EP443: From Broker to $200M Syndicator: Tyler Chesser on Playing the Long Game in Multifamily

What separates transactional hustlers from industry titans? Discover the secrets of how Tyler Chesser—co-founder of CF Capital pulls back the curtain on building a $200M multifamily portfolio by mastering transformational relationships and long-term strategy. From his early days as “the apartment guy” to navigating institutional capital and market volatility, Tyler shares hard-earned insights on partnerships, capital raising in a tough economy, and why patience, prudence, and relationships still rule the game. If you're an investor or entrepreneur serious about scaling with substance, this is one conversation you can't afford to miss. 5 Key takeaways to learn from this episode1. Transformational Relationships Trump Transactional OnesTyler emphasizes the long-term power of building genuine, value-driven relationships rather than chasing short-term wins. This approach not only fuels repeat investments but also opens unexpected doors—like a small early lease turning into hundreds of thousands in future investments.2. Conservative Underwriting and Patience Pay OffUnlike many operators who rushed into deals during the market high of 2021-2022, Tyler’s team at CF Capital exercised caution. Their selective acquisitions, based on below-replacement-cost assets and long-term fundamentals, allowed them to weather market headwinds without distress.3. Partnerships Enable Exponential GrowthTyler credits much of CF Capital’s success to having a strong, complementary partnership from day one. Dividing responsibilities between strategic capital raising and operational execution helped them scale faster and smarter without overwhelming any one individual.4. Capital Raising is Three to Five Times Harder in Today’s MarketRaising capital in 2024 is significantly more challenging than during the boom years. Tyler notes a steep increase in investor caution, requiring more effort, conversations, and relationship nurturing to secure commitments—even for high-quality deals.5. Thought Leadership and Investor Experience Drive GrowthTyler built credibility through his top 200 podcast, speaking engagements, and consistent investor communication. Combined with excellent execution and referrals, this multifaceted approach has fueled CF Capital’s investor base—while his shift to leveraging others’ platforms continues expanding their reach.About Tim MaiTim Mai is a real estate investor, fund manager, mentor, and founder of HERO Mastermind for REI coaches.He has helped many real estate investors and coaches become millionaires. Tim continues to help busy professionals earn income and build wealth through passive investing.He is also a creative marketer and promoter with incredible knowledge and experience, which he freely shares. He has lifted himself from the aftermath of war, achieving technical expertise in computers, followed by investment success in real estate, management skills, and a lofty position among real estate educators and internet marketers.Tim is an industry leader who has acquired and exited well over $50 million worth of real estate and is currently an investor in over 2700 units of multifamily apartments.Connect with TimWebsite: Capital Raising PartyFacebook: Tim Mai | Capital Raising Nation Instagram: @timmaicomTwitter: @timmaiLinkedIn: Tim MaiYouTube: Tim Mai