How I Invest with David Weisburd

By David Weisburd

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

4.3

4848 ratings

Download on the App Store

Download on the App Store

Get it on Google Play

FAQs about How I Invest with David Weisburd:

How many episodes does How I Invest with David Weisburd have?

The podcast currently has 184 episodes available.

How I Invest with David Weisburd episodes:

June 30, 2025E181: Why Portfolio Construction Beats Manager Selection w/$7 Billion CIO
In this episode, I speak with T.C. Wilson, Chief Investment Officer of The Doctors Company (TDC Group), the nation's largest physician-owned medical malpractice insurer with $7 billion in assets under management. T.C. shares how he built an internal investment office, how insurance investing differs from endowment and foundation models, and why he treats surplus like an endowment portfolio.
We dive into his framework for portfolio construction, his views on innovation in asset management, the underrated value of evergreen structures, and the specific ways GPs can tailor their approach to win over insurance LPs. T.C. also shares why he’s cautious on large-cap private equity, how he thinks about downside protection, and what extreme ownership has taught him as a leader.
If you want to learn how a CIO with decades of experience invests across public and private markets with an eye toward solvency, surplus growth, and long-term resilience, you’ll want to listen to this one.
Highlights:
T.C.’s path from Mercer to CIO of TDC Group
Building an internal consulting-style investment team
What makes insurance companies unique LPs
Why surplus is treated like an endowment portfolio
Portfolio construction: 80% non-VAR, 20% “fun stuff”
How to think about investing as a taxable entity
The role of rated feeder notes in optimizing statutory reporting
What GPs often get wrong when pitching insurance allocators
Evergreen structures and the “virtue of illiquidity”
Why culture and leadership matter more than most realize
--
Guest Bio:
T.C. Wilson is the Chief Investment Officer of The Doctors Company (TDC Group), where he oversees more than $7 billion in assets under management. He joined the firm in 2017 after serving as an external investment consultant to the company for 18 years. Prior to TDC, T.C. worked at Mercer and led an institutional consulting group focused on insurance clients. He has over 35 years of experience in investment management and is known for his deep understanding of how to balance surplus growth, solvency, and risk-adjusted returns within the insurance framework.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Stay Connected: X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Thomas (T.C) Wilson: https://www.linkedin.com/in/thomas-t-c-wilson-ab70b7a/
Links:
TDC Group: https://www.tdcg.com/
--
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(2:15) Capital allocation: Insurance vs. Endowments & $3.2 billion surplus impact
(4:52) Tax considerations in portfolio construction
(6:06) Traits of successful GPs and regulatory support
(10:22) Rated feeder notes and attracting insurance investors
(14:31) Evolution of asset managers and TDC Group's current strategy
(20:35) Private equity insights and evergreen fund benefits
(25:50) Investment strategy for downturns and portfolio resilience
(30:34) Illiquidity's role and criteria for new PE manager investments
(33:12) Portfolio construction vs. manager selection debate
(37:38) General partners' practices and AI's future impact on asset management
(42:11) Investor and allocator perspectives: Overrated and underrated aspects
(45:12) Extreme ownership and its influence on company success
(49:29) The significance of principles and culture in firms
(50:09) Conclusion and contact details
(50:19) Closing remarks
...more
51min
June 27, 2025E180: How J.P. Morgan Asset Management Picks Winners in VC & Private Equity
What does it take to allocate billions in private markets—and what sets a top-tier LP apart?
In this episode, I speak with Patrick Miller, Executive Director and Portfolio Manager of J.P. Morgan Asset Management’s Private Equity Group, where he plays a central role in their alternatives platform, investing across venture capital and private equity. Patrick shares how a single energizing meeting with a Florida-based venture capitalist sparked his interest in the asset class and how his team has since built a differentiated barbell strategy combining legacy tier-one firms and new emerging managers.
We dive into what LPs can do to truly add value to GPs, why fund size and ownership matter, how AI is shifting capital dynamics, and what makes a venture firm truly “differentiated.”
Whether you're a founder, a new VC, or an allocator, this episode is full of real LP insights from one of the most thoughtful voices in the game.
Highlights:
How Patrick first got excited about venture capital (and why he still is)
What LPs bring to the table beyond capital
The three most important differentiators for emerging managers
Why J.P. Morgan Asset Management venture strategy uses a barbell approach
