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    Business

    How I Invest with David Weisburd

    How I Invest with David Weisburd is a podcast that interviews the world’s leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.

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    Copyright: © Copyright 2025 How I Invest with David Weisburd

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    Latest Episodes:
    E263: Inside the $5 Billion Fund Backed by 700 LPs Dec 16, 2025
    Show notes

    How do you scale a growth equity firm from a $52M first fund to $5B across six funds—without losing discipline or trust? In this episode, I talk with Brian Neider, Managing Partner at Lead Edge Capital, about building a durable growth equity platform by combining rigorous metrics with deep relationship-building. Brian shares how Lead Edge created a differentiated LP model centered on high-net-worth individuals who actively support portfolio companies, why communication and education compound trust over decades, and how a strict investment framework helps avoid negative alpha as the firm scales. We also discuss why exits matter more than paper gains, how to think about “walking dead” portfolio companies, and what truly energizes long-term investing.

    Highlights:

    • Why Lead Edge raised its first fund from individuals, not institutions
    • How 700+ LPs became a competitive advantage, not a liability
    • The importance of disciplined metrics before falling in love with founders
    • How structured LP engagement improves deal sourcing and outcomes
    • Why communication, education, and transparency compound trust
    • The danger of “negative alpha” and unstructured decision-making
    • How pattern recognition scales exponentially—but portfolio work does not
    • Why exit planning should start on day one
    • The hardest part of growth equity: managing the “walking dead”
    • What motivates Brian most after more than a decade of investing

    Guest Bio:

    Brian Neider is a Managing Partner at Lead Edge Capital, where he helps oversee the firm’s investment strategy, portfolio management, and operations. He is a member of the firm’s Investment, Disposition, and Management Committees and has led or co-led investments in companies including Toast, Asana, Duo Security, Lucid, Amplitude, and Workhuman. Prior to joining Lead Edge in 2012, Brian invested at Bessemer Venture Partners and FTV Capital, focusing on mid-market growth opportunities across software, internet, and business services. He holds a B.S. in Economics from the Wharton School and an MBA from Columbia Business School and is based in New York.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    #VentureCapital #VC #Startups #OpenLP #assetmanagement

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

    Stay Connected with Brian Neider:

    LinkedIn: https://www.linkedin.com/in/brian-neider-7774041/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Introduction (1:20) The first fund, early advice, and challenges with institutional investors (5:33) Building and managing relationships with investors (12:06) The role of LP dinners, NextGen events, and full-time engagement teams (17:01) Key metrics and strategies for investment selection (21:32) Competitive market strategies and the value of LP introductions (25:35) Utilizing introductions, advice, and understanding growth factors (32:40) Addressing challenges with portfolio companies and LP feedback (38:14) People-centric opportunity filtering and advice for early-stage LeadEdge (42:37) Comprehensive framework and strategies around exits (45:16) Closing remarks

    E262: The 50-30-20 Portfolio: How Institutions Are Rebuilding 60/40 Dec 15, 2025
    Show notes

    How do you build portfolios that survive liquidity crises, inflation shocks, and the most volatile market regimes in modern history? In this episode, I talk with Alfred Lee, Deputy Chief Investment Officer at Q Wealth Partners and one of Canada’s most experienced multi-asset portfolio architects. Alfred previously managed over $75 billion across equities, fixed income, commodities, factor strategies, and thematic ETFs at BMO—while also spending a year at the Bank of Canada running part of its quantitative easing program during the pandemic. He shares what he learned from overseeing $25B in fixed income and $50B in equities, how ETFs transformed the public markets, why alpha is harder to generate than ever, and why alternatives, real assets, CTAs, and discretionary macro strategies must anchor the next generation of portfolios.

