What happens to financial analysts when AI can do the work they used to spend all night doing? Chris Ackerson is SVP of Product at AlphaSense, where he focuses on applying information retrieval, natural language processing, deep learning, and recommendation systems to search and discovery. We discuss how AI is changing the analyst role, why vertical AI can outperform general-purpose models in financial research, and why proprietary data may become one of the most important competitive advantages in AI. Chris also explains why LLMs hallucinate, how AlphaSense is using AI to conduct expert interviews, where humans still create investment alpha, and why the future of financial research may look less like software and more like an AI teammate that never sleeps.

Highlights:

• How AI is changing the role of financial analysts
• How AlphaSense increased banker coverage by up to 15% in one case study
• Why vertical AI can outperform general-purpose models in financial research
• Why hallucinations remain a barrier to professional AI adoption
• Why proprietary data could become a defining AI advantage
• How AI agents are conducting expert interviews and channel checks
• What investment bankers and hedge fund analysts may do in five years
• Why human judgment becomes more valuable as AI improves
• Where investment alpha comes from if everyone has access to similar AI
• Why frontier AI models are becoming more specialized, not less
• How AI agents could become teammates that work 24/7
• Why AI companies must constantly be willing to disrupt themselves

Guest Bio:

Chris Ackerson is SVP of Product at AlphaSense and an experienced product leader focused on applying innovations in information retrieval, natural language processing, deep learning, and recommendation systems to search and discovery.

Sponsors:

Juniper Square:

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

AlphaSense:

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

AlphaSummit Discount Code: AS26HII50

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

Stay Connected with David Weisburd:

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

Stay Connected with Chris Ackerson:

LinkedIn:https://www.linkedin.com/in/chris-ackerson-965b1313/

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) Will AI Replace Financial Analysts? (3:00) Why Vertical AI Could Beat General-Purpose Models (6:28) Why Do LLMs Hallucinate? (7:50) Why Proprietary Data Matters More in AI (10:58) How AI Can Interview Human Experts (14:11) What Finance Jobs Could Look Like in Five Years (17:23) If Everyone Has AI, Where Does Alpha Come From? (20:32) Why AI Models Are Becoming More Specialized (27:16) What Happens When AI Agents Work With Other Agents? (30:57) The AI Lesson Chris Wishes He Learned Earlier

Is private credit really in a bubble, or are investors looking for risk in the wrong place? Theodore “Ted” Koenig is Chairman and CEO of Monroe Capital, a $24 billion private credit firm. We break down how private credit grew from a niche alternative to a $2 trillion asset class, why financing shifted from banks to private credit after the financial crisis, and the two ways Ted believes lenders can generate alpha. We also discuss the flood of retail capital into private credit, why Monroe focuses on the lower middle market, the dangers of prioritizing AUM growth over investor returns, and the personal drive and tradeoffs behind building Monroe.

Highlights:

• How Ted spotted the opportunity in private credit before it became an asset class.
• Why the financial crisis permanently shifted lending away from banks.
• The two ways Ted believes private credit managers can generate alpha.
• Why Monroe built its moat around lower middle-market companies.
• Why Ted expects private credit to grow from $2 trillion to $5 trillion.
• What the surge of retail capital means for the future of private credit.
• Why Ted believes the greater risk today may actually sit in private equity.
• The personal tradeoff Ted made while building Monroe Capital.

Guest Bio:

Theodore L. “Ted” Koenig is Chairman and CEO of Monroe Capital LLC. He founded Monroe in 2004 after previously serving as President and CEO of Hilco Capital LP. Ted also co-founded HOPE Chicago and has received lifetime achievement recognition from the Association for Corporate Growth Midwest and SFNet, as well as recognition from Private Debt Investor as one of the top changemakers in private credit. He earned a B.S. in accounting with high honors from Indiana University’s Kelley School of Business and a J.D. with honors from Chicago-Kent College of Law.

