The Mack Podcast

Rob Della Bovee, owner of a top Virtuoso agency serving UHNW clients; Shelby Donley, former Virtuoso leader building UHNW advisor services; Ben Vaschetti, co-founder of Maison Benjamin for family-office lifestyle management; Kristen Oliveri, CEO of Wealth Reimagined for rising generations of wealth. They discuss trust and seamless execution, contingency planning and 24/7 problem solving, multigenerational tailoring, authenticity versus curation, sustainability and AI’s role.

Justin Papadakis, USL deputy CEO focused on stadium-anchored real estate and long-term soccer growth. Bobby Henebry, CIO of Elway Capital, specializes in bespoke sports and real estate deals for a single-family office. Kyle Auffray, ex-NFL player and sports investor, builds fan-centric investment vehicles. They discuss where value is created today: real estate, media rights, fan engagement, platforms, and how to access and size positions across the sports landscape.

Jerry Graunke, family-office operator focused on services businesses; Tim Ladin, family-office investment professional with value-investing roots; Adam Freda, MD at 50 South Capital specializing in secondaries. They discuss the rise of secondaries into a core allocation. They cover liquidity-driven selling, GP-led continuation funds, diligence speed and alignment, and where families choose funds versus direct deals.

Celine Fitzgerald, a third-generation family member turned coach and philanthropic leader, and Kristen Heaney, founder of In Three Generations, who coaches families on multi-generational wealth. They discuss how current stewards can create transparency, define roles, and educate rising family members. Short practical steps, storytelling, and community are highlighted to prepare smooth leadership transitions.

Andrew Hutcheson, SVP at Wedbush advising family offices on sports and tech-enabled plays. Joe Roos, CIO at Zitten Family Office expanding allocations into the sports ecosystem. Tom Conaghan, veteran sports transactional lawyer at McDermott. They discuss why institutional capital flooded sports, minority stakes and new liquidity models, valuation and diligence quirks for teams, and tech-driven fan engagement and adjacencies like arenas and media.

Daniel Krutoy, a technology and cybersecurity leader with 25+ years focused on family offices and financial services. He discusses how hybrid work shifts attacks to individuals and endpoints. He explains the importance of layered defenses like identity protection, EDR, and MFA. He warns about phishing, vendor compromises, privacy and reputation risks, and the emerging threats from AI-driven attacks.

Brent Sullivan, independent industry analyst and author of Tax Alpha Insider who advises on tax-aware portfolio design for high-net-worth families. He breaks down tax loss harvesting frameworks and using volatility as opportunity. He explains coordinating tax-aware structures across households and entities. He covers direct indexing, crypto quirks, leverage to amplify tax alpha, and tech needed to monitor lots and wash sales.

Jenny Kowal, Managing Director and Senior Income Tax Strategist at IEQ Capital with 25+ years advising ultra-high-net-worth families, joins to reframe tax as a strategic lever. Conversations cover why income tax now drives portfolio decisions. Topics include tax-aware investing vs chasing alpha, treating public equities as tax assets, concentrated stock solutions, and priorities like netting, location, and deferral.

Chris Brimsek, managing partner advising firms on strategy and succession. David Sawyer, founder specializing in GP-stakes underwriting and AI for alternatives. John Lueken, multifamily office executive focused on partnership structuring. They discuss GP stakes versus LP investments, underwriting signals and valuation, governance and key-person risk, direct versus fund access, and sizing GP-stakes within private equity allocations.

Bill Bogart, former family office CIO who builds relationship-focused development plans, and Kit Case, trainer for rising leaders in ultra-wealthy families, discuss next-gen preparation. They explore why episodic education fails. They cover risks of delaying preparation. They outline four capital buckets and the role of conflict-free, long-term mentorship in turning ownership into stewardship.