2025-05-07 08:00:00
Wander’s Counter-Positioning Against Airbnb & Its Self-Imposed Constraints.
Disclaimer: Never stayed in a Wander, but have been following the company for years ever since Kyle Tibbitts (a marketer I respect) joined as the CMO.
If you listen to TBPN, you must have heard Jordi Hays and John Coogan shout “find your happy place” enough times to google Wander and see what it is. Now they are raising a Series B and the size going would be hit soon on TBPN I guess.
Let’s get back to the real topic: Why I love Wander and why it is another example of counter-positioning done well.
The vacation rental market is interesting. Let’s talk Airbnb. On one hand, you have Airbnb, which has become a verb at this point. On the other hand, you have thousands of horror stories of people showing up to Airbnbs that look nothing like the pictures. Surprise cleaning fees. Hosts who don’t respond. Hard to find locations. Low touch experience at the price of a hotel.
Wander has been deliberately going after this problem. They are a counterposition to Airbnb. They have created a ‘hotelified’ alternative to Airbnb for the top 1%. They’re curating the top 1 percent of vacation homes, professionally managing each one to guarantee consistent, luxury-grade experiences. No surprises, no mismatched listings, no unreliable hosts. This is what Oyo was supposed to be in India. But couldn’t.
Wander is something Oyo could have been if it was a luxury product. “70% of Wander guests are affluent, with net worths exceeding $1M,” according to Wander’s website. “Wander’s audience is primarily composed of CEOs, founders, executives, software engineers, and individuals working predominantly in the tech sector.”
What makes them interesting is their vertical integration. Unlike Airbnb, which is just a marketplace where anyone can list their property, Wander owns and operates everything end to end. Again, like how OYO promised. They buy the properties. They renovate them. They furnish them. They handle the bookings. They manage the properties with their own team. This creates a moat that Airbnb can’t easily cross without completely changing their asset-light approach. Airbnb’s strength is also its weakness: with millions of properties, they can’t control the experience.
[Check sentiment on the Airbnb experience over the last few years on Twitter.]
There’s an obvious tradeoff. By purchasing, renovating, and operating each property itself, Wander takes on all the principal risk. This capital intensive model makes it harder to expand quickly and limits their selection compared to Airbnb.
It’s a classic case of self-imposed constraints. While Airbnb can add new hosts at internet speed with near zero cost, Wander has to buy and upgrade each property. They’re deliberately capping their total market size in exchange for higher unit economics, stronger brand loyalty, and way better guest satisfaction.
Every property has the same hotel-grade amenities: super-fast Wi-Fi, private pools or hot tubs, gyms, and 24/7 concierge service. No wonder Wander’s guest satisfaction is high (see the testimonials on their site). They’ve built something called WanderOS, which centralises all property controls into a single app. Door locks, lighting, temperature, even Tesla access. Yes, they provide a Tesla at all their vacation homes.
This appeals to travellers who want the freedom of a private home but demand the reliability, transparency, and service levels of a luxury hotel.
They’ve also got an AI-assisted concierge team that handles guest inquiries with site-specific data, automatically creating maintenance tickets or escalating to humans when needed. This tech investment lets them manage dozens of homes with fewer property managers, delivering consistent quality with higher margins.
Wander isn’t doing the 1% improvements to Airbnb’s model. They’re creating a step function change by completely rethinking the approach. They’ll never match Airbnb’s scale, but they don’t need to. They’re building a profitable, defensible niche in the high-end segment of the $1.3 trillion lodging industry.
It’s a classic example of counter-positioning. They’re building something that their bigger competitor can’t copy without undermining their own business model.
And they are also capping their growth by constraining their growth.
And I love these kinds of bets. Let the big platforms scale to infinity with lower margins while carving out the premium segment with better economics and happier customers. Not every business needs to be a winner-take-all marketplace.
(To deal with the capital constraints, they launched Atlas in 2022, which they call the world’s first vacation rental REIT. This moves property acquisition costs off their balance sheet while letting them keep operational control. Smart way to unlock investor capital without dilutive funding. You can read the details in an amazing Deep Dive done by Packy McCormick way back in 2023.)
