My First Deal - by My First Million In Multifamily
Case studies on apartment deals, focusing on first time deals! Not just the sizzle, but the ENTIRE story. Finding the deal, raising the capital, closing the deal, operations and renovations, getting through the refinance and the stabilized cash flow.
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Base Hits, Not Home Runs — How Chris Leet Turned a 19‑Unit Into a Free Triplex
09/30/2025
Base Hits, Not Home Runs — How Chris Leet Turned a 19‑Unit Into a Free Triplex
On this episode, operator Chris Leet breaks down his first apartment‑size acquisition—a 19‑unit in Frankfort, KY (16‑unit + triplex)—and how a partner backing out the week of closing forced a fast, relationships‑driven capital solve. We get into conservative underwriting, unplanned HVAC/water‑heater hits, managing rent bumps with legacy tenants, and why Chris prefers deals that pencil without interest‑only. Eighteen months in, he pivoted: split the asset, refinanced the triplex into a 30‑year loan with no cash left in, and sold the 16‑unit for $1.05M—returning investor principal early with 16–18% returns while keeping a cash‑flowing triplex. Base hits win the season. You’ll learn: • Structuring a JV vs. a syndication • How to navigate early CapEx surprises • Practical pivots: split, refi, sell • The power of rooms and relationships in raising capital Yeadon: Hey y’all, welcome back to the My First Deal Podcast by My First Million in Multifamily—the show where we tell the unvarnished truth about first deals in apartments. How do you find that first deal, move from single‑family to multifamily, raise capital, close, renovate, operate, refinance—everything all the way to stabilization. I’m excited to have Chris Leet with us today. Chris, welcome, brother. Chris: Thanks for having me. I appreciate it. Yeadon: We’ve known each other a couple of years now—two or three? Chris: Yeah, somewhere in that range. Yeadon: I’ve watched you grow your portfolio, and you just exited a 16‑unit recently, right? Chris: Yep. It started as a 19‑unit purchase. I kept the 3‑unit and sold the 16. Yeadon: Beautiful. And that 19 (the 16 plus the triplex) is today’s story—your first apartment‑size deal. Chris: That’s right—my first time going full‑cycle with partners. Yeadon: Before we dive in, how long have you been investing at any level? Chris: I bought my first place in 2019. Yeadon: So six years in. What kicked this off for you? Chris: Family and legacy. I had a daughter around that time and wanted more than just a W‑2 path. Yeadon: Still W‑2 today? Chris: I am. The job’s changed, but I’m an outside sales rep for a steel manufacturer. Yeadon: Love it. Just noting for listeners—it’s absolutely possible to build a legacy portfolio while keeping a nine‑to‑five. You don’t have to work 80 hours a week on real estate for it to work. Yeadon: What was your first acquisition—single‑family, duplex? Chris: A condo. Low‑income housing condo. Paid cash to keep the risk low and prove the concept. Yeadon: Where did you learn the ropes? Chris: Books, then a friend pointed me to BiggerPockets. I spent 6–10 months learning and picking a market. I’m from Kentucky and entry prices are lower there than in Arizona, so that’s where I focused. Yeadon: Classic starting path—books, BiggerPockets, proof‑of‑concept deal. When did the shift to apartments happen? Chris: After a few small buys. I tried the “pyramid”—2 units, then 4, 8, 16. That was the early vision. Over time I realized I wanted to go faster: HELOC on my AZ house for a 2‑unit and a 4‑unit, then an off‑market 9‑unit portfolio. Seeing the appreciation and momentum, I knew I had to scale with bigger deals and other people’s capital—speed up the velocity of money. Yeadon: Exactly—collapse a 20‑year plan into five if you learn to use OPM. What barriers did you run into going multifamily? Chris: Capital, of course. Then finding the right deal and market. And because I invest out‑of‑state, a trustworthy property manager was huge. Yeadon: AZ to Louisville/Cincinnati is a four‑and‑a‑half‑hour flight and a time‑zone jump. Not nothing. Chris: Right. I started making offers—probably 15–30 before the first duplex landed. It’s a numbers game: make offers where the numbers work until someone says yes. Yeadon: Let’s talk about