What if the secret to building generational wealth isn’t finding the perfect investment—but finding the right people and holding great businesses for decades? In this episode, I sit down with Jason Pritzker, Managing Director and Vice Chairman of The Pritzker Organization and founder of 53 Stations, to discuss the investing principles that helped shape one of America’s most successful business families. Jason shares the story of how the Pritzker family built its fortune, why long-term ownership creates powerful advantages, and how partnering with exceptional leaders compounds value over time.

Highlights:

• How the Pritzker family built a multi-generational investment empire
• Why finding the right partners matters more than finding the perfect deal
• The advantages of long-term ownership versus constant buying and selling
• Lessons Jason learned transitioning from private equity to venture capital
• Why great founders matter more than investment theses
• How 53 Stations developed its venture investing strategy
• The surprising similarities and differences between PE and venture investing
• Why board structure and governance can make or break a company
• The role of customer introductions as a venture capital value-add
• How family values and upbringing shaped Jason’s investing philosophy

Guest Bio:

Jason Pritzker is Founder and Managing Partner of 53 Stations, the venture arm of The Pritzker Organization, where he also serves as Vice Chairman. Backed by an inaugural $187 million commitment, 53 Stations invests in early-stage technology companies, bringing flexibility and scale to its founder partnerships, building companies that stand the test of time.

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 Jason Pritzker:

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

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 Forgotten Decision That Built the Pritzker Fortune (2:03) Why Picking the Right Partner Matters More Than Any Deal (5:27) The Hidden Flaw in the Traditional Private Equity Playbook (8:48) When Selling a Great Company Actually Makes Sense (11:21) Why Most Family Offices Lose Money in Venture Capital (15:14) The Private Equity Habits That Fail in Venture Investing (18:36) Why Great Founders Matter More Than Great Markets (21:09) The Surprising Advantage Behind 53 Stations’ Investment Strategy (25:04) The Boardroom Mistake That Weakens Startups (36:35) The Career Advice He Wishes He Learned a Decade Earlier

What if the biggest driver of long-term investment success isn't finding better investments, but helping investors avoid their own worst decisions? In this episode, I sit down with Ron Albahary, Chief Investment Officer at LNW, to discuss the unique challenges of managing wealth for taxable investors and why portfolio construction is as much about psychology as it is about finance.

Highlights:

• Why managing investor behavior may be more important than picking investments
• The overlooked tax strategies that compound wealth over decades
• How framing risk in dollars instead of percentages changes decision-making
• Why fewer investment decisions often lead to better outcomes
• Lessons from three decades of market cycles and investment fads
• The role hedge funds and diversifiers play during periods of market stress
• Why some evergreen private market structures are misunderstood by investors
• The case for lower middle market private equity over mega-funds
• How AI is creating hidden concentration risk across portfolios
• Why humility may be one of the most underrated traits in investing

Guest Bio:

Ron Albahary is the Chief Investment Officer of LNW, where he oversees approximately $17 billion in assets and leads the firm's investment strategy across public and private markets. Over a career spanning more than three decades, Ron has served as both a Chief Executive Officer and Chief Investment Officer, helping oversee more than $175 billion in client assets.

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 Ron Albahary:

LinkedIn: https://www.linkedin.com/in/ron-albahary-cfa/

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 Managing Humans Is Harder Than Managing Portfolios (2:19) The Highest-Conviction Ways to Create Wealth Without Taking More Risk (4:13) Why Taxable Investors Need a Different Portfolio Playbook (7:34) The Portable Alpha Mistake Investors Keep Repeating (11:01) The Simple Question That Reveals Someone’s True Risk Tolerance (15:56) Why Illiquidity Can Be a Feature, Not a Bug (20:23) The Counterintuitive Reason Great Investors Make Fewer Decisions (25:10) Will Retail Capital Destroy the Private Equity Illiquidity Premium? (33:40) Why Lower Middle Market May Be the Best Place to Find Alpha (42:54) How to Build a Portfolio That Isn’t Dependent on AI

What if the best venture investors aren’t chasing the hottest sectors—but the founders who would still be working on the problem long after the hype disappears? In this episode, I sit down with Ron Rofé, Co-Founder and General Partner of Rainfall Ventures, to discuss why founder quality matters more than industry trends, how non-consensus investing creates outsized opportunities, and what he has learned from backing over 120 startups and 230 founders. Ron shares the stories behind investments like Robinhood, Webflow, and Alma, explains why he prioritizes resilience over ideas, and discusses the founder traits that consistently predict success.

