ClearFind

James Leifeld is a serial entrepreneur who had already founded 14-15 businesses across fintech, co-working, and other sectors before starting ClearFind. His background—from growing up in a working-class family in Hull, Yorkshire where his parents were hustlers and wheeler-dealers, to working for Richard Branson at Virgin—had instilled in him an entrepreneurial DNA. The idea for ClearFind emerged from his experience building Rise, a fintech innovation lab in partnership with Barclays that became the world's largest of its kind, operating in seven countries for nearly a decade.

When James started ClearFind in 2017 (moving to New York specifically to play the VC game), he identified a massive problem: nobody truly understood software at a feature level. While platforms like G2 Crowd offered star ratings, they were useless for strategic decision-making—a farmer in Minnesota's five-star review meant nothing to a Coca-Cola executive. James realized businesses were bleeding money on redundant tools they didn't even know they owned.

For three full years, ClearFind didn't try to make a single dollar. Instead, James bootstrapped the entire operation with $3 million of his own money, building a proprietary dataset on software features that no competitor—not Gartner, not G2, not Google, not Accenture—possessed. This was the hard problem that needed solving. Most VCs wouldn't have been patient enough, but James's conviction and capital allowed him to pursue a multi-year moonshot.

In October 2023, ClearFind finally went to market. The response was immediate: enterprises were over the moon. The conversations were different from typical B2B pitches—prospects weren't skeptical; they were relieved someone had solved this problem. The company quickly landed marquee clients including Airbnb, Zoom, and Slack. What surprised James was that the original use case (helping companies find new tools) wasn't what resonated. Instead, enterprises wanted ClearFind to audit their existing software and tell them what to eliminate—which software was redundant because its features were duplicated elsewhere.

James's biggest insight was being willing to pivot when the market spoke. His original hypothesis—that companies wanted help matching with new tools—turned out to be wrong. But because he'd built something with unique data, he could shift the value prop: instead of "find new tools," it became "eliminate waste and consolidate your stack." This is something only ClearFind could do.

Interestingly, consulting firms now use ClearFind to serve their own clients, creating a B2B2C distribution channel. James notes this is far more effective than traditional software audits.

As of the podcast (likely late 2024 or early 2025), ClearFind is in active fundraising. James has invested $3 million of his own capital over 2.5 years and is now seeking VC backing—but on his terms. He's critical of VC dynamics, noting that VCs actually prefer founders who raise early and dilute themselves rather than bootstrap successfully. He views it as a rigged game: play by the rules (raise early, let them take their percentage) and you get access to the network; solve the problem yourself and they resent that you don't "need" their money.

James is adamant that he won't disclose exact revenue numbers yet, partly as a negotiating tactic with VCs. The company is clearly gaining traction with enterprise clients, but he's focused on playing the longer game: ensuring that when he does raise, the valuation and terms reflect the reality of what he's built and that he emerges better off than he would have bootstrapping indefinitely.