What if the best venture returns come from avoiding trends?not chasing them? In this episode, I sit down with Colin, Co-Founder of Narya, to discuss how he approaches investing in frontier sectors without falling into mimetic behavior. Colin explains why the best opportunities are often ?hidden in plain sight,? how mission-driven investing can still generate venture-scale returns, and why concentration, not diversification, drives outcomes in venture. We also explore defense, space, and advanced manufacturing, and how timing, business model innovation, and founder quality ultimately determine success.

What if the biggest edge in investing isn?t picking better assets?but structuring them better for taxes, incentives, and control? In this episode, I sit down with Michel, Founding CIO of a16z Perennial, to discuss how institutional investing frameworks translate to individual portfolios. Michel breaks down why most wealth management fails at true investment management, how misaligned incentives shape outcomes, and why scale, access, and structure matter more than traditional asset allocation. We also explore concentrated portfolios, tax alpha, and how psychology ultimately determines whether a strategy succeeds or fails.

Is the real edge in investing not picking assets but structuring how you allocate capital? Terence Thompson is a Vice President of Investments at DF Enterprises, about how single family offices think about portfolio construction, liquidity, and structural alpha. We break down why Terry uses a total portfolio approach, how family offices create edge through flexibility, and why being a liquidity provider during market stress is one of the most powerful strategies. We also discuss concentration risk in public markets, the evolution of private markets, and how allocators can think about illiquidity, secondaries, and niche opportunities.

What if the biggest edge in venture today isn?t picking companies?but owning the entire lifecycle of capital? In this episode, I sit down with Paris Heymann, Co-Managing Partner of Technology Investing at J.P. Morgan Private Capital, to discuss how the boundaries between public and private markets are breaking down. Paris explains why companies are staying private longer, how value is increasingly accruing to private investors, and why multi-stage platforms are becoming the new model for capturing returns. We also explore how AI is shifting business models from selling software to selling work, why founder quality still drives outcomes, and how power laws continue to dominate both private and public markets.

Is private equity alpha really about picking great deals?or about executing the same playbook better than everyone else? In this episode, I discuss with Monty Yort, Managing Partner at GenNx360 Capital Partners, about how disciplined execution and consistency drive long-term outperformance in private equity. We break down how GenNx360 approaches proactive sourcing, why lower middle market investing creates structural advantages, and how operational improvement and buy-and-build strategies compound value over time. Monty also shares lessons on leadership, mentorship, and why the best firms continuously refine their process rather than chase new strategies.

How do you manage a $26 billion public fund while keeping every investment decision disciplined, every team member calibrated, and every partner accountable? In this episode, I sit down with Mark Steed, Chief Investment Officer of AZ Public Safety Personnel Retirement System, to explore how super forecasting and probabilistic thinking shape portfolio management. Mark shares how lessons from Dr. Phil Tetlock's the Good Judgment Project inform every investment decision, why intellectual humility and calibrated confidence drive better outcomes, and how simplifying portfolios into broad buckets creates flexibility and competition for capital. He also unpacks the role of co-investments, structural alpha, and first principles thinking in public markets.

How do you build a $7 billion portfolio that performs across decades while keeping every client aligned and every manager motivated? In this episode, I sit down with Karen Welch, Chief Investment Officer at Spider Management Company, to explore the evolving role of a CIO in today?s complex investment landscape. Karen shares how lessons from Stanford?s endowment shaped her approach, why the best investment edge comes from people and relationships, and how Spider leverages both to generate top-tier returns. She also unpacks how to navigate private markets, assess the illiquidity premium, and structure portfolios to balance opportunity with risk.

What does it take to raise $270 million in a risk-off market while keeping your personal life, sanity, and team intact? In this episode, I sit down with Scott Painter, Founder & CEO, TrueCar, to unpack the 21-month journey of taking a company private. Scott shares how persistence, strategic thinking, and mental resilience allowed him to navigate investor skepticism, market volatility, and personal stakes. He discusses the lessons he learned from fundraising in both up and down markets, why creating momentum and scarcity is critical, and how setting boundaries transformed the outcome for him and his team.

What if the families with the largest fortunes generate the highest returns not by chasing hot sectors, but by pacing capital, managing liquidity, and investing with a multi-decade horizon? In this episode, I sit down with Douglas Evans, Chief Investment Officer & Partner at Callan Family Office, to explore how a $10B family office approaches private markets like an institutional investor. Doug shares how private capital pacing, vintage year diversification, and strategic GP partnerships drive consistent performance, why continuation vehicles and secondary markets are reshaping liquidity, and how focusing on underlying assets rather than labels helps families build repeatable, long-term returns.

