How I Invest with David Weisburd

By David WeisburdBusiness Investing

How I Invest with David Weisburd episodes

November 04E451: Peter Thiel's 27-Year Partner on the AI Bubble, the Venture Capital Crisis, and the PayPal Mafia
What if the best venture capital opportunities are hiding in the 47 states Silicon Valley largely ignores?
In this episode, I sit down with Jack Selby, Managing Director at Thiel Capital and an early member of the PayPal Mafia, to explore why he believes venture capital has become dangerously concentrated in Silicon Valley and overpriced AI startups. After working alongside Peter Thiel for 27 years, Jack is pursuing a contrarian strategy through Copper Sky, investing in promising technology companies outside California, New York, and Massachusetts. Jack explains why he can invest at roughly one-tenth of Silicon Valley valuations, how the next Carvana could emerge from cities like Phoenix or Milwaukee, and why venture capital's obsession with trillion-dollar outcomes may be hurting LP returns. We also discuss the hiring culture behind PayPal's extraordinary alumni network, why struggling venture firms have become zombies, and Jack's conviction that today's AI investment boom is a bubble.
Highlights:
How PayPal assembled a team that went on to build some of Silicon Valley's most influential companies
What Jack learned from working alongside Peter Thiel for 27 years
Why nearly 90% of venture capital flows to just three states
How Copper Sky invests at roughly one-tenth of Silicon Valley valuations
Why Silicon Valley's greatest advantage may be access to capital rather than talent
How Jack uses his network to connect non-coastal founders with Silicon Valley investors
Why entry price matters more than finding the next trillion-dollar company
How venture capital's liquidity crisis created a generation of zombie funds
Why AI is allowing smaller teams to build valuable companies outside traditional technology hubs
Why Jack believes today's AI investment boom is a bubble
Guest Bio:
Jack Selby is Managing Director at Thiel Capital and an early member of the PayPal founding team, where he led international operations before the company's acquisition by eBay. He has worked alongside Peter Thiel for 27 years and co-founded Clarium Capital, a global macro hedge fund. Jack is also an investor at Copper Sky, a venture capital firm focused on identifying promising technology companies outside traditional coastal venture markets. His investment experience spans technology, finance, venture capital, film, and nonprofit initiatives.
Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
**Stay Connected with David Weisburd: **
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdcapital.com/
**Stay Connected with Jack Selby: **
LinkedIn:https://www.linkedin.com/in/jackselby/?skipRedirect=true
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) How PayPal Built the Most Successful Network in Silicon Valley
(4:42) What Jack Learned From Working With Peter Thiel for 27 Years
(5:30) Why 90% of Venture Capital Goes to Just Three States
(8:43) Silicon Valley's Biggest Advantage Isn't Talent
(11:42) How to Find the Next Carvana Outside Silicon Valley
(17:23) Why Jack Invests at One-Tenth of Silicon Valley Valuations
(23:05) How AI Could Transform Startup Economics
(26:19) The Work Ethic and Hiring Lessons Behind the PayPal Mafia
(30:09) Why Venture Capital Is Filled With Zombie Funds
(40:05) Why Jack Believes the AI Investment Boom Is a Bubble
57 min
November 02E450: Brijesh Jeevarathnam on Why Venture Is Eating Public Markets, Picking Great VCs, and the AI Boom
What if just 7% of venture-backed companies generate all the gains, and the real skill is identifying the managers who can find them first?
In this episode, I sit down with Brijesh Jeevarathnam, Partner and Global Head of Fund Investments at Adams Street Partners, to explore how institutional investors identify exceptional venture capital managers in an increasingly crowded market. Drawing on more than 20 years of experience evaluating venture and private equity funds, Brijesh explains why the best VCs think independently, how they earn access to extraordinary founders, and why past performance is often the least predictive part of manager selection. We discuss how Adams Street evaluates emerging managers, the role of information asymmetry in fund investing, and why venture capital is increasingly capturing value creation once available to public market investors. Brijesh also shares how AI is changing institutional due diligence and why the next generation of transformative AI companies may still be ahead of us.
Highlights:
Why the best venture capitalists see opportunities before they become consensus
How the number of venture firms expanded from roughly 500 to 4,000
The three characteristics Adams Street looks for when selecting venture managers
Why having a chip on your shoulder can be an advantage in venture capital
How early LP commitments create lasting relationships with emerging managers
Why information asymmetry remains a competitive advantage in fund investing
How to identify exceptional managers before their investment returns materialize
What separates founder whisperers from venture capitalists who simply provide capital
Why venture capital is increasingly capturing value creation from public markets
How Adams Street studies missed investments through its anti-portfolio
Why just 7% of venture-backed companies generate all the gains
How AI is transforming due diligence without replacing human judgment
Why power-law returns may still exist in late-stage venture investing
Why the AI investment cycle could still be in its earliest innings
Guest Bio:
Brijesh Jeevarathnam is a Partner and Global Head of Fund Investments at Adams Street Partners, a global private markets investment firm. He has more than two decades of experience evaluating venture capital and private equity managers, with a focus on identifying exceptional investment teams and building long-term institutional partnerships.
Sponsor:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit junipersquare.com/howiinvest.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
**Stay Connected with David Weisburd: **
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Brijesh Jeevarathnam:
LinkedIn:https://www.linkedin.com/in/brijesh2075/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) What Separates the World's Best Venture Capitalists?
(4:28) Why Venture Capital Has Changed Dramatically in 20 Years
(7:22) The Three Things Adams Street Looks for in VC Managers
(12:45) How LP Relationships Create an Information Advantage
(14:39) How Long Does It Take to Know if a VC Manager Is Good?
(19:06) How to Identify a VC Who Can Win Over the Best Founders
(27:43) Why Venture Capital Is Eating the Public Markets
(38:03) How Adams Street Learns From Its Biggest Investment Mistakes
(41:23) Why Just 7% of Startups Generate All the Gains
(56:34) What Inning of the AI Boom Are We Really In?
1 hr 6 min
October 30E449: Federated Hermes CEO on $400 Billion in Cash, the Private Markets Boom, and AI
What if the most overlooked asset in your portfolio is the one that gives you the freedom to invest in everything else?
In this episode, I sit down with Christopher Donahue, President, Chair and CEO of Federated Hermes, to explore how the firm manages approximately $700 billion in money market assets and why cash is far more than an idle allocation. Chris explains how liquidity creates financial flexibility, why trust and scale have concentrated the money market industry among a handful of firms, and what stablecoins can learn from decades of cash management. We also discuss how corporations manage their cash reserves, why AI could improve investment management without replacing employees, and how Federated Hermes plans to expand its private markets business. After more than 50 years at the firm, Chris shares the principles behind its longevity and why culture, trust, and disciplined risk-taking remain essential to building an enduring financial institution.
Highlights:
Why cash is one of the most misunderstood assets in an investment portfolio
How Federated Hermes built a money market business managing approximately $700 billion
Why liquidity, trust, and operational reliability matter more than chasing yield
How regulation and size created an oligopoly in money market funds
What stablecoin companies can learn from the money market industry
Why Federated Hermes chose not to compete directly with its distribution partners
How corporations, pension funds, and individuals should think differently about cash reserves
The differences between Treasury, government, and prime money market funds
Why Chris sees AI as an opportunity to improve quality rather than eliminate jobs
How Federated Hermes built a culture that has endured for more than five decades
Why the firm's private markets business could eventually become larger than its existing operations
The importance of disciplined risk-taking and entrepreneurial confidence
Guest Bio:
Christopher Donahue is Chairman, President, Chair and CEO of Federated Hermes, a global investment management firm headquartered in Pittsburgh. He joined the company in 1972 and served as President and Chief Operating Officer from 1993 to 1998 before becoming CEO in April 1998.Under his leadership, Federated Hermes has expanded its investment management capabilities across money markets, equities, fixed income, and private markets while maintaining a focus on liquidity, client service, and long-term relationships.
Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
**Stay Connected with David Weisburd: **
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdpierce.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why Cash Is the Most Misunderstood Asset
(2:02) How Federated Hermes Built a $700 Billion Money Market Business
(3:45) Why Only a Handful of Firms Dominate Cash Management
(5:39) What Stablecoins Can Learn From Money Market Funds
(7:02) Why Federated Hermes Refuses to Compete With Its Customers
(11:14) How Corporations Should Think About Cash Reserves
(16:21) Treasury vs. Government vs. Prime Money Market Funds
(20:34) How AI Is Changing the Future of Asset Management
(24:38) The Secret Behind 50 Years of Leadership at Federated Hermes
(37:06) Why Private Markets Could Become Federated Hermes' Biggest Business
49 min
October 28 E448: Gavin Ezekowitz on AI Valuations, Asymmetric Returns, and Why Great Investors Fail
How do you invest in generational companies like Anthropic, OpenAI, and SpaceX before everyone recognizes their potential?
Gavin Ezekowitz is the Co-Founder and Chief Investment Officer of BFA Global Investors, an alternative investment firm providing access to private market opportunities. In this episode, Gavin explains how BFA gained exposure to Anthropic, OpenAI, and SpaceX through GP relationships, including its early Anthropic investment at a $17 billion valuation.
Highlights:
- How BFA gained exposure to Anthropic, OpenAI, and SpaceX
- Why Gavin invested in Anthropic at a $17 billion valuation
- The investment lesson Gavin learned from missing Cursor
- Why great founders can disrupt their own businesses
- How to underwrite companies when future markets are impossible to predict
- Why fundraising ability alone does not make a great founder
- What SpaceX reveals about mission-driven leadership and exceptional talent
- Why venture capital should be viewed as a 20-year asset class
- How portfolio construction preserves exposure to power-law outcomes
- Why pacing and position sizing matter more than predicting market cycles
- How smaller venture funds can outperform larger, established firms

