How I Invest with David Weisburd

How I Invest with David Weisburd

By David WeisburdBusiness Investing

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How I Invest with David Weisburd episodes

October 07E439: Ethan Thornton: The 22-Year-Old Building a $3.7 Billion Defense Company
What if the future of warfare is determined by who can innovate faster, not who can spend more?
Ethan Thornton is the Founder and CEO of Mach Industries, a defense technology company he started after dropping out of MIT. We break down how Mach went from experimenting with roughly 20 technologies to becoming a multibillion-dollar company, why Ethan believes asymmetric technology is reshaping modern warfare, and how Pentagon procurement is evolving. We also discuss China and Taiwan, lessons from Ukraine, autonomous warfare, recruiting exceptional talent, taking risk, and why Ethan believes great founders should empower their teams rather than make every decision themselves.
Highlights:
Why Ethan dropped out of MIT to build a defense company
How Mach experimented with roughly 20 technologies before narrowing its focus
Why building prototypes created an advantage over presenting slide decks
How Pentagon procurement is changing for defense startups
Why Ethan believes cost-plus contracting can create the wrong incentives
Why venture capital matters for asymmetric technology
How Mach recruits people around mission rather than persuasion
Why Ethan doesn’t view Anduril as a zero-sum competitor
How media fits into the strategy of a defense company
Why Ethan believes founders should find people they trust and empower them
What he misunderstood about “founder mode”
Guest Bio:
Ethan Thornton is the Founder and CEO of Mach Industries, a defense technology company focused on developing and manufacturing next-generation systems. Thornton began working on ideas for asymmetric technology as a teenager and started Mach after leaving MIT.
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 Ethan Thornton:
LinkedIn:https://www.linkedin.com/in/ethan-thornton-74417024a/
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 Ethan Thornton Dropped Out of MIT to Build Mach Industries
(2:50) How an MIT Dropout Built a Multibillion-Dollar Defense Company
(5:00) Why Mach Started by Building 20 Different Technologies
(6:41) How the Pentagon Is Changing Defense Procurement
(12:24) Could the U.S. Deter a Conflict Over Taiwan?
(25:00) How Mach Chooses Which Defense Technologies to Build
(32:47) How Mach Competes for the Best Engineering Talent
(39:03) Why Ethan Believes Staying at MIT Was the Bigger Risk
(43:55) The Leadership Lesson Ethan Wishes He Learned Earlier
(46:02) What Ethan Misunderstood About “Founder Mode”
58 min
October 05E438: Will Robbins on Elon Musk, AI & the Future of Silicon Valley
What if the biggest edge in venture capital is identifying an exceptional founder before everyone else does?
Will Robbins is a technology-focused venture investor and founder of Robbins Capital, where he backs companies starting at formation. Previously, Will joined Contrary as its first employee and helped grow the firm to more than $250 million in AUM. In this episode, Will explains why traditional VC brands may matter less in an AI-driven world, how he identifies exceptional founders before they have traction, why the best startups often pivot, and why reputation with founders may be the most important asset a venture investor can build.
Highlights:
Why traditional VC brands may be losing their edge
How AI could fundamentally change the economics of seed rounds
Why founders may need dramatically less capital to reach product-market fit
How two 17-year-old founders built Zepto into a massive retailer
Why college dropouts can produce disproportionately large venture outcomes
The elusive “X factor” Will looks for in exceptional founders
Why a founder’s social graph can reveal signals a pitch meeting cannot
Why extreme focus may be one of the most important founder traits
The small group of business models behind many of venture’s biggest outcomes
Why Will remains optimistic about software despite AI disruption
Why 50% of Will’s successful early-stage investments pivoted
The one asset Will believes matters most for a long-term venture career
Guest Bio:
Will Robbins is a technology-focused venture investor and founder of Robbins Capital, where he backs companies starting at company formation. Prior to investing under his own name, Will joined Contrary as its first employee and helped grow the firm from the ground up to more than $250 million in AUM. Early-stage companies Will was responsible for backing now have a combined market capitalization of over $10 billion.
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 Will Robbins:
LinkedIn:https://www.linkedin.com/in/whrobbins/
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 VC Brands May No Longer Matter
(5:05) What Happens to Seed Rounds When Software Gets Cheap?
(10:40) How Two 17-Year-Olds Built Zepto
(16:00) Why College Dropout Founders Keep Producing Outliers
(21:53) What Will Looks for in Exceptional Founders
(23:52) Can You Actually Identify the Founder “X Factor”?
(29:20) The Founder Signal That’s Almost Impossible to Fake
(41:11) Which Business Models Create Venture’s Biggest Outcomes?
(54:41) Why So Many Great Startups Pivot
