How I Invest with David Weisburd

E299: Why Institutional LPs Are Moving Into Lower Middle Market PE

What does it mean to be a true partner to lower middle market businesses? David Weisburd speaks with Peter Elliot Rothschild about building RF Investment Partners around listening first, designing bespoke capital solutions, and investing as the first institutional capital in family-owned companies. Peter discusses minority versus control investing, the role of trust and relationships, and why value creation in the lower middle market is driven less by financial engineering and more by people, incentives, and execution. Highlights: Building RF Investment Partners with a listening-first investment philosophy Why being first institutional capital creates unique opportunities Bespoke capital structures combining debt and equity Challenges of fundraising without fitting neatly into LP “buckets” Minority investing misconceptions and downside protection strategies Why lower middle market investing is fundamentally a people business The role of executive chairs and 180-day value creation plans Aligning employee incentives with tangible operating KPIs CEO summits as a value-creation and leadership tool Relationship compounding as a long-term competitive advantage Guest Bio: Peter Elliot Rothschild is the Founder and Managing Partner of RF Investment Partners, a private investment firm focused on providing flexible, bespoke capital solutions to lower middle market businesses. He has deep experience across both control and minority investments, with a focus on partnering with family-owned companies as their first institutional capital. Peter is known for emphasizing trust, alignment, and operational value creation over financial engineering, and for building long-term relationships with management teams, operators, and limited partners. 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. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. 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 Rothschild: LinkedIn: https://www.linkedin.com/in/peter-rothschild-44a190/ 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 (0:34) Benefits of being the first institutional capital and advantages of bespoke capital solutions (2:34) Challenges of fundraising and alignment with future investment philosophies (4:11) Misconceptions about minority investing and control dynamics (5:47) The role of being a therapist in family-owned businesses and underwriting risk (8:40) Flexible ownership stakes, advisory roles, and developing a 180-day plan (10:57) Value-add in sub $50 million enterprise companies and CEO Summit benefits (14:24) Compounding relationships and the importance of people in investment decisions (17:37) Balancing EQ and IQ with CEO psychology and background checks (19:27) Managing non-cooperative CEOs and the evolution of private equity (21:40) Critique of traditional buyout funds and benefits of having former CEOs as backers (25:08) Impact of personal relationships on investment approach (26:19) Closing remarks

E298: How Family Offices Think About Illiquidity, Taxes, and Compounding

How do tax efficiency, private markets, and structural change intersect in modern portfolio construction? David Weisburd speaks with Jeffrey Fulk about his career across hedge funds, fund-of-funds, and wealth platforms, and how AlTi Global approaches tax-aware investing, private credit, evergreen structures, and evolving access to private markets. Jeff shares insights on where opportunity is emerging as markets shift and why after-tax outcomes increasingly drive investment decisions. The views expressed herein are those of Jeffrey Fulk and do not necessarily reflect the views of AlTi Global, Inc. or its affiliates (“AlTi”). This is for informational purposes only and does not constitute investment advice, an offer to buy or sell any financial product, a solicitation to become an advisory client of AlTi or an investor in any AlTi-advised fund, or an endorsement of AlTi, its advisory services, or investment strategies, including AlTi-advised funds. While the information and views presented are believed to be accurate and expressed in good faith, there is no assurance that they are correct, complete, or will not change over time. All investments carry risk, including loss of principal. Past performance is not indicative of future results. Highlights: Jeff’s unconventional path into finance and early hedge fund investing Lessons from the LTCM collapse and market dislocations Why tax-aware strategies are reshaping wealth portfolios Mechanics and risks of long-short tax loss harvesting strategies The growing role of private credit and credit secondaries ETFs, correlation risk, and implications for portfolio construction Evergreen structures versus closed-end private funds Why operational simplicity matters for wealth clients Continuation vehicles and selective buyout opportunities The potential impact of private assets entering 401(k)s Guest Bio: Jeffrey Fulk is a senior investment professional at AlTi Global, a global wealth and asset management platform with approximately $100 billion in assets under management. He has held senior roles across hedge funds, fund-of-funds, and wealth management, including positions at Guggenheim Partners and Hightower. Jeff focuses on portfolio construction, tax-efficient investing, and integrating private markets into long-term wealth strategies. 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. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Jeffrey Fulk : LinkedIn: https://www.linkedin.com/in/jeffreyfulk/ 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 (5:40) Key asset classes and strategies at Alti Global (9:56) Tax strategies in investing: Long short tax loss harvesting (17:54) Exploring the private credit market and secondaries (20:41) The rise of fixed income ETFs (24:07) 401(k)s and private assets: A new frontier (28:08) Innovations in investment structures (31:04) Evergreen structures vs. managing capital calls (34:35) Analyzing current trends in private equity (37:55) How to access top private companies (39:33) Reflections: Advice for the younger self (41:30) Closing remarks

