What if the biggest AI investment opportunity isn’t AI companies, but the infrastructure required to make AI possible? David sits down with Stuart Waugh, Managing Partner of Northleaf Capital Partners, to explore why the AI boom is creating massive demand for power, data centers, communications networks, and other essential infrastructure. Stuart explains why Northleaf estimates roughly $40 trillion of infrastructure investment will be needed across its addressable markets over the next decade, and why governments increasingly need private capital to help fund it.

Highlights:

• Why AI’s biggest bottleneck may be infrastructure, not computing.
• The investment opportunity behind AI’s enormous demand for power.
• Why Northleaf sees roughly $40 trillion of addressable infrastructure investment.
• How infrastructure can provide long-term cash flows, inflation protection, and lower correlation.
• Why the middle market becomes more attractive as mega-funds get bigger.
• How secondaries became a mainstream portfolio management tool.
• Why relationships and proprietary information still create an edge in secondaries.
• How institutional investors are approaching today’s private credit uncertainty.
• Why Stuart believes “boring” can be an investing advantage.
• The lessons behind scaling Northleaf from five people to more than 300.

Guest Bio:

Stuart Waugh is the Managing Partner of Northleaf Capital Partners and a member of the firm’s Executive Committee. He oversees the direction and development of Northleaf’s private markets investment strategies and fund management capabilities and chairs its Investment Committees. Stuart joined Northleaf’s predecessor, TD Capital, in 2002. Earlier in his career, he worked at McKinsey & Company, BPI Financial Corporation, and McCarthy Tétrault. He holds a B.A. from Trinity College at the University of Toronto and an LL.B. from the University of Toronto Faculty of Law.

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

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Stuart Waugh:

Website:https://www.northleafcapital.com/person/stuart-waugh

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 AI’s Biggest Opportunity Isn’t AI (8:56) The $40 Trillion Infrastructure Opportunity (15:36) Why Deglobalization Could Make Infrastructure More Valuable (23:18) Why the Traditional 60/40 Portfolio Is Disappearing (27:54) The Private Markets Liquidity Engine Most Investors Miss (33:14) The Hidden Advantage in Buying Secondaries (42:47) Is the Private Credit Fear Creating a Buying Opportunity? (50:08) What Most GPs Get Wrong About Their LPs (56:14) Why “Boring” May Be the Best Investment Strategy

Venture capital was designed around a relatively simple model: invest in a startup, help it grow, and eventually exit through an acquisition or IPO. David sits down with Benjamin Black Powerlaw Corp. (Nasdaq: PWRL), Akkadian Ventures, Ben invests in growth-stage technology companies while providing alternative liquidity to founders, employees, angel investors, and venture funds. In this episode, Ben and David unpack the evolution of the venture secondary market, why great companies staying private longer creates an entirely different opportunity set, how sophisticated investors price illiquid private-company shares, and why liquidity itself is becoming a critical piece of venture capital infrastructure. The result is a different way to think about private markets: the investment opportunity doesn't end after the primary financing round.

Highlights:

• Why venture secondaries have become a major private-market opportunity
• What happens when great companies stay private for much longer
• How Akkadian approaches growth-stage technology investing
• Why founders and employees increasingly need pre-IPO liquidity
• How investors price private-company secondary transactions
• The difference between primary and secondary venture investing
• Why venture funds themselves can become secondary sellers
• How liquidity can strengthen rather than weaken a cap table

Guest Bio:

Benjamin Black Powerlaw Corp. (Nasdaq: PWRL), Akkadian Ventures, an investment firm focused on growth-stage technology companies and private-company secondary transactions.

Akkadian provides alternative liquidity solutions for entrepreneurs, employees, angel investors, and venture capital funds, giving Ben a distinctive perspective at the intersection of venture capital, growth investing, and the rapidly evolving private secondary market.

