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.
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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.
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“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.
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“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.
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“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.
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“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.
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The cold start problem has humbled countless entrepreneurs, but those who solve it often build the most valuable companies in the world. Dennis now has his roadmap - find a specific problem, gather the right people, compress the timeline, and create that first spark of genuine value exchange.
