E407: Why Venture Capital is Becoming a Winner-Take All Market

E411: How AI Is Creating a New Generation of Venture Firms

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 david@weisburdcapital.com [david@weisburdcapital.com]. 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/ [https://www.alpha-sense.com/howiinvest/] to learn more. STAY CONNECTED WITH DAVID WEISBURD: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ [https://www.linkedin.com/in/dweisburd/] Weisburd Pierce: https://www.weisburdcapital.com/ [https://www.weisburdcapital.com/] STAY CONNECTED WITH ANDRE RETTERATH: LinkedIn:https://www.linkedin.com/in/andreretterath/ [https://www.linkedin.com/in/andreretterath/] Website: https://earlybird.com/ [https://earlybird.com/] Newsletter: https://datadrivenvc.io/ [https://datadrivenvc.io/] Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com [david@weisburdcapital.com]. 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

E410: How Relationships Built a $3.6B Venture Firm

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 david@weisburdcapital.com [david@weisburdcapital.com]. 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/ [https://www.alpha-sense.com/howiinvest/] to learn more. STAY CONNECTED WITH DAVID WEISBURD: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ [https://www.linkedin.com/in/dweisburd/] Weisburd Pierce: https://www.weisburdcapital.com/ [https://www.weisburdcapital.com/] STAY CONNECTED WITH RICK HEITZMANN: LinkedIn:https://www.linkedin.com/in/rickheitzmann/ [https://www.linkedin.com/in/rickheitzmann/] Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com [david@weisburdcapital.com]. 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

E409: The Leadership Lessons That Built a $6.5 Billion Firm

Most investors chase what's exciting. Jason Koenig built a $6.5 billion firm by investing where almost nobody was looking. In this conversation, Jason explains why overlooked industrial assets can produce exceptional long-term returns, how ITE grew from $60 million to $6.5 billion in assets under management, why culture compounds just like capital, and the leadership lessons he learned while scaling an investment firm from startup to institutional platform. HIGHLIGHTS: * Why the best investments are often hiding in overlooked industries. * How Jason spotted a billion-dollar opportunity by watching trains. * The founder mindset required to build conviction before everyone else. * Why culture becomes a firm's biggest competitive advantage as it scales. * The leadership framework behind hiring years before you actually need people. * Why compensation should reward teamwork, not individual empires. * The psychology every great investor must understand. * Lessons from negotiating against Carl Icahn. * Why entrepreneurs need both conviction and humility. * The career advice Jason wishes he had followed much earlier. GUEST BIO: Jason Koenig is the Founder, Managing Partner at ITE Management, an investment firm specializing in transportation infrastructure and industrial real assets. Since founding the firm in 2013, he has grown ITE from a startup into a platform managing $6.5 billion in assets, with approximately $13.5 billion of assets owned and managed. Before launching ITE, Jason held investing and legal roles at Avenue Capital, Hale Capital Management, Kirkland & Ellis, Latham & Watkins, and Cooley. He earned an MBA from the Wharton School and graduate degrees from the University of Michigan. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com [david@weisburdcapital.com]. 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/ [https://www.alpha-sense.com/howiinvest/] to learn more. STAY CONNECTED WITH DAVID WEISBURD: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ [https://www.linkedin.com/in/dweisburd/] Weisburd Pierce: https://www.weisburdcapital.com/ [https://www.weisburdcapital.com/] STAY CONNECTED WITH JASON KOENIG: LinkedIn:https://www.linkedin.com/in/jason-koenig-goblue/ [https://www.linkedin.com/in/jason-koenig-goblue/] Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com [david@weisburdcapital.com]. 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 Everyone Ignored a $6.5B Opportunity (2:46) From $60M to $6.5 Billion AUM (8:34) The Entrepreneur's V-Shaped Ego (15:17) Why Great Leaders Need Humility (25:13) The Hardest Part of Scaling a Firm (31:09) Hire 3 Years Before You Need Them (35:02) The Best Career Pattern for Leaders (43:37) How Great Cultures Police Themselves (46:19) Why Investing Is Really Psychology (57:02) The Career Advice Everyone Gets Wrong