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

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Ben Black:

LinkedIn:https://www.linkedin.com/in/benblack/

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 Finally Going Public (7:51) Why the 10-Year VC Fund Model Is Broken (11:41) Why Late-Stage Secondaries Are Getting Overcrowded (14:47) The Information Advantage in Private Markets (17:01) Why Ben Black Built a Public Venture Fund (22:38) What He Learned After Taking Venture Capital Public (26:52) Who Is Actually Investing in Public Venture Funds? (31:49) Why Startups Are Warming Up to Public VC Funds (38:17) How to Get Access to the Hottest Private Companies

Most venture firms think AI is another productivity tool. David sits down with John Melas-Kyriazi co-founder and CEO of Standard Metrics—the AI-native portfolio management platform used by leading venture capital and private equity firms—to discuss how AI is transforming every stage of investing, from sourcing and diligence to portfolio management, follow-on decisions, and firm operations. John explains why the best venture firms are becoming AI-native organizations, how investors are using large language models today, why every investment memo should be "red teamed" by AI, the rise of MCPs, when firms should build software versus buy it, what Standard Metrics is seeing across more than 12,000 portfolio companies, and why human judgment will become even more valuable as AI automates everything else.

Highlights:

• How AI is changing every stage of venture investing.
• The AI workflows top VC firms already use every day.
• Why every investment memo should be "red teamed."
• MCPs explained and why they'll reshape enterprise software.
• Build vs. buy: what VC firms should develop internally.
• The surprising data behind today's fastest-growing AI companies.
• Why judgment—not research—becomes the scarce resource.
• How Standard Metrics analyzes thousands of private companies.
• Hiring lessons from building an AI-native company.
• Why culture matters more than tools in the AI era.

Guest Bio:

John Melas-Kyriazi is the co-founder and CEO of Standard Metrics, an AI-powered portfolio management platform trusted by many of the world's leading venture capital and private equity firms. Before founding Standard Metrics, he was an investor at Spark Capital and previously worked as a research scientist at Stanford University. Today, he works with thousands of investors and portfolio companies, giving him a unique perspective on how AI is transforming the future of venture capital.

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

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with John Melas-Kyriazi:

LinkedIn:https://www.linkedin.com/in/johnmk/

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 AI Will Transform Venture Capital (8:04) The AI Workflows Top VC Firms Use Today (18:31) Build vs. Buy: Where AI Should Replace Software (30:15) What Actually Creates Alpha in the AI Era (43:11) Why the Best Investors Double Down on Winners (53:02) The Future of AI-Native Services Businesses

Most investors spend their careers trying to eliminate risk. David sits down with Alec Litowitz the founder of Qstar Capital, founder and former CEO of Magnetar Capital, and one of Citadel's earliest partners to explore the difference between risk and uncertainty, why adaptability is becoming the world's most valuable skill, how elite investors make decisions when there is no model to follow, and the cultural principles behind building one of the world's leading hedge funds. Alec also shares lessons from building Magnetar, working alongside Ken Griffin during Citadel's early years, hiring exceptional talent, creating organizations that continuously learn, why ego destroys great investing, and the core ideas behind his upcoming book The Adaptability Quotient.

Highlights:

• Why uncertainty creates bigger opportunities than risk.
• The investing framework that built Magnetar Capital.
• Lessons from working with Ken Griffin during Citadel's early years.
• Why adaptability matters more than IQ in the AI era.
• How elite investors update their beliefs without ego.
• Building organizations that learn faster than competitors.
• Why the best decision-makers embrace feedback loops.
• How to identify uncertainty that can actually be resolved.
• The hidden cost of certainty in investing and business.
• Why great investors think in systems, not predictions.

Guest Bio:

Alec Litowitz is the founder of Qstar Capital and founder and former CEO of Magnetar Capital, one of the world's leading alternative asset managers. Previously, he was one of the four original partners at Citadel Investment Group, where he led Global Equities. He is the author of the forthcoming book The Adaptability Quotient, which argues that adaptability—not IQ or EQ—will become the defining competitive advantage in an increasingly uncertain world. He also founded Magnetar Academy, serves on multiple educational initiatives, and holds degrees from MIT and the University of Chicago.

