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/
🎙️ Connect with Host Brad Weaver:
LinkedIn: 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/
Multifamily Insights Podcast: https://casmoncapital.com/podcast/
🎙️ Connect with Host Brad Weaver:
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
🌐 Website: https://lxkgroup.com
🎙️ Connect with Host Brad Weaver:
💼 LinkedIn: 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
Email: john@cardinaloak.com
🎙️ Connect with Host Brad Weaver:
LinkedIn: 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/
💼 LinkedIn: https://www.linkedin.com/in/cbcruz/
 
🎙️ Connect with Host Brad Weaver:
💼 LinkedIn: https://www.linkedin.com/in/bradweaver

Bruce Fraser on Distressed Multifamily and Macro Investing

In this episode, Brad chats with Bruce Fraser, a Forbes Real Estate Council Member and Managing Partner at Elkhorn Capital Partners. Bruce shares his unique journey from running a successful hedge fund for over a decade to becoming a multifamily investor. He explains how his background in macroeconomics led him to focus on hard assets, specifically distressed multifamily properties, as a hedge against inflation. Bruce also provides incredible insight into why his firm is a go-to buyer for brokers and lenders, and why trust and discipline are paramount to success in real estate.
 
🔑 Key Topics Covered:
Why Bruce pivoted from managing a hedge fund to investing in real estate.
Elkhorn Capital's focus on distressed multifamily turnarounds and why they don't invest in Dallas.
The "first deal" that yielded a 50% return in just 14 months and the lessons learned from the buyer who overpaid.
The challenges of managing a "worst deal" with drug dealers and the importance of having a proactive plan.
How being vertically integrated and financially incentivizing staff leads to stunning results.
The "home run" deal that was a Freddie Mac foreclosure and the "good problems" of a successful recapitalization.
Why reputation and certainty of close are invaluable with brokers and lenders.
Bruce's outlook on inflation and why he continues to acquire hard assets.
 
 
💬 Memorable Quotes:
"You make the money on the buy... you just have to be disciplined." — Bruce Fraser
“You can't get emotional about winning a deal and overpaying. Then you're kind of stuck with an albatross.” — Bruce Fraser
"It's about bottom line... we're not just about expense minimization." — Bruce Fraser
"It's just numbers... All you have to do is pay attention to it." — Bruce Fraser
 
🔗 Connect with Bruce Fraser:
💼 LinkedIn: https://www.linkedin.com/in/bruce-fraser-8806295/
🌐 Website: https://elkhornpartners.com/
 
 
🎙️ Connect with Host Brad Weaver:
💼 LinkedIn: https://www.linkedin.com/in/bradweaver

From Cybersecurity to $217M in Real Estate: Tenny Tolafari's Journey

In this episode, Brad connects with Tenny Tolafari, a cybersecurity professional turned real estate mogul and co-founder of Xsite Capital. Tenny shares his incredible journey from working 60-hour weeks in corporate America to building and managing a $217 million real estate portfolio. He recounts the full-circle story of a cold call that led to a valuable connection, the challenges of landing their first deal, and the importance of having the right team in place. Tenny also reveals how Xsite Capital navigated the complexities of a $49.1 million transaction and the valuable lessons learned from it.
 
🔑 Key Topics Covered:
Tenny's transition from the corporate world to full-time real estate.
The "secret sauce" of Xsite Capital's success: putting the right people in the right seats.
The persistence required to build relationships with key players in the industry, like brokers.
The story of their first deal, a $12.55 million acquisition that turned into a $5.3 million profit in 21 months.
The unexpected fire that broke out just two weeks after closing their first property.
The biggest challenge in today's market: raising capital for large transactions.
Why the real goal isn't just to achieve something, but to become the person capable of achieving it.
Xsite Africa's vision of creating a bidirectional investment bridge between Africa and the US.
💬 Memorable Quotes:
"Relationship is a key important component... You have to think about this long term." — Tenny Tolafari
"That's why we created Exsite [Capital] so that you don't have to worry about the challenge." — Tenny Tolafari
"The essence of a goal is not for you to hit the goal, but for you to become the person that's capable of hitting that goal." — Tenny Tolafari
🔗 Connect with Tenny Tolafari:
📸 Instagram: https://www.instagram.com/ttolofari/
💼 LinkedIn: https://www.linkedin.com/in/tenny-tolofari
🌐 Website: https://www.xsitecapital.com/tenny
🎙️ Connect with Host Brad Weaver:
💼 LinkedIn: https://www.linkedin.com/in/bradweaver

Lessons from a $650M Portfolio: Insights from Real Estate Veteran Dusty Eddy

In this episode, Brad chats with Dusty Eddy, founder of Eddy Capital Group, and a veteran real estate investor with over 23 years of experience. Dusty, who has led over $650 million in multifamily investments and completed 15 full-cycle deals with impressive returns, shares his journey from an institutional background to building his own firm. He discusses the importance of local expertise in avoiding bad deals and leveraging relationships. Dusty also opens up about his best and worst deals, revealing how even a "worst" deal can yield fantastic returns and what he learned from each one.
🔑 Key Topics Covered:
Dusty's journey from an analyst at a prior firm to a solo real estate investor
The importance of having "boots on the ground" and deep local market knowledge
The challenges and advantages of buying from "mom and pop" owners
The story of a "worst" deal that still generated a 26% IRR and 1.6x equity multiple
The flawless execution of a "best" deal that delivered an 80% IRR and 4.4x equity multiple at the peak of the market
The value of pushing rents and increasing NOI to create a floor for property valuation
The long-term strategy of focusing on A and B locations with a value-add approach
The benefits of adding creative amenities like private patios and outdoor spaces
What's next for Eddy Capital Group and the importance of building a dedicated team
💬 Memorable Quotes:
"Being local helps you avoid more bad deals than necessarily get good deals." — Dusty Eddy
"Sometimes you literally get a rent roll on a napkin... I'm exaggerating, but not very much to be honest." — Dusty Eddy
"The positive and the negative is that investors start to think that's normal and that's like, that's right, you're gonna do that every time, right?" — Dusty Eddy
🔗 Connect with Dusty Eddy:
💼 LinkedIn: https://www.linkedin.com/in/dusty-eddy-mba-5630b53
🌐 Website: https://eddycapgrp.com/
 
