Now, as an operating partner at Infinity Ventures, Ansari is bringing that experience to a market facing its toughest test yet.
“The exits have been drier than at any point I’ve seen in my venture career,” he told me. “The M&A pipeline is quieter than ever, and that’s forcing FinTech founders to grow sustainably and prove they can be profitable.”
A Different Kind of Cycle
Ansari has seen market corrections before, but this one, he said, “feels different.” The days of fast money and faster valuations are gone. “Buyers now want profitable targets after years of funding cash-burning models,” he explained.
Infinity Ventures invests at the seed and Series A stages, where acquisitions are the typical outcome. And where, he says, they have slowed to a crawl. “Private equity firms have picked up a few smaller public FinTechs,” he said, “but M&A has been very, very quiet.”
Still, he sees opportunity in the quiet. “FinTech is regulated for a reason,” Ansari said. “You can’t hack your way around licensing or compliance. It takes years — not months — to build correctly.”
Rolling Up Sleeves — Not Just Writing Checks
Ansari said Infinity’s real value is in its approach. “We don’t just invest — we roll up our sleeves,” he told Webster. “We help founders with fundraising, introductions and capital planning.”
That hands-on model reflects Ansari’s own playbook, honed through decades of investing and advising startups across multiple cycles. “Venture isn’t zero-sum,” he said. “Most deals you can do with your friends.”
Founders, he noted, increasingly want investors who’ve been there. “Helping them think through tough decisions with pattern recognition — that’s what matters.”
Where the Next Wave Breaks: B2B Payments
Infinity Ventures is betting big on B2B payments, the next frontier for FinTech innovation. “B2B is a much larger space than consumer,” Ansari said. “It’s still old-school — checks, invoices, PDFs.”
He pointed to Coast, a portfolio company simplifying payments for fleet operators. “They’re targeting HVAC, plumbing and electrical companies,” he said. “Those businesses run on credit cards and invoices, and we’re modernizing that.”
The opportunity extends across treasury management, receivables, payables and CFO tools. “If you’re an SMB, you don’t have a CFO,” Ansari noted. “You need software that fits your business.”
Copycats, Cycles and Staying Power
Trends come and go, Ansari said, but great founders persist. “It’s like when two asteroid movies came out at once,” he joked. “Suddenly, everyone’s chasing the same idea.”
What matters most, he added, is execution. “Great founders have what I call ‘rizz and aura’ — they can attract capital, talent, and trust. Ideas are cheap. Execution and scale are what matter.”
And that conviction comes from experience. “Let’s not overly glamorize the business,” Ansari said. “You’re dealing with companies that go under, founders that leave, sometimes even fraud. You have to hang in there.”
Looking Ahead
Ansari expects the next 18 months to bring clarity. As recently-public FinTechs stabilize, he believes renewed M&A and innovation will follow — especially across back-office finance.
He’s pragmatic about hype cycles like AI. “Of course it’s a bubble,” he said. “Ninety percent of AI companies are overvalued and 10 percent are undervalued. The challenge is knowing which is which.”
Still, his tone remains optimistic. “Someone’s going to solve it,” he said. “And multiple companies are going to solve it. That’s what keeps me excited.”
From Venture Veteran to Builder’s Ally
Ansari’s journey, from early-stage investor in the icons of FinTech to operating partner at Infinity Ventures, mirrors the industry’s own evolution. The easy money may be gone, but for founders who can execute, adapt and endure, he says, the best opportunities are just beginning.