1 hr 17 min
October 02E437: Doug Beyer on Raising Capital, LP Psychology & GP Stakes
What if the biggest opportunity in private markets isn’t backing companies—but backing the next generation of investment firms?
In this episode, I sit down with Douglas Beyer, managing partner and founder of Roaring Brook Holdings, to discuss why emerging managers remain one of the most undercapitalized opportunities in alternative assets. Douglas explains how anchor capital changes fundraising dynamics, why LP relationships determine whether firms survive, and how the best emerging managers build trust through transparency and execution. We also explore GP seeding, organizational durability, and why fundraising momentum matters more than most managers realize.
Highlights:
Why emerging managers face a structural capital gap
How anchor investors solve the “cold start” problem
Why LP relationships are built years before capital is deployed
The hidden importance of communication and transparency
How fundraising momentum determines fund survival
Why many great investors fail at building firms
The difference between raising capital and building a franchise
How secondary markets are reshaping private equity liquidity
Guest Bio:
Douglas Beyer is managing partner and founder of Roaring Brook Holdings, a firm providing seed, acceleration, and GP solutions to the next generation of private market investment firms. He spends his days evaluating opportunities where their capital, relationships, and strategic involvement can catalyze and improve the success of a firm.
Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with Douglas Beyer:
LinkedIn:https://www.linkedin.com/in/douglas-beyer-2944bb1a/
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 Left a Prestigious Family Office to Back Emerging GPs
(2:00) The Hidden Value Most Investors Miss in Asset Management Firms
(5:27) Why LP Relationships Matter More Than Most GPs Realize
(9:10) The Gold Standard for Managing LP Communication
(14:08) The Anchor Investor Problem Breaking Emerging Managers
(17:23) The Silent Risk LPs Fear Most in New Funds
(22:26) Why the Best GPs Add Value Before Asking for Capital
(29:26) Why Emerging Managers Still Matter in a Mega-Fund World
(34:17) The One Thing Every New Fund Needs to Survive
42 min
September 30E436: Nnamdi Okike on Billionaires, Founder Psychology & the Venture Capital Bubble
Can venture capital really be turned from instinct into science?
Nnamdi Okike is Co-Founder and Managing Partner of 645 Ventures, where he leads Seed and Series A investments in software and software-enabled companies. We discuss why Nnamdi believes venture investing is driven by the totality of an investor’s experiences rather than pure instinct, how 645 quantifies founder qualities, and why missionary and “non-central casting” founders can become exceptional investments. We also explore why startups need the right market inflections, how stablecoins and agentic commerce are reshaping fintech, what Nnamdi has learned across five fund vintages, and why raising too much capital at Seed can actually hurt a company.
Highlights:
Why venture investing may be more science than instinct
How 645 Ventures quantifies founder potential
Why Nnamdi prefers missionaries over mercenaries
What separates “non-central casting” founders
Why great founders still need the right market inflection
Why VCs can mistake themselves for the customer
How to tell whether founder confidence is actually justified
Why stablecoins could transform global financial infrastructure
How AI and programmable money could enable agentic commerce
Why market cycles should influence venture deployment
Why patience and truth-seeking are core values at 645 Ventures
Why massive Seed rounds can damage startup culture
Guest Bio:
Nnamdi Okike is Co-Founder and Managing Partner of 645 Ventures, where he partners with founders building vertical and horizontal software and software-enabled companies. 645 Ventures leads Seed and Series A rounds and works closely with exceptional teams as they scale toward the growth stage.
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 Nnamdi Okike:
LinkedIn:https://www.linkedin.com/in/nnamdiokike/
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 Investing Isn’t About Instinct
(3:36) How 645 Quantifies Founder Potential
(5:41) Why the Best Founders Think Differently
(9:14) What Really Predicts an Exceptional Founder
(13:29) The Inflection Points Behind Great Startups
(17:35) The Hidden Failure Mode in Early-Stage Investing
(23:51) Why Harder Markets Require Different Founders
(31:53) Where Fintech’s Next Opportunities Are Emerging
(44:38) The Biggest Lessons From Four Venture Funds
(57:03) Why Too Much Seed Capital Can Hurt Startups
1 hr 8 min
September 28E435: Why Most Companies Aren’t Ready for AI
Which competitive moats will actually survive the AI era?
SC Moatti is Managing Partner at Mighty Capital and Board Chair at Products That Count. We break down what Mighty Capital learned from mapping 550 companies by defensibility, why traditional SaaS advantages like switching costs and data moats may be weakening, and why network effects and counter-positioning are emerging as powerful AI-era moats. We also discuss why SC disagrees with the conventional power-law approach to venture, how AI is transforming M&A and corporate innovation, the Product Alpha Effect behind Mighty Capital’s investment strategy, and what venture firms must change to survive the AI transition.
