How I Invest with David Weisburd

By 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, Step... more

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The podcast currently has 155 episodes available.

How I Invest with David Weisburd episodes:

April 04, 2025E152: The Peter Thiel Mistake This Crypto VC Won't Make
In this episode of How I Invest, Evan Fisher, Founder of Portal Ventures, shares his expertise in fundraising, venture capital, and deal flow. He discusses the key elements of successful fundraising, how to craft a compelling pitch, and what investors look for when evaluating opportunities. Evan’s insights provide valuable lessons for both founders seeking capital and investors looking for high-quality deals.
Highlights:
Fundraising Strategies: How founders can secure funding more effectively.
Pitch Deck Secrets: What makes a pitch deck stand out to investors.
Venture Capital Insights: How investors analyze deal flow and make investment decisions.
Emerging Investment Trends: The future of startup fundraising.
Building Relationships: The role of trust and networking in venture capital.
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Guest Bio:
Evan Fisher is the Founder of Portal Ventures, a firm specializing in helping startups secure funding through strategic advisory and pitch deck optimization. With a background in investment banking and venture capital, Evan has helped companies across various industries raise significant capital. His deep understanding of investor psychology and storytelling makes him a sought-after advisor for high-growth startups.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
We’d like to thank @Carta, @OldCity and @Republic for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #AssetManagement
Sponsor:
Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.
All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on https://republic.com/
Sponsor:
At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/howiinvest.
Sponsor:
Alpha on the Delta is a captivating, invitation-only alternative investment conference held during New Orleans' legendary JazzFest. Now in its third year, it brings together 150 institutional LPs, 30 leading GPs, and visionary entrepreneurs for a dynamic experience of knowledge sharing, relationship building, and cultural celebration.
The carefully curated agenda features engaging panel discussions with industry leaders, facilitated 1:1 meetings, and exciting social events showcasing the vibrant spirit of New Orleans. Attendees also enjoy access to Weekend 2 of JazzFest, offering an unforgettable blend of world-class music, cuisine, and connections. With limited attendance, Alpha on the Delta fosters meaningful relationships and transformative insights in an unparalleled setting.
Join us for a packed agenda spanning the Alternative Investment industry, music, and world-class cuisine. Visit http://HowIInvestDelta.com.
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Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
Evan Fisher: @evanbfish
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Evan Fisher: https://www.linkedin.com/in/evanfisher1/
Links:
Portal Ventures: https://portal.vc/
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Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(1:24) Crypto's new asset classes and first-check advantages
(3:52) Reinventing in the fast-evolving crypto industry
(8:07) Developing thematic bets and the Bitcoin economy thesis
(14:00) Market size evaluation and strategic partnerships
(15:51) Post-investment founder support and proprietary deals
(18:19) Co-investing risks and analyzing investment failures
(19:52) MEV space exploration and decentralized science (DeSci)
(24:42) Comparing crypto and biotech investing strategies
(26:29) Early investment signals and partner dynamics
(31:21) Long-term crypto survival strategies
(35:04) LP interest in crypto and its liquidity profile
(37:19) Bitcoin's continued dominance and future trends
(41:09) Closing remarks
...more
42min
April 01, 2025 E151: The Rise of Asset-Backed Credit w/Billy Libby
In this episode of How I Invest, Billy Libby, Co-Founder and CEO of Upper90, discusses how his firm is redefining venture capital through a hybrid investment model that combines equity and credit. He shares how Upper90 empowers founders to scale without excessive dilution and offers insights into navigating today’s venture landscape. Billy’s approach to alternative financing provides valuable lessons for entrepreneurs and investors alike.
Highlights:
Alternative Financing: How Upper90's unique blend of equity and credit helps founders grow without giving up control.
Venture Capital Insights: Billy's perspective on the changing dynamics of the VC world.
Supporting Founders: The importance of aligning incentives between investors and entrepreneurs.
Navigating Market Cycles: Lessons from managing capital through different economic environments.
Growth Stories: Real-world examples of companies that benefited from Upper90's approach.
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Guest Bio:
Billy Libby is the Co-Founder and CEO of Upper90, a leading hybrid investment firm providing both equity and credit to high-growth companies. With a background in trading and risk management, Billy leverages data-driven strategies to support founders in building successful, sustainable businesses. Upper90 has backed numerous successful startups and continues to innovate in the venture capital landscape.
