Braden Dennis — How One Frustrated Investor Democratized Wall Street's Data
"I don't want to build a scoring system that tells you if a stock is good or bad" — the CEO of Fiscal AI on why owning the data content is the moat, and on the two numbers that let him ignore every headline about the card networks.
One-line take: This is a practitioner-operator interview, not a market call — Dennis states only a handful of real positions and one detailed case study, and the rest is research method and industry structure. The positions: he has been a long-term shareholder of V and MA ("probably two of the most brilliant businesses ever created"), holding "for decades potentially", and he dismisses the interchange-cap headlines as noise because the only two things he tracks — combined total transaction volume at the $27–30tn scale and total cards in force across Visa, Mastercard and AXP — are unaffected. The case study is UBER: he was publicly wrong for about two years ("a ZIRP phenomenon, venture-backed subsidized, terrible unit economics"), then the KPI data changed his mind — take rates doubled while total trips tripled — and he became a shareholder while "the consensus on the street was that Uber's never going to make a dollar." He is researching ABNB ("starting to look pretty interesting") but the punchline of his own cross-comparison is that BKNG, not Airbnb, has grown gross bookings fastest off the COVID lows — "that is not a thesis that I would have come in with." Two stated negatives: he screens metals and mining out because junior mining is "boom bust… more like a lottery ticket" (a sector view, not a security view), and he calls technical analysis "astrology more than investing". On the business: three chapters — Yahoo Finance on steroids, the viral LLM chat product (60,000 signups in 48 hours), and now owning the data layer, which he says is the only reason a challenger can take share, because a buy-sider's compliance team needs to click a cell through to the filing. Two days of data latency compressed to two minutes; 96TB stored, 2.4m SEC filings; ~150,000 users, ~50 employees, a $46bn/yr industry. Timestamps link into the video.
1. Stocks & names mentioned
| Ticker | Name | Research | View | What he said | At |
| V | Visa Inc. | QT · SA · STK · FA | Positive | A disclosed long-term holding and his own worked example of blocking out headline noise. "I've been a long-term shareholder of Visa and Mastercard. I've owned them both for a long time. I think they're probably two of the most brilliant businesses ever created." Against recent negative news about a potential interchange cap he sets two metrics: combined total transaction volume "at the 27 to I think combined 30 trillion scale across those two companies", and total cards in force. "If anything is threatening those two metrics for these three companies, then I'll pay attention… But until then, I'm just holding them for decades potentially." He adds that he thinks the price paid is reasonable and that the unit economics are what make it work. Visa is also the walk-through name on the platform demo — $16.7tn of transaction volume in the segments view, and a September-25 quarter net revenue that came in at exactly $40,000,000,000. | 48:36 |
| MA | Mastercard Incorporated | QT · SA · STK · FA | Positive | Held on exactly the same terms as Visa and always named in the same breath — "I've owned them both for a long time… probably two of the most brilliant businesses ever created," held "for decades potentially." The monitoring is one shared dashboard: total transaction volume and total cards in force stacked across Visa, Mastercard and American Express. Anything short of a structural break in those two numbers he treats as noise, including the interchange-cap headlines that he says would mostly hurt the banks administering the cards and the end consumers. | 48:36 |
| UBER | Uber Technologies | QT · SA · STK · FA | Positive | A shareholder, and the interview's central case study in changing your mind on data rather than narrative. "I said to myself Uber is a ZIRP phenomenon, venture-backed subsidized, terrible unit economics business. I said that to myself when it was public for about two years" — then the KPIs turned him: "take rates doubled while the trips tripled. That's a rare kind of KPI you see from a business, to be able to double their pricing power and usage triple… Oh wow, this company's actually about to get really profitable." He bought while "the consensus on the street was that Uber's never going to make a dollar." He also names his exit trigger on it: an autonomous-vehicle hit would show up in the same trips metric — "or even worse, they stop reporting or stop disclosing the number… I would be very much so looking for the exit before other people are." | 39:50 |
