I've Owned Apartments Since 1990. Here's What 3 Decades In The Industry Teaches You.

I've Owned Apartments Since 1990. Here's What 3 Decades In The Industry Teaches You.

John Gillespie has been in the apartment business since 1990. He's the president of WAK Management Company, which owns and operates 4,500 units across 22 properties in North Texas and greater Nashville - and they still own the very first property they ever bought. No outside investors. No syndication pressure. Just 35 years of quiet, unglamorous work.John, a guy who's been through the RTC crisis of the late 80s, the post-9/11 insurance collapse, the 2008 recession, and the 2022–2025 multifamily cycle - is still standing, still walking properties at 6am, still having lunch with his 90-year-old mentor once a month.We get into:- Why they've never taken outside investors, and what that's actually meant over 35 years- The post-9/11 moment their entire insurance portfolio was about to lapse and nobody would write a policy- Buying Delray Village for $8M (appraised at $16M) and immediately realizing they'd made a mistake- What 30% resident turnover looks like when your competitors are at 80%- Why John still walks properties at 6am even with 130 staff and an executive team- The "limit one" candy dish story - and what it tells you about an operator- The three P's that have kept Wack at the top of the market for three decades- Where the DFW multifamily market is actually heading and what lenders are finally starting to accept- What 46 years of marriage and 27 years running the same company have in commonCHAPTERS00:00 — Intro & Mike Tyson's theory on business01:55 — John introduces Wack Management: 4,500 units, since 199002:45 — How John got pulled into real estate (it was an accident)04:10 — Buying apartments during the RTC crisis — worse than 200807:15 — The first property: 17 banks, closed December 31st09:00 — Growing up in Bishop Arts before it was Bishop Arts10:00 — Dick Aarons calls John to Dallas — the deal that started 27 years13:00 — Learning to manage people, not just properties16:30 — Why John still walks properties himself20:30 — The Saturday leasing agent conversations that taught him more than anything25:00 — Building an executive team and letting go of day-to-day28:00 — Why no outside investors has been their greatest advantage29:30 — Managing people: communication over performance management34:00 — Residents who've been there 25+ years — and the retired postal worker who barbecues with John37:30 — The three P's: People, Places, Profit (in that order)41:30 — What a "limit one" candy dish tells you about an operator45:00 — How to read a property in the first 60 seconds46:00 — Where the DFW market is now and when lenders will blink53:00 — Why 70–80% of listings in DFW didn't close last year55:00 — The 9/11 insurance crisis — the closest they ever came to losing everything62:00 — Delray Village: bought for $8M, regretted it immediately67:00 — Succession planning and working fewer hours at 27 years inGUESTJohn Gillespie - WAK Management Company🎧 New episodes weekly. Subscribe so you don't miss the next one.📲 More on Instagram: @justsayanpodcast

He Was Told He'd Never Amount to Anything, Bought a Private Jet, and Built an Apartment Empire

Brad Sumrock was 14 years into corporate America with an MBA, an engineering degree, and a boss who told him he'd never amount to anything because he took his lunch break and used his paid vacation. He got fired six months after closing the second-biggest deal in company history. Today he owns over 11,000 apartment units, has bought (and sold) his own $7 million private jet, and hasn't paid federal tax in 6 of the last 8 years - all of it legally.This one goes deep. Brad shares the four kinds of millionaire (and the one he actually wanted to become, until his CPA showed him a better path), how he hit a hockey-stick in 2018 that took him from a $1M tax bill to zero, and what 24 years of cycles taught him about where multifamily is heading in 2026. But the back half of this conversation is where it really opens up — Brad gets honest about being functionally depressed in 2023, the divorce, the first investor loss in 24 years, food addiction, and what success actually looked like once the achievement chase stopped working.We get into:- The boss who said he'd never amount to anything (and the irony of how that ended)- The four types of millionaires, and why "paying $1M in tax" was Brad's original goal- How Brad went from owing a million in taxes to paying zero — legally- Why the multifamily cycle of 2023–2025 was the worst Brad's seen in 24 years- The 2026 outlook: "it's time to have your foot on the gas"- Buying the jet, naming it Sumrock Air, and what it actually felt like- Jesse Itzler, the donut hack at conferences, and how he sold a jet company to Warren Buffett with no jets- The 7-day keto fast, the food pyramid lie, and what 36 pounds of weight loss in 92 days actually took- What Brad felt when his mom died, the divorce, and the year he describes as "dead inside"What's something you were told you couldn't do, and then did anyway? Drop it in the comments.CHAPTERS00:00 — Intro01:00 — From Pittsburgh engineer to apartment investor04:30 — The boss who said he'd never amount to anything08:00 — Getting fired six months after the biggest deal12:00 — Why he's spent $2M on mentors over 25 years18:00 — The hockey-stick years (2018–2022)25:00 — The four types of millionaires30:00 — How he stopped paying federal tax (legally)38:00 — Buying Sumrock Air, the $7M private jet45:00 — Surviving the worst multifamily cycle in 24 years55:00 — The 7-day keto fast and the food pyramid flip68:00 — Jesse Itzler, the donut hack, and selling no-jets to Warren Buffett80:00 — What "dead inside" actually felt like90:00 — Mom dying, divorce, and learning to feel pain98:00 — Where multifamily is heading in 2026GUESTBrad Sumrock - Sumrock Apartment MentorInstagram: bradsumrokhttps://bradsumrok.com 🎧 New episodes bi-weekly. Subscribe so you don't miss the next one.📲 More on Instagram: @justsayanpodcast #multifamilyrealestate #realestateinvesting #entrepreneurship #apartmentinvesting #podcast #justsayanpodcast #realestatepodcast

