Treeside Capital Podcast

Seller financing is the edge that separates one-deal investors from portfolio builders—but most get rejected before they even ask because they don't know the structure, the timing, or what to say. In this episode, we break down how to position seller financing as a better outcome for the seller than a lump-sum sale, when in the deal timeline to introduce it, and the exact language that moves selle...

You've negotiated the price. You've signed the PSA. You think the hard part is over — and that's exactly when the tax bomb goes off. In this episode, Miles breaks down one of the most overlooked and highest-stakes conversations in any mobile home park or RV park acquisition: the purchase price allocation. Whether you're the buyer building a depreciation strategy or the seller trying to protect wha...

The number one deal killer in MHP acquisitions isn't valuation — it's a seller who feels like they've been left in the dark. In this episode, Miles walks through the framework he uses to set expectations with sellers before and after signing: what DD requests are coming, why the timeline looks the way it does, and how to deliver difficult news without losing the deal. Consistent, honest communicat...

Discover all the pitfalls that can occur AFTER signing a purchase contract, and how to mitigate them to close deal.. Visit treesidecapital.com for more info.

AI is everywhere right now, and if you've been curious whether it actually applies to mobile home park investing — or if it's just another shiny object — this episode is for you. Miles walks through how Treeside Capital has integrated AI tools into the day-to-day of acquiring and operating MHPs, including real examples of where it saves hours and where it still falls short. He covers the honest le...

In the mobile home park space, the best deals rarely come from the first conversation. They come from the third, the sixth — sometimes the tenth touchpoint with a seller who wasn't ready yet. In this episode, we share the exact follow-up strategy and pipeline structure we use to stay in front of motivated sellers without letting anything slip. From how we categorize leads by motivation and timelin...

Most operators don't think about selling until they're ready to sell — and by then, they've already left money on the table. In this episode, we break down exactly what sophisticated buyers, their lenders, and their due diligence teams are scrutinizing when they underwrite your park, and what you can do in the 6–12 months before going to market to maximize your number. We walk through the full fin...

What does it actually cost to find a mobile home park deal — and is it worth it? In this episode, we break down the real numbers behind deal sourcing: the time you'll spend, the marketing dollars you'll burn, and the success rates most operators never talk about. Spoiler: the hit rate is low. But when you land the right deal, the math changes everything. One good MHP acquisition can 10x your inves...

Transparency sounds simple until money is on the line. In this episode, Miles breaks down the long game of building trust with sellers, partners, buyers, and brokers — and why cutting corners on honesty always costs more than it saves. From retrade conversations to partner alignment to telling a broker a deal won't work, this episode is a practical guide to having the conversations most investors...

Expecting 20% COC? Assuming your expenses will look like yours, not theirs? You're setting yourself up to fail. Miles breaks down the most common underwriting pitfalls — from modeling your operation over the seller's reality to ignoring vacancy, cap-ex, and management costs. Learn how to read a deal for what it actually is, not what you want it to be. Visit treesidecapital.com for more info.

Expecting 20% COC? Assuming your expenses will look like yours, not theirs? You're setting yourself up to fail. Miles breaks down the most common underwriting pitfalls — from modeling your operation over the seller's reality to ignoring vacancy, cap-ex, and management costs. Learn how to read a deal for what it actually is, not what you want it to be. Visit treesidecapital.com for more info.

The best deal you find might not come from the deal you're working — it might come from the conversation around it. In this episode, Miles breaks down a real example: while trying to sell an RV park, he discovered that his buyer was looking to sell a property of their own. One conversation. Two opportunities. It's a simple principle that changes everything about how you show up in this business —...

Every acquisition, every turnaround, every meaningful business relationship eventually arrives at a moment that tests your ability to say something uncomfortable — and say it in a way that keeps the deal, the relationship, and the trust intact. In this episode, we go deep on the art of the difficult conversation. Whether you're sitting across from a seller who's emotionally tied to a number that n...

Every acquisition, every turnaround, every meaningful business relationship eventually arrives at a moment that tests your ability to say something uncomfortable — and say it in a way that keeps the deal, the relationship, and the trust intact. In this episode, we go deep on the art of the difficult conversation. Whether you're sitting across from a seller who's emotionally tied to a number that n...

Podcasts, books, webinars, Twitter threads… it's easy to get stuck in "education mode" in mobile home park investing. But the real question is: How do you actually go from learning… to owning your first park? In this episode, we break down the real-world progression from beginner to owner—and why networking and relationships are often the missing link. We cover: The different levels of learning in...

In today's mobile home park investing landscape, trying to do everything is one of the fastest ways to burn out—or go broke. The game has changed. Higher interest rates, tighter lending, and operational complexity have created a clear divide: the investors who win are the ones who know their lane and dominate it. In this episode, we break down how to find your niche in the MHP space based on your...

One of the most uncomfortable moments in real estate investing is discovering a major issue during due diligence — a failing septic system, aging water lines, electrical problems, or infrastructure that's far worse than the seller represented. Now the real question becomes: Do you walk away… or retrade the deal? In this episode, Miles breaks down how experienced investors approach retrading when s...

Everyone loves to talk about IRR. Very few people want to talk about bank statements. In this episode, I walk through how we actually underwrite mobile home parks and small commercial deals — not the "broker OM fantasy version," but the real operator version. We'll cover: Reconciling the P&L with actual bank deposits Matching rent rolls to collections (and spotting gaps) Evaluating business licens...

Most investors analyze rent rolls, occupancy, and cap rates… but the real deal-maker (or deal-killer) is often underground. In this episode, we break down how to evaluate infrastructure when buying a mobile home park — especially private wastewater treatment plants and the potential to connect to city sewer. A property that looks like a 10% cap can quietly become a negative-cash-flow nightmare if...

Everyone talks about underwriting like it's math. It's not. It's geography. The biggest mistake I see investors make in mobile home parks is using the same assumptions everywhere — same expense ratio, same rent growth, same exit cap, same infill timeline. That works great… until it doesn't. Because a park in rural Ohio, a suburb of Atlanta, and a Midwest factory town may all have the same lot rent...

Mobile home parks aren't sexy. They are efficient. This podcast is for investors who care less about hype and more about after-tax returns, downside protection, and boring assets that quietly compound wealth. We break down how manufactured housing communities actually work—from operations and deal structure to depreciation, cost segregation, and why MHPs often punch far above their weight in tax e...

Cold calling isn't dead — it's just misunderstood. Smiling & Dialing is a no-nonsense podcast about building real direct-to-owner deals the right way: with patience, consistency, education, and trust. This show is for operators and investors who understand that the best deals take time. We dive into: How to talk to property owners like humans — not leads Why direct-to-seller deals have longer deal...

Most people underestimate how powerful consistent online presence can be — especially when it's built on honesty, experience, and patience. Years ago, posting just one thoughtful LinkedIn post per week led to investor relationships, deal flow, partnerships, and opportunities I couldn't have predicted at the time. I stepped away from that habit — and now in 2026, I'm intentionally rebuilding it. Th...

In a crowded market, marketing skill often gets confused with operating skill. In this episode, we talk about how to identify real operators—the ones who've survived tough deals, missed projections, managed downturns, and still show up accountable to investors. Topics include: Social media signals that matter—and those that don't Underwriting assumptions that separate pros from amateurs Why "no de...

What actually happens in the first 90 days after you take over a mobile home park—and what should happen if you want the property to stabilize and improve? In this episode, we break down the most critical actions new owners need to take immediately after closing: Fixing collections and establishing payment discipline Evaluating, replacing, or retraining the on-site manager Setting clear expectatio...