Guest Bio:
Gavin Ezekowitz is the Co-Founder and Chief Investment Officer of BFA Global Investors, an alternative investment firm focused on delivering outstanding returns through disciplined processes and trusted relationships.

Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.

AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.

AlphaSummit Discount Code: AS26HII50

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].

Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with Gavin Ezekowitz:
LinkedIn:https://www.linkedin.com/in/gavin-ezekowitz-966a29a/

Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) How Gavin Invested in Anthropic, OpenAI, and SpaceX
(1:08) Why Gavin Invested in Anthropic at a $17 Billion Valuation
(3:52) The Investing Lesson Gavin Learned From Missing Cursor
(10:42) How Do You Value a Generational AI Company?
(14:08) Are the Best Founders Capital Magnets?
(23:54) What SpaceX Reveals About Great Technology Entrepreneurs
(28:39) Why Portfolio Construction Matters More Than Market Timing
(34:20) Can Small Venture Funds Outperform the Biggest Firms?
(41:54) Why the Best Investors Make Concentrated Bets
(53:14) What Separates Exceptional Venture Capital Managers?
1 hr 14 min
October 26 E447: Anthropic at $2 Trillion? The AI Bubble, and Why the Best Startups Always Look Overvalued
Are venture capitalists overpaying for the next generation of AI winners?
Matthew Harris is a Partner at Bain Capital Ventures, where he invests in financial services and technology companies. In this episode, Matthew explains why the best venture investments often look overpriced, how valuation discipline can cause firms to miss power-law winners, and why today's AI market is increasingly driven by consensus.
Highlights:
- Why Bain Capital Ventures historically struggled to capture some power-law outcomes
- How valuation discipline can cause investors to miss exceptional companies
- Why the best startups often appear overpriced at every funding round
- How consensus investing is changing venture capital
- Why Matthew believes there are still undiscovered AI winners
- The two investment themes driving Bain Capital Ventures' recent strategy
- How AI-native services companies could disrupt insurance, law, and other industries
- Why OpenAI and Anthropic may avoid competing directly with their largest customers
- How access to compute could determine the next AI leader
- Whether Anthropic could justify a $2 trillion valuation
- Why AI agents could expand the market beyond eight billion human users
- How consistent investment pacing protects against venture market cycles
- Why personal agency matters more as AI makes knowledge and tools widely accessible

Guest Bio:
Matthew Harris is a Partner at Bain Capital Ventures, where he focuses on investments in financial services and technology. His investment interests include payments, specialty lending, fintech, asset management, trading systems, and insurance.

Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.

AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.

