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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:
    E133: Lessons from Investing in 2200 Startups (in 23 Minutes) Jan 28, 2025
    Show notes

    In this episode of How I Invest, I connect with Lorenzo Thione, Managing Director at Gaingels, one of the most active and inclusive venture syndicates in the world. Lorenzo discusses his philosophy on diversity, equity, and inclusion (DEI), the democratization of venture capital, and his thoughts on the AI revolution. From his experience building a portfolio of over 100 investments to lessons learned from co-founding PowerSet, Lorenzo provides invaluable insights for investors and entrepreneurs alike.

    Highlights: Philosophy on DEI: How the distribution of talent and opportunity shapes Gaingels' mission to bring inclusivity to venture capital.

    Gaingels’ Approach: Investing in companies that prioritize diversity in talent, governance, and capital while enabling LPs to invest with as little as $1,000.

    Venture Allocation: Advice for high-net-worth investors on diversifying their portfolios across stages, sectors, and liquidity horizons.

    Lessons from Uber: Why Lorenzo passed on the Uber seed round and how it shaped his investment philosophy.

    AI Investing: Insights into the evolution of AI, the importance of category-defining opportunities, and the impact of recent major investments in AI infrastructure.

    Angel Investing: The importance of backing founders you know and trust, and how personal relationships can lead to better investment outcomes.

    --

    Guest Bio: Lorenzo Thione is a serial entrepreneur, investor, and expert in Artificial Intelligence. Currently, as Managing Director of Gaingels, he leads investments in AI, deep-tech, and consumer tech, promoting diversity in venture capital. He co-founded Powerset, an AI-driven search engine acquired by Microsoft and integrated into Bing. Beyond technology, Lorenzo is a celebrated Broadway producer, with productions like "Hadestown" and "The Inheritance," earning multiple Tony Awards. He also co-founded StartOut, supporting LGBTQ+ entrepreneurs. Born in Milan, he holds an M.S. in Computer Engineering from the University of Texas at Austin.

    Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Lorenzo Thione: https://www.linkedin.com/in/lorenzothione/

    Links: Gaingels: https://www.gaingels.com/

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

    (0:00) Episode preview (2:52) Gaingels syndicate and low minimum LP investment strategy (5:15) Venture capital allocation advice for high net worth individuals (6:19) Diversification strategies within venture capital (8:37) Analyzing long-term venture capital returns (9:52) Gaingels investing access and strategic insights (13:03) Key lessons from early-stage angel investing experiences (16:56) Investing in AI and portfolio strategy considerations (19:37) SoftBank and Sam Altman's AI investment impact (23:29) Closing remarks

    E132: How Nichole Wischoff Raised a $50M Fund in 5 Months Jan 24, 2025
    Show notes

    In this episode of How I Invest, I dive into a conversation with Nichole Wischoff, Founder and Managing Partner at Wischoff Ventures, to explore her remarkable journey of raising a $50 million fund during one of the toughest markets of 2024. Nichole shares her insights on fundraising strategies, the power of media in deal sourcing, and building a personal brand. She also discusses her unique approach to fostering relationships in venture capital and why community and authenticity are key drivers of success in this space. This episode is packed with actionable takeaways for emerging fund managers and anyone navigating the world of VC.

    Highlights: $50 Million Fundraise: How Nichole secured her fund’s anchor and achieved a first close in just two months.

    Building Distribution Advantage: Leveraging social media and brand-building to access top founders and close deals.

    Fund Size Challenges: Overcoming objections from institutional LPs and proving scalability.

    Strategic Fundraising: Nichole's timeline, drip campaigns, and tactics to convert LPs at a 26% rate.

    Community-Driven Success: The value of collaboration among emerging managers and fostering trusted relationships.

    The Twitter Advantage: Nichole’s journey to building a massive online following and using it as a competitive edge.

    Cringe Scales: Why embracing discomfort on social media pays dividends for fund managers.

    Future Focus: Nichole’s advice for navigating relationships, building a firm, and standing out in the VC world.

    --

    Guest Bio: Nichole Wischoff is the Founder and Managing Partner of Wischoff Ventures, a venture capital firm investing in early-stage startups. With deep operational experience at multiple high-growth companies and a proven track record in venture capital, Nichole has built her reputation as a leader in the emerging manager space. Known for her authenticity and strategic approach, she is passionate about building her firm and brand in public while supporting the next wave of groundbreaking founders.

