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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How many episodes does How I Invest with David Weisburd have?

The podcast currently has 143 episodes available.

How I Invest with David Weisburd episodes:

February 21, 2025 E140: Hamilton Lane Co-CEO on the $950 Billion AUA Business
In this episode of How I Invest, I sit down with Erik Hirsch, Co-CEO of Hamilton Lane, a global leader in private market investing. Erik discusses the evolving landscape of private markets and the integration of digital tools like tokenization in investments. He dives into how private markets are becoming more accessible to retail investors and the future of asset management, with a focus on education and technology. From the role of RIAs and wirehouses to the impact of digital wallets and tokens, Erik provides deep insights into what’s next for investors at every level. If you're curious about the future of investment opportunities and how they will change by 2030, this episode is a must-listen.
Highlights:
Private Market Access: How tokenization is revolutionizing private market access for retail investors, making it easier and more efficient to buy into private funds.
The 2030 Vision: The future of investing where both retail and institutional investors can seamlessly manage public and private assets in one place.
Roadblocks and Education: How myths about private markets and a lack of education are slowing adoption, and why proper education is key to unlocking the future of investment.
The Role of RIAs: Why wealth advisors play a critical role in helping clients navigate these changes and how their education will be key to accelerating private market growth.
Adapting to Consumer Expectations: The difference in expectations between institutional and retail investors and how firms need to adjust to meet these demands, especially in terms of technology and accessibility.
Culture at Hamilton Lane: Erik shares how building and maintaining a strong company culture has been a key driver of Hamilton Lane’s success.
The Path to a Trillion Dollars AUM: What Hamilton Lane's growth trajectory looks like, and the future goals as they continue expanding globally.
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Guest Bio:
Erik Hirsch is the Co-CEO of Hamilton Lane, a leading private markets investment management firm. With over 30 years of experience, Erik has helped lead Hamilton Lane's growth into one of the largest players in the private market space. Based in Philadelphia, Erik's leadership has focused on innovation, diversification, and bringing private market opportunities to a broader range of investors. His commitment to education and customer-first culture has been instrumental in Hamilton Lane’s success.
Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
We’d like to thank @JuniperSquare and @ReedSmith for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Sponsor:
Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com.
--
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/
Erik Hirsch: https://www.linkedin.com/in/erik-hirsch-hamilton-lane/
Links:
Hamilton Lane: https://www.hamiltonlane.com/en-us
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(1:13) The fallacy of the 60/40 portfolio and institutional strategies
(3:54) Diversification strategies in private vs public assets
(7:42) Hamilton Lane's focus on the retail market
(8:07) Sponsor: Juniper Square
(10:32) Hamilton Lane's retail market targeting strategies
(13:43) Liquidity concerns for retail investors
(15:47) Tokenizing Hamilton Lane funds for accessibility
(18:52) Retail and institutional investment convergence vision
(20:01) Challenges in retail access to private markets
(23:06) Incentivizing RIAs to support private market investments
(23:29) Sponsor: Reed Smith
(24:48) Erik Hirsch's journey to co-CEO of Hamilton Lane
(25:54) Pros and cons of Hamilton Lane's Philadelphia location
(27:28) Career insights and underappreciated starting points
(28:31) Growth dynamics within Hamilton Lane
(29:26) Hamilton Lane's growth and trillion-dollar goal
(30:29) Closing remarks
...more
31min
February 18, 2025 E139: How HIG Went from $75 Million to $67 Billion AUM
In this episode of How I Invest, I engage with Jackson Craig, Managing Director and Co-Head of H.I.G. Bayside's U.S. Special Situations and Distressed Debt Strategy. With over 20 years of experience in private equity investing, Jackson shares his expertise on navigating distressed debt markets, building resilient portfolios, and uncovering hidden opportunities in complex financial situations. From sourcing distressed assets to managing risk, Jackson offers a masterclass on investing in challenging environments.
Highlights:
H.I.G. Capital’s Growth: How the firm expanded from a $75 million fund in 1993 to managing over $67 billion across multiple asset classes, including private equity, real estate, infrastructure, and credit.