The effect of AI on venture capital’s capital stack
How small funds can outperform big ones—if you know what to look for
What Patrick looks for in private equity managers
The most important advice he’d give his younger self
--
Guest Bio:
Patrick Miller is an Executive Director and Portfolio Manager of J.P. Morgan Asset Management’s Private Equity Group, where he is responsible for portfolio management, investment due diligence, and business development. He joined J.P. Morgan in 2012 and has played a key role in sourcing and managing investments across venture capital, private equity partnerships, co-investments, and secondary opportunities. Patrick earned his BA from Northwestern University, where he studied Communications and Business Institutions and was a member of the varsity baseball team.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
--
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Patrick Miller: https://www.linkedin.com/in/patrick-miller-80386558/
Links:
J.P Morgan Asset Management: https://am.jpmorgan.com/us/en/asset-management/institutional/investment-strategies/alternatives/private-equity-group/
--
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(0:06) Patrick Miller's entry into venture capital and adding value as an LP
(3:01) Stability and institutional experience in venture capital
(4:36) Investing in emerging managers and conviction in their success
(9:06) Impact of AI on venture capital
(13:28) Examples of backed managers and investing in private equity
(20:35) Advice for new investors and closing thoughts
(22:37) Closing remarks
...more
23min
June 25, 2025E179: How UCLA's Endowment Wins in Private Equity w/Deputy CIO Michael Marvelli
Michael Marvelli leads the private markets strategy at the UCLA Investment Company, managing a portfolio that spans private equity, real estate, and real assets. But his route to institutional investing wasn’t linear.
Before UCLA, he spent time at Prudential and The Irvine Company in real estate and mortgage finance, and even helped launch a venture-backed startup as COO and CFO. That operating experience gives him a unique lens when evaluating managers today.
In this episode, we talk about how UCLA builds conviction in lower-middle-market GPs, how they manage dry powder and fund pacing, and what it was like spinning out UCLA’s investment office into an independent entity.
Highlights:
The origins of the UCLA Investment Company
What it took to build the team, processes, and governance from scratch
Why UCLA is drawn to undercapitalized and underfollowed private equity managers
How real estate and real assets fit into a long-term endowment portfolio
The importance of downside protection and flexible pacing in private markets
How being a startup COO informs his view on GP talent, decision-making, and alignment
What he looks for in truly “great” allocators and investors
--
Guest Bio:
Michael Marvelli is the Deputy Chief Investment Officer of the UCLA Investment Company, where he leads the firm’s private markets strategy, overseeing private equity, real estate, real assets, and credit. He joined UCLA in 2003 and played a key role in the 2011 launch of the UCLA Investment Company.
Before joining UCLA, Michael worked in real estate and mortgage finance at Prudential and The Irvine Company, and co-founded a venture-backed startup where he served as COO and CFO. He holds a BS from UC Berkeley’s Haas School of Business and an MBA from Northwestern’s Kellogg School of Management.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #assetmanagement
--
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Michael Marvelli: https://www.linkedin.com/in/michael-marvelli-9918557/
Links:
UCLA Investment Company: http://www.uclainvestmentcompany.org/home
--
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(1:46) Evolution of UCLA Investment Company's strategy
(2:29) Asset allocation and its impact on returns
(4:11) Manager selection vs. asset allocation strategy
(7:30) Exploring the lower middle market in private equity
(15:54) Challenges for endowments investing in the lower middle market
(20:55) Specialization and focus in endowment investment strategies
(25:50) Independent sponsor deals and search funds insights
(29:59) Portfolio construction and commitment strategies
(32:54) Investment deployment in the lower middle market
(34:37) Value creation strategies in lower middle market investments
(38:45) The influence of interest rates on private equity
(40:56) Defining the ideal GP in private equity
(44:03) The importance of sector specialization and operating executives
(50:12) Founder-operator rapport in the lower middle market
(54:54) Career advice for aspiring private equity professionals
(58:34) Emphasizing first principles in investment strategy
(1:02:48) Michael Marvelli's strategic thinking and personal strengths
(1:04:30) Closing remarks
...more
1h 5min
June 23, 2025E178: Elon Musk of Biotech: How David Berry Built 7 Unicorns
David Berry is one of the most prolific healthcare entrepreneurs of our time.