    Our podcast now receives more than 200,000 downloads a month. Interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

    We’d like to thank @ReedSmith for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP

    --

    SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd Nichole Wischoff: @NWischoff

    LinkedIn: David Weisburd: David Weisburd LinkedIn Nichole Wischoff: Nichole Wischoff LinkedIn

    Links: Wischoff Ventures: www.wischoff.com

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

    (0:00) Episode preview (2:08) Leveraging social media and brand for distribution advantage (4:31) Overcoming LP objections and scaling investments (6:49) Strategies for first close and securing anchor LPs (10:29) Identifying and engaging interested LPs (13:34) Insights into decision-making of top quartile LPs and endowments (15:52) Collaborating with emerging managers and building trust (19:43) Importance of the 80/20 rule in relationships (21:27) Strategies for building a Twitter presence and follower psychology (25:47) Tips for effective Twitter engagement and brand growth (28:28) Closing remarks

    E131: Can VCs Make Money in Deep Tech? w/Nick Shekerdemian Jan 21, 2025
    Show notes

    In this episode of How I Invest, I sit down with Nick Shekerdemian, entrepreneur, investor, and founding partner of The Venture Collective (TVC). A former Oxford student turned Thiel Fellow, Nick shares his journey of dropping out of university to pursue big ideas and how the fellowship helped shape his path in venture capital. We explore TVC's unique approach to portfolio construction, investing in deep tech and computational biology, and why thesis-driven investing is the future of venture capital. Nick also discusses challenges like founder breakups, scaling value-added strategies, and his thoughts on the next big shifts in technology and bio-defense.

    Highlights: Thiel Fellowship: Why Nick left Oxford to join the fellowship and how it transformed his career.

    Portfolio Construction: TVC’s concentrated approach to seed-stage investing and leveraging informational advantages to support founders.

    Thesis-Driven Investing: Why Nick believes the future of venture capital lies in backing big, transformative ideas, especially in deep tech, computational biology, and AI.

    Bio-Defense and Innovation: How advancements in AI and biology could revolutionize healthcare and address emerging bio-defense challenges.

    Supporting Founders: The importance of transparency, setting micro-goals, and building trust for navigating challenges like founder breakups.

    Opportunities in Deep Tech: Exploring transformative sectors like defense tech, healthcare personalization, and reindustrialization driven by sustainability and AI.

    Shifts in Venture Capital: Nick’s prediction that rapid innovation will redefine the venture landscape in the next few years.

    --

    Guest Bio: Nick Shekerdemian is the founding partner of The Venture Collective (TVC), a seed-stage investment firm focused on backing visionary founders tackling transformative problems. A former Thiel Fellow, Nick has built his career at the intersection of entrepreneurship and venture capital, with a deep passion for investing in ambitious ideas in deep tech, healthcare, and sustainability. He’s committed to supporting founders who think differently and aren’t afraid to challenge the status quo.

    Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    --

    Stay Connected: Twitter: David Weisburd: @dweisburd

    LinkedIn: David Weisburd: linkedin.com/in/dweisburd/ Nick Shekerdemian: https://www.linkedin.com/in/nshekerdemian/

    Links The Venture Collective: https://theventurecollective.com

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

    (0:00) Episode preview (1:10) Dropping out of Oxford and Thiel Fellowship Insights (4:01) Seed Stage Startup Portfolio Construction (5:58) Leveraging Informational Advantages (8:33) Scaling Value-Added Strategies for Startups (10:28) Reporting Cadence vs. Company Performance (11:42) Fostering Transparency with Founders (14:17) TVC's Alpha Sources and Thematic Investing (18:28) Deep Tech Investments and Defense Tech Excitement (20:02) Changing LP Sentiments and Non-Momentum Investing (22:40) Computational Biology as an Investment Opportunity (24:50) Contrarian Views on Venture Capital (26:15) The Future of Biodefense and Bioweapons (27:46) Call to Action for Problem Solvers (28:34) Closing remarks

    E130: CalPERS CEO Marcie Frost on the Future of the $500 Billion Pension Fund Jan 17, 2025
    Show notes

    In this episode of How I Invest, I sit down with Marcie Frost, CEO of CalPERS, the largest public pension fund in the United States. From her beginnings in public service to leading a $502.9 billion portfolio, Marcie shares her journey and offers insights into managing one of the most influential pension funds globally. We discuss the challenges of governance, integrating climate change risks into investment decisions, and the importance of building a culture of trust and innovation. Marcie also delves into CalPERS’ strategic focus on sustainable investments, diversity, equity, and inclusion initiatives, and how the organization is setting benchmarks in transparency and fiduciary responsibility.