| AXP | American Express Company | QT · SA · STK · FA | Neutral | Tracked, not stated as a holding — the distinction matters. Amex is the third name in his payments dashboard: "I have a dashboard where it's payments, which stacks up total transaction volume for Visa, AXP and Mastercard… as well as total cards in force across those three companies." He says "these three companies" when describing what he monitors but "them both" when describing what he owns, and he never claims a position in Amex. | 49:30 |
| ABNB | Airbnb, Inc. | QT · SA · STK · FA | Neutral | Actively under research, no position stated, and the name his own data pushed back on. "Airbnb has been a company that's starting to look pretty interesting for me. So, I've been doing some more research" — the research being a saved cross-company chart of gross bookings across Expedia, Booking Holdings and Airbnb. "This gives me an idea of like, oh, I think Airbnb is growing the fastest, but what I actually realized is Booking's growing the fastest off the COVID lows. That is not a thesis that I would have come in with." He guesses most people off the street would say Airbnb too: "the data tells you otherwise." | 1:05:37 |
| BKNG | Booking Holdings Inc. | QT · SA · STK · FA | Neutral | The surprise winner of his own comparison, stated as a fact about the numbers rather than as a stance: "what I actually realized is Booking's growing the fastest off the COVID lows" on gross bookings, against Airbnb and Expedia. He gives no view on the stock and no position; the point he draws is methodological — "this is a really nice place to understand narratives and real factual numerical data." | 1:06:07 |
| EXPE | Expedia Group, Inc. | QT · SA · STK · FA | Neutral | The third leg of the saved "travel aggregators" chart, named only as a comparator: "I like to keep track of gross bookings across Expedia, Booking Holdings, and Airbnb and see which ones have grown the fastest… off which base, off which take rate? And they disclose all of these numbers for investors." No view on the stock. | 1:05:37 |
| LUV | Southwest Airlines Co. | QT · SA · STK · FA | Neutral | UI demonstration only — no view expressed. Pulled up live to show what a COVID collapse and recovery looks like as a chart rather than a table ("I just pulled up Southwest the airline. It's interesting visually"), and again as the example for querying a single earnings transcript or slide deck side-by-side with a custom AI prompt. | 55:59 |
| AMZN | Amazon.com, Inc. | QT · SA · STK · FA | Neutral | Illustration only — no view expressed. Used twice as a stand-in for "a company that just reported": the incumbents' manual data factory when "the Amazon 10-K comes in", and the latency claim — "when Amazon does report their numbers at the close today… you're going to get it at 4:02 p.m., not 4:02 PM in three days from now." | 30:23 |
| TSM | Taiwan Semiconductor Manufacturing Co. | QT · SA · STK · FA | Neutral | UI demonstration only — no view expressed. The name that happened to be sitting in the dashboard's notifications panel during the demo: "Taiwan Semiconductor just posted this event. Okay. Let's look at what that is. Oh, it's their Q4." | 1:09:17 |
| FDS | FactSet Research Systems Inc. | QT · SA · STK · FA | Neutral | Named as the incumbent he is trying to displace, not as a stock. Chapter three of his company is "can I build AI native FactSet better, faster, cheaper across the board"; the "Bloomberg killer products… have not actually been able to take material market share away or compete with the FactSets of the world" because they license rather than own the data. His description of their production process — Joe takes the income statement, Sally the cash flow, "and by the way, we have 200 other companies that just reported" — is the process he says AI removes. No investment view is expressed either way. | 22:17 |
| Bloomberg | Bloomberg L.P. (private) | — | Neutral | Private, and named only as the industry's benchmark incumbent — the host introduces Fiscal AI as "competing directly with giants like Bloomberg and FactSet", and Dennis coins the category for everyone who has tried: "what I'll call air quotes right now… Bloomberg killer products have not actually been able to take material market share away." Financial data as a whole he sizes at "a $46 billion a year business", with five big incumbents acting as "the arms dealer in this industry." | 22:17 |
| Fiscal AI | Fiscal AI (private; venture-backed) — his own company | — | Neutral | His own private, venture-backed company — listed for the record, not as an investable stance. "At its core, we are a financial data and financial information business," consumed three ways: a terminal, an Excel add-in, and a data-feed API that other fintechs license. ~150,000 users and ~50 employees, every full-time employee holding equity. Three chapters: Yahoo Finance on steroids; the viral ChatGPT-era chat product (60,000 signups in 48 hours) which he then cancelled contracts on; and now owning the data layer — "yes, it's data in the public domain but we've put together the data set and own all that IP." 96TB stored, 2.4m SEC filings, two-day industry latency compressed to two minutes. | 44:22 |