E408: HarbourVest: Why Venture Capital Is Chasing Trillion-Dollar Companies

Venture capital isn't about avoiding losses. It's about owning the handful of companies that change everything. Scott explains why HarbourVest has built its venture strategy around power laws, why secondaries have become essential to modern venture investing, and how institutions evaluate managers, partners, and companies across thousands of investment opportunities. HIGHLIGHTS: * Why accepting losses is the price of capturing venture's biggest winners. * The data behind why 10% of companies generate 90% of industry returns. * How secondaries allow LPs and GPs to stay invested in generational companies. * Why some of the best venture funds intentionally extend beyond their original 10-year life. * Why great venture investments almost always look "too expensive" at the time. * How HarbourVest evaluates individual partners instead of just venture firms. * The subtle signals Scott looks for when conducting GP references. * Why diversification across vintages matters more than trying to time venture cycles. * How HarbourVest believes venture investing will evolve over the next decade. GUEST BIO: Scott Voss is a Partner at HarbourVest, a $160B multi-manager private equity firm, where he leads venture and co-investment strategies. With 27 years at the firm, he has helped scale HarbourVest from $150M to $160B AUM, pioneering the firm’s secondary, direct, and continuation vehicle strategies. Scott specializes in portfolio construction, private market diversification, and building long-term strategic GP relationships to generate repeatable alpha. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com [david@weisburdcapital.com]. 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/ [https://www.alpha-sense.com/howiinvest/] to learn more. STAY CONNECTED WITH DAVID WEISBURD: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ [https://www.linkedin.com/in/dweisburd/] Weisburd Pierce: https://www.weisburdcapital.com/ [https://www.weisburdcapital.com/] STAY CONNECTED WITH SCOTT C. VOSS: LinkedIn: https://www.linkedin.com/in/scott-voss-b91b94/ [https://www.linkedin.com/in/scott-voss-b91b94/] Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com [david@weisburdcapital.com]. DISCLAIMER: HarbourVest Partners, LLC is a registered investment adviser under the Investment Advisers Act of 1940. This material is solely for informational purposes and should not be viewed as a current or past recommendation or an offer to sell or the solicitation to buy securities or adopt any investment strategy. The opinions expressed herein represent the current, good faith views of the author(s) at the time of publication, are not definitive investment advice, and should not be relied upon as such. This material has been developed internally and/or obtained from sources believed to be reliable; however, HarbourVest does not guarantee the accuracy, adequacy or completeness of such information. There is no assurance that any events or projections will occur, and outcomes may be significantly different than the opinions shown here. This information, including any projections concerning financial market performance, is based on current market conditions, which will fluctuate and may be superseded by subsequent market events or for other reasons. The information contained herein must be kept strictly confidential and may not be reproduced or redistributed in any format without the express written approval of HarbourVest. Nothing herein should be construed as a solicitation, offer, recommendation, representation of suitability, legal advice, tax advice, or endorsement of any security or investment and should not be relied upon by you in evaluating the merits of investing in HarbourVest funds or in any other investment decision. (0:00) Why Venture Capital Is a Power Law Business (2:08) The Liquidity Decision That Can Make or Break a Fund (5:33) Why Great Investors Keep Underestimating Their Biggest Winners (8:54) The Hardest Truth Every Venture Investor Must Accept (12:49) Why Consensus Investing Rarely Creates Outlier Returns (15:20) The Secret Behind HarbourVest’s Three-Pronged Venture Strategy (21:04) Why HarbourVest Tracks Individual Partners Instead of Just Firms (29:54) How Elite Venture Firms Quietly Lose Their Edge (33:49) What to Do If You Can’t Access Top-Tier Venture Funds (36:20) What Venture Capital Will Look Like in 10 Years

E407: Why Venture Capital is Becoming a Winner-Take All Market

Venture capital has never been more competitive. Aram Verdian argues it has also never been more concentrated. Drawing on Accolade Partners' research across more than 3,000 U.S. venture firms, Aram explains why fewer than 20 firms have consistently produced 3x net returns, what separates the firms that keep winning, and why venture is increasingly becoming a winner-take-all business. From portfolio construction and manager selection to AI, late-stage investing, and fund sizing, he shares the framework his team uses to identify the next generation of exceptional venture firms. HIGHLIGHTS: * Why fewer than 1% of venture firms consistently outperform public markets. * The data behind venture capital's winner-take-all dynamics. * Why seed investing has become more competitive than ever before. * The "right to win" framework Aram uses to evaluate emerging managers. * Why many successful seed firms struggle after raising larger funds. * How LPs should think about concentration versus diversification. * Why AI has fundamentally changed venture fundraising and company building. * How private markets continue to delay IPOs and reshape venture returns. * Why great LPs become long-term strategic partners instead of capital providers. * The importance of relationships and culture in building enduring investment firms. GUEST BIO: Aram Verdian is a Partner at Accolade Partners, where he focuses on venture capital fund investments, growth equity, and digital assets. Previously, he invested at Andreessen Horowitz and earlier spent several years at Accolade before returning as Partner. Today, he helps oversee more than $3 billion in assets under management while leading the firm's blockchain initiatives and identifying emerging venture managers capable of generating long-term, top-decile returns. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com [david@weisburdcapital.com]. 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/ [https://www.alpha-sense.com/howiinvest/] to learn more. STAY CONNECTED WITH DAVID WEISBURD: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ [https://www.linkedin.com/in/dweisburd/] Weisburd Pierce: https://www.weisburdcapital.com/ [https://www.weisburdcapital.com/] STAY CONNECTED WITH ARAM VERDIYAN: LinkedIn:https://www.linkedin.com/in/aram-verdiyan-8099186/ [https://www.linkedin.com/in/aram-verdiyan-8099186/] Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com [david@weisburdcapital.com]. 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 Only 20 Venture Firms Consistently Win (3:42) The 3X Rule Every LP Should Know (9:07) Why Seed Investing Has Never Been Harder (16:20) The VC Math Behind Billion-Dollar Returns (23:05) Why Great Investments Are So Rare (33:16) Why Consistency Beats One Lucky Fund (38:23) The Secret Behind a VC's "Right to Win" (50:18) Why AI Broke Venture Capital (1:02:09) The Biggest Mistake Investors Make in AI (1:16:25) The Career Advice That Changed Everything