Highlights:

• Why Ron avoids chasing consensus investment themes, including AI
• The founder traits that matter more than market size or industry
• How Rainfall backed Robinhood before it became a fintech giant
• Why resilience often matters more than the original business idea
• The surprising advantage of investing in non-consensus markets
• How great founders balance conviction with humility
• Why half of venture value is created before categories are fully recognized
• The networking philosophy that helped build Rainfall Ventures
• How helping founders creates long-term investing advantages
• Ron’s timeless advice: “Nobody knows anything”

Guest Bio:

Ron Rofé is the Co-Founder and General Partner of Rainfall Ventures, an early-stage venture capital firm that has backed category-defining companies including Robinhood, Webflow, Alma, and Harmonic. Over the past decade, Ron has invested in more than 120 startups representing over 230 founders, building a reputation for making non-consensus bets and identifying exceptional entrepreneurs before the market recognizes them.

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 Ron Rofé:

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

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 He Refuses to Be an AI-Only Investor (3:23) The Opportunity Cost Most Venture Capitalists Ignore (6:04) Why Half of Venture Returns Are Created Before a Market Has a Name (10:08) The Founder Trait That Matters More Than Intelligence (14:10) The Five Qualities He Looks for Before Writing a Check (17:32) How One Founder’s Humility Created a Billion-Dollar Outcome (22:28) The Unusual Way He Got Into Robinhood Before It Took Off (25:52) Why He Invested at a $300M Valuation When Everyone Thought He Was Crazy (31:46) The Hidden Flaw in Thesis-Driven Venture Capital (37:34) The Advice That Changed How He Thinks About Success

What happens when one investor sits at the intersection of venture capital, natural resources, AI, space infrastructure, and geopolitics? In this episode, I sit down with Rob Stephens, Director of Investments at Spider Management, to discuss how institutional investors are adapting to a world where private markets are capturing more value, AI is reshaping capital allocation, and the boundaries between asset classes are disappearing. Rob shares lessons from both the GP and LP sides of the table, explains why traditional portfolio construction frameworks may be outdated, and explores how themes like power generation, data centers, space infrastructure, and venture capital are becoming increasingly interconnected. We also discuss emerging managers, co-investments, continuation vehicles, concentration versus diversification, and the future of private markets.

Highlights:

• How experience as both a GP and LP changes investment decision-making
• Why traditional asset allocation buckets may no longer reflect reality
• The growing divide between investors with access to elite private companies and everyone else
• Why Anthropic, OpenAI, and SpaceX are reshaping private market investing
• The rise of venture co-investments and SPVs
• How LPs evaluate alignment when reviewing co-investment opportunities
• Why references matter more than track records when evaluating spinout managers
• The debate between concentration and diversification in institutional portfolios
• How AI, power generation, natural resources, and venture capital are becoming deeply interconnected
• Why data centers, energy infrastructure, and even space-based computing may become major investment themes

Guest Bio:

Rob Stephens is Director of Investments at Spider Management, the University of Richmond’s $7 billion investment office and OCIO platform. He leads investments across venture capital, private equity, real assets, and thematic public market strategies, with a focus on deep tech, space, defense, AI, energy, natural resources, and China. Prior to joining Spider in 2022, Rob was a Managing Director at DAC Management in Hong Kong and New York, where he specialized in Chinese markets and cross-border 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 Rob Stephens:

Spider Management Company: https://spiderinvests.com/ LinkedIn: https://www.linkedin.com/in/robstephens3/ X/Twitter: @robstephens_

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 GPs Hide That Most LPs Never Notice (2:26) Why Traditional Asset Allocation Is Starting to Break (4:11) Will OpenAI, Anthropic, and SpaceX Fix Venture’s DPI Problem? (6:29) Why Emerging Managers May Struggle More Than Ever (9:05) The Capital Moat Protecting Tier 1 Venture Firms (11:08) The Unusual LP Model That Forces Extreme Alignment (15:08) Why Venture Firms Are Launching More SPVs Than Ever (24:23) Is Venture Capital Heading Toward an Extinction Event? (37:56) Why AI Is Turning Venture Capital Into a Natural Resources Bet (47:52) Can the Biggest Private Companies Stay Private Forever?