    Highlights:

    • Lessons from overseeing $75B across fixed income, equities & commodities
    • What Alfred learned managing QE operations at the Bank of Canada
    • Why generating alpha in public markets is harder than at any point in history
    • How Q Wealth Partners serves as Canada’s version of a modern RIA aggregator
    • Building model portfolios using open architecture while staying within regulatory guardrails
    • The “debasement regime”: why inflation will appear in bursts for years
    • Why CPI understates real-world cost of living and what that means for investors
    • How to allocate to Bitcoin, gold, and real assets through one-ticket solutions
    • 60/40 is outdated: Alfred’s 50/30/20 framework for the next decade
    • Behavioral finance as the biggest driver of investor outcomes
    • Why illiquidity is a feature, not a bug—and the “virtue of staying invested”
    • How to evaluate private credit, private equity, and alternative strategies
    • Why liquidity collapses cause correlations to spike across asset classes
    • How to run “portfolio war games”: preparing for the next crisis
    • The single greatest lesson Alfred learned from 2008 and 2020: never assume liquidity

    Guest Bio:

    Alfred Lee is the Deputy Chief Investment Officer at Q Wealth Partners, where he oversees portfolio construction, asset allocation, and investment platform design for one of Canada’s fastest-growing wealth platforms. Before joining Q Wealth, Alfred spent over a decade at BMO, where he helped grow its ETF franchise to $100 billion in assets and managed more than $75 billion across fixed income, equities, commodities, and factor strategies. He previously completed a one-year secondment at the Bank of Canada, where he ran part of the central bank’s quantitative easing program during the pandemic, helping restore liquidity and functionality to the provincial bond and funding markets.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    #venturecapital #vc #startupsuccess #openlp #assetmanagement

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

    Stay Connected with Alfred Lee:

    LinkedIn: https://www.linkedin.com/in/alfred-lee-cfa-cmt-dms-b329025/ Q Wealth Partners: https://www.qwealth.com/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Introduction (0:39) Influence of mentors in Alfred's career & building an asset management firm (2:23) Launching a gold bullion fund & overview of Q Wealth Partners (4:38) Portfolio allocation strategies and views on alternatives (8:49) Inflation, purchasing power, and philosophy on Bitcoin and gold (11:55) Behavioral finance and modernizing the 60/40 portfolio (18:19) Mapping portfolio construction with privates and diversification (23:26) Addressing the J-curve effect and interval funds usage (27:44) Handling unique investment opportunities and avoiding deworsification (32:13) Adding investments and the importance of uncorrelated returns (39:05) Timeless advice and managing liquidity during crises (41:51) War games and crisis preparation for asset managers (44:14) Closing remarks

    E261: How Sovereign Wealth Funds Create Alpha w/Peter Madsen Dec 12, 2025
    Show notes

    What does it take to build a sovereign wealth fund from scratch—and still outperform in some of the hardest markets in decades? In this episode, I talk with Peter Madsen, Chief Investment Officer of the Utah School & Institutional Trust Funds Office (SITFO), one of the most quietly sophisticated sovereign wealth funds in the United States. Peter shares how he went from running hedge fund portfolios in London to becoming the first investment hire tasked with modernizing Utah’s endowment. We break down SITFO’s philosophy on mean reversion, factor-based investing, public vs. private markets, active vs. passive strategy, and how a small CIO team competes with far larger institutions. Peter also explains why small caps are broken, how he shifted capital into private equity, why micro-VC funds outperform mega-funds, and how SITFO uses AI and collaborative models to underwrite managers in a world of overwhelming information.

    Highlights:

    • Why Peter left London to build a sovereign wealth fund with permanent capital
    • The decline of fund-of-funds—and how it shaped his CIO philosophy
    • Why mean reversion still matters, even when markets feel one-sided
    • Active vs. passive: why benchmarks themselves are an “active decision”
    • Why small caps are structurally different today—and no longer reliably outperform
    • The “equal-weighted portfolio” origin story and how SITFO built asset allocation from scratch
    • Why SITFO shifted capital from small caps into private equity
    • How micro-VC funds outperform large venture funds mathematically
    • Why SITFO partners with seed funds, super angels, and Fund I/Fund II managers
    • The collaborative LP model: revenue-sharing, co-invest structures, and research leverage
    • How SITFO built a zero-and-zero co-invest platform to recapture fee drag
    • Using AI to screen manager decks, extract underwriting criteria, and systematize memo writing
    • Why sovereign wealth fund investing differs from pensions and endowments
    • Managing cashflows from land revenues while protecting K–12 distributions
    • Why Sharpe ratio optimization is misleading for long-horizon investors
    • Factor modeling, Venn by Two Sigma, and designing purpose-driven portfolios

    Guest Bio:

