Tyler Chesser's Playbook: Achieving $2.1M Exits and $150M Targets in a Volatile Market

27/10/2025 45 min Episodio 20
Tyler Chesser's Playbook: Achieving $2.1M Exits and $150M Targets in a Volatile Market

Listen "Tyler Chesser's Playbook: Achieving $2.1M Exits and $150M Targets in a Volatile Market"

Episode Synopsis


In this episode, Brad chats with Tyler Chesser, co-founder and managing partner of CF Capital. Tyler leveraged his background as a top multifamily broker to scale his portfolio and develop CF Capital into a respected partner for investors. He shares his philosophy of constant improvement and details his journey from corporate America to real estate agent in 2013 and how he built CF Capital, which today owns and operates approximately a $200 million multifamily portfolio.
🔑 Key Topics Covered:

How reading books like Rich Dad Poor Dad and Think and Grow Rich was the catalyst for changing his financial mindset.
The difference between a broker's role and an investor's role: "when the deal closes, that's when the real work begins".
Lessons from his first deal: an 8-unit property bought for $360,000 in 2016 that became "severely mismanaged" and dropped to 50% occupancy.
The mistake of self-managing the first deal and the need for a professional team from the beginning.
The home run deal: acquiring a 36-unit property from an estate sale for $1.1 million in 2019.
How having a construction-focused partner allowed them to quickly turn ten completely vacant units in a matter of months.
Using a cash-out refinance for an "infinite return" before selling the 36-unit property for $2.1 million in 2021.
The power of "just one more call" to secure an off-market deal.
CF capital's current focus on syndication with private and institutional capital.
The firm's next goal: targeting 150 million in acquisitions over the next twelve months.

💬 Memorable Quotes:

"As an investor, when the deal closes, that's when the real work begins." — Tyler Chesser
"I would attribute, I'd say ninety percent of my success to just learning and continuing to commit to constant and never ending improvement." — Tyler Chesser
"The next twelve months, our focus even in a, you know, somewhat challenging environment... is one hundred and fifty million in acquisitions in our markets." — Tyler Chesser

🔗 Connect with Tyler Chesser:
Website: https://www.cfcapllc.com/
🎙️ Connect with Host Brad Weaver:
LinkedIn: https://www.linkedin.com/in/bradweaver 

More episodes of the podcast First, Worst, Best, & Next