How I Invest with David Weisburd

Latest Episodes:

EP273: What the Best Family Offices Do Differently Dec 31, 2025

Show notes

What if managing your own capital and not outsourcing it is the highest-return investment decision you can make? In this episode, I talk with Alex Tonelli, Co-Founder of Endurance, about what changes when entrepreneurs manage their own money with the same first-principles thinking they use to build companies. Alex explains how Endurance evolved from a startup holding company into a highly structured family investment office, why principal-driven capital behaves differently than institutional capital, and how disciplined portfolio construction, vintage diversification, and contrarian thinking create durable long-term returns. We also explore why institutions systematically underperform their opportunity set — and how to avoid the behavioral traps that cause it.

Highlights:

Why Endurance was built as a product-market-fit response, not a plan
How founders turned company building into an investing engine
Why partners investing their own money changes every decision
Endowment-style portfolio design with entrepreneur-level risk tolerance
The “thermostat” approach to adjusting allocations
Why vintage discipline beats market timing
Why big brand funds often disappoint over time
IRR vs. MoIC and why compounding wins
The free lunch of diversification applied to illiquid assets
How information flow itself becomes a form of alpha

Guest Bio:

Alex Tonelli is a Co-Founder of Endurance, a private investment office created by a group of serial entrepreneurs to build companies and manage their own capital using first-principles thinking. Before Endurance, Alex co-founded a series of successful enterprises, most notably including Funding Circle, which became the world’s largest small-business lending marketplace and went public in 2018. As Managing Partner at Endurance, he focuses his investment work on portfolio construction, manager selection, and building scalable internal investment infrastructure designed to optimize for long-term compounding rather than institutional constraints.

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 Alex Tonelli:

LinkedIn: https://www.linkedin.com/in/n-alex-tonelli-54b2a42/

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 (0:47) Success story of Funding Circle and Collective Medical (1:19) Building the investment office and decision to start investing together (2:01) Overview of Endurance's structure and activities (2:22) Principles behind creating the family office (3:38) Problem-solving: products vs. process/people (4:44) Portfolio construction, internal processes, and decision-making dynamics (6:02) Asset allocation, investment strategy, and market timing (8:52) Valuation dynamics and contrarian views in various market conditions (10:49) Comparison of IRR vs. MOIC in investment decisions (13:15) Expected returns and comparison with institutional endowments (15:45) Principal-agent issues and behavioral factors in decision-making (17:40) Diversification strategy and targeting high-risk assets (18:35) The virtue of illiquidity and reflection on investment strategy mistakes (21:14) David Weisburd on growth and economies of scale in investment brands (26:06) Alex Tonelli on changing investment principles and proactive capital conversations (28:18) David Weisburd on LP check sizes and maximizing returns (32:15) Understanding alpha, portfolio construction, and committee-based challenges (35:05) Balancing external influence with investment integrity (37:12) Influences from legendary investors and evolving strategy (38:19) Investment philosophy contradictions and information diet (39:56) Negative alpha, impact of negative information, and curated sources (41:12) Timeless advice for new investors and biggest COVID-19 investment mistake (43:07) Closing remarks

EP272: How a $10B Company Turned De-Extinction into a Platform Dec 30, 2025

Show notes

What kind of entrepreneur decides to bring back extinct species and why might that become one of the most important businesses of our lifetime? In this episode, I talk with Ben Lamm, Co-Founder and CEO of Colossal Biosciences, about why de-extinction is not science fiction but an engineering problem — and how solving it is creating breakthrough technologies across biology, conservation, and medicine. Ben shares how Colossal evolved from a bold idea into a multi-billion-dollar platform, why mammoths, dire wolves, and dodos became cultural gateways into serious science, and how mission-driven companies can attract talent, capital, and public imagination at once.

Highlights:

Why de-extinction is an engineering challenge, not a science breakthrough
How Colossal is building a “portfolio of species” like products
Why mammoths and dire wolves are cultural on-ramps to deep tech
How Form Bio emerged from Colossal’s internal tooling
Using memes, pop culture, and celebrities to make science mainstream
Why investor alignment matters more than valuation
The difference between persuading and educating
How mission focus drives execution speed
Why frontier companies require extreme context-switching
How optionality becomes the ultimate business advantage

Guest Bio: Ben Lamm is a technology entrepreneur and the Co-Founder and CEO of Colossal Biosciences, a company focused on de-extinction, genetic rescue, and biodiversity restoration. He has previously founded and exited multiple companies across software, gaming, and AI, including Chaotic Moon (acquired by Accenture), Team Chaos (acquired by Zynga), and Conversable (acquired by LivePerson). Ben is also a Co-Founder and board member of Form Bio and is known for building ambitious, mission-driven companies that operate at the intersection of science, culture, and technology.