Our podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
--
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Billy Libby: https://www.linkedin.com/in/billy-libby-76464b1/
Links:
Upper90: https://upper90.io/
--
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(2:37) Startups' perception of credit usage and structuring investments in new theses like NVIDIA chips
(6:27) When startups should consider credit versus equity and the financial metrics required
(9:22) Seasoning process for financial instruments and capital availability
(12:12) Impact of macroeconomic cycles on capital deployment
(17:36) Network-driven fundraising, time management, and investor relations
(20:23) Institutional practices for transitioning between funds
(24:05) Equity flavor in private credit and catalysts for institutional investors
(26:17) Hiring strategy, rationale for early hiring, and diversification
(29:56) Consistency in returns and addressing lack of diversification
(31:14) Closing remarks
...more
33min
March 28, 2025 E150: Tax-Aware Investing: Insights for Family Offices and UHNW Individuals
In this episode of How I Invest, Aaron Hodari, Managing Director at Schechter, delves into the world of wealth management and alternative investments. He shares how his firm navigates market uncertainties, crafts resilient portfolios, and uncovers unique opportunities for high-net-worth clients. Aaron's insights provide valuable lessons for investors seeking to optimize their financial strategies.
Highlights:
Alternative Investments: How Schechter incorporates alternative assets to diversify and strengthen portfolios.
Tailored Wealth Management: The firm's approach to creating personalized investment strategies for clients.
Market Insights: Aaron's perspectives on navigating economic uncertainty and market volatility.
Private Equity and Credit Markets: The role these asset classes play in long-term financial growth.
Career Lessons: Aaron's key takeaways from years of experience in wealth management.
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Guest Bio:
Aaron Hodari serves as Managing Director at Schechter, a leading wealth advisory and financial services firm. With deep expertise in alternative investments and comprehensive portfolio management, Aaron works with clients to protect and grow their wealth across generations.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
We’d like to thank @Carta for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Sponsor:
At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/howiinvest.
--
Stay Connected: X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Aaron Hodari: https://www.linkedin.com/in/aaronhodari/
Links:
Schechter: https://www.schechterwealth.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(3:01) Diversification and tax optimization for founders
(8:20) Estate planning: Control and management of funds
(10:34) Sponsor: Tactic by Carta
(11:41) Passion, purpose, and income tax planning
(19:02) Comprehensive look at long-short strategies
(24:37) Strategic tax planning and gifting assets
(28:42) Understanding tracking error in tax loss harvesting
(32:57) Overview of the private credit market
(36:17) Exploring middle market direct lending
(39:45) General Partner lending and financing insights
(41:56) Interval funds: benefits, fee structures, and tax efficiency
(49:38) Closing remarks
...more
50min
March 25, 2025 E149: From $0 to $1B in 3 Years: Fin Capital's Meteoric Rise in Fintech Investing
In this episode of How I Invest, Logan Allin, Managing Partner and Founder of Fin Capital, shares how his firm uses AI-powered predictive models to evaluate startups. We explore how AI can assess founder DNA, predict billion-dollar outcomes, and transform the venture capital landscape. Logan also highlights the surprising traits that lead to startup success, the advantages of repeat founders, and what the future holds for fintech. This conversation offers valuable insights for investors, entrepreneurs, and anyone fascinated by the intersection of AI and venture capital.
Highlights:
AI-Driven Investing: How Fin Capital uses generative AI to predict startup success with up to 90% certainty at the seed and Series A stages.
Founder DNA: The 35 key factors Fin Capital assesses to evaluate founder potential, including surprising insights on prior CEO experience.
Repeat Founders Win: Why founders with prior exits are more likely to build billion-dollar companies and how data supports this trend.
Beyond the University Label: Why prestigious degrees don’t significantly predict startup success.
Fintech Focus: How specializing in fintech gives Fin Capital a competitive edge in sourcing and supporting founders.
Evolving AI Models: The role of continuous backtesting and data refinement in improving prediction accuracy.
The Future of Fintech: Logan’s predictions on the next wave of fintech innovation and how AI will continue to shape venture capital.
