May 28, 2025
A Q&A with QED's partner, head of growth, Chuckie Reddy and Wander's CMO, Kyle Tibbitts
Today, Wander, a luxury vacation rental company known for its curated selection of premium properties, hotel-grade amenities and personalized concierge service, announced its $50 million Series B led by QED Investors.
QED’s partner, Head of Growth Chuckie Reddy, sat down with Wander’s Chief Marketing Officer Kyle Tibbitts to dive deeper into our decision to invest in the company’s Series A and Series B rounds and discuss how this investment aligns with QED’s goals.
Kyle Tibbitts: Why did you invest in Wander's Series B?
Chuckie Reddy: Thematically, I have been very bullish about the short-term rental (STR) sector. It’s massive and growing. Additionally, STR hasn’t been institutionalized like Single-Family Rental (SFR), which began in 2011/2012 and now has tens of billions of dollars in the strategy from large institutional investors. There is a real opportunity to provide the underpinning for that development. Wander has created a very impressive visible brand with exacting brand standards. They have also built a custom “operating system” from scratch called WanderOS. The ability to make this an engine for STR operators has real potential to help drive outsized economics for those operators. The next leg of growth for the sector could be spurred by efficiencies that WanderOS can drive.
Kyle Tibbitts: QED led Wander’s series A - what did you see back then that sparked conviction in this company, even before we had any revenue? What made you want to double down?
Chuckie Reddy: John Andrew is an amazing founder. His obsession with product and ability to drive a technology-first agenda was key to the initial conviction. The notion of building a brand in the STR sector was very appealing. We shared a vision of how to institutionalize the asset class and how that would ultimately benefit the guest. Unlike other models, focusing on the guest first was an important principle. By doubling down, Wander has demonstrated that they have delivered on the brand promise. CSAT and NPS scores show how much guests love the Wander experience. As mentioned, Wander now also has a fully built-out WanderOS, which has tremendous potential across the industry.
Kyle Tibbitts: How does the investment in Wander align with QED's goals/thesis?
Chuckie Reddy: QED is a global fintech VC firm. One of our vectors is the asset management space. We have made large investments in the SFR asset class. As such, we believe that STR could be the next large asset class. Investing in companies that can serve as asset managers or tools in the space is the best way to invest in this theme. Wander has proven it can be a direct manager and also provide the tooling for others to manage these assets. As we look forward, this sector will consolidate and WanderOS can enable that.
Kyle Tibbitts: What is it about John Andrew Entwistle that makes this bet on Wander make sense?
Chuckie Reddy: John Andrew is a third-time founder despite being only 27. While young, he knows how to be very deliberate about testing and learning. When something isn’t working, John Andrew is willing to shift and change as necessary. That nimbleness has been a key element of Wander’s success. John Andrew is also a true technical leader. He has the ability to hire and retain top engineering talent. Code ships incredibly fast at Wander. Upgrades are continuous and a direct result of learning from everyday operations.
Kyle Tibbitts: Finish this sentence: A bet on Wander is a bet on.____"
Chuckie Reddy: …Guests wanting a truly differentiated vacation experience. Wander has incredible properties in its portfolio. From the moment you book to the moment you drive away, Wander strives to create an incredible guest experience. From property selection to the concierge, the guests' happiness is of utmost importance to the company.
Kyle Tibbitts: Something lighter: "What does it mean to you to 'Find your happy place?" or "What's your favorite Wander that you've ever stayed in?" or "What is the next Wander you want to travel to?"
Chuckie Reddy: If asked the question of ski vs. beach, I’ll always pick ski. I’ve never had the chance to ski Telluride. Wander Telluride Ridge might be too big of a house for my needs, but the property both looks incredible and is very well situated to get the first chair!
Today, Wander, a luxury vacation rental company known for its curated selection of premium properties, hotel-grade amenities and personalized concierge service, announced its $50 million Series B led by QED Investors.
QED’s partner, Head of Growth Chuckie Reddy, sat down with Wander’s Chief Marketing Officer Kyle Tibbitts to dive deeper into our decision to invest in the company’s Series A and Series B rounds and discuss how this investment aligns with QED’s goals.
Kyle Tibbitts: Why did you invest in Wander's Series B?
Chuckie Reddy: Thematically, I have been very bullish about the short-term rental (STR) sector. It’s massive and growing. Additionally, STR hasn’t been institutionalized like Single-Family Rental (SFR), which began in 2011/2012 and now has tens of billions of dollars in the strategy from large institutional investors. There is a real opportunity to provide the underpinning for that development. Wander has created a very impressive visible brand with exacting brand standards. They have also built a custom “operating system” from scratch called WanderOS. The ability to make this an engine for STR operators has real potential to help drive outsized economics for those operators. The next leg of growth for the sector could be spurred by efficiencies that WanderOS can drive.
Kyle Tibbitts: QED led Wander’s series A - what did you see back then that sparked conviction in this company, even before we had any revenue? What made you want to double down?
Chuckie Reddy: John Andrew is an amazing founder. His obsession with product and ability to drive a technology-first agenda was key to the initial conviction. The notion of building a brand in the STR sector was very appealing. We shared a vision of how to institutionalize the asset class and how that would ultimately benefit the guest. Unlike other models, focusing on the guest first was an important principle. By doubling down, Wander has demonstrated that they have delivered on the brand promise. CSAT and NPS scores show how much guests love the Wander experience. As mentioned, Wander now also has a fully built-out WanderOS, which has tremendous potential across the industry.
Kyle Tibbitts: How does the investment in Wander align with QED's goals/thesis?
Chuckie Reddy: QED is a global fintech VC firm. One of our vectors is the asset management space. We have made large investments in the SFR asset class. As such, we believe that STR could be the next large asset class. Investing in companies that can serve as asset managers or tools in the space is the best way to invest in this theme. Wander has proven it can be a direct manager and also provide the tooling for others to manage these assets. As we look forward, this sector will consolidate and WanderOS can enable that.
Kyle Tibbitts: What is it about John Andrew Entwistle that makes this bet on Wander make sense?
Chuckie Reddy: John Andrew is a third-time founder despite being only 27. While young, he knows how to be very deliberate about testing and learning. When something isn’t working, John Andrew is willing to shift and change as necessary. That nimbleness has been a key element of Wander’s success. John Andrew is also a true technical leader. He has the ability to hire and retain top engineering talent. Code ships incredibly fast at Wander. Upgrades are continuous and a direct result of learning from everyday operations.
Kyle Tibbitts: Finish this sentence: A bet on Wander is a bet on.____"
Chuckie Reddy: …Guests wanting a truly differentiated vacation experience. Wander has incredible properties in its portfolio. From the moment you book to the moment you drive away, Wander strives to create an incredible guest experience. From property selection to the concierge, the guests' happiness is of utmost importance to the company.
Kyle Tibbitts: Something lighter: "What does it mean to you to 'Find your happy place?" or "What's your favorite Wander that you've ever stayed in?" or "What is the next Wander you want to travel to?"
Chuckie Reddy: If asked the question of ski vs. beach, I’ll always pick ski. I’ve never had the chance to ski Telluride. Wander Telluride Ridge might be too big of a house for my needs, but the property both looks incredible and is very well situated to get the first chair!