Sponsors:

Juniper Square:

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

AlphaSense:

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

AlphaSummit Discount Code: AS26HII50

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

Stay Connected with David Weisburd:

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

Stay Connected with Ted Koenig:

LinkedIn:http://linkedin.com/in/theodore-koenig

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

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) How Ted Saw Private Credit Before Everyone Else (3:18) What Keeps Him Building After $24 Billion (5:30) Why the Best Entrepreneurs Never Stop Competing (9:09) The Story Behind Ted’s Relentless Drive (13:36) How Private Credit Became a $2 Trillion Market (20:50) The Only Two Ways to Generate Alpha in Private Credit (24:16) Is Private Credit Actually in a Bubble? (30:30) Why Retail Investors Are Flooding Into Private Credit (35:13) The Problem With Chasing AUM Instead of Returns (42:46) The Personal Cost of Building a $24 Billion Firm

What if the best reason to start a company isn’t to change the world, but simply because you love the game? In this episode, I sit down with Marty Kausas, CEO of Pylon, to unpack how he thinks about building an ambitious company from first principles. Marty explains why Pylon started with a goal of reaching $1 billion in revenue, why market size can matter more than the quality of the founding team, and why the rise of AI has pushed his definition of a generational company even higher.

Highlights:

• Why Marty started Pylon for “fun and adventure.”
• Why market selection can matter more than the founding team.
• How Pylon’s ambition grew from $1B in revenue to a $1T valuation.
• Why Marty believes AI replacement is the wrong startup thesis.
• What it really means for a support team to “go agentic.”
• Why great founders may be overestimating incumbent software companies.
• How category creation can become a company’s biggest marketing advantage.
• Marty’s biggest mistake transitioning from engineer to CEO.

Guest Bio:

Marty Kausas is CEO and Co-Founder of Pylon, where he is building a next-generation customer support platform for B2B companies and helping support teams transition toward agentic workflows. Before founding Pylon, Marty held an engineering role at Airbnb, invested through Andreessen Horowitz’s scout fund, and completed software engineering internships at Yelp and Qualcomm.

Sponsors:

Juniper Square:

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

AlphaSense:

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

AlphaSummit Discount Code: AS26HII50

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

Stay Connected with David Weisburd:

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

Stay Connected with Marty Kausas:

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

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 Marty Started Pylon for “Fun and Adventure” (4:00) Why Market Matters More Than the Founding Team (8:00) The Greatest Gift a Founder Can Give Their Company (12:00) Why Building a Huge Company Can Actually Be Easier (16:00) Pylon’s New Goal: Build a Trillion-Dollar Company (20:00) Why Marty Thinks AI Won’t Replace Humans (24:00) What It Really Means to “Go Agentic” (31:00) Why the Best Startup Ideas Don’t Sound Serious (36:00) The Underrated Trait Marty Looks for When Hiring (44:00) Marty’s Biggest Mistake as a First-Time CEO

What if AI makes talent, not technology, the biggest competitive advantage in private equity? Michael Bruun is Partner and Global Co-Head of Private Equity within Goldman Sachs Asset Management. We break down how Goldman Sachs competes for the best middle-market assets, why Michael believes talent can move the needle more than almost anything else, and how higher rates have forced private equity back to the fundamentals of EBITDA and cash-flow growth. We also discuss how Goldman is implementing AI across portfolio companies, why transformation must start with the CEO, and why the war for exceptional talent may become even more important as every employee becomes AI-enabled.

Highlights:

• How Goldman Sachs competes for the best middle-market assets.
• Why more than 110 operating partners can create a talent advantage.
• Why private equity’s value-creation playbook works best during volatility.
• How higher rates forced private equity to return to fundamentals.
• Why the best exits may depend on what never appears in the financial statements.
• How Goldman thinks about continuation vehicles versus strategic exits.
• The two outcomes Michael wants from every AI initiative.
• Why AI transformation has to start with the CEO.

Guest Bio:

Michael Bruun is Partner and Global Co-Head of Private Equity within Goldman Sachs Asset Management, which he joined in 2004. He is a member of several investment committees across Asset Management and previously served as Head of EMEA Private Equity and Head of Private Equity and Growth Equity investing for India. Michael earned bachelor’s and master’s degrees in economics from the University of Copenhagen, with studies at Cornell University. He currently serves on the Boards of Directors of Advania, GS Wyvern, LRQA, and Norgine and previously served on the Board of Directors of Northvolt

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 Michael Bruun:

LinkedIn: https://www.linkedin.com/in/michael-bruun-486883/

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 Transformation Has to Start With the CEO (1:39) Why Goldman Sachs Believes in “Skin in the Game” (3:38) How Goldman Competes for the Best Private Equity Deals (7:17) Why Talent Compounds Better Than Ideas (9:17) Why Volatility Creates an Operating Advantage (13:20) What Higher Rates Changed in Private Equity (15:36) The Value That Never Shows Up in a Spreadsheet (18:14) Should Great PE Assets Ever Be Sold? (22:09) How AI Is Actually Changing Portfolio Companies (28:32) The AI Implementation Playbook That Starts at the Top

What if the biggest mistake in venture capital is investing in what already looks like a great venture investment? In this episode, I sit down with Dr. V (Vaibhav Agrawal), Founder ODDBIRD VC, is a San Francisco-based venture investor who spent nearly a decade at Lightspeed, to explore why he believes the traditional venture playbook is changing. Sourcing has become a media and distribution business, companies are staying private longer, and investors increasingly need to think proactively about liquidity rather than simply waiting for their winners to go public.

