Year One! 🎂 🥃

It's been a extraordinary first year for Fintech & Finance! Thank you!

Hey friends -

It's Fintech & Finance's first birthday! 🥳 🎂 🍹

I want to share with you the journey, and what a journey it's been. This started out as a weekly letter with multiple topics and has evolved into a regular deep dive on financial services, two podcasts, and several other exciting projects.

It's been a success beyond anything I had planned because of you, my readers. Your feedback, engagement, and sharing are what keep me writing every week. You could spend your time in any number of ways and you choose to spend a valuable portion of it with me each week, whether that's reading first thing when you get into the office or listening in the car on the way home. Thank you! 🙏

In this week's letter:

  • Fintech & Finance's first birthday: where it started, what it is today, how I write & record, and where it'll go from here

  • Facts, figures, and links to keep you thinking over a drink

  • It's nothing fancy, but it's my all-time favorite. The Manhattan.

Total read time: 20 minutes, 2 seconds.

🎧 Funders & Founders Episode #4! 🎧

Episode #4 is Brand Building with Matt Mullenax, Co-Founder and CEO of Huron.

Listen on Spotify

Matt’s stories of what it means to deeply understand your customer are eye opening. They recently had an order for twelve travel sized kits. It’s a ridiculous number. They reached out to the customer and found out he had purchased them for his groomsmen. Not missing a beat, Jonny at Huron tracked down the registry and bought the newlyweds a wedding gift! And they’ve got the thank you note to prove it!

The thank you note to prove it!

Listen on Apple Podcasts

Also available everywhere podcasts are found.

52 Letters Ago

Fifty-two letters ago, I was leading a fintech startup and had recently bought my first apartment together with my wife. I set out to do something utterly bewildering to me.

To write.

I've never been a writer so my goals were simple - write weekly and spark conversations. It was the opening to the very first letter:

This is the first in what will become a weekly letter. The world's an endlessly exciting place and pandemic life stymied our conversations exploring mostly useless knowledge and wide-ranging musings. I hope these letters spark conversations we might not otherwise have had and perhaps leaves you thinking a little differently about the world.

With your help, Fintech & Finance has succeeded beyond my wildest hopes:

  • Grown from 68-person friends and family readers to almost 700 subscribers and over 1000 readers every week.

  • Published over 480,000 words. That's two Ulysses, the first four Harry Potters, or 60% of the King James Bible.

  • Recorded 30 episodes - over 20 hours! - of the Fat Tailed Thoughts podcast with my friend and colleague Steven Dickens.

  • Turned my startup conversations into a podcast called Funders & Founders - with new episodes booked every week for the next 6 weeks and many more yet to be scheduled.

  • Started working with exciting startups and analyst firms like Futurum to produce tailored content to support their missions.

I'd like to share with you what worked, how I work, and what I've learned. The place to start is at the beginning because, despite it all, I still don't think of myself as a writer.

480,000 Words Later, I'm Still Not A Writer But I'm Learning To Become One

Writing never came easily to me.

The surprise my high school English teachers would have to find that I now write regularly would only pale in comparison to their shock (and perhaps horror) that anyone would read such stilted prose. And yet, here we are.

I'm not the writer I was then and I'm certainly not the writer I was in college - that guy only wrote lab reports painful to read even by the standards set by academics. I'm not even the writer I was a year ago.

Fast forward to today - my fifty-third letter - and I'm different. A different person, a better thinker, and perhaps not yet a good writer but certainly a better one. I'm still in the apartment with my wife, but I'm no longer with the startup. The letter has changed and grown, as have I with it. It's been an astonishing journey I've only been able to accomplish with your help.

What you may not have realized, what you may not have felt as one of those initial sixty-eight subscribers, was the utter uncertainty as I promised a weekly letter and conversations. I committed to weekly - publicly - because I knew I'd let myself off the hook without it. I hoped for conversations so I wouldn't just be shouting into the ether.

It was the first of many lessons I've taken away.