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Guest Bio:
Logan Allin is the Managing Partner and Founder of Fin Capital, a leading fintech investment firm. With extensive experience in venture capital, Logan has built Fin Capital into a data-driven powerhouse focused on backing repeat founders and disruptive fintech companies. He is a passionate advocate for AI-driven decision-making in venture investing and a recognized thought leader in the fintech ecosystem.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Stay Connected
Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Logan Allin: https://www.linkedin.com/in/loganallin/
Links
Fin Capital: https://www.linkedin.com/company/fin-capital-fintech/
--
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(3:04) Founder DNA and success archetypes
(7:00) Utilizing AI and tracking stealth companies
(10:46) Reverse reference calls and competing with top firms
(16:09) Specialization in fintech
(17:35) Hiring a head of AI and building a strategic LP base
(24:25) Evolving investor relations strategy
(26:48) Decision making on post-lockup shareholding
(29:42) Scaling to a billion dollars in AUM
(35:19) Investing in emerging managers
(37:02) Lessons from SoFi for Fin Capital operations
(39:25) Closing remarks
...more
40min
March 21, 2025 E148: TIFF's $8B Portfolio Revealed: Strategies Institutions Need
In this episode of How I Invest, I speak with Brendon Parry, Head of Private Markets, Deputy CIO, and Managing Director at TIFF Investment Management. Brendon shares insights on TIFF’s mission to serve nonprofit institutions through tailored investment solutions. He discusses the importance of private market investments, the legacy of leaders like David Swensen, and how TIFF partners with foundations to achieve long-term financial goals. Tune in for actionable strategies and valuable perspectives from a seasoned investment professional.
Disclaimer: Brendon Parry, CFA, is the Head of Private Markets, Deputy CIO at TIFF Investment Management. All views expressed by him on this podcast are solely his opinions and do not reflect the opinions of TIFF. You should not treat any opinions expressed by Brendon as a specific endorsement to make a particular investment. References to any securities are for informational purposes only and do not constitute an investment recommendation or offer to provide investment advisory services. Any past performance discussed is not indicative of future results. Please keep in mind that investment in a fund entails a high degree of risk, including the risk of loss. Please note that the ads featured in this podcast are not endorsed by TIFF, and TIFF is not a sponsor of these ads.
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Highlights:
TIFF’s Mission: How TIFF Investment Management supports nonprofits with specialized investment solutions.
Private Markets Expertise: Insights into early-stage venture capital, lower middle market buyout, and growth equity investments.
Partnership Approach: How TIFF collaborates with nonprofits of various sizes to customize portfolios and deliver long-term returns.
Legacy of Leadership: The influence of David Swensen, former Yale CIO, on TIFF’s investment philosophy.
Risk Management: Strategies for balancing risk and reward in complex market environments.
Career Insights: Lessons from Brendon’s journey in private equity and investment management.
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Guest Bio:
Brendon Parry is the Head of Private Markets, Deputy CIO, and Managing Director at TIFF Investment Management. He has been with TIFF since 2011, leading the firm's private markets initiatives with a focus on early-stage venture capital, lower middle market buyout, and growth equity. Before TIFF, Brendon worked at Providence Equity Partners and Cambridge Associates. He holds an AB in Economics from Brown University and an MBA from Harvard Business School. With a passion for helping nonprofits achieve their financial goals, Brendon plays a key role in TIFF’s mission.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
We’d like to thank @Carta for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Sponsor:
At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: carta.com/howiinvest.
--
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Brendon Parry: https://www.linkedin.com/in/brendon-parry-77a5677/
Links:
TIFF Investment Management: https://www.tiff.org/private-markets/
--
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(2:06) TIFF's mission and partnership with foundations
(4:01) TIFF's investment strategies with a focus on private markets
(7:01) Reasons for focusing on lower middle market and early stage VC
(9:02) Sponsor: Tactic by Carta
(10:09) Risk assessment in lower middle market PE vs. larger PE
(23:11) Historical performance comparison: fund ones vs. fund twos
(24:42) Diligence process for independent sponsors
(27:01) Coordinating sponsor and deal diligence teams
(27:37) Organizational changes and lessons from 14 years at TIFF
(32:05) Building an antifragile portfolio and the confidence paradox in investing
(37:31) Predicting the future and core principles in manager selection
(41:35) Closing remarks
...more
42min
March 18, 2025 E147: Inside the Mind of a $2.4 Billion Investor w/Charlotte Zhang
In this episode of How I Invest, I dive deep into a conversation with Charlotte Zhang of Inatai Foundation. Charlotte shares her approach to managing a $2.4 billion private investment program, the importance of market inefficiencies, and how she strategically builds GP relationships. We explore how Inatai identifies top managers, why LPs are increasingly interested in fundless sponsors, and what makes a great investment philosophy. Whether you're an LP, VC, or just curious about institutional investing, this episode is packed with insights on capital allocation, conviction-based investing, and long-term partnership building.
