of a retainer subscription service is that it detaches the amount of work you do from your revenue - you get paid to care about the car, not necessarily to do specific work.
...
“One of the things I think you’ll be getting paid for here is to just completely eliminate any thinking they need to do about this. Ever. At all. Like, the idea that they would never need to take their car to the shop, they would never need to go and wait anywhere, they would never need to figure anything out, and if any kind of light pops up or anything weird happens, they just text you, and you deal with it.”
This reframe was crucial. Ben wasn’t selling car maintenance - he was selling peace of mind. And peace of mind is priced based on what your clients are doing with the rest of their time, not on your cost of materials.
“Your distinction then becomes, instead of being the best mechanic in whatever the county or the state, you’re the most conscientious, nicest, easiest to work with, and delivers the best kind of service in the relationship sense. Not in the mechanic sense. And that, just from talking to you, sounds like it should not be a problem for you to stand out on that.”
“That’s something that I, in my current marketing, try to push. I have good communication. Whenever I get people who ask for quotes, I’m usually the person that gets a call, and I have a quote to them in half an hour. Sometimes an hour, if I need to shop parts. But I try to keep it very tight communication, very good, make it as frictionless to work with me on the communication side of things.”
Ben was already doing the relationship part well - he just hadn’t recognized it as his primary competitive advantage. Most shops optimize for scale; he was optimizing for the relationship. These are different businesses entirely.
...
“I think maybe, in general, slicing your clients by gender could be useful.”
“It could be. I can see that, possibly.”
“I think men tend to pretend they know more than they do, which makes it…
Denis has built the world’s smallest electric roller skate.
It works.
He can stand on it and cruise around Brussels.
But there’s a catch-22 that’s keeping him broke.
He needs €200,000 to manufacture at scale.
Investors want to see customer traction first.
But customers won’t buy something that doesn’t exist yet.
One prototype costs €1,000 to make.
Each additional unit costs another €1,000.
At that price, nobody will buy.
Denis has three wealthy friends who might invest.
They all say the same thing: “Show us people actually want this.”
Here’s what makes it worse: his product is illegal in half of Europe.
In the Netherlands, you can’t ride anything with a motor unless it has handlebars.
Different rules in every country.
So how do you prove market demand for something people can’t legally use in most places?
FULL RECAP
When Denis reached out to me about his “Catch-22 problem,” I thought I knew what we’d be discussing. Hardware startups face this classic dilemma all the time: you need money to manufacture, but investors want to see customer traction before they’ll fund you, and customers won’t commit to something that doesn’t exist yet.
What I didn’t expect was how quickly our conversation would pivot from manufacturing logistics to something much more fundamental: what business was Denis really in?
“So, the fact that it’s an electric roller skate, it’s not a super complicated device, but it still has existence in the real world. And people stand on it. So that also means that they put their person at risk using the device, and so it has to be safe.”
Denis had built a prototype of electric roller skates - not the shoe part, but a device that attaches to your existing shoes, complete with wheels, motors, and batteries. The idea came from his own frustration with electric scooters in Brussels being too bulky to carry around all day.
As we dug into the economics, the numbers seemed reasonable at first glance. His bill of materials came to about 300 euros per pair, with a target selling price of 500-600 euros. The catch was the frame - the aluminum structure that everything attaches to and that has to support a person’s full weight.
“The frame itself, it’s about 500 grams of aluminum, but it takes quite a big volume. It’s, like, mostly holes. The thing with CNC machining is that you pay for holes. You start from a brick, you remove until you have your product.”
The economics were brutal. CNC machining would cost 100 euros per frame, making the product unviable. Die-casting could work but required a 50,000-100,000 euro mold investment upfront. Denis calculated he’d need to sell about 4,000 units to break even.
This is where I started to see the real problem. Denis was thinking like an engineer - focused on manufacturing costs, materials, and production processes. But as we talked through what investors actually want to see, I realized something important.
“My assumption is that marketing and public stunts and PR campaigns is not your forte. Is that correct?”
“Not my forte in the sense that I’m not particularly good at doing this, but also I don’t hate doing this.”
That “not hating” marketing was crucial. Most engineers I work with have an almost allergic reaction to anything that feels like promotion or publicity.
The more I thought about Denis’s product, the more I realized we were looking at this completely backwards. This wasn’t really a transportation device competing on convenience and price. This was something with massive cool factor potential.