AlphaSummit Discount Code: AS26HII50

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].

Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with Matthew Harris:
LinkedIn:https://www.linkedin.com/in/mattcharris/?isSelfProfile=false

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why Bain Capital Ventures Missed Some Power-Law Winners
(3:13) Why the Best Startups Always Look Overvalued
(6:51) Are There Still Diamonds in the Rough?
(10:14) How AI Is Changing Bain Capital Ventures' Investment Strategy
(16:10) Why AI-Native Services Could Beat Traditional Software
(22:19) Will Compute Determine Who Wins the AI Race?
(29:03) Is Anthropic Worth $2 Trillion?
(36:12) Why AI Agents Could Expand the Market Beyond Eight Billion People
(49:02) Are We in an AI Investment Bubble?
(53:48) The Most Important Skill for Surviving the AI Era
1 hr 3 min
October 23 E446: Vista Equity President: The Death of SaaS? AI Agents and the $3 Trillion Opportunity
Is AI destroying the software industry, or creating its biggest investment opportunity yet?
David Breach is President of Vista Equity Partners, a firm managing approximately $100 billion in assets. In this episode, David explains why the recent selloff in software stocks may be missing a much larger opportunity: AI-powered digital workers. We explore Vista's repeatable playbook for creating value in enterprise software, why mission-critical products and proprietary data remain competitive advantages, and how AI could expand software's addressable market into trillions of dollars in services. David also shares how Vista evaluates software companies amid AI disruption, why incumbents may be better positioned than startups to deploy AI agents, and the career lessons that took him from selling juice to leading one of the world's largest software-focused private equity firms.
Highlights:
- Why David left Kirkland & Ellis to help build Vista Equity Partners
- How Vista grew from $13 billion to approximately $100 billion in AUM
- The four pillars of Vista's repeatable software value creation playbook
- Why David believes the SaaS selloff doesn't reflect software's long-term opportunity
- How AI agents could unlock a $3 trillion services market
- Why existing software companies may have an advantage over AI-native startups
- The three characteristics Vista looks for in mission-critical software
- Why recent customer retention data matters more than historical performance
- How proprietary data and industry expertise create defensible competitive advantages
- Why cybersecurity and data protection are central to enterprise AI adoption
- How Vista approaches diversification and portfolio construction
- The career lesson David believes matters more than intelligence or talent

Guest Bio:
David A. Breach is President of Vista Equity Partners. He serves on the investment committees for Vista's Flagship, Foundation, Endeavor and Perennial Funds and is Co-CEO of VistaOne, the firm's evergreen private equity vehicle.

Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.

AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.

AlphaSummit Discount Code: AS26HII50

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].

Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with David Breach:
LinkedIn:https://www.linkedin.com/in/david-breach/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why David Left Kirkland & Ellis to Join Vista Equity Partners
(3:41) The Vista Playbook for Creating Value in Software Companies
(7:12) Is AI Making Software Uninvestable?
(11:08) Why AI Could Trigger a Major Revaluation of SaaS Companies
(14:00) Will OpenAI and Anthropic Replace Enterprise Software?
(20:03) The Three Things Vista Looks for in Software Investments
(26:23) How AI Is Changing Software Investment Due Diligence
(35:20) Why Data Security Could Determine the Winners in AI
(41:13) How Vista Constructs Its Private Equity Portfolios
(49:34) From Selling Juice to Leading Vista Equity Partners
59 min
October 21 E445: AngelList: Why Picking Winners Is the Wrong Way to Invest in Startups
What if the biggest advantage in venture capital isn't picking winners, but getting access to them?
Erik Syvertsen is GM of Asset Management and Chief Legal Officer at AngelList and Chairman of USVC. Drawing on AngelList's extensive venture investment data, Erik explains why seed and growth investing operate like two different asset classes, why the best startups often command higher valuations from the beginning, and how access drives venture returns. We explore the power law, why doubling down on winners matters, the two strategies for building successful venture portfolios, and the challenges of selling investments in breakout companies. Erik also discusses how USVC aims to expand access to private markets as companies like OpenAI, Anthropic, and SpaceX create enormous value before going public.
Highlights:
- Why Erik believes venture capital is actually two different asset classes
- Why access may matter more than picking winners at the seed stage
- What AngelList's data reveals about startup valuations and future returns
- Why venture's power law makes portfolio concentration so important
- How the "Cathedral and Bazaar" framework explains winning VC -strategies
- Why the middle market of venture capital may face structural challenges
- How LPs can identify emerging managers with a genuine access advantage
- Why investing across vintages matters more than timing the market
- What Erik learned from an investment in Anthropic that was sold too early
- Why selling shares can damage a VC's relationship with founders
- Why individual investors struggle to access private-market value creation