What if the biggest edge in portfolio construction isn?t picking better assets but structuring a portfolio you can actually stick with through cycles? In this episode, I sit down with Chaya Slain, President and CIO at Virtera Partners LLC, to unpack how families can access institutional-quality investing without building a full family office. Chaya explains why alternatives are often the true driver of outperformance, how trend following can reshape risk and return, and why behavioral discipline matters more than perfect asset selection.

What if the real edge in venture isn?t picking the hottest companies, but structuring your portfolio, pacing capital, and building relationships in a way most investors never do? In this episode, I sit down with Jamie Melzer, Founder and Managing Partner of Altra Venture Partners, to break down how she built a firm focused on late-stage venture and secondaries at the height of market dislocation. We discuss why rising interest rates in 2022 created a rare entry point, how buying private tech companies at 40 to 80 percent discounts reshaped the opportunity set, and why transaction risk often matters more than company risk in secondary markets. Jamie explains her concentrated, power-law-driven portfolio strategy, how she sources deals in an opaque and relationship-driven ecosystem, and why access, not awareness, is the true barrier in private markets.

What if the best venture returns come from the LPs that are most patient and most strategic? In this episode, I sit down with Scott Voss, Partner at HarbourVest, to explore how the $150B multi-manager firm generates consistent outperformance across venture, growth equity, buyouts, and secondaries. Scott shares how consensus risk, vintage year timing, and strategic co-investing shape returns, why continuation vehicles and evergreen structures are transforming private markets, and how long-term relationships with GPs create first-look access to top deals.

What if building a portfolio for high-net-worth investors is more about managing downside risk than chasing returns? In this episode, I sit down with Damien Bisserier, Managing Partner and Co-CIO at Evoke Advisors, to explore how he constructs diversified portfolios for ultra-high-net-worth families. Damien shares why after-tax returns, alternative assets, and private markets matter more than concentrated US stock bets, and how behavioral insights and client-centered thinking drive long-term compounding. He also dives into venture capital, the importance of relationships, and the nuanced ways to identify managers who deliver repeatable alpha.

What happens when AI turns a $40B legal software market into a $1T opportunity? In this episode, I talk with David Eckstein, CFO of Legora, about scaling one of the fastest growing enterprise AI companies in history. David explains how Legora went from zero to $100M in 18 months, why AI is expanding markets rather than just disrupting them, and how the role of CFO is evolving into a strategic operator across every part of the business. We discuss vertical vs horizontal AI, why AI companies must focus on workflows instead of prompts, and how talent density and culture become the ultimate differentiators in high growth environments.

Is AI the biggest risk to equity portfolios or the biggest opportunity? In this episode, I talk with Christopher Vogt about how institutional investors think about risk, portfolio construction, and manager selection across public and private markets. We discuss AI disruption, why governance and structure matter more than asset labels, and how to evaluate managers using both quantitative and qualitative frameworks. Chris also shares lessons from building an endowment style portfolio from scratch, why patience matters in private markets, and how position sizing can make or break long term outcomes.

What does investing look like in a world dominated by AI? In this episode, David Weisburd talks with Alex Wissner-Gross about the profound implications of technological singularity and the evolution from LLMs to reasoning models. They discuss AI personhood, economic rights, and the rise of AI agents, as well as strategic investment approaches in a post-singular world. The conversation delves into Elon Musk's visions for massive compute capabilities, the role of science fiction in predicting technological advancements, and strategies to prevent technological unemployment. The episode concludes with a look towards the future and a call to action for listeners.

Is private equity becoming an asset gathering business instead of a performance business? In this episode, I talk with Sam Tidswell-Norrish, Partner at Access Holdings, about how private equity is evolving across sourcing, value creation, and distribution. We discuss why performance is still the core product, how AI is reshaping deal flow and portfolio operations, and why the lower middle market remains one of the best places to generate alpha. Sam also shares how culture, curiosity, and relationships drive long term success in an increasingly competitive and automated industry.

What if your family office could invest like a founder and a VC at the same time? In this episode, I sit down with Shane Neman, founder of a multi-entity family office with $850M AUM, to explore how he approaches venture investing, deep tech, and portfolio construction. Shane shares how his two decades as a SaaS founder shape his edge as an investor, why transparency and founder relationships matter more than fund mandates, and how he balances high-conviction bets with a rational family office lens. He also dives into frontier tech, co-invest structures, and building a diversified yet opportunistic portfolio.