“You’re talking about it as a transportation device, but I’m thinking of this more as a fashion accessory. It is... it can become a very quirky, cool sort of thing to do. You know, like, the Vibram Five Fingers shoes. They’re not particularly convenient, they hurt your toes, but they’re very distinctive, and for a period of time, it created a sort of movement of people who wanted to show that off.”
The shift in framing was dramatic. Instead of solving a problem, Denis was creating a statement. Instead of competing on utility, he could compete on uniqueness and status.
This led us to a completely different approach to solving the funding problem. Instead of trying to prove market demand through pre-orders, what if Denis could demonstrate marketing potential through influencers?
“If you were able to convince five people, maybe even in the fashion space, or in the sports space, or in some extreme sports space, people who use scooters to do tricks... and you convince them to use your device, to film themselves on it, and to project enthusiasm about it, then first of all, you may immediately get some traction and interest from the general public. But also, even without that, just a testimonial from 3, 4, 5 people like that should convince some investors.”
The strategy started to crystallize: instead of raising 200,000 euros for full production, Denis could raise maybe 10,000 euros to create several prototypes specifically designed as marketing tools. Send them to influencers, generate buzz, and use that social proof to convince investors that the marketing risk - the real risk - was manageable.
But Denis raised an important concern about his current prototypes.
“The thing with the not pretty enough is that it’s really not pretty. My experience as a software engineer, people do not understand in their minds the concept of, it’s going to be better in the final version. Like, no matter what, they will see the flaws, and then you tell them it’s going to disappear in the final version.”
This is such a common problem. Engineers see past the rough edges to the underlying functionality, but most people can’t make that leap.
I suggested a two-box approach: send influencers both a working but ugly prototype and a beautiful but non-functional mockup. But then I had a different thought.
“For a certain audience, an ugly thing can be a fashion statement as well. I think that is part of the point. Instead of trying to hide the ugly, you emphasize the ugly, because then it shows you are ahead of the curve. You’re doing something that nobody else has ever done, right?”
This reminded me of early Tesla prototypes or SpaceX engines - all exposed wires and rough edges that screamed “this is the future, just not polished yet.”
We also talked about a “two-phase commit” approach to investors - a concept Denis immediately grasped as a software engineer. Get multiple potential investors interested, then ask one to go first in exchange for better terms, using that commitment to secure the others.
“You have multiple people with skin in the game who have an interest to be consistent with their prior decisions. And possibly influencers who are interested in what you’re building. And you sort of start the flywheel.”
One complexity we hadn’t anticipated was regulatory. Electric personal mobility devices face a patchwork of laws across different countries, cities, and states. In some places they’re legal, in others forbidden.
“In the Netherlands, you cannot ride a skateboard. Like, an electric skateboard, it’s forbidden. Like a solo wheel, it’s forbidden, too, because it doesn’t have handlebars.”
But this constraint actually supported our influencer strategy. The regulatory complexity meant Denis needed to start with buzz and awareness anyway - building demand that could eventually influence policy.
As our conversation wound down, I could see something click for Denis. The shift from thinking about prototypes as engineering tools to thinking about them as marketing tools was fundamental.
“It’s very interesting, like, I really like what we discussed and what you proposed, that prototype as a marketing tool. It was already partially in my mind, but not fully realized, the way you presented it, of actively using that prototype and building it in some way to the marketing department. Like, for me, it was still an engineering tool that was showing to the purpose, so making them not with the purpose of experimentation, but with the purpose of communication.”
The Catch-22 that Denis came in with - n…
I sit down with Surhail, a founder from Pakistan living in Germany who’s building iMentor - an online accelerator for entrepreneurs rejected by traditional programs.
While his heart is in the right place wanting to help the 97% who get rejected, we quickly discover a fundamental problem with his business model. People who apply to accelerators are looking for free money and support, not to pay €150 per hour for mentorship.
We explore the psychology of startup founders, why they’re incredibly tight with spending, and how his matching service might work better if he stops positioning himself as serving “rejects.”
In this episode, I sit down with Dennis, a 20-year-old founder from Ukraine who built Hustle Advisor, a social network for entrepreneurs with paid advice features. Dennis has attracted 4,000 visitors but only 100 registered users, and he’s struggling with the classic cold start problem that plagues all marketplaces.We dig into why his platform feels empty despite having users, and I walk him through the solution that successful companies like Facebook, Tinder, and Uber used to overcome this exact challenge.The answer involves dramatically narrowing focus and compressing time, but Dennis discovers something unexpected about his current users that shines an interesting light on this problems.