    Peter Madsen is the Director and Chief Investment Officer of the Utah School & Institutional Trust Funds Office (SITFO), where he has led the state’s sovereign wealth fund since 2015. He previously served as a Managing Director at Cube Capital in London and as a Partner at RVK, advising large institutional investors on global portfolios, governance, and asset allocation. At SITFO, Peter has overseen the evolution of the fund from a more traditional portfolio into a globally diversified allocator across public and private markets, grounded in mean reversion, factor-based risk management, and long-term stewardship for Utah’s public education system. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    #venturecapital #vc #startups #openlp #assetmanagement #interview #podcast

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

    Stay Connected with Peter Madsen:

    LinkedIn: https://www.linkedin.com/in/pmads/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Introduction (2:02) Assessing fund managers and market conditions; Active vs. passive investing (7:22) Shift from small cap to private equity; Diversification and asset allocation (11:46) Factor exposure and tools for analysis in investment strategies (16:08) Investment strategy and evaluation in venture capital (23:03) Collaborative model and structuring co-invest accounts for better returns (27:10) Utilizing AI tools in investment screening (31:51) Sovereign wealth fund investing insights (32:55) Closing remarks

    E260: How Founders Access Liquidity in Pre-IPO Companies Dec 11, 2025
    Show notes

    How do you turn distressed opportunities into structural alpha—again and again—in an asset class most investors still misunderstand? In this episode, I’m joined by Philip Benjamin, Co-Founder and Managing Partner of Colzen Capital, about how he built a differentiated pre-exit liquidity strategy that serves founders, executives, and investors simultaneously. Philip shares how his fourth-generation real estate background and the 2008 financial crisis shaped his investing worldview, how he applies a distressed-real-estate mindset to late-stage ventures, and why Colzen’s structured equity financing model creates downside protection, aligned incentives, and access to elite companies long before IPO. We also discuss portfolio construction, expected return math, founder psychology, and why this emerging asset class is quietly becoming massive.

    Highlights:

    • How the global financial crisis shaped Philip’s investment philosophy
    • The real-estate insight that led to Colzen’s equity financing model
    • How Philip helped create a solution for executives facing the 90-day exercise deadline
    • Why founders want liquidity without selling—and how Colzen solves that
    • The investor’s advantage: downside protection, PIK interest, and equity participation
    • Why late-stage venture outcomes cluster between 0.7x–3x—and how to systematize that
    • Understanding structural alpha vs. manager alpha in Colzen’s model
    • How to underwrite companies past binary risk and still outperform
    • The psychology of founders choosing Colzen over selling secondary
    • Why pre-exit liquidity is already a $60B asset class
    • Education as the bottleneck—and why this market will become mainstream
    • Why diversification across industries matters even within structured finance
    • Building long-term LP relationships and evolving from Fund I to Fund II
    • Creating win-win transactions: non-zero-sum liquidity for founders and investors
    • The family-office analogy of planting, harvesting, and replanting new seeds

    Guest Bio:

    Philip Benjamin is the Co-Founder and Managing Partner of Colzen Capital, where he leads one of the most innovative structured equity financing strategies in the late-stage venture ecosystem. Philip’s investment philosophy is informed by his fourth-generation real estate family background and by experiencing the 2008 financial crisis just as he graduated college. His family’s timely liquidity event before the crash enabled him to explore private alternatives and eventually develop a distinctive approach to venture risk.

    Before launching Colzen, Philip invested across fund managers, direct deals, and special situations, eventually partnering with Sam Buleau to refine a pre-exit liquidity model that supports founders and executives without forcing them to sell shares. Philip applies a distressed-real-estate mindset to venture—focused on downside protection, valuation discipline, and structured upside—and has become a leading voice in the growing pre-exit liquidity asset class.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    #venturecapital #vc #startupsuccess #openlp #assetmanagement

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

    Stay Connected with Philip Benjamin:

    LinkedIn: https://www.linkedin.com/in/philip-h-benjamin/ Colzen Capital: https://www.linkedin.com/company/colzen/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Introduction (1:12) Transitioning to private alternatives and founding Colson (2:16) Mentorship and early real estate investment strategies (4:17) Creation of the equity financing model and navigating market crashes (6:34) Fund formation, strategy, and comparison to private equity (8:03) Value proposition for founders and executives (11:22) Investment strategy, decision-making, and expected returns (18:01) Evolution from Fund One to Fund Two and structural alpha (21:48) Expanding investor access and synergy in the venture space (24:10) Trends in pre-exit liquidity solutions and staying private (27:36) LP feedback and the importance of diversification (33:55) Relationship management and collaboration opportunities (37:50) The family office business and value creation (40:49) Decision-making and planning for future generations (41:32) Closing remarks

