Speaker · Updated
Shawn O'Malley: latest market views
The Investor's Podcast Network
Summary
Shawn O'Malley is a host at The Investor's Podcast Network, where he hosts Millennial Investing and The Intrinsic Value Podcast and co-hosts The Investor's Podcast, breaking down and valuing businesses from a value-investing perspective.
Chorus has 53 views from Shawn O'Malley across 3 episodes on We Study Billionaires since October 22, 2026. Their latest calls: bullish on Airbnb and GE Aerospace; bearish on Amazon.com, Shopify and TransDigm Group.
Where they stand
Their latest bullish or bearish call on each company.
- AirbnbBullish ·
- Amazon.comBearish ·
- ShopifyBearish ·
- GE AerospaceBullish ·
- TransDigm GroupBearish ·
What they talk about most
The latest views
Newest first. Every quote is checked against the episode's transcript.
AirbnbBullish
Airbnb has a long runway as travel grows and alternative stays take share from hotels.
Shawn points to the World Cup, which brought 150,000 new homes onto Airbnb, with hosts earning hundreds of millions and guests from 196 countries across 16 host cities. He argues that anywhere other than a traditional hotel is taking a growing share of bookings from hotels, and that he uses Airbnb for nearly all discretionary travel because of pet-friendliness, shared family space and community feel. He sees a long growth runway as the world travels more.
“So I continue to see Airbnb as having a long runway ahead of it as the world travels more and more and as alternative accommodations.”at 3:47
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
About 90% of Airbnb's traffic is direct or unpaid, unlike Booking's multibillion-dollar ad spend.
Shawn says that during COVID Airbnb shut off most performance marketing to save cash, and it still retained roughly 90% of total traffic, which comes directly or through unpaid channels. He contrasts this with Booking.com, which reportedly spends about $5 to $7 billion a year on advertising, mostly Google clicks. Because Airbnb spends a much smaller share of revenue to acquire customers, he calls this a major competitive advantage.
“they actually still had roughly 90% of their total traffic return. So they still get about 90% of current customers coming directly from their platform or through unpaid channels.”at 11:55
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Sponsored listings are low-hanging fruit that could become a big Airbnb business, though timing is slower.
Shawn argues that sponsored listings seemed like low-hanging fruit, similar to Amazon or Google sponsored results, letting hosts bid on keywords for top placement. He admits he may have been wrong to expect them sooner, since management has not discussed them recently. He still believes ads could become a big business down the road, and that the investment never depended on their timing.
“While I felt it seemed like pretty low hanging fruit to just go after sponsored listings, perhaps I was wrong in assuming that we would see them sooner than has happened in reality.”at 26:23
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Agentic shopping remains unproven, so Airbnb can raise take rate without being overly disrupted by AI.
Shawn concedes sponsored listings will weaken to some extent if AI agents are used at scale, and that Meta's Muse agent has gone viral with consumers. But he argues that running everything through an agent, especially shopping, remains unproven despite the hype. He suggests Airbnb may find a way to improve its take rate without being overly disrupted by AI, and he is comfortable with management taking its time.
“the idea of running everything through an agent, especially shopping decisions, I think really remains an unproven concept despite the hype around it.”at 29:01
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Airbnb's insurance business, growing 60% a year in 12 countries, could scale and help margins.
Shawn notes that Airbnb's insurance business is offered in only 12 countries yet grows revenue 60% year over year. He admits it is still a small revenue producer that does not move the needle much. He thinks it could be scaled up and would further help margins, which he finds promising.
“their insurance business is only offered in 12 countries, but it's growing revenue by 60% year over year. So even if that doesn't move the needle a ton, it does seem like something that could very much be scaled up”at 29:49
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Airbnb's 10% nights-and-seats growth versus Booking's 4% alternative-stay growth shows Airbnb taking share.
Booking Holdings now has about 9.1 million alternative accommodation listings, all competing with Airbnb, and Booking's latest investor deck showed 4% growth in that segment. Airbnb grew nights and seats booked 10% year over year. Shawn argues this gap means Airbnb is still taking market share from Booking, even though Booking is not dead.
“When you compare that with Airbnb's growth of 10% year over year in nights and seats booked, it does appear that Airbnb is is still taking market share from them.”at 31:03
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Verified identities, reviews and host messaging make Airbnb's trust hard for AI chatbots to replicate.