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

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Alec Litowitz:

LinkedIn:https://www.linkedin.com/in/aleclitowitz/ Book: https://www.theaqbook.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 Most Investors Misunderstand Risk (6:58) How to Profit From Uncertainty Before Everyone Else (15:04) The Adaptability Mindset That Built Magnetar (24:36) Why Great Investors Change Their Minds Faster (34:02) Building a Culture of Excellence Without Ego (44:21) The Hiring Traits That Matter More Than IQ (54:47) Can You Teach Drive or Is It Innate?

Why do the largest investment firms keep getting bigger? David sits down with Joel Holsinger, Co-Head of Ares Alternative Credit, to discuss why scale has become one of the biggest competitive advantages in investing, how Ares evaluates multi-billion-dollar opportunities, why data centers and AI infrastructure are reshaping private credit, and how great investors think about downside protection. Joel also shares the leadership principles behind building world-class investment teams, why reputation compounds like capital, the power of Kaizen, and how Ares' Pathfinder funds have connected institutional investing with large-scale philanthropy through Promote Giving.

Highlights:

• Why scale has become the biggest moat in private markets.
• How Ares thinks about AI infrastructure and data centers.
• The hidden advantage of having a trusted reputation.
• Why great investors obsess over downside protection.
• Joel's "Kaizen" framework for building elite investment teams.
• How Ares combines investing with large-scale philanthropy.
• Why visualization improves investment decisions.
• The biggest career mistake young investors make.
• Why intellectual property matters more than salary.
• The timeless investing advice Joel would give his younger self.

Guest Bio:

Joel Holsinger is Co-Head of Ares Alternative Credit and a member of the Ares Operating Committee. He oversees one of the world's leading asset-based finance platforms and serves as Portfolio Manager for the Pathfinder fund family, which pioneered a model of donating a portion of carried interest to global health and education initiatives through Promote Giving. Before joining Ares, Joel was a Partner at Fortress Investment Group and previously a Founding Partner of Atalaya Capital Management. He also serves on several nonprofit and educational boards, including PATH Global Health and the Ares Charitable Foundation.

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

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Joel Holsinger:

LinkedIn:https://www.linkedin.com/in/joel-holsinger-0739a74/

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 the Biggest Investment Firms Keep Winning (4:56) The Moat That Most Investors Overlook (10:41) Why Reputation Beats Price in Finance (16:35) The Hidden Art of Great Dealmaking (22:08) How Elite Investors Build Trust (28:44) The Leadership Secret Behind Ares (34:51) Why Winning Teams Think Long Term (40:18) The Framework That Builds Better Investors (46:09) Build Your Intellectual Property, Not Your Salary (50:07) The Career Advice Every Young Investor Needs

For years, defense investing was considered off limits for most venture capital firms. Today, billions of dollars are flowing into defense startups as AI, drones, autonomy, advanced manufacturing, and national security become some of the biggest investment themes of the decade. David sits down with Jake Chapman, Managing Director at Marque Ventures, to discuss why defense became mainstream, how government procurement is changing, why Anduril and SpaceX transformed venture investing, where the biggest opportunities still exist, and why the next generation of iconic venture-backed companies may be built around national security rather than consumer software.

Highlights:

• Why Silicon Valley suddenly embraced defense investing.
• The Anduril playbook that changed venture capital.
• How SpaceX created an entirely new venture category.
• Why AI is accelerating defense innovation.
• The hidden challenges of selling to the U.S. government.
• Why manufacturing may be the biggest overlooked investment.
• How defense startups compete against Lockheed and Raytheon.
• The future of autonomous warfare.
• Why venture firms are changing their view on defense.
• Jake's optimistic vision for technology, humanity, and the future.