"View" is Braden Dennis's stance in this interview (Positive / Neutral / Negative), not a price rating. He is a practitioner-operator, not a strategist: only V, MA and UBER are stated holdings. AXP appears in his monitoring dashboard but is deliberately not recorded as a position — he says "them both" of Visa and Mastercard and "these three companies" of what he tracks. LUV, AMZN and TSM are UI demonstrations only and carry no view; FDS and Bloomberg are competitors, not picks. His one genuine negative is a sector, not a security: he screens metals and mining out entirely — "I don't like junior mining. I think it's just so boom bust, hard to make money. It kind of feels more like a lottery ticket unless you're in the industry" — so it gets no row. He is equally blunt that his platform is "completely useless if you're looking to draw some technical analysis on a chart", which he calls "astrology more than investing". Research: QT Qualtrim · SA Seeking Alpha · STK Stock Analysis.
2. Talking points
0:00 Cold open — "you own the data"
- The first five minutes are a preview clipped from the body of the interview (it repeats verbatim at 21:52–27:24): the moat is owning the data content rather than licensing it, and the reason it is possible now is an AI reasoning layer replacing a manual data factory.
- The host's summary of what changed: "the world of investing is changing at the fastest pace that I've ever seen. Not the core principles, but how we get there and how thorough we can be about research."
7:56 The host's frame — Ben Graham's 1955 Senate hearing
- Baranowski opens on Graham's testimony about "a market mystery that's resolved eventually by value recognition", and casts better tools as the mechanism: "the more people are capable, knowledgeable, and have the right tools, I think the markets can work just a lot better."
- He returns to it at the close — "I think Ben Graham would have been really impressed with what's available to us these days compared to what was available when he was playing this game."
9:02 A math kid outside Toronto, and engineering for optionality
- Middle-class upbringing near Toronto; 30 years old now; "I knew from a very young age that I was a math kid" and carried it into an engineering degree "knowing that that would serve probably a career with the most optionality."
- On why numbers grabbed him and essays didn't: "the feedback loop on something that is numerically correct versus abstract opinion has completely different incentives on how you want to study or better understand the rules of the game."
10:29 The mission — capitalism is not zero-sum, so own assets
- The formative observation, from a large extended family: "the people in my family… that were doing the best were not the ones that made the most money" — the ones investing and acquiring assets were.
- His stated mission beyond the product: "you can benefit from this system much much better if you own assets… you feel like the system's cheating you if you don't own assets."
- "Capitalism is not a zero-sum game. It's not because I made money and because I invested that means I inherently stole it or took it from someone else."
13:02 The host's formative book — One Up on Wall Street
- Baranowski's first investing book was Peter Lynch's One Up on Wall Street, and the line that stuck was ownership: "I can become an owner of a business, a couple of shares with very little money, and I'll be on the same boat as the people that founded this business."
- His answer to the "is now a good time?" question he gets in his Talking Billions office hours: ownership of assets "is a lifelong pursuit."
14:27 The leap — build it on nights and weekends first
- "That's all I could really think about was not if, but when" — but he had already built enough on evenings and weekends "where I wasn't having to take a complete leap into the unknown."
- The advantage he thinks people misprice: "there's just not that many people willing to do the work on some of this stuff… if you are, you're already kind of filtered out."
15:57 Persistence math — episode 21, and Mr. Beast's hundred videos
- He has been podcasting about stocks for roughly ten years. The stat he keeps: "back in 2019 it was 95% of podcasts did not hit episode 21. So that means you're in the top 5% if you just get to episode 21."
- The Mr. Beast version: "I will give you free consulting and help you make videos after you've made a hundred" — and nobody comes back, because by then they have learned it themselves.
