"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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