Guest Bio:

Jake Chapman is the Managing Director of Marque Ventures, an early-stage venture capital firm focused on national security and defense technology. He invests across AI, robotics, aerospace, autonomy, quantum computing, semiconductors, manufacturing, biotech, defense, and energy, backing founders building technologies that strengthen American national security. Jake believes technological innovation is the path toward a future of abundance, exploration, and human progress, inspired by Gene Roddenberry's vision of humanity's future while recognizing the importance of maintaining American strength during a period of global geopolitical change.

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

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Jake Chapman:

LinkedIn: https://www.linkedin.com/in/jakechapman/

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 Defense Tech Became Silicon Valley's Hottest Bet (5:28) The $2 Trillion Market Most Investors Miss (11:14) How SpaceX and Anduril Changed Venture Capital (17:02) Why Selling to the Pentagon Is So Difficult (23:46) The Story Behind Defense's "Last Supper" (30:11) How the Best Defense Startups Break Into the Market (37:55) Where the Biggest Defense Opportunities Still Exist (46:20) The Ethical Case for Investing in Defense (54:08) What the Best Defense Founders Do Differently

For decades, fundraising was driven by relationships. Today, it increasingly starts with AI. David sits down with Lex Suvanto, Global CEO of Edelman Smithfield, to discuss how artificial intelligence is changing fundraising, why reputation is becoming one of the most valuable assets for investment firms, how GPs can differentiate themselves in an increasingly crowded market, and why authentic thought leadership may become the biggest competitive advantage in private markets.

Highlights:

• Why AI is becoming every GP's first impression.
• The surprising reason reputation now matters more than returns.
• How the best investment firms differentiate themselves.
• Why thought leadership compounds into fundraising success.
• The role of media in building institutional trust.
• How AI rewards firms with authentic expertise.
• Why every GP needs a clear point of view.
• The biggest communication mistake investment managers make.
• How private markets are adapting to the wealth channel.
• Why trust will become venture capital's most valuable asset.

Guest Bio:

Lex Suvanto is the Global CEO of Edelman Smithfield, where he advises boards, CEOs, and senior executives of leading public and private companies on strategic communications during transformative events, fundraising, shareholder activism, governance, and investor engagement. Over his career, he has advised on hundreds of domestic and cross-border transactions while helping investment firms strengthen their reputation, communicate with investors, and navigate complex situations. Before joining Edelman Smithfield, Lex was a Managing Director at Abernathy MacGregor and previously held strategy and client service leadership roles at Havas across New York, Paris, and London. He earned his MBA from Harvard Business School.

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

We’d like to thank AlphaSense for sponsoring this episode!

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

Stay Connected with David Weisburd:

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

Stay Connected with Lex Suvanto:

LinkedIn:https://www.linkedin.com/in/lex-aleksi-suvanto-40b599/

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 AI Became Every LP's First Impression (5:46) The Branding Mistake Most GPs Still Make (12:00) Why Most Investment Firms Sound the Same (18:34) The Secret to Building Trust Before Performance (24:52) How Smaller GPs Can Beat the Biggest Firms (31:42) The CEO Matters More Than Your Returns (38:10) How Great Firms Find Their Competitive Edge (46:18) Why Every Audience Needs a Different Message (56:07) The Hidden Cost of Playing It Safe (1:03:48) The Skill That Compounds for Decades

Most venture firms are experimenting with AI. Footwork rebuilt the entire firm around it. David sits down with Nikhil Trivedi, Co-Founder & General Partner at Footwork, to explore what an AI-native venture capital firm actually looks like, how autonomous agents are changing sourcing, diligence, portfolio management, and investment decisions, and why judgment and relationships may be the last true competitive advantages in venture capital.

