The Ledger

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Opinion
Most fractionalized investment platforms are structurally unsound, says Entwistle
“In a world where, candidly speaking, like, most of these fractionalized investment companies are not exactly sound was something I was really, really proud of.”
John Andrew May 28, 2025 ▶ 9:04 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Prediction Not checkable as stated
Entwistle predicts 95% of Wander operations will be AI-automated within 18 months
“But I see a path to what I would define as full deflection Meaning, like, 95% of these tasks being done by AI probably in the next, like, 12 to 18 months.”
John Andrew May 28, 2025 ▶ 35:52 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Opinion
Silicon Valley discriminates against older entrepreneurs, argues Entwistle
“I think that nowadays there is a culture of celebrating, you know, young founders, young entrepreneurs And so I wouldn't say that you actually have that much going against you. In fact, I would almost say a little bit of the opposite, that, like, if you are so…”
John Andrew May 28, 2025 ▶ 39:44 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Insight
Series B standard is moving to $10M-$15M ARR, says Entwistle
“I'd say that probably today the minimum threshold is around five million of ARR. But really, like, 10 to 15 is starting to become standard. The sort of goalposts have moved quite a bit, and so I'd say that's rather difficult.”
John Andrew May 28, 2025 ▶ 2:10 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Not checkable as stated
Wander is approaching a $40M gross merchandise value run rate
“We're cresting a forty million dollar GMV run rate.”
John Andrew May 28, 2025 ▶ 3:30 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Supported
Wander created the first-ever vacation rental REIT
“We, like, the first vacation rental REIT to ever exist, it was exceptionally well done.”
John Andrew May 28, 2025 ▶ 8:27 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Not checkable as stated
300,000 homes meet Wander's quality standard, representing $35B GMV
“So there's about 300,000 locations that fit the Wander standard, and those 300,000 locations represent about thirty five billion of GMV which is quite, quite a bit.”
John Andrew May 28, 2025 ▶ 12:10 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Partly supported
Wander secured a $100M Credit Suisse facility at eight months old
“And so we ended up signing up a hundred million dollar credit facility with Credit Suisse as a literal eight month old company.”
John Andrew May 28, 2025 ▶ 17:50 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Not checkable as stated
Wander operates entirely remote with zero local property managers
“You know, I think that probably the most interesting thing about Wander from a software perspective is that you have the booking engine and the booking platform, and that's the only thing that we surface to guess, but underneath you have what we call Wander OS…”
John Andrew May 28, 2025 ▶ 33:54 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Not checkable as stated
Wander's 2022 and 2023 customer cohorts exceed $10,000 LTV
“Over a three-year period, so our, like, twenty-twenty-two cohort, twenty-twenty-three cohort it has over a 10,000 dollar LTV which means that basically folks are booking once a year.”
John Andrew May 28, 2025 ▶ 51:52 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Not checkable as stated
Wander is adding 200 to 300 homes worth $1.5B this month
“The 300, you know, 203 hundred homes that we'll add this month is about 1.5 billion dollars of real estate.”
John Andrew May 28, 2025 ▶ 56:38 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Disclosure
Wander has raised over $100M in venture equity
“We raised, I think, I mean, gosh, with this round, I mean, it'll probably end up being over a hundred million dollars”
John Andrew May 28, 2025 ▶ 58:10 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Disclosure
QED led Wander's Series A and is leading its Series B
“Yeah, so the round is led by QED who is an internal investor. They led our Series A”
John Andrew May 28, 2025 ▶ 1:47 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Supported
Wander has surpassed 1,000 active locations on its platform
“We just passed a thousand locations, which is super exciting.”
John Andrew May 28, 2025 ▶ 3:04 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Not checkable as stated
Wander has grown its platform locations 14x year-over-year
“We've grown locations on platform about 14 X year over year.”
John Andrew May 28, 2025 ▶ 3:22 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Not checkable as stated
Wander achieved an 85 Net Promoter Score in Q1
“Our net promoter score is 85 for Q-one, which is super high.”
John Andrew May 28, 2025 ▶ 3:26 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Disclosure
Wander targets an $80M GMV run rate by year-end
“I think we're targeting to finish the year around 80.”
John Andrew May 28, 2025 ▶ 3:34 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Supported
Wander offered in-app Tesla unlocking just six months after launch
“When Wander launched as a six-month-old company, and you would go and stay at one of these homes, you had a Tesla that you could unlock through the app.”
John Andrew May 28, 2025 ▶ 6:22 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Not checkable as stated
Wander's Fund 1 REIT generated a 22%+ return for investors
“We closed out the fund one for the REIT. Investors got a really great return, 22 plus percent, which is really great in real estate.”
John Andrew May 28, 2025 ▶ 10:10 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Supported
The top 5% of vacation rentals account for 30% of industry revenue
“So the top five percent of vacation rentals represent about 30% of the industry's revenue.”
John Andrew May 28, 2025 ▶ 12:04 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Disclosure
Negative concierge feedback at Wander directly alerts the CEO on Slack
“Versus at Wander, literally, like we have a button in, in the concierge chat, like a thumbs up or a thumbs down, and when you hit that thumbs down button, it doesn't go into the ether, like it actually pings me on Slack.”
John Andrew May 28, 2025 ▶ 13:10 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Disclosure
Wander discontinues Tesla vehicle inclusions at its rental properties
“No, we no longer offer the Teslas at the homes.”
John Andrew May 28, 2025 ▶ 32:00 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Not checkable as stated
Automated agents handle roughly 60% of Wander property management tasks
“I'd say today we probably have about a 60% deflection rate where the items and the tickets and the coordination and communication is being handled by these agents.”
John Andrew May 28, 2025 ▶ 35:44 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Not checkable as stated
Only 35% of Wander's bookings come from paid marketing channels
“About 35% of our bookings come from higher cost channels, so think like Google and Facebook. The rest are all lower cost. So SEO influencer marketing, word of mouth”
John Andrew May 28, 2025 ▶ 51:16 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Not checkable as stated
Wander has approximately 400,000 registered users on its platform
“Wander has about 400,000 users on our platform.”
John Andrew May 28, 2025 ▶ 53:40 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Disclosure
Wander charges fees to guests and owners without marking up services
“Wander works as a take rate on gross revenue. So when someone makes a booking, we take a fee of that booking, and then we also charge a fee to the owner on the underlying revenue. We don't actually mark up any services. We don't charge any type of payment proc…”
John Andrew May 28, 2025 ▶ 55:17 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Disclosure
Wander sold most of its originally owned homes to third-party investors
“Most of our original homes have all been, you know, sold to third parties. They've all stayed on the platform. You know, they were investors or whoever else who wanted, wanted to own them. We still do own one or two from a more of like a strategic perspective”
John Andrew May 28, 2025 ▶ 56:58 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Supported
John Andrew Entwistle founded venture-backed Coder.com at age 17
“My first venture backed company, I started when I was about 17, 18. That was Coder.com.”
John Andrew May 28, 2025 ▶ 36:44 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
Assertion Not checkable as stated
Wander's team size is currently just over 100 people
“So today we're about a hundred people, but a little bit more.”
John Andrew May 28, 2025 ▶ 43:50 How Wander Raised Over $100M+ to Reinvent Luxury Travel · Sourcery with Molly O'Shea
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