Fintech Player Comps (The 90s Edition)
Happy Friday, Fintech Fans!
Jayson Tatum may return tonight, after spending the last 10 months diligently rehabilitating from a torn Achilles tendon. I vividly remember watching him tear it last year and feeling like I had just gotten hit by a bus (I can’t imagine how he felt).
So, I’m a little nervous. Excited, but nervous.
As such, it feels appropriate to revisit a recurring Fintech Takes gimmick in today’s newsletter. Credit to Dan Swislow for the 90s inspiration.
- Alex
P.S. — My colleague Kiah is writing a report on how modern tech is reshaping commercial fee income and treasury services. To do this well, we need a little more input from people who live in this world.
If you work in treasury management or commercial banking (or can forward this to someone who does!), could you take this survey we've put together? We'd truly love your input.
It’s anonymous, all multiple choice, and should take ~5 minutes. Plus, as a thank you, we’re doing a few random cash drawings and even giving away some Fintech Takes hoodies. I can confirm they're very nice.
You can respond here.
Fintech Player Comps (The 90s Edition)Copy anchor linkCopied
I never thought I’d say this, but the 90s are back!
While I was living through it, I don’t remember thinking, “wow, this is the peak of culture.” But Gen Z has spoken, and they have declared (through their allegiance to baggy jeans, CDs, and Friends) that the 90s were, indeed, peak culture. All we can do is accept it.
Indeed, even basketball (objectively the greatest sport in the world) is getting in on the 90s nostalgia. This week, NBC did a “throwback” broadcast of the Spurs – 76ers game, complete with Bob Costas, Doug Collins, Mike Fratello, Jim Gray, and a 1996 graphics package that was absolutely delightful to revisit.
So, in honor of that, I’m going to compare fintech companies to 90s NBA players (if you’d like to read my previous NBA player / fintech company comps, they're available here and here).
A few notes before we get started:
- I will be using players from the 1992/1993 NBA season and fintech companies from 2026 for these comps. I would have used fintech companies from 1992/1993 for this list, but fintech wasn’t really a thing at the time! (Capital One was spun out of Signet in 1994)
- Much like my logo rankings, these comps do not necessarily reflect my personal feelings about either the companies or the players. Companies and players I like will get unflattering comparisons and vice versa.
- Most importantly, please remember that this is a silly and subjective exercise. While I spent more time doing research for this than I’d like to admit, there are no right or wrong answers. Take no offense at any of the comparisons!
And now [Roundball Rock music]: Ba-ba-ba-ba-ba-ba basketball! Gimme gimme, gimme the ball! Because I’m gonna… DUNK IT!!
Robinhood — Charles BarkleyCopy anchor linkCopied
Having the best season of his career. Frontrunner for the league MVP (even though everyone knows he’s not the best player). Efficiency / expected value leaves a lot to be desired, but it is undeniably effective. Has a deeply problematic relationship with gambling.
Stripe — Michael JordanCopy anchor linkCopied
Ridiculously talented and well-rounded. On a generational hot streak. Constantly (but quietly) working the refs.
Stripe’s renewed crypto push reminds me a bit of Jordan’s baseball detour — an interesting side quest from the best player in the world. Hopefully, it goes better for Stripe than that season in Birmingham went for Jordan.
Mercury — Hakeem Olajuwon Copy anchor linkCopied
Started out playing a different sport (soccer for Hakeem, mobile gaming infrastructure for Immad Akhund). Got into basketball / fintech and showed early promise, but his volatility caused lots of clashes with teammates and referees. Has shown recent signs of maturity and may be on the cusp of greater success.
(NBA / Fintech Nerd Note — in the early 90s, Olajuwon embraced his faith more deeply, legally changed his name from Akeem to Hakeem, and began studying the Quran daily, which brought him to a state of "unbreakable calmness". I imagine that the OCC hopes Mercury has achieved a similar state.)
SoFi — Patrick EwingCopy anchor linkCopied
Extremely good — All-NBA good — but you can’t help feeling like he’s not the ideal avatar for ultra passionate Knicks fans / retail SPAC investors.
Chime — Karl MaloneCopy anchor linkCopied
Puts up a drama-free 25 and 10 every night like clockwork, but somehow still sparks endless arguments about whether he’s actually that good. Needs a good point guard / bank partner to do what he does.
Block — Larry JohnsonCopy anchor linkCopied
Does everything. Plays in the post. Faces up. Handles in transition. Shoots from the perimeter. A back injury / corporate bloat has made him less effective, but perhaps AI can fix it?
Not known for spending his money wisely. Unimpeachable impact on the culture.
(NBA / Fintech Nerd Note — It should be stated that none of the merch that Cash App has produced comes close to touching that Hornets starter jacket.)
Ramp — John StocktonCopy anchor linkCopied
Very smart. Technically proficient. Optimizes every possession. Believes in keeping expenses low. Revered by coaches / Keith Rabois, even though the casuals might not know him. Will help you negotiate your next contract!