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 Ben Lamm:

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

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

Disclaimer:

(0:00) Introduction to de extinction, cultural significance, and company future plans (1:03) Scaling genome engineering and business models in synthetic biology (3:27) Potential applications of de extinction technologies and pharmaceutical uses (4:30) Inspiration and initial challenges in starting a de extinction company (5:22) Impact of previous successes and strategies for rapid growth (8:08) Leadership structure and the role of species leads (9:49) Lessons learned from previous ventures and aligning investors (12:34) Foundational principles and media strategy for Colossal (16:44) Worldwide awareness and balancing public narrative with business strategies (21:30) Vision for the next decade and the importance of species reintroduction (24:34) Capital market alignment and strategies for entrepreneurial resilience (27:46) Entrepreneurial mindset, dealing with failure, and the value of freedom (29:28) Episode closing and listener call-to-action

E271: The Future of VC: Space, Energy, Defense Dec 29, 2025

Show notes

How do you spot a frontier-tech company before it becomes obvious and why is being early so much harder than being right? In this episode, I talk with Jonathan Lacoste, Founder and General Partner of Space VC, about investing at the moment when ideas are still non-consensus. Jonathan explains the difference between deep tech and frontier tech, why founder migration is the strongest signal of emerging opportunity, and how pre-seed investors create alpha by backing contrarian founders before markets agree. We discuss how grit and mission outperform IQ, why concentration beats diversification in early-stage portfolios, and how patience compounds into an edge over time.

Highlights:

The difference between deep tech, frontier tech, and “just tech”
Why founder migration predicts where value is forming
Investing before consensus vs. competing after consensus
Why pre-seed alpha comes from people, not theses
How grit, obsession, and mission predict founder success
Why concentration works better than diversification at pre-seed
How Jonathan evaluates first-time founders before companies exist
Lessons from building and selling his own startup
Why hardware and industrial tech are becoming venture-scale
How patience and restraint compound into long-term advantage

Guest Bio:

Jonathan Lacoste is the Founder and General Partner of Space VC, a pre-seed venture firm backing frontier technology startups across space, defense, energy, robotics, autonomy, and physical AI. Before founding Space VC, Jonathan co-founded an enterprise software company that was later acquired by Vista, and he became one of the youngest founders to raise venture capital at age 19. He brings a founder-first approach shaped by firsthand experience building through multiple pivots, near-failures, and a successful exit. Originally from Ohio, Jonathan has spent over 15 years as a founder, investor, and advisor working with some of the most technically ambitious teams in the world.

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 Jonathan Lacoste:

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

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

Disclaimer:

(0:00) Introduction (0:42) Impact of economic conditions on startup formation and differences between deep tech and frontier tech (4:02) Transitioning from deep tech to mainstream with examples (6:12) Non-consensus investing and its importance for emerging managers (9:21) Understanding the two asset classes within venture capital (10:15) The significance of founder migration from top tech companies (12:16) Comparing thesis-led and founder-led investment approaches (18:48) The role of grit in hard tech entrepreneurship and Jebbit's challenges (24:16) Jonathan Lacoste's background and the concept of grit in startups (27:47) Mission orientation in founders and its impact on startup success (29:13) Effects of large liquidity events on founder motivation (30:29) Economic rationale for investing in frontier tech startups (32:32) Evolution of investment strategies from fund one to fund two (35:02) Communicating strategy and differentiation to LPs and aligning with them long-term (40:54) Advice on recognizing excellence and patience in capital deployment (43:48) Differences between successful entrepreneurs and VCs (45:06) Closing remarks

EP270: How Billionaires Avoid Family Chaos (and Taxes) Dec 26, 2025

Show notes

What if the most important decision in wealth planning isn’t the tax strategy—but who you trust to make decisions when you no longer can? In this episode, I talk with Thomas Monroe, Founder and President of Blue Sky Trust, about the real role of a trustee and why independence, judgment, and governance matter more than technical structuring alone. Thomas explains how trustees sit at the intersection of tax, legal, investment, and family dynamics—and why poor trustee selection can quietly undermine even the most sophisticated planning. We explore real-world trust use cases, parenting and purpose across generations, and how thoughtful structuring creates optionality without eroding values.