Highlights:

• Why the old venture capital playbook no longer works.
• How sourcing became a media and distribution business.
• Why liquidity management is becoming a core skill for venture firms.
• How fund growth can quietly create strategy drift.
• Why markups can turn venture investors into momentum traders.
• Why Dr. V believes early-stage investing requires finding “pattern breakers.”
• Why consumer and fintech may be systematically oversold today.
• The overlooked opportunity in “fresh off the boat” founders.

Guest Bio:

Dr. V (Vaibhav Agrawal) Founder ODDBIRD VC, is a San Francisco-based venture investor who spent nearly a decade at Lightspeed before spinning out to build his own venture firm. Originally trained in medicine, he has developed an investing philosophy centered on finding exceptional founders and opportunities before they fit established patterns.

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 withDr.V (Vaibhav Agrawal):

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

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 May Still Be Undervalued (3:13) Why the Old VC Playbook No Longer Works (6:57) Who Will Buy Venture’s Illiquid Assets? (10:51) Why Dr. V Refuses to Invest Outside Venture (14:38) When Bigger Funds Lose Their Edge (16:21) The Hidden Bias Driving Venture Investors (20:58) Why Early-Stage Investors Need Pattern Breakers (21:44) Why Dr. V “Chases Chaos” (27:18) The Venture Categories Everyone May Be Underestimating (30:30) Why “Fresh Off the Boat” Founders May Be Mispriced

What if passive investing is actually one of the biggest active forces shaping markets today? In this episode, I sit down with Michael Green, Founder and CIO at Tier1 Alpha Asset Management. Michael challenges the conventional view that stock prices primarily reflect fundamentals, arguing that the transaction itself moves prices and that the rise of passive investing has fundamentally changed who trades, why they trade, and how markets respond to capital flows.

Highlights:

• Why Michael believes passive investing isn’t actually passive.
• The Peter Thiel question that changed how Michael evaluates consensus.
• Why transactions and flows may matter more to prices than fundamentals.
• How index inclusion can create powerful self-reinforcing feedback loops.
• Why passive investing may be making the biggest companies even bigger.
• How leveraged ETFs can amplify both rallies and selloffs.
• Why Michael believes traditional value factors are fighting against passive flows.
• What happens when automatic retirement inflows eventually become outflows.

Guest Bio:

Michael Green is Founder and CIO at Tier1 Alpha Asset Management. He founded and ran Canyon Capital Advisors’ New York office, where he built global macro strategies covering more than $5 billion of exposure across equities, credit, FX, and commodities. He later founded Ice Farm Capital, a discretionary global macro hedge fund seeded by Soros Fund Management, and managed macro strategies at Thiel Macro.

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 Michael Green:

LinkedIn:https://www.linkedin.com/in/michael-green-9a15142/

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 Peter Thiel Taught Michael About Being Contrarian (4:18) Why Stock Prices May Have Less to Do With Fundamentals (9:18) The $1 Flow That Could Create $22 of Market Value (14:37) How Leveraged ETFs Can Amplify the Market (20:01) Why Passive Investing May Be a Systemic Risk (25:46) The Market Signal Michael Says Everyone Is Missing (31:34) Why Passive Flows Keep Making the Biggest Stocks Bigger (36:36) Why Traditional Factor Investing May Be Breaking (42:05) How Market Makers Became the New Alpha Winners (44:04) What Happens When Passive Inflows Reverse

Peter Hecht, Managing Director at AQR Capital Management, explains why diversification has to be measured by underlying risk rather than the number of investments you own. At AQR, diversification is a core principle: thousands of relatively small, uncorrelated investment decisions can collectively create an attractive return for a given level of risk.

Highlights:

• Why tracking error is necessary if you actually want to beat a benchmark.
• How AQR thinks about diversification like a casino playing thousands of independent hands.
• Why “alpha” has no single universal definition.
• What Eugene Fama taught Pete about separating alpha from compensated risk.
• Why AQR uses AI differently from simply asking ChatGPT or Claude which stocks to buy.
• How a systematic investor can succeed while being wrong roughly 45% of the time.
• Why 90% of a seemingly diversified portfolio’s risk can still come from equities.
• What 2022 revealed about the hidden weakness of the traditional 60/40 portfolio.
• Why trend following can provide protection without requiring a permanently negative correlation to stocks.
• How portable alpha separates where investors get their market exposure from where they seek alpha.