Lesson #1: commit publicly and just do it. You have something to share. Committing publicly will hold you accountable. Just doing it will help you find whatever "it" is if, like me, you're not quite sure where to begin. You'll be wonderfully surprised at the engagement and support from friends and strangers alike.

Your readers will vote with their eyeballs

It's surprisingly easy to figure out what's working - just track the eyeballs and engagement. Despite spending the majority of my waking hours thinking about various corners of financial services, it took you voting with your readership for me to recognize that was where I'd find my voice.

My initial letters were on how the internet works and vaccine production. They're interesting topics, but they don't form the basis of something repeatable for me. In the hands of a different person with different interests, either could be a footnote in a broader and deeper exploration of another corner of the world.

I love telling stories and I get engrossed in the minutia of how finance works. Focusing on that as the theme helped me discover my voice as a writer. It's the same as how I speak when I get overly excited explaining some esoteric, often not all that important detail that nonetheless grabbed me so I just have to share.

It's there that I found engagement and readership. More of you read each letter and you increasingly wrote back to continue the conversation. I found kindred spirits equally interested in understanding financial plumbing. Many of you pulled in even more readers until, to my astonishment, there were more of you who I had never met before in person than there were ones I had. All united by an interest in the topic at hand.

Friend of Fintech & Finance James Abels (🍻) caught onto this earlier than I did. He read some of my earlier, internally published works at my fintech startup. He grasped much earlier than I did what you all voiced with your reading habits - what I write is far more engaging when it's something close to my passions. He helped push me to write and share more broadly (thank you 🙏!).

As I published more and you read more, I discovered an unmet need. There are great publications about the future of finance, what's going on today in fintech, the structure of markets, and so much more. Very few, however, consider financial infrastructure as it exists today and wonder how we got here. Without that grounding, innovation can be blind hope. With it, you can chart a path forwards that doesn't require "burning down the establishment" to craft a better system.

Lesson #2: write about something that interests you, that will keep you coming back week after week. The internet's a big place. If your passion shines through, and you listen to your users' feedback, you'll find your niche. At internet scale, even the smallest niches are huge.

Meet people where they are & get them hooked

Despite being a digital native, I don't feel at home on social media. Before Fintech & Finance, I was at best a lurker and more often not present at all. My Instagram feed is fairly representative of my entire prior experience - started for me by my wife during the pandemic and still only pictures of cocktails.

Substack makes it easy to deliver my letters straight to your inbox, but it's not particularly conducive to conversations. I love our one-on-one emails as you push me to think more deeply about a topic, but I regret that they can only ever be between the two of us. They don't leave space the way a cocktail hour does to join a group, already deep in conversation, because you overheard something that piqued your interest. Social media, for all its faults, can be that virtual venue.

Twitter and LinkedIn are those venues for Fintech & Finance. LinkedIn is now home to over half of the subscribers. Friend of the letter Dominic Poon (🍻) has started conversations on almost every letter posted to LinkedIn. His extraordinary background in design brings a unique perspective to financial services that I don't always consider at the depth that I should. I learn something every time he replies and love that I get to do it alongside everyone else in the conversation.

I'm still very much learning how to share and participate, and I'm incredibly encouraged by the results. Fintech & Finance friend Mark Paulis (🍻) suggested I look into TikTok. To say it's foreign is an understatement - I've never so much as downloaded the app. But I now understand there are people for whom that short video clip format is the ideal way to get hooked.

A year ago I don't think I would've thought twice before writing off TikTok. Now I'm actively investigating it, trying to better understand the medium so that I can position the Fintech & Finance content in a way that fits. Just last week, I caught up with a comedian who grew his following from nothing to over 30,000 during the pandemic almost entirely through TikTok.

It's part of a strategy that recent Funders & Founders guest and friend of Fintech & Finance Matt Mullenax (🍻) already employs successfully at men's care startup Huron. I challenged him why a company with such a strong brand and such engaged customers would sell on Amazon. Matt taught me a deeply important lesson:

We just want to own your bathroom. So if you choose to buy an Amazon, go for it. If you choose to buy from our site, terrific. Hopefully, in the not too distant future, we're on shelves in places. If that's your preferred mode of shopping more power to you. Because our goal is to get product in people's hands.