[Post created by thought dump on ChatGPT and then verifying some of the details on Packy’s post and Wander’s own website. Then edited with Claude because Narayana knows I don’t have the patience for it.]
2025-04-28 08:00:00
I had been trying to ignore this tweet since morning. I don’t come a lot on Twitter nowadays.
But this topic is very close to my heart because I literally worked for a company that used David vs Goliath marketing when they launched in Singapore. You can google this. I’ll tell the story so that you can understand what makes business strategy work beyond vanilla oh startups grind hard, how you fight against incumbents, and how you counter position and find gaps in a market.
Let’s go back to the year 2018. Uber had left south east Asia and the leading ride-hailing company there had almost become a monopoly. They decided to devalue their reward points because, of course, they were a monopoly and could do whatever they wanted. Their margins were fat. And they would have monopoly pricing power. In that time, you had that chance to come and disrupt the market.
So, TIMING matters. WHY NOW needs to be clear. So, what do you do? You position yourself as David vs Goliath. You say, “Hey, don’t worry. We are here. We’ll support you. We’ll fight for the masses. We’ll launch a service which is just as good. But we’ll always be for the community, for the driver, for the rider.” And it was the right narrative. We were always the brand that had more love. We were not as ruthless, which you can debate whether it was right or wrong. But we were definitely the “people’s champion” kind of brand. The leadership truly cared. But over the years, we were not able to WIN (define however you want) in Southeast Asia. And we have even exited countries. That’s where the interesting part comes in about David vs Goliath, small startup vs incumbent. All of that does not matter. What matters is the long-term strategy. What is the counter-positioning strategy? Are you making some change in business model? Do you have the right to win demand? Maybe you have the right to win supply. Maybe you are creating a new category or creating a new position around that category.
Example. Zepto coming in with 10 min delivery. Winning the quick commerce narrative initially. They owned their supply while everyone else was relying on freelancers. Heavy capex and opex model vs incumbents light weight business model.
NEW POSITIONING. MORE CONTROL OVER SUPPLY. MORE UTILISATION OF SUPPLY BECAUSE OF MORE FULL TIME WORKERS THAN FREELANCERS. HIGHER OPEX AND CAPEX, AND WHILE INCUMBENTS FIGURE OUT IF THIS WOULD EVEN WORK, YOU WOULD END UP TAKING SIGNIFICANT MARKETSHARE BY THEN.
Because sure you call yourself the David vs Goliath and you launch with the same product, same margin structure, same business model, acquire similar supply, go after the same demand, and just play on the NARRATIVE, but that does not work in the long run.
NARRATIVE DOES NOT WORK LONG TERM.
So what should we have done differently? What Namma did. Namma came far later, but attacked the margin structure of Ola and Uber. There are companies in South Asia which have been doing the same playbook from far earlier. There’s this company which launched by saying, “We know that all the ride-hailing companies are expensive. But for the high price point they have highly reliable products. They are premium products. Your car arrive on time. You don’t have to wait longer. And the quality is high, but for that you pay a lot too.”
But it is also beyond the price point that most college students and economy-minded people can afford. Then what do you do? You go and say, “If you’re willing to wait 10-15 minutes, you can get your car, but cheaper. It will probably be priced at about 50-70% of the most reliable ride-hailing products. You just have to wait longer. Yes, the drivers might cancel sometimes, but you have to be okay with it.”
Especially in Singapore where supply is capped, and other strategies won’t work, you can seed your marketplace supply by cutting commission by a lot.
When you change business model or commission structure, you can do multiple things. The main players are at 25% commission because they want to run a highly reliable marketplace. So you say, “We have 5% commission because we are not a big company. We can afford to have lower revenue initially.” And it is almost like a vampire attack on the supply of the bigger companies. And because they can’t counter immediate to protect their margin, supply moves to you. Not enough that you get high reliability initially, but enough that people can at least get their car in 10 minutes. And you charge 50-60% of the price point.
