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 that would tell him whether his business was viable.
“Yeah, for sure. I mean, we already have a product, we’ve already decided that this is the direction that we’re trying to move in, and it doesn’t cost a lot to accomplish.”
“Okay, well... I’m going to get you off this call right now so you can go and use the time we have left. You can go and do that, because it takes 20 minutes to send all these messages.”
This is the moment that separates entrepreneurs from hobbyists. Paul had all the tools he needed - a working product, paying customers as proof of concept, a clear niche to test, and a network to tap into. The only thing standing between him and definitive market feedback was the willingness to reach out and risk rejection.
As we ended the call, Paul committed to spending the rest of the day reaching out to his network. Within hours, he’d know whether cybersecurity was a real opportunity or just another engineering distraction. By putting himself out there, he’d trigger what we jokingly called “the algorithm of the universe” - the mysterious way that focused action attracts the exact opportunities you need.
Sometimes the biggest breakthrough isn’t building the right feature. It’s having the right conversation.