Shawn argues trust is becoming more important as AI chatbots spread. Chesky said a chatbot does not have Airbnb's 200 million verified identities or 500 million proprietary reviews, and cannot message the host, which 90% of guests do. Shawn adds that about 70% of listings are exclusive to Airbnb, and most hosts default to the platform where their guests are. Airbnb took nearly two decades to build this, which is why he is comfortable letting his family stay in strangers' homes.
“The other advantage I'd mentioned too is trust, which I think is becoming increasingly important with this growing world of AI chatbots, right?”at 32:53
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Airbnb's guest loyalty and app-booking share make its moat stronger over time, even versus pro hosts.
Shawn argues the real moat is guest loyalty, not host supply. Professional property managers can delist from Airbnb at any time, but they cannot take Airbnb's guests with them. Hosts multi-list to whichever platform fills their calendar, so guest demand is what keeps them on Airbnb. The evidence is Q2 data: 64% of nights were booked through the Airbnb app, up from 59% a year earlier. App nights grew 23% year over year against 10% growth in total nights and seats booked, so app bookings are growing about twice as fast as the business. Users who open the app to plan a trip are not comparison shopping, so pros have little reason to leave even if they list elsewhere too.
“What keeps them on Airbnb isn't the supply side, but it's the robustness of the demand. And a property manager can pull their listings off of Airbnb tomorrow, but they can't take Airbnb's guests with them.”at 38:15
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Airbnb's buy-now-pay-later feature costs some float and timing, but its net benefit will show over time.
Airbnb's 'reserve now, pay later' feature launched in mid-2025 and went international in early 2026. It has real cash-flow costs: fewer guests pay upfront, so less float is held and earns interest, which helps explain falling interest income even as rates rose. Unearned fees jumped about 60% this year, but that is seasonal. On a June-to-June basis they were flat even though bookings grew 18%. The gap reflects the feature at work: bookings count before cash arrives. Shawn sees it as a strong customer feature. If it drives more bookings because people feel comfortable booking further ahead, the trade nets out or slightly favors Airbnb.
“But it is really just a great feature from a customer perspective and so I think the net benefit will be clear over time.”at 41:51
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Airbnb's free cash flow margin shows a highly profitable, capital-light model; ROIC and ROE mislead here.
Shawn argues ROIC is meaningless for Airbnb. Customers fund the business, the hosts own the homes, and most guests pay before travel, so invested capital is near zero or negative and the ratio says little. He prefers free cash flow and operating margins. Airbnb turned 38% of its revenue into free cash flow last year with little capital needed to grow. ROE of about 35% is also distorted: buybacks have shrunk equity from about $8.2 billion at year-end to $7.8 billion by June, which lifts ROE even if the business does not improve.
“Airbnb turned 38% of its revenue into free cash flow last year, which is very, very good without needing really much capital at all to grow.”at 46:55
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Operating leverage is starting at Airbnb, with stock comp growing slower than revenue and drifting toward 11%.
Shawn says stock-based comp grew faster than revenue for three straight years, rising from about 11% of revenue in 2022. Management said the 2025 increase came from faster headcount growth. 2026 is the first year the dynamic has flipped: in the first half, revenue grew 17% while SBC grew about 15%. Management says SBC and headcount growth will slow this year. Shawn expects the SBC dollar figure to keep rising over five years, but as a share of revenue it should drift lower, maybe back toward 11%. This assumes revenue keeps growing at double-digit rates and AI helps keep headcount flatter.
“But 2026 is the first year where that dynamic has flipped. So in the first half, revenue grew 17% while stock based comp grew about 15%.”at 53:00
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Airbnb's buybacks mostly offset dilution, yet share count should keep shrinking a few percent a year.
Diluted shares fell about 5% in the last year, but much of that is buybacks mopping up stock-comp dilution. Last year Airbnb spent $3.8 billion on buybacks against $1.6 billion of total stock-based comp, so roughly 40% of the buyback budget only offset dilution before shareholders saw any net benefit. Shawn expects SBC dollars to keep rising. With $4 to $5 billion of annual free cash flow going largely to buybacks, he expects the share count to keep shrinking a few percent a year. The net per-share benefit is smaller than headline buybacks suggest.
“And with 4 to $5,000,000,000 annual free cash flow going largely to buybacks, I'd expect share count to keep shrinking by a few percent a year.”at 54:12
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Chesky's hands-on founder mode is lifting efficiency: flat headcount, doubled revenue, faster product launches.
