On this episode, Kevin chats with Mark Roppolo of HFS Capital Partners about operating in the space between family office and traditional fund. Mark explains how this structure allows HFS to maintain unusual discipline—sometimes doing just two deals a year when market conditions don't warrant more. The conversation covers their approach to sourcing deals exclusively through operating partners rather than marketed opportunities, why they underwrite the sponsor as much as the asset itself, and how they've deployed $280MM across over 70 deals without a single failed capitalization. Mark shares his philosophy that success in real estate comes from tenacity and deal flow rather than being the smartest investor, discusses the accountability framework he learned at the Naval Academy, and explains why staying closely connected to operating partners through daily conversations drives better investment decisions than spreadsheet analysis alone.

On this episode, Kevin chats with Tony Yousif, Executive Managing Director of SVN, about building a nationwide distressed real estate advisory platform through relationships rather than transactions. Tony shares his journey from working at a convenience store and borrowing from his now-wife's salary to survive, through 2.5 years of 100-hour weeks before his first $25,000 commission check. The conversation explores how he positioned himself as a "conductor of the orchestra" between lenders and local market experts rather than just a broker, working with institutions like Wells Fargo, Bank of America, and Fannie Mae to navigate troubled assets. Tony explains why he operates as a farmer rather than a hunter—planting seeds and nurturing relationships instead of chasing deals—and how this approach has given him the freedom to fire clients and walk away from $80,000 monthly retainers when relationships aren't mutually respectful. They discuss the difference between relationship brokers and transaction brokers, why banks' "extend and pretend" strategy looked genius through the last crisis, and Tony's philosophy on harmony versus balance across the three circles of life: business, friends and family, and self.

On this episode, Kevin chats with Jeff Pensiero, founder of Baldface Lodge, a legendary backcountry snowcat skiing operation in British Columbia's Selkirk Range that many consider the pinnacle of snowboarding lodges. Jeff shares his 26-year journey starting with $40,000 borrowed off a stated-income mortgage, bootstrapping the operation from a canvas dome and single snowcat into a world-class facility with 3,000 people on the waiting list and wait times stretching 8 years or longer. The conversation explores how falling in love with his wife Paula led him to Nelson, BC and sparked the vision for the lodge, his connections with snowboarding legend Craig Kelly and even the Foo Fighters, and the reality of reinvesting every dollar back into the business for 17 years with little to no personal income. Jeff opens up about the realities of entrepreneurial commitment, his refusal to accept failure, how high standards and strong vision helped weather countless challenges, and the role trusted mentors played in cutting the path forward.

On this episode, Kevin chats with Damien Farrell, founder of West Modular, a construction company manufacturing modular apartment buildings from a 210,000 square foot facility in Tijuana that can produce 1,500-2,000 apartments annually in half the time of conventional construction. Damien brings over $500MM in completed developments to the conversation, including three major hotels—Dream Hollywood, Thompson Hollywood, and Tommie Hollywood—plus a hospitality portfolio that grew to 20 venues across three states before being acquired by Las Vegas-based Hakkasan Group. The conversation explores how his frustration with cost overruns, delays, and change orders on those projects, combined with experience entitling and permitting over $1B in developments, drove him to commit to what he calls "the future of construction." Damien discusses the technical and financial challenges plaguing development today, and how modular construction addresses not just the product itself but the myriad of external challenges that make housing unaffordable and projects difficult to fund.

On this episode, Kevin chats with Jack Cohen, Managing Director of ArrowMark Partners and founder of Dark Knight Ventures, a business consultancy focused on helping smart, creative salespeople become more successful. Jack shares his journey taking Cohen Financial from a single office with $200MM in annual loan production to 25 offices with $6B in annual production and a loan servicing portfolio over $30MM before a successful exit. The conversation covers what Jack calls "stupid human tricks"—lessons learned along the way through countless scenarios—including his split with his father over business philosophy, the difference between efficiency with things versus effectiveness with people, and why the real estate capital advisory business is about doing the work rather than outsmarting it. Jack discusses how standing for something provides common ground for teams to rally around, why risk equals volatility of outcome and smart investing is about identifying and pricing that risk, how self-awareness enables entrepreneurial clarity and conviction, and why 2026-2027 might produce some of the best vintage real estate deals in a decade as overleveraged assets get repriced.

