In partnership with

Happy Sunday!

Hope your weekend is treating you well. Mine has been a mix of coffee, deal memos, and trying to convince myself I don't need to refresh my inbox — you know how it goes.

I'm genuinely excited about this week's issue. If you've been around me for a while, you know I don't feature people just to fill space. Jeff Hurst, CEO of Furnished Finder, is someone I've been watching and rooting for long before he stepped into the top seat. He came on Money Memories, so bringing him into 5 Questions felt like a natural next step.

But first, a couple of things from me:

I'm sourcing for 2 upcoming Forbes pieces

  • Gray markets in emerging economies

  • What the LP landscape actually looks like right now for emerging managers raising their first or second fund

If you have a source, I'm accepting introductions through April 10.

Paid Subscriber Perks

I'm actively working on three deal opportunities I'll be opening up to this community — two at the intersection of fintech infrastructure and healthcare, and one fast-growing Series A fintech backed by leading GPs. Paid subscribers will get curated access to proprietary dealflow and a seat in an exclusive Slack channel I'm putting together for exactly this kind of thing. You’ll also be able to access exclusive bonus content from 5 Questions With guests.

More soon — but if upgrading has been on your mind, consider this your nudge.

MEET JEFF HURST

Jeff Hurst, CEO, Furnished Finder

Jeff Hurst has spent his career at the intersection of travel, real estate, and marketplace businesses. Before taking the helm at Furnished Finder, he held leadership roles at Expedia and VRBO — giving him a rare, ground-level view of how flexible housing markets evolve. As President and CEO, Jeff has repositioned Furnished Finder as the go-to platform for midterm rentals, carving out a distinct lane between the short-term vacation market and traditional long-term leases.

5 QUESTIONS WITH JEFF HURST

1. What core problem in housing or workforce mobility do you think the market misunderstood early on

The market did not understand the niche of a 30 day furnished rental. It is just different enough from a short-term vacation home or a long term lease, that it has a unique audience (value conscious professionals) with unique needs. Apartments.com has almost 2 million homes for rent in the US, but only 5% is furnished and eligible for a flexible term lease. Airbnb has built a large business within a business, but tenants object to the fees and lack of inventory that can be extended.

Furnished Finder saw an opportunity in the middle.

The market did not understand the niche of a 30 day furnished rental.

2. How do you describe what the business actually does when explaining it to partners or customers?

We are a classified consumer marketplace. We are somewhere between Airbnb and Zillow, with our differentiation being that we are more focused on independent landlords than Zillow (almost 6X as much inventory as them, and almost none from large multi-family properties) — but much more value oriented than Airbnb (we don’t have fees and let tenants talk directly to landlords).

We have the most in common with what VRBO looked like 15 years ago.

3. What is a decision the company made that slowed growth or limited optionality in the short term, but ultimately strengthened the business model or customer trust over the long term?

We slowed our inventory growth rates by raising prices shortly after I joined in late 2023.

We were a $99 per year subscription and simply did not have the economic resources to invest in the product as much as the category deserved. It took us over a year to regain our unit growth, but now have a much stronger tech stack, product and team to help the category grow for decades instead of years.

4. Was there a metric, customer pattern, or operational insight that materially changed how the team thought about the business or prioritized resources?

We saw our landlord net promoter score (NPS) deteriorating as a result of perceived lead quality deterioration. It was a great signal for us to get under the hood and make larger investments in fraud detection and prevention - saving our landlords (and us) time and money.

Tracking NPS and understanding drivers (and the verbatim comments beyond them) has facilitated many deep conversations with customers and also helped us shift priorities.

It took us over a year to regain our unit growth, but now have a much stronger tech stack.

5. What's being underestimated right now that will define the next five years?

I don’t see any trend breaks that will help improve the housing crisis in terms of supply and affordability.

Given that we are not structurally solving the root cause of supply, the likely shift will be a continual trend towards renting instead of owning.

Within this trend, I expect the under-appreciated aspect is how much inventory is owned by the Baby Boomer and X Generations. Many of them do not need to tap the equity in their homes, so may increasingly choose to rent them out rather than sell them at a discount to their perceived worth.

If you’d like to be featured in an upcoming 5 Questions, reply to this email. In the meantime, here’s how you can support Bear and the Bull:

  • 🤝 Become a sponsor and reach a curated audience of tech and VC buyers

  • 👇 Click on the link below

The ones showing up in LLMs convert 3× better than Google

They optimized for LLMs, not just Google.

FAQs. Comparison pages. Transparent pricing. LinkedIn presence. These aren't vanity plays. They're what gets you cited in ChatGPT, Gemini, and Claude when your buyers are researching, your investors are looking, and your future hires are deciding where to work.

Download the free AEO Playbook for Startups from HubSpot and get the exact checklist. Five minutes to read.

Till next week,

Ilona

What is one thing you wish people evaluating businesses like yours better understood about building and operating in this category?

logo

Subscribe to our premium content to read the rest.

Like what you have read so far? Become a paid subscriber to access the full archive, exclusive deep dives, market maps, and insights from founders and operators at the cutting edge of innovation.

Upgrade

Reply

Avatar

or to participate

Keep Reading