Guest Bio:
Erik Syvertsen is GM of Asset Management and Chief Legal Officer at AngelList and Chairman of USVC. With more than eight years at AngelList, Erik works at the intersection of venture capital, investment management, and private-market access.

Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.

AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.

AlphaSummit Discount Code: AS26HII50

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].

Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Erik Syvertsen:
LinkedIn:https://www.linkedin.com/in/erik-syvertsen-334b1138/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why Venture Capital Is Actually Two Different Asset Classes
(2:32) What AngelList's Data Reveals About Startup Valuations
(5:21) Why Access Matters More Than Picking Winners
(12:50) The Power Law Behind Venture Capital Returns
(17:33) The Cathedral and Bazaar Model of Venture Investing
(24:59) How to Find Emerging Managers With an Access Advantage
(28:08) How Many Startup Investments Does It Take to Find a Winner?
(32:15) The Anthropic Investment Erik Wishes He Had Held
(38:08) Why Retail Investors Are Missing Private-Market Wealth Creation
(52:54) How USVC Plans to Expand Access to Venture Capital
1 hr 2 min
October 19 E444: NEPC President on AI Portfolio Risk, Finding Top Funds, and Preparing for a Downturn
What if the biggest advantage in institutional investing isn’t finding better managers, but building an organization that can make better decisions over decades?
In this episode, I sit down with Tim McCusker, President of NEPC, which advises on approximately $2 trillion in assets, to discuss what separates the best institutional investors from everyone else. Tim explains why even sophisticated endowments and pension funds fall into peer-driven investing, how governance and incentives shape long-term returns, and why the strongest allocators are willing to invest when others are retreating.
Highlights:
- What advising on nearly $2 trillion reveals about institutional investing
- Why sophisticated investors still fall into herd behavior
- How governance and investment committee support can determine long-term returns
- Why the best LPs stay committed to managers during market downturns
- How endowments and pension funds construct portfolios differently
- Why the best co-investment programs focus on manager selection rather than re-underwriting every deal
- Why venture capital deserves a place in portfolios beyond its return potential
- How AI concentration, changing correlations, and portable alpha are reshaping portfolio risk

Guest Bio:
Tim McCusker is President of NEPC, an institutional investment consulting firm advising on approximately $2 trillion in assets across more than 400 clients, including pension funds, endowments, foundations, and healthcare organizations.

Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.

AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.

AlphaSummit Discount Code: AS26HII50

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].

Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with Tim McCusker:
LinkedIn:https://www.linkedin.com/in/tim-mccusker-76174278/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) What Advising on $2 Trillion Reveals About Investing
(3:07) The Biggest Mistake Sophisticated Institutional Investors Make
(7:15) Why the Best CIOs Stay in Their Seats for Decades
(10:10) What Separates the Top Institutional Investors?
(16:00) How the Best Endowments Construct Their Portfolios
(20:14) The Biggest Mistake LPs Make in Co-Investments
(25:48) How NEPC Finds the Next Generation of Venture Managers
(31:22) Why Venture Capital Belongs in Institutional Portfolios
(36:33) Is Portable Alpha Worth the Risk?
(43:34) Why AI Concentration Keeps Tim Up at Night
54 min
October 16 E443: Why the Next Trillion-Dollar Startup Won’t Be a Software Company
What if AI makes software abundant and shifts venture capital’s biggest opportunities into the physical world?
Leo Polovets is a General Partner at Humba Ventures, an early-stage deep tech fund investing across robotics, defense, energy, manufacturing, and other physical industries. Leo explains why AI is commoditizing software, why hardware may capture more value as a result, and why some of the best opportunities are hiding in industries with almost no startup competition. We also discuss how to underwrite deep tech before revenue, what separates exceptional founders, the infrastructure bottlenecks created by AI, and why the biggest risk to deep tech may be its dependence on continued funding.
Highlights:
- Why the best companies and investors need a lane uniquely their own
- Why quantity of meetings can improve venture investment quality
- How AI growth is changing the definition of exceptional traction
- Why deep tech companies have a completely different revenue curve
- What separates the best venture capitalists from average investors
- Why Leo believes hardware investing is becoming more attractive
- How to evaluate deep tech companies years before meaningful revenue
- Why hardware may not be as capital intensive as investors assume
- The founder traits that matter most when building physical products
- Why Leo is cautious on investing directly in humanoid robotics