    Highlights: Public Service Journey: Marcie’s transition from Washington state's Department of Retirement Systems to leading the largest public pension fund in the U.S.

    CalPERS’ Mission: The role of a $502.9 billion portfolio in securing the financial future of over 2 million California public sector workers and their families.

    Strategic Asset Allocation: How CalPERS utilizes its Asset Liability Management process to inform asset allocation decisions and set investment return assumptions.

    Integrating Climate Risks: The incorporation of climate change risks into investment decisions across all asset classes and the launch of a $100 billion sustainable investment strategy aimed at reducing carbon emissions intensity by 50% by 2030.

    Building a Culture of Trust: Marcie’s approach to fostering an inclusive culture through the development of CalPERS' first Diversity, Equity & Inclusion framework.

    Sustainable Investments: CalPERS' commitment to sustainable investing, including its role as a founding member of Climate Action 100+, an initiative with 700 signatories and $68 trillion in assets under management.

    Stakeholder Engagement: Expansion of stakeholder outreach to ensure all parties are informed and have a voice in the system's future.

    Advocacy for Defined Benefits: Marcie's belief in providing equitable and affordable health care and retirement options for public employees.

    --

    Guest Bio: Marcie Frost is the Chief Executive Officer of CalPERS, overseeing the largest public pension fund in the United States. With over 30 years of experience in public service, Marcie is a dedicated advocate for financial security, transparency, and sustainability. Under her leadership, CalPERS has advanced its goals in asset management, stakeholder engagement, and cultural transformation, ensuring that its over 2 million members can retire with dignity.

    Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

    We’d like to thank @ReedSmith for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    --

    Sponsor: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Marcie Frost: https://www.linkedin.com/in/marcie-frost-56a30a281/

    Links:

    CalPERS: https://www.calpers.ca.gov/

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

    (0:00) Episode preview (0:35) CalPERS' strategic asset allocation, risk limits, and board dynamics (2:39) Composition, election, and decision-making of CalPERS' investment committee (5:25) Understanding board members' risk appetite and stakeholder engagement (9:07) Navigating political aspects and role differentiation at CalPERS (14:02) Changing organizational culture and focusing on investment results (18:29) Sponsor: Reed Smith (21:22) Managing media scrutiny and its impact on investment decisions (22:36) Stability and importance of the CIO role at CalPERS (23:13) Emerging managers, diversity, and strategic planning for 2025-2029 (24:55) Evaluating private markets, liquidity premium, and active vs passive management (27:47) Building relationships as a first call partner to managers (29:43) CEO reflections and fostering a world class culture at CalPERS (31:27) Key takeaways about CalPERS for listeners (34:38) Closing remarks

    E129: The Number #1 Predictor of Startup Success w/Ken Smythe Jan 14, 2025
    Show notes

    In this episode of How I Invest, I connect with Ken Smythe, founder of Next Round Capital, to discuss his journey in private markets, lessons from hedge fund management, and the future of thematic investing. Ken shares insightful stories about spotting talent, using key executive moves as signals for investment opportunities, and the rise of AI and defense technology. We also explore the challenges facing venture capital and private equity in today’s market, including liquidity bottlenecks and the hunt for alpha in a rapidly evolving landscape. Ken's personal story of resilience and his passion for innovation shine through in this inspiring conversation.

    Highlights: Key Signals in Early-Stage Investing: Why tracking executive moves from established companies like Apple or Stripe to startups can offer a major edge in spotting emerging opportunities.

    AI's Evolution: The current state of AI innovation compared to the early days of the internet and the need for sustainable business models to monetize AI advancements.

    Defense Tech: How startups are disrupting traditional players like Lockheed Martin and General Dynamics with cutting-edge technologies tailored to modern battlefields.

