Tarpit Idea
I had been thinking about pivoting for a year, but convincing my co-founders was hell. Every time I brought it up, my team would point to our existing user base as a signal of market validation.
True, there were signs of success on Clustr, where web3 novices could manage their cryptocurrency portfolios without doing a bunch of their own research. We had revenue. We had 9,000 users, and the average user session ran nearly 10 minutes.
What we didn’t have was stickiness.
We couldn’t get users to transact on our platform. Most would use the insights we provided and then bounce, buying and selling their crypto elsewhere.
To address this and scale up users and transaction rates, we ran more than 150 creative marketing experiments. Some worked. Most failed. We were left with two options: gatekeeping our content or monetizing through ads, neither of which we wanted to do. We understood then that we couldn’t sufficiently scale the product in the way we had envisioned.
So we shut it down.
Alone in Pivot Hell
I knew deep inside that we needed to change course a year before we did. But as CEO, I didn’t put my foot down and make a conclusive decision. Sometimes you just have to piss your team off. The buck stops with you, so everyone will blame you for the wrong decision either way.
Looking back, I can see why the team was so reticent to reevaluate our approach. To keep our burn low, I would need to let most of them go. From a powerful 12, we suddenly became a team of 4, half of which signed off a month later. Only two of us remained. Me and Arthur, who has both tech brains and a reality-check mindset, and would always keep me grounded over the coming months when we discussed wild new ideas.
Though I know most of the Clustr team likely didn’t feel the same way, I felt relieved after closing—as if a huge weight had been lifted off my chest. I could finally breathe knowing I had the creative freedom to pursue literally anything, within any industry.
But that was a double-edged sword. According to Y Combinator, good ideas take at least a year to generate.
How much freedom could I take?
Generating Ideas
After we started thinking of ideas for a new venture, we attended YC Startup School (SUS) in London, which energized us. We thought we could get an MVP rolled out in a few weeks.
But weeks turned into months. We were deep in pivot hell, looking at dozens of ideas and hundreds of successful startups across multiple industries. We exhausted all the experiments for finding good startup ideas that [YC group partner] Jared Friedman talked about and were desperate.
So I decided to fly to San Francisco. No plan. Just looking for inspiration. Little did I know that those five days would change our lives.
I was blown away by the warm welcome from fellow AI-startup founders, the folks across Big Tech, and YC. Despite reaching out on very short notice, so many people made the time to connect—grabbing coffee, brainstorming ideas, and just having real, open conversations about where the tech industry is headed and what life is like in SF as a founder. That openness and willingness to engage is truly something special and unique to this city.
So I reached back out to Tom from SUS London, who told me to come in for a 20-minute walk around SF’s Dogpatch neighborhood. That meeting with Tom was truly inspirational. We discussed our approach to generating ideas until finally he said, “Moving cautiously kills startups.”
I flew back and immediately jumped on that advice:
I spent the next two weeks conducting 54 interviews with field experts, their clients, and startups, further validating the problem we’re hoping to solve. (Sorry, no details—we’re stealth.)
We secured two advisors to help design the product.
We closed a pilot with three companies.
We started developing our MVP.
Tom’s advice made me realize our biggest mistake had been not creating momentum by being too cautious when considering new ideas. Momentum creates information, which helps you fall down the right path, which funny enough led us to YC S25.
Into YC
We set the YC application deadline as our deadline to get something off the ground. Boy, did it help.
A week or so after applying, YC invited us to interview. To get ready, we ran prep interviews with some of the top YC alumni we knew. Even [Product Hunt CEO] Rajiv stepped in to help.
When the day of the interview came, our nerves were high, but we were confident. Two partners joined the call, and the tennis match began. We gave short, concise, and comprehensible answers to each of their questions. The next day, we received a phone call with an invite to the summer 2025 YC batch. I couldn’t believe it! Something that I had been striving for over the last three years had suddenly become a reality six applications later. All it took was giving up on the tarpit idea I had been clinging to.
The lesson: Be ambitious yet grounded. Don’t go for the classic tarpit idea being pitched by literally hundreds of founders at YC startup school.
Success in this new endeavor remains a long way away, but the one thing I’m confident in is our speed of iteration and momentum. Always keep your momentum high because any information is good information. Even if it’s telling you it’s time to get out of the tarpit.
Tim Cherkasov is the former CEO of Clustr, a web platform that “provides novice crypto investors with fundamental metrics.” His new company is in stealth.