Highlights:

Why a trustee is a trusted advisor, not a commodity service
The trustee as the “quarterback” of complex advisory teams
Why independence is essential for both tax efficiency and judgment
Common trust use cases beyond estate tax minimization
Pre-liquidity planning and valuation discounting before exits
The control paradox: why giving up control enables better outcomes
Raising grounded, purpose-driven children with significant wealth
Avoiding “trust fund baby” outcomes through structure and intent
Why optionality matters more than optimization
How governance and accountability keep the “Ferrari” running properly

Guest Bio:

Thomas Monroe is the Founder and President of Blue Sky Trust, a Nevada-chartered independent trust company serving ultra-high-net-worth families, entrepreneurs, and multigenerational family offices. With more than 25 years of experience, Thomas advises families and their advisory teams on sophisticated trust, estate, tax, and philanthropic planning, with a focus on governance, execution, and long-term alignment. He is widely recognized for bridging technical rigor with practical decision-making and for helping families navigate complexity while preserving flexibility, purpose, and family cohesion across generations.

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 Thomas Monroe:

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

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

Disclaimer:

(0:00) Introduction (4:40) Understanding trusts: Who needs them and use cases (6:43) Tax considerations in trust planning (9:15) Tackling the "trust fund baby" stereotype and parenting (14:29) Fostering children's independence and passions (19:57) Trust structuring best practices and life exploration (22:30) Trust control vs. tax benefits and trustee independence (27:45) Institutional trustees and dealing with mortality (31:50) Managing trust complexity and administration (35:00) Gaining insights from diverse client experiences (37:20) Lessons from the successful and spotting opportunities (41:00) Key takeaways and choosing the right trustee (43:30) Closing remarks

EP269: The $350M 30-Year Fund Model Dec 24, 2025

Show notes

What happens when you throw out the playbook of traditional private equity and instead build businesses with permanent capital, no exits, and no management fees? In this episode, I talk with Brent Beshore, founder and CEO of Permanent Equity, about a radically different approach to investing that focuses on ownership, compounding, and alignment with operators over decades—not years. Brent explains why avoiding leverage and fees isn’t just philosophically different but materially better for long-term outcomes, how Permanent Equity partners with founders who want legacy and culture to endure, and why patient reinvestment beats short-term optimization. We break down how permanent capital accelerates growth, how to think about cash flow vs. IRR optics, and the unique investor mindset required to succeed outside the traditional private equity model.

Highlights:

Why Permanent Equity uses permanent capital instead of typical PE fund structures
How removing planned exits changes decision-making and drives better outcomes
No management fees and minimal debt: aligning incentives with operators
The power of long-term compounding inside small businesses
Why distribution timing matters less than reinvestment discipline
How culture and legacy factor into acquisition decisions
The “cell phone test”: evaluating leadership and partnership quality
Using downturns to make strategic progress rather than panic reactions
Why cash flow is the core driver of long-term wealth creation
How Permanent Equity thinks about growth vs. margin optimization
Lessons on patience, discipline, and the psychology of long-term investing

Guest Bio:

Brent Beshore is the founder and CEO of Permanent Equity, an investment firm that acquires and builds small businesses with permanent capital and a long-term orientation. Unlike traditional private equity, Permanent Equity doesn’t plan exits or charge management fees, instead focusing on sustained cash flow growth, minimal leverage, and deep partnership with operators. Brent has spent his career refining this approach to deliver compounding outcomes across cycles by aligning incentives between investors and founders and giving businesses the time horizon they need to thrive. Under his leadership, Permanent Equity has developed a reputation for thoughtful acquisitions, disciplined reinvestment, and a culture-first approach to building enduring companies.