On this episode, Kevin chats with Connor Mitchell, Managing Director at Cascadia Capital, the #2 independent investment bank in the nation, about selling founder-led businesses in the human capital and professional services sector. Connor works with companies valued between $100MM and $350MM, with 65% of Cascadia's business coming from family and founder-led companies. The conversation unpacks why many founder-led businesses struggle to sell and the mindset shifts that accompany liquidity events, covering where the market is trading today, how buyers create value post-acquisition, and why selling is less about "can I sell" and more about whether the price justifies walking away. Connor explains the objective measures sellers should consider before going to market—like the mix of 1099 versus W2 employees, customer concentration, employee utilization rates, and percentage of business originated by the founder—along with what Quality of Earnings is and why it matters. They discuss the typical timeline from building a deck to closing, why a soft touch on sales beats blasting deal memos everywhere, and the importance of putting a plan in place if a sale is truly where you want to land.

On this episode, Kevin chats with Bill Vanderstraaten, President and founder of Chief Partners, a Dallas-based family office that invests LP equity into commercial real estate as part of the Trever Rees-Jones holdings. With a team of just 6 professionals typically investing $5MM to $15MM per deal, they manage about $1.2B across 80 assets with 30 GP operating partners and have built over 8MM square feet of commercial space since 2007. The conversation explores how family offices differ from opportunity funds, why holding too long is a common mistake family office investors make, and how culture and integrity are central to Chief's underwriting of potential operating partners. Bill discusses where flexibility shows as a competitive advantage for family office equity, the merit of providing investors an earnest assessment of risk, and why Chief sees itself as more than commodity capital. They cover the value of curiosity in leveling up skills, why people remain at the heart of real estate due to the high degree of trust required, what a high idle brings to your career, and how a sailing analogy applies to the challenge of being an entrepreneur.

On this episode, Kevin chats with Jimmy Silverwood, president of Affirmed Housing Group, a San Diego-based affordable housing developer that's completed $2.8 billion in projects and created over 5,500 apartments across 70 communities since 1992. Jimmy shares his journey from growing up in the affordable housing business to working at Turner Construction, then joining Affirmed as an acquisitions and finance analyst before eventually becoming president under his father James, who started the company after getting blown up in the S&L crisis. The conversation dives deep into the complexity of affordable housing, breaking down the critical distinctions between workforce and affordable housing, the intricate process of securing and monetizing tax credits, and how developers navigate both 4% and 9% credits to build their capital stack. Jimmy explains the competitive landscape of tax credit awards, managing crucial timelines between credit awards and development permits, the strategic use of 90% land loans for acquisitions, and the scoring systems that determine project viability. They discuss Affirmed's business model of positioning themselves as essential vendors to cities while maintaining control through an integrated general contractor approach, and why mastering financial models is the true key to unlocking success in affordable housing development.

On this episode, Kevin chats with Josh Volen, Principal and Co-founder of CIRE Equity, an $890MM NAVREIT that functions like Blackstone's BREIT with market-to-market transparency and limited redemption. Josh shares his journey from becoming a top broker at Marcus & Millichap over 6 years to starting CIRE in 2010, funding acquisitions entirely through high net worth syndications until 2019 when they combined 13 assets into the NAVREIT and partnered with a broker dealer to accelerate growth. The conversation covers how six years in the Marcus & Millichap boiler room built his skill set, why CIRE views themselves as operators rather than capital allocators, and Josh's philosophy that his primary job is replacing himself a little bit more every day. They discuss how successful remote work requires intentional accountability and robust meeting structures, CIRE's risk-first underwriting approach, their unique positioning as a professionally managed family office nimble enough to beat institutional competitors, and how their fee structure and employee compensation drive alignment. Josh opens up about the distinction between transaction shops and sustainable businesses, why hiring better than yourself is critical, and the importance of showing up for yourself first with intention, clarity, and continual learning.

Because it didn’t come out in the pod, for those interested in investing with CIRE, you can find the group at CIREequity.com. 

On this episode, Kevin chats with Josh Volen, Principal and Co-founder of CIRE Equity, an $890MM NAVREIT that functions like Blackstone's BREIT with market-to-market transparency and limited redemption. Josh shares his journey from becoming a top broker at Marcus & Millichap over 6 years to starting CIRE in 2010, funding acquisitions entirely through high net worth syndications until 2019 when they combined 13 assets into the NAVREIT and partnered with a broker dealer to accelerate growth. The conversation covers how six years in the Marcus & Millichap boiler room built his skill set, why CIRE views themselves as operators rather than capital allocators, and Josh's philosophy that his primary job is replacing himself a little bit more every day. They discuss how successful remote work requires intentional accountability and robust meeting structures, CIRE's risk-first underwriting approach, their unique positioning as a professionally managed family office nimble enough to beat institutional competitors, and how their fee structure and employee compensation drive alignment. Josh opens up about the distinction between transaction shops and sustainable businesses, why hiring better than yourself is critical, and the importance of showing up for yourself first with intention, clarity, and continual learning.

Because it didn’t come out in the pod, for those interested in investing with CIRE, you can find the group at CIREequity.com.