What if the biggest edge in investing today isn't having more information—but knowing how to turn information into conviction? In this episode, I sit down with Matt Wells to discuss how AI is reshaping the investment process, why investors are drowning in data but starving for conviction, and where information alpha still exists in increasingly efficient markets. Matt explains the evolution of expert networks, how the best investors use expert calls and channel checks to build differentiated insights, and why qualitative information often drives quantitative outcomes. We also explore decision-grade AI, conviction building, private market diligence, and how the role of the analyst is changing in an AI-driven world.

Highlights:

• Why investors today are drowning in data but starving for conviction
• The difference between information and decision-grade intelligence
• How expert calls evolved from niche hedge fund tools into scalable research platforms
• Why qualitative signals often become quantitative outcomes
• The role of channel checks in forecasting company performance
• How AI can help identify patterns across thousands of expert conversations
• Why conviction matters more than information during periods of volatility
• The future of analysts as architects rather than spreadsheet builders
• How grounded AI differs from general-purpose AI models
• Why human relationships remain irreplaceable in investing and business

Guest Bio:

Matt Wells is a technology executive and entrepreneur focused on applying artificial intelligence and market intelligence tools to investment research and decision-making. Prior to joining AlphaSense, he founded and scaled multiple businesses, bringing a unique operator's perspective to financial technology and research workflows. Today, he works at the intersection of AI, expert intelligence, and investment research, helping institutional investors, corporations, and advisors turn overwhelming amounts of information into actionable insights and higher-conviction decisions.

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 Matthew Wells:

LinkedIn: https://www.linkedin.com/in/matthew-wells-932b6a2/

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 Investors Are Drowning in Data but Starving for Conviction (2:04) The Dangerous Problem With AI Nobody Talks About (4:17) How Expert Calls Became a Hidden Edge for Elite Investors (6:54) The SpaceX IPO Research Strategy Most Investors Won’t Use (11:17) How Top Funds Turn Hundreds of Expert Calls Into Alpha (15:58) Why Every Quantitative Model Starts With Qualitative Information (17:39) Where Investment Alpha Will Come From in an AI World (20:11) The Missing Ingredient Behind Every Great Investment Thesis (24:37) Why the Analyst Role Is About to Change Forever (31:34) The Career Advice That Applies to Investing, Sales, and Life

What if the best private equity opportunities are hiding inside businesses that everyone else thinks are too complicated to touch? In this episode, I sit down with Josh Adams, Partner at OpenGate Capital, to discuss why complexity has become one of the firm's greatest competitive advantages. Josh explains how OpenGate built a specialization around corporate carve-outs, why Europe offers more inefficiency than North America, and how operational improvements drive value creation in today's market. We also discuss sourcing, specialization, alignment, decision-making, and why focus has become increasingly important as private equity continues to evolve.

Highlights:

• Why Europe has become a bigger opportunity than North America
• The hidden alpha inside corporate carve-outs and orphaned assets
• Why OpenGate thinks of itself as operational engineers, not financial engineers
• How complexity creates a sustainable competitive advantage
• The sourcing strategy that puts OpenGate in front of deals before they reach market
• Why speed and certainty consistently win transactions
• Lessons learned from Platinum Equity's operating model
• The dangers of chasing trends and losing strategic focus
• Why specialist firms may outperform as private equity consolidates
• How alignment changes investment behavior and decision-making
• The compounding power of relationships throughout a career

Guest Bio:

Josh Adams is a Partner at OpenGate Capital, where he is responsible for origination, execution, fundraising, and firm management, and serves as a member of the firm's Investment Committee. Since joining OpenGate in 2012, he has helped build the firm into one of the leading specialists in complex corporate carve-outs across Europe and North America. Prior to OpenGate, Josh was a Vice President at Platinum Equity, leading the firm's European business development efforts from London. He began his career as an accountant and is a member of the Association of Chartered Certified Accountants (ACCA).