Understanding Distressed Debt: The mechanics of distressed debt investing, including yield benchmarks and risk perceptions in distressed securities.
Risk Management in Distressed Investing: How H.I.G. constructs portfolios with a high hit rate and limited downside by focusing on first-lien debt.
Sourcing Distressed Opportunities: The unique ways distressed debt investors find deals—often without companies even being aware of the transactions.
Building Strategic Relationships: Why success in distressed debt relies on long-term relationships with restructuring attorneys, turnaround consultants, and industry insiders.
Portfolio Diversification Beyond Industries: The importance of avoiding over concentration in single risk factors, such as interest rates or energy prices, rather than just industry or geography.
The Role of Optimism in Distressed Investing: Why successful investors need to see beyond the immediate problems to uncover long-term value.
Lessons from 16 Years at H.I.G.: Jackson’s biggest takeaways, including why leadership stability is often a key indicator of a company’s strength.
H.I.G.'s Investment Philosophy: A deep dive into the firm’s focus on small and mid-cap, value-oriented, cash flow-centric investments and its commitment to seeking out complexity.
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Guest Bio:
Jackson Craig is the Managing Director and Co-Head of H.I.G. Bayside's U.S. Special Situations and Distressed Debt Strategy, overseeing investments in special situations, restructuring, and turnaround opportunities. With over 20 years of experience in private equity investing, Jackson has been instrumental in the firm’s growth and success in alternative investments. His expertise spans private equity, credit markets, and distressed investing, making him a leading voice in the industry.
Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
We’d like to thank @JuniperSquare and @ReedSmith for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Sponsor:
Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com.
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:
Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Jackson Craig: https://www.linkedin.com/in/jackson-craig-458b645b/
Links
H.I.G. Capital: www.higcapital.com
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(1:25) Understanding distressed debt investment
(4:53) Identifying and assessing distressed debt opportunities
(7:24) Investment process and due diligence
(9:02) Sponsor: Juniper Square
(9:36) Relationship management and distressed sales
(10:39) Tax considerations and investor base
(11:33) Investment discipline in distressed debt
(12:36) Success factors in distressed debt investing
(14:43) Portfolio diversification and risk management
(19:03) Sponsor: Reed Smith
(19:38) Evaluating business quality and management in distress
(21:02) Navigating the bankruptcy process
(22:02) Long-term strategy in distressed investing
(23:19) Overcoming sourcing challenges
(23:48) HIG's distinct investment approach and LP feedback
(25:21) Competitive advantage in distressed markets
(25:45) Closing remarks
...more
26min
February 14, 2025 E138: Do Relationships Drive Financial Returns? w/Jeremy Heer
In this episode of How I Invest, I speak with Jeremy Heer, Managing Director at the University of Illinois Foundation, about the art of networking, the power of super connectors, and the evolving landscape of institutional investing. Jeremy shares his insights on building relationships that drive investment success, the importance of strategic networking, and how attending conferences with intent can create game-changing opportunities. He also dives into the future of nuclear energy, the role of generalist investors in discovering new asset classes, and the long-term value of investment engagement.
Highlights:
The Role of a Super Connector: Jeremy explains what defines a “super connector” and why having them in your network is essential for success in investing.
Strategic Networking: How building and maintaining relationships across industries can unlock top-tier investment opportunities.
Conference Best Practices: Why proper preparation and a mix of structured and stochastic networking can maximize the value of attending events.
The Future of Nuclear Energy: Jeremy’s investment thesis on nuclear as a high-potential energy source and the challenges in capital deployment.
Generalist vs. Specialist Investing: How being a generalist can give investors a first-mover advantage in emerging asset classes.
Lessons from the University of Chicago: Jeremy shares insights from his time at one of the top endowments in the world.
The Long-Term Value of Relationship-Based Investing: Why some of the best investment opportunities emerge from patient, long-term engagement rather than immediate transactions.
