How I Invest with David Weisburd

Latest Episodes:

E193: GLP-1s, AI & the End of Sick Care: The Next $10B Health Tech Giant Jul 30, 2025

Show notes

What if your healthcare wasn't about just treating sickness, but maximizing your potential? In today's episode on How I Invest, I spoke with Dr. Cameron Sepah, founder and CEO of Maximus, a performance medicine company pioneering a new paradigm in healthcare. Cameron previously helped build Omada Health, now a billion-dollar public company, and coined the term “digital therapeutics.” Now he's productized his unique medical expertise into a next-gen men's health platform. We talked about the evolution of performance medicine, why testosterone and GLP-1s are changing how Americans manage their health, and how AI is reshaping clinical decision-making. We also dug deep into the personal and systemic failures of the traditional healthcare model — and what the next 10 years will look like as proactive medicine goes mainstream.

Highlights:

Why traditional healthcare is really a “sick care” system
What “performance medicine” is — and why it matters
How Maximus prescribes testosterone and GLP-1s for optimization, not just treatment
What Cameron learned as founding team at Omada Health
Why Maximus runs clinical trials when most telehealth companies don’t
The case for microdosing semaglutide (Ozempic) and GLP-1s
What most men are missing in their bloodwork — and how to fix it
The biggest misconceptions around testosterone therapy
How AI will revolutionize diagnostics, dosing, and coaching
Why Maximus could only have been built by a psychologist

-- Guest Bio: Dr. Cameron Sepah is the founder and CEO of Maximus, a consumer healthcare technology startup pioneering performance medicine. Before Maximus, he was on the founding team at Omada Health, where he served as Medical Director and coined the term “digital therapeutics.” He is a licensed clinical psychologist, former psychiatry professor at UCSF, and has advised numerous CEOs and venture capital firms on performance and mental optimization.

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

#VentureCapital #VC #Startups #OpenLP #assetmanagement

-- Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Cameron Sepah: https://www.linkedin.com/in/drsepah/

Links: Maximus: https://www.maximustribe.com/

-- Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (1:32) Lessons from Omada and Publishing Research (5:06) Clinical Trials and GLP-1 Microdosing Strategies (10:07) Insurance Challenges and Personalized Dosing of GLP-1s (14:16) The Future of GLP-1s and Obesity Treatment in America (18:31) Psychological Influences on Obesity and Dietary Choices (21:02) Comprehensive Research on GLP-1s and Weight Management (26:37) Medication Perceptions and Performance Enhancement Debate (30:36) The Role of AI in Advancing Healthcare (35:49) Key Diagnostic Tests for Men's Health Optimization (39:28) The Significance of Routine Blood Testing (41:22) At-Home Blood Testing Innovations (42:35) Turning Personal Expertise into a Scalable Business (43:32) Closing remarks

E192: Lessons from a Top Pension Turnaround w/Anurag Chandra Jul 28, 2025

Show notes

In this episode, I spoke with Anurag Chandra, Chief Investment Officer of a single-family office and longtime trustee and former Investment Committee Chair of the San Jose Federated City Employees’ Retirement System (FSERS). Over the past decade, Anurag has helped transform FSERS from one of the worst-performing pension plans in the U.S. into a top-decile performer. He’s also an experienced operator, venture capitalist, and accidental allocator—with hard-won insight into everything from re-risking public portfolios to model delivery and tax-loss harvesting. In our conversation, Anurag shared how EQ, team dynamics, and governance structure often outperform raw IQ in investing—and how he helped rebuild a $2.2B pension plan through careful governance reform, luck, and great timing. We also covered how he now applies those same principles at a nimble family office, blending institutional rigor with operational agility.