    Hedge Fund Insights: The importance of diversification, risk management, and identifying specialized talent in building successful multi-strategy hedge funds.

    Secondary Markets: The growing role of VCs, family offices, and retail investors in accessing shares of companies like SpaceX and how liquidity challenges are reshaping private equity strategies.

    Thematic Investing: From AI chatbot agents to defense technology, Ken outlines the trends and themes that he believes will dominate in 2025 and beyond.

    Personal Resilience: Ken’s inspiring journey of launching his own firm amid personal challenges, underscoring the importance of seizing opportunities and living with purpose.

    --

    Guest Bio: Ken is the founder of Next Round Capital, a firm specializing in secondary investments, co-investments, and niche opportunities in technology and AI. With a background in hedge fund management and a focus on thematic investing, Ken leverages his deep network and expertise to identify groundbreaking opportunities in private markets. He is passionate about innovation and building meaningful relationships in the venture ecosystem.

    Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

    #VentureCapital #VC #Startups #OpenLP

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Ken Smythe: https://www.linkedin.com/in/ken-smythe/

    Links: Next Round Capital: https://www.nextroundcapital.com

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

    (0:00) Episode preview (1:37) Key Executive Movements in Tech (3:38) Adverse Selection in Venture Capital (4:35) Investment Trends for 2025 (6:27) Focus on Defense Technology Investments (8:06) Managing Liquidity in Venture Portfolios (10:36) Analyzing SpaceX's Investment Potential (11:45) Hedge Fund Insights from a $5 Billion Experience (14:37) Strategies for Recruiting and Evaluating Portfolio Managers (24:50) The Art of Referencing and Backchanneling (26:01) Spotlight on Next Round Capital (27:39) AI Investment Landscape Analysis (28:34) Business Model Significance in Tech Sector (29:52) Closing remarks

    E128: iCapital CEO Lawrence Calcano on the New $145 Trillion Entering Private Markets Jan 10, 2025
    Show notes

    In this episode of How I Invest, I sit down with Lawrence Calcano, Chairman and CEO of iCapital, to explore the transformative potential of alternative investments in the wealth management space. Lawrence shares his journey from Goldman Sachs to building iCapital, a platform managing over $200 billion in alternative assets. We dive deep into the challenges and opportunities in democratizing access to private markets, the role of technology in scaling the alternatives industry, and the growing appetite for private equity and credit among high-net-worth investors. If you're curious about the future of wealth management and the intersection of technology and alternatives, this episode is a must-listen.

    Highlights: The Wealth Market's Untapped Potential: Retail investors collectively control $145 trillion globally, rivaling institutional markets.

    Democratizing Alternatives: iCapital enables financial advisors to access institutional-quality alternative products and simplifies operational complexities with technology.

    Trends in High-Net-Worth Investing: A shift back to equities in 2025 following a credit-dominated two years.

    Illiquidity as a Feature, Not a Bug: How private markets generate alpha through active management during illiquidity periods.

    Overcoming the Chicken-and-Egg Problem: Building trust with both advisors and general partners to grow the platform.

    Technology as a Game Changer: AI, distributed ledgers, and automation reduce inefficiencies and errors in managing private fund investments.

    Future of Alternatives: Allocations to alternatives are expected to grow significantly as education and access improve.

    Key Lessons in Investing: Lawrence emphasizes the importance of understanding investments fully to navigate market dynamics effectively.

    Building a Cohesive Culture: Insights on leadership, teamwork, and fostering a shared mission at iCapital.

    --

    Guest Bio: Lawrence Calcano is the Chairman and CEO of iCapital, a leading platform providing access to alternative investments for wealth advisors and their clients. With a background in tech investment banking at Goldman Sachs, Lawrence has been instrumental in modernizing how advisors and high-net-worth individuals access and manage private market investments.