    E259: The Institutional Way to Invest in Crypto w/Rennick Palley Dec 10, 2025
    Show notes

    What does it take to build four top-decile crypto funds in one of the most volatile asset classes on earth? In this episode, I talk with Rennick Palley, Founder of Stratos, about how he approaches crypto investing with a disciplined, mathematically grounded framework. We break down how Stratos constructs top-performing venture and liquid portfolios, why crypto is shifting from momentum-driven trends to fundamentals, how to size positions without blowing up, and why Bitcoin and gold are behaving the way they are in today’s macro environment. Rennick also shares his philosophy on decisiveness, conviction, and avoiding the costly mistakes investors make when they hesitate.

    Highlights:

    • How Stratos generated four top-decile crypto venture funds
    • Why fund size matters more than most crypto investors admit
    • Crypto’s evolution from momentum to fundamentals-driven investing
    • How to size early-stage positions and avoid portfolio blowups
    • Why the smartest investors focus on: “Just don’t screw this up”
    • The future of Bitcoin as digital gold
    • Why gold is outperforming Bitcoin this year — and why that may change
    • What on-chain data reveals about global truth systems
    • Why most crypto VC funds underperform the benchmark (just like traditional VC vs. Nasdaq)
    • How institutions should think about crypto allocation and volatility
    • The behavioral cost of hesitation and the danger of inaction
    • Why crypto provides “free leverage” — and why that makes risk management essential
    • Thoughts on government seizure scenarios, custody, and ETF risk
    • Meme coins, debasement psychology, and the role of speculation
    • How investors can compound returns across cycles without blowing up

    Guest Bio:

    Rennick Palley is the Founder of Stratos, an investment firm he launched in 2016 after entering the crypto markets. Under his leadership, Stratos has built multiple top-decile venture funds and a liquid strategy designed to compound capital across highly volatile cycles. Before founding Stratos, Rennick worked as a Research Associate at Sanders Capital, a $75 billion global equity manager known for its fundamental, value-driven approach. He holds dual Bachelor’s degrees in Applied Mathematics and Mechanical Engineering from Southern Methodist University and a Master’s in Quantitative Finance from the Massachusetts Institute of Technology. Rennick blends value-investing discipline, quantitative rigor, and crypto-native insight, making him one of the most analytical and thoughtful investors in digital assets today.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    #venturecapital #vc #startupsuccess #openlp #assetmanagement

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

    Stay Connected with Rennick Palley:

    X/Twitter: https://x.com/RennickPalley Stratos: https://www.stratos.xyz/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Introduction (2:00) Key principles in crypto venture investing (4:18) Analyzing large outcome clustering in crypto (5:12) Momentum vs. value in evaluating crypto wins (8:14) The future of information and crypto as a hedge (12:22) Historical parallels and Bitcoin's potential challenges (17:45) Strategies for a potential Bitcoin confiscation scenario (21:01) Debating Bitcoin's future valuation and effects of forced sales (27:10) Insights from Rennick Palley and liquid crypto strategies (31:34) Comparing crypto to traditional endowment strategies (33:06) Sector importance and risk management in crypto (39:47) Systematic decision-making and the role of an engineering background (43:43) Portfolio construction and institutional crypto allocation (45:52) Transitioning from venture to liquid crypto investments (49:08) The benefits of illiquidity in alternative investments (50:31) Fund liquidity and managing investor relationships (53:10) Determining the optimal portfolio size for Bitcoin (54:13) Utilizing leverage in crypto investing (57:12) Guidance for newcomers to crypto investing (59:45) Closing remarks

    E258: Ryan Serhant: Why Leaders Who Don’t Evolve Get Left Behind Dec 09, 2025
    Show notes

    How do you build a $10B real estate empire by turning yourself into a media company—and why is vulnerability the ultimate competitive advantage? In this episode, I talk with Ryan Serhant, founder and CEO of SERHANT., one of the most influential real estate brokerages in the world and a pioneer at the intersection of real estate, media, entertainment, and technology. Ryan breaks down the turning points that shaped his career—from selling a $13M townhouse through YouTube a decade ago, to betting everything on social media before anyone believed in it, to building a fast-growing real estate ecosystem powered by content, authenticity, and scale. We dive into Season 2 of Netflix’s Owning Manhattan, the biggest highs and lows of his year, the reality of leading a thousand-agent organization, and why the future of real estate is screenless, human-centric, and powered by creators.