the 19‑unit. When did you buy and how did it come together? Chris: 2023. It was in Frankfort, Kentucky—blue‑collar, bourbon country. An investor I knew through my agent was selling. It was under contract, but that buyer had to back out for medical reasons. I already had a relationship with the local bank doing the loan. They were willing to let me step in. Yeadon: And you didn’t have the full 20% down. Chris: Correct. I was selling an 8‑unit with the same bank. They agreed to take 10% of the down payment from those sale proceeds. That left me needing $100k cash to close the 19‑unit. Yeadon: On a just‑under‑$1M purchase—so ~$200k down, $100k covered by sale proceeds, $100k left to raise. Chris: Exactly. Yeadon: What happened next? Chris: I lined up a 50/50 partner for the $100k…and he backed out the week of closing. Then disappeared. Yeadon: Brutal. Ice‑bath level brutal. Chris: I started calling everyone. In two days I talked to 10–15 people. Brenda Gooden—through Deal Room—reviewed the underwriting and said yes. She wired in and we closed. We ended up structuring a JV: I held 55%, Brenda 45%. Yeadon: For listeners: JV means everyone is active; syndication is where some are active (GP) and others passive (LP). JV was a great fit here. Chris: We might have pushed closing a day or two, but we got it done. Yeadon: Pro‑tip: schedule closings for Thursday, not Friday—you’ll thank me later. Okay, post‑close, what did you find? Chris: The property manager—who already managed it and knew the tenants—said rents were $100–$150 under market and the property was in decent shape. New roof helped. But in months 3–6, the surprises hit: four to five HVAC replacements I hadn’t budgeted, plus five water heaters. Many tenants were long‑term and balked at rent bumps; some moved out, and older units needed bigger turns than expected. Yeadon: What were average in‑place rents and your bump plan? Chris: Around $600 in place. We aimed for $75–$100 increments—$675, $700, $750—leaning on the PM’s read of each tenant. Yeadon: Loan terms? Chris: Local bank, 25‑year amortization, 5‑year term, about 8.25% interest, no interest‑only. Yeadon: I/O can juice cash flow, but I prefer deals that work without it. What was your original CapEx plan and hold timeline? Chris: ~$50k for the 16‑unit component; we weren’t planning to touch the 3‑unit initially. Five‑to‑seven‑year hold. Then reality: $20k in HVACs and another ~$5k in water heaters in Year 1. At ~18 months, we realized to fully turn the 16 we’d need another $100k, but then we could likely push to $800–$850 rents. Yeadon: So you pivoted. Chris: We did. We split the 19: cash‑out refi on the 3‑unit into a 30‑year DSCR‑style residential loan—so no original cash left in that asset—then listed the 16. We’d also brought in a third partner along the way—Eugene Nyli—on a ~$60k 1031 exchange for a small stake. Yeadon: List at $1.2Mish—where did it land? Chris: Closed at $1.05M on the 16. That allowed us to return investor capital. Brenda and Eugene got their money back, and both earned 16–18% returns over roughly two years. We kept the triplex, now cash‑flowing $500–$600 a month with no cash in the deal. Yeadon: No capital calls, investor principal back early, modest profits, plus you own a free‑and‑clear‑basis triplex (no cash left in). That’s a win. Chris: The ROI looks smaller if you only analyze the 16’s sale—but the free triplex changes the story. Over time, amortization and appreciation make it even better. Yeadon: Options ahead: refi to lower rates later, adjust to a 15‑year to burn principal faster, or sell and take chips off the table. Lots of ways to win. Chris: Exactly. Yeadon: Recap: You started with a W‑2, learned through books and BiggerPockets, bought small, then scaled. You joined Deal Room, built relationships, missed on a bigger raise once (great reps), then on this 19 you solved a last‑minute $100k gap via the room, JV’d 55/45, later added a small 1031 partner, powered through unplanned CapEx, pivoted to split the asset, sold the 16, kept the 3, returned capital with 16–18% investor returns, and now hold a cash‑flowing triplex with no cash left in. That’s how base hits win seasons. Chris: Well said. Yeadon: What’s next for you? Chris: I’ve got ~50 units I own solo (no partners). With partners, I have an 8‑unit