Why buy an office when everyone else is selling? In this episode, I sit down with Tim Barrett, CIO of the Texas Tech University Endowment, to explore how he builds high-conviction portfolios across private equity, real estate, and hedge funds. Tim shares why governance, manager selection, and a generalist team structure drive consistent alpha, how he balances risk and upside with portable alpha, and why lower middle market investments can outperform flashy venture deals. He also dives into building team culture, aligning incentives, and using the endowment?s size and flexibility to access niche opportunities others can?t.

Why do most institutional investors still allocate heavily to large private equity funds? Alex Abell of RCP Advisors explains why the lower middle market has consistently outperformed, driven by less competition, faster exits, and stronger value creation. He breaks down the structural reasons LPs stay in large buyouts, including access constraints, manager selection difficulty, and career risk. The conversation also covers how top LPs evaluate managers, what actually predicts performance, and where alpha exists in private markets today.

What if the best investors aren?t generalists at all, but operators who double down on the one place they truly have an edge? In this episode, I sit down with Nathan Cooper, Founder and Managing Partner of Barrel Ventures, to explore how a family with nearly a century in food transformed itself into a focused investment platform. From early mistakes outsourcing everything to building a differentiated edge in food and beverage, Nate shares how conviction, pattern recognition, and network-driven investing compound over time.

What does it take for a GP to successfully raise capital in today?s venture and private markets? In this episode, I sit down with Ron Biscardi, co-founder and CEO of iConnections, to unpack the realities of LP relationships, fund-raising cycles, and scaling a global platform for capital introduction. Ron shares insights on how humility, patience, and responsiveness differentiate managers, why business risk matters more than returns for LPs, and how building trust over years compounds into large-scale success.

What if influencer marketing isn?t about chasing mega-followers, but activating the creators who already love your brand? In this episode, I sit down with Aris Yeager, Founder of Storytime, to explore how he built a platform connecting brands with nano and micro creators to run highly targeted campaigns at scale. A creator himself known online as European Kid, Aris leverages his own social experience to help businesses automate gifting, engage loyal audiences, and measure campaign effectiveness while focusing on authenticity over follower count.

What if the best way to navigate credit markets is not about chasing yield but controlling risk? In this episode, I sit down with Danielle Poli, Co-Portfolio Manager of Global Credit at Oaktree, to explore how she manages a $20 billion portfolio within a $223 billion firm. Danielle shares how focusing on core income, rigorous underwriting, and a flexible toolkit allows her team to navigate complex markets while remaining defensive or opportunistic as conditions change.

What if the best venture returns come from managers no one else can access? In this episode, I sit down with Jorge Felippe, CEO of Almulla, a Dubai-based single family office, to explore how he builds high-conviction private markets portfolios while managing a multi-generational family and complex governance. Jorge shares why alignment, patience, and process matter more than flashy deals, and how a thoughtful approach to fund selection can capture early-stage alpha without the chaos of direct investing.

What if emerging markets aren?t a trap, but most investors just approach them wrong? In this episode, I sit down with Robert Koenigsberger, Founder and CIO of Gramercy, to explore how he has built a $7 billion emerging markets platform by focusing on high conviction, structured private credit, and long-term partnerships. After nearly four decades in emerging markets, Robert has pioneered strategies that capture the upside while managing risk, proving that careful underwriting, local knowledge, and disciplined execution outperform passive index approaches.

Will AI soon write investment memos, analyze deals, and run workflows inside investment firms? In this episode, I speak with Chaz, founder of Model ML, about the rise of agentic AI and how investment firms are beginning to automate complex workflows across private markets. Chaz explains how Model ML originally started as an internal tool built inside his family office to manage investments more efficiently ? before evolving into a fast-growing AI platform used by asset managers, banks, and consulting firms. We discuss why chat-based AI tools have limitations for professional workflows, how firms can achieve major productivity gains through automation, and why the next phase of AI will shift from productivity toward generating investment insight.

What if the most compelling private equity opportunities aren?t brand-new deals, but the ones other investors have already ?vetted? and are leaving on the table? In this episode, I sit down with Michael Woolhouse, Head of Continuation Vehicles at TPG Capital, to explore how he approaches the rapidly growing single asset continuation vehicle (CV) market?a space where sponsors can roll their most successful companies into new structures, creating liquidity while maintaining upside potential.

What does it take to build a world-class private equity portfolio for an 800-year-old institution? In this episode, I sit down with Sam Sturge, Head of Private Equity at the University of Cambridge endowment, to discuss how he rebuilt the program with a mandate to generate inflation plus 5% returns for generations. Before joining Cambridge, Sam worked at Morgan Stanley and Partners Capital, and today he oversees a concentrated portfolio of buyout and venture relationships within the university?s £4.5 billion endowment.