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 Brent Beshore:

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

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

Disclaimer:

(0:00) Introduction (1:31) Compounding growth and institutional investor perspectives (4:34) No management fee structure and staff incentives (7:05) Responsible use of debt and industry buying opportunities (12:51) Differentiating from traditional private equity (16:02) Portfolio diversity and the cell phone test (20:07) Handling difficult personalities and problematic investments (23:22) LP relationships, trust, and long-term business views (28:28) The importance of quality in investments (30:55) Closing remarks

EP268: Inside LP Psychology: How Great GPs Raise Capital in 2025 Dec 23, 2025

Show notes

Why do so many strong GPs struggle to raise capital today and what actually separates fast, oversubscribed fundraises from stalled ones? In this episode, I talk with Alexander Russ, Senior Managing Director at Evercore and Head of North America for the firm’s Private Funds Group, about what really drives fundraising success in today’s crowded private markets. Alex breaks down the psychology of LP decision-making, why momentum in the first close matters more than almost anything else, and how the best GPs differentiate themselves through narrative, preparation, and credibility rather than fee discounts. We dive into why fundraising is ultimately a momentum machine, how to engineer demand early, and why trust—built over years—can be lost in a single raise.

Highlights:

Why the first close determines the outcome of an entire fundraise
The three golden rules of fundraising: preparation, control, and narrative
Why LPs invest based on excitement, not fear or fee discounts
How oversupply of GPs has changed LP behavior
The real meaning of “nailing the narrative” in the first 5 minutes
Why momentum beats aspiration when setting fund size targets
How credibility compounds or collapses across fundraising cycles
The danger of weak first closes and getting stuck “in the doldrums”
Why LP relevance matters more than broad outreach
How placement agents actually add value by filtering, not flooding

Guest Bio:

Alexander Russ is a Senior Managing Director at Evercore and Head of North America for the firm’s Private Funds Group, which he helped found in 2010. He advises general partners on competitive positioning, fundraising strategy, and execution across private equity, credit, infrastructure, and alternative strategies. Prior to Evercore, Alex worked at Neuberger Berman and Lehman Brothers, where he focused on alternatives advisory, capital raising, and distribution of hedge fund and liquid alternative products across the U.S. and Europe. He began his career in investment banking at Lehman Brothers and graduated with honors 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 Alexander Russ:

LinkedIn:https://www.linkedin.com/in/alexander-russ-610a0939/

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

Disclaimer:

(0:00) Introduction (1:49) Key factors for a successful first close and strategies without fee concessions (6:07) The role of excitement and fear in LP investment decisions (9:30) Importance of credibility, long-term relationships, and a compelling narrative (18:25) Evolving fundraising strategies in a competitive market (24:53) Building credibility and effective communication with LPs (31:49) Best practices for the first meeting with an LP and setting fund targets (37:47) Improving the efficiency of the fundraising process and consequences of missing targets (40:09) Raising a smaller fund versus a bigger target and expedited processes (42:10) Golden ratio in LP cutbacks and securing allocations impact (44:47) Balancing LP relationships and demand with ideal outcomes (46:05) Importance of storytelling and relationships in fundraising (46:34) Value of placement agents for GPs (47:30) Closing remarks

E267: Why 95% of LPs Misread Private Market Returns Dec 22, 2025

Show notes

Do private markets actually outperform public markets once you properly adjust for risk or is that belief built on flawed data? In this episode, I talk with Dr. Gregory W. Brown, one of the leading academic researchers in alternative investments, about what decades of data really say about private equity, venture capital, and risk-adjusted returns. We break down why private-market performance is so hard to measure, how tools like the Kaplan–Schoar PME changed institutional thinking, and what investors misunderstand about beta, volatility, and alpha. Greg also explains why buyouts and ventures behave very differently, how fund size and geography affect outcomes, and what this research implies for building diversified portfolios today.

Highlights:

Why alternatives are still under-researched compared to public markets
The core data problem in measuring private-market returns
How the Kaplan–Scholar PME creates apples-to-apples comparisons
Buyouts vs. venture: radically different risk profiles
Why buyout funds show positive alpha and venture largely does not
What beta actually measures (and why volatility is misunderstood)
The risk of ruin in high-beta, undiversified portfolios
Why small funds have higher upside but require real manager selection skill
Persistence of returns: partners matter more than firms
How public-market bubbles change private-market relative performance

Guest Bio:

Gregory W. Brown is a Distinguished Professor of Finance at UNC Kenan-Flagler Business School and one of the world’s leading experts on alternative investments, financial risk, and derivatives. He is the founder and research director of the Institute for Private Capital and has held leadership roles including Executive Director of the Kenan Institute of Private Enterprise. Greg’s research has been published in top academic and practitioner journals, and he serves on the board of the CAIA Association. His work bridges academia and practice, helping institutional investors better understand private markets through rigorous, data-driven analysis.