    Highlights:

    • How a YouTube video led to Ryan’s first $13M sale and changed his career
    • Why he bet his entire future on social media long before agents believed in it
    • The balance between going viral and preserving luxury brand credibility
    • The power of authenticity online—and why the internet detects B.S. instantly
    • How Season 2 of Owning Manhattan became his most raw and emotional year on TV
    • The behind-the-scenes reality of office fights, breakdowns, and $60M deals
    • Why vulnerability drives more business than perfection ever could
    • The moment he realized he had to evolve from broker-friend to CEO-leader
    • What broke at SERHANT. as the company scaled from 500 to 1,500 agents
    • The difference between respect vs. trust—and why employees must earn both
    • Ryan’s four rules for every new hire, including “perform magic”
    • Why culture is defined by the behaviors you allow, not what you write on paper
    • The future of content: micro-dramas, interactive media, and 5-minute emotional arcs
    • How SERHANT. is building a screenless, AI-powered real estate transaction
    • Advice for new agents: join a team, do the work no one wants to do, and get reps

    Guest Bio:

    Ryan Serhant is one of the most recognized and successful real estate brokers on the planet. He is the founder and CEO of SERHANT., a modern multidimensional real estate brokerage operating at the intersection of media, entertainment, education, and technology. Ryan has closed nearly $10 billion in sales and has represented clients in some of the most record-breaking transactions across New York and South Florida. Before launching his firm, he became a global personality as the star of Bravo’s Million Dollar Listing New York and now serves as Executive Producer and lead star of Netflix’s Owning Manhattan. Beyond real estate, Ryan is an entrepreneur, creator, bestselling author, and philanthropist whose content reaches over six million people. SERHANT. has grown rapidly under his leadership, expanding across multiple states and pioneering LISTED, a dedicated YouTube network focused on real estate and lifestyle. Ryan actively supports organizations including City Harvest, Feeding America, the Ali Forney Center, the NYC Sanitation Foundation, the American Cancer Society, and Project Sunshine. He lives in Brooklyn with his wife, Emilia, and their daughter, Zena.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

    ###Stay Connected with Ryan Serhant: LinkedIn:https://www.linkedin.com/in/ryanserhant/ Website: https://serhant.com/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Preview (1:12) Selling a $13 million home via YouTube and the impact of social media (5:40) Authenticity, vulnerability, and balancing content in luxury real estate (12:02) High and low moments, scaling challenges, and leadership (22:29) Special guest insights on season two highlights (24:38) Real-time CEO moments and a major deal gone wrong (27:02) Season two highlights: Miami, Mercedes Benz, and narrative arcs (29:08) Learning from mistakes across seasons one and two (32:06) Discussing the future of content creation and media convergence (34:08) Ryan Serhant's vision for the future of his company (35:53) Advice for new real estate agents and industry insights (37:26) Closing remarks

    E257: What I Learned Advising the World’s Top CIOs at Goldman Sachs Dec 08, 2025
    Show notes

    Why do the world’s best CIOs make investment decisions based on gut — not spreadsheets? In this episode, I’m joined by Julia Rees Toader, CFA, Founding Partner at PrinCap and former Global Head of Portfolio Strategy at Goldman Sachs Asset Management. Julia spent a decade advising sovereign wealth funds, pensions, private banks, and ultra-wealthy families on portfolio construction, risk management, and asset allocation. She shares the biggest lessons she learned from working with the world’s top CIOs — from why diversification rarely drives behavior, to where the smartest allocators take idiosyncratic risk, to how emotions secretly influence the most sophisticated investment decisions.

