Full Transcript

Jason Kirby: Hey everyone, welcome back. Today we have Paul on the show with us today. Thanks for joining us, Paul.

Paul Kromidas: Thanks for having me, Jason. Pleasure to be here.

Jason Kirby: Yeah, so Paul is the founder and CEO of Summer and they have gone on to raise over $80 million. So Paul, I'm so excited to hear about your story, your journey and how you've gotten to where you are today. Would you mind just giving a little bit of color about your background and what led you to starting Summer for the audience?

Paul Kromidas: Yeah, before I got started on Summer, I had a variety of roles, which I think all kind of played a role in the entrepreneurial journey in terms of getting there. Started my career in more form of finance, the credit world, sort of underpins. I still think back to some of those lessons when I'm negotiating debt facilities and talking to lenders right now. I think being able to speak that language a little bit has certainly been helpful on the journey and know what it's like to go into those offices and talk to those types of people. Moved over to management consulting, strategy and operations work, M&A work after that. And I have a lot to bring forth from that experience that I think led me into what I'm doing now as a founder. But then most relevantly, that world, being M&A, led me to Airbnb. So I was at Airbnb for a number of years, initially through an acquisition they were doing, helped them lead that acquisition, bring that company in, figure out what to do with it. And then I stuck around after that and actually led a product team there, building out consumer‑facing products for a number of years and strategy operations work as well on the side there. And I sort of had the core idea come to me while I was there.

Paul Kromidas: One of the things I noticed—anyone who’s used Airbnb has probably figured this out—is that quality hosts do very well on the platform. People who can drive whatever the moniker is—and Airbnb has changed it a lot. There was Superhost, there was Airbnb Plus, now it's Guest Choice. I'm a Guest Choice as well—Summer Homes are Guest Choice Homes, that's great. Whatever we call it, they’re hitting the core principle: quality stays, consistent five‑star reviews, professional photography, the amenities you expect.

Jason Kirby: Yeah. I'm making a choice. Yeah.

Paul Kromidas: Those homes will perform better than someone taking a home, throwing some IKEA furniture in, and putting up a couple of grainy iPhone pictures. And maybe there are some questionable rules. I've got kids—you understand where I'm coming from. You don't want anything to go wrong. You want to book quality, and you can charge a premium for that. Those homes are booked more than others. The thing I noticed at Airbnb was we could not onboard enough of that supply fast enough. It’s a marketplace—supply and demand. There’s a lot of demand, but not enough supply. Why? I started to unpack this. Individual owners of these properties—the ones who currently own them or want to own them—are often ill‑equipped for what is, at the end of the day, a distributed hospitality operation.

Paul Kromidas: How are you creating an experience on the ground akin to staying in a hotel? People don’t book short‑term rentals to stay in a hotel—you know you’re not getting the Courtyard Marriott—but too many get lost in the shuffle and don’t think consumer‑first. If I’m requiring someone to take out the trash—there are all these jokes online—bag this, do that, five locks. What kind of experience is that? People get annoyed. They’re consumers, and not everyone has a consumer‑facing mindset.

Paul Kromidas: So I started to think through: customers buying these homes need to get more out of them, or buy new ones and remove risk. People can make money doing it, but it’s risky and time‑consuming, and people don’t understand the data. The idea for Summer came from that: can we increase supply in short‑term rental marketplaces—Airbnb, Vrbo, etc.—and our own platform, by linearizing the process? We run homes through data and underwriting to understand what they’ll make—not boosted numbers. We can say this home on this block will generate this much—whether you already own it or want to buy it, here’s how to maximize it.

Paul Kromidas: We will finance that purchase if you want to buy new, or finance improvements to your current property. And we will manage the home, price it, and generate the yield—under a trusted brand, Summer Homes—well known to renters and owners as a quality operator that cares for assets like their own. We find strong feedback loops that build a network resonating with consumers.

Jason Kirby: I'm glad you gave the overview of Summer and how relevant your background was—especially those Airbnb insights and seeing the supply/demand problem. Did you ever have your own property prior to doing this yourself, or did you jump into it?

Paul Kromidas: It’s crazy, actually—no. I did not own or operate a short‑term rental officially. I’d been adjacent to it for many years at Airbnb—looked at numbers, talked to owners. I wore different hats, but my last was on the product team. A big job of any product person is consumer focus: who you’re building for. At Airbnb, there are two customers: hosts and guests. I had the fortune of working on both ends—talking to hosts constantly. Brian always emphasizes how important hosts are; you walk through the halls and see pictures of actual hosts to remind you who we serve.

Paul Kromidas: You get to know their pain points and try to solve them. Airbnb wants to remain a marketplace, keeping operational and financial pieces at arm’s length. That’s an opportunity for us to do both, plus build technology.

Jason Kirby: The show’s about fundraising, but I want to get into the model. You raised a sizable debt facility to make this a reality.

Jason Kirby: Whereas most are glorified property managers, you actually finance the deal. Why choose the financing route and take on that risk along with the homeowner?

Paul Kromidas: The initial thought was helping more people become owners—get the vacation‑home experience in a way that makes sense. We were building a top‑of‑funnel algorithm proven to be accurate at finding the right homes and informing investment decisions. Think of someone driving to view homes and wondering which is good. Our “mass affluent” customer can transact but has higher risk aversion because it’s an outsized portion of their savings—so they’re thoughtful.