18:12 Chapter one — Yahoo Finance on steroids
- Three distinct eras; they are in chapter three now. Chapter one's brief: "can I build Yahoo Finance on steroids? A non-ADR-riddled experience, good data, not being limited, not feeling so retail, but still so accessible."
19:05 Chapter two — the viral AI chat product, 60,000 signups in 48 hours
- They hooked the ChatGPT LLM API into a finance product and "it went viral overnight… we got like 60,000 people signed up in the first 48 hours," with venture investors calling.
- Not just the first application of the technology in finance but "one of the first applications of that technology period, in any vertical."
- What they concluded anyway: retrieval, manipulation and summarisation "was probably going to commoditize to zero as the LLMs became better and bigger and cheaper and faster."
20:09 The arms dealers of a $46bn industry
- Rebuilding "the airplane engine as it was flying" — the entire data infrastructure — while the chat product ran.
- The realisation: "these five big multi-billion dollar incumbents are the arms dealer in this industry… taking most of the unit economics of the entire industry" — and Fiscal was a customer of their data feed too. "Financial data is a $46 billion a year business."
21:15 Killing a working product to go after the data layer
- Contracts about to be signed that "were going to take the business to multi-millions of ARR from say 1 million" were cancelled — "we said no to all of it."
- The trade: "there's a much bigger prize of solving the data layer here." Chapter three is "can I build AI native FactSet better, faster, cheaper across the board. And the answer is proving out to be yes."
22:17 Why owning the content is the moat — the buy-sider's compliance test
- Why every "Bloomberg killer" has failed to take material share: "they are licensing that data and don't own the content."
- The objection that killed deals before: "I love the UI. I love the UX. This is way better, faster, cheaper than FactSet. But you don't have the ability to audit the number where it came from. My compliance team says I need this to subscribe… I'm a buy-sider. I need to put my neck out on this. I need to be able to click through to the filing."
- "Before we owned our own data content, there's no technology that could solve that problem. There's nothing we could code up to solve that problem."
25:42 Why now — a reasoning layer replaces the data factory
- The incumbent process, described from the inside: "Joe, you're taking the income statement this company just reported. Sally's taking the cash flow. I got the balance sheet… and by the way, we have 200 other companies that just reported" — which "leads to slowness, inaccuracies, shortcuts being made, especially with some of the smaller companies."
- What is new: "with AI I have a reasoning layer on what we're doing when we're extracting the data and properly doing the standardizations into the different industry templates."
- Why nobody funded a challenger before: "I'm going to disrupt one of these companies. I just need a billion dollars so I can hire 10,000 people. That's not getting funded, and that's why the data moats were so strong."
28:11 The scale — 96 terabytes, 2.4 million SEC filings
- The host's numbers, unchallenged: 96TB of data stored and 2.4m SEC filings. "A human being cannot process it. Just cannot."
29:49 Two days to two minutes — and the three ways data is consumed
- "Those three key areas people consume it are on a terminal, in an Excel add-in type product, or on a data feed API. And we play in those areas." Other fintechs — "say you're the Robinhood of country X, Y and Z" — license the feed.
- The incumbent wait is "on average two days, sometimes longer for small caps" for cleaning, standardising, consolidating and QA. "What takes them two days, we do in two minutes."
- "Why should I wait two days for public information that the market has already gotten?… How you actually bake the cookie matters in terms of how it tastes."
35:34 No scoring, no verdicts — the feature customers ask for and don't get
- "We don't provide any sort of scoring. We've steered clear of all of those features that our customers have asked us for, by the way. It's so important to listen to users. It's also so important to know when to ignore their recommendations."
- "I don't want to build a scoring system that tells you if a stock is good or bad or valued or undervalued. I'm just here to present you all the information."
- Where he thinks AI does not belong: "letting GPT manage your portfolios hasn't really been linked to good returns and active trading doesn't necessarily lead to great returns." The host's phrase for it: the technology "doesn't allow you to outsource judgment."
38:25 Company-specific KPIs — the Substack-screenshot problem
- The origin of the feature that became his differentiator: reading thoughtful research on Substack and noticing the author had pulled the real business metrics into Excel by hand, "because no one had done it for them."