I'm excited to figure out how to package what I produce in new ways to engage new subscribers where they want to consume it.

Lesson #3: meet people where they are and deliver the same high-quality product to them the way they want to consume it. They'll reward you with higher engagement rates and will pull in new circles of people who otherwise never would have discovered your content.

Sausage Making

This letter, the podcasts, the other content I produce... it's a lot. When it was just the letter, I could procrastinate and produce willy nilly. To keep up a weekly schedule AND produce more AND continue to improve the quality meant building processes.

I don't know that I'd recommend my processes, but they work for me. What's been most powerful is checklists. Where I can, I also automate routine steps like publishing to What follows here are my processes for the letter and the podcasts, and the tools I use to get it done.

This may get into a level of detail that's uninteresting to you. If so, feel free to skip. These are operations and tools I had to discover for myself. Had someone published a similar guide before I began, it would have saved me many hours.

Letters: from idea to publishing to sharing

Everything starts in Airtable. (If you're not familiar with Airtable, think: Excel. Close enough.)

James Abels (🍻) suggested I assemble an editorial calendar. It's one of the best suggestions anyone has made to me in a long time.

An editorial calendar is a loosely committed list of topics that can guide future content. I keep a running list of anniversaries, events, and more in Airtable that provides a starting point for future letters. I don't always stick to it. Oftentimes something will grab my interest - like Packy McCormick's Tokengated Commerce - and I find myself compelled to respond.

30-day view of the editorial calendar themes.

Topics come from far and wide. I endlessly peruse announcements from startups, regulatory filings, and financial news. Twitter has surprisingly become a major source of inspiration. There's a wonderful community of finance, fintech, crypto, and regulatory practitioners eager to engage in thoughtful conversation. Everyone from startup founders to billionaire financiers and world-renowned academics joins in.

Anything that piques my interest - like a recent thread on Payment for Order Flow - gets added to the editorial calendar. It's materially simplified my search for topics. At any given time, I have 50+ to choose from organized by date and cross-referenced by themes, each of which links out to the original source inspiration.

Once I put a publication date against a chosen topic in Airtable, automations take over. They create a series of checklists that keep me organized and ensure I actually get the letter out on time, with cocktail talk and a cocktail, and then share it on social media.

The to do list for this letter!

Lesson #4: Offload mental clutter to checklists and inventories. It'll help you produce high-quality output more consistently and focus on what really matters. Pilots use checklists. Physicians use checklists. Charlie Munger recounts how a physician prep checklist to wash their hands properly reduced Michigan ICU infection rates by over 66% in just the first three months. Use them - they work.

Then the actual work of writing begins. Writing can take anywhere from three to four hours and up to double that. Topics like last week's Banking as a Service that require disparate resources tend to take longer. More focused topics like Buy Now, Pay Later with just four major vendors in market tend to take less time.

It takes me a while to start writing. I'll often commit to starting first thing in the morning and find myself with no words on the page come lunchtime. But it's not time wasted - once I start writing, I write uninterrupted until the story's on the page. Most of the prep time is spent reading until I've developed a coherent narrative in my mind. From there, it's cataloging the sources, quotes, images, and key facts I'll use to assemble the article.

To be clear - I would struggle to do this in a domain where I don't already have a firm grounding. Most narratives are incremental - they build on knowledge I already have.

The particularly exciting ones (for me anyhow) are when I discover that I don't have the depth I think I do and when my mental model is simply wrong. My recent foray into Buy Now, Pay Later is a good example of both. I didn't understand how they made money or their credit exposures and I do now. It's immensely fun to discover how much more of the world there is to understand.

Evernote is the home for all of my writing. There are newer tools and probably better tools, but this one serves me just fine. I have a template with placeholders for the letter sections and social media posts. Any resources I intend to use are dumped haphazardly at the bottom under a section titled "research." Most of my diagrams are made in Keynote or PowerPoint.

