June 15, 2026Episode 1648 min
How Deals Go to Die in DD
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.
Episodes
166
Latest episode
Jun 2026
Language
EN
About the show
Treeside Capital invests in RV and mobile home parks across the Midwest and Southeast. We share real stories of buying, improving, and operating parks — from financing and management to investor strategy — helping you learn how to build lasting wealth through outdoor hospitality and affordable housing. At Treeside Capital, we buy, improve, and operate RV and mobile home parks across the Midwest and Southeast. Our mission is to create clean, affordable, and community-focused places for people to live and travel. Each episode explores the business behind outdoor hospitality and affordable housing — from deal structure and financing to operations, management, and investor strategy. Whether you're an investor, park owner, or just curious about the industry, Treeside Capital pulls back the curtain on how to find value, solve problems, and build long-term wealth in the RV and mobile-home park space.
Listen to episodes
June 8, 2026Episode 1628 min
Follow-Up Is the Deal: Pipeline Organization for MHP Investors
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 timeline, to the tools and sequences that keep our outreach personal at scale — this is the operational side of off-market deal-finding most investors never talk about. Visit treesidecapital.com for more details
June 8, 2026Episode 636 min
AI & Mobile Home Parks — The Learning Curve, The Use Cases, and Whether It's Worth Your Time
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 learning curve: what takes time to figure out, what clicks fast, and what you can start doing this week without any technical background. Topics covered: What AI is actually good at in the MHP space (underwriting templates, LOI drafts, seller scripts, market research, investor updates) Where it still needs your judgment and local knowledge How to think about prompting — the skill that separates good output from garbage output The time investment to get useful with it vs. the return you get back Whether a small operator or solo acquisitions person should bother learning it now If you've been on the fence about AI, this episode cuts through the noise and gives you a practical, operator-level take — no hype, no tech jargon. Visit treesidecapital.com for more info.
June 3, 2026Episode 1616 min
How to Sell Your Mobile Home Park for the Highest Price — What Buyers Actually Look At
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 financial package — your P&L, trailing NOI, rent roll, and expense detail — and explain why the way you present these documents is just as important as the numbers themselves. We get into utility bills, how master-metered vs. sub-metered electric changes your valuation, and why implementing RUBS before a sale is one of the highest-ROI moves an operator can make. Then we go on-site. Roads, trees, signage, abandoned homes, common areas — buyers are doing a visual risk assessment the second they pull in. We tell you exactly what to fix and what to skip, and explain why a $8K road patch can be worth $50K+ in perceived value at closing. We also cover the one document that kills more MHP deals than any other: home titles. If your park-owned homes have missing, incorrect, or wrong-entity titles, you could be looking at a delayed or dead closing. We explain how to run a title audit and how long it actually takes to get clean. Finally, we cover the legal and compliance layer — permits, zoning, open violations, active evictions, and when you need a Phase I — and we close with the six highest-ROI moves to make before you list. If you own a park and you're thinking about selling in the next 1–5 years, this episode is your playbook. Visit treesidecapital.com for more details
June 1, 2026Episode 16012 min
The Real Math Behind Deal-Finding
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 invested capital. A single wholesale fee can match what some people earn in an entire year at their W-2. So how do you structure a system that makes the math work in your favor — whether you're looking to wholesale a deal, bring it to a capital partner, or buy it yourself? We're getting into the specifics: direct mail costs, skip trace lists, follow-up sequences, conversion rates, and what a real acquisition pipeline looks like from first touch to closed deal. If you've ever wondered whether the grind of deal finding is worth it, this episode answers that question with real numbers. Visit treesidecapital.com for more details
May 27, 2026Episode 1594 min
Honest Conversations Are The Best? Hurting People's Feelings
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 avoid. If your reputation is your currency in this business, honesty isn't optional. Visit treesidecapital.com for more details
May 20, 2026Episode 1579 min
Stop Underwriting Fantasy Deals
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.
May 20, 2026Episode 1579 min
Stop Underwriting Fantasy Deals
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.
May 18, 2026Episode 1566 min
Finding Opportunities Out of Thin Air?
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 — talk to everyone. Buyers, sellers, brokers, operators, the guy at the chamber of commerce breakfast. You don't know what they're sitting on, who they're connected to, or what they're trying to move. Most people are transactional. The ones who win long-term treat every relationship like a two-way door. Miles talks through how staying curious and generous in conversations — even ones that don't seem relevant on the surface — has led to some of the best opportunities in his portfolio. The pipeline isn't just built on deals. It's built on conversations. Visit treesidecapital.com for more details
May 13, 2026Episode 15512 min
The Art of the Hard Conversation: Bridging the Gap Between Reality and Vision
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 no longer makes sense, a lender who needs to understand why the proforma changed, or a team of employees who can feel the tension of a transition — the skill is the same. It starts with intellectual honesty about what's broken, grounds itself in the why behind what needs to change, and ends with a clear-eyed picture of where you're going together. We break down how to frame hard truths without blowing up the table, how to lead with the vision while still honoring the reality, and how the best operators earn trust not by avoiding conflict — but by navigating it with clarity and intention. If you've ever walked into a room knowing you had to say something no one wanted to hear, this one's for you. Visit treesidecapital.com for more information.
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