FULL RECAP
“There’s only 100 users on the platform and the biggest struggle is probably getting more users,” Dennis said, his frustration evident even through our video call from his chilly house in Chester.
Dennis is a 20-year-old Ukrainian entrepreneur who moved to the UK three years ago because of the war. He’s built what he calls “Reddit for entrepreneurs” - a social network where experienced business people can post advice behind a paywall. Despite having 4,000 visitors in the past month according to Cloudflare, only 100 people had actually registered. Even fewer were active, and the paid content barely moved.
Listen to the full session at “Finer Live” on Spotify, Apple Podcasts, or at finereli.substack.com/podcast.
I asked him who he considers to be actual users. “A user is anybody who registered. Some of them are active, they post, they comment, they do anything else that they are supposed to do. It’s like Reddit, but specifically for entrepreneurs. And besides that, you can also do like paid posts on it,” Dennis explained.
I’ve seen this story before - the ambitious young founder who’s built something that should work in theory but struggles in practice. What Dennis didn’t realize yet was that he’d stumbled into one of the hardest problems in the business: the marketplace cold start problem.
“So you’re a marketplace of two different things,” I told him. “One, is you have marketplace of content and wisdom and community and the sense of friendship, camaraderie, that arises of that. And two, you have a marketplace of paid info products and paid content.”
The issue became clearer as we talked. Dennis had created a double bind - a catch-22 that plagues every marketplace founder. To attract content creators, he needed an audience willing to pay. To attract paying customers, he needed valuable content creators. Without enough of either, both sides remained unsatisfied. And his solution to add a free tier wasn’t actually moving the needle on where revenue would come from.
...
“Do you feel it’s harder to attract sellers or buyers?” I asked.
“Sellers. It’s more difficult to attract a seller, because a buyer is basically a regular user who just wants to know something,” Dennis replied.
This was the key insight. Dennis had users who wanted to learn, but he couldn’t attract enough people with expertise to share. The few creators he’d managed to bring over from other platforms posted content that didn’t get much traction, creating a vicious cycle. What he didn’t say, and didn’t realize yet, was that the free users may not end up buying anything even if there was enough paid content.
“You have sort of a double bind or a catch-22,” I explained. “In order for the paid features to work, you need a lot more people, and currently your unique proposition is that you have paid content. But because you don’t have enough paid content and enough paid content creators, and you don’t have enough of a user base willing to buy, you sort of have two problems that depend on each other.”
Dennis’s eyes lit up with recognition. This was exactly his problem - he couldn’t attract more people without having more paid content, and he couldn’t attract more creators without having more users to buy. It’s called the cold start problem of social networks, and it’s notoriously difficult to solve.
...
“The real answer has to do with niching down very, very narrowly,” I told him. “So if you get two creators focusing on a particular type of content that is relevant to a particular type of stage in entrepreneurship, and is written in a particular format with a specific style and specific vibe; and you get 10 people who are in that stage, who typically consume content in that format, who are interested in those things; so you have 2 creators and 10 potential buyers - you have a chance of a deal.”
This is how every successful marketplace has started - not by trying to be everything to everyone, but by solving a very specific problem for a two very specific groups of people - buyers and sellers - who met each other in the same place and at the same time. Uber famously started with a handful of drivers at one intersection in San Francisco on one Friday night, the same spot where lots of people were looking for a ride home.
“I have never thought about that, actually. That’s a really good idea. I think I’m going to do that,” Dennis said, the energy returning to his voice.
The breakthrough moment had arrived. Instead of building a platform for “entrepreneurs” - a group so broad it’s meaningless - Dennis needed to find a tiny slice where he could predictably create matches.
...
“There has been a post not a long time ago. There was a guy asking a question about his SaaS. He asked how to monetize it. Because apparently he has a lot of users, but all of them are free,” Dennis recalled when I pressed him to think about the conversations already happening on his platform.
“That’s it. That’s all you need. That’s your niche,” I told him. “There’s one guy on your platform who is asking how to monetize a popular free SaaS. If you choose your niche to be about how to monetize free apps with a lot of free users, and you manage to get two or three people who have some ideas about how to do that, and you manage to get a few more people with successful free SaaS offerings, then you have a conversation about a real thing.”
This problem - having lots of free users but no revenue - affects thousands of software founders. It’s specific enough to create focused conversations, but common enough that Dennis could find people on both sides: founders struggling with monetization and experts who’d solved this problem before.