So what happens? College students move. Economy-minded people move. And then over time, there is enough demand that organically supply also comes. It’s not just about low commission anymore. This strategy does not work if you want uncapped marketshare and revenue.
You can’t ever get to 50% market share because a lot of people still want high reliability. They want better cars and drivers. And the established players will always play with driver incentives to ensure high reliability and prevent their best drivers from churning. Customers also want customer support. Better safety. They want better service. More options. But then you’ll be able to capture somewhere between 20 to 30% market share in the long term. Not immediately, but long-term.
And if you see Namma and Rapido in India, of course, their GTV will be same as Ola Uber because AOV is same. But their revenue will be far lower because of the commission structure. Now Uber can’t ever operate this model because they can’t reduce their revenue. They can’t kill their margin. They are a public company. They move slow. They have to report their earnings and for a public company, you can’t show margin/ revenue decline. You want to show your take rate has actually increased because of your platform play.
Yes, Rapido could win in Bike transport.Swiggy could not even operate in that market because as a leader in food delivery you can’t enter regulatory grey areas like Bike transport. You will attract attention of regulators and safety issues would have impacted their IPO plan.
Once the infra for Bike transport is ready, you can use the same allocation logic, pricing systems, playbook to acquire drivers when you expand horizontally to car and auto.
But the real reason Rapido grew was because they had a differentiated BUSINESS MODEL ( almost no demand side incentives, supply paid fixed fee or low commission per ride). As a challenger they would do all of this while Ola and Uber could not.
Now, this is just one example. I can talk about all the examples mentioned here and why some of them have worked. Some of them seem to have worked, but long-term, it’s unclear if they are sustainable businesses. And if I had to build a product that is a challenger to Swiggy, I won’t build the same product with the same supply and demand. I won’t say, “It is the same product, but you can get your food in 10 minutes.”
Because it’s not about getting the food in 10 minutes. It’s also about how you have a differentiated supply strategy and demand strategy. Has the business model changed? Why won’t Swiggy also launch the same 10 minute product? And guess what? They did.
There are more examples beyond on demand space.
Every one is betting on vertical agents. Incumbents are building their own agents. Enso has taken a contrarian bet on horizontal agents at a fixed price for SMBs. They are building an agent marketplace too. Hit on quality and reliability, but instead of complex multiple agent workflow, it is a bet on single task agents and a marketplace approach.
Everyone was betting on bigger foundational models, Nous Research went after fine-tuning open source models. Bet on open source models. Now they are building a decentralized AI training network on Solana.
11X ai and multiple other AI SDR agents were going after the outbound, while it is very easy for Clay (CRM with leads), Apollo (source of leads) to just build the agent that does outbound. They own the source of record or own the leads (first step in the funnel). What Day AI is doing? Completely reimagining the CRM so that source of record argument is not even valid anymore.
Will these companies work and become unicorns? Who knows, but atleast there is an unique play.
Coming back to Tj’s original tweet:
It is not about hustle. It is about counter positioning. It is not about incumbents being slow, it is about them not being able to kill their margin structure. It is about a different narrative altogether. It is about different business model that incumbent will find hard to pivot to.
It is more than a simple David beats Goliath because of David grinding narrative.
2025-03-16 08:00:00
A lot of people don’t know this, but Gojek is the only true multi-modal ridehailing company in the world.
You can book all legs of the journey in a single transaction:
Every good business should have a business equation. Here is ours:
People booking public transit × % of them booking online × % booking online through Gojek × us upselling the entire journey (all the legs) and converting only the middle mile transaction to a full journey (multi modal) transaction.
First factor is macro. You can’t control it much. Second is also macro, but you can teach users why booking online is better: simpler, cashless. You have to build a killer experience for the 3rd factor to happen: seamless integration with transit services. Last factor requires product integration. How can you make the multi-modal booking seamless? How can users just tap a button to complete the last leg? Can we track the state of the booking (all legs) at all times? Can you let them edit destinations when needed, or change trains if needed?