    Highlights:

    • What Julia learned rising from intern to global head at Goldman Sachs
    • The surprising truth: top CIOs make decisions based on emotions + gut, not just models
    • Why diversification rarely changes behavior — and why portfolios still converge to “vibes”
    • Where the best allocators take idiosyncratic risk without blowing up the portfolio
    • Why ultra-wealthy families succeed by leaning into their operating-business advantages
    • Home country bias: the hidden 10x overweight that destroys returns
    • How to avoid behavioral traps using blind comparisons and rotating devil’s advocates
    • Options-based hedging vs. fixed income — and why 60/40 is outdated
    • Why avoiding losers matters as much as picking winners
    • Why volatility is emotional, not mathematical — and how Julia coaches clients through drawdowns
    • The biggest risk mistakes she saw in sovereign wealth funds & global pensions
    • The seductive danger of storytelling in investing — from thematic equity bubbles to VC pitches
    • How AI will reshape diligence, bias detection, and decision-making

    Guest Bio:

    Julia Rees Toader, CFA, is the Founding Partner at PrinCap, an independent investment portfolio strategy firm advising institutions, family offices, and high-net-worth individuals on asset allocation, manager selection, and strategic portfolio design.

    Before founding PrinCap, Julia served as Head of Portfolio Strategy and Head of Relationship Management at Heritage Holdings, a multifamily office. She previously spent over a decade at Goldman Sachs Asset Management, where she rose from founding intern to Global Head of Portfolio Strategy, advising CIOs of sovereign wealth funds, pensions, private banks, and other large allocators around the world.

    Julia began her career in M&A and business development for an early-stage medical device biotech company. She holds a degree in Mechanical Engineering and Computer Science from Princeton University and is a CFA charterholder.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    #venturecapital #vc #startups #openlp #assetmanagement

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

    Stay Connected with Julie Rees Toader:

    LinkedIn: https://www.linkedin.com/in/julia-rees-toader-cfa-22871030/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Introduction (2:55) Emotional and qualitative considerations in taking idiosyncratic risks in portfolios (6:04) Flexibility and unique strengths of allocators (7:15) Building meaningful portfolios with high returns (8:30) Options-based hedging strategies (11:29) Overcoming behavioral biases and market timing (14:01) Addressing home country bias in investment committees (17:02) Dynamics and size of effective investment committees (19:12) Role of tax strategy and alpha in investment (22:00) Strategic value and managing portfolio fluctuations (25:18) Tools and client risk tolerance in portfolio risk assessment (28:07) Lessons from transitioning to a family office (30:40) Family office investment strategies and perspectives on risk (34:24) Outsourcing tasks and addressing personal liability in decisions (37:01) Evaluating family office dynamics and resource advantages (39:04) Incorporating AI in investment management (41:04) Timeless advice for new investors and thought experiments with AI (45:22) Market timing and asset class favorability (46:09) Closing remarks

    E256: What Fintech Will Look Like in 5 Years - Steve McLaughlin (FT Partners) Dec 05, 2025
    Show notes

    What does it take to build the most dominant FinTech investment bank in the world—starting from a $99 incorporation and a used laptop? In this episode, I speak with Steve McLaughlin, Founder, CEO, and Managing Partner of FT Partners, widely regarded as the leading investment bank in FinTech. Steve has personally closed hundreds of the biggest M&A, capital raise, and IPO advisory transactions in the industry—while pioneering a completely different approach to value creation in investment banking. We cover everything from the humble beginnings of FT Partners, to Steve’s philosophy of “never die,” to his groundbreaking thesis on AI, tokenization, defensibility in FinTech, and why he believes we’re entering a new era of trillion-dollar global financial technology companies. We also dive into the incentives model Steve built that has generated some of the largest fees in the history of investment banking—and why clients keep coming back.

    Highlights:

    • How Steve left Goldman to launch FT Partners during the dot-com crash—with no brand, employees, or clients.
    • The “never die” mindset and why consistency compounds in markets.
    • FT Partners’ deep-work model: 500-page decks, long-term models, and internal data science.
    • How the firm differentiates from Goldman/Morgan Stanley and attracts elite talent.
    • The incentives behind nine-figure fees—and why Steve thinks bankers should be paid like PE/VC when they create real value.
    • Inside FT Partners’ $25M investment in Model ML and how AI will reshape investment banking.
    • Tokenization, stablecoins, and where the next trillion-dollar FinTech giants will emerge.
    • Why the strongest FinTech companies embed AI across every function.
    • How AI will change deal sourcing, buyer mapping, and global transaction execution.
    • The future of FinTech over the next decade—post-AI and fully digital.
    • Steve’s views on money, charity, family, and why he still personally handles major client calls.