Capitalize — Scottie PippenCopy anchor linkCopied
The very definition of “switchability”. Beloved teammate. Needs a more talented co-star to reach his full potential.
Adyen — Arvydas SabonisCopy anchor linkCopied
The stats and the eye test tell you that he is one of the best players at his position (maybe the best), but he is based overseas, so no one cares.
Affirm — David RobinsonCopy anchor linkCopied
Believes in better living through mathematics (Robinson majored in mathematics at the U.S. Naval Academy). Technically proficient and dedicated to making sure his team doesn’t get scored on / pay interest. Has a reputation as a Boy Scout.
Bilt — Tim HardawayCopy anchor linkCopied
Signature move (the UTEP Two-Step for Hardaway, rewards on rent for Bilt) is so effective that it doesn’t really matter that the rest of his game is a bit one-dimensional. The move is also impossible for competitors to copy. Bad at defense / customer service.
(NBA / Fintech Nerd Note — Hardaway’s son — Tim Hardaway Jr. — has built a good career in the NBA as well, which rhymes a bit with Bilt because its founder and CEO, Ankur Jain, also has a rich and famous father who played a role in his son’s success.)
Kalshi — Dennis RodmanCopy anchor linkCopied
Only does one thing, but is so relentless at it that he warps the geometry of the game when he’s on the floor. The way he markets himself publicly is completely unhinged. A frequent target of lawsuits. Well known in Las Vegas.
Rain — Shawn KempCopy anchor linkCopied
Kemp’s nickname was “Reign Man,” so this one was easy. Young. Clearly ascending. Needs to stay out of foul trouble.
PayPal — Kevin McHaleCopy anchor linkCopied
An absolute legend who helped define the last era in his industry. Now severely hampered structurally, and looking like he might be at the end of his career.
(NBA / Fintech Nerd Note — I feel terrible for this comparison. I’m a huge Celtics fan. My dad spent a large part of my childhood reenacting McHale’s unstoppable post moves on me in our backyard. He is important to me, and this comp is mean … but also accurate. He was washed in 1992/1993 and retired after a heroic playoff loss to the upstart Hornets. Here, let’s all make ourselves feel better by watching some highlights from his prime.)
Column — Mark PriceCopy anchor linkCopied
Quiet. Short / small number of employees. Not terribly athletic, but very technically proficient. One of several players who were a bit ahead of their time (shooting threes for Price, vertically-integrated BaaS for Column).
(NBA / Fintech Nerd Note — This profile on Column and William Hockey is worth reading.)
Capital One — Dominique WilkinsCopy anchor linkCopied
Older and less explosive than these kids running around, but has reinvented his game (Wilkins acquiring a better outside shot and a post-up game, Capital One acquiring Discover and Brex) and is still producing at a really high level.
(NBA / Fintech Nerd Note — Dominique’s nickname was “The Human Highlight Reel,” which was well-deserved. He was absolutely incredible, and his duel against Larry Bird is one of the greatest things that has ever happened in the history of the human race.)
Erebor — Shaquille O’Neal Copy anchor linkCopied
A rookie who has already made a huge splash. Extremely difficult to referee fairly. Infrastructure may need to be hardened to account for his style of play. Has gotten way more money from sponsors / investors than rookies / de novos usually get. Not at all shy about publicity.
(NBA / Fintech Nerd Note — During the 1992/1993 season, there were three instances where games had to be stopped due to damage to the baskets. Shaq, in his rookie year, accounted for two of the three. Seriously, look at this. I mean, what?)
Klarna — Derrick ColemanCopy anchor linkCopied
Immensely talented, but frustratingly inconsistent. Is difficult to categorize. If you’re planning to give him a large amount of money, be careful.
Coinbase — Gary PaytonCopy anchor linkCopied
Bald, penchant for trash talk, probably at his best while trying to stop other, better players.
TomoCredit — Chris Washburn Copy anchor linkCopied
Difficult to tell if his poor results are due to laziness, entitlement, or stupidity. One of the biggest and most embarrassing busts in the history of his industry. Exiled from the big leagues, but still hanging around on the fringes.
MORE QUESTIONS TO PONDER TOGETHER
Big news for the endlessly curious (yes, you): I’m collecting your fintech questions on a rolling basis.
What’s keeping you up at night? What great mysteries in financial services beg to be unraveled? Think of it this way, if a stranger is a friend you just haven't met yet, your question is a Fintech Takes conversation waiting to happen.
One that could headline a Friday newsletter or be answered in an upcoming Fintech Office Hours event.
Drop your question here, whenever inspiration strikes!
Thanks for the read! Let me know what you thought by replying back to this email.
— Alex
Join 2,444 other finance and fintech leaders in the Fintech Takes Network
The conversation doesn't have to stop here
Keep learning and connecting in the Fintech Takes Network
EVENTS | FEED | LIBRARY | DIRECTORY