Highlights:

• What an AI-native venture capital firm actually looks like.
• Why Footwork replaced manual CRM work with AI agents.
• The AI systems helping investors make better decisions.
• Why learning speed is becoming the most valuable founder trait.
• How venture firms should approach AI adoption internally.
• Why relationships and judgment will remain the last human advantages.
• How writing a newsletter compounds into better investing.
• Why exceptional startups deserve exceptional investment decisions.
• The fundraising strategy that attracted elite university endowments.
• How AI could fundamentally reshape venture capital over the next decade.

Guest Bio:

Nikhil Trivedi is the Co-Founder and General Partner of Footwork, an early-stage venture capital firm based in San Francisco. He has invested early in companies including Canva, ClassDojo, Frame.io, Athelas, GPTZero, Watershed, Lattice, The Farmer's Dog, and Brigit, among many others. Nikhil was named to the Forbes Midas Seed List in both 2025 and 2026 and is widely recognized for pioneering the concept of an AI-native venture capital firm. He also writes the popular newsletter Next Big Thing, where he shares insights on venture capital, startups, and emerging technologies.

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

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Nikhil Basu Trivedi:

LinkedIn:https://www.linkedin.com/in/nikhilbt/

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 an AI-Native VC Actually Looks Like (3:29) Inside Footwork's AI Operating System (10:28) How to Build an AI-First Organization (16:52) Why Every VC Firm Needs an AI Operator (20:13) Can AI Become an Investment Partner? (23:40) The Future of Venture Capital in an AI World (28:21) Why Writing Compounds as a VC (32:33) How to Build an AI-Native Venture Firm From Scratch (37:19) The Two Things That Compound Most in Venture (47:48) The Biggest Lessons From Footwork's First Two Funds

AI isn't just changing technology—it is reshaping how investment firms create value, evaluate managers, and generate alpha. David sits down with Thomas Scriven, Managing Director University of Pennsylvania Office of Investments, institutional investor with experience across private equity, endowment management, and investment banking, to discuss why AI-native investment firms may outperform traditional firms, how great LPs evaluate GPs, why concentrated portfolios often outperform diversification, and the investing frameworks that separate elite allocators from everyone else.

Highlights:

• Why AI-native private equity firms have a structural advantage.
• The framework Thomas uses to evaluate every GP.
• Why concentrated portfolios often outperform diversification.
• The hidden importance of incentives between LPs and GPs.
• How AI is changing operational value creation.
• Why thinking time is one of an investor's biggest competitive advantages.
• The mistake allocators make by overprotecting the downside.
• Why the best venture firms continue attracting elite founders.
• How secondaries have transformed institutional portfolio construction.
• The advice Thomas would give himself starting over today.

Guest Bio:

Thomas Scriven Managing Director University of Pennsylvania Office of Investments, institutional investor with more than 15 years of experience spanning private equity, endowment management, investment banking, mergers and acquisitions, portfolio construction, and special situations investing. During his career, he has helped build one of the world's leading university endowment private equity programs while partnering with top-performing venture and buyout firms globally. His investment philosophy emphasizes concentrated conviction, strong GP relationships, operational value creation, and long-term alignment between investors and managers.

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

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Thomas Scriven:

LinkedIn:https://www.linkedin.com/in/thomas-scriven-435281/

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 AI Will Reshape Every Investment Firm (4:12) The AI Playbook That Wins Private Equity Deals (11:48) Why Most Investment Firms Don't Have Enough Thinking Time (18:02) The Hidden Incentives That Drive Every LP and GP (25:06) Frameworks Beat Rules in Investing (33:10) Why Concentrated Portfolios Win (41:02) What Actually Makes a Top Venture Firm (49:17) The Psychology Behind Elite Investors (56:28) AI Will Separate the Winners From Everyone Else (1:04:48) The Investing Lesson Thomas Learned Too Late

Most venture firms are using AI to save time. Earlybird is using it to generate alpha. David sits down with Andre Retterath, General Partner at Earlybird, to discuss how his firm built an AI-native venture platform, why proprietary data is becoming venture capital's biggest competitive advantage, how machine learning improves investment decisions, and why the future of venture belongs to investors who combine technology with exceptional judgment.