Highlights:
Building a $2.4 Billion Investment Program: How Charlotte structured Inatai’s approach without rigid asset allocation targets.
GP Selection Strategy: The four P’s—People, Philosophy, Process, and Performance—that guide investment decisions.
Market Inefficiencies & Innovation: Why Inatai prioritizes global opportunities in venture, buyout, and select real assets.
Fundless Sponsors: Why LPs are increasingly backing fundless sponsors and the advantages of doing so.
Investment Discipline: How to evaluate managers over time and avoid the pitfalls of FOMO-driven investing.
Handling Market Downturns: The characteristics of managers who thrive in turbulent markets.
The Role of LPs as Value-Added Partners: How LPs can help GPs beyond just providing capital.
Diversification vs. Concentration: How Inatai balances a high-conviction portfolio while maintaining risk-adjusted returns.
The Future of Inatai: How the foundation is expanding its impact through its outsourced CIO platform.
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Guest Bio:
Charlotte Zhang is a Senior Portfolio Manager at Inatai Foundation, where she leads private investments within the $2.4 billion portfolio. She has previously held roles at Medley Partners and Iconiq Capital, developing expertise in manager selection, portfolio construction, and market inefficiencies. Charlotte is passionate about long-term investing, identifying top-tier GPs, and fostering meaningful LP-GP relationships.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Charlotte Zhang:https://www.linkedin.com/in/charlotterzhang/
Links:
Inatai Foundation: https://inatai.org/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(1:20) Creating and executing a lower middle market PE strategy
(3:39) Spending years on investment decisions and handling market downturns
(8:08) Exploring interest in fundless sponsors and largest deals
(11:09) Inatay team structure and the generalist team approach
(13:17) Managing infinite opportunities and diversification strategies
(16:38) Sourcing and adding value to GP relationships
(21:30) Closing remarks
...more
23min
March 14, 2025 E146: The 92% AI Failure: Unmasking Enterprise's Trillion-Dollar Mistake
In this episode of How I Invest, I sit down with Matt Fitzpatrick, CEO of Invisible Technologies and former head of McKinsey’s QuantumBlack Labs. Matt shares his deep insights on enterprise AI adoption, model fine-tuning, and the challenges businesses face when integrating AI into their workflows. We explore why only 8% of AI models make it to production, how enterprises can overcome friction points, and the future of AI-powered enterprise solutions. If you’re curious about the intersection of AI and business strategy, this episode is a must-listen.
Highlights:
Enterprise AI Adoption: Why only 8% of AI models reach production and how companies can improve their success rates.
AI Fine-Tuning for Enterprises: The importance of domain-specific AI models and why general AI solutions don’t always fit enterprise needs.
The Data Challenge: Why poor data quality is the biggest barrier to AI adoption and how companies can fix it.
Human-AI Collaboration: The role of human feedback in training AI models for enterprise use cases.
Real-World AI Success Stories: How companies like Moody’s and Klarna successfully implemented AI solutions.
Invisible Technologies’ Vision: How Invisible is building an AI-powered enterprise services platform to modernize business operations.
Future of AI in Business: How AI-native companies will rethink workflows and software applications from the ground up.
Matt’s Journey: From leading McKinsey’s AI lab to scaling one of the fastest-growing AI companies.
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Guest Bio:
Matt Fitzpatrick is the CEO of Invisible Technologies, a rapidly growing AI-powered services company. Before joining Invisible, Matt led McKinsey’s QuantumBlack Labs, where he worked on large-scale AI and data transformation projects. He has extensive experience in enterprise AI adoption and has helped some of the world’s largest organizations modernize their operations using artificial intelligence.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
We’d like to thank @Carta and @Daloopa for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Sponsor:
At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/howiinvest.
Sponsor:
Daloopa uses AI to provide the best fundamental data service for equity analysts globally. Daloopa empowers users to automatically update existing models and expedite new model builds so that users can spend more time on insights and ideas. Accurate data is central to all investment decisions and can influence speed and confidence for decision-makers. Daloopa believes that AI technology can improve clarity and efficiency for investors and financial markets. Learn more at: www.daloopa.com/how.