Guest Bio:
Leo Polovets is a General Partner at Humba Ventures, an early-stage deep tech fund investing 500K–1M in companies across robotics, bio, defense, energy, manufacturing, and other physical industries. He previously co-founded Susa Ventures, an early investor in companies including Robinhood, Flexport, and Stord.

Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit junipersquare.com/howiinvest.

AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit alpha-sense.com/howiinvest to learn more.

AlphaSummit Discount Code: AS26HII50

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].

Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Leo Polovets:
LinkedIn:https://www.linkedin.com/in/lpolovets

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why the Best Investors Need Their Own Lane
(2:05) Why More Meetings Can Make You a Better Investor
(6:14) What Separates the Best Venture Capitalists?
(10:03) Why Leo Is So Bullish on Hardware
(12:31) How Do You Underwrite a Deep Tech Startup?
(16:08) Is Hardware Really More Capital Intensive?
(22:38) Where Are Deep Tech’s Most Underrated Opportunities?
(33:28) What Separates the Top 0.1% of Founders?
(41:28) Why Leo Is Cautious on Humanoid Robotics
(56:26) The Investing Lesson Leo Learned the Hard Way
1 hr 3 min
October 14E442: Nelson Mills on Building a $100 Billion Company, the China Threat, and the Future of War
What happens when autonomous underwater vehicles become cheap enough to manufacture at scale?
Nelson Mills is the Founder of Vatn Systems, a defense technology company building autonomous underwater vehicles. Nelson explains why undersea autonomy has lagged aerial drones, how advances in AI, navigation, manufacturing, and autonomy are changing the economics, and why Vatn is building lower-cost systems designed to operate at scale. We also discuss raising $85 million for a hardware startup, the rise of asymmetric warfare, lessons from Anduril, and what it takes to build a new defense prime.
Highlights:
Why Nelson left venture capital to become a founder
Why undersea autonomy is finally reaching an inflection point
The navigation and communications problems that make underwater technology so difficult
How Vatn raised its first $2 million pre-seed round in just 30 days
Why hardware founders should start with the smallest viable version of their product
Vatn’s plan to become a focused defense prime for the undersea market
What Anduril proved about building defense technology differently
How lower-cost underwater vehicles could change deterrence for smaller countries
The biggest hiring lesson Nelson learned as a founder
Why founders should always be building relationships for their next round
Guest Bio:
Nelson Mills is the Founder of Vatn Systems, a defense technology company building autonomous underwater vehicles. After growing up on the water and spending roughly nine years operating at startups, Nelson moved into venture capital before leaving to build Vatn.
Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
**Stay Connected with David Weisburd: **
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Nelson Mills:
LinkedIn:https://www.linkedin.com/in/millsn/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) How Growing Up on a Sailboat Led to Vatn Systems
(1:18) Why Nelson Left Venture Capital to Become a Founder
(6:08) Why Undersea Autonomy Is Finally Having Its Moment
(8:20) What Needs to Happen for Underwater Drones to Scale?
(11:13) How Do You Build a Company Everyone Says Is Impossible?
(12:41) How Vatn Raised $2 Million on a Dream
(20:53) How Vatn Went From Pre-Seed to $85 Million Raised
(21:48) Can Vatn Become the Next Defense Prime?
(27:42) How Defense Technology Could Change Global Deterrence
(45:21) The Advice Nelson Would Give Himself as a First-Time Founder
54 min

About How I Invest with David Weisburd

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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,…