Once the body of the letter is written, I pull in the cocktail talk links and a cocktail. Like the letter topics themselves, I keep running inventories to be used in future letters. It speeds up each letter and helps me avoid using the same link or drink in multiple letters. We're at 53 different cocktails and counting!

The tastiest list.

I pass each letter through Grammarly before I proofread it myself. Grammarly picks up on spelling and basic grammar issues, but it doesn't solve for structure or coherency. I find it more efficient to solve the easy stuff first so I'm not distracted as I consider more substantial edits.

Edited letters move onto Substack where I schedule them for publication at 6am ET. The text formatting and email distribution are all handled by the app. Recently, I've increasingly made use of Canva for the thumbnail image that shows up in Substack and alongside the social media posts. It's a simple but effective tool with a robust catalog of built-in elements that I can stitch together into a new image.

I made a graphic.

Every letter that I publish triggers a Zapier automation that grabs all of the letter data - publication date, the letter itself, the thumbnail image, and all of the metadata. It pushes that data to Airtable for my review. If it looks good, I hit a "publish" button and it's instantly published to via another Zapier automation. I built and hosted the website using Webflow.

I use Hypefury to queue tweets sharing the letter, the cocktail, and the cocktail talk. I found myself getting endlessly distracted down the Twitter rabbit hole whenever I went to post them on Twitter. Hypefury, as a separate app with a scheduling function, saves me from myself.

LinkedIn is the real pain. The publication tool doesn't play nice with anything. I copy-and-paste the letter over to LinkedIn, re-upload every single image, and reformat the thumbnail image to fit the LinkedIn picture dimensions. It's a process but I haven't found a better solution.

I keep email notifications on for every interaction and comment anywhere the letters are posted. The joy of engaging hasn't diminished even as it's grown. That said, I have had to set up email routing rules to save my inbox.

All in all, it's twelve different tools and twelve steps from start to finish.

So. Many. Tools.

Once published, it's on to the next one. Airtable automations move completed letters out of the queue, tee up the next one, and the process starts anew.

Podcasts: from idea to publishing to sharing

Two important thank you's before we dive in. My co-host Steven Dickens (🎧), #53 on the list of top tech analysts and host of I am a Mainfraimer, is the one who encouraged me to do a podcast in the first place. He got me going and I continue to learn more from him every episode about how to host. We have a lot of fun each week on Fat Tailed Thoughts. Thank you for the push! 🙏

Second - thank you to Fintech & Finance friend Matt Reustle (🍻), CEO of Colossus, the startup behind Invest Like The Best, Web3 Breakdowns, and a number of other great podcasts. Responding to my cold outreach, Matt spent over an hour detailing the intimate details of how the company produces its podcasts. It's invaluable knowledge that jumpstarted my efforts.

I'm a huge fan of all of the shows and continually aim to produce with the quality that Colossus does. Thank you, Matt! 🙏 Readers - go check out what they produce!

My process for podcasts is a derivative of the Colossus process. There's material overlap with my letter process, but the podcasts involve more tools and more steps.

Every episode again starts Airtable with an editorial calendar and tables for organizing episode info - and lots of automations.

The initial guests on Funders & Founders were my personal connections but are increasingly recommended by past guests. The guests are smart, interested, and interesting people building and funding world-changing startups. It should come as no surprise that their close connections are cut from a similar cloth. Every guest I've had - without exception - has been wonderfully generous in introducing colleagues to come onto the show.

Lesson #5: seek out interesting and interested people. Ask what they do, how they think, and what motivates them. You'll find yourself engrossed in conversation, and a good conversation is one of the great joys in life. When someone's passionate, they love to share that passion with others who are genuinely interested. It can lead to even more great conversations if you just ask. The joy of building and learning is infectious.

Like with the letters, Airtable kicks off a task list once a podcast is scheduled. Production and post-processing is a multi-step process and the checklist length reflects that.

A lot goes into a podcast!

After trying endless numbers of podcasting tools, I've finally found a combination that works wonders. I record using, edit in Descript, and publish using Anchor and YouTube. Each is exceptionally well suited to the job at hand.

