First, Worst, Best, & Next

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

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/ [https://www.cfcapllc.com/] 🎙️ Connect with Host Brad Weaver: LinkedIn: https://www.linkedin.com/in/bradweaver [https://www.linkedin.com/in/bradweaver]

John Casmon on 'Failing Forward' and the Power of Midwest Real Estate

In this episode, Brad chats with John Casmon, former marketing executive, founder and managing partner of Casmon Capital Group , and host of the top-rated Multifamily Insights podcast. John shares his journey from corporate America—where he survived two company bankruptcies that spurred his need for a "Plan B" —to a full-time real estate investor with over $140 million in multifamily investments. He also recounts the pivotal moments that shaped his investing philosophy, from his first accidental home run deal to the painful lessons of his worst investment.   🔑 Key Topics Covered: * How going through two corporate bankruptcies (at General Motors and an agency) was terrifying yet eye-opening, leading him to realize he couldn't rely just on savings and needed to accelerate his investing through apartment syndications. * The strategy behind his "phenomenal" first deal: a two-unit house-hack in Chicago’s North Center neighborhood. * The game-changing move of using an FHA loan (only 3.5% down) and reinvesting his savings into renovations, leading to a refinance a year later that provided a line of credit for over $100,000. * The discovery that North Center was the only Chicago neighborhood that did not lose any value during the 2007-2010 economic downturn. * The $150,000 increase in property value on his first deal—more than he made in a year—that cemented his confidence in real estate. * The "worst deal" that led to a six-figure loss : a house-flipping partnership where he ignored red flags like a razor-thin 88–89% cost relative to the After Repair Value (ARV). * The emotional cost of the bad deal, which "shattered" his confidence and caused stress in his personal life, but taught him the value of "failing forward". * The commitment to his private lender, where he chose to lose more money to finish the project rather than leave them "high and dry". * The shift back to multifamily investing, where he joined a general partnership and raised just under half a million dollars on his first 192-unit deal. * The "best deal": a townhome community in Florence, Kentucky, purchased for $8 million and likely to sell in the $15 to $16 million range. * Why the Midwest is his preferred market for investing, noting its stability, diversified industries (logistics, hospitality, education), and sustainable growth. 💬 Memorable Quotes: * "Man, I can't rely just on what I've saved to invest in real estate. I gotta find a way to accelerate this." — John Casmon * "That deal really was the catapult to set us up and get us going." — John Casmon * "I literally took on an outsized portion of risk for... And we only focused on what we would split from a profit standpoint, but not the downside component." — John Casmon * "You've already paid for the education. Take the lesson and you're gonna be a better investor moving forward." — John Casmon * "The market is really important. And to be clear, I don't just mean the city or the MSA. I mean, the submarket." — John Casmon 🔗 Connect with John Casmon: * Free Guide: Seven Questions You Must Ask Before Investing in Apartments: https://casmoncapital.com/7questions/ [https://casmoncapital.com/7questions/] * Multifamily Insights Podcast: https://casmoncapital.com/podcast/ [https://casmoncapital.com/podcast/] 🎙️ Connect with Host Brad Weaver: * https://www.linkedin.com/in/bradweaver [https://www.linkedin.com/in/bradweaver]

John Wijtenburg on Transforming a $100M Resort and the CRE Growth Operating System

In this episode, Brad chats with John Wijtenburg, founder of LXK Group, an expert in commercial real estate operations and systems, who helps investors and operators scale their portfolios while maintaining their core values. John shares his journey from an economist at Fannie Mae and an apartment broker to a successful hotel operator and asset manager, and discusses his framework for growth in the CRE space. 🔑 Key Topics Covered: * John's career path: from institutional roles to building an eight-hotel extended stay portfolio and now consulting on luxury and boutique properties. * The persistence of the same operational challenges in portfolios ranging from $5 million to $1 billion. * How John built systems to scale businesses beyond the "three to five property bottleneck". * The importance of vision and execution in the $100 million Fort Lauderdale resort renovation. * Why hospitality is an "operating business with a real estate component," requiring constant renovation due to nightly leasing and wear and tear. * Creative value-add strategies, including blowing out a light well and converting a roof into a skylight to enhance the guest experience. * The concept of a "generational hold" and how it fundamentally changes how risk and investment decisions are underwritten. * Why full-service hotels take longer to stabilize (around four years) compared to limited-service properties. * Lessons from a struggling deal: accepting a loss to avoid "sunk cost bias" and the power of over-communicating with LPs. * The "home run" deal that became a "machine for printing talent" by developing a strong internal system and culture. * The "boring brilliance" of having a process for creating and improving processes. * Introducing the Commercial Real Estate Growth Operating System (CRE Growth Operating System), designed to help operators move past their personal bottleneck.  * Engaging frontline talent: The key isn't just benefits, but aligning daily actions with a clear purpose and vision. 💬 Memorable Quotes: * "I've discovered that the same problems persist across different asset classes, across different portfolio sizes, whether it's $5 million, $50 million, a billion-dollar portfolio." — John Wijtenburg * "I always describe it [hotel business] as an operating business with a real estate component, whereas others are a real estate business with an operating component." — John Wijtenburg * "You can't have this sunk cost bias that's going to just destroy your future and eat up all the opportunity you have ahead of you..." — John Wijtenburg * "When you set up your communication infrastructure the right way, you end up building more trust from a bad deal than you do from a good deal." — John Wijtenburg * "It's like boring brilliance to be able to just like build a good process for optimizing processes." — John Wijtenburg 🔗 Connect with John Wijtenburg: * 💼 LinkedIn: https://www.linkedin.com/in/johnwijtenburg [https://www.linkedin.com/in/johnwijtenburg] * 🌐 Website: https://lxkgroup.com [https://lxkgroup.com] 🎙️ Connect with Host Brad Weaver: * 💼 LinkedIn: https://www.linkedin.com/in/bradweaver [https://www.linkedin.com/in/bradweaver]