Highlights:

Why Anurag believes a 120 IQ and a great network beats a 160 IQ and no network
The governance overhaul that led San Jose FSERS from bottom-2 to top-decile performance
Lessons from studying Canadian pension best practices
How his CIO made a bold move during the March 2020 crash—and why it paid off
Why he thinks more family offices should behave like institutions
A breakdown of model delivery, tax-loss harvesting, and custom indexing
How his operator/investor/allocator background informs his investing philosophy
Thoughts on emotional intelligence in finance—and why it’s more than a “soft skill”

-- Guest Bio: Anurag Chandra is currently the Chief Investment Officer of a single-family office based in the Bay Area. He previously served for nearly a decade on the board of the San Jose Federated City Employees’ Retirement System, including several years as Chair of the Investment Committee. Under his leadership, the pension plan went from being one of the lowest-performing in the country to a consistent top-decile performer. Anurag has also worked as a venture capitalist, operator, and advisor, with 25+ years of professional experience across legal, investment, and entrepreneurial roles.

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: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Anurag Chandra: https://www.linkedin.com/in/anchandra/

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

(0:00) Episode preview (1:11) The Value of EQ and Resourcefulness in Business (11:40) Anurag Chandra's Career and San Jose Pension Fund Turnaround (19:14) Governance and Manager Selection Challenges in Pension Funds (23:45) Applying Pension Fund Lessons to Family Office Management (26:52) Strategies in Tax Optimization and Asset Allocation (30:05) Model Delivery Concerns in Asset Management (30:58) Integrating Skills for Better Investment Decisions (34:41) Cross-functional Experience and First Principles Thinking (35:05) The Role of a Board Member and Opinion Strength (37:02) Closing remarks

E191: Randal Quarles: From Fed Vice Chair to Private Equity Trailblazer Jul 25, 2025

Show notes

Randal Quarles has been at the helm of some of the most influential institutions in finance and government. From his tenure as Vice Chair of the Federal Reserve and Under Secretary of the Treasury, to his leadership role at The Carlyle Group, Randal brings a rare blend of private market acumen and public sector insight. Today, he's the Chairman and Co-Founder of The Cynosure Group—an investment firm anchored by the Eccles family and built to solve the very structural misalignments that plague private equity for families and foundations. In this conversation, we explore the evolution of private equity, the mismatch between GP incentives and family office needs, the importance of long-duration compounding, and how Cynosure is creating a modern investment firm inspired by the early days of Lazard and Rothschild.

Highlights:

Why traditional private equity isn’t always aligned with family offices—and how Cynosure is solving that
The challenges of long-hold investing and how cash-flowing businesses unlock structural advantages
How Cynosure is organized: six subsidiaries across PE, credit, OCIO, ultra-high-net-worth advisory, hedge funds, and sports investing
Why Randal prefers growth equity in “unloved” sectors like HVAC and sanitation—rather than chasing tech
Lessons from working with David Rubenstein at Carlyle and deploying capital through the Great Financial Crisis
The philosophy behind building an enduring investment firm—and the one piece of advice he’d give his younger self

-- Guest Bio: Randal Quarles is the Chairman and Co-Founder of The Cynosure Group, a Salt Lake City–based investment firm anchored by the Eccles family. He brings over 40 years of experience across financial services, public service, and private equity. Prior to founding Cynosure, he served as Vice Chair for Supervision at the U.S. Federal Reserve, U.S. Executive Director at the IMF, and Under Secretary of the Treasury. In the private sector, he was a longtime partner at The Carlyle Group, where he led its financial services fund.

Randal’s specialties include financial services investing and financial services policy. At Cynosure, he’s built a modern investment firm modeled after the early days of Lazard and Rothschild—designed to meet the structural and tax challenges faced by families, endowments, and long-term investors.