- "I thought it was just crazy that the core fundamentals of the company were not accurately being tracked anywhere for people to get up to speed on something."
39:50 The Uber reversal — take rates doubled while trips tripled
- He was wrong out loud for two years: "Uber is a ZIRP phenomenon, venture-backed subsidized, terrible unit economics business."
- What changed it was two KPIs moving the wrong way for that thesis: "take rates doubled while the trips tripled. That's a rare kind of KPI you see from a business, to be able to double their pricing power and usage triple."
- He bought before the consensus turned — "back then the consensus on the street was that Uber's never going to make a dollar. And that's not that long ago." His point about accessibility: "you don't have to be an investment analyst to really understand those core business metrics."
41:11 The exit trigger — when they stop disclosing the number
- The KPI is the holding thesis and the sell discipline: an autonomous-vehicle threat "I'm going to see it there. That's where you're really going to see things get dicey."
- "Or even worse, they stop reporting or stop disclosing the number. We flag right on the platform that they've discontinued that number. So if that were to happen, I would be very much so looking for the exit before other people are."
43:17 Fundamentals only — technical analysis as "astrology"
- The product is "completely useless if you're looking to draw some technical analysis on a chart and make some sort of prediction on price movement… a lot of that stuff that I call astrology more than investing, to be honest. We don't provide any of that."
- His observation about the two user cohorts: a professional running billions and an individual running their own money are "looking at the same things… the use case is identical."
47:21 The eight-things template — simplify in order to hold
- Running the business forced him to turn over more stones, but it also "simplified my process a lot… there's just a few key things that I really want to track."
- The pattern he built a feature for, from users who work the same way: "these are the eight things I care for every company, I want to create that as a template as a starting point for each name."
- Why it matters: "you can drown in — I love that I have the ability to pull all the data, but… I also want to just pull up a view and be narrowly focused on what I think matters."
48:36 Visa and Mastercard — two metrics that outrank every headline
- The disclosed position: "I've been a long-term shareholder of Visa and Mastercard… probably two of the most brilliant businesses ever created."
- The noise he is deliberately ignoring: recent negative news about a potential cap, which would "massively hurt the banks that administer those cards and… the end consumers."
- The dashboard that decides whether he cares: combined total transaction volume "at the 27 to I think combined 30 trillion scale" plus total cards in force across Visa, AXP and Mastercard. "If anything is threatening those two metrics for these three companies, then I'll pay attention."
50:22 Decades of holding, checked quarterly
- "Until then, I'm just holding them for, you know, decades potentially… finding the simplicity in the data as well too is really what makes you a long-term patient investor."
- The cadence, in his words: "we're all tracking the score every quarter… the right amount of frequency to stay on top of the story every 3 months without being spoonfed it every single day so that you have decision paralysis."
- The host's version of why this matters: "there's no shortage of great ideas… There's a shortage of the ability to hold them long enough. And it's not just patience, it's the conviction."
52:48 The walk-through — financials, then segments and KPIs
- Overview tab: top-level ratios, business description, trailing-month news, a bulls-bears summary. Financials tab is "the guts": three statements, ratios, KPIs, adjusted and custom metrics, forward estimates, 20 years of history, switchable to quarterly.
- Click any number and "boom, it builds you the exact data visualization" — overlay revenue with diluted EPS, or a KPI against revenue on a separate axis.
- Segments and KPIs: revenue by geography and by line item, plus the reported operating metrics — "16.7 trillion dollars of transaction volume just really gives you a sense of scale" for Visa.
57:08 Filings and IR — query the document, not the whole model
- The "investor relations" tab holds the unstructured content — PDFs, reports, earnings-call transcripts — in one viewer, with a side panel for one-shot or custom AI summaries.
- The distinction he draws against downloading a transcript into a general chatbot: "I don't want to reach in the mind of the entire LLM. I want to reach into the mind of the LLM's extraction of this specific document."
- The host adds his own trick: listening to the earnings audio, because "the voice itself tells a story."
58:49 Every number traced back to the filing — and the $40,000,000,000 that looked fake
- "Every single number we trace back in the cell to where it came from in the filing. And this isn't just for US companies. We have it all for Canada, UK, and Europe too."