    Our podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

    We’d like to thank @ReedSmith for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    --

    SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships, and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Lawrence Calcano: https://www.linkedin.com/in/lawrence-calcano-5b8b9111/

    Links: iCapital: https://icapitalnetwork.com/

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

    (0:00) Episode preview (1:14) I Capital's founding and evolution from Goldman Sachs (2:37) Private equity's wealth channel strategy and challenges (4:56) Comparing high net worth and institutional investors (7:31) Investor trends: From credit to equity interests (10:27) Projections for the future of the alternatives industry (14:45) Wealth channels' impact on adverse selection (15:23) Sponsor: Reed Smith (19:28) I Capital's aggregation service for General Partners (GPs) (20:32) The enduring nature of the wealth channel (22:16) The role of emerging managers in the wealth channel (26:00) Lawrence Calcano's investment philosophy and early lessons (27:40) The significance of investment comprehension (28:03) Fostering and maintaining iCapital's company culture (30:39) Scaling company values with organizational growth (32:31) iCapital's ambitious vision for 2030 (33:22) Addressing challenges in the alternatives sector (34:43) Leveraging technology to solve client problems (37:11) Implications of the accredited investor rule (38:46) Closing remarks

    E127: Interview with CEO of Top AI Company Backed by Founders Fund and Khosla Ventures Jan 07, 2025
    Show notes

    In this episode of How I Invest, I sit down with Felix Ejeckam, Co-Founder and CEO of Akash Systems. Felix discusses how Akash is leveraging synthetic diamond technology to revolutionize cooling for high-power microchips used in AI servers and satellite communications. He shares insights on their $68 million CHIPS Act funding, the importance of U.S. semiconductor manufacturing, and Akash’s journey through tough times to becoming a leader in cutting-edge technology. A must-listen for anyone interested in semiconductors, AI, or transformative tech innovations.

    Highlights: What is Akash Systems? A company pioneering synthetic diamond cooling technology to enhance performance and efficiency in AI servers and satellite communications systems.

    Synthetic Diamond Technology: How Akash grows lab-made diamonds and integrates them into chips to reduce cooling costs and improve performance by up to 90%.

    Massive Market Opportunity: Targeting a $200-$400 billion market spanning data centers, satellite communications, EVs, smartphones, and defense systems.

    CHIPS Act Funding: Akash recently secured $68 million in CHIPS funding to scale manufacturing, establish a semiconductor fab in Oakland, and support U.S. economic and national security goals.

    Overcoming Tough Times: Reflecting on the challenges during COVID-19, Akash used the “quiet years” to refine its technology, expand into new markets like AI, and emerge stronger.

    Staying Non-Consensus: The importance of conviction, foresight into market trends, and building a team that balances optimism and pragmatism.

    What’s Next for Akash: Upcoming satellite launches, server shipments in Q1, and a trajectory to becoming the leading high-end AI server company globally.

    --

    Guest Bio: Felix Ejeckam is the Co-Founder and CEO of Akash Systems, a trailblazing company using synthetic diamond technology to transform semiconductor cooling and performance. Under Felix’s leadership, Akash has achieved groundbreaking innovations in AI servers and satellite communications systems, contributing to U.S. manufacturing and technological independence. Felix is passionate about fostering innovation and building resilient companies that thrive in challenging times.

    Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd Felix Ejeckam: @felixejeckam

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Felix Ejeckam: https://www.linkedin.com/in/felixejeckam/

    Links: Akash Systems: https://www.akashsystems.com/

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

    (0:00) Episode preview (2:08) Akash Systems and the cost of cooling server chips (4:05) Chips Act funding (7:13) Competitive landscape in AI server market (11:33) US election impact on Akash Systems (12:39) Overcoming COVID-19 challenges (14:32) Building resilience and strategic pivots (19:30) Non-consensus investing strategies (22:38) Closing remarks

    E126: How much Bitcoin should Institutional Investors hold? w/CIO of Bitwise Jan 03, 2025
    Show notes

    In this episode of How I Invest, I connect with Matt Hougan, Chief Investment Officer at Bitwise Asset Management. Matt shares his expertise on Bitcoin and cryptocurrency investments, offering actionable insights on portfolio allocation, valuation, and the evolving crypto market. From the benefits of a 2–5% Bitcoin allocation to the potential of Bitcoin as a global settlement currency, Matt provides a compelling case for crypto as a transformative asset class. This episode is a must-listen for institutional investors, financial advisors, and anyone curious about the future of digital assets.

    Highlights:

    Bitcoin Allocation: Why institutional investors should allocate at least 2% to Bitcoin to stay neutral with benchmarks and up to 5% to maximize risk-adjusted returns.

    Portfolio Benefits: Adding Bitcoin improves Sharpe ratios due to its low correlation with traditional assets, offering higher returns with minimal additional volatility.

