How I Invest with David Weisburd

Latest Episodes:

E283: How AI will Affect Financial Markets Jan 15, 2026

Show notes

What happens when the marginal cost of intelligence approaches zero? David Weisburd speaks with Richard Socher about building U.com, the evolution of AI search and agents, and why infrastructure—not hype—will determine AI’s real economic impact. Richard shares a first-principles view on where AI creates value, how enterprises are deploying agents today, and what long-term shifts in labor, productivity, and education may follow.

Highlights:

Building You.com and focusing AI search on accuracy and data quality
Why AI agents depend on strong search and infrastructure layers
Early enterprise use cases across coding, legal, healthcare, and research
The idea of intelligence becoming cheap and its second-order effects
Why AI adoption is gradual but structurally inevitable
Jobs, agency, and the fallacy of fixed labor supply
How AI changes access to tutoring, healthcare, and personal assistance
Investing in AI from first principles: data availability and timing
Where regulation matters and where it risks overreach
Why computer science remains foundational in an AI-driven world

Guest Bio:

Richard is the Co-Founder and Managing Director at AIX Ventures and Co-Founder and CEO of You.com, the leading AI search infrastructure for enterprises. At AIX Ventures, he has led early investments into several fast growing and category defining AI startups including Hugging Face, Weights and Biases, Athelas, Profluent, Parallel Bio, and Assured Robot Intelligence (ARI).

Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of AI startup MetaMind, acquired by Salesforce in 2016. Richard received his Ph.D. in computer science from Stanford University in 2014 and later served as an adjunct professor. He is widely recognized as having brought neural networks into the field of natural language processing, inventing the most widely used word vectors, contextual vectors, and prompt engineering. He is one of the top-five most-cited researchers in NLP, with over 230,000 citations.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Richard Socher:

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

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

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

(0:00) Introduction (1:05) AI in enterprises and its impact on job markets (4:22) Predictions for the economic impact of AI agents (7:34) AI's role in evolving local news and early enterprise use cases (8:49) AI investment strategies and Richard Socher’s fund principles (14:06) AI regulation, comparison with crypto, and geopolitical aspects (18:45) AGI, ASI, and AI's influence on math and programming (21:14) Balancing AI optimism with potential risks and existential concerns (25:01) Preparing future skills for AI-driven industries (26:15) Interdisciplinary approach combining computer science (27:09) Richard Socher's personal life insights (28:13) Closing remarks

E282: Why LPs are Investing into Independent Sponsors Jan 14, 2026

Show notes

What role do independent sponsors play in today’s lower middle market private equity ecosystem? David Weisburd speaks with Tom Duffy about how TIFF partners with independent sponsors, why deal-by-deal investing can improve alignment, and what differentiates high-quality sponsors in a rapidly growing market. Tom explains how sourcing, economics, and hands-on diligence shape long-term GP relationships and inform future fund commitments.

Highlights:

TIFF’s dual business model: OCIO services and private market strategies
Growth of the independent sponsor market and what’s driving it
Why deal-by-deal investing can improve alignment and diligence
Key attributes that define high-quality independent sponsors
How flexibility and economics attract experienced PE professionals
Fee structures and GP commitment in sponsor-led transactions
Using early deals to underwrite long-term GP partnerships
The importance of sourcing differentiation and resilience
How sponsor relationships can evolve into fund investments

Guest Bio:

Tom Duffy is a Director on TIFF’s Private Market Investment Team, where he focuses on lower middle market private equity and early stage venture capital strategies. TIFF is an outsourced chief investment officer and private markets platform managing over $10 billion* in assets, with a long-standing focus on alternatives and private markets. Tom works closely with independent sponsors and emerging managers, underwriting both deals and long-term partnerships across the lower middle market.

*TIFF assets under management (AUM) is as of 9/30/25 and includes discretionary and non-discretionary client assets for which TIFF affiliates provide investment management or advisory services. The private markets portion of TIFF AUM is calculated based upon fund net asset value plus unfunded commitments. Calculation of TIFF AUM differs from the calculation of regulatory assets under management in TIFF’s Form ADV filings with the SEC and may differ from the AUM calculation methodologies used by other investment managers.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Tom Duffy :

LinkedIn: https://www.linkedin.com/in/tom-duffy-cfa-cfp/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

(0:00) Introduction (3:03) Independent sponsor market growth and saturation concerns (7:25) Fee structures and long-term partnership benefits with TIFF (10:54) Diligencing managers and alignment of interests (15:57) Opportunities for non-pedigree sponsors and market state (21:41) Closing remarks

E281:The Tsunami of Pain Facing Venture Capital Jan 13, 2026

Show notes

Why do some venture-backed companies struggle to survive despite strong technology and teams? In this episode, David Weisburd speaks with Trey Ward about the structural differences between software and hard-tech businesses, the predictable “Death Valley” many startups face, and what recent data suggests about the future of venture funding. Trey shares how capital intensity is often misunderstood, why graduation rates are declining, and how profitability can create a path forward when fundraising stalls.