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 Gregory W. Brown:

LinkedIn: https://www.linkedin.com/in/gregory-brown-unc/

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

Disclaimer:

(0:00) Introduction (2:00) Explanation and Insights from the Kaplan Shore Index (7:04) Risk and Alpha: Buyouts vs. Venture Capital (10:39) Fund Size and Returns Dispersion in Buyouts (15:08) Persistence of Returns and Incentives in Public Pension Investments (19:44) Value Creation Skills and the Impact of the Mag Seven (22:00) Future Outlook and Historical Performance in Private Equity (23:27) Game Theory, Valuations, and Diversification Strategies (25:05) Closing remarks

E266: J.P. Morgan CIO: Mistakes Top Investors Make Dec 19, 2025

Show notes

Why do most investors fail at the exact moments when staying invested matters most—and how can options help fix that? In this episode, I talk with Hamilton Reiner, Managing Director at J.P. Morgan Asset Management and CIO of the U.S. Core Equity Team, about how options can be used not for speculation, but to create discipline, manage risk, and help investors stay invested through market volatility. Hamilton shares lessons from more than three decades managing equities and derivatives, explains why volatility is misunderstood, and breaks down how hedged strategies, rebalancing, and risk-based portfolio construction can dramatically improve long-term outcomes—without requiring heroic market timing.

Highlights:

Why options are about precision, not leverage
Hedging vs. income: the two primary institutional use cases for options
How downside buffers help investors stay invested during drawdowns
Why volatility is a feature of equities, not a flaw
The biggest behavioral mistakes investors make in up and down markets
Why missing the best days destroys long-term returns
How rebalancing quietly outperforms market timing
The role of options inside a modern 60/40 portfolio
Why risk tolerance—not asset allocation—should come first
Lessons from 2008, 2020, and decades of market cycles
The underrated power of compounding and staying in the game

Guest Bio:

Hamilton Reiner, managing director, is CIO of the U.S. Core Equity Team, Head of U.S. Equity Derivatives for J.P. Morgan Equity Asset Management, and a portfolio manager. He has been managing U.S. equities and U.S. equity derivatives for over 30 years, at firms such as Barclays Capital, Lehman Brothers, and Deutsche Bank. He started his career at the options investing firm O’Connor and Associates, where he developed his passion for derivatives investing. Hamilton obtained a B.S.E. in Finance from the Wharton School of the University of Pennsylvania.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in 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 Hamilton Reiner:

LinkedIn: https://www.linkedin.com/in/hamilton-reiner-7033594b/

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

Disclaimer:

(0:00) Introduction (0:32) Understanding Options: Strategies and Historical Use (4:20) Managing Stock Gains and Behavioral Biases in Investing (8:16) The Importance of Risk Tolerance and Market Timing (18:27) Decision-Making Challenges in Institutional Investment (22:17) Market Uncertainty and the Role of the VIX (24:14) Volatility, Investment Sizing, and Portfolio Integration (30:18) Market Cycles, Behavioral Biases, and Career Advice (38:23) Key Investment Lessons and the Power of Compounding (43:09) Closing remarks

E265: What the Coach to Sequoia, A16Z and Benchmark Learned About Power and People Dec 18, 2025

Show notes

Why do the most successful investors and founders still miss their best opportunities—and how much of that comes down to poor relationship management? In this episode, I talk with Patrick Ewers, founder of Mindmaven, about why relationships—not intelligence or effort—are the true limiting factor in professional success. Patrick shares lessons from being an early employee at LinkedIn under Reid Hoffman, coaching partners at top firms like Sequoia and Andreessen Horowitz, and building a systemized approach to relationship management that scales. We break down why important things lose to urgent ones, how delegation and leverage unlock effectiveness, and why small, consistent actions compound into billion-dollar outcomes.

