Introducing Summer: Accessible Second Home Ownership

Dec 19, 2022, written by Dennis Shirshikov

Growing up in New England, I had a friend or two whose parents had been fortunate enough to own a beach home in Cape Cod, or a mountain home in Vermont. I always enjoyed visiting when invited, and noticed how much meaning it brought to their families. It was somewhere that was special - a place for them to unplug, recharge, and reconnect with each other and their surroundings. In some cases, the home had been in their family for generations, passed down from a grandparent or parent. My family couldn’t justify the costs of owning a second home, and there was no way to lower your costs of ownership back then. I remember thinking how I’d love to own a second home myself one day - if I could afford it - somewhere I could unplug and spend meaningful time with friends and family.

Today I’m thrilled to share that Summer is coming out of stealth and we’re officially launching our product to create more accessible second home ownership. To help us do that, we’ve raised a $13.4M Series Seed, led by QED Investors and Lightspeed Venture Partners with participation from 1Sharpe Ventures, firstminute Capital and a roster of industry angel investors.

We started with a mission - create access to second homeownership. 

I left Airbnb in 2020 after 2 years leading Product, Strategy, and Operations teams across various parts of the business. One thing that had always stood out was how dependent the business was on the best hosts, the ones who manage the highest quality short-term rentals on the platform. These are the homes that are constantly in demand - they have the highest reviews and are almost always occupied - because they’re consistent. Consumers know what they’re getting, and are willing to pay a little extra for that. By design, Airbnb doesn’t manage their own listings. Therefore, it was always very hard to ensure that all of our hosts shared this view of quality. 

I began to think more about this problem in relation to what was happening in our world at that time. Folks were traveling more than ever and living more flexibly. Many folks started to see the value of having somewhere to call home that isn’t your primary residence, and in some cases were making this their first purchase. However, there was still no easy way to do this, and most people were still held back by:

Some fractional models had started gaining traction, but those always felt like sacrificing all the benefits of whole ownership in an effort to reduce your costs.

Some fractional models had started gaining traction, but those always felt like sacrificing all the benefits of whole ownership in an effort to reduce your costs. It wouldn’t seem like my home if I couldn’t go when I wanted to, have a say in how my space looks and feels, or be able to sell the home myself one day and benefit from the appreciated value. 

In discussing these trends with friends and connections, it was clear there were folks who agreed there was a better way. Luke Sherwin, Gabe Flateman, and Neil Parikh, co-founders of Casper, were the earliest investors and believers in Summer, working to give feedback and help refine our offering. Most importantly, I met my co-founder and partner at Summer, Woods Buckley. A fellow Airbnb alum, Woods and I began discussing solutions to this problem, passions for the space, and our shared vision for creating a long-lasting company that meaningfully impacted those around us. Woods had his own experience with second home ownership, cherishing the time he spent with his family at their home in Hawaii. The idea of creating access around that lifestyle in a way that made financial sense for a consumer was something that resonated with us, and coming from Airbnb, it felt like we were perfectly set up with the solution to this problem.

This article was written by
Dennis Shirshikov

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