    The Importance of Timeframe: Bitcoin’s performance as a hedge improves over a long-term horizon, despite short-term volatility.

    Behavioral Risk: The biggest risk in crypto investing is behavioral, emphasizing the importance of maintaining balanced portfolio allocations.

    Beyond Bitcoin: The case for diversifying into other cryptocurrencies like Ethereum, and the advantages of buying a basket of assets versus picking individual winners.

    Crypto Cycles: Why crypto markets are highly cyclical due to their early-stage nature and speculative tendencies, and how this volatility is decreasing over time.

    Regulatory Clarity: How a pro-crypto regulatory environment under the new U.S. administration could unleash institutional investment and entrepreneurial growth in the crypto space.

    Bitcoin Valuation: Using supply-demand dynamics and gold’s $18 trillion market as a benchmark, Matt explains why Bitcoin could eventually reach $1 million per coin.

    Bitcoin as a Settlement Currency: The potential for Bitcoin to become a non-political settlement currency in a multipolar world.

    --

    Guest Bio: Matt Hougan is the Chief Investment Officer at Bitwise Asset Management, where he leads the development of innovative crypto investment strategies. A pioneer in crypto asset management, Matt created the first crypto index fund and has been guiding investors through the complexities of digital assets for over seven years. He’s known for his precise, academic approach to crypto and is passionate about helping investors understand the transformative potential of blockchain technology.

    Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

    We’d like to thank @ReedSmith for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP

    --

    SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd Matt Hougan: @Matt_Hougan

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Matt Hougan: https://www.linkedin.com/in/matthougan/

    Links: Bitwise Asset Management: https://www.bitwiseinvestments.com/

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

    (0:00) Episode preview (1:04) Institutional investment strategies in Bitcoin (4:35) Portfolio diversification with Bitcoin (8:13) Case study: MicroStrategy's Bitcoin strategy (10:03) Exploring other cryptocurrencies for institutional investors (12:45) Advantages of cryptocurrency baskets (14:38) Sponsor: Reed Smith (16:03) Cyclical nature of cryptocurrency markets (19:54) US government and Bitcoin investment prospects (21:42) Crypto's regulatory landscape under the Trump administration (25:40) Bitcoin's future beyond a store of value (27:21) Assessing Bitcoin's value without traditional cash flows (29:08) Bitwise investment strategy overview (30:17) Closing remarks

    E125: Co-CIO Alifia Doriwala on RockCreek’s $16 Billion Edge Dec 31, 2024
    Show notes

    In this episode of How I Invest, I sit down with Alifia Doriwala, Co-CIO and Managing Director at RockCreek, a multi-asset and OCIO solutions firm managing $16 billion in assets. Alifia delves into RockCreek’s unique approach to managing customized portfolios for endowments, foundations, and pensions. She shares her perspectives on navigating public and private markets, the evolving role of hedge funds, and the outlook for IPOs and M&A activity in 2025. This conversation is packed with insights for asset managers, institutional investors, and anyone seeking a deeper understanding of market trends and investment strategies.

    Highlights:

    What is RockCreek? A multi-asset and OCIO firm managing portfolios for clients with under $2 billion in AUM, combining private and public market expertise.

    Customized Solutions: Tailoring portfolios to meet client needs, including thematic private market investments like innovation in the aviation industry.

    Key Themes for 2025: Anticipating a rebound in IPO markets, increased M&A activity, and opportunities in healthcare and biotech within private markets.

    Public Markets Outlook: A shift toward active management as market dynamics broaden, with sector-specific opportunities in U.S. equities like energy, pharmaceuticals, and fintech.

    Private Markets Allocation: Targeting 20–30% in private equity and venture capital for long-term institutional investors, with 35–40% in alternatives when including real assets.

    Interest Rates and Inflation: Insights into the current rate environment and long-term concerns about inflationary pressures due to trade policies and tariffs.

    The Role of Hedge Funds: Understanding why institutions are increasing allocations to hedge funds for alpha and downside protection, and the contrasting strategies between discretionary and quant approaches.

    Lessons from a 20-Year Career: How starting in sales and trading shaped Alifia’s investment approach and the importance of being data-driven, dynamic, and open to new ideas.