Are you interested in sponsoring an episode? 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 Josh Adams:

LinkedIn: https://www.linkedin.com/in/joshua-m-adams-70602126/

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 Europe Has Become a Bigger Opportunity Than the U.S. (1:30) The Alpha Hidden Inside Complex Corporate Carve-Outs (5:22) How a $30,000 401(k) Became a Billion-Dollar Firm (10:15) The Sourcing Strategy That Wins Deals Before Auctions Begin (15:22) Why Speed and Certainty Beat Bigger Funds (21:01) The Real Reason Platinum Equity Keeps Winning (23:29) Is Private Equity Quietly Turning Into Asset Management? (26:54) Why Smaller Funds Could Outperform for the Next Decade (30:40) The Alignment Test Every GP Should Pass (32:48) The Career Lesson That Compounds More Than Capital

What separates the venture investors who generate extraordinary returns from those who simply participate in the asset class? In this episode, I sit down with Jeff Diehl, Managing Partner and Head of Investments at Adams Street Partners, one of the world's largest private markets investors with more than $70 billion in assets under management. Jeff shares lessons from over four decades of venture investing, including why access to top managers matters more than almost anything else, what 14,000 realized venture exits have taught Adams Street about return generation, and why portfolio construction often matters more than stock picking.

Highlights:

• Why access to top-quartile venture managers is the single most important factor in venture investing
• The data behind venture capital's unmatched persistence of returns
• What Adams Street learned from nearly 14,000 realized venture-backed company exits
• Why just 7% of companies generated 100% of venture gains
• The critical role of portfolio construction and time diversification
• How Adams Street uses co-investments and secondaries to increase exposure to breakout winners
• Why venture capital succession planning is notoriously difficult
• The relationship between incentives, culture, and long-term investment performance
• Whether venture capital is becoming more concentrated among a handful of mega-firms
• Why private markets continue to capture a growing share of global growth opportunities
• Jeff's most expensive investing lesson and why mistakes are essential for becoming a great investor

Guest Bio:

Jeff Diehl is the Managing Partner and Head of Investments at Adams Street Partners, a global private markets investment manager with more than $70 billion in assets under management across private equity and private credit strategies. He oversees the firm's investment activities and overall management while serving as Chairman of both the Portfolio Construction Committee and Executive Committee. Under his leadership, Adams Street has expanded its global footprint to more than 330 professionals across 14 offices worldwide.

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 Jeff Diehl:

LinkedIn: https://www.linkedin.com/in/jeffrey-diehl-63a0701/

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 Two Rules That Explain Almost Every Venture Outcome (0:43) Why Venture Capital Has More Persistence Than Any Other Asset Class (5:01) What 14,000 Exits Taught Him About Venture Returns (7:57) The Shocking Reality: 7% of Companies Create 100% of the Gains (9:22) Why Every Great Venture Co-Investment Starts With GP Relationships (10:33) The Hidden Reason Growth Investors Are Moving Into Private Markets (13:11) Why Succession Fails at Most Venture Capital Firms (16:23) The Culture and Incentive System Behind Top Investment Organizations (24:59) Can Size Become a Moat in Venture Capital? (33:53) The $12 Million Mistake He Still Keeps as a Reminder

What if the biggest opportunity in private markets isn’t finding the next startup—but owning the next public company years before it ever rings the bell? In this episode, I sit down with Matt Witheiler, Head of Late-Stage Growth at Wellington Management, to discuss how the line between public and private markets continues to blur. Matt explains why companies are staying private longer, why public investors are starved for growth, and how late-stage investing differs from both venture capital and public equities. We also explore IPO markets, valuation discipline, liquidity dynamics, and why the best companies often justify paying up for quality.

Highlights:

• Why OpenAI, Anthropic, and SpaceX may reignite the IPO market
• The growing shortage of high-growth companies in public markets
• Why small-cap investing has fundamentally changed over the last decade
• How late-stage investors evaluate hype versus fundamentals
• Why founders optimize for partners, not the highest valuation
• The advantage Wellington brings as both a private and public market investor
• Why valuation discipline matters more than bargain hunting
• Matt’s biggest investing miss and what SpaceX taught him about exceptional founders

Guest Bio:

Matt Witheiler is the Head of Late-Stage Growth at Wellington Management, where he leads the firm’s private company investing activities across technology, healthcare, consumer, and financial services. Since joining Wellington in 2016, he has helped build one of the largest and most respected late-stage growth investing platforms, leveraging the firm’s deep public market expertise to identify future public company leaders. Prior to Wellington, Matt was a General Partner at Flybridge Capital Partners and earlier held operating roles in technology, including co-founding AnandTech.com. He has been named to the Forbes Midas List for six consecutive years and is widely recognized as one of the leading investors at the intersection of private and public markets.