John Todderud's Journey from Tech to Multifamily Syndication

In this episode, Brad chats with John Todderud, the founder of Cardinal Oak Investments and a former tech professional who transitioned into multifamily real estate. John shares his journey from buying small, rural properties to scaling a full-fledged syndication business. He opens up about the biggest lessons he learned from his "worst" and "best" deals, including the pitfalls of underestimating deferred maintenance and the unexpected rewards of a long-term hold in a stable market. John also discusses his shift from individual ownership to syndication, highlighting the value of building relationships and leveraging investor capital to acquire larger assets. Key Topics Covered: * John's path from a tech career to full-time real estate investor. * The evolution of Cardinal Oak Investments from a personal vehicle to a syndication business. * The importance of starting small and learning from mistakes, as with his first three-unit deal. * The harsh lesson of underestimating deferred maintenance on a big value-add project. * Why a "slow and steady" deal in a recession-resistant market turned into a "home run". * The key differences between a joint venture and a syndication, and why he chose the latter. * The current market and why patience is crucial for finding the right deals. * The value of building trust and relationships with investors as a syndicator. 💬 Memorable Quotes: * “I wanted a property that I could… learn on, essentially to make my mistakes, my small mistakes.” — John Todderud * “It's not like you fix the roof and suddenly you can get higher rents... a lot of these things don't translate directly into income, but they do mean a buyer... has fewer things to choke on.” — John Todderud * “I never would have expected it... just a huge pleasant surprise.” — John Todderud on his "home run" deal 🔗 Connect with John Todderud: * Website: learnaboutapartments.com [https://cardinaloak.com/quiz] * Email: john@cardinaloak.com [John@Cardinaloak.com] 🎙️ Connect with Host Brad Weaver: * LinkedIn: https://www.linkedin.com/in/bradweaver [https://www.linkedin.com/in/bradweaver]

Beyond the First Deal: Scaling a Real Estate Portfolio with Ian Cruz

In this episode, Brad chats with Ian Cruz, a former CPA and boxing coach who has successfully transitioned into multifamily real estate. Ian shares his journey from his roots in big four public accounting to becoming a value-add multifamily investor focused on the Cincinnati, Ohio market. He discusses the importance of building a strong local team when investing out of state, the value of in-person networking, and how a disciplined approach—honed from his years as a boxer—helps him navigate the inevitable challenges of real estate.   🔑 Key Topics Covered: * How the discipline from boxing translated into success in real estate. * The importance of building a local "boots on the ground" team for out-of-state investing. * Why finding a local general partner (GP) with a property management and renovation company was a massive win. * The benefit of a previous failed deal in building trust with investors. * How to create "certainty of close" to win deals against higher bidders. * The strategic advantage of buying properties that have fallen out of contract. * Lessons learned from a "worst" deal, including the challenges of dealing with older assets and uncooperative sellers. * How a successful first deal with a partner led to the acquisition of a much larger, 70-unit portfolio. * The competitive advantage of operating in the "sub-institutional" space. * How Ian is building a community of over 200 investors interested in the Cincinnati market. 💬 Memorable Quotes: * "If you're raising capital when you have the deal, it's too late ". * "You almost have to shake hands with the city you're investing in too ".   🔗 Connect with Ian Cruz: 📸 Instagram: https://www.instagram.com/cincycashflow/ [https://www.instagram.com/cincycashflow/] 💼 LinkedIn: https://www.linkedin.com/in/cbcruz/ [https://www.linkedin.com/in/cbcruz/]   🎙️ Connect with Host Brad Weaver: 💼 LinkedIn: https://www.linkedin.com/in/bradweaver [https://www.linkedin.com/in/bradweaver]