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: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Randal Quarles: https://www.linkedin.com/in/randal-quarles-4b09788/

Links The Cynosure Group: https://cynosuregroup.com/

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

(0:00) Episode preview (0:06) Private equity funds vs family offices and tax implications (2:10) Evergreen structures, pension funds, and Cynosure Group overview (7:12) Transition to private investments and recruiting challenges (11:07) Cynosure's business structure and growth equity strategies (19:53) Asset class supply and demand dynamics (24:43) Asset allocation framework and sports investing strategies (26:16) Philosophical approaches to team building and recruitment (28:25) Initial impressions of Carlyle's leadership (32:48) Carlyle's Model T approach in private equity (36:02) Deploying a financial services fund during the Great Recession (38:13) Transitioning from law to investing and government influence (41:37) Career advice and investment principles (49:38) Encouraging career flexibility and understanding risk (51:00) Lessons on self-belief and meeting aspirational peers (51:38) The Eccles family's impact on Utah Jazz (52:46) Closing remarks

E190: $600 Billion Parametric CIO: Thomas Lee on Markets, Debt & Trust Jul 23, 2025

Show notes

In this episode of How I Invest, I spoke with Thomas Lee, Co-President and CIO of Parametric, a $600 billion asset manager within Morgan Stanley Investment Management. Tom walks us through how Parametric helps high-net-worth individuals access institutional-quality investment strategies, why customization is the future of asset management, and how their technology powers nearly a quarter million highly personalized accounts. We talk about inflation myths, the credibility of the Fed, and whether the U.S. will eventually inflate its way out of debt. Tom also shares how Parametric brings tax-efficient investing and direct indexing to portfolios as small as $25,000, explains why "investments as a service" is not just a tagline, and offers valuable insights on long-term leadership, scale, and innovation. Whether you're an institutional allocator, wealth manager, or an individual trying to understand the future of investing, this episode is packed with takeaways.

Highlights:

Parametric manages $600B AUM, accounting for ~37% of Morgan Stanley Investment Management
Inflation discussion: CPI vs PCE, and why inflation "feels" higher than reported
The myth of hidden inflation and how CPI is calculated
Explanation of the Five-Year, Five-Year Forward Rate as a proxy for Fed credibility
Why Parametric doesn’t try to predict markets—and what they focus on instead
Delivering customized SMAs down to $25K accounts
Use cases for tax-loss harvesting, completion portfolios, and values-based overlays
The evolution of pooled funds to the current era of hyper-customized investing
Behind-the-scenes on how Parametric runs technology at scale
Thoughts on active vs passive investing and market efficiency
The challenge of integrating private alternatives into public portfolios
Tom’s leadership philosophy: resource allocation, storytelling, and resilient growth

-- Guest Bio: Thomas Lee, CFA is Co‑President and Chief Investment Officer at Parametric, part of Morgan Stanley Investment Management. He joined Parametric in 1994, brings over 30 years of experience, and previously spent two years at the Board of Governors of the Federal Reserve.

As Co‑President & CIO, Tom leads investment teams responsible for research, strategy, portfolio management, and trading, and serves as a voting member on all investment committees. He holds a BS in Economics and MBA in Finance from the University of Minnesota, is a CFA charterholder, and actively engages with the CFA Society of Minnesota.

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: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Thomas Lee: https://www.linkedin.com/in/thomas-lee-97a8826/

Links Parametric: https://www.parametricportfolio.com/

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

(0:00) Episode preview (1:06) Understanding Inflation: CPI and PCE Differences (3:25) Personal and Conspiracy Views on Inflation (6:21) Inflation Coordination and the Five Year Forward Rate (11:39) Tools for High Net Worth Clients in Institutional Finance (14:52) The Rise of Direct Indexing and Its Tax Advantages (17:09) The Shift to Hyper Customization in Finance (23:33) Managing Complexity in Fractional Shares and SMAs (24:51) Customization Strategies for Enhancing Returns (26:25) Debating the Efficient Market Hypothesis (28:16) The Integral Role of a Chief Investment Officer (CIO) (30:38) Communication Challenges within Large Organizations (34:34) Balancing Customer Feedback with Internal Innovation (36:03) Analyzing the Growth of Alternative Investments (41:39) Market Dynamics: Private vs. Public Asset Convergence (42:21) The Relevance of Active Investing in Efficient Markets (44:12) Investment Wisdom: Advice to a Younger Self (47:59) Investment Decision-Making and Contrarian Thinking (51:04) Parametric's Investment Philosophy and Future Plans (52:22) Closing remarks

