“[IPOs] generate liquidity for the investors and the employees, who can then use that cash to invest in new companies or start new ones. It has this virtuous flywheel multiplier effect.”
Kamran Ansari, who previously invested in companies with Greycroft and Headline VC, made the move this month to Infinity Ventures as venture partner, where he will help source and support fintech and infrastructure investments.
The new role not only pairs him with long-time friend and Infinity co-founder Jeremy Jonker, but also bulks up the firm’s presence in New York City.
Infinity Ventures was spun out of PayPal Ventures in 2021, and Jeremy Jonker, Jay Ganatra, and Mario Ruiz announced their first fund of $158 million in 2022. The second fund of $184 million closed in 2024.
Prior to venture capital, Ansari was head of corporate development and strategy at Pinterest, where he was one of the first outside hires for the role and led nine acquisitions for the company, including Jelly, URX, and Instapaper. He also helped prepare the company for its 2019 IPO. In late 2021, it was rumored that PayPal was interested in acquiring Pinterest, but talks fizzled out.
Meanwhile, Ansari and the Infinity founders have known each other for more than a decade–dating back toAnsari’s career as principal and venture partner at Greycroft. They worked together on investments in Venmo, Braintree, and more. Ansari and Jonker continued that relationship with monthly calls to collaborate on their co-investments in Rainforest, Pagos. and Vinyl Equity.
“Kamran’s focus on fintech infrastructure and commerce enablement aligns perfectly with Infinity’s mission,” said Jeremy Jonker, co-founder and managing partner at Infinity Ventures. “Having both led corporate development teams at prior stops in our career, we have followed parallel paths that now converge at Infinity. I could not be more excited to continue building the future of fintech together.”
Future Nexus spoke to Ansari about building his career, including one of his unique first jobs; his decision to join Infinity, hot fintech investment prospects, and why he likes stablecoins.
This article was lightly edited for length and clarity.
One of your first jobs was at the Disney Feature Animation Studio, and I thought that was a really unique path. Tell me about how you kind of landed there.
I grew up in Burbank, which is where Disney is based, with a Disney family. My father worked at Disney, and The Walt Disney Corp. helped pay for my college. I’m greatly indebted to them.
In the summer of 1997, I interned at Disney in the animation studios, which is where they make the feature animations for theatrical release. That summer, they had just released “Tarzan” and “Mulan.” The department I was in was called Creative Developments, which is where they do all the brainstorming, ideation, and initial sketches for characters, cartoons, and storyboards.
My job was to take down the storyboards from the prior shows and then help create the new storyboards with the animators and artists for what became the “Emperor’s New Groove” and “Atlantis.”
It was a really cool experience. I always loved creativity, technology, and media, but it made me realize I didn’t want to live and work in Hollywood.
How did you then end up in venture capital?
With that interest in technology and digital media, I went to college, and when I graduated, I worked at McKinsey for a couple of years, focusing on that sector.
When you finish the analyst program, most people go to grad school or go on to work at hedge funds or private equity. I was the one weirdo who went to work at a tech company. It was a small software company in New York in advertising technology that was what I considered web 1.0. This was before Google was really established as an advertising player.
That is where I saw myself transitioning more to the software and technology side as an operator. It ended up being the first of three different operating roles I’ve had over the years, where I got to be in the weeds of a technology company, as opposed to just messing around in them.
I then did end up going to grad school at Stanford, which started my Silicon Valley adventure.
You’ve worked with the Infinity Ventures team for over a decade and in different roles. How did the venture partner opportunity to join them come up?
Jeremy and I co-invested in a number of companies together, including Rainforest, Pagos, and Vinyl Equity, and others. The last five years, we have worked more closely together.
Last year, when the company raised the second fund, they were looking to bring on somewhere else in a venture partner capacity to help them with relationships, branding, and marketing, and to get more presence in New York. They already had one partner in New York, but they thought it’d be useful to kind of increase the visibility there. It was fortuitous and timing, but it’s been a long time in the making.
Over the past decade, you’ve been following fintech. Is there anything that stands out to you as kind of significant milestones in the growth of the industry?
One is certainly the maturation of the 1.0 fintech companies, the two most famous of which are probably PayPal and Square. They have been in the public for 10 to 20 years, and they have a long roster of alumni, acquisition units, and venture units. Those companies are more established and have set the stage for 2.0 companies, like Coinbase, to be public.
There is this sort of transitioning from the original fintech company to the next wave, which includes more crypto businesses, like Circle. That is a path where additional businesses will be built and grown because there is a precedent and an ecosystem behind it.
And by the way, the reason that helps is because once it is an established company, then you have, importantly, expertise. You have alumni networks — people who have grown up in the industry that then identify new opportunities and leave PayPal or leave Square to start something new. That cycle is now in full effect in fintech, and we are seeing second and third generation companies.
Another big milestone is the development around blockchain and crypto.
Since you referred to crypto and blockchain in this way, do you see that as the next wave of fintech innovation?
There are a couple of things that are either here, depending on what you ask, or arriving soon. One is everything in and around stablecoins, cryptocurrencies, tokens and blockchain. Some of it has been interesting, and some of it has been, in some ways, still fringe or more suited to particular types of companies or investors, but not necessarily embraced by the mainstream.