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Guest Bio:
Jeremy Heer is the Managing Director of the University of Illinois Foundation, where he leads investment research and engagement. Before joining Illinois, he spent over a decade at the University of Chicago’s endowment, one of the top-performing institutional funds in the world. With deep expertise in building strategic relationships, Jeremy is a master of leveraging networks for investment success. He is passionate about connecting with top-tier investors, founders, and thought leaders to uncover unique opportunities in the market.
Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
We’d like to thank @JuniperSquare for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Sponsor:
Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com.
--
Stay Connected: X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Jeremy Heer: https://www.linkedin.com/in/jeremy-j-heer-cfa-caia/
Links:
University of Illinois Foundation: https://uif.uillinois.edu/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(3:56) Non-financial drives of super connectors
(4:11) Sponsor: Juniper Square
(5:55) How to be memorable & Networking at conferences
(12:33) The investment potential of nuclear energy & University experiences
(17:00) The unique role at University of Illinois Foundation & Generalist investors in VC
(19:03) Closing remarks
...more
21min
February 11, 2025 E137: Lessons from Managing $300 Billion Dollars w/ John Skjervem (CIO of URS)
In this episode of How I Invest, I dive deep into a discussion with John Skjervem, Chief Investment Officer at Utah Retirement Systems (URS), to uncover the unique governance and investment strategies behind one of the most innovative public pension funds in the United States. John shares his insights on governance structures, private equity allocations, the benefits of a "fishbowl-free" decision-making process, and his approach to alternative energy investments. Whether you're curious about pension fund management or the future of disruptive energy investments like nuclear fusion, this episode is a masterclass in strategic thinking and long-term investing.
Highlights:
Governance Matters: Why URS’s closed-door investment meetings create better outcomes compared to traditional public pension governance.
Transparency vs. Returns: How excessive transparency can lead to political grandstanding and ultimately harm long-term investment performance.
Asset Allocation Strategy: A deep dive into URS’s allocation, including a 14% allocation to private equity with significant exposure to venture capital.
Direct Real Estate Investments: How URS has built a successful real estate portfolio, reducing fees and maintaining long-term control over assets.
Energy and Infrastructure Investments: The role of direct investments in oil, gas, and alternative energy as an inflation hedge.
The Case for Venture Capital: Why URS prioritizes venture capital investments over private credit to maximize returns.
Betting on Nuclear Fusion: The potential for a 100x return on URS’s investments in fusion energy and the long-term implications for the energy sector.
Size vs. Agility: Why smaller funds like URS have an advantage in private markets despite their scale limitations.
Lessons from the Global Financial Crisis: How John’s approach to risk management and asset allocation was shaped by 2008.
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Guest Bio:
John Skjervem serves as the Chief Investment Officer at Utah Retirement Systems, where he oversees over $50 billion in assets. With prior experience managing larger funds like the Oregon Public Employees Retirement Fund and Northern Trust's wealth business, John brings a wealth of expertise to his current role. Known for his innovative governance approach and deep knowledge of alternative investments, John is passionate about achieving long-term success for URS beneficiaries.
Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
We’d like to thank @JuniperSquare @ReedSmith for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
SPONSOR:
Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com.
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:
Twitter:
David Weisburd: https://x.com/DWeisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
John Skjervem: https://www.linkedin.com/in/john-d-skjervem-cfa-4698794/
Links
Utah Retirement Systems: https://www.urs.org/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(1:00) Asset allocation and governance at Utah Retirement Systems
(4:07) Governance structure at Utah Retirement Systems
(9:25) Long-term investment challenges
(10:57) Sponsor: Juniper Square
(11:30) Private equity and real estate in asset allocation
(15:44) Managing a $50 billion fund
(16:25) Sponsor: Reed Smith
(17:30) Investment check sizes and advisory roles
(20:31) Comparing Utah Retirement Systems with Alaska Permanent Fund
(22:11) Lessons from the 2008 financial crisis
(23:57) Exploring high-risk investments: Fusion portfolio
(26:10) Closing remarks
...more
27min
February 07, 2025 E136: Navigating Startup and Venture Capital Legal Risks w/Constantine Karides
In this episode of How I Invest, I interview Constantine Karides, a Lead Partner at Reed Smith, to discuss the critical role lawyers play in the startup and venture capital ecosystem. Constantine shares insights on what founders and investors should look for in legal counsel, the leverage model law firms use, and how AI is reshaping the legal landscape. From the importance of choosing the right law firm to navigating legal costs effectively, this episode is packed with actionable advice for entrepreneurs, venture capitalists, and investors.