E189: Inside the Goldman Sachs Prop Desk: Lessons from a Top Trader w/Nancy Davis Jul 21, 2025

Show notes

Nancy Davis spent nearly a decade on Goldman Sachs’ legendary prop desk before founding Quadratic Capital, the firm behind the popular iVol ETF. In this episode, we dive deep into her options-based approach to investing, why she believes most investors manage risk backward, and how her firm is positioning for a potential return of stagflation. We also talk about her early days at Goldman, the psychological traps investors fall into, and why she thinks humility and coachability are underrated superpowers in finance. If you’ve ever wanted to understand volatility, inflation protection, or how to think like a derivatives trader—this episode is for you.

Highlights:

Starting her career on Goldman Sachs’ Risk Arbitrage desk in the 1990s
Managing Goldman’s capital like a hedge fund—without client exposure
Why she avoids stop losses and manages risk upfront using options
“Debit card investing”: sizing positions by max loss instead of leverage
Turning the traditional core-periphery portfolio model on its head
How Quadratic makes options the core strategy, not a hedge
Lessons from trading during the 2020 oil price shock and SVB crisis
How the market is not pricing in inflation anymore—and why that matters
The risks of a stagflationary regime and how iVol is built to respond
What it really means to be coachable and the power of feedback
Her most contrarian take on the market going into 2025

-- Guest Bio: Nancy Davis is the founder and managing partner of Quadratic Capital Management and the portfolio manager for the firm’s investment strategies, including the Quadratic Interest Rate Volatility and Inflation Hedge ETF (ticker: $IVOL). Before founding Quadratic in 2013, she spent nearly 10 years at Goldman Sachs, where she was a key member of the proprietary trading desk. Nancy has been recognized by Barron’s and other financial media as one of the leading experts on interest rate volatility, inflation hedging, and options-based portfolio strategies.

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: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Nancy Davis: https://www.linkedin.com/in/nancyquadratic/

Links Quadratic Capital Management: https://www.ivoletf.com/

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

(0:00) Episode Preview (0:59) Differences in trading for internal partners vs. end clients (1:56) Anti stop-loss philosophy and risk management (4:24) Psychological aspects and significant trades in investing (8:41) Discussion on market inflation and lessons from Goldman Sachs (12:58) Importance of mentorship in finance (19:01) Contrarian market perspectives and stagflation explained (20:57) Closing remarks

E188: The CAZ Way: Alignment, Access & Asymmetric Upside Jul 18, 2025

Show notes

Mark Wade leads strategy and investments at CAZ Investments, a Houston-based firm managing approximately $10 billion in assets. In this episode, we unpack the evolution of the alternatives landscape, the rise of evergreen funds, and what it means to lead with alignment—starting with $700 million of insider capital invested alongside clients. Mark gives a candid look at how CAZ sources differentiated deals, manages risk through the “CAZ Case” downside model, and builds trust by investing alongside 7,000+ LPs. We also dig into how the firm leverages NAV-based leverage, the growing appetite for alternatives from RIAs, and why humility is essential when allocating capital. If you're an allocator, an advisor, or simply trying to understand where private markets are headed, this episode is packed with insights from one of the most thoughtful voices in the space.

Highlights:

The origins of CAZ Investments and how it scaled to $10B AUM
Why Mark believes the RIA channel is the future of wealth advisory
How CAZ gains access to top-tier deals—and why being the “first call” matters
Explaining the CAZ Case: their rigorous downside underwriting model
Why advisors must lead with conviction to retain and win clients
The mechanics and benefits of NAV-based leverage
Evergreen vs. drawdown funds—when and why each structure matters
How alignment of interests drives investment outcomes
Why top decile managers operate under an entirely different paradigm
The future of consolidation in private markets and what it means for allocators
Mark’s view on Tony Robbins becoming a strategic partner and investor in CAZ
The surprising edge of having 7,000 investors in all 50 states and 36 countries

-- Guest Bio: Mark Wade is a Partner at CAZ Investments, where he leads investment strategy and firm initiatives. Since joining CAZ in 2013, Mark has helped the firm expand its presence across asset classes, with a particular focus on GP stakes, energy, and professional sports. Prior to CAZ, Mark earned his MBA from the Rice University’s Jones Graduate School of Business. CAZ is known for its alignment-first model—deploying more than $700 million of insider capital alongside its LPs across a range of alternative investments.

