Sep 9, 2019 · 25m · top-founders
1507 Guesty Passes 1,000 Customers, 50,000 Properties, Charging 2-5%
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this podcast interview, Guesty co-founder and CEO Amiad Soto explains how the short-term rental software platform scaled to manage up to 100,000 properties across 1,000 clients. Soto breaks down Guesty's 2–5% booking take-rate model, international office expansion, rapid CAC payback periods, and high net revenue retention.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 43.7% of the talking time here. How this is scored →
Nathan as informed peer 5.1 Guest teaching 3.9 Guest disagreement 3.4 Nathan pushing back 4.7
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 4:28 Amiad refuses to give a hypothetical price quote
Amiad firmly draws a boundary against Nathan's line of questioning, stating that if the goal is to force a specific price quote on air, he will not do it.
Hardest push from Nathan ▶ 22:05 Nathan demands clarity on confusing churn numbersFrustrated by convoluted explanations mixing SMB and enterprise monthly vs annual rates, Nathan bluntly tells Amiad he is being confusing and orders him to give a direct number.
Biggest teaching moment ▶ 6:06 Amiad corrects Nathan's fee calculation mathWhen Nathan assumes Guesty takes 2.5% of the property manager's $200 commission, Amiad corrects him, clarifying that the 2.5% cut applies to the full $1,000 reservation total.
Nathan holds their own ▶ 14:29 Nathan deconstructs LTV-to-CAC pitfalls and cash gapsNathan draws upon interviews with large SaaS CEOs to explain why impressive LTV:CAC multiples create dangerous cash flow deficits if payback periods exceed 12 months.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Meet Amiad Soto and the Origins of Guesty | 4 | 3 | 1 | 2 | Nathan introduces the company and asks Amiad about Guesty's founding narrative and core value proposition. Amiad explains how managing his own Airbnb rentals as a college student led him and his twin brother to build the software. The exchange is cooperative and introductory. | |
| Breakdown of Guesty Pricing Model and Customer Profiles | 6 | 6 | 7 | 8 | Nathan repeatedly presses for specific pricing figures for a hypothetical 50-property customer, prompting Amiad to flatly refuse to quote arbitrary numbers. After Nathan threatens to move on if he gets no clarity, Amiad clarifies the 2-5% take-rate structure and corrects Nathan's mistaken math on how the fee is calculated against the total reservation rather than the manager's cut. | |
| Funding Journey and Global Office Expansion Strategy | 5 | 3 | 2 | 4 | Nathan probes why Guesty raised $20M and opened multiple physical offices when inside sales previously drove rapid growth. Amiad justifies the regional expansion by noting that less tech-savvy property managers demand in-person demos and localized support. Nathan then runs through rapid operational tasks to categorize Guesty's feature set. | |
| Lead Generation Funnels and Customer Acquisition Channels | 8 | 5 | 5 | 7 | Nathan pushes past high-level LTV:CAC multiples to challenge Amiad on payback periods, warning of cash flow traps common in high-growth SaaS. A sharp disagreement arises over fully weighted CAC definitions when Amiad claims some firms omit event sponsorships from CAC calculations, which Nathan forcefully rejects based on industry practice. | |
| Scalability Metrics, Industry Fragmentation, and Automation Value | 4 | 3 | 2 | 2 | Amiad outlines Guesty's scale of 50k to 100k properties and explains how its end-to-end platform consolidates a fragmented ecosystem of over 600 niche point solutions. Nathan asks about customer revenue lift, and Amiad reframes their core selling point around workflow automation and operational hours saved. | |
| Churn Dynamics and Net Revenue Retention | 6 | 5 | 6 | 8 | Nathan presses Amiad for exact churn figures after Amiad initially offers vague generalizations about being below industry benchmarks. After confusion ensues over annual versus monthly churn benchmarks across SMB and enterprise segments, Nathan demands a direct answer, prompting Amiad to state their 1-2% monthly revenue churn. | |
| The Famous Five Rapid-Fire Questions | 3 | 2 | 1 | 2 | Nathan runs through his standard Famous Five rapid-fire questions covering favorite books, CEOs, CRM tech stack evolution, sleep habits, and early career advice. Amiad answers directly and collegially to close out the interview. |
Statements from this episode (17)
Soto: Average Guesty customer manages 50 properties, ranging up to 2,000
“The average will be a 50 properties property manager. We have as low as five and we have as big as 2000, right?”
Soto: Guesty charges property managers 2% to 5% per reservation
“It's percentage based, as I mentioned... Of the reservation. So each reservation could be a thousand dollars and then you'll pay us somewhere between two and five percent.”
Soto: Short-term rental property managers average a 20% fee payout
“Our customers are property management companies who do short term rentals and the average payout for property management companies is about 20%. There are some companies that go as much as 35 or even more.”
Soto: Guesty raised $20M Series B in April 2019, totaling $25M
“So we were Y Combinator backed back in winter 14 class. And right afterwards we raised 1.6 million as our seed. Then we raised three million as our A and only now we raised twenty million in, in April in series B.”
Soto: Guesty relied exclusively on inside sales before opening field offices
“Until now we were only inside sales.”
Soto: Guesty customers grow their property count 5x in year one
“Almost all of our customers, the average they grow in one year is more than five X.”
Soto: Property managers slow growth around 300 properties due to multi-city expansion
“We definitely help a lot of companies grow to the three hundred-ish size, and then they slow down a bit because they need to start spreading into different cities, and that's a different operation skill that they need to develop.”
Soto: Guesty generates almost 50% of web traffic organically
“So we get almost 50% of our traffic through organic.”
Soto: Guesty generates 6x to 30x LTV to CAC returns
“And we found out that we make more than six to sometimes even as much as 30 X on our on our type of customers depends on their size.”
Soto: Guesty's larger customers pay back CAC within one to three months
“So for us, it depends on the size of customers, but the medium and large ones pay back within a month to three months as a late.”
Soto: Guesty manages north of 50,000 properties, approaching 100,000
“Tens of thousands of properties north of 50,000 closer to the hundred ish.”
Soto: Over 600 niche software tools fragment the short-term rental market
“Well, you know, this industry is still super fragmented. There are more than 600 different software tools but all of them are focused on niche specific solutions.”
Soto: Property management software retention requires owner revenue tracking tools
“Whenever you give your own owner a tool that they can see their reservations, they can see how much money they're making, they can log in to change their occupancy or availability of their property, you cannot take that away from them.”