How’s the family doing?
Everyone is doing very well! Thank you!
What is it like having three kids?
It’s both delightful and extremely difficult.
People ask a lot how it feels playing zone defense rather than man-to-man. As a basketball fan, I enjoy this analogy, but I don’t think it quite captures the experience.
I think it’s more like juggling.
You start off with your first kid, and it’s like, “OK, here’s this tennis ball. Your job is to throw it up in the air and catch it thousands of times each day. DO NOT DROP IT.” And, purely on a mechanical level, it’s not super difficult. But it’s very stressful because you are constantly worried about dropping it.
Then you have a second kid, and suddenly you’re juggling two tennis balls instead of one, and that’s SO MUCH HARDER that it makes you want to burst out laughing when you hear first-time parents complaining about how hard it is to juggle (which I was certainly doing after my first!)
Then you have your third kid, and part of you is thinking, “This isn’t gonna be too hard. After all, going from two balls to three can’t be as challenging as going from one to two. Plus, [whispers] it’s OK if you drop one every once in a while.”
And this would be true, except it’s no longer just tennis balls that you’re juggling. Your first tennis ball has transformed into a 16-ounce claw hammer, and the second tennis ball has (briefly, you hope) transformed into a machete. And the machete and the hammer constantly fight with each other … as you juggle them.
The difficulty isn’t just the number of kids. It’s also their constantly changing natures!
(BTW, the newest tennis ball is absolutely perfect in every single way. She has started smiling and has, occasionally, slept for 10-hour stretches at night, which is a miracle that was neither deserved nor expected.)
What's been your favorite thing about paternity Leave? And other than the obvious, what will you miss most?
Favorite thing – watching my five-year-old and my three-year-old learn how to play together. They still fight constantly, but there has been a huge increase over the last couple of months in cooperative imaginative play, and it’s been a delight to watch.
Non-obvious thing that I will miss the most – the time spent outdoors. I try to get outdoors as much as I can in regular times, but it’s so much easier to do when I’m spending all day with my kids (who love being outside).
Did you have any time to consume non-fintech content during your leave? Any favorites you’d like to recommend?
I did! Not as much as my wife, who heroically took (and continues to take) most of the night shifts with the baby, but I did manage to watch a few things:
- The Great – it’s a dark and hilarious dramatization of the rise of Russia’s Catherine the Great in the late 1700s. Nicholas Hoult is absolutely unhinged (in the best possible way) playing Peter III.
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Silo – grabs you by the lapels in the first five minutes and literally doesn’t let you go. Magnificent.
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Star Trek: Strange New Worlds – my single favorite show right now. They just started season 2, and it is absolutely brilliant. It might be the best Star Trek show ever, which is a crazy thing to say, I realize, but wow, is it good.
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Bluey – my kids have been watching it for a while, but I’d never really sat down and watched any until recently. Incredible. More episodes are dropping on Disney Plus soon. For real life.
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Spider-Man: Across the Spider-Verse – one of two movies that I managed to see in theaters during paternity leave (the other was the new Transformers movie, which delighted my five-year-old, but probably won’t delight you). Across the Spider-Verse is a work of art. Truly. You don’t even have to care about Spider-Man to enjoy the animation, but if you do like Spider-Man, you’ll probably agree with me that this is (along with its predecessor) the best that superhero movies can be.
Best thing to watch after a long day of chasing kids?
I wanted to answer this question separately from the one above because “exhausted after chasing kids around all day” is a very specific mental state, and it’s not well-suited to every type of show. Slio, for instance, would be a very bad choice.
My two recommendations would be Abbott Elementary and Primo. Both are sweet, funny, and easy to follow without having to pay super close attention. You can find Abbott Elementary on Hulu and Primo on Amazon Prime.
How did you manage the content lifecycle as a creator while out on leave?
The goal was to keep my regular newsletter cadence (every Monday and Friday) going for the two months that I was out.
To accomplish that, me and the team at Workweek focused on prepping as much content in advance as possible. This included essays that I had been meaning to write for a while, guest essays, and collaborations with other writers.
If I had followed the plan as written, that would have taken care of 100% of my content needs for the last two months. However, as a lifelong procrastinator, I couldn’t make it quite that easy on myself. I got about 70% of my content written in advance, and I left the remaining 30% for myself to write during any available downtime (of which there was a surprising amount … babies sleep a lot!)
The end result was perfect for me. A mostly relaxing leave with just enough work to keep my (sleep-deprived) mind engaged.
A special thanks to my Workweek teammates Anushka, Esper, Brett, Ari, Patrick, John, and Nick for their invaluable help in making my paternity leave plan a success. You guys are the best!
What were your favorite newsletters that ran while you were out?
The ones that I got to collaborate on with other people were my favorites. Kristen Anderson’s essay – Found & Lost: Losing Your Identity as a Founder – was exceptional, and the Q&As that I did with my Workweek colleagues Nick Van Osdol (A Fintech x Climate Tech Crossover!) and The Wolf of Franchises (A Fintech x Franchises Crossover!) were really fun.
Of the ones I wrote myself, my updated list of fintech resources, and my essay – Birkin or House? – were my favorites.
What’s your go-to recipe for impressing people?
Pork tacos. You take a pork shoulder, crisp up the outside in a frying pan over high heat with a little olive oil and salt, and toss it into a slow cooker with beef stock, water, tomato puree, malt vinegar, maple syrup, a few cloves of chopped garlic, and a shot of dark rum. Let it cook on low for 6-8 hours, pull it out and separate out the fat, shred it, and then serve up whatever taco fixings you please.