with Safety Gordon (Deal Room), and I just bought a portfolio—two single‑family homes and two four‑plexes—using private/hard money through 608B Capital. I also closed an 8‑unit portfolio with two duplexes and four houses. Plan: flip the houses now or rent a year and sell when the market’s better; hold the duplexes long‑term. Goal is to flip four houses this year—I’ve finished one, second is in progress. Rinse and repeat these portfolio plays: sell part, keep part with little/no cash in. Yeadon: Love the creativity. For most people, it’s hard to “think outside the box” without exposure to other operators and structures. Books and rooms expand the box—podcasts, mentors, and peers show what’s possible. Chris: I wouldn’t have gotten creative financing done on several deals without learning it from books and podcasts—and Deal Room. Yeadon: Alright, two or three concrete steps for someone getting started? Chris: 1) Educate yourself—books, podcasts, courses—but don’t become an information junkie. At some point you must act. 2) Join a group or get a mentor where you want to operate; it pays for itself on your first couple deals. 3) Be ready to pivot and make mistakes—you’ll course‑correct a thousand times. Yeadon: Amen. Learn, take action, get around doers, and don’t be afraid of mistakes—especially if you can learn from someone else’s $300k mistake. Chris, thanks for coming on. Chris: Thanks for having me. Yeadon: Listeners, this is the unvarnished truth about getting your first deal in commercial real estate. I’m your host, Yeadon. We’ll see you next time.
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Yeadon & Jennings' First Big Deal
08/21/2025
Yeadon & Jennings' First Big Deal
Episode 3: Goose Creek Deal Welcome back to My First Million in Multifamily – My First Deal podcast, the series where we walk through our full-cycle deals: how we found them, raised the capital, closed, operated, and exited. We’ve covered our first couple of deals, and today we’re digging into Goose Creek—our first real “big boy” deal: 63 units outside of Summerville, South Carolina, near Charleston. The Flywheel Analogy You can imagine a 10-foot bronze flywheel. At first, it takes everything you’ve got to push it even an inch—it might even roll back on you. That’s what getting your first deal feels like. Even after that, the next revolutions take massive effort. But eventually, the momentum builds: brokers call you, investors reach out, opportunities start flowing. Goose Creek was one of those early pushes where the wheel still felt brutally heavy. Finding the Deal There are four main ways to find deals—we teach this in our Deal Room—and Goose Creek came from one of the oldest: word of mouth. At the time, Yeadon was in his BNI networking group (Business Networking International). Instead of talking about managing properties, he started telling everyone he was looking to buy apartments. That shift mattered. A commercial broker in the group—Hutch Hutchinson with Carolina One—mentioned he had a listing coming up. Hutch wasn’t a multifamily specialist, but he gave us the first look. As it turned out, that first look turned into a live deal: 63 units listed at $4M. Negotiations & Early Lessons We underwrote it, and at first it didn’t work with the super-conservative “65 cents on the dollar” model we were following after a conference. But after some back-and-forth, our LOI at $3.6M was accepted. Here’s where we hit our first big mistake: we told too many people. Another group swooped in with their own LOI, and we almost lost it. Lesson learned: don’t run your mouth while negotiating. Thankfully, our relationships saved the deal. Chad and Nick—loan sponsors we’d met at a conference—stepped in and backed us. The seller gave us a second chance, and we got it under contract at $3.6M. The Capital Raise Challenge Now came the scary part: raising $1.2M. Our first deal together (the 19-unit in Moncks Corner) only needed $250K, and Nick and Chad had raised that. For Goose Creek, they committed $100K but weren’t raising the rest. So we partnered with another guy who swore he could raise the million. Weeks ticked by… and three weeks before closing, he admitted he only had $200K. Cue panic. We had $300–400K soft-circled, but we were still $600–700K short. That’s when we decided: no one is coming to save us. We combed through every contact in our phones, texts, Facebook friends, emails—relentlessly calling, texting, pitching. It was brutal. Tons of “no’s,” lots of “maybe later,” but also enough “yeses.” Piece by piece, $25K and $50K checks started adding up. Then—seven days before closing, on Thanksgiving weekend—the lender cut our loan proceeds by $200K. Now we needed even more. Back to the phones. Somehow, we raised it. On December 6, 2019, we closed. Operations & Renovations We knew we couldn’t manage 63 units ourselves, so we brought in a local property management company experienced in repositioning. With their contractor connections, we launched a full renovation plan: All two-bedroom, one-bath units. Rents were $700–800; market was $1,000–1,100. $13–15K per unit in renovations plus exterior work. The CapEx was heavy, but over 18–20 months, we executed. By 2021, rents were up, units were stabilized, and the value had jumped. Refinance & Structure We refinanced into long-term agency debt: Freddie Mac loan 10-year term 5 years interest-only at 4.75% Returned nearly all investor capital Because we structured the deal with a 10% preferred return, investors got paid consistently but owned just 20% equity. We kept 80%. Cash flow to us was minimal during stabilization, but once refinanced, the heavy pref payments ended and the pressure eased. Exit & Why We Sold We held another year before selling. Here’s why: Bought at $57K/unit All-in around $76–80K/unit Sold at $105K/unit (~$6.8M total) We had created $1.9M in equity. At that point, rents were maxed out, value-add was complete, and holding meant more risk than reward—hurricanes, rising expenses, deferred maintenance. So we sold. After commissions and costs, it was still a massive liquidity event. Jennings and Yeadon each took home roughly $400–500K. Key Lessons from Goose Creek Don’t rely on one partner. Build a wide investor and loan-sponsor base. Capital raising is a skill. The only way to learn it is to do it—through rejection, persistence, and momentum. Know when to sell. Sometimes the best move isn’t “never sell,” but redeploying equity into better opportunities. Consistency beats talent. Showing up, making the calls, and pushing the flywheel is what separates those who succeed from those who fold. Goose Creek was our first real big deal. We found it, raised the money under pressure, executed renovations, refinanced, and exited successfully. It wasn’t smooth—it was scary, stressful, and nearly fell apart multiple times. But it proved we could do it. That’s why we’re sharing these stories: not the glamorized version, but the real trenches. Because the first few revolutions of the flywheel are the hardest—but once it’s moving, it changes everything. Stay tuned for the next episode, where we’ll keep unpacking the wins, losses, and lessons of our first full-cycle deals.
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Yeadon's First Deal
08/21/2025
Yeadon's First Deal
Episode 2: Yeadon’s First Deal Jennings: Hey, welcome back to the My First Deal podcast! Last week, Yeadon interviewed me about my first deal—a 12-unit apartment complex. Today, we’re flipping the script and talking about Yeadon’s first deal. Getting into that first deal is critical. There’s excitement, fear, and a ton of emotions that come with it. So, Yeadon, let’s start here: why did you want to do this? Yeadon: Leading up to my first deal, I was working full-time as a realtor. Real estate sales are purely transactional—no pension, no 401k, no safety net. I realized the only shot I had at retirement was to actually own rental properties. My plan was simple: someday I’d save up $50,000, buy an under-market rental house, do that a few times, build cash flow, and hopefully retire by 60. But I hadn’t done it yet—because life with three kids (eventually four) is expensive. There was never $50K left at the end of the year. New cars, roofs, transmissions, school stuff—you name it. Jennings: Right. I remember you saying, “I’ll do it in five years.” But honestly, most people never get there. As income rises, lifestyle expenses rise too. That’s why people get stuck. That’s why we started going to conferences. And when we went to that event in Ohio, I could see something click for you. Yeadon: Exactly. Up