Shawn describes Chesky going back into product details after the pandemic, against conventional management advice. Airbnb ended 2025 with about 8,200 employees, roughly the pre-pandemic level, while revenue has more than doubled. Shawn credits Chesky's hands-on approach at a key inflection point for helping shareholders. Management says it is cutting the time from idea to launch on key projects by up to 60% while launching nearly 80% more features than the prior year. Kyle agrees that founder mode suits highly efficient businesses like Airbnb.
“And then even this year, management says they're still improving efficiency by cutting the time from idea to launch on key projects by up to 60%, all while launching nearly 80% more features than the previous year.”at 58:28
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Airbnb's founder-led management and insider ownership make governance strong and aligned with shareholders.
Shawn sees Airbnb's governance as strong. Chesky and his two co-founders own over a quarter of the shares economically and hold over 80% of the voting rights. Chesky takes a $1 salary, and his large option award only pays out if the stock rises sharply, with market-cap hurdles measured on 60-day averages and delayed vesting. The board simplified the executive bonus for 2026 to revenue growth and adjusted EBITDA margins. Shawn's one quibble is that adjusted EBITDA excludes stock comp, and he would like free cash flow per share included. He concludes none of this worries him as a shareholder.
“So overall, the corporate governance is pretty good. And as a shareholder, I mean, none of this is keeping me up at night whatsoever.”at 1:06:08
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbUncertain
AI assistants could force Airbnb to pay for customers, weakening its cheap customer acquisition advantage.
Shawn sees a real risk from agentic search. Airbnb has historically acquired customers far more cheaply than competitors. If it had to pay OpenAI or Claude to send customers to it, and its supply and inventory were partly commoditized by agentic search, that would significantly weaken its position. He offsets this with evidence: about two-thirds of nights are now booked in the Airbnb app, and that share is still rising. The more bookings flow through the app, the less Airbnb relies on outside channels. He treats this as a risk the company is currently managing well.
“The AI angle probably poses a risk to Airbnb's ability to acquire customers at a much lower price than competitors, which has been an advantage for them previously.”at 1:07:51
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Airbnb's AI customer-service agent already resolves 45% of issues, improving experience and cutting costs.
Shawn argues AI has been a tailwind for Airbnb so far. The company now has AI resolving 45% of customer service issues with no human involved. He sees this as improving the customer experience and possibly saving on costs. He also wants AI to raise productivity so the company can get more from its workforce without hiring, for example by automating much of customer service. He cautions that over-eager adoption could do more harm than good, since customer service is sensitive.
“it's actually been somewhat of a tailwind for Airbnb in some ways as they now have AI resolving 45% of customer service issues without any human needing to be involved.”at 1:08:13
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbNeutral
Short-term rental rules are real but local headwinds, not a chronic threat to Airbnb's overall business.
Shawn says regulation is a real risk, but it comes as a series of local headwinds rather than a threat to the whole business. New York is the best test case. The city's bans were estimated to bring about $85 million a year to Airbnb, barely 1% of revenue at the time. Short-term listings there fell more than 80% in the first year of regulation. Yet the impact was hard to see in Airbnb's overall results. Kyle adds that EU short-term rental rules and Barcelona's planned residential ban are further local pressures, but not a gigantic headwind.
“regulation is a real risk sort of acutely because it's more of a series of local headwinds than a chronic threat to the whole business.”at 1:10:15
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbUncertain
City-level short-term rental bans are manageable for Airbnb, but national bans like Spain's would be the real risk.
Shawn argues city-level crackdowns hit little of Airbnb because it has over 9 million listings across 220+ countries, and most supply sits in beach towns, mountain cabins and smaller cities that want tourism. Dense cities like New York, Barcelona and Amsterdam are where backlash concentrates, and the NYC ban cut listings by over 80% in its first year, yet barely showed in overall results. He says the one to watch is a spread from city bans to entire countries, with Spain ordering about 65,000 listings pulled last year. The EU registration and data-sharing rules that took effect in May mostly force registration and data sharing, which he calls not terrible for Airbnb long term, but they give governments an easier tool to enforce stricter limits.
“which is not a terrible thing for Airbnb long term. ... But they also give governments a much easier tool to enforce stricter limits generally.”at 1:11:56
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBearish
Travel is cyclical; in a recession Airbnb faces falling nights and nightly rates from fixed-cost deleveraging.
Shawn says travel will always be cyclical. In a recession people take fewer trips, operate on tighter budgets, and choose cheaper options if they travel for leisure. That hits Airbnb twice: nights booked fall, and the nightly price per booking also falls as demand weakens. Airbnb has large fixed costs like engineers and marketing, so the margin expansion that came with revenue growth reverses sharply when revenue declines, which he calls deleveraging.