- Why it is the trust mechanism, not a feature: "there's no such thing as a perfect data set in the world, but we're asymptotically have kind of the most institutional one now. And trust is built over me showing you instead of me telling you."
- The demo: Visa's September-25 quarter net revenue "almost looks fake. It is 40 billion. Not 40 billion 362. It is 40,000,000,000" — and the 10-Q confirms it. The host's framing: a junior analyst brings you a number that looks off, and now you can check it "without a trip to the other office."
1:02:30 Screen to exclude — GARP by style, and no junior mining
- "I love stock screeners. I always have… Not because, oh, here's a list of things that I should invest in, but here's a list of things that I know I might be interested in."
- The inversion: "it's really helpful to filter not what's in the screen, but filter out what's maybe not a good use of my time."
- His own style, stated: "somewhere in that growth at a reasonable price type area" — no steady topline growth history and, special situations and spinouts aside, "I'm very very unlikely… going to be a long-term shareholder."
- The one sector he names and removes: "I don't like junior mining. I think it's just so boom bust, hard to make money. It kind of feels more like a lottery ticket unless you're in the industry. I want to exclude those industries. So I can go in here and exclude metals and mining and now rerun the screener."
1:04:59 Cross-comparison — the travel aggregators, and the answer he didn't expect
- Saved charts he keeps: trading platforms, the payments one (transaction volumes across Visa, Mastercard, American Express), and "travel aggregators" — gross bookings across Expedia, Booking Holdings and Airbnb, "off which base, off which take rate."
- Airbnb is "starting to look pretty interesting for me… I've been doing some more research" — but the chart contradicted him: "what I actually realized is Booking's growing the fastest off the COVID lows. That is not a thesis that I would have come in with."
- The general use: check a company's own account of its industry against its peers' disclosed numbers. The host's version — if one company says it can't push pricing while three peers are growing volumes and margins, "maybe the company you're paying attention to is facing some other challenges."
1:08:16 Dashboard, watchlists, notifications — and what's coming
- The dashboard holds watchlists with user-chosen columns (he sorts by forward EV/EBIT), an ownership breakdown that aggregates your positions "if it was a specific business", and a notifications panel — Taiwan Semiconductor's Q4 posting is the live example.
- The roadmap is personalisation plus geography: today "there's this non-symmetrical experience if you're looking at a US company versus some micro cap in Taiwan", and the engineering work is to make it uniform. "We don't want to just be focusing only on the US, Canada, UK."
1:11:03 Success — 50 employees, all of them shareholders
- On the moving goalpost: "I'm very rarely looking out the rearview mirror and always forward… I wish I was better at this honestly, but it's just not who I am."
- The ambition is not modest: "I also want to build a really sustainable heavy business that is the next really big powerful business inside of financial data."
- "Every single full-time employee has some equity in the business too… what success really looks like for me is that all of those people get really good outcomes and not just me." The host closes the loop back to the asset-ownership mission he opened with.
1:14:45 The free plan now gives 10 years of history
- "We just recently made the free plan — so throw away the trials… we now give everyone 10 years of data. It used to be just four or five."
- The claim attached to it: "of all the ones that exist there, no one is offering 10 years of historicals. There is not one of them doing it."
3. In plain English
V — Visa Inc. Positive
Visa does not lend money and does not issue cards. It runs the network that moves a payment from your bank to a shop's bank, and takes a tiny slice of every transaction that crosses it. That means its economics scale with two simple things: how much money flows across the network, and how many cards exist that can put money onto it.
Dennis has owned it for years and expects to keep owning it "for decades potentially" — he calls Visa and Mastercard "probably two of the most brilliant businesses ever created". What makes his version of the thesis useful is that he has written down, in advance, the only evidence that would change his mind: combined total transaction volume across the networks (he tracks it at the $27–30 trillion scale) and total cards in force. Everything else is noise to him.
That includes the recent headlines about a possible cap on card interchange — the fee merchants pay on each swipe, which is shared with the bank that issued the card. He does not argue the news is wrong; he argues it does not touch his two numbers, and that the pain would mostly land on the banks administering the cards and on consumers. He also says the price he is paying looks reasonable. So the position is not "ignore regulation" — it is "here is the specific measurement that would tell me the regulation actually mattered, and it hasn't moved."