to that point, I thought buying apartments was out of reach. But at that conference, surrounded by people already doing deals, it suddenly became real. I remember seeing Tim Bratz on stage and thinking, What does he have that I don’t? He just focused, worked, and executed. I can do that too. I came home fired up. I told myself: Who do I need to meet? What relationships do I need to build? I’m going to make this happen. Jennings: I still remember you saying, “Dude, we can do this.” And that’s the shift—when you go from they can to I can. So you come home pumped. But what did you actually do next? Yeadon: I started leveraging my real estate network. I was in a BNI chapter—30 local businesspeople meeting weekly. Instead of pitching property management services, I started telling everyone: I’m looking to buy apartments. Do you know any owners or brokers? And it worked. A commercial contractor in the group introduced me to his friend Chris Wilson, who had an 18-unit apartment complex under contract. His family decided not to close, and he was willing to assign the contract. We met Chris at Starbucks, reviewed the deal, and I thought, I can’t believe I’m actually looking at an apartment contract that could be mine. Jennings: I remember that meeting. Instead of just writing him a check for the assignment, we offered Chris equity so he could stay in the deal. And he said yes. Yeadon: That’s right. Chris kept 5% ownership, and we got the contract. The property was 18 units in Moncks Corner, South Carolina—$740,000 purchase price, about $41K a door. Rents averaged under $500, but market rents were $800–900. It needed work: green shag carpet, outdated kitchens, old roofs. We budgeted about $10K per unit plus exterior work—roughly $260K in renovations. All-in, we were looking at a $1M project. Jennings: At the time, that was huge. We needed $250K cash for down payment and renovations—and a $750K loan. And neither of us had the capital or loan qualifications. Yeadon: Right. We had the deal under contract, but no money and no financing. That’s when we leaned on relationships from the conference. We partnered with Chad and Nick—guys who had capital, net worth, and lending ability. They liked us, liked the deal, and agreed to bring the $250K and sign on the loan. Jennings: That was massive. We structured it with a 10% preferred return for the investors, plus equity. Chad and Nick brought most of the capital and qualified for the loan, so they ended up with about 50%. You and I split the other 50%. Yeadon: Yep. We used a bridge loan through Lima One—two years, interest-only, 6%. Risky in hindsight, but it allowed us to finance both the purchase and the renovations. We closed in August 2019—just six months after that conference. Signing those papers felt like I had solved my retirement problem in one deal. Jennings: Talk about what happened after closing. Yeadon: We went to work. Renovated units, raised rents, replaced a roof, fixed septic and well systems. We even converted an unused garage into a 19th unit. Within 15 months, rent roll doubled—from $8,500 to over $15,000 a month. Then we refinanced with Freddie Mac into long-term, non-recourse debt: $1.15M loan proceeds 30-year amortization 10-year term 5 years interest-only at 4.75% That refinance returned all $250K to investors, ended the preferred return, and left everyone still owning equity. Jennings: That’s the dream: investors get all their money back, but they stay in the deal forever. Yeadon: Exactly. And today, rent roll is close to $20,000 a month. The property’s worth about $1.8–2M, with debt under $1M. In 20 years, it could be worth $4–5M, largely debt-free. That’s generational wealth from one deal. And the tax benefits—bonus depreciation at the time wiped out years of taxable income. That one deal literally caught me up for decades of not saving in a 401k. Jennings: And the cool part? That deal directly led to the next one. That’s why we’re doing this podcast—to tell the real stories of first deals. The obstacles, the doubts, the messy parts, and the wins. Because the first deal is the hardest, but it’s also the most life-changing. Thanks for joining us! Subscribe, share, and leave a review—it helps more people discover how commercial real estate can change their lives. See you next time.