Over time, you integrate with more public transit options despite regulatory hurdles. This can become your moat. Commute contributes to 20+% of most ride-hailing apps, so building more flexibility in commute is important. Giving economy options is important.
You also expand your market by onboarding economy users who are used to public transit. Get them on your platform through transit ticket purchases, and later upsell them to non-commute, non-transit regular 2W rides, and then 4W.
You need to integrate all ride-hailing options over time, including premium options of relevant vehicle types and more vehicle types. This isn’t easy because you need to think through pickup and drop-off experiences offline. Bikes can have designated zones to park. More space is needed for cars, and car parking is harder.
I was thinking whether Rapido can do this in India, but the actual bottleneck is auto unions. They won’t let 2W ride-hailing kill their business even though it is far more efficient in traffic and affordable.
2025-03-15 08:00:00
Actually, the best time to build White Hat Jnr was now. It got started ahead of its time.
Instead of call center agents with zero tech knowledge reading computer programs from a script, this time an AI agent would be the personal tutor for your kid.
Human motivation does not change. Parents still want their kids to get ahead in life and get an early start. But 1-1 personal tutoring is finally possible at scale due to AI agents.
2025-03-14 08:00:00
I am very bullish on nepotism making a comeback once AGI is here.
If AGI truly levels the playing field in terms of skill, anyone can perform coding tasks and delegate thinking to a model, then hiring decisions shift from “who’s the most capable?” to “who do I trust the most?”
And trust, historically, defaults to family and close networks.
“Nepo capitalism” in an AGI world makes sense because, if execution is democratized, then access and control become the new power levers. Families will consolidate wealth by hiring within, knowing that any skill gaps can be filled by AI. Instead of Patel family motels in America, it will be Patel family SaaS empire, where every uncle and their cousin will be a “founder” while AGI does the heavy lifting.
(And there will be Leuva Patidar Samaj volleyball tournaments in Dallas, but this time not for motel or gas station owners in rural America, but SaaS business owners in SF. IWKYK.)
2025-03-13 08:00:00
There is always a queue.
Every marketplace claims to be homogeneous and insists it does not differentiate between its demand and supply, but this is not true.
Marketplaces essentially function as a queue management system, balancing demand (users who want something) and supply (those who provide it).
The goal is to organize demand and supply into clear queues. Once structured, the marketplace can dynamically adjust priority based on users’ willingness to pay and suppliers’ willingness to be utilized.
When many users request rides at the same time, their requests form a queue. Typically, matching a user with a driver takes 10 to 30 seconds.
Jumping the Queue: Users can move ahead in the queue by showing a willingness to pay more, which can be done through:
Waiting to Save: Some users prefer to save money by waiting longer or booking at off-peak times. By accepting a lower priority, they pay less. Suppliers can choose to accept these users when demand is low or ignore these bids. It is up to them to decide how to maximize earnings per hour. In some cases, as a user you can even negotiate the price down instead of up if there is sufficient competition among suppliers while demand remains low. There are marketplaces where suppliers bid and the users select rather than the other way around. There are ride-hailing companies that even let drivers purchase a small booster that increases their order income by X% for the next Y hours. This is essentially paying to opt into a higher surge or bonus bracket; while it might seem counterintuitive (drivers paying the platform), some drivers use it strategically when they know demand will be high to maximize their earnings.
This principle extends beyond ride-hailing.
Home Services (Urban Company): Users who pay a premium receive faster service allocation. Others can opt for standard pricing or book during low-demand hours for lower rates.
Restaurant Reservations: At peak times, users may pay extra (a cover charge or premium) to secure prime time slots. Conversely, restaurants offer discounts during off-peak hours to attract customers when demand is low.
Summary: Marketplace efficiency relies on a dynamic queue system—where a user’s position is determined by how much they’re willing to pay and how long they’re willing to wait. The same applies to suppliers. This is a way to maximize revenue and optimize utilization.