Highlights:

Why relationships are the highest-leverage asset in investing and leadership
The “importance vs. urgency” trap that causes missed opportunities
How poor follow-up—not bad judgment—creates most investing regrets
Practical delegation systems that free up 10–12 hours per week
Why dictating follow-ups is more thoughtful than typing them
Inbox shadowing and decision triage for leaders
How to make people feel valued without fake niceness
Why efficiency enables deeper, more authentic relationships
The role of thinking time (“white space”) in elite performance
Why relationship management is the CEO’s final job

Guest Bio:

Patrick Ewers is the founder of Mindmaven, an executive coaching firm focused on helping leaders unlock their full potential through relationship management. He was one of the earliest employees at LinkedIn, working closely under Reid Hoffman, and later became one of Silicon Valley’s most sought-after relationship coaches. Over the past 15 years, Patrick has coached hundreds of founders, executives, and investors, including leaders from firms such as Sequoia Capital, Andreessen Horowitz, Benchmark, and First Round Capital, as well as companies like Reddit, Roblox, and Thumbtack. He is the author of Radical Delegation and has been recognized by Forbes as one of Silicon Valley’s top relationship management experts.

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 Patrick Ewers:

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

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

Disclaimer:

(0:00) Introduction (1:00) Early career and importance of relationships in business (2:40) Challenges and consequences of neglecting relationships (6:50) Best practices for managing and delegating relationships (10:48) Techniques for efficient business communication (18:25) Balancing transactional and thoughtful relationships (24:29) Strategies for effective meetings and scheduling (27:08) Principles and tools for effective delegation (35:59) Psychological aspects and predictability in email management (41:07) Democratizing executive-level efficiency and avoiding micromanagement (44:26) Leveraging recruiting for sustainable advantages (47:32) Role of relationship management in founding a company (49:09) Best practices for unstructured thinking and managing time (54:19) Overcoming work ambiguity and optimizing thinking environments (55:47) How to collaborate with industry experts (57:36) Closing remarks

E264: The Asymmetric Edge: Generating Alpha in Venture Dec 17, 2025

Show notes

How do the best venture investors consistently spot unicorn founders before the rest of the market even knows they exist? In this episode, I talk with Jamie Lee, Co-Founder and Managing Partner of Tamarack Global, about sourcing asymmetric deal flow in deep tech and why founder referrals are the single strongest signal of future breakout companies. Jamie explains how Tamarack applies hedge-fund-level diligence at the seed stage, why intuition and pattern recognition matter as much as data, and how concentrated conviction—combined with relentless research—drives their unusually high unicorn hit rate. We also explore humanoid robotics, labor automation, and why the next industrial revolution is already underway.

Highlights:

Why founder referrals outperform every other sourcing channel
Venture beta vs. true asymmetric alpha
Applying hedge fund diligence to pre-seed and seed investing
Why most early-stage investors under-diligence founders
The power of intuition and “gut scores” in decision-making
Lessons Jamie learned from Philippe Laffont at Coatue
Why long-term time horizons matter more than near-term metrics
The humanoid robotics market and the $40T global labor opportunity
Playing offense by preempting rounds in breakout companies
Why conviction beats caution early in an investing career

Guest Bio:

Jamie Lee is the Co-Founder and Managing Partner of Tamarack Global, an early-stage deep-tech venture capital firm investing across defense, aerospace, robotics, advanced manufacturing, AI, and the energy transition. He began his career in derivatives at Goldman Sachs, advised technology companies in special situations at JPMorgan, and later managed a $1.5 billion long/short equity portfolio at Coatue Management. Jamie holds a B.A. in Economics from Williams College and an MBA from Columbia Business School, where he also completed the school’s Deep Value Investing program.

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 Jamie Lee:

LinkedIn: https://www.linkedin.com/in/jamie-lee-77430382/

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(0:00) Introduction (0:11) Jamie Lee's sourcing strategy and founder referrals (4:19) Winning competitive investment rounds and the role of due diligence (10:07) Insights from SpaceX and the humanoid robot space (15:34) Learnings from venture funds and lessons from Philippe Lafont (24:19) The interplay of gut instinct and social psychology in investing (30:12) The importance of diligence and pattern matching in manager selection (33:04) Advice for younger investors and predicting high-value outcomes (37:50) Confidence in investment picks and closing remarks (38:05) Closing remarks

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