Highlights:

Why strong conviction matters most when the market disagrees
How hardware and software revenue curves fundamentally differ
The misconception around capital intensity in deep-tech businesses
What “Death Valley” looks like for hard-tech startups
How investors distinguish failed companies from those with unmet potential
Data showing declining Series A–to–Series B graduation rates
Why a post-2022 venture funding hangover is accelerating failures
Acquiring venture-backed assets at a fraction of historical R&D spend
Using profitability as a strategy to give founders more time

Guest Bio:

Trey Ward is the Founder of Rook, an investment firm focused on acquiring venture-backed technology companies that have strong fundamentals but lack access to continued venture funding. He has spent his career investing in and operating across hardware, software, and deep-tech businesses, with a focus on capital discipline, long-term value creation, and paths to profitability outside the traditional venture model.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Trey Ward:

LinkedIn:linkedin.com/in/thomasvwardiii

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

(0:00) Introduction (4:04) Challenges and differentiators for hard tech startups (7:46) Venture capital downturn and strategies for struggling assets (14:07) Investment structures and management retention in acquisitions (16:17) Closing remarks

E280: The Art of Quiet Compounding w/Mark Sotir Jan 12, 2026

Show notes

Why do the best investors spend more time preparing for what can go wrong than forecasting what might go right? In this episode, I talk with Mark Sotir, President of Equity Group Investments, about what it really means to invest with an owner’s mindset. Mark shares lessons from working alongside Sam Zell for nearly two decades, why staying alive matters more than maximizing any single outcome, and how long-term capital changes behavior inside portfolio companies. We break down why protecting downside creates asymmetry, how adaptability beats prediction, and why value creation comes from operating discipline, not transaction timing.

Highlights:

The difference between being an owner vs. a trader
Why “the hundred-year storm happens every ten years”
Preparing instead of predicting in volatile environments
Staying alive as the core compounding strategy
Why long holding periods create better outcomes than fast flips
Cash flow discipline as risk management
Why control enables transformation, not micromanagement
How flexibility inside companies prevents brittleness
Why value is created operationally, not transactionally
The danger of rigid planning in dynamic markets

Guest Bio: Mark Sotir is the President of Equity Group Investments, the private investment firm founded by Sam Zell, where he oversees the firm’s investment portfolio and works closely with portfolio companies to improve strategy and operations. He also serves as Chair of the investment committee at Chai Trust Company, the corporate trustee for the Zell family trusts. Mark joined EGI in 2006 and has held senior leadership roles across operating companies, including as CEO of Sunburst Technology and President of Budget Group, with earlier experience at Coca-Cola. He holds an MBA from Harvard Business School and a BA from Amherst College.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Mark Sotir:

LinkedIn: https://www.linkedin.com/in/mark-sotir-02577b4/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

(0:00) Introduction (0:28) Owner's mindset and risk management in private equity (1:35) Adapting investment strategies and the "hundred year storm" concept (2:22) The importance of capital structure and not over-leveraging (3:42) Navigating unpredictable market changes and staying in business (6:13) Dedicated capital base and long-term value creation (11:41) Cash flow generation and disciplined investing (12:20) Control in portfolio companies and leveraging multiple strategies (16:07) Avoiding attachment and the importance of team diversity (17:34) Balancing empathy with business decisions and founder transitions (21:01) Founder readiness and adapting to company culture (24:43) Business development, CRM strategies, and succession planning (27:40) Leadership transition, trust, and optimizing operations (29:23) Sourcing deals and the evolving landscape of private equity (30:23) Closing remarks

E279: Why Size Becomes the Enemy of Venture Returns w/Logan Allin Jan 09, 2026

Show notes

Why does venture capital break when liquidity disappears and what actually creates alpha when markets get hard? In this episode, I talk with Logan Allin, Founder and Managing Partner of Fin Capital, about why private markets are structurally changing, how secondaries are becoming a primary liquidity mechanism, and why discipline — not optimism — is what separates enduring managers from zombies. Logan explains how Fin Capital built a full-lifecycle platform across venture and late-stage secondaries, why fund size is the enemy of performance, and how contrarian positioning creates real structural alpha over time.