Guest Bio:

Peter Hecht is a Managing Director at AQR Capital Management, where he advises institutional and other sophisticated investors on portfolio construction, investment strategies, and some of the most challenging questions in asset allocation.

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 Peter Hecht:

LinkedIn: https://www.linkedin.com/in/peter-hecht-ba850215/

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 Tracking Error Isn’t Necessarily Bad (3:00) How AQR Thinks About Diversification (7:00) What Alpha Actually Means (12:00) Eugene Fama, Value and Factor Investing (17:00) How AQR Uses AI and Machine Learning (24:00) What Makes a Great Systematic Investor (30:00) Why Being Right 55% of the Time Is Enough (35:00) The Case for Trend Following (42:00) Why Most Portfolios Are Still Equity Bets

What happens when a private equity firm refuses to chase every new opportunity and spends 30 years getting better at one thing? David sits down with Michael Fisch, co-founder and CEO of American Securities, to unpack how the firm grew from a $71.4 million first fund to $23 billion in AUM without abandoning the investment discipline that got it there. Michael explains how private equity evolved from a sub-$1 billion institutional market into a multi-trillion-dollar industry, why American Securities resisted the temptation to expand into every adjacent asset class, and why seeing more deals matters almost as much as knowing which ones to reject.

Highlights:

• How private equity evolved from a niche strategy into a multi-trillion-dollar industry.
• Why cash flow changed the way Michael thought about buying companies.
• The discipline that helped American Securities scale without chasing adjacent strategies.
• Why the best investors need both a massive deal funnel and a narrow investment filter.
• What Michael learned from knowing Warren Buffett for decades.
• The hiring framework American Securities uses to reduce judgment errors.
• How an 80%+ CEO “win rate” reflects a different approach to private equity ownership.
• Why retail capital could create a new wave of demand for private equity.
• How AI could collapse finance’s traditional analyst pyramid.
• Why “make the call” remains one of Michael’s most important career lessons.

Guest Bio:

Michael Fisch is the co-founder and CEO of American Securities, where he is a member of the Investment Committee and has helped build the firm into a leading private equity platform. American Securities launched its first fund in 1994 with $71.4 million and today manages approximately $23 billion in AUM.

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 Michael Fisch:

LinkedIn: https://www.linkedin.com/in/michaelfisch-americansecurities/

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) Private Equity Barely Existed When Michael Started (4:27) Why He Took the Risk of Starting His Own Fund (9:04) Why Private Equity Is Really a People Business (15:20) The Hiring Mistake Most Leaders Still Make (19:27) What Warren Buffett Taught Him About Staying in Your Lane (22:00) How Saying “No” Helped Build a $23B Firm (31:22) The Operating Advantage Most PE Firms Didn’t Have (35:23) The Secret Behind an 80%+ CEO Win Rate (42:06) The Retail Capital “Tsunami” Coming to Private Equity (47:29) Why AI Makes “Make the Call” More Important Than Ever

David sits down with Byron Ling of Twelve Below to unpack the judgment required to invest at the earliest stages of technology. After roughly 30,000 founder meetings over the past decade, Byron believes the strongest signals rarely appear on a résumé. He looks for an almost biological drive to win, second-level thinking, exceptional learning velocity, clear communication, authenticity, and a sense of urgency that makes a founder difficult to compete against.

Highlights:

• The founder traits that matter more than pedigree or early traction.
• Why a chip on your shoulder can become a competitive advantage.
• How second-level thinking separates exceptional founders from consensus thinkers.
• Why the best founders are learning machines.
• What 30,000 founder meetings taught Byron about pattern recognition.
• Why AI can improve VC sourcing without replacing investment judgment.
• The mistake of underwriting $100B outcomes instead of studying their original inputs.
• Why Byron would tell his younger self to take more risk.

Guest Bio:

Byron Ling is a Partner at Twelve Below, a New York-based venture firm focused on pre-seed and seed technology investing. He began his startup career working with Kevin Ryan at Gilt Groupe before joining the then-first-time fund Primary Venture Partners. He later became a General Partner at multi-stage venture firm Canaan before co-founding Twelve Below with longtime investing collaborator Taylor Greene.