What changes when wealth stops being about building and starts being about preserving? In this episode, I sit down with Jonathan Dane, CIO and Founder of Defiant Capital, to explore how family offices think about portfolio construction after a major liquidity event. Drawing on his experience at Goldman Sachs and Jefferies, Jonathan explains why independent advice matters and how families navigate the transition from wealth creation to long-term preservation.

What if one of the most overlooked $700 billion pools of capital in the U.S. is quietly shaping private markets? In this episode, I sit down with Jennifer Mink, President of Investment Performance Services, an investment consulting firm overseeing roughly $70 billion in assets under advisement, to discuss how Taft-Hartley pension plans approach long-term investing. Jennifer shares how IPS designs portfolios that balance public and private markets, using disciplined asset allocation and diversification to improve overall portfolio efficiency and manage risk across market cycles.

Why are private markets still managed in spreadsheets when hundreds of billions of dollars are at stake? In this episode, I sit down with Ryan Eisenman, Co-Founder and CEO of Arch, a platform supporting more than 550 clients and over $405 billion in alternative assets. Arch is building an operating system for private markets that helps investors manage the operational complexity of alternatives across private equity, venture, hedge funds, credit, and more, bringing modern infrastructure to a part of the financial system that has historically relied on manual processes and fragmented data.

What if the best private equity opportunities are the ones no one else is set up to pursue? In this episode, I sit down with Jeff Collins, Founder and Managing Partner of Cloverlay, to explore how he built a $2 billion firm by going where capital isn?t. After 14 years at Morgan Stanley Investment Management, Jeff spun out to focus on what he calls ?uncorrelated private assets? - niche, often overlooked segments where return dispersion is wide and operator selection matters more than financial engineering.

Why would an LP invest in the GP instead of the fund? and what problem is GP stakes really solving? In this episode, I sit down with Todd Owens, Managing Partner of Cantilever Group, to unpack the world of GP stakes. Todd explains what investors are actually buying when they take a minority stake in an alternative asset manager, why liquidity risk is the central challenge, and how structural innovation could reshape the asset class.

What separates elite venture LPs from everyone else? and why do most family offices underestimate the governance required to win? In this episode, I sit down with Michael P. Larsen, a longtime Partner at Cambridge Associates, to unpack nearly two decades of building venture and private equity portfolios for leading institutions and family offices. Michael shares why longevity may be the ultimate competitive advantage in asset management, how governance quietly determines venture outcomes, and why portfolio size can matter just as much as manager selection. We dive into power laws, spiky returns, growth equity?s overlooked role, co-invest best practices, and how benchmarking can help LPs stay disciplined during optically challenging cycles.

What if the biggest untapped source of alpha isn?t better investments? but better tax structure? In this episode, I sit down with Andrew Berman, Co-Founder and Managing Partner of Arqitel, to explore the overlooked power of tax-aware private real estate investing. After starting his career at AQR Capital Management and working closely with one of its co-founders inside a family office, Andrew saw firsthand how tax-aware strategies transformed public market investing. He realized private markets had yet to fully adopt the same discipline. We break down structural alpha, why many private real estate managers are incentivized to sell too soon, and how taxable investors can materially improve long-term wealth creation by aligning investment strategy with tax structure. In increasingly efficient markets, tax may be one of the few durable advantages left.

What if the easiest alpha in public markets isn?t stock picking? but taxes? In this episode, I sit down with Zach Wainwright, Founder of Twin Oak ETF Company, to break down structural alpha, ETF tax efficiency, and how high-net-worth investors can compound capital more intelligently. Zach shares lessons from his time at Wellington, TIFF, and inside a single-family office ? and why long time horizons, incentive alignment, and tax awareness may be more powerful than traditional stock-picking alpha. We also dive into tail-risk hedging inside an ETF wrapper and how families can design portfolios to survive extreme drawdowns without sacrificing long-term compounding.

What if success isn?t about talent? but about multiplying your effort by 10? In this episode, I sit down with Grant Cardone, CEO of Cardone Capital, to break down the mindset behind the 10X Rule, omnipresence in marketing, raising billions from retail investors, and why quantity always precedes quality. Grant shares how he built a $5B real estate portfolio, scaled a media machine that sends hundreds of millions of emails per year, and combined Bitcoin with multifamily real estate to create a new hybrid investment vehicle. We also unpack why most people underestimate effort, why repetition builds self-esteem, and why illiquidity may be the real edge in investing.