--
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Matt Fitzpatrick: https://www.linkedin.com/in/matthew-fitzpatrick-97b62722/
Links:
Invisible Technologies: https://www.invisible.co/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(1:46) Training vectors and core business components of Invisible Technologies
(3:21) Successful enterprise models and future AI evolution
(5:07) Challenges and evaluation of AI model deployment at scale
(7:49) Human feedback and accuracy requirements in AI models
(10:03) Fine-tuning AI models for enterprise applications
(12:27) McKinsey's successful enterprise AI use cases
(13:23) AI's impact on productivity and process redesign
(15:39) Invisible Technologies' growth strategy and focus on enterprise fine-tuning
(17:22) Building a modern ServiceNow with GenAI and avoiding obsolescence
(18:26) Modernization of legacy systems and AI native application development
(20:03) Shifting focus in the AI ecosystem and agentic layer
(22:30) Comparing AI native CRM to traditional CRM systems
(23:18) Invisible Technologies' future vision and optimism about enterprise AI
(24:33) Closing remarks
...more
26min
March 11, 2025 E145: Is a 35% IRR Really Achievable? Exploring Search Fund Returns
In this episode of How I Invest, I interview Robert Cherun, an expert in search funds and small-cap investing. Robert shares his journey from launching his own search fund to building and exiting a highly successful business. We dive into the fundamentals of search funds, the economics of acquiring and scaling small businesses, and the key traits that make a successful searcher.
Highlights:
What Is a Search Fund? How search funds enable entrepreneurs to acquire and grow established businesses with investor backing.
Impressive Returns: Search funds have historically generated 35% net IRRs and 4.5x ROI, making them a compelling investment strategy.
Barriers to Institutional Adoption: Despite high returns, institutional investors struggle to deploy capital effectively in this micro-cap space.
Search Fund Lifecycle: A breakdown of how searchers raise capital, find businesses, and structure acquisitions.
Portfolio Strategy: How Robert constructs a diversified portfolio of search fund investments to maximize returns.
TAM & Growth of Search Funds: How the space has evolved from niche to mainstream, with billions invested in recent years.
Traits of a Successful Searcher: The skills and qualities investors look for in entrepreneurs, from financial acumen to leadership ability.
Lessons from a $150M Exit: Robert’s journey from acquiring a $5M security business to scaling it into an industry leader with 2,000 employees.
The Asurion Story: A legendary search fund deal that delivered 100x–1,000x returns to early investors.
Search Funds vs. Startups: Why search funds offer a lower-risk path to entrepreneurship compared to venture-backed startups.
Co-CEO Model: Best practices for managing leadership dynamics and decision-making between business partners.
Governance & Investor Relations: How search fund investors maintain oversight while giving CEOs operational control.
Biggest Misconceptions About Search Funds: Why experience isn’t everything and how young entrepreneurs can successfully run businesses.
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Guest Bio:
Robert Cherun is a leading investor in search funds and small-cap businesses. As the co-founder of a successful security company, he scaled the business from $5M to $150M in revenue before exiting to a strategic buyer. Now, through his firm Legate Partners, Robert invests in and mentors the next generation of search fund entrepreneurs. Passionate about small business transformation, Robert specializes in identifying high-potential searchers and helping them build industry-leading companies.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email me at [email protected].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Robert Cherun: https://www.linkedin.com/in/robcherun/
Links:
Legate Partners: https://www.legatelp.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(0:51) Overview of search funds and historical returns
(2:16) Capitalization and portfolio construction in search funds
(3:26) Growth of search funds and searcher profiles
(5:05) Comparing search funds with traditional startup models
(7:37) UCIT Online Security acquisition journey and deal economics
(10:22) Famous search fund deals and Legate Partners introduction
(11:33) Legate Partners' strategy and CEO selection criteria
(13:24) CEO profiles and co-CEO best practices
(15:55) Governance and decision-making in search funds
(17:44) Insights on search fund dynamics and governance
(19:11) Transitioning from finance to search funds and key lessons
(20:11) Final thoughts on team dynamics and search fund misconceptions
(20:58) Closing remarks
...more
22min
March 09, 2025 E144: How the World’s Top Investors Compound Their Advantages
In this special solo episode of How I Invest, I break down one of the most powerful forces in investing: compounding. Over the course of 142 episodes, I’ve discovered that the best investors all leverage compounding—not just in their portfolios but in every aspect of their business. From relationships and reputation to proprietary information and top talent, compounding creates exponential advantages in a hyper-competitive market.