E297: Advisory Boards & LPACs: A Complete Masterclass for GPs

Why do so many advisory boards look impressive on paper but fail to deliver real value when it actually matters? In his second appearance on the podcast, I sit down again with Matt Curtolo, a senior advisor to both GPs and LPs who has worked with more than 600 general partners across venture, growth equity, and private equity. Matt breaks down the biggest misconceptions around advisory boards and LP advisory committees, why “performative” governance quietly destroys trust, and how the best managers design advisory structures with real purpose. We get tactical on compensation, LPAC construction, advisor selection, and how great firms turn advisors into a true strategic weapon—not window dressing. Highlights: The critical difference between LPACs, boards of advisors, and independent advisors Why most advisory boards fail before they ever meet Purpose and clarity as the starting point for any advisory structure “Performative” advisors vs. functional advisors The value of truly independent, unconflicted feedback Advisor vs. full-time hire: how to decide Best practices for advisor compensation (carry, cliffs, and alignment) Why smaller LPACs outperform large, unwieldy committees How advisors can (and should) support fundraising Common LPAC construction mistakes GPs keep repeating Diversity of LP perspectives as a governance advantage Why transparency turns LPACs into long-term advocates Guest Bio: Matt Curtolo is a senior advisor to general partners and limited partners across venture capital, growth equity, and private equity. Over his career, he has worked with and advised more than 600 general partners, served on numerous advisory boards and LP advisory committees, and helped managers navigate fundraising, governance, and firm-building challenges. Today, Matt focuses on helping emerging and established managers design effective advisory structures, improve LP communication, and build durable franchises across private 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. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Matt Curtolo: LinkedIn:https://www.linkedin.com/in/matt-curtolo-caia/ 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 (2:36) Independent Advisers' Objective Feedback (5:52) Roles and Differences of Advisers vs. Full-Time Team Members (7:33) Compensation Frameworks for Advisory Board Members (10:34) Advisory Relationship Success Rate and Turnover (13:22) Building Advisory Boards from Scratch (16:03) Advisory Board Construction Based on Team Needs (17:14) Optics and Substance in Advisory Boards (19:19) LinkedIn Affiliations as Commitment Signals (20:34) Strategic Use of LP Advisory Committees (22:53) Leveraging Advisory Boards for Fundraising and LP Introductions (25:02) Mistakes in Constructing LP Advisory Committees (LPAKs) (27:40) Optimal LPAK Size (28:33) Venture Market Outlook for 2026 (32:40) Closing remarks

E296: Former CIO of CalSTRS on Why LPs Overpay for ‘Innovation’