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 Matt Witheiler:

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

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 IPOs in History Won’t Break Public Markets (2:22) The Passive Buying Wave Coming for SpaceX, OpenAI, and Anthropic (3:15) Why Public Investors Are Desperate for New Growth Stories (5:22) How Investors Separate Real AI Companies From AI Hype (7:59) Why Pension Funds Are Buying Private Assets From Public Allocations (9:20) The Hidden Reason Small-Cap Investing Stopped Working (13:13) Why the Best Founders Want to Stay Private Longer (13:44) How Wellington Wins Deals Against Sequoia and Andreessen (18:38) The Secret to Getting Into the Hottest Rounds Before Everyone Else (24:42) The Billion-Dollar Mistake Wellington Made on SpaceX

What if the biggest edge in venture capital isn’t manager selection—but earning access to the managers everyone already knows are the best? In this episode, I sit down with Mark Anson, CEO, President, and CIO of Commonfund, to discuss what he has learned managing capital across some of the world’s most influential institutions, including CalPERS, the Bass Family Office, and Commonfund. Mark explains why venture capital remains one of the most persistent alpha-generating asset classes, how LPs earn access to top managers, and why relationships, responsiveness, and knowledge-sharing matter more than check size. We also explore performance persistence, the illiquidity premium, co-investments, and the lessons Mark has learned managing capital across multiple decades and market cycles.

Highlights:

• The surprising story of how donuts helped unlock access to a top-tier VC fund
• Why venture capital has the greatest performance dispersion in investing
• The difference between average and top-quartile venture returns
• How Commonfund evaluates emerging managers before the market finds them
• Why access in venture is earned, not bought
• The case for a rules-based approach to venture investing
• Why innovation is completely uncorrelated with the business cycle
• Mark’s framework for managing “human capital” throughout a career

Guest Bio:

Mark Anson is the Chief Executive Officer, President, and Chief Investment Officer of Commonfund, where he oversees more than $35 billion in assets serving endowments, foundations, and institutional investors. Throughout his career, Mark has led investment organizations at some of the world’s most prominent institutions, including CalPERS, the Bass Family Office, British Telecom Pension Scheme, Hermes Pension Management, and Nuveen Investments. A prolific author, researcher, and educator, he has published more than 100 journal articles and several leading finance textbooks, including The Handbook of Alternative Assets.

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 Capital: https://www.weisburdcapital.com/

Stay Connected with Mark Anson:

LinkedIn:https://www.linkedin.com/in/mark-anson-7a9b4a75/

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

Disclaimer:

Each of CF Private Equity, Inc. and Commonfund OCIO, Inc. (collectively, “Commonfund”) 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 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 participants at the time of publication, are not investment advice, and should not be relied upon as such. The information discussed herein has been developed internally and/or obtained from sources believed to be reliable; however, Commonfund 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 stated herein. 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.

(0:00) How a Box of Donuts Got CalPERS Into a Top VC Fund (2:35) Why Venture Capital Rewards Failure Differently Than Any Other Asset Class (4:20) The Power Law That Drives Nearly All Venture Returns (8:05) How Commonfund Wins Access to the Best Venture Managers (10:14) How Top LPs Can Approve Venture Deals in Just 48 Hours (11:50) The Secret Process for Finding Tomorrow’s Top VC Funds (15:10) Why Buying Into Carlyle Was Better Than Negotiating Lower Fees (18:37) Is Capital Still a Moat in Venture Capital? (24:38) Why the Biggest Investment Opportunities Happen Every 10 Years (33:31) The Hidden Cost of Companies Staying Private Too Long

What if the biggest investment opportunity of the next decade isn’t AI itself—but the companies building the infrastructure and workflows that allow AI agents to actually do work? In this episode, I sit down with David Blumberg, Founder and Managing Partner of Blumberg Capital, to discuss why he believes agentic AI is still in the first inning of a multi-decade transformation. David explains how AI agents will reshape productivity across industries, why vertical software companies with proprietary data have a major advantage, and how network effects are evolving through AI-powered data flywheels. We also explore the future of work, the rise of AI-native businesses, and why human relationships remain one of the few enduring advantages in an increasingly automated world.