Highlights:

Why venture “breaks” without liquidity
How secondaries are replacing IPOs as the main exit
Why fund size destroys returns past a threshold
The rise of zombie funds and asset gatherers
How Fin Capital uses secondaries as a risk buffer
Why competition — not fundamentals — drives private market pricing
Why retail capital is dangerous for blind-pool venture funds
How contrarian investing actually works in practice
Why orchestration and application layers win in AI
Why alpha comes from doing the work others avoid

Guest Bio:

Logan Allin is the Founder and Managing Partner of Fin Capital, a global venture and growth equity firm focused exclusively on enterprise software for financial services. He previously served as Vice President at SoFi Ventures and has held operating and advisory roles across fintech and financial services, including leadership positions at Atlantic Trust, City National Bank, and several venture-backed startups. Logan holds degrees from Duke University and Stanford Graduate School of Business, where he was a Sloan Fellow.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Logan Allin:

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

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

(0:00) Introduction (1:07) Challenges and dynamics in the current venture market (2:17) Opportunities in the secondaries market and institutional capital (7:02) Diligence process for late-stage pre-IPO opportunities (9:09) Discussion on fund lifespan and size constraints (14:05) Retail investors and OpenAI's business model concerns (19:36) Howard Marks' insights and second-order thinking in investments (22:40) Investment strategies in AI and avoiding LLMs (24:02) LP communication and the cost of being a contrarian (27:08) Conversations with LPs and focus on specific tech sectors (28:32) Emerging spaces in technology investments (32:22) FinCapital's approach to investment and market relations (34:09) Closing remarks

E278: What Separates the Top 1% of GPs Jan 08, 2026

Show notes

What if the most powerful investment strategy isn’t optimization but making one truly great decision each year? In this episode, I talk with Joshua Browder, Founder and CEO of DoNotPay and a solo pre-pre-seed investor, about how momentum, conviction, and first-belief investing create outsize outcomes. Joshua shares how DoNotPay became a profitable, dividend-paying AI consumer company with a team of 14, why he focuses on backing founders before they look credentialed, and how acting decisively on binary choices can matter more than years of incremental improvement. We also explore why grit beats IQ, how momentum keeps startups alive, and what it really takes to be a founder’s first believer.

Highlights:

Why “one big decision per year” matters more than constant optimization
How DoNotPay scaled to millions of users with a tiny team
Why profitable companies can still be venture-scale
Grit vs. IQ in predicting founder success
The power of being the first believer, not the fastest follower
How momentum determines survival at pre-seed
Why binary decisions beat marginal improvements
How Joshua creates momentum for founders operationally
Why founders should build for meaning, not resumes
How portfolio construction changes at pre-pre-seed

Guest Bio:

Joshua Browder is the Founder and CEO of DoNotPay, an AI consumer rights platform that has automated over 200 legal and financial processes and won more than two million cases for users. He founded the company while studying computer science at Stanford before leaving to join the Thiel Fellowship. Joshua is also an active early-stage investor, backing first-time founders before they become obvious, and has invested in over 150 companies including Figma, Mercury, and Owner.com. His work focuses on helping people fight institutional friction while building profitable, mission-driven businesses.

Stay Connected with David Weisburd:

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

Stay Connected with Joshua Browder:

LinkedIn: https://www.linkedin.com/in/joshua-browder-b0b573116/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

(0:00) Introduction (0:39) Business model, profitability, and startup myths (2:56) Transition to venture capital and Thiel Fellowship experience (6:02) Reflecting on investment decisions and philosophy (9:47) Evaluating founders and the one-person accelerator approach (14:23) Traits of successful entrepreneurs and startups as momentum machines (18:16) Founders’ roles and commitment evaluation (23:43) Portfolio construction and key decision-making in early-stage investing (27:22) Productizing tasks and balancing tactical vs strategic thinking (30:36) Closing remarks

E277:Why the Best GPs Refuse to Raise More Capital Jan 07, 2026

Show notes

Why is the hardest discipline in growth equity not finding great companies but refusing to grow past the point where returns break? In this episode, I talk with Deepak Sindwani, Co-Founder and Managing Partner of Wavecrest Growth Partners, about why fund size discipline, culture, and integrity matter more than optics in building a great investment firm. Deepak explains why Wavecrest capped Fund III at $450M despite excess demand, how staying in the sub-$50M equity check range preserves alpha, and why being a true growth partner — not a financial engineer — creates better outcomes for founders and investors alike.