What actually separates great institutional investors from average ones and why does governance matter more than brilliance? In this episode, I talk with Christopher J. Ailman, former Chief Investment Officer of CalSTRS, about the decisions that shaped one of the largest and most successful public pension funds in the world. Chris reflects on more than two decades leading CalSTRS, why asset allocation and governance drive the vast majority of outcomes, and how building a resilient, low-cost, long-term portfolio matters far more than chasing the latest investment trends. We also discuss culture, decentralization, and what CIOs consistently get wrong when managing people and risk. Highlights: Why governance is the most underrated driver of returns Asset allocation as ~90% of long-term performance Borrowing from the Canadian pension model Building in-house capabilities to reduce costs Why chasing “shiny objects” destroys net returns Cost discipline as a competitive advantage at scale Culture as a hidden source of alpha Centralized vs. decentralized decision-making Portfolio resiliency and downside protection Why great investors come from wildly different backgrounds Guest Bio: Christopher J. Ailman is the former Chief Investment Officer of CalSTRS, where he served for more than 23 years and helped grow the fund into one of the largest and most respected institutional investors globally. Over a 30+ year career in institutional investment management, Chris became widely recognized as one of the world’s top CIOs. He is now the founder of Ailman Advisers, where he focuses on coaching and mentoring CIOs and institutional investors, as well as teaching and public speaking. He also serves as Chair of The 300 Club of global CIOs and is Chair Emeritus of the Milken Global Capital Markets Committee. 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. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Christopher Ailman: LinkedIn: https://www.linkedin.com/in/christopherailman/ 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 (0:06) Key decisions and achieving above median returns (2:18) Lowering investment costs and borrowing ideas (5:36) Avoiding fads and building a world-class culture (10:51) Governance and crisis anticipation in portfolio strategy (13:34) Hiring and unique due diligence strategies (17:37) Future of asset allocation and special GP encounters (21:18) Closing remarks

E295: Why AI Agents Will Quietly Replace 80% of Investment Teams

Why are humans — not models — still the biggest bottleneck to AI progress, and what happens when that bottleneck becomes a business? In this episode, I talk with Ali Ansari, Founder and CEO of micro1, about the hidden layer powering today’s AI breakthroughs: high-quality human intelligence. Ali explains how micro1 pivoted from an AI recruiting startup into a critical data infrastructure company for frontier AI labs, why expert-generated data is now the limiting factor in model performance, and what needs to change for AI agents to actually work in production. We also explore how focus, market timing, and ruthless prioritization enabled micro1 to scale more than 30× in a single year. Highlights: Why AI progress is still overwhelmingly driven by humans The shift from pre-training to expert-level post-training data Why AI agents fail in production despite great demos Evaluation frameworks as the missing layer for agents How micro1 serves frontier labs and Fortune 500 enterprises The hardest pivot: firing customers to focus on the right market Why market selection matters as much as product quality How investors are using AI to gain workflow-level edge Humans as operators of agents, not coworkers How focus became micro1’s biggest competitive advantage Guest Bio: Ali Ansari is the Founder and CEO of micro1, an AI platform for human intelligence that connects highly skilled experts — including PhDs, professors, and industry specialists — with leading AI labs to generate high-quality training and evaluation data. Under Ali’s leadership, micro1 rapidly transformed from an AI recruiting startup into a core data infrastructure provider for frontier models, scaling more than 30× in a year. Ali represents a new generation of AI-native founders building companies at the intersection of human expertise and machine intelligence. 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. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Ali Ansari: LinkedIn:https://www.linkedin.com/in/ali-ansari-7b240a18b/ 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 to MicroOne and Customer Demographics (0:55) The Advancement of LM Models and Human Involvement (2:13) AI Agents in the General Market: Opportunities and Obstacles (5:57) AI Versus Human Intelligence in Performance (6:15) Identifying the Killer Application for AI Agents (7:06) AI Investment Strategies: Early Case Studies (8:28) The Journey of an AI Native Entrepreneur (9:21) AI's Impact on Venture Capital and Private Equity by 2030 (10:48) Human Roles in an AI-Dominated Future (12:13) AI Takeover Concerns and Safety Measures (14:17) Professional Growth Advice for AI Entrepreneurs (17:28) MicroOne's Market Focus and Strategic Reorientation (19:00) Insights on Adaptive Leadership in Tech (20:00) Extracting Ground Truth from Customer Feedback (20:54) Closing remarks