MA — Mastercard Incorporated Positive
Mastercard is the same kind of business as Visa — a toll road for payments rather than a lender — and Dennis treats the pair as one position. He has held both "for a long time", names them together every time, and monitors them on a single dashboard that stacks total transaction volume and total cards in force across Visa, Mastercard and American Express.
The interesting part is the discipline rather than the pick. Rather than reacting to each new headline about fee regulation, he reduced two enormous businesses to two operating numbers, decided in advance what a genuine threat would look like in those numbers, and now only re-engages when something "structurally" moves them. He describes checking the score once a quarter as the right frequency — often enough to stay on the story, rare enough to avoid decision paralysis.
Note what he does not say: he gives no target price, no valuation call beyond "a reasonable price, which I think they are", and explicitly disclaims investment advice. The thesis is unit economics plus a monitoring rule, held over decades.
UBER — Uber Technologies Positive
This is the interview's best story, and it is a story about being wrong. For roughly two years after Uber went public, Dennis dismissed it out loud as "a ZIRP phenomenon" — a business that only looked viable because interest rates were near zero and venture investors were subsidising cheap rides — with "terrible unit economics".
What changed his mind was two operating numbers rather than any narrative. Total trips on the platform were tripling. At the same time the take rate — the share of each fare Uber keeps rather than passing to the driver — doubled. Those two usually fight each other: raise your cut and customers use you less. Getting both at once is the rare signal that a company has genuine pricing power and genuine demand, and it told him profitability was arriving. "Oh wow, this company's actually about to get really profitable." He became a shareholder while "the consensus on the street was that Uber's never going to make a dollar."
He is equally explicit about how he would leave. The same trips metric is where a robotaxi threat would show up first. And there is a second, subtler trigger: if Uber simply stopped publishing the number, he treats that as the sell signal — "I would be very much so looking for the exit before other people are." A company that quietly discontinues its own headline KPI is usually not doing so because it flatters them.
ABNB — Airbnb, Inc. Neutral
Airbnb is the one name he says he is actively working on — "starting to look pretty interesting for me. So, I've been doing some more research" — but he states no position and reaches no conclusion on the record, so this is a research-in-progress mention rather than a recommendation.
The way he researches it is the transferable part. Instead of studying Airbnb alone, he built a chart comparing gross bookings — the total value of travel booked through a platform, before the platform's own cut — across Airbnb, Booking Holdings and Expedia, and asked which is growing fastest, from what starting base, and at what take rate. All three companies disclose those numbers themselves.
The result went against him: Booking, not Airbnb, has grown gross bookings fastest off the COVID lows. "That is not a thesis that I would have come in with." He notes most people asked cold would guess Airbnb too. The lesson he draws is not about Airbnb's quality — it is that a widely-held industry narrative is cheap to test against the companies' own disclosures, and worth testing before you own anything.
BKNG — Booking Holdings Inc. Neutral
Booking Holdings owns Booking.com and the other large online travel agencies, and it earns a commission on travel booked through its sites. Dennis holds no stated position and offers no view on the shares — it appears here purely as the answer his own data gave him.
Comparing gross bookings across the three big travel aggregators, Booking is the fastest grower off the COVID lows, ahead of Airbnb, which was the intuitive answer and the wrong one. "The data tells you otherwise."
Treat it as a lead rather than a call: a company outgrowing the peer everyone assumes is the growth story, discovered by putting three disclosed metrics on one chart. That is exactly the kind of gap between narrative and numbers he says the cross-comparison view exists to surface — and it is the point at which real research on the name would start, not end.
Compiled from the public YouTube video for personal study. Stances are Braden Dennis's own as stated on Talking Billions on 2026-01-28; he discloses long-standing positions in Visa, Mastercard and Uber and states repeatedly that none of it is investment advice. He is the founder and CEO of Fiscal AI, the platform demonstrated throughout, and the show discloses Fiscal AI as a sponsor. Not investment advice.