“I would just go to specific subreddit and search for people who ask similar questions to that and contact them in like DMs, ask them, would you like to participate in this?” Dennis said, already thinking through the tactics.
...
“In order for deals to happen, people from both sides need to be at the same place with complementing desires, at the same time,” I explained. “An event is sort of a mental state. It has a beginning. It has an end. It has a focus. It has a bunch of participants. It has an intention.”
The solution wasn’t just about finding the right people - it was about bringing them together at the same moment. When everyone is actively engaged simultaneously, conversations spark, questions get answered immediately, and real connections form. This compressed timeframe and laser focus is what creates the nucleus that can eventually expand.
“The cold start problem is not an easy problem. It’s a hard problem. It’s actually the hardest problem in building a marketplace or a social network. Because once you solve that, you have a ton of other problems, but you’re not trying to figure out if this should exist or not. You’re trying to figure out how to grow it, which is a different spot to be in,” I told Dennis.
But there was hope in this difficulty. The beautiful thing about online experiments is that failure is invisible. If Dennis picked a topic, set a time, tried to bring people together and it didn’t work, he could simply try again next week with a different focus. Each attempt would teach him something new about his users and their needs.
...
The cold start problem has humbled countless entrepreneurs, but those who solve it often b…
In this episode, I talk with Anna about her biggest challenge: finding leads for her service helping SaaS companies fix their crucial first five minutes of user experience.
Anna felt trapped by productivity culture, forcing herself to be consistent when she naturally works in intense creative bursts followed by rest periods - like a lion.
We explored how she could embrace her natural work rhythm instead of fighting it, turn her love of introspection into authentic marketing, and find high-value clients during her creative spikes rather than grinding for leads every month.
But then Anna realized something that changed everything about how she saw herself and her work...
(The episode title is a nod to Robert A. Heinlein’s “specialization is for insects” quote)
"It's actually to find the challenge," Dima said, his voice carrying a weight that surprised me. "That's the challenge now."
We were about twenty minutes into our conversation when he dropped this line. Dima is a successful solo entrepreneur - he's built a profitable software business, achieved financial independence, has a family he loves. By most measures, he's won the game. But here he was, describing his biggest problem as not knowing what problem to tackle next.
"It's a good problem to have," I acknowledged, "but it's still a problem."
"Yes, and I noticed, you know, it's like in support," Dima continued. "You try to close every possible ticket, but you will never close all tickets. There was a problem like, I need to have this money to cover my lifestyle. And then I reached this goal. And now I see, oh, okay. But it opens new problems like, what's the challenge?"
This hit me as profound - the endless nature of human problems, how solving one level reveals entirely new categories of challenges. Most entrepreneurs never reach this particular problem. They stay trapped in the survival game, always needing the next milestone to keep the lights on. But Dima had broken through to something else entirely.
...
"So the big question is, what's next?" I asked. "Or maybe, is there anything next? Is there a point where you can just literally relax, drink beer, watch football, and that's it? Or does life lose meaning if you don't have a big, audacious goal to chase?"
"I don't think that having a meaning in life is mandatory," Dima replied. "But I feel it really helps to answer why you wake up in the morning. I have some fears, you know, like if I don't do anything at all for a long period of time, I feel I might degrade, degenerate, and probably I won't be a nice person to hang out with."
We were dancing around something bigger here. Dima had inadvertently stumbled into a preview of humanity's future. As I listened to him, I realized he'd created his own post-scarcity environment - enough money, enough freedom, enough security that external pressures no longer drove his decisions. And with that freedom came a distinctly modern form of existential crisis.
"The reason I think your question is so important," I told him, "is that as humanity, it seems like we're edging closer to all of us having the same question. There's this theory that AI will solve all of our material problems, and then we will live in a society of infinite abundance. What I see is an explosion of depression, because the transition from 'I have to do things' to 'I actually don't have to do things' - well, that kind of situation produces this question: So what do I do?"
...
"We have annual inflation every year," Dima observed, "and even just this one factor forces me to not stay still and to make more money, and to make more money, I need to bring value to people. It's like baseline meaning for life that the system gives you."
"Like a built-in motivation," I agreed.
"Yes, and within a certain margin of error, you are in a state of abundance, sort of post-AGI abundance," I continued. "You created it for yourself. There's enough degrees of freedom in the world right now for certain individuals with certain skills to be able to create it for themselves. And you have."