Highlights:
What Mighty Capital learned from analyzing 550 companies
Why traditional SaaS moats may no longer work in AI
Why network effects and counter-positioning are gaining importance
Why the IPO threshold may now be closer to $30–50 billion
Why SC disagrees with the conventional power-law approach to venture
How AI is shifting M&A from financial engineering to product innovation
Why the best companies treat leaders like resource allocators
How the Product Alpha Effect turns product innovation into investment alpha
How Mighty Capital uses signals from 600,000 product builders
The two metrics SC believes investors should watch in AI companies
Why AI could force companies to reinvent distribution
Which venture capital firms could survive the AI transition
Guest Bio:
SC Moatti is Managing Partner at Mighty Capital and Board Chair at Products That Count. She co-founded Mighty Capital around the Product Alpha Effect, a data-backed framework for investment outperformance, and has invested in companies including Amplitude, Netskope, and Groq. Earlier in her career, SC built products at Meta and Siebel Systems and authored an award-winning book on what makes a great product. She is a Stanford GSB alum, Kauffman Fellow, YPO member, and graduate of CentraleSupélec.
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 SC Moatti:
LinkedIn:https://www.linkedin.com/in/scmoatti/
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) Which Moats Actually Survive AI?
(1:37) How SC Stays Disciplined on Valuation
(4:55) Why Power-Law Investing Can Become a Constraint
(6:32) How AI Is Rewriting the M&A Playbook
(14:11) The Product Alpha Effect Behind Mighty Capital
(17:47) The Two AI Metrics Investors Should Watch
(21:43) Why AI Could Reinvent Distribution
(24:11) What Makes a Great Product in the AI Era?
(30:30) Which Venture Firms Will Survive AI?
(36:20) The Advice SC Would Give Her Younger Self
44 min
September 25E434: Warren Gibbon on How AI is Changing the Private Markets
Are private markets still positioned to outperform public markets?
Warren Gibbon is a Multi-Family Office Chief Investment Officer with deep experience across asset allocation, equity research, and portfolio management. We discuss why investors may need to re-underwrite their assumptions about private markets, how higher rates and growing competition have changed private equity, and why public-market earnings growth may be underappreciated. Warren also explains why he is more constructive on venture, what he looks for in emerging managers, the risks created by passive investing, and how he would deploy $100 million of fresh capital today.
Highlights:
Why investors should re-underwrite the case for private markets.
What the endowment model’s historical returns may be hiding.
Why Warren believes public-market value creation is underestimated.
The risk behind today’s massive AI infrastructure spending boom.
Why private equity faces a much harder environment going forward.
How passive investing may be changing the behavior of public markets.
Why “boring and hard” investments can remain structurally underfunded.
How Warren would deploy $100 million of fresh liquidity today.
Guest Bio:
Warren Gibbon is a Multi-Family Office Chief Investment Officer with 14 years of investment management experience and a focus on U.S. and global equities. His expertise spans asset allocation, equity research, portfolio management, investment analysis, and valuation, with additional interests in behavioral finance and the construction of diversified portfolios across public and private markets.
Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit junipersquare.com/howiinvest.
AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Warren Gibbon:
LinkedIn:https://www.linkedin.com/in/warren-gibbon-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) Will Private Markets Still Outperform?
(4:00) Is the AI Spending Boom Sustainable?
(7:00) Why Warren Is Cautious on Private Equity
(13:00) Why Venture May Be More Attractive Today
(18:00) Why “Boring and Hard” Can Be a Great Investment
(21:00) Is Passive Investing Breaking the Market?
(27:00) Why Liquidity Could Become Your Biggest Advantage
(31:00) The Problem With Portable Alpha
(34:00) How Warren Thinks About Venture’s Top Firms
(40:00) How He Would Invest $100 Million Today
1 hr 1 min
September 23E433: AlphaSense’s Chris Ackerson on AI, the Future of Finance & Finding Alpha
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
37 min
September 21E432: $24 Billion Investor on Private Credit, the Psychology of Winning & Fear of Failure
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
48 min
September 18E431: Marty Kausas on AI, Trillion Dollar Startups & Founder Psychology
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
1 hr 15 min
September 16E430: Goldman Sachs’ Michael Bruun on AI, Private Equity & The War for Talent
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
38 min

About How I Invest with David Weisburd

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How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS,…

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