Highlights:

• Why AI should automate venture capital—not replace investors.
• The hidden cost of missing great startups.
• How Earlybird built an AI-native investment platform.
• Why founder branding has become a competitive advantage.
• The surprising traits shared by successful AI founders.
• How machine learning improves venture capital decision-making.
• Why the best investors optimize for judgment, not activity.
• The framework Andre uses to evaluate every AI startup.
• How proprietary data creates lasting venture alpha.
• Why exceptional investors spend less time screening and more time thinking.

Guest Bio:

Andre Retterath is a General Partner at Earlybird, where he leads the firm's AI and infrastructure investment practice, focusing on frontier AI models, databases, developer tools, automation platforms, and AI infrastructure. He has led investments in companies including Aleph Alpha, Black Forest Labs, DeepCode, EthonAI, and Energy Robotics, while helping build one of Europe's leading AI-focused venture franchises. Before joining venture capital, Andre worked as a process automation engineer at ThyssenKrupp and as a management consultant at GE. He also earned a Ph.D. from the Technical University of Munich researching machine learning and the value of data in venture capital, research that continues to shape Earlybird's AI-native approach to investing.

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

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Andre Retterath:

LinkedIn:https://www.linkedin.com/in/andreretterath/ Website: https://earlybird.com/ Newsletter: https://datadrivenvc.io/

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 Became Groupthink (3:34) The Portfolio Rule That Cost Them a 50x Winner (7:15) Why Great Fundraisers Keep Winning (10:09) The Founder Traits That Actually Matter (18:26) The Startup Patterns That Never Change (23:15) Why Founder Branding Became a Competitive Advantage (27:44) Inside EarlyBird's AI-Native Venture Platform (34:48) The Hardest Part of Bringing AI Into Venture Capital (1:01:10) Where Alpha Comes From in the AI Era (1:15:59) The Career Advice Andre Wishes He Learned Earlier

Consumer startups may grab the headlines, but some of the most valuable companies are built by solving mission-critical problems for businesses. David sits down with Rick Heitzmann, Managing Director at FirstMark Capital, to discuss how he identifies high-growth technology-enabled business services, why sectors like data infrastructure, compliance, marketing technology, and information services continue to generate outsized opportunities, and what separates enduring enterprise businesses from short-lived trends.

Highlights:

• Why B2B investing remains one of venture's biggest opportunities.
• The characteristics of exceptional enterprise software companies.
• How data has become a competitive advantage.
• Why compliance is creating entirely new categories of startups.
• The evolution of marketing and advertising technology.
• What makes technology-enabled business services highly scalable.
• How recurring revenue creates durable businesses.
• Where Rick sees the next wave of venture-backed winners.
• The investment frameworks FirstMark uses when evaluating founders.
• Why solving critical business problems creates lasting enterprise value.

Guest Bio:

Rick Heitzmann is a Managing Director at FirstMark Capital, where he invests in high-growth emerging media and technology-enabled business services. His investment focus includes data and information management, compliance and risk mitigation, marketing and advertising technology, and business process outsourcing. Rick has built his career identifying scalable enterprise businesses that become critical infrastructure for their customers and benefit from long-term technology adoption.

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

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Rick Heitzmann:

LinkedIn:https://www.linkedin.com/in/rickheitzmann/

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) The Venture Capital Advantage Nobody Can Copy (1:51) Why Relationships Compound Faster Than Capital (8:06) The Hidden Framework Behind Every Great VC Investment (13:07) Why Most Relationships Never Compound (21:23) The AI Trend Almost Everyone Is Missing (25:13) Why the Best Venture Bets Always Look Wrong (35:01) The Founder Test That Predicts Billion-Dollar Companies (47:29) How FirstMark Survived the 2008 Fundraising Crisis (56:06) The Fundraising Lesson That Changed Everything (1:07:48) The One Piece of Advice Every Investor Needs