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On this episode, Kevin chats with Wes Whitman, Co-Founder and Co-Managing Partner of Whitman Peterson, a real estate private equity firm that has raised nearly $3 billion in equity across five flagship funds and three sector-specific sidecars and backed operating platforms through 325+ asset-level investments representing more than $40 billion in total capitalization. Wes calls Whitman Peterson a Sherpa team. Great entrepreneurs are elite climbers who have trained their whole lives, and even the best climbers climb with partners: somebody who has been up the route before, who helps you avoid the crevasses, and who can carry a lot of the bags. The conversation covers what GP-aligned capital actually means, how the firm splits capital between operating companies and the real estate those companies create, why they insist on deal-by-deal approval rights, why Wes expects M&A among operating companies to pick up, and how a top-10 global fund manager came to refer operating partners to them. On the personal side, Wes gets into partners for life, why the CEOs he backs build boards they do not need, and why the "who" is the main decision you make.

On this episode, Kevin chats with John McNellis, a principal of McNellis Partners, the Northern California commercial development firm he co-founded in the early 1980s. John and his two partners have completed nearly 100 deals, almost all supermarket-anchored neighborhood centers within a two-hour drive of San Francisco, and have funded every one with their own capital since 1990. They cover why he scaled the business down by a factor of ten, how he turns brokers into an off-market deal team, why he refuses to underwrite to IRR, where he still finds mispriced ground leases, how a five-person firm punches outside its weight class, and the quiet power of being able to say you have enough.

In this episode, Kevin chats with Bill Douglas, CEO of OpticWise, a data and digital infrastructure company for commercial real estate. Bill helps owners and operators stop treating their digital systems like scattered gadgets and start managing them like mission critical infrastructure. Bill calls it the triangle. The property manager runs the building, the asset manager runs the investment, the IT manager runs the office systems, and the building's networks, sensors and data sit in the middle belonging to nobody. Most buildings OpticWise audits are running more than ten networks when they need two. The rest is wasted CapEx on the way in and wasted OpEx for the life of the hold. Bill puts numbers on the opportunity. On a retrofit, if OpticWise can't find $300 per door per year of NOI, they don't take the job. On a new build, $600 is the baseline and $1,000 is a home run, on top of what gets saved by designing digital infrastructure alongside the structural and mechanical. In a market with no cap rate compression, no cheap debt and rising concessions, that's real value hiding in plain sight. The second half goes personal. Bill has managed multiple sclerosis for over 20 years and survived a ski accident that broke 13 bones, then came back to find his business had grown 25% while he was out. He talks about the half days he blocks off twice a week, the $100 he owes the company pool every time he touches work on vacation, and why the voice in your head is worth hearing but not believing.

On this episode, Kevin chats with Shlomo Chopp, the Managing Partner of CASE, a distressed commercial real estate advisory and investment firm that runs about 90% advisory work and a small, highly selective book of opportunistic investments. Shlomo and his team are currently working on roughly 20 loans totaling more than $2 billion of debt, and he comes out of a family office with over 35 years of experience owning and operating about 70 properties across the country. He's a college dropout with no formal finance training who taught himself structured finance by cracking open CMBS loan documents during the 2010 downturn, and has since invested in, structured, or advised on nearly $5 billion of commercial real estate. His role is fundamentally one of translation, bridging the gap between the language of the operator and the language of the lender. The conversation covers why complexity is where the opportunity lives, why binary thinking is the trap most owners fall into, how to argue the inputs rather than the outputs in a workout, and the rolling consequences of not reading your loan documents.

On this episode, Kevin chats with Aleks Gampel, co-founder of Cuby Technologies, a hardware and software company that's built a completely new type of home construction. With 243 people across three continents and a million engineering hours invested, Cuby has developed a mobile micro factory: a containerized, plug-and-play factory in a box that ships to any market and manufactures single-family homes with unskilled labor at roughly $100 a square foot in 30 days. Aleks walks us through how Cuby has built the antithesis to traditional modular construction by localizing manufacturing rather than centralizing it. He gets into why construction is fundamentally a logistics problem, how 168 shipping containers and 600 SKUs come together on a 6.5-acre site, and why the company chose to manufacture its own windows, framing, and sandwich panels rather than relying on third-party suppliers. He also gets into the economics of the mobile micro factory at roughly $25 million all-in, why Cuby targets regional home builders who can't compete with the Lennars and DR Hortons of the world, and how the company bridges two capital worlds. Venture capital funds the platform while infrastructure equity and debt fund each factory as its own SPV. On the business side, Aleks shares why most startups fail on partnership dynamics, what drew him to a problem nobody has cracked, and why solving for housing sits at the base of Maslow's hierarchy. His take on building inside a conservative industry is straightforward: don't try to reinvent the wheel, just figure out how to make it spin faster.

On this episode, Kevin chats with Derek Myron, Managing Partner of Centura Wealth Advisory, a San Diego-based registered investment advisor specializing in ultra-high-net-worth families. Since founding Centura in 2014, Derek and his team of 62 professionals have grown to $1.4 billion in assets under management. Derek walks us through how Centura has built a practice that goes well beyond traditional asset management into comprehensive tax planning and financial engineering. He gets into how sophisticated strategies around index replication, hedging, and tangible property regulations can materially change the tax picture for high income earners, and why that planning conversation is fundamentally different from what most advisors offer. He also gets into how RIAs like Centura think about allocating into real estate, where private market investments fit within a UHNW portfolio, and why real estate remains a core tool in the tax planning conversation, not just an asset class. On the business side, Derek shares how he thinks about building a firm, designing accountability around roles before people, extracting genuine core values from top performers, and why he prioritizes his team's growth above everything else. His advice for entrepreneurs is straightforward: stay humble, find good mentors, and build a peer network that functions like a real board of directors.

Kevin chats with Jay Rollins about his 40-year journey building and selling four companies, from RTC-era distressed acquisitions to growing JCR Capital to $1.6 billion in AUM before selling to Walker Dunlop in 2018. Now Jay's doing something different with Canopy Real Estate Partners—scouting real estate operators between 35 and 45 who've proven they can do deals but have never recruited institutional capital. His pitch: let Canopy put discretionary capital in your hands, teach you fund management, and help you build a platform, taking no equity in your company beyond what's earned at the project level. Jay discusses how he's matched his fund product to investor appetite with a structure that behaves like a real estate bond—6% current return, four-year duration, 18% at exit, with only 50-55% leverage—designed for LPs tired of "trust me, I'll call you in five years." The conversation covers why having discretionary capital in the middle market is a massive competitive advantage, how proper promote structures and vesting drive team alignment, and why basic interpersonal skills like looking someone in the eye and remembering their name will put you ahead of 95% of the younger generation.

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.