    Guest Bio:

    Steve McLaughlin is the Founder, CEO, and Managing Partner of Financial Technology Partners (FT Partners), the leading investment bank focused exclusively on FinTech. Since launching in 2001, Steve has built FT Partners into a globally recognized advisory powerhouse, completing hundreds of the most important transactions across payments, digital banking, crypto, wealth & capital markets tech, InsurTech, healthcare payments, and more.

    He has been ranked #1 on Institutional Investor’s “Most Influential Dealmakers in FinTech,” named Investment Banker of the Year, and recognized as the #1 FinTech banker in Silicon Valley by The Information. FT Partners has also won Investment Banking Firm of the Year four times since 2004.

    Before founding FT Partners, Steve led the Global Financial Technology Group at Goldman Sachs. He earned his BSBA from Villanova University and his MBA from Wharton.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    #venturecapital #vc #startups #openlp #assetmanagement

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

    Stay Connected with Steve McLaughlin:

    LinkedIn: https://www.linkedin.com/in/stevemclaughlinftpartners/ FT Partners: https://www.ftpartners.com

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are solely their own and do not represent the views of Weisburd Capital or its affiliates. Participants may hold positions or have other financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are based solely on the opinions of the speaker and are subject to risks and uncertainties. Information discussed in this episode may include third-party data or opinions; while believed to be reliable, such information has not been independently verified. Listeners should conduct their own research and consult their own professional advisors before making any investment decisions.

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

    (0:00) Introductions (0:04) FD Partners origin story, early challenges, and current scale (1:49) Lessons from market downturns and economic cycles on fintech (3:48) Long-term strategy, resilience, and talent strategy (6:34) Innovations in AI and fintech (7:58) Teamwork and the F1 racing analogy (9:47) Traditional banks vs. fintech and value-added roles (15:15) Private markets and client engagement strategies (19:28) Being labeled the world's richest banker and fintech trends (24:58) The future of fintech and AI's impact (29:06) AI's defensibility and pricing in the fintech market (32:07) Competitive differentiation with AI in fintech (33:24) Closing remarks

    E255: How to Hire the Top 0.1% Dec 04, 2025
    Show notes

    What does it take to recruit the top 0.1% of engineers in the world — and why has talent become the ultimate constraint in AI? In this episode, I’m joined by Chris Vasquez, Founder & CEO of Quantum Talent, one of the most in-demand technical recruiting firms in the AI ecosystem. We discuss why elite engineering talent has become the core bottleneck in AI, how companies can actually attract S-tier builders, what founders get wrong about hiring, and why talent density—not headcount—is the strongest predictor of outcomes in today’s startup environment.

    Highlights:

    • Why AI founders are “at war” — and recruiting firms are the arms dealers. Defining S-tier talent: clear evidence of greatness, spiky abilities, and proven complexity-handling.
    • Capital is abundant; talent is the true constraint in modern AI company building.
    • Why companies must tell a compelling story if they lack high-signal founders or top-tier backers.
    • How AI’s rapid improvement reshapes recruiting needs — fewer engineers, but far more specialized ones.
    • The Sequoia-backed company that failed to hire until they raised their comp bands. (7 declines vs. 17 hires after fixing comp.)
    • Why founders should overpay strategically for the roles that matter most.
    • Key signals elite engineers look for: founding team quality, investor pedigree, mission clarity, and market upside.
    • Why “experience with greatness” de-risks execution in early-stage teams.
    • The #1 heuristic Chris wishes he learned earlier: “If you wouldn’t hire 100 of that person, don’t hire one.”

    Guest Bio:

    Chris Vasquez is the Founder & CEO of Quantum Talent, a specialized recruiting firm focused on placing elite technical talent into leading AI, frontier-tech, and enterprise software startups. Quantum works with hundreds of venture-backed companies and has partnered with 80% of Tier 1 VC firms, helping founders build high-density engineering teams capable of shipping breakthrough products.

    With deep expertise in identifying the top 0.1% of engineers, researchers, and product leaders, Chris and his team have become one of the most trusted upstream partners in the AI ecosystem — operating at the intersection of talent, technology, and high-velocity company building.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    Stay Connected:

    X / Twitter: David Weisburd: @dweisburd

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

    Stay Connected with Chris Vasquez:

    LinkedIn: https://www.linkedin.com/in/chris-vasquez-66137553/ Quantum: https://www.quantumtalent.io/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. david@weisburdcapital.com.