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: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Mark Wade: https://www.linkedin.com/in/mark-wade-caia-334b951b/

Links CAZ Investments: https://cazinvestments.com/

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

(0:00) Episode preview (2:09) The growing demand for alternatives in the high net worth space (5:14) Comparing independent advisers and wirehouses (8:21) The rise of alternative investments and regulatory impacts (12:01) CAZ's investment strategy and leveraging funds (19:14) Drawdown vs. evergreen fund structures and management (26:27) Evergreen fund valuation and GP-LP interest alignment (33:53) Encouraging junior team investments and diversified LP advantages (38:47) Building partnerships and obtaining honest references (44:04) Maintaining investment strategy vigor and flexibility (47:00) Trust-building and strategic partnership importance (50:33) Co-investment tactics and humility in due diligence (56:02) CAZ case study on downside protection (59:22) Emphasizing downside protection for sustained success (1:01:01) Navigating game selection in investment strategies (1:03:57) Predicting future trends in private asset markets (1:07:59) Strategic impact of relationship with Tony Robbins (1:10:48) Key lessons from early career experiences (1:13:00) Philanthropy's role in personal and professional success (1:16:29) Building meaningful, long-term relationships (1:19:19) Final thoughts on long-term thinking in market selection (1:19:44) Closing remarks

E187: Why Holding Companies Beat Private Equity w/Matt Foran Jul 16, 2025

Show notes

What if Berkshire Hathaway were built today, with the best of technology and long-term thinking baked into its DNA? That’s the question Matt Foran and his team at StoicLane are answering—by doing it. In this episode, I speak with Matt Foran, co-founder of StoicLane, a holding company quietly building one of the most interesting portfolios in private markets. With over 70 acquisitions across four major verticals—accounting, PEO, appraisal and mortgage services, and vacation rentals—StoicLane now manages $300M in TTM revenue and expects $60M in EBITDA this year. But it’s not just the numbers. StoicLane stands out for its permanent capital structure, seller-friendly integration approach, and deep use of technology and AI to transform old-school industries. We dive deep into how Matt thinks about company building, permanent capital advantages, competing with PE firms, and the cultural flywheels StoicLane is creating as they scale.

Highlights:

The long-term edge of a permanent holding company
Why legacy preservation wins deals in fragmented industries
How StoicLane acquired 71 companies in 3.5 years
Building the 2nd largest vacation rental platform in the U.S.
The C-Corp + LLC structure and what it enables
Aligning every employee with equity ownership
Using AI to uplevel employees and improve service quality
Why top talent is the only real constraint
The tax advantages of evergreen structures
Lessons from competing with PE playbooks—at a different pace

-- Guest Bio: Matt Foran is the Co-Founder, President, COO, Board Member of StoicLane, a holding company focused on acquiring and transforming real estate and small business service firms using technology and permanent capital. Since launching StoicLane, Matt and his team have completed 71 acquisitions across four major verticals, scaling the platform to $300M in trailing revenue and $60M in EBITDA. Prior to founding StoicLane, Matt built and exited multiple startups in FinTech, real estate, and InsureTech.

