036. Multifamily Brokerage to Syndication with Tyler Chesser

Multifamily Brokerage to Syndication with Tyler Chesser

Tyler Chesser, CCIM, is an experienced multifamily real estate investor, in an active and passive capacity, and has witnessed firsthand the successes and failures of building a real estate portfolio. Tyler is the Founder of The Chesser Companies where he works with leaders, entrepreneurs and real estate investor clients as a peak performance coach and world class consultant; he’s a high performance coach, additionally providing group coaching services through Elevate High Performance Coaching Academy, he’s also the Co-Founder of CF Capital, a real estate private equity firm, which focuses on acquiring and repositioning multifamily assets in the Southeast United States and provides institutional-quality services to its residents and outsized returns to its investment partners.

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322. When to Quit Your W2 for Real Estate | Office Hours
322. When to Quit Your W2 for Real Estate | Office Hours

In this episode of the Commercial Real Estate Investor Podcast, we’re tackling one of the biggest questions I get: When should you quit your W2 to go full-time in real estate?

It’s a conversation packed with lessons from the front lines—because let’s face it, syndication sounds sexy… until you realize those fees don’t cover the mortgage, much less your rent. I’ll walk you through how I approached this decision, why I’m only now closing my first solo deal after a decade in CRE, and what most gurus won’t tell you about raising capital and replacing your paycheck.

321. Why He Chose Flex Space for His First Development
321. Why He Chose Flex Space for His First Development

Alec McElhinny is an industrial owner, operator, and developer based in Texas. He was one of the earliest members of my CRE Accelerator mastermind and today, we're diving into why he decided that developing flex space from the ground up was the right move for him.

320. Riding Out a Recession in Commercial Real Estate
320. Riding Out a Recession in Commercial Real Estate

In this episode of the Commercial Real Estate Investor Podcast, I’m sharing some hard-earned insights on navigating commercial real estate in uncertain times. Whether we’re heading into a full-blown recession or just riding out economic headwinds, one thing’s clear: success in CRE isn’t about predicting the market—it’s about how you position yourself when things get tough.

This past week’s been a whirlwind—jumping straight out of meetings, dealing with a contractor dispute that ballooned to a $100,000 overage on a $166,000 job, and preparing for our upcoming CRE Accelerator Mastermind event right here in Nashville. We’re talking full-scale underwriting workshops, deal pitches over cocktails, and a deep dive into live property analysis with the mastermind community.

319. The Power of Creative Capital in Commercial Real Estate
319. The Power of Creative Capital in Commercial Real Estate

In this episode of the Commercial Real Estate Investor Podcast, we’re exploring the art of Creative Capital—how to leverage strategic funding options and partnerships to accelerate your real estate journey.

I’m breaking down my proven methods for building wealth in commercial real estate without needing millions of dollars in the bank. You’ll learn why Creative Capital stacking is a game-changer, how to leverage 100% seller financing, and how I’m constantly connecting with high-net-worth investors and partners to scale faster. I’ll also share insights from the CRE Accelerator Mastermind, where I help investors navigate complex deals and build successful portfolios.

318. Off-Market Mastery: How to Find Unicorn Deals in Any Market
318. Off-Market Mastery: How to Find Unicorn Deals in Any Market

The best deals never hit the market—and the best brokers know how to uncover them. In this no-fluff session, Chad, Jesse, and Adam unpack the exact tactics they’ve used to uncover high-margin, off-market opportunities. From building referral pipelines to leveraging tech and data to think like an investor, you’ll learn how to source smarter, move quicker, and build a reputation as the broker who always brings the deal.

317. 12 Lessons from 12 Years in Commercial Real Estate | Office Hours
317. 12 Lessons from 12 Years in Commercial Real Estate | Office Hours

In this episode of the Commercial Real Estate Investor Podcast, we’re diving into the 12 most impactful lessons I've learned from over a decade in the world of commercial real estate. These aren't just abstract theories – they’re hard-earned insights from my own journey, each shaped by deals closed, mistakes made, and relationships built.



316. Mastering the Art of the Deal Pitch | Investors Round Table
316. Mastering the Art of the Deal Pitch | Investors Round Table

In this episode of the Investors Round Table, we'll explore one of the most important — and overlooked — skills for commercial real estate investors: crafting and delivering compelling deal pitches. Logan, Matt, and I will break down what makes a deal pitch magnetic, how to think like a marketer when presenting investment opportunities, and the key mistakes to avoid when selling to brokers, partners, and investors. We'll share real-world examples, give actionable advice on improving your pitch game, and discuss how to tailor your messaging to different audiences. Whether you're raising capital, wholesaling a property, or trying to win broker support, mastering the pitch can be the difference between deal flow and deal famine.

315. Interviewing Contractors for Your Projects | Office Hours
315. Interviewing Contractors for Your Projects | Office Hours

In this episode of the Commercial Real Estate Investor Podcast, we're diving deep into the art of finding and vetting contractors for your next big project.

I'm breaking down my proven strategy for connecting with the right contractors—whether you're developing a restaurant, medical office, or self-storage facility. We'll talk about why not all contractors are created equal, and how to find the perfect match for your specific project type.

314. The 3 Fastest Ways to Get Your First Commercial Listing
314. The 3 Fastest Ways to Get Your First Commercial Listing

In this episode, we break down the top three fastest ways to land your first commercial real estate listing—whether you’re transitioning from residential, starting out in CRE, or hitting the reset button. Join Chad (Industrial), Jesse (Office), and Adam (Retail) as they each share practical, sector-specific strategies that helped them build early traction and credibility.

313. Is Commercial Real Estate A Sensible Investment Today? | Office Hours
313. Is Commercial Real Estate A Sensible Investment Today? | Office Hours

This week on the Commercial Real Estate Investor Podcast, I’m going live for Office Hours and tackling the big question—does commercial real estate still make sense in today’s market?

Between global turmoil, inflation pressure, and rising construction costs, a lot of investors are sitting on the sidelines. But if you know how to underwrite, stress test, and play the long game, CRE still offers massive opportunity. I’m sharing how I’m navigating the current market, what returns are actually worth chasing, and why timing the market is a losing game.