Highlights:

Why Wavecrest refused to raise a larger fund despite strong demand
The break point where growth equity becomes overly competitive
Why consistent strategy beats chasing milestones
The “treasure hunting” model for finding overlooked growth companies
Why profitable, 30–50% growth companies are the sweet spot
How direct sourcing creates better founder relationships
Why culture and “no-asshole” policies increase expected value
Selling capital to founders who don’t need it
The real reasons founders take growth capital
How adversity builds better long-term investors

Guest Bio:

Deepak Sindwani is the Co-Founder and Managing Partner of Wavecrest Growth Partners, a growth equity firm focused on profitable B2B software and technology-enabled services companies. Prior to Wavecrest, Deepak was a Partner at Bain Capital Ventures and a Principal at Comcast Ventures, where he led early- and growth-stage investments across the technology sector. He began his career in technology investment banking at Credit Suisse and later worked in product management, marketing, and business development at several technology companies, including his own startup. Deepak holds a B.S. in Electrical Engineering and Economics from the University of Pennsylvania.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Deepak Sindwani:

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

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

(0:00) Introduction (2:22) Balancing Fund Growth with Investment Strategy (3:33) Market Competitiveness and Portfolio Construction (6:12) Identifying and Investing in Growth Opportunities (9:45) The Role of Passion in Growth Equity (14:00) Building a Positive Company Culture (15:46) Challenges of Selling Capital to Self-Sufficient Companies (21:01) Wavecrest's Growth Strategies and Value Addition (25:13) Leveraging Portfolio Strengths to Win Deals (29:36) Personality Assessments in Talent Management (31:57) Deepak Sindwani's Reflections and Advice for Aspiring Investors (33:57) Bootstrapping a Fund: Strengths and Challenges (35:13) Embracing Challenges for Building Resilience (37:15) Closing remarks

E276: Lessons from Allocating $70B as CIO at the University of Texas Jan 06, 2026

Show notes

Why do the biggest investing breakthroughs come not from complexity, but from simplicity and why is that so hard for smart people to accept? In this episode, I talk with Britt Harris, one of the most experienced institutional investors in the world, about what really drives long-term investment success inside large pools of capital. Britt explains why simplicity beats complexity, how scale creates negotiating power and structural advantage, and why engagement — not intelligence — is the true separator of performance. We discuss how innovation in investing is usually recombination, not invention, why empowered teams outperform credentialed ones, and how leaders can systematically create cultures that compound.

Highlights:

Why simplicity is the highest form of reliability
How scale changes negotiating power and opportunity access
The “four-minute mile” effect in organizational change
Why fully engaged people outperform smarter but disengaged peers
The 30–50–20 rule of engagement inside organizations
Why innovation is usually recombination, not invention
How to avoid complexity syndrome in investing and management
Why keeping your word is the foundation of trust and leadership
How empowerment is earned, not granted
Why culture compounds faster than strategy

Guest Bio:

Britt Harris is a veteran institutional investor and executive who has served as Chief Investment Officer for some of the largest pools of capital in the world, including the University of Texas Investment Management Company (UTIMCO), the Texas Permanent School Fund, and the Texas Teachers Retirement System. Over a career spanning more than four decades, he has overseen and advised on portfolios totaling hundreds of billions of dollars and is widely recognized for his contributions to institutional investing, governance, and organizational leadership.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Britt Harris:

LinkedIn:https://www.linkedin.com/in/britt-harris-6678477/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

(0:00) Introduction (2:27) Overcoming impossibilities and full engagement in organizations (6:38) Empowerment and success in the workplace (12:06) Innovation in financial instruments and trends (16:12) Complexity syndrome and the importance of simplicity in investments (17:32) Closing remarks

E275: Does Grit Actually Matter in a GP — or Is It Just a Good Story? Jan 05, 2026

Show notes

Why do the people who build the most meaningful things almost always choose the hardest path and what does that unlock in the long run? In this episode, I talk with Larsen Jensen, Founding General Partner of Harpoon Ventures, about why deliberately choosing difficult problems builds the resilience, clarity, and long-term edge required to create category-defining companies. Larsen shares lessons from his time as an Olympic medalist and Navy SEAL, how those experiences shaped his investing philosophy, and why venture capital is ultimately a power-law game driven by rare outliers. We explore how founders develop mental toughness, how conviction is formed under uncertainty, and why great investors learn to trust teams more than models.