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: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Matt Foran: https://www.linkedin.com/in/mattforan/

Links StoicLane: https://www.stoiclane.com/

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

(0:00) Episode preview (0:31) Business scale, acquisitions, and holding company benefits (2:30) Long-term vision in vacation rental business (4:32) Stoic team background and competitive advantages (8:06) Financial outcomes with a unique investment approach (10:27) Business strategies in different verticals (11:26) Proprietary deal flow and acquisition strategy (15:02) Holding company incentives and reverse references (19:33) Commitment fulfillment and long-term relationship building (22:25) Tax benefits of Stoic's business structure (24:18) Capital redeployment and value compounding (26:26) Advantages of evergreen structures (29:14) Utilizing AI in business roll-ups (34:48) Limited use of holding companies in the industry (38:04) Seeking talent for Stoic's growth (40:34) The value of self-sufficiency in employees (42:11) Closing remarks

E186: Where’s the Alpha Opportunity in VC in 2025? w/Abe Finkelstein Jul 14, 2025

Show notes

What’s the playbook for building a resilient, multi-billion‑dollar venture firm that weathers every market cycle? In this episode, Abe Finkelstein, Co‑Managing Partner at Vintage Investment Partners, shares how they underwrite managers, navigate funds‑of‑funds and secondaries, and spot next‑gen innovation—all while maintaining LP confidence across turbulent times.

Highlights:

How Abe began his career in equity research and transitioned into institutional analysis
The origin story of Vintage Investment Partners and how it grew to manage over $3B
Why Vintage operates across fund-of-funds, secondaries, and direct growth investing
How he evaluates managers and pricing across public and private markets
What it takes to build long-term trust with LPs in an increasingly competitive market
Abe’s thoughts on gaming, crypto, and Israel’s next big startup wave
The decision to relocate to Israel and how that shaped his worldview

-- Guest Bio: Abe Finkelstein is a Co-Managing Partner at Vintage Investment Partners, a global venture platform investing in fund-of-funds, secondary, and direct growth-stage opportunities. Vintage manages over $3 billion across its strategies and partners with leading venture firms and startups globally.

Before joining Vintage, Abe was a Senior Equity Analyst at Goldman Sachs, where he covered Israeli technology companies. He began his career at Brown Brothers Harriman and later served as Vice President at U.S. Bancorp Piper Jaffray. Abe holds a B.S. in Economics from the Wharton School at the University of Pennsylvania, where he graduated magna cum laude.

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: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Abe Finkelstein: https://www.linkedin.com/in/abe-finkelstein/

Links: Vintage Investment: https://vintage-ip.com/portfolio/

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

(0:00) Episode preview (4:03) AI, regulation, and its impact on European venture (7:38) Vintage's investment strategy and focus on emerging managers (12:42) De-risking and advantages of investing in fund ones (23:49) Adapting investment strategies and annual evolution (25:20) Annual off-sites: Key topics and implementing lessons (30:31) Consistency in team across investment strategies (33:06) Generational transfer and firm resilience (37:30) Israel's investment ecosystem and potential peace premium (42:34) Impact of peace on Israeli entrepreneurs and market dynamics (44:43) Advice for aspiring venture capitalists (47:29) Celebrating venture wins and managing the professional-personal balance (48:06) Reflecting on past deals and closing thoughts (48:51) Closing remarks

E185: Why Institutional Investors Invest into C-Class Real Estate w/Amy Rubinstein Jul 11, 2025

Show notes

I spoke with Amy Rubenstein, CEO of Clear Investment Group, about how she built a thriving real estate platform by focusing on one of the most overlooked areas of the market: distressed C-class multifamily housing. Amy didn’t come from institutional real estate — she taught herself everything from Excel to underwriting by reverse-engineering models, and built a company that now serves both high-net-worth and institutional LPs. Today, her firm consistently delivers 30%+ IRRs by stabilizing mismanaged assets and restoring them to market performance. We talk about her journey from buying a single six-unit property to leading a vertically integrated investment platform, her thoughts on risk and inflation, why C-class housing remains resilient, and how she thinks about scaling her team and her impact.