In this episode, we discuss his transition from scientist to founder to investor, what it takes to scale transformational health companies, and how his firm Averin is helping usher in the next wave of AI-enabled healthcare.
We also talk about his early experience launching a satellite at 14, how he's co-founded over 30 companies—including seven unicorns—and why patents, perseverance, and purpose are the trifecta behind lasting innovation.
Highlights:
“The Elon Musk of Biotech?” Why Sorov called David that—and how David approaches world-changing problems
From 0 to 7 Unicorns: What David looks for in the first year of a company that signals long-term greatness
Pivots vs. Distractions: How to recognize the “kernel of truth” that transforms strategy
The Power of Culture: Why early-stage hiring is make-or-break—and how his brother built an elite culture at TripleLift
Replacing Founders Is Overrated: How world-class companies scale with visionary founders still at the helm
Extreme Passion: The real signal that a team will stay late, even without being told
The Investor’s Edge: Why early and mid-stage inflection points are where true multiples are made
Averin Capital: His new firm focused on tech-driven health companies in the underserved growth stage
The Coming Wave in Alzheimer’s: Why he believes personalized medicine will finally unlock real progress
Product-Market Fit in Biotech? Why 60% of approved drugs still lose money—and how to avoid those pitfalls
--
Guest Bio:
David Berry is the Managing Partner and co-founder of Averin, a Boston-based investment firm focused on helping build the next generation of great technology-powered healthcare companies. Prior to Averin, he was a General Partner at Flagship Pioneering, where he co-founded over 30 ventures across life sciences and sustainability—including seven that became unicorns. He holds an M.D. from Harvard Medical School, a Ph.D. in Biological Engineering from MIT, and a B.S. in Brain and Cognitive Sciences from MIT. David is also the recipient of numerous honors, including MIT Technology Review’s Innovator of the Year and World Economic Forum Young Global Leader. He is the inventor on over 200 patents and helped launch a satellite at age 14.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#venturecapital #vc #startupsuccess #biotech #assetmanagement
--
Stay Connected:
Twitter/X:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
David Berry: https://www.linkedin.com/in/davidberrymdphd/
Links
Averin: https://www.averincapital.com/
--
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(3:21) Drive, perseverance, and strategic pivots in entrepreneurship
(7:25) Company culture and founder roles during growth and scaling
(15:09) Identifying entrepreneurial superpowers and inner circle support
(17:23) Transitioning from entrepreneur to investor principles
(21:29) Growth investing strategies and investor-management alignment
(25:43) Navigating biotech's business and financial challenges
(32:36) Skill stacking and venture capital dynamics in biotech
(37:30) Closing remarks
...more
45min
June 20, 2025E177:How a Small Endowment Invests like Harvard w/Rip Reeves
In this episode, I speak with Rip Reeves, CEO of Institutional Investor and former CIO of AEGIS Insurance Services. Rip brings over four decades of experience across investment management, insurance, and endowments. We discuss his unconventional path from Salomon Brothers to leading one of the most iconic platforms in the investment world, his views on the OCIO model, portfolio construction, the “art” of manager selection, and why he believes building authentic relationships matters more than ever in this industry.
We also cover his deep ties to LSU, how he uses qualitative signals (like waiting room conversations) in manager evaluations, and the future of Institutional Investor in a changing GP-LP landscape.
Highlights:
Why LSU’s endowment chose the OCIO model with Cambridge Associates
Rip’s view on optimal allocation for endowments — and why 40/30/30 isn't as rigid as it looks
The surprising importance of culture and hallway conversations when vetting asset managers
How Institutional Investor uses experiential events (like raft races) to build real trust
Rip’s perspective on how the public vs. private market divide is blurring — and what that means for allocators
Why fixed income is “back” for the first time since the GFC
The hidden value of his wife Susie’s honest feedback in his investment thinking
The one thing GPs should never do at an Institutional Investor event
--
Guest Bio:
Rip Reeves is the CEO of Institutional Investor, a leading global platform serving allocators, asset managers, and consultants through content, community, and convenings. Before joining II in 2023, he spent over 11 years as CIO and Treasurer of AEGIS Insurance Services. Prior to that, Rip was Global CIO of Argo Group and held senior roles at BNY Mellon Asset Management, J.P. Morgan Investment Management, and Salomon Brothers.
Rip serves on the LSU Foundation Board, teaches finance at LSU, and is an advisor to Northern Trust Asset Management and Preferred Mutual. A Louisiana native, he holds a B.S. in Marketing and an MBA from Louisiana State University.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