🎙️ Connect with Host Brad Weaver:
💼 LinkedIn: https://www.linkedin.com/in/bradweaver

From Start-Up to $1 Billion Portfolio: Lessons in Commercial Real Estate with Carlos Salguero

In this episode, Brad chats with Carlos Salguero, an entrepreneur and real estate expert with over 20 years of business and investment experience. After starting four seven-figure companies and exiting one for an eight-figure sum, Carlos is now focused on helping others invest in commercial real estate and building a $1 billion portfolio. He shares how his father's life inspired his interest in real estate and recounts the story of his first commercial deal—a 50,000-square-foot warehouse he purchased for his business. He also discusses a more recent, large-scale mixed-use property he acquired in Tennessee, explaining the importance of hands-on management and a strong business plan.
🔑 Key Topics Covered:
The Path to Real Estate: Carlos shares how watching his father live off the rent from a warehouse complex he built influenced his own investment philosophy.
The First Big Deal: The story of how Carlos bought a 50,000-square-foot warehouse in Denver, navigating dishonest brokers, a difficult seller's agent, and unexpected renovation costs to see the property’s value increase from $1.2 million to over $8 million.
Active vs. Passive Investing: The difference between being a limited partner (LP), who simply writes a check, and a sponsor (GP), who actively runs the deal like a business.
Lessons from a Challenging Deal: The journey of acquiring a Class A mixed-use property in Tennessee and overcoming challenges like a lender reducing proceeds by $1 million.
The Power of Hustle: How Carlos and his team went from 66% commercial vacancy to 100% leased in just three years by actively seeking out tenants, rather than relying on a broker.
Why Reputation is Everything: The importance of maintaining a five-star reputation online and keeping tenants happy, a lesson Carlos learned from his e-commerce background.
The Next Chapter: Carlos outlines his goal to acquire $100-200 million in Class A assets annually and reach a $1 billion portfolio by 2030.
💬 Memorable Quotes:
"I always thought that trading cash for real assets was a great idea." — Carlos Salguero
"That's the power of real estate, right? Even folks that don't have systems and don't do things right... they can make money." — Carlos Salguero
"Nobody will hustle more than you will for yourself." — Carlos Salguero
🔗 Connect with Carlos Salguero:
🌐 Website: https://cs3investments.com/
📸 Instagram: https://www.instagram.com/iamcarlosinfinite
💼 LinkedIn: https://www.linkedin.com/in/cssalguero/
🎙️ Connect with Host Brad Weaver:
💼 LinkedIn: https://www.linkedin.com/in/bradweaver

40 Years of Real Estate Experience with Arn Cenedella

In this episode, Brad chats with Arn Cenedella, founder of Spark Investment Group, who brings over 40 years of real estate experience, including 35 years as a realtor in Silicon Valley. Arn shares his transition from single-family to multi-family real estate investing, the lessons learned from his biggest investing mistake during the 2008 subprime crisis, and his strategy for building long-term wealth. He also discusses the benefits of syndication and how he leverages his experience and network to help others invest in the growing Greenville, South Carolina market.
🔑 Key Topics Covered:
Arn's journey from a residential broker in Silicon Valley to a multi-family syndicator in Greenville, South Carolina.
The transition from single-family to multi-family investing, and the differences in acquiring commercial versus residential properties.
The details of his first multi-family deal: a 43-unit property in Greenville, South Carolina, and why having fixed-rate debt was crucial.
How Arn built his investor pool and gained confidence for his first syndication deal, leveraging his past real estate relationships.
The scalability of multi-family investing compared to single-family properties.
Arn's biggest investing mistake: a condo purchase in Hawaii just before the 2008 subprime crisis, and the lesson of not over-leveraging.
The importance of having cash reserves to ride out market downturns and the long-term outlook on real estate appreciation.
A "home run" deal involving subdividing a large lot to create significant value.
Flipping versus wholesaling as entry points for new real estate investors with limited capital.
An explanation of different types of syndication deals (506b and 506c) and the difference between accredited and sophisticated investors.
💬 Memorable Quotes:
“If you don't know what you're aiming for, you hit it 100% of the time.” — Arn Cenedella
“The truth is, if you make investments, occasionally you're going to make mistakes and you're going to have failures.” — Arn Cenedella
“If an investment's only going to work when things are going perfect, you don't have much protection on the downside.” — Arn Cenedella
“You’re only in trouble when you need to sell.” — Brad Weaver
Connect with Arn Cenedella:
Website: https://www.investwithspark.com/
LinkedIn: https://www.linkedin.com/in/arncenedella/
Facebook Spark Investment Group - https://www.facebook.com/investwithspark/
Connect with Host Brad Weaver:
LinkedIn: https://www.linkedin.com/in/bradweaver