Highlights:

Why Amy believes C-class multifamily is the most resilient and alpha-rich real estate strategy
How Clear Investment Group creates value by stabilizing mismanaged assets
The learning curve of becoming a solo GP with no institutional background
Amy’s approach to managing and growing a high-performing team
Her philosophy on impact investing — and why they never needed to label it as ESG
Institutional fundraising: the 18-month grind and what comes after the first big check
How her firm stress-tests for interest rate shocks and avoids market speculation
The strategic vision for a one-stop-shop multifamily investment platform

-- Guest Bio: Amy Rubenstein is the CEO and co-founder of Clear Investment Group, a real estate investment firm focused on distressed, workforce multifamily housing across the U.S. Under her leadership, Clear has grown from small syndicated deals to managing institutional capital and generating 37%+ average IRRs. She has over two decades of experience in real estate investing, is a self-taught operator, and remains deeply involved in every aspect of the firm’s strategy and execution.

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: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Amy Rubenstein: https://www.linkedin.com/in/amy-rubenstein-a0514698/

Links Clear Investment Group: https://www.linkedin.com/company/clear-investment-group/posts/?feedView=all

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

(0:00) Episode preview (1:24) Management and tenant issues in distressed properties (3:02) Amy Rubenstein's industry beginnings and real estate asset performance (5:26) Forecasting interest rates and market conditions (7:59) Interactions with LP base and institutional investors (11:11) Institutional interest and tax benefits in C class real estate (14:07) Essentials of being a successful GP (17:09) Team management and the role of humility (21:22) Delegation, high achievers, and trust (24:19) Growth strategy and future business outlook (26:07) Multifamily real estate and market volatility (29:13) Investment lessons and self-taught skills (33:06) Impact investing and ESG perspectives (35:24) Closing remarks

E184: How Casper Hit $100M in Year One: The Untold Startup Playbook Jul 09, 2025

Show notes

Philip Krim is best known as the co-founder and former CEO of Casper, one of the fastest-growing direct-to-consumer (DTC) startups in history. Under his leadership, Casper hit $100M in revenue in its first year, went public in early 2020, and was later taken private. Today, Philip is building again—this time through Montauk Climate, a platform innovating in what he calls the “electron economy.” We talked about lessons from hypergrowth, managing through crisis, organizational design, and the future of climate investing.

Highlights:

How Casper hit $100M revenue in its first year
Building a brand consumers want to talk about
What it takes to lead through hypergrowth
Lessons from taking a company public right before COVID
Why he believes DTC was just the beginning of a bigger thesis
What the “electron economy” means and why it matters
Why Montauk Climate is vertically integrated across venture, credit, and incubation
How Philip evaluates early-stage founders—and what makes a good bet
Why portfolio construction is the most underrated concept in venture

-- Guest Bio: Philip Krim is the founder of Montauk Climate and the former co-founder and CEO of Casper. Under his leadership, Casper became one of the most iconic DTC brands in the world, reaching $100M in revenue in its first year and going public in 2020. After exiting Casper, Philip launched Montauk Climate, a platform focused on building and investing in the “electron economy,” with a mix of venture incubation, growth investing, and credit strategies. He is also an active early-stage investor, with early bets in Ramp, MasterClass, and Relativity Space.

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: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Philip Krim: https://www.linkedin.com/in/philip-krim/

Links: Montauk Climate: https://www.montaukclimate.com/

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

(0:00) Episode preview (11:12) Hiring for new skills and functions (16:50) Organizational design for startups (19:42) Task structuring for scalability (20:56) Adapting core beliefs while maintaining credibility (22:21) Data-driven decisions versus gut instincts (23:02) Skills needed for founding a company (26:19) Venture vs. public investors' perspectives (31:09) Introduction to Montauk Climate and its strategy (34:47) Role of credit in energy transition (37:21) Electron economy and incubated companies (50:42) Investment approach for private allocators (53:08) Exploring the electron economy (54:35) Traits of successful early-stage founders (57:16) Predicting investment success challenges (59:35) Portfolio construction in venture capital (1:00:13) Closing remarks

Our TOPPODCAST Picks

Follow Us

Stay Connected

How I Invest with David Weisburd

Related Podcasts

Links

Stay Connected