Highlights:

Why hard things produce disproportionate personal and professional growth
How resilience is built only through adversity, not theory
The role of mental conditioning in elite performance
Why venture returns come from rare exceptions, not rules
How founders choose investors more than the reverse
What it really takes to find product–market fit
Why 10x solutions and desperate customers matter most
The difference between vitamins and painkillers in startups
Why the best teams are upstream of product and market
How humility and mission matter more than ego

Guest Bio:

Larsen Jensen is the Founding General Partner of Harpoon Ventures, a venture firm focused on investing in companies that serve the national and economic interests of the United States and its allies. Before venture, Larsen was an Olympic medalist in swimming and served as a U.S. Navy SEAL, experiences that shaped his emphasis on resilience, mission, and long-term thinking. At Harpoon, he backs founders building frontier technologies across defense, cybersecurity, AI, and critical infrastructure, and is known for his founder-first, conviction-driven approach to early-stage investing.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#venturecapital #vc #startups #openlp #assetmanagement

Stay Connected with David Weisburd:

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

Stay Connected with Larsen Jensen:

LinkedIn: https://www.linkedin.com/in/larsen-jensen/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

(0:00) Introduction (0:14) Larson Jensen's background and embracing challenges (1:56) Benefits and importance of overcoming adversity (4:38) Parallels between parenting, self-coaching, and mental toughness (7:33) Resilience across multiple careers and challenging environments (10:22) Mental toughness in venture capitalism and adapting to market changes (13:41) Harpoon Ventures' investment strategy and collaboration with major funds (16:30) Mentorship, servant leadership, and characteristics of successful founders (21:43) Distinguishing high beta vs. low beta investment ideas (24:06) Defining venture capital as an access class (27:27) Startups: Achieving product-market fit and the importance of team (34:38) Building mental toughness in founders and venture capitalists (38:57) Overcoming challenges for meaningful success (42:05) Advice for aspiring fund managers and the pitfalls of rigid VC rules (44:46) Resilience in successful individuals (45:46) Closing remarks

E274:How LPs Miss Early Asymmetry by Waiting Jan 02, 2026

Show notes

What if the biggest barrier to earning returns in alternatives isn’t access, fees, or performance but friction, complexity, and behavior? In this episode, I talk with Brett Hillard, Founder and CEO of GLASFunds, about why infrastructure matters more than selection in alternative investing. Brett explains how GLASFunds helps wealth managers implement alternatives at scale, why K-1 friction keeps investors out of high-return asset classes, and how thoughtful design around vintages, liquidity, and reporting can dramatically improve long-term outcomes. We also explore why “alternatives” is an overused label, how to build portfolios across vintages, and why illiquidity can actually protect investors from themselves.

Highlights:

Why infrastructure, not product, is the bottleneck in alternatives
How GLASFunds solved the K-1 problem for multi-fund portfolios
Why most investors fail simply by not being invested at all
The behavioral value of minimizing friction and complexity
Why “alternatives” is a misleading and overused category
How to build private market exposure across vintages
Why secondaries and private credit are ideal entry points
The virtue of illiquidity and why it protects against bad behavior
Why risk is often misunderstood as discomfort
How emotional intelligence matters more than technical skill in investing

Guest Bio:

Brett Hillard is the Founder and CEO of GLASFunds, an infrastructure platform that enables wealth managers to build, customize, and implement alternative investment portfolios at scale. GLASFunds provides legal, operational, and reporting infrastructure that allows advisors to offer hedge funds and private capital strategies while dramatically reducing administrative friction, tax complexity, and behavioral barriers for investors. Brett is widely recognized for his first-principles approach to portfolio construction, risk, and behavioral finance in private markets. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Brett Hillard:

LinkedIn:www.linkedin.com/in/brett-hillard-caia-cfa-40729725/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

(0:00) Introduction (3:18) Model portfolio for high-net-worth clients and endowment strategies (9:39) Risk tolerance, liquidity, and the misinterpretation of "alternatives" (11:44) Crafting an alternatives portfolio and private credit secondaries insights (18:04) Wealth manager advantages and behavioral investing in alternatives (22:23) Selecting general partners and evaluating hedge funds (24:27) Value creation and risk-reward in private capital and fund vintages (28:32) Investing in first-time funds and assessing risk perception (32:12) Timeless investment advice and the benefits of illiquidity (35:59) Closing remarks

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