The best recipes for impressing people are the ones that are secretly easy, but that appear difficult from the outside. If your guests don’t like it, no worries. You hardly did any work! If they do like it, you worked tirelessly on it all day! Win-win.
How are you feeling about the Celtics?
Game 7 against Miami still hurts, although I don’t think anyone was beating Denver this year. I’m personally devastated by the Marcus Smart trade, even though I acknowledge that, on paper, it was a good trade, and I think it should make the team better. My biggest concern for this coming season is injuries. We’re going to need some luck to keep Rob Williams, Malcolm Brogdon, and Kristaps Porzingis all healthy.
What’s the most underrated city in Montana to visit?
Dillon. Beautiful scenery, copious outdoor activities, and surprisingly good restaurants for such a small, out-of-the-way town.
What was the most interesting fintech news that happened while you were out?
Consolidation in the BaaS platform space.
I figured it would happen at some point, but multiple acquisitions (Rise, Bond) and a bankruptcy (Railsr), all within a very short period of time, caught me by surprise. Feels like the rock is really rolling down the hill now, and it’ll be interesting to see what other companies may end up getting hit by it.
Jason Mikula and I talked about this a bit in our most recent Fintech Recap podcast, which drops next week!
What’s the near/medium-term catalyst for P2P payments (Block, PayPal)? The Covid pull-forward seems to have run its course.
Agree that the Covid surge is definitely over.
I don’t see another similarly-big catalyst for growth coming anytime soon. Instead, I would expect to see a bunch of smaller, more incremental innovations drive usage, including the continued expansion of P2P tools into B2C disbursements and small business/independent worker payments (this is an area Zelle is focused on) and the broadening of P2P payment mechanisms (such as the ability to send people stocks, crypto, charitable contributions, etc.).
How do you see the corporate card space evolving? How will the competitive dynamics between fintech companies and traditional bank issuers evolve?
Well, first, I think it will become increasingly untenable to just offer a corporate card. Some companies in the space will evolve in the direction of becoming more full-service business banks, with a broad portfolio of financial products. Fintech companies taking this path will compete with the traditional banks that are already serving their target segments (although they likely won’t all have as easy a time displacing their bank competitors as Mercury and the other business neobanks focused on startups have had in displacing SVB).
The other direction will be evolving into full-service SaaS vendors, focused on expense management and other back-office functions where corporate cards can act as a ‘skeleton key’ for unlocking 10x experiences for employees and finance teams. This is where Ramp is focused and where Brex is going. It’s also what Navan is doing, although they’re playing a slightly different game.
And that brings me to my second prediction – expense management will become increasingly verticalized. As generalists like Ramp, Brex, and Airbase continue to converge on a similar feature set, the question will be, how do you stand out in the expense management space? My guess is that we will see new competitors offering workflows that are tailored to specific industries. We already see this trend manifesting in a few industries, like healthcare, construction, and shipping/logistics. We will see a lot more.
What will be the biggest success and failure in fintech 12 months from now?
Biggest success – I think we will see a big-time exit for a later-stage fintech infrastructure company, likely acquired by a legacy bank technology vendor.
Biggest failure – I predict that we will see significant regulatory action taken against 1-2 big players in the partner bank/BaaS space. The regulatory actions taken to date will pale in comparison.
Fast forward two years from now – what impact will generative AI have had on the financial industry?
It won’t be obvious to outside observers, but back-office operations at big banks and other large incumbents in the financial industry will be much more streamlined, everything from customer service/support to internal knowledge management. This will result in slight (not massive) decreases in total headcount at these companies, but also much more engaged and satisfied employees.
If you were a fintech founder today, what problem area would you build in/for?
I’ll give you two different answers.
If my goal was to maximize my odds of ending up a rich, successful ex-founder, I would build something around open banking. There’s still tons of opportunity, whether it’s building out the analytic and decisioning layers in the open banking stack (who will be “the FICO of open banking”? is an interesting question) or expanding out the bottom layer in that stack (another interesting question – what will be the next payroll API-type opportunity?) The tailwinds for people building in this space are just incredibly strong, and I don’t see that changing for the foreseeable future.
If my goal was to build the fintech solution that I personally feel the most passionate about, I’d build a neobank for teachers. Teaching is the only white-collar profession that doesn’t pay white-collar money. Teachers make 81 cents on the dollar compared to white-collar professionals with similar experience and credentials, and that pay gap has tripled in the last 20 years. There is a huge opportunity to help the 3.5 million public school teachers in the U.S. better manage their money and build wealth (income smoothing, debt refinance, retirement saving/investing, etc.) There’s not a huge appetite from VCs for niche neobanks these days, but I think it’s absolutely needed.
What do you have planned for Fintech Takes now that you’re back?
Lots of stuff!
The newsletter, obviously. Plus, the Fintech Takes podcast, will be back up and running next week.
Then we’ll have some new, spin-off podcast series, a monthly Fintech Takes virtual event, a paid community for fintech professionals (would love to hear your ideas for what you’d most want to see from a Fintech Takes community), more educational content and courses (including refinements and additions to the Fintech 101 Course), and, of course, I’ll be attending and speaking at multiple fintech conferences this fall, including Finovate and Money2020.
I can’t wait … and thank you all for waiting these past two months for me 🙂