Highlights:
Compounding Beyond Capital: The biggest investors understand that everything compounds, including reputation, diligence, and deal-making experience.
The Power of Relationships: Trust compounds with each deal, leading to faster and more efficient decision-making.
Reputation as an Asset: Warren Buffett’s ability to negotiate superior terms stems from his compounding reputation as an ethical and skilled investor.
Proprietary Information Loops: Access to unique insights leads to better investments, which generate even more privileged information.
People as a Compounding Advantage: The best organizations attract and retain A-players, who in turn recruit other top talent, creating a self-reinforcing cycle of excellence.
The Arbitrage of A-Players: Paying A-players above market rates is a competitive advantage, as they generate exponentially greater value.
--
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(0:21) The role of compounding in investing and relationships
(2:13) Trust bias, deal-making efficiency, and reputation effects
(4:23) Proprietary information and the compounding of talent
(6:50) AI's impact on productivity and compounding
(7:49) Closing remarks
...more
9min
March 07, 2025 E143: From Fame to Fortune: How Celebrities Turn Fame into Billion-Dollar Brands
In this episode of How I Invest, I interview Scott van den Berg, an expert in celebrity-founded brands and the managing partner of Hotstar VC. Scott shares deep insights into how celebrities are leveraging their platforms to build billion-dollar businesses and why some partnerships thrive while others fail. We discuss the shift in celebrity investments, the rise of creator-led brands, and key lessons from success stories like Ryan Reynolds' Mint Mobile, Kim Kardashian's Skims, and George Clooney's Casamigos.
Highlights:
Lessons from Ryan Reynolds: How he strategically invested in "unsexy" industries and built massive brand value.
The Power of Celebrity-Led Brands: How stars like Kim Kardashian, Logan Paul, and Ryan Reynolds built billion-dollar companies.
Equity vs. Cash Deals: Why traditional talent managers prefer cash over equity and how this impacts startup partnerships.
Product-First Approach: The importance of having a strong product, even when backed by a celebrity.
Celebrity Product-Market Fit: Why aligning a celebrity's brand with the right product is crucial for success.
The Over saturation of Celebrity Tequila Brands: Why so many celebrities enter the liquor market and the real economics behind it.
The Rise of the Creator Economy: How influencers are turning their massive audiences into thriving businesses.
Avoiding Common Pitfalls: The biggest mistakes startups make when partnering with celebrities.
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Guest Bio:
Scott van den Berg is the managing partner at Hotstar VC, a fund specializing in investments in celebrity and creator-led brands. With experience in 55 celebrity-founded businesses, Scott has worked with stars like Selena Gomez, DJ Khaled, and Jake Paul. His team includes co-founders of some of the most successful celebrity-led brands, such as The Honest Company and Feastables. As a thought leader in the space, Scott shares insights on how celebrities can build sustainable businesses and transform their influence into long-term value.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
We’d like to thank @Carta and @Daloopa for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #AssetManagement
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Sponsor:
At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/howiinvest.
Sponsor:
Daloopa uses AI to provide the best fundamental data service for equity analysts globally. Daloopa empowers users to automatically update existing models and expedite new model builds so that users can spend more time on insights and ideas. Accurate data is central to all investment decisions and can influence speed and confidence for decision-makers. Daloopa believes that AI technology can improve clarity and efficiency for investors and financial markets. Learn more at: www.daloopa.com/how.
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Stay Connected: X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Scott Van den Berg: https://www.linkedin.com/in/scott-van-den-berg-22b534150/
--
Links:
HotStar VC: https://www.hotstart.vc/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(5:01) Sponsor: Tactic Bicarda
(6:20) Selecting and partnering with the right celebrity for a brand
(9:09) Sponsor: The Loop
(10:13) Navigating challenges with celebrity managers and agencies
(13:10) Hotstar VC's methodology in celebrity-founded brand investments
(16:43) Case studies of celebrity brand successes
(18:31) Key takeaways from investing in celebrity-driven ventures
(19:22) Closing remarks and upcoming episode teaser
(20:15) Sponsor: Vanguard
(23:45) Closing remarks
...more
20min

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