Riverside is similar to Zoom with features specifically helpful for recording. The application degrades the streaming quality as needed to preserve the full quality of the recording and I can export separate video and audio for each participant. It's easy to use and works directly from the browser.

Recorded episodes are exported to Descript. I'm very much a beginner when it comes to audio and video editing. Yet, with Descript, I'm able to autogenerate a transcript, edit the recording by editing the transcript, clean up audio, combine clips, and more.

As I improve, I regularly find that the tool is even better suited to supporting me than I had previously realized. The only drawback is its steep learning curve, although that may be more a comment on the user than the tool.

Once edited, all content is backed up to Dropbox.

For Funder & Founders episodes, I share all content with guests prior to publication. We often discuss topics that can be sensitive for a startup, especially for those operating in heavily regulated industries. I want to share their stories - warts and all - not trip them up. Giving my guests the opportunity to review prior to publication helps them stay out of trouble.

Once episodes are finalized, I use Anchor to publish to all podcasting platforms and YouTube's Creator Studio to publish to YouTube. Both are straightforward and work seamlessly.

From there it's the same stack and process as the letters. I author the episode announcement and writeup in Evernote, clean up in Grammarly, publish in Substack, and promote directly on LinkedIn and on Twitter using Hypefury.

Lesson #6: find the tools that work well for you. Invest the time and money to get the best out of them - the returns can be enormous. A hammer won't make you a carpenter, but you won't make it very far as a carpenter without one.

All in all, it's another five tools. Each Funders & Founders episode is a twenty-four-step process. Fat Tailed Thoughts, with no guests or transcripts, is a bit shorter at thirteen steps.

The Next Year of Fintech & Finance

My core goals remain the same - to share with you weekly and spark conversations.

I'm starting to get glimpses of what this might become. The subscriber base grew 10x without a dedicated effort to scale it. I've fielded inquiries from subscribers offering to sponsor and syndicate content. Startups have asked if they can come on the podcast.

It's exciting! I'd like to see where I can take it, scale it, and possibly monetize it. Before I share my thinking of what that might look like, it's important that you know what I won't do.

What I won't do

I won't charge for access.
We have a wonderful community of readers and listeners. I want to invite more in, the more the merrier. A subscription fee of any sort is counter to that goal.

I won't compromise on quality or depth.
If forced to choose, I'd rather produce less content that's higher quality and deeper. Higher volume content has its place - I consume lots of it as I search for topics. But that's not what I enjoy producing. I like going deep. The content I produce will reflect that.

I won't compromise on integrity.
Any consideration for monetizing Fintech & Finance comes with conflicts. I want to be comfortable appearing alongside every sponsor and guest on the front page of the Wall Street Journal. If something is sponsored, it'll be explicit. There will be nothing hidden.

What I will do is try to grow Fintech & Finance. My goals are directional at this point, not yet a definite set with measured outcomes. I'll grow them into that in time.

What I will do

Generate more public conversations.
I've so enjoyed the conversations that have been sparked by the letters and podcast. I want to have more of those in public forums - on Twitter, LinkedIn, and elsewhere. My dive into TikTok is a baby step. I have a lot to learn about how to engage on social media and bridge communities between the content and public forums.

Grow the subscriber base.
I'd like to welcome more people into the community, readers and listeners alike. Many of you have very kindly shared both with your friends and colleagues, as have the guests on Funders & Founders. I'm exploring other organic ways to get the word out including co-writing letters and hosting guests with Steven on Fat Tailed Thoughts to share their expertise.

Improve podcast production quality.
I currently do the post-production myself. It's time intensive and the quality is less than it could be. It's been a great learning experience, but I'll be able to produce higher quality output in less time with help from someone who is far more skilled.

Improve as a podcast host.
Funders & Founders is my first time as a host. I have a lot to learn. I re-listen to every episode and can see my improvement, but I'm not yet satisfied. Colossus’s Patrick O'Shaughnessy and Eric Golden, and my Fat Tailed Thoughts co-host Steven Dickens, have set phenomenal examples and I continue to study how they host as I listen.