If private equity generates alpha, why are investors still paying for beta? In this episode, I sit down with Roger Vincent, Founder and CIO of Summation Capital, to break down portfolio construction, co-investing, and fee alignment in private equity. After more than a decade leading Cornell University?s multi-billion-dollar private equity portfolio, Roger shares why diversification in PE actually increases expected return, how elite endowments use co-investments to systematically reduce fee drag, and why most allocators are misaligned with the capital they steward. We also unpack Summation?s industry-first structure?charging carry only on alpha over a public benchmark and offsetting fees through a no-fee, no-carry co-investment program.

Why does applying institutional investing frameworks often fail for taxable investors and families? David Weisburd speaks with Aneet Deshpande about adapting the endowment model to private clients, the rise of tax-aware private market investing, and why governance, pacing, and asset location matter more than product selection. Aneet explains how taxes, liquidity needs, and behavioral risks fundamentally change portfolio construction?and why clarity of objectives is the real edge.

Can ethics, generosity, and long-term relationships really outperform aggression in venture capital? David Weisburd speaks with David Hornik about why ?nice guys finish first? eventually,? how power-law outcomes shape a venture career, and why reputation compounds more reliably than tactics. Hornik explains why backing unflinchingly ethical founders isn?t just moral?it?s a durable competitive advantage in an industry defined by uncertainty.

Why have continuation vehicles become one of the fastest-growing segments in private markets? David Weisburd speaks with Benjamin Carper about what?s driving record CV volume, how these transactions solve structural mismatches in private equity fund lives, and why both LPs and GPs hold mixed views on the strategy. Ben explains how continuation vehicles create liquidity, extend ownership of high-quality assets, and reshape portfolio management across buyout and venture markets.

Why has liquidity across private markets broken down and what does it mean for institutional portfolios? David Weisburd speaks with Alex Ambroz about collapsing distributions, the rise of continuation vehicles and secondaries, and why many allocators are facing a structural mismatch between models and reality. They explore whether ?private is the new public,? how incentives shape GP behavior, and what LPs must change to adapt to a new normal of prolonged illiquidity.

What happens when AI stops assisting humans and starts replacing decision-making itself? David Weisburd speaks with Camilo Acosta about the rise of agentic AI, why incumbents still leave massive openings for startups, and how AI will reshape labor, venture capital, and entire asset classes. Camilo explains how investing ahead of regulation, betting on founders over ideas, and building for a fully agentic future define the next era of venture.

What happens when capital markets move from batch processing to real time? David Weisburd sits down with Yuval Rooz to discuss his path from Citadel and DRW to founding Digital Asset and building the Canton Network. Yuval explains why blockchain is less about crypto speculation and more about upgrading the infrastructure of global capital markets?unlocking 24/7 settlement, asset utility, and new forms of liquidity across public and private markets.

How do you compete with Sequoia and Andreessen while running a $650M fund and still expect to outperform? In this episode, I sit down with Glenn Solomon, Managing Partner at Notable Capital, to break down how focused early-stage investing can outperform mega-platform venture funds. Glenn explains why 70%+ of venture dollars now go into mega-rounds over $100M, why Notable stays disciplined at seed and Series A, and how delivering ?unscalable? founder support creates real edge. We also go deep on Anthropic, the so-called ?software apocalypse,? AGI narratives, and where durable alpha exists in an AI-dominated world.

Why does execution velocity matter more than pedigree at the earliest stages of company building? David Weisburd speaks with Eric Bahn about the concept of ?hustle,? why early judgments about founders tend to persist, and how throughput, learning speed, and grit outperform traditional signals in pre-seed investing. Eric explains Hustle Fund?s wide-net strategy, its community-driven platform model, and how changing startup timelines are reshaping venture economics.

Why are vertical AI applications emerging as some of the most defensible opportunities in technology today? David Weisburd speaks with Nick Beim about why context?not raw intelligence?is becoming the key driver of AI performance, and how vertical software is reshaping wealth management, legal services, and defense. Nick shares how legacy infrastructure, industry economics, and human-centered workflows create enduring opportunities for AI-driven transformation.

How should investors think about risk when traditional measures like volatility fall short? David Weisburd speaks with Jeff Blazek about portfolio construction across institutions and family offices, why drawdown matters more than standard deviation, and how allocators should balance public and private markets. Jeff shares first-principles thinking on liquidity, behavioral risk, and building resilient portfolios across market cycles.

Where does real edge still exist in public markets and how do you size risk when certainty doesn?t exist? In this episode, I talk with Ari Levy, Founder and CIO of Lakeview Investment Group, about applying probability theory, arbitrage, and disciplined position sizing to public equity investing. Ari explains how early lessons from card counting and game theory shaped his approach to risk, why small-cap markets remain structurally inefficient, and how activism, arbitrage, and management access can create asymmetric outcomes?without blowing up the portfolio.