This was the crux of it. Dima wasn't just dealing with a personal career transition - he was grappling with questions that our entire species will face as technology eliminates scarcity. The challenge isn't just finding the next challenge; it's learning to derive meaning and motivation from internal rather than external sources.
...
The conversation took an unexpected turn when Dima started talking about football. He told me about a recent game where a new, highly egotistical player joined who only wanted to score goals himself.
"I felt a little bit hurt, like my ego felt it's not good. I also want to score some goals," Dima admitted. "But then I thought, wait, wait, wait! Do I want to win, or do I want to score goals? What do I really want?"
"So I completely changed my game. I went to defense, and I was playing like 100 percent, just taking the ball from everybody and giving this guy passes. And he scored a lot of goals. We won every game that day, like no losses at all. And for me it was kind of a revelation."
This story revealed something crucial. The joy Dima found wasn't in individual achievement - he'd already mastered that in business. It was in the collaborative dynamic, the team adjustment, the shared victory. He was describing the exact opposite of the solo entrepreneurial path that had brought him success.
"It feels like too much time spent alone," he said. "Years, you know."
"Maybe what happened is that you've exhausted your capacity and need for selfishness and isolation," I suggested. "You've done for yourself, by yourself, and you want to collaborate with other people."
"Yes, I see it pretty clearly," Dima responded. "I love some kind of collaboration towards a shared goal. I feel it's actually - I probably understand it now when we were talking - like building something and achieving it with somebody."
...
That's when I said something I'd never said to anyone before: "Maybe what you're looking for is a job."
"Whoa!" Dima exclaimed.
I was as surprised as he was. Here I was, talking to a successful entrepreneur who'd built his own business and achieved financial independence, suggesting he consider employment. But the more we explored it, the more sense it made.
"Obviously you will never have a job in the same sense that you've had jobs before," I clarified. "It will always be more of an agreement between equals, because you have achieved equality status. But maybe this is terrifying because you're thinking you need to build a team of 10 people. Who said you needed to build a team? You just want to be on one."
"You're right. Precisely. I don't want to be managing people. I want to just play with a team," Dima agreed.
The shift was remarkable. We'd gone from his original framing - wanting to build a company of 10 people - to realizing he simply wanted to be part of something larger than himself. The courage required wasn't the courage to build or lead, but the courage to let go of existing identities and join something.
...
"But if you apply to a job without needing the income, and you apply because of the specific desire to work with interesting people on valuable problems, you're looking for a team you would like to play with," I explained. "This can never result in a suffocating agreement, because it's an agreement between two parties that voluntarily enter for the purpose of making something better together."
"How do you find something like that?" Dima wondered.
"It's a next step question," I replied, "because something happens when we're clear about what we're looking for. An hour ago, this was not part of what you thought you were interested in. Even if it crossed your path, you would not see it."
This is how breakthroughs work - not through force or analysis, but through conversation that reveals what was already there, waiting to be acknowledged.
...
"Thank you that you picked this one, caught this one," Dima said as we wrapped up. "When you're in your mind, you see it and you're like, oh no, I don't want to even go this direction, because it's so huge. But you forced me to talk about it, to clarify it a little bit, and to see it from this different perspective, which is crazy - to go back to 9 to 5."
We'd started with Dima saying his biggest challenge was not knowing which challenge was next. We ended with him having a specific, if surprising, direction to explore. Sometimes the answer isn't about finding something completely new - it's about rediscovering something familiar from an entirely different vantage point.
For the full conversation and to hear how this unfolds, search for "Finer Live" on Spotify or Apple Podcasts.
"My biggest challenge with this is monetization as well as motivation," Yair said, his voice carrying the weight of six months spent building something that users loved but wouldn't pay for.
I was talking to Yair, a young entrepreneur who had quit his job nine months earlier to build Nomadlio, a free alternative to Nomad List. He had 3,000 monthly visitors, positive feedback, and a technically superior product with four times more data than his competitor. Yet he was struggling with the classic indie hacker dilemma: great product, no revenue, dwindling motivation.
"Is it free because you wanted it to be free? Or is it free because you were worried you wouldn't be able to ask for money for it?" I asked.
Yair explained his reasoning: "When Peter made the move to lock down Nomad List and make it essentially completely pay... he got a lot of hate for it. I was thinking of it being free as a really good way to differentiate."
"You're not competing with Nomad List, you're competing with Peter Levels, who is a pretty good software engineer. But he is a phenomenal marketer," I pointed out.