Paul Kromidas: Many already own homes and want more yield. We can advise what to improve and help finance it. For new buyers, we created gradual ownership. If we’re confident—starting with our technology—we’ll buy the home, let you rent‑to‑own for up to two years, operate it and show performance that matches our underwriting. Then you can buy it back de‑risked, with five‑star reviews and proven yields. I’m comfortable taking that risk because I’m confident in our numbers. It differentiates us from straight property managers and creates more owners in a risk‑reduced way.

Jason Kirby: Fundraising can be tough for models adjacent to real estate. Early on, what was your fundraising experience like—strategy, first round—easy or a crazy journey?

Paul Kromidas: We raised our seed at the end of 2021—a different world. Looking back, valuations and expectations were inflated across proptech, fintech—everything. We only took one round in that environment, which gave us time to right‑size as we grew—something I didn’t grasp before. You get a term sheet and a big valuation and think, “I did it!” But you must prove it each round; if not, it’ll bite you later. The blessing: I had strong founder‑market fit—Airbnb, product, strategy/ops, finance. VCs wanted to talk. Had I started this year, I might not have done it; there’s an initial quantum of capital required. That environment enabled the initial injection; today’s is healthier—provided you can fundraise.

Jason Kirby: You leveraged timing and got an $11M seed. When did you close your Series A?

Paul Kromidas: Over the summer. We announced about a month ago—summer can be tough for PR with OOO. We picked up a little more in September and got it out before year‑end. We closed an $18M Series A. Different ecosystem than 2021—night and day. Our 2021 seed took ~two months from start to wired money; multiple term sheets. For the A, tables have turned: VCs are pickier, diligence takes longer. Give yourself time—add at least three months to whatever you think.

Jason Kirby: Why that A‑round strategy? You raised $18M equity and secured a $50M debt facility—how did you decide amounts and vehicles?

Paul Kromidas: In August 2022, I saw storm clouds: rates rising fast. I wanted to batten down the hatches and make it through. We had traction and PMF. I told the board I’d go raise. One insider offered to lead the A; quick diligence into the holidays taught me: don’t start in Nov/Dec (or mid‑summer). Be ready Jan 2 and after Labor Day; wrap by July 4 or Thanksgiving. I re‑architected our story and hit January aggressively. The goal: responsible growth and a path to profitability, with enough runway through macro uncertainty.

Jason Kirby: Will you need to raise more?

Paul Kromidas: Be opportunistic with the right partners, but we don’t need a giant slug. We’re running the business assuming we won’t raise more—prepare for the worst and be pleasantly surprised otherwise.

Jason Kirby: There are other funded players. How did you pick investors and differentiate from them for a venture‑backed outcome?

Paul Kromidas: Investors pattern‑match to comps, but the best companies often lack exact comps. We differentiated on three axes: (1) Brand—a consumer brand is rare in proptech; lessons from Airbnb show brand drives outcomes. (2) Fintech—our financing mechanisms and cost‑of‑capital expertise appeal to fintech investors. (3) Technology—underwriting and pricing tools. I targeted subject‑matter investors in those pockets vs. generalists, tailoring the narrative to their theses.

Jason Kirby: Founders often deliver one elevator pitch to everyone, but investors need the right framing to “put you in their box.”

Paul Kromidas: Exactly. I put my product hat on and built empathy for my customer—the VC. I wrote an investor memo that answered what they’d need for IC, using a template from an insider. It forces you to see your business through their lens and makes digging in easier.

Jason Kirby: About the $50M debt facility—how did you approach and structure it?

Paul Kromidas: Many founders lack debt‑capital experience. Even small things—how banks work, how they talk—matter. Speak the customer’s language. But founders can miss hidden terms: covenants, required liquidity, triggers that can put you out of business. I hired a capital‑markets advisor (ex‑JP Morgan MD) to help underwrite the debt, model scenarios, and negotiate. He later became our CFO. If your business uses debt, hire that expertise early.

Jason Kirby: Great leadership lesson: know when to bring in experts and skip the learning curve when you can. As we wrap, what advice do you have for founders planning to raise?

Paul Kromidas: Start earlier than you think. Have empathy—tailor to their objectives. Move fast and parallel‑path; run a structured process. Don’t take rejection personally—there are many unseen reasons. Ask for feedback and keep doors open. And cultivate tenacity. You’ll get knocked down. Keep recalibrating until you get it done.

Jason Kirby: Appreciate it—though you gave me a little PTSD from past rounds! For founders who enjoyed this, where can they learn more about you and Summer?

Paul Kromidas: I’m on LinkedIn and X (not TikTok!). Check out gosummer.com and our socials @StartSummering.

Jason Kirby: I love that. I want a Summer—especially now. Rain and cold… Summer sounds nice.

Paul Kromidas: Summer is a state of mind.

Jason Kirby: I do love winter sports—snow and cold, not rain and cold. Appreciate you being on the show, Paul. Tons of valuable insights.

Paul Kromidas: Thank you very much for having me, Jason.

Jason Kirby: Have a good one.