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 Byron Ling:

LinkedIn: https://www.linkedin.com/in/byron-ling-10b7474/

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 Founder Trait You Can’t See on a Résumé (4:18) Why the Most Obsessive Founders Think Differently (9:05) What Zoom Hides About Great Founders (12:50) What 30,000 Founder Meetings Revealed (19:30) Why Young AI Founders Have an Unfair Advantage (27:10) The Strange Opportunity Hidden in Today’s VC Market (33:00) Why Vibe Coding Is Creating a New Investing Problem (44:45) How AI Can Find Great Founders Before Everyone Else

What can 32 years as a university CIO teach you about identifying exceptional investors before everyone else does? David sits down with Scott Malpass, Co-Founder and Managing Partner of Grafton Street Partners and former Chief Investment Officer of the University of Notre Dame, to discuss the patterns he learned from evaluating thousands of investment firms and building decades-long relationships with some of the world’s leading managers.

Highlights:

• Why investing is ultimately a people business.
• The patterns Scott learned from evaluating thousands of investment firms.
• Why the best GPs combine confidence with humility.
• How Scott recognized exceptional managers before their track records made them obvious.
• The story behind Notre Dame’s decades-long relationship with Sequoia Capital.
• Why Scott was willing to pay premium carry for exceptional performance.
• Why capacity rights can be more valuable than lower fees.
• The number one mistake Scott believes ruins investment firms.
• Why many institutional portfolios are more diversified than they need to be.
• How experience makes great investors faster decision-makers.

Guest Bio:

Scott Malpass is Co-Founder and Managing Partner of Grafton Street Partners. Previously, he spent 32 years as Chief Investment Officer of the University of Notre Dame, where he built one of the country’s most respected institutional investment programs and also served as an Adjunct Professor of Finance at the Mendoza College of Business.

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 Scott Malpass:

LinkedIn:https://www.linkedin.com/in/scott-malpass-301545144/

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 #1 Lesson From 32 Years as a CIO (3:18) What the Best Investment Managers Have in Common (8:24) How Notre Dame Helped Build 35% of the Nasdaq (12:05) The Signals That Reveal a Great GP Early (22:11) How a Chance Meeting Led to Sequoia Capital (30:13) Why Great LPs Don’t Obsess Over Fees (33:47) The #1 Thing That Ruins Investment Firms (41:06) Why Notre Dame Made Him CIO at Just 26 (47:49) How Scott Finds Emerging Managers Before Everyone Else (1:01:00) The Investing Lesson He Wishes He Learned Earlier

David sits down with Bryon Hargis, co-founder of Castelion, to unpack why rebuilding America’s defense manufacturing capacity has become a national security imperative. Bryon explains why decades of consolidation and outsourcing weakened the defense industrial base, why America could struggle against an adversary with significantly greater manufacturing capacity, and why Castelion is betting that deterrence ultimately requires weapons that can be produced affordably by the thousands.

Highlights:

• Why America’s defense problem is increasingly a manufacturing problem.
• How the defense industry’s “Last Supper” reshaped the industrial base.
• What Bryon learned about speed and iteration at SpaceX.
• Why “the best part is no part” is more than an Elon Musk catchphrase.
• Why Castelion combines product and sales instead of separating them.
• How mission-driven hiring helps protect culture as a startup scales.
• Why Bryon left SpaceX even when defense hardware was considered nearly uninvestable.
• How Castelion survived almost 100 VC rejections.
• Why one major investor can completely change a startup’s access to capital.
• Inside Castelion’s plan to manufacture hypersonic weapons at massive scale.

Guest Bio:

Bryon Hargis is the co-founder of Castelion, a defense technology company focused on developing and manufacturing advanced hypersonic weapon systems in the United States. Before founding Castelion, Bryon worked at SpaceX, including on the Starshield program and in government satellite sales. His work focused on applying SpaceX capabilities to national security problems, an experience that helped shape Castelion’s hardware-first and customer-driven approach.

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 Bryon Hargis:

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

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 America Needs Hypersonic Missiles (3:00) How Defense Manufacturing Lost Its Edge (5:30) What SpaceX Taught Bryon About Building Hardware (10:00) Why Product and Sales Should Be the Same Team (15:30) The Traits Bryon Looks for When Hiring (20:00) SpaceX’s Responsible Engineer Culture (25:00) Why Aerospace Became Too Risk-Averse (30:00) The Danger of Too Much Process (37:00) Nearly 100 VC Rejections to $1B (44:00) Building Hypersonic Missiles at Massive Scale