This hit at something deeper. Yair had fallen into the trap many technical founders face - thinking that a better product with more features would naturally win market share. But markets aren't always rational, and free doesn't always solve the distribution problem.
...
The conversation shifted when Yair described his monetization strategy: funnelling Nomadlio users into Stay Match, an AI tool that finds Airbnbs based on specific criteria like proximity to gyms or quiet neighbourhoods.
"Right now we have 3 customers that paid $100," Yair said. "A lot of people ran scans... 15 people out of them. One person bought. But everyone received pretty good results. They're just not converting."
"There's a profound difference between a person who paid you something once, and a person who tried something you've built for free once," I explained. "When you do it for free, you're sending the wrong signal."
This was revealing a fundamental mismatch. Nomadlio attracted budget-conscious nomads looking for cheap destinations. But Stay Match was trying to sell time-saving automation to people who valued their money more than their time. These weren't the same customers.
"You're attracting people who are budget conscious in the first place," I said. "You're sort of attracting the opposite of what you're looking for."
...
We dug deeper into why automated solutions face resistance, even when they solve real problems.
"People are not jumping all over it saying, 'Take my credit card,'" I observed. "When this happens, it basically means we have the wrong model of the world, or in particular, we have the wrong model of what's going on in the other person's mind."
I shared an example about my father, an engineer who refuses to order groceries online because he needs to "feel the tomatoes." The same psychology applies to travel booking - people want control over decisions that feel important and personal.
"For them, it's possibly just part of the fun. Part of the journey. Part of the joy of nomading," I suggested. "You might be offering to take away something that they actually value and ask money for it."
This struck at the heart of Yair's challenge. He had built a solution for his own problem - as an experienced technical nomad who had developed clear criteria for choosing accommodations. But most people don't think systematically about their preferences, and many actually enjoy the research process.
...
The breakthrough moment came when we discussed why people weren't converting after trying the free sample.
"Maybe they didn't really define what they were looking for correctly," Yair realized. "If you use the defaults, you're not gonna get personalized results."
This reminded me of Netflix's onboarding: "They don't let you get anywhere until you tell them 3 shows that you like. The reason they do this is that if they don't, I will get recommendations that I don't resonate with at all."
"Maybe there's a product thing here," I suggested.
Yair had been focused on making his form comprehensive, but comprehensive forms with defaults often produce generic results. Users would get recommendations that didn't match their unstated expectations, then assume the product didn't work.
...
We pivoted to discussing what made Stay Match truly unique - its ability to filter for things no other platform could find.
"Give me an example of a unique thing you can filter on," I asked.
"Ergonomic chair," Yair replied.
"Perfect. That's specifically for people who are expecting to work remotely," I said. "If there is an image with the desk and the ergonomic chair, and it says 'Airbnbs with proper work setup in Madrid,' and you click it, and you get a list... that is mind blowing because you can't get that list anywhere."
This was the key insight. Instead of trying to recreate Airbnb's entire filter system, Stay Match should focus on the impossible-to-find amenities: ergonomic chairs, quiet neighborhoods, reliable wifi, nearby playgrounds. These weren't just features - they were solutions to problems people didn't know could be solved.
"You basically want the experience of a person coming in, clicking a button, and seeing something they get excited about," I explained.
...
Our conversation concluded with a discussion about pricing psychology and business models.
"It doesn't make sense for me to pay a monthly thing for it... but of course I'd pay if you help me do it better," I said, describing how a pay-per-search model might work better than subscriptions for occasional travelers.
"There is something about the mechanics of the first use. When you do it for free, you're sending the wrong signal here."
Yair's journey illustrated a common pattern in product development: starting with your own problem often leads to the right solution but the wrong go-to-market strategy. Technical founders assume other technical people are their market, but technical people often prefer to build solutions themselves.
"So many things," Yair reflected at the end of our call. "You really blew my mind with this conversation. The main takeaway for me is understanding that if people didn't buy, it's not for a mysterious reason. It could be the price, the commitment, or the misalignment between their expectations."
He was ready to put Nomadlio in maintenance mode and focus on Stay Match with a clearer understanding of his real value proposition. Sometimes the most important realization is knowing which problems are worth solving - and for whom.
The conversation reminded me why I love these sessions. It's not about having all the answers, but about asking the right questions to help entrepreneurs see their own blind spots. Yair left with clarity about his next steps, and I was reminded that the best products don't just solve problems - they solve problems people didn't know could be solved.
To hear the full conversation and others like it, search for "Finer Live" on Spotify or Apple Podcasts.
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