Highlights:
Choosing a Lawyer as a Strategic Partner: Beyond paperwork, founders should seek legal advisors who bring investor connections, industry expertise, and pricing flexibility.
The Importance of Internal Influence: How a lawyer’s standing within a firm impacts their ability to secure favorable terms and resources for clients.
VCs & Legal Counsel: What venture capital funds should prioritize when selecting legal partners and how these relationships can create long-term value.
Law Firm Profit Models: Understanding the leverage model law firms use to maximize profits and how clients can navigate these dynamics.
AI & The Future of Law: How artificial intelligence is transforming the legal industry, from document review to litigation strategy.
Building Long-Term Client Relationships: Constantine’s philosophy on blending business with personal relationships to drive success.
Lessons from Experience: Mistakes Constantine made early in his career and how they shaped his approach to law and business.
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Guest Bio:
Constantine Karides is a Lead Partner at Reed Smith, a global law firm known for its expertise in venture capital, private equity, and corporate transactions. With over 30 years of experience, Constantine has built a reputation as a trusted advisor to startups, funds, and investors, offering not just legal counsel but also strategic business insights. Recognized as a "rainmaker" at Reed Smith, he emphasizes client relationships, networking, and long-term value creation.
Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
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:
Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Constantine Karides: https://www.linkedin.com/in/constantine-karides/
Links
Reed Smith: www.reedsmith.com
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(2:08) Law firms' internal credibility and Venture Capital specific needs
(5:29) Evaluating Startups and the leverage model in law firms
(9:57) Trust-building and client relationship philosophy
(14:41) Early career lessons and the impact of AI on the legal field
(19:00) Client views on AI adoption in law firms
(21:03) Closing remarks
...more
23min
February 04, 2025 EP135: How to Access Top Quartile Venture Capital Funds w/Mel Williams
In this episode of How I Invest, I have a conversation with Mel Williams, Co-Founder and General Partner at TrueBridge Capital Partners. We dive into TrueBridge’s pivotal role as Forbes' data partner for the prestigious Midas List, its strategic approach to venture capital fund-of-funds investing, and how the firm consistently identifies and backs the top-performing fund managers. Mel provides a masterclass on portfolio construction, risk management, and scaling a successful venture investment platform. Whether you’re an institutional investor, a fund manager, or simply intrigued by the inner workings of venture capital, this episode is packed with essential takeaways.
Highlights:
The Midas List Partnership: How TrueBridge collaborates with Forbes to curate the definitive VC ranking and what it means for the industry.
Fund of Funds Strategy: The five key investment strategies that shape TrueBridge’s unique venture approach—core venture, seed, direct, secondary, and blockchain investments.
The Power of Forced Ranking: A disciplined framework for ranking fund managers and how it enhances returns.
Gaining a Competitive Edge: How TrueBridge’s relationships with elite GPs provide them unparalleled access and insight.
Navigating Blockchain Volatility: TrueBridge’s philosophy on investing in blockchain and adjusting for its extreme market cycles.
Scaling Venture Funds Effectively: Best practices for fund managers to grow while maintaining their competitive advantage.
International vs. Domestic Venture Investing: How TrueBridge evaluates and ranks global venture funds against U.S.-based managers.
Lessons from Building TrueBridge: The realities of raising early funds and scaling a top-tier fund-of-funds platform.
Debunking the Fund-of-Funds Fee Myth: How TrueBridge offsets the double-fee structure through strategic overcommitment and capital recycling.