“So until that comes in a recession, the reality is that people are more likely to take fewer trips and they're operating on tighter budgets, of course.”at 1:12:58
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Airbnb's expansion markets are growing twice as fast as core markets, a multi-year growth lever.
Shawn cites strong growth in newer markets: Brazil up over 30% year over year with first-time bookers up 40%, Japan up high teens, and India accelerating to 60%. Airbnb reports these numbers by guest origin, so India's 60% growth reflects Indians booking more trips at home or abroad, which means new customers rather than just new listings. Wins come from small local tweaks such as interest-free installments in Brazil and Mexico and country-by-country marketing. Expansion markets grow about twice as fast as the core markets, which hold most of the business, but they are off a much smaller base, so it will take years before they move the overall growth rate. Shawn also sees Latin America up about 20% and Asia Pacific in the high teens, with North America and Europe also improving.
“the majority of Airbnb's business is so concentrated in those five core markets and the expansion markets are growing twice as fast. But of course, that's off a much smaller base, so it'll take them years to catch up before they really move the overall growth rate in a big way.”at 1:17:35
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Airbnb's hotel bookings work as a customer-acquisition funnel into home bookings.
Hotel nights are still a single-digit share of Airbnb's total nights, but they grow three times as fast as home bookings. Airbnb offers hotel stays with a price-match guarantee and credits for future bookings, which builds trust with guests who would not otherwise try Airbnb. Shawn cites that 35% of first-time hotel guests go on to buy a home stay within a year. He sees hotels as a customer-acquisition channel rather than a major growth driver in themselves.
“while the hotel growth isn't as impressive as growth in the international markets, I do think it's really functioning as a customer acquisition channel that can be funneled throughout the company.”at 1:19:18
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Airbnb's experiences business shows encouraging early signs, but it is small and long-term.
Shawn is excited about Airbnb layering experiences and services into trips, which it relaunched last year. Experience supply grew nearly 80% over the last year, and seat bookings are accelerating both year over year and quarter over quarter. Almost half of experience bookings at the end of last year were not attached to a stay, so people come to Airbnb just to book an experience, which he sees as another acquisition channel. Airbnb has not disclosed hard booking numbers, so he treats the business as still very small relative to homes. He also says Airbnb set aside $200 to $250 million last year for these new businesses and that Chesky calls it a multi-year effort rolled out one city at a time, so he expects it to be a long-term option rather than something that moves numbers in the next 12 to 18 months.
“Airbnb's ability to layer in experiences and services into trips has been and still is one of the things I'm most excited about... I think the early signs are very encouraging.”at 1:20:31
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBearish
Airbnb's margin expansion is lagging: operating margin fell to about 21%, and take rate has stayed flat near 13%.
Shawn's biggest negative surprise is that faster growth has not yet flowed through to margins, which makes sense because management is reinvesting to drive growth. Operating margin slipped from 23% in 2024 to about 21% last year, and stock-based compensation kept climbing, though the last couple of quarters were better. Take rate held around 13% rather than rising as he assumed, after Airbnb changed how it applies fees. Margin expansion is taking longer than he expected.
“the biggest negative surprise though is that the faster growth has not fully flowed through to margins yet, which makes sense because they're investing to drive that growth.”at 1:23:53
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Airbnb's revenue growth has reaccelerated, with management guiding to at least mid-teens for the year.
Revenue grew 10% last year, and then grew in the high-teens range in the first two quarters of this year. Management now expects at least mid-teens growth for the full year. Shawn says the reacceleration is the biggest positive surprise, driven by app improvements, first-time bookers, international markets and hotels. He thinks the business is in better shape than when he first pitched it.
“management now expects at least mid teens growth for the full year, which is really great.”at 1:24:01
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbBullish
Sponsored listings are Airbnb's missing revenue piece; waiting for an AI-era ad format is the right call.
Shawn says sponsored listings are still the missing piece of Airbnb's model. Chesky has called ads a fairly easy path to $1 billion of incremental high-margin revenue. Chesky has chosen to get AI right first and design an ad format around it, and Shawn thinks that is the right call even though it delays the ads business, because search is changing quickly. He would rather Airbnb build ads for how people find information in two or three years than build around traditional search. Ads are therefore a long-term option that is slower than he hoped.
“I still think the missing piece here is sponsored listings. So Chesky has called ads a pretty easy path to $1,000,000,000 in incremental high margin revenue for them.”at 1:24:48
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
AirbnbNeutral
Airbnb's share price has caught up to his roughly $150 intrinsic value estimate, so the stock looks fully valued.