He Sold Pokemon Cards to China, Ran 35 Miles for Fun, and Built a Multifamily Empire

Dustin Miles ran a candy business out of his backpack at eight years old. By college, he was shipping Pokemon cards to buyers in China and New Zealand to pay for ramen. By his thirties, he was an engineer at Lockheed Martin. Now he owns multifamily real estate across Texas and the Midwest, runs Momentum Multifamily with his partner Hayden, and recently ran 35 miles from Fort Worth to downtown Dallas just to see if he could. This one's about the long version of "success" - the unsexy parts, the misfires (he tried forex, MLM, and lost money to a coach who ghosted him), and the mindset that takes a kid hustling Laffy Taffy to a $1.6M real estate raise. None of it was a straight line. We get into: - The Pokemon-to-China side hustle that funded a ramen-noodle college life - Watching a friend's family own a skyscraper and deciding "why not me" - The first $1.6M raise and how he stacked the cards in his favor — Where multifamily actually is right now — concessions, fraud, leasing season - The "build the airplane as you're falling out of the sky" Covid raise - What he tells his 14-year-old son Henry about staying coachable What's the longest you've ever run, walked, or pushed yourself for no good reason? Drop it in the comments. CHAPTERS 00:00 - Intro 00:35 - The Candy Man at 8, Pokemon dealer at 20 04:10 - Engineering, Lockheed Martin, and picking the hardest path 06:30 - Running 35 miles from Fort Worth to Dallas 13:20 - The skyscraper that changed everything 17:00 — Why the four-minute mile mindset matters 19:00 - Taking action before you're ready 25:20 - Hiring coaches, getting ghosted, and what actually works 29:00 - The state of multifamily right now 32:30 - The wildest concession he's ever seen 34:30 - What's kept him in the game through this cycle 40:30 - Covid, preferred equity, and pivoting under pressure 42:30 - Advice for his son Henry GUEST Dustin Miles - Momentum Multifamily 🎧 New episodes on the 1st and 15th. Subscribe so you don't miss the next one. 📲 More on Instagram: @justsayanpodcast

Wire Fraud at Closing, a Seller Who Died Before Signing, and the Truth About the Housing Market

Veronica Warwick started her real estate career right as her husband was deployed overseas - no support system, a brand new license, and two kids still in school. She figured it out.In this episode, Veronica and her partner Jeanette Feliciano pull back the curtain on what real estate actually looks like - the stuff nobody tells you. A seller who passed away an hour before his signing. A young couple who wire-transferred their closing funds to a scammer. And a market that's making it harder every year for first-time buyers to get in.They also get into how they're using AI to analyze client calls in real time, why the highest offer almost never wins, and what they tell every new agent who's about to quit.If you're thinking about buying, selling, or getting into real estate yourself - this one's worth your time.Veronica's IG: https://www.instagram.com/warwickrealtygroup/Veronica's Website: https://www.warwickrealtygroup.com

He Slept 4 Hours a Night, Got Paid in Guitars, and Built an Agency That's Lasted 20+ Years

On this episode of the JustSayan Podcast, we're joined by Jon Simpson, founder of Criterion.B, a marketing agency focused on Multi-Family properties, and Be Swity, a SAAS for multifamily marketing. He shares stories of how he first got started in the industry 20+ years ago an how his companies are still flourishing today.