Stablecoin represents an evolution of the blockchain and crypto universe that seems to be more suited to the mainstream. That is resulting in a bunch of companies built around leveraging stablecoin infrastructure to do things like currency exchange, cross-border transfers, interbank transfers, credit cards, business credit, you name it. That’s a frontier that is quickly developing.
The other, which is a bit more further down the line — TBD really — which is everything around agentic AI payments and what that’s going to look like. We’ve seen some examples, like using an AI agent to automatically manage your treasury for a company, rebalance between different currencies and cash to maintain your deposits the way you want. Another potential use case is leveraging agents to do your accounts payable or manage payroll.
Part of me is like, “oh, yeah, that’d be really cool. It makes sense.” And another part of me is like, “what exactly is that? Is that just a way to do it? Is that replacing the employee that did that before? How big of an advance is that really? Do we need it?” We’ll see.
What do you consider to be your sweet spot of fintech — what’s most attractive to you?
Fintech is a super category, and there are four areas I consider pillars of fintech. One is payments, which is the longest-running. It’s a good tech industry. It’s been around the longest, and it’s the most successful. It monetizes well and lends itself to technology and digital transmission. The others are lending, asset management, including wealth management, stock trading and then insurance. I definitely invest across all of those.
The area within payments I’ve seen the most heat for the last few years, is everything around commercial and business plans, so B2B payments is still very much under technology creativity relative to consumer.
Think about all the largest companies you’ve heard of in fintech — they really do two things: One is to help consumers pay other consumers, peer-to-peer, and the other is to help a consumer pay to a business. This is Venmo, Stripe, Braintree.
However, they don’t help, by and large, businesses pay other businesses. This is still done through a hodgepodge of different services, some of which are digital, but a lot of which are just PDF invoices, paper checks and checks sent from a bank. The largest kind of digital B2B payments company around is Bill.com, with a $10 billion to $15 billion market cap company.
I’ve invested in a number of companies that do that. One of them is Rainforest which does a decent amount of B2B payments and processing, although they do consumer as well. I’ve also been on the board of Credit Key for many years, and that is a B2B version of Affirm or Klarna. B2B is where the bigger opportunity is because the consumer side is pretty mature and there is not a lot of white space left.
In a recent panel that you were on, you were saying that, “getting into deals was the easy part, but finding liquidity and exits, particularly for modest outcomes, is the hard part.” Why is that the hard part?
Venture investing is not like investing at a hedge fund where I buy shares of Nvidia, and if I want to sell tomorrow, I just sell it. In venture, exits are relatively rare. Most venture companies fail or don’t return capital.
The real returns are driven by a very, very small number of companies, some of which IPO. And those IPOs are extraordinarily rare. In the entirety of the U.S. stock market, there are around 4,600, compared to hundreds of thousands of venture-backed businesses.
Instead, M&A is really the lifeblood of the venture business, and it too is hard. It’s most likely a structured transaction, a private deal, infrequent, they’re heavily negotiated, and they’re relationship driven. These things don’t happen overnight. It takes a lot of time and effort.
And while it may not economically move the needle that much for a VC fund, it’s meaningful for the founders. Those companies, even with a modest outcome, it behooves you as a venture investor to spend time on those and to try to find landing spots for those companies as well.
Why? It generates a return. It’s meaningful for the founders and the employees. In the venture business, there are some deals where you make your reputation, and some deals where you make your return. Reputation is often built on those deals that are in the middle.
Speaking of IPOs, what are your thoughts on the comeback of fintech IPOs this year?
It’s great. It’s hugely important for the ecosystem because without it, the entire flywheel gets clogged. IPOs, which maybe people don’t necessarily realize, are an overall kind of marketing event with great visibility and branding for the sector. Most people don’t pay attention to companies until they’re public, saying, “If I can’t buy this stock, why would I pay attention to the sector?”
It brings a lot of attention to these companies and to the sector. It generates liquidity for the investors and the employees, who can then use that cash to invest in companies or start new ones, and it gives those companies a public currency.
In addition, it gives them a stock that has value every single minute to compensate employees, but also to buy other companies. They can use that stock to do M&A or purchase some of these venture-backed businesses that need an exit. It has a virtuous flywheel multiplier effect that we haven’t had, frankly, for the last little while.
We are always talking about valuations. You were on Bloomberg saying that “2020-2021 valuations need to be adjusted. Both Klarna & Chime reset valuations to pursue public listings.” Can a startup reset valuation similarly without it looking negative?
It’s actually somewhat easier and cleaner to take the valuation write-down and adjustment when you’re a startup and/or still private, and in fact can then pave the way for the public or for a trade sale/exit.
Klarna did a valuation reset from $39 billion to $40 billion to $9 billion in a private round two to three years back. It was perceived as a negative at the time and did receive mixed coverage, but ultimately has been a good strategic move.
In terms of it not seeming like a negative, there’s no “good time” or easy way to reduce your valuation or do a stock reset. It will almost always have a negative connotation to it, and there’s no two ways about it. In early stage venture, it’s called doing a “down round.”
Down rounds are painful for founders, VCs/investors, and the regular employees, as everyone gets diluted and their equity is worth less. But it’s also often necessary to position the company for additional capital-raising and future growth. Some of the biggest and best companies have done it. For example, Facebook famously had a down round from a $15 billion valuation to $4 billion at one point.