Fintech & Finance started out to be fun and it very much still is. Monetizing is not just money, it's managing relationships with sponsors to ensure that you deliver what you promised and can evidence it as such. That can be fun but it can also become a burden. Between that concern and the aforementioned conflicts, I'm hesitant. If/when I do monetize, my initial goal will be to cover the costs of bringing onboard someone part-time to improve podcast quality.

An ask to you

I'd greatly appreciate your thoughts on the next year of Fintech & Finance. Key questions where I'd value your expertise and feedback:

  • What topics am I not covering that you'd like me to explore?

  • What topics am I covering too much?

  • Who is on your wish list for Funders & Founders guests?

  • Where do you have public forum conversations?

  • What strategies have worked for you to grow a reader and/or listener base?

  • Who should I be talking to about monetizing something like Fintech & Finance?

Thank you in advance for your thoughts 🙏. Your feedback is what's gotten Fintech & Finance to this point and I'm confident it'll set the next year up for even further success.

It's been an awesome year. I'm excited for what the next one brings!

Cocktail Talk

  • Local newspaper may have at last found their home - on Substack. In the letter on Netflix, I chronicled the hollowing out of local newspapers to advertising and lamented their failure. The Charlotte Ledger has cracked the code. $226,000 in revenue last year with just two full-time employees and 12,8000 subscribers. It's succeeded by getting smaller - four separate letters, some as narrow as just covering the new local professional soccer team. It's a breath of fresh air in an otherwise troubled industry. (Simon Owens Media)

  • Rivers don't always keep the same course. When they change, it can be sudden and catastrophic. Despite the potential destruction, our understanding of why and how rivers change course is poor. A new global database of 113 such events since 1973 from 100 rivers is giving us new insights. Make sure to check out the first video - it shows the Mississippi changing course over the last 7000 years. (The Conversation)

  • Shopping carts are among those inventions now so pedestrian that we hardly give them a second thought. But just 50 years ago they were still a novelty that elicited strong opinions on masculinity and status. (CNN)

  • Insect populations are crashing - Denmark alone has lost 97% of its insect biomass since the 1990s. The situation is so stark in China that they've begun hand-pollinating crops. This isn't just about wildlife preservation - it's food security. (Civil Eats)

Your Weekly Cocktail

Years of testing later (someone had to do it) and I've perfected my version of the Manhattan. It's nothing fancy, but it's how I like it. It's rare the week when I don't make at least one.


2.0oz High West Double Rye!
1.0oz Dolin Sweet Vermouth
2 dashes Angostura Bitters
1 Luxardo Cherry

Wait until the end of the day. Pour everything into a mixing glass. Add two large two-inch ice cubes. Stir precisely 50 times. Strain into a rocks glass because you still haven't learned how to drink out of a cocktail glass. Spoon in the Luxardo cherry with just a bit of syrup. Find yourself a comfy leather chair, a book, and enjoy.


There are things in life I enjoy because they take time. It's as much about how you get there as it is about where you're going. Stringing tennis rackets was one of those while growing up, the mindless monotony of weaving cross-strings amongst the mains in an unfinished basement as Californication looped in the background. Making a Manhattan is the most familiar today. It's as much that it marks the end of the day, unwinding into the evening, as it ever is about the drink itself.

There are more elegant, more balanced Manhattans. Mine is full force. There are better ryes, better vermouths - and certainly better Manhattans - but few pack the punch that this does. Dolin can't begin to tame the deliberately overdone spice turned up to eleven with often heavy-handed dashes of bitters. It's not a drink for sophisticated palettes. It's a drink that reminds you it's there with every sip, that forces you to take it a bit more slowly, a bit more deliberately than its more considered brethren. But that's exactly the point - this marks the end of the day, a shift from work to play. If I could only have one more drink, this would be it. If I were stuck with just one for the rest of my life, this too would be it.

It's not much, but it's my Manhattan.


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