Shawn's original model put intrinsic value at about $150 a share, using enterprise value to EBIT with an exit multiple in the low-to-mid twenties. The stock now trades in the mid-to-high $150s, so it has caught up to his estimate over a little over a year. Updating the model for a flat take rate and slower margin expansion, offset by faster growth, leaves his intrinsic value estimate not dramatically changed.
“And with the stock trading in the mid to high [150]s today, it caught up to that estimate and it took about, you know, a little over a year to do so.”at 1:25:48
We Study Billionaires: TIP856: Airbnb (ABNB): The Business Outgrew Its Peak, The Stock Hasn't w/ Kyle Grieve & Shawn O'Malley ·
ShopifyBullish
Shopify's merchant retention and enterprise wins show a durable moat with strong switching costs.
Shawn argues the moat rests on switching costs and an app-store network effect. Enterprise brands such as General Motors, Starbucks, L'Oreal, Estee Lauder and Coach have moved to Shopify, and switching e-commerce platforms is a major undertaking for large companies. Merchants who reach $1M in annual sales have 92% retention, rising to 97% at $10M. The cohort that started in Q1 2015 now generates 3.3 times its earlier quarterly revenue, so customers keep spending more over time. Shawn says this compounding is a key reason for the company's success. Daniel says the verticals merchants buy into create lock-in that makes Shopify more powerful than peers such as Wix.
“merchants who reached $1,000,000 in annual sales on Shopify have a 92% retention rate. And then at $10,000,000, it's 97%.”at 19:46
We Study Billionaires: TIP855: Shopify (SHOP): The Big Winner of Agentic Commerce? w/ Shawn O'Malley & Daniel Mahncke ·
ShopifyBullish
Shopify's payments push and rising take rate show its monetization flywheel is working.
Shawn argues the take rate, which the original thesis said would creep up as Shopify attached more services, is rising. Merchant solutions take rate went from about 2.2% early last year to 2.4% a year later. He says every hundredth of a percentage point is worth about $40M in revenue on more than $400B of sales. He also points to payments: Shopify Payments now processes 68% of platform GMV, up four percentage points in a year and live in 40 countries. Shop Pay has crossed $400B of lifetime volume and handles more than half of US payment volume. Daniel adds that payments volume shows strong competitive position even as payments markets get more competitive.
“the take rate went from about 2.2% early last year to 2.4% a year later.”at 21:56
We Study Billionaires: TIP855: Shopify (SHOP): The Big Winner of Agentic Commerce? w/ Shawn O'Malley & Daniel Mahncke ·
ShopifyBearish
Buying back Shopify shares at about 100x earnings looks ridiculously expensive versus reinvesting.
Shawn notes Shopify's shift to buybacks is a big change for a company that used to dilute shareholders each year, and he expects the share count to stay flat or fall. He then questions why a fast-growing company would buy its own shares at about 100x earnings rather than reinvest the cash in projects that could justify that multiple. He calls the 100x multiple ridiculous. He also recalls that in May 2025 the market was asking for more than 100x trailing operating profit, which he said embedded a best-case future. His view is that the valuation is stretched, even though the business has outperformed.
“why would you not put the cash toward reinvesting into the business rather than purchasing shares at a 100 times earnings?”at 27:31
We Study Billionaires: TIP855: Shopify (SHOP): The Big Winner of Agentic Commerce? w/ Shawn O'Malley & Daniel Mahncke ·
ShopifyBullish
Shopify's growth accelerated well beyond expectations; he underestimated 2026 revenue by about $2B.
Shawn says Shopify's growth, which he expected to slow as the company matured, instead sped up. 2025 GMV reached $378B, up 29%, and revenue reached $11.5B, up 30%, the fastest annual growth since the pandemic. Q1 revenue grew 34% and Q2 GMV was $116B, up 32%, with five straight quarters of 30%+ GMV growth. Daniel adds that North America grew 28%, Europe 34% excluding currency, and B2B 76%. Per the CFO, Shopify merchants captured nearly half of incremental US e-commerce dollars since the start of 2025. Shawn says his original model underestimated 2026 revenue by about $2B, and that the company's growth has been more sustainable than he expected.
“I actually ended up underestimating their revenues by what will probably shake out to be about $2,000,000,000.”at 31:36
We Study Billionaires: TIP855: Shopify (SHOP): The Big Winner of Agentic Commerce? w/ Shawn O'Malley & Daniel Mahncke ·
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