    (0:00) Introduction (2:38) Talent Density and the Shift from Capital to Talent in Startups (5:16) AI's Impact on Talent Recruitment and Compensation Strategies (9:45) What S Tier Engineers Seek in Companies (11:14) Establishing Talent Density by Overpaying Initial Hires (14:28) The Role of Talent in Product-Market Fit (17:21) Strategies for Recruiting Top AI Talent (24:01) The Distinction Between Good and S-tier Recruiters (27:43) Effective Recruiting Heuristics and Compensation Tactics (30:23) Managing Internal Politics for High Compensation Hires (31:48) Timeless Advice for Recruiters (34:34) Closing remarks

    E254: How to Build a 100-Year Venture Firm Dec 03, 2025
    Show notes

    How do you balance power-law outcomes with real risk management while building a durable venture franchise? In this episode, I speak with Mark Peter Davis (MPD) — Managing Partner of Interplay, entrepreneur, author, podcaster, and one of New York’s most active early-stage investors. We discuss how Mark’s philosophy of investing has evolved over 20 years in venture, why VC psychology is so different from other asset classes, and how he manages for both outliers and consistency across vintages. Mark breaks down secondaries, constructing high-access portfolios, founder relationships, narrative risk, the role of operational support, and why grit compounds just like interest.

    Highlights:

    • How 20 years in venture reshaped Mark’s thinking on risk, liquidity, and exit timing.
    • Why early VCs get caught in the “TechCrunch punch” and over-index on hope.
    • Power laws vs. portfolio consistency — why vintages swing and how Mark mitigates volatility.
    • How secondaries, tenders, and mid-market PE can drive liquidity for the “middle 80%” of winners.
    • The “tweener rule”: why Interplay often sells ~50% when outcomes are unclear.
    • Incentive alignment between GPs and LPs — and why building a long-term institution changes behavior.
    • Avoiding narrative traps: why founder behavior and fund construction matter more than storytelling.
    • Brokerage-model VC vs. operational-institutional VC — and why the difference is huge.
    • How soft commits, goodwill, and reference strength drive proprietary access.
    • Entrepreneurship patterns: the “500 problems” every startup faces.
    • Why you can’t learn entrepreneurship in a classroom — only through reps.
    • The compounding effect of grit and staying in the game long enough.

    Guest Bio:

    Mark Peter Davis is a venture capitalist, serial entrepreneur, author, and startup community organizer.

    MPD is the Managing Partner of Interplay, a startup ecosystem based in NYC that supports founders and innovation at every stage. The ecosystem comprises a top-performing venture capital fund, an accelerator, a studio, a services platform, and a multi-family office. With over 100 companies funded, incubated, or founded, he ranks among the most active startup founders and investors in New York City.

    MPD is also an active podcaster, the author of The Fundraising Rules, and the founder of both the Columbia Venture Community and the Blue (Duke) Venture Community.

    Prior to his current ventures, MPD was a venture capitalist at DFJ Gotham Ventures and Primary Ventures. Before entering VC, he was a M&A advisor to Fortune 1000 acquirers at KPMG and a strategy and operations consultant at Bain & Company.

    MPD earned his BA from Duke University and his MBA from Columbia Business School.

    Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

    #venturecapital #vc #startupsuccess #openlp #assetmanagement

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

    Stay Connected with Mark Peter Davis:

    LinkedIn: https://www.linkedin.com/in/markpeterdavis/ X/Twitter: https://x.com/mpd Interplay: http://interplay.vc/

    Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. david@weisburdcapital.com.

    (0:00) Introduction (0:31) Evolution and counterintuitive lessons in venture investing (3:25) Reconciling investment worldviews and managing liquidity (7:35) Decision-making and aligning VC incentives with LP interests (12:03) Building an enduring institution and measuring success (18:07) Achieving access to competitive deals and proprietary deal flow (24:24) Competitive tension's impact on investment support (27:19) Integrity and resources in VC partnerships (30:02) Entrepreneurial experience's value in venture capital (32:24) Startups' challenges and the role of pattern recognition (35:24) Unlearning and cognitive restructuring in entrepreneurship (37:23) Mastering the complexities of long-term entrepreneurship (38:11) Timeless advice for aspiring entrepreneurs and enduring success (41:51) Closing remarks

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