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Guest Bio:
Mel Williams is the Co-Founder and General Partner at TrueBridge Capital Partners, a premier venture capital fund-of-funds specializing in backing top-tier venture firms and startups. With a background in institutional investing at the University of North Carolina Endowment and the Rockefeller Foundation, Mel brings unparalleled expertise in fund selection, portfolio construction, and venture capital strategy. Under his leadership, TrueBridge has cultivated one of the most coveted LP portfolios in the industry, leveraging deep networks and a research-driven investment approach.
Our Podcast now receives more than 200,000 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/
Mel Williams: https://www.linkedin.com/in/mel-williams-00584a5/
Links
TrueBridge Capital Partners: https://www.truebridgecapital.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(4:38) Investing in blockchain and managing volatility in venture funds
(5:51) Building relationships and the forced ranking system in portfolio management
(10:21) Criteria for adding or removing venture fund managers
(14:43) Best practices for scaling and international venture investments
(20:23) Challenges in raising funds and the venture industry evolution (2012-2021)
(24:17) Comparing fund of funds to direct venture capital investments
(26:51) Efficiency and key aspects of TruBridge's fund of funds model
(29:05) Closing remarks
...more
30min
January 31, 2025 E134: How I Accidentally Started a Billion Dollar Tech Company w/Carta CEO Henry Ward
In this episode of How I Invest, I dive deep into a conversation with Henry Ward, CEO of Carta, to discuss his journey building one of the most transformative companies in private market infrastructure. From cap table management to fund administration and beyond, Henry shares his insights on entrepreneurship, innovation, and the future of private equity. We delve into Carta's strategic pivots, its playbook for turning services into scalable software, and Henry's contrarian views on AI and leadership. This episode is packed with lessons for founders, investors, and operators navigating the evolving landscape of private capital.
Highlights:
The Carta Journey: How Carta evolved from solving cap table management to building software for fund CFOs.
Scaling Through Innovation: The importance of constantly iterating and innovating in markets with limited growth potential.
AI in Private Markets: Why Henry is focused on using AI to enhance customer experiences instead of reducing headcount.
Building the Carta Cartel: How former Carta employees are founding companies with Henry's support—and reshaping angel investing.
Services to Software: Carta's unique playbook for acquiring service businesses and turning them into software-driven solutions.
Future of Fund Admin: The roadmap for automating fund administration and achieving “one-click” reporting by 2030.
Private Equity Expansion: Carta’s strategy for becoming the operating system for private capital beyond venture.
Leadership Insights: Henry’s take on founder mode, micromanagement, and why caring deeply is essential to great leadership.
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Guest Bio:
Henry Ward is the CEO of Carta, a company revolutionizing private market infrastructure through software. Since its founding in 2012, Carta has grown into the industry standard for cap table management, fund administration, and private market data. Henry is also an active angel investor, backing numerous startups founded by former Carta employees. Known for his visionary thinking and contrarian ideas, Henry is committed to reshaping how private capital markets operate.
Our Podcast now receives more than 200,000 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
Henry Ward: @henrysward
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Henry Ward: https://www.linkedin.com/in/heward/
Links:
Carta: https://www.carta.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(2:31) Building Carta: Innovation and Execution
(5:03) AI's Role and Impact at Carta
(9:21) Fund Administration Challenges and Solutions
(12:33) Investing in Carta's Team and Culture
(14:51) Angel Investing and CEO Controversies
(17:48) Balancing Founder and Investor Roles
(22:03) Carta's Acquisition Strategy and Automation Goals
(25:10) Carta's Role for CFOs in Private Equity and VC
(27:32) Carta's Strategic Pivot and Growth Plans
(30:39) Brand Transition: Venture to Private Equity
(34:35) Closing remarks
...more
35min
January 28, 2025 E133: Lessons from Investing in 2200 Startups (in 23 Minutes)
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.
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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 [email protected].
#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 [email protected].

(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
...more
24min
January 24, 2025 E132: How Nichole Wischoff Raised a $50M Fund in 5 Months
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 [email protected].
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 [email protected].
(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
...more
30min
January 21, 2025 E131: Can VCs Make Money in Deep Tech? w/Nick Shekerdemian
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 [email protected].
#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 [email protected].
(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
...more
29min

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The podcast currently has 143 episodes available.

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