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How it all started...Jennings' First Deal
08/21/2025
How it all started...Jennings' First Deal
Episode 1: Jennings' First Deal Intro The very first deal is always the toughest to close—but it’s also the deal that can change your life. That’s what this podcast is all about. We’re interviewing people on their very first deal: what it took to close it, the emotions before and after, the setbacks, the obstacles, and how it played out full cycle. Not just the glamor stories of closing a deal and running it into the ground—we’re talking full-cycle deals. We want to give you confidence, belief, and hope for closing your first deal. So, welcome to My First Deal podcast with my co-host, Yeadon Smith. Jennings Glad to be here, brother. I’m excited for the launch of this series. I remember back—what, seven years ago now?—we were doing property management. Then you said, “Yeadon, you should check out this course I bought on buying apartments.” Yeadon How long had you had that course at that time? Jennings About two years. I bought Michael Blank’s Ultimate Apartment Syndicator spreadsheet—just the analyzer for $150. I didn’t want to buy the full $1,100 course at first. But once I bought the spreadsheet, one of those ClickFunnel upsells popped up: “Apply what you’ve paid toward the full course.” I thought I was probably getting scammed, but I went for it anyway. Turned out to be a solid course, and that analyzer was well-built. It gave me confidence the rest of the content would be good too. Yeadon I remember thinking that was the dumbest thing ever. Like—you really bought a course online on how to become a gazillionaire? Jennings (laughs) Exactly. Back then, I had never bought anything online besides shoes from Amazon. Online courses were new to me. I thought, no way I’m falling for this. But I dove in, and pretty quickly realized: you can’t just learn from YouTube or a book. You need mentors and people ahead of you who can help you through the unseen obstacles, especially when you’re analyzing real deals. Yeadon So you’re going through the course, getting excited, but struggling to find anything that penciled. Jennings Right. I saw deals online, but none of them made sense. Then I found one listed at $750,000 in the upstate. To me, that was massive. I thought I’d need $200–300K down and a $500K loan. Way too big. My brain went straight to worst-case scenarios—bankruptcy, losing my house, my wife leaving me. So instead, I looked for something smaller. Yeadon And that’s when you found the 12-unit in Williamston, North Carolina? Jennings Yep. It was listed for $250,000—about $20K a door. Even back in 2019, that was cheap. I figured something had to be wrong. But I thought, I can handle this. If it goes sideways, I’ll figure it out. I called the broker. Turns out the seller was a wealthy guy with bigger properties elsewhere. This little 12-unit was neglected. The management company wasn’t giving it any attention. Rents were way below market—$350–$400. And the expenses were out of control: he was paying for water, gas for a giant water heater, and even double-paying for trash service. That’s when I realized: this is a value-add deal. Yeadon How did you figure out management? Small towns usually have limited options. Jennings I found a local realtor/property manager—an older lady named Georgie—who managed about 50 units in town. She knew the market and had a great reputation. She offered to manage it for 8%, way better than the 27% the big company was charging. That sealed it for me. I offered $240K and asked for seller financing. He agreed: 30% down, 70% financed over five years at 5%. Yeadon That’s a bold ask—what did it feel like? Jennings Honestly, I wasn’t nervous. I approached it from strength: I’m solving your problem. If you’d run this properly, it would be bank-financeable. Since it’s not, here’s how we can structure it. He agreed without much pushback. Yeadon So now you needed $75K for the down payment. Jennings Right. I pitched a couple investors, but they didn’t want to bet on someone with no multifamily track record. Finally, I went to the “Bank of Dad.” He grilled me hard—especially on why I wanted 60/40 in my favor when he was bringing all the money. But I told him: Money is a commodity. I’ve got the deal. If you don’t do it, someone else will. He agreed, and we closed. Operations We fired the expensive manager, switched to Georgie, cut the trash bill, implemented a utility bill-back, and stabilized the property. Within months, it was cash flowing. Eighteen months later, I sold it for $415K. Bought at $240K, sold at $415K. After paying my dad his $90K back plus $70K profit, I still cleared $105K tax-free thanks to depreciation. Yeadon That’s life-changing money. Jennings Exactly. One deal, one time, can change your life forever. That first six-figure check gave me the confidence and the fuel to go full-time. Since then, we’ve built a $60M portfolio. But it all started with that first deal—and pushing through the nos, the fears, the awkward conversations, and the “valley of embarrassment.” Outro That’s why we started this podcast: to share the real stories behind people’s first deals. The obstacles, the lessons, and the wins. Because the first deal is not only the hardest—it’s also the most life-changing. If you’re inspired, connect with us at . Check out Unlock Your Life for more content, and don’t forget to like, subscribe, and rate the show. Until next time...
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