    Continuous Improvement: Strategies for sharpening skills as a CIO, including constant learning, engaging with peers, and leveraging diverse macro perspectives.

    --

    Guest Bio:

    Alifia Doriwala is the Co-CIO and Managing Director at RockCreek, where she oversees multi-asset portfolios for institutional investors, including endowments, foundations, and pensions. With a career spanning over two decades, Alifia’s expertise bridges public and private markets, offering strategic solutions tailored to client needs. She is passionate about data-driven decision-making, market research, and mentoring the next generation of asset managers.

    Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    --

    Stay Connected:

    X / Twitter: David Weisburd: @dweisburd

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alifia Doriwala: https://www.linkedin.com/in/alifia-doriwala-4382629/

    Links: RockCreek: https://therockcreekgroup.com/

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

    (0:00) Episode preview (1:00) Solving client problems and investment themes for the new year (3:26) IPO market predictions and future interest rates (7:08) Alternatives portfolio strategies for endowments and foundations (11:53) Career insights: From sales and trading to investment management (13:30) Family offices' investment trends in hedge funds (16:27) Reflections and advice for aspiring CIOs (17:32) Closing remarks

    E124: Is Venture Capital Entirely Based on Luck? University of Chicago and Oxford Study Dec 27, 2024
    Show notes

    In this episode of the How I Invest Podcast, I interview David Clark, CIO of Vencap, to discuss the venture capital landscape. We discuss assumptions about small vs. large venture funds, unpack survivorship bias in performance data, and explore the power law dynamics in early-stage and growth funds. David Clark shares Vencap's strategy for identifying top-performing managers, insights on fund size limits, and the implications of political and economic shifts on venture capital. A must-listen for investors seeking a data-driven perspective on navigating the venture ecosystem.

    Highlights:

    Myth of Small Fund Outperformance: David Clark challenges the belief that smaller venture funds consistently outperform larger ones, noting limitations in available data and survivorship bias.

    Survivorship Bias in VC Data: Many underperforming funds don't report their results, skewing datasets like PitchBook and Cambridge. Clark highlights Carta as a potential unbiased source for small fund performance data.

    Power Law Dynamics in Venture Capital: Vencap's data shows that even growth funds exhibit power law outcomes, with 1.6% of their investments being fund returners—higher than early-stage funds (1%).

    Focus on Top-Performing Managers: Over 90% of Vencap's capital goes to 12-13 managers who have a track record of consistently backing fund-returning companies.

    Venture vs. Private Equity: Venture funds show stronger persistence of returns compared to private equity, with top-quartile funds often repeating their success.

    Fund Size Considerations: Vencap evaluates whether fund sizes align with the ability to back companies that generate massive returns. Excessively large funds can dilute performance potential.

    State of Venture Post-2020 Election: While short-term political changes may influence sentiment, Clark emphasizes focusing on long-term relationships with top managers and founders.

    Valuation Practices in Venture: Skepticism over inflated venture fund valuations is warranted, but Clark sees signs that portfolios may now be undervalued.

    --

    Guest Bio: David Clark is the CIO of Vencap, a firm specializing in venture fund investments since the 1980s. With a data-driven approach, Vencap partners with top-performing venture managers to navigate the power law dynamics of venture capital. David’s insights are rooted in decades of data, challenging conventional wisdom and focusing on long-term outperformance in venture markets.

    Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

    We’d like to thank @ReedSmith for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

    --

    SPONSORS: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

    --

    Stay Connected: Twitter David Weisburd: @dweisburd David Clark: @DaveClark85

    LinkedIn David Weisburd: https://www.linkedin.com/in/dweisburd/ David Clark: https://www.linkedin.com/in/david-clark-6678b6b/

    Links VenCap: https://www.vencap.com/

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

    (0:00) Episode preview (3:38) Survivorship bias and its effects on venture capital (11:48) VenCap's investment strategy and return persistence (16:04) Key factors influencing founder choices of investors (16:25) Sponsor: Reed Smith (19:04) Relationship between fund size and performance (20:06) Venture market insights after the 2024 election (23:36) The interplay between startups and investor actions (25:28) What excites LPs about the venture asset class (26:46) Venture fund valuations and market concerns (27:16) The predictive power of TVPI and DPI in venture funds (29:03) Following David Clark online and data-driven investing (31:04) Closing remarks

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