Highlights:

• Why agentic AI could become a larger market than software itself
• The hidden infrastructure needed for AI agents to transact autonomously
• How proprietary data creates durable AI moats
• Why vertical AI companies may outperform general-purpose models
• The concept of AI-powered data flywheels and compounding network effects
• How AI could dramatically increase productivity without eliminating opportunity
• Why the next generation of Fortune 500 companies is being built right now
• The enduring importance of relationships in a technology-driven world

Guest Bio:

David Blumberg is the Founder and Managing Partner of Blumberg Capital, an early-stage venture capital firm focused on backing visionary entrepreneurs building global B2B technology companies. Over a career spanning venture capital, operating leadership, and institutional investing, he has helped build and back category-defining businesses including Nutanix, Braze, DoubleVerify, Trulioo, and Check Point Software Technologies. Prior to founding Blumberg Capital, David held investment roles with Claridge, Apax Partners, Adler & Co., and T. Rowe Price, and was part of the early leadership team at Check Point. He is widely recognized for his focus on enterprise technology, cybersecurity, fintech, and the next wave of AI-driven innovation.

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 Capital: https://www.weisburdcapital.com/

Stay Connected with David Blumberg:

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

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 AI Agents Could Become the Biggest Productivity Shift in History (0:43) Will AI Create More Jobs or Eliminate Them? (5:10) The B2B AI Opportunity Most Investors Still Underestimate (8:07) Why Almost Nobody Uses AI Agents Today (And Why That’s About to Change) (9:22) The $100 Trillion Market Hidden Behind White-Collar Work (12:16) The Infrastructure Layer Every AI Agent Will Need (18:49) The Data Flywheel That Makes AI Companies Hard to Compete Against (20:46) Why Vertical AI Could Beat the Largest LLMs (24:45) The Surprising Opportunity Emerging Managers Have in the AI Boom (28:17) The Career Prediction From the 1970s That’s Finally Coming True

What if the biggest opportunity in venture today isn’t finding the next unicorn—but solving the liquidity problem created by companies staying private twice as long as they used to? In this episode, I sit down with Ravi Viswanathan, Founder and Managing Partner of NewView Capital, to discuss how the venture ecosystem is evolving beyond the traditional fund model. Ravi explains why he left NEA to build a firm focused on liquidity solutions, how company-led secondaries are becoming a critical tool for founders and employees, and why the future of venture may depend on balancing long-term ownership with thoughtful liquidity. We also explore the DPI drought, continuation vehicles, cap table management, and why relationships remain the ultimate source of edge in venture capital.

Highlights:

• Why companies staying private longer created a structural liquidity gap
• The rise of company-led secondaries and founder-controlled liquidity
• How employee liquidity can improve retention and long-term alignment
• Why the venture industry can no longer ignore DPI
• The tension between FOMO investing and long-term conviction
• How continuation vehicles may reshape venture portfolios
• Why capital often masks product-market fit during boom cycles
• The relationship-driven lesson Ravi wishes he learned earlier in his career

Guest Bio:

Ravi Viswanathan is the Founder and Managing Partner of NewView Capital, a growth-stage investment firm managing more than $3 billion and focused on primary, secondary, and hybrid investments in leading technology companies. Prior to founding NewView in 2018, Ravi spent 15 years as a General Partner at NEA, where he backed category-defining companies including MuleSoft, Braintree, Acquia, Cyence, and GlobalLogic. Over more than two decades in venture capital, Ravi has built a reputation for partnering with exceptional founders, identifying enduring technology businesses, and helping shape the evolution of liquidity and capital formation in private markets.

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 Capital: https://www.weisburdcapital.com/

Stay Connected with Ravi Viswanathan:

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

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 He Left NEA to Launch a $1.3 Billion Venture Fund (1:02) Are the Best Venture Companies Already Obvious by Series B? (3:33) The New Secondary Market Trend Reshaping Venture Capital (5:02) Why Employees Need Liquidity Long Before an IPO (7:03) The Hidden Benefits of Letting Employees Sell Shares (11:38) Will OpenAI, Anthropic, and SpaceX Fix Venture’s DPI Crisis? (13:17) Why Venture Capital May Never Return to Historical DPI Levels (20:18) Are Continuation Vehicles the Next Big Venture Trend? (24:35) The One Thing That Compounded Most Over 25 Years in Venture (28:20) How Easy Money Created an Entire Generation of Zombie Startups