--
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Rip Reeves: https://www.linkedin.com/in/rip-reeves-1b725717/
Links:
Institutional Investor: https://www.linkedin.com/company/institutional-investor/
--
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(5:27) Importance of portfolio construction over manager selection
(11:23) Qualitative factors and company culture in manager selection
(21:59) Building relationships with asset managers
(24:58) Rip Reeves on Institutional Investor magazine's impact and event value
(31:33) David Weisburd's closing remarks and subscription call-to-action
(36:37) Best practices for GP and LP relationship building
(41:55) Touch points and allocations between GPs and LPs
(44:18) Leveraging Institutional Investor for GP benefits
(45:36) Learning about Institutional Investor with Rip Reeves
(46:01) Closing remarks
...more
47min
June 18, 2025E176: Beyond Harvard: The Financial Crisis Endowments are Facing
John Trammell has been on the front lines of institutional investing for decades. He’s managed capital for some of the largest families and organizations in the world—from family offices to the Episcopal Church—and in this episode, he explains the seismic shifts happening in the world of endowment and foundation investing.
We talk about secondaries, collateralized fund obligations (CFOs), the future of Bitcoin in institutional portfolios, and why concentration—not diversification—created most of the great fortunes.
This is one of the deepest conversations I’ve had on how the smartest long-term investors are thinking today.
Highlights:
Why top endowments are dumping assets in the secondary market
How secondaries give institutions a way to clean up bad manager exposure
The real reasons endowments need liquidity today
Why some schools are now selling private equity... to themselves
What a collateralized fund obligation (CFO) actually is
Why John believes we’re past the Swensen model—and what’s next
The truth about diversification (and when it fails you)
How to build conviction to survive the toughest market moments
Why cash is no longer a drag on portfolios
How to cultivate a “prepared mind” for the next black swan event
--
Guest Bio:
John Trammell is a seasoned institutional investor who has managed assets across public and private markets for decades. He currently leads investments for the Episcopal Diocese of New York and has previously managed portfolios for prominent family offices and foundations. John is known for his thoughtful, experience-driven approach to asset allocation, governance, and long-term investment strategy—and for his ability to distill complex ideas into timeless lessons.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #assetmanagement
--
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
John Trammell :https://www.linkedin.com/in/john-trammell-258723/
Links:
Episcopal Diocese of New York: https://dioceseny.org/
--
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(3:11) Liquidity and portfolio construction in university endowments
(5:26) Pros and cons of secondary fund investments
(7:09) Secondary market investment mistakes by institutional investors
(9:20) Asset quality tiers in secondary investing
(10:04) Execution of collateralized fund obligations
(13:02) Investment governance and alumni contributions
(19:54) Swenson model evolution and diversification strategies
(25:14) Portfolio management: Concentration vs diversification
(28:06) Assessing portfolio diversification strategies
(30:15) Bitcoin's role in portfolio diversification
(32:27) Cash and emotional challenges in investing
(35:18) Tactical strategies during market downturns
(36:23) Conviction's importance in investment decisions
(39:06) Institutional views on Bitcoin allocation
(51:13) Educating stakeholders on liquidity management
(54:06) The importance of investment education
(55:38) Embracing a prepared mind in investing
(57:43) Closing remarks
...more
58min
June 16, 2025E175: Elon Musk: 10 Billion Humanoid Robots by 2040? w/NEA Partner Aaron Jacobson
Aaron Jacobson is one of the most insightful thinkers at the intersection of AI, robotics, and cybersecurity—and in this conversation, he separates signal from noise. We explore the future of humanoids, the shifting threat landscape in cybersecurity, and why the next wave of industry-defining companies will be built on infrastructure, not just foundation models.
Aaron Jacobson is a Partner at NEA, where he invests in AI, cybersecurity, and cloud infrastructure. He’s backed companies like Databricks, Horizon3.ai and Veza, and previously worked in tech M&A at Qatalyst Partners. In this episode, we dive into what’s real vs. hype in AI, the future of humanoids, and where the biggest opportunities in infrastructure are emerging.
Highlights:
Why Elon’s humanoid prediction is “off by multiple orders of magnitude”
What’s missing for humanoids to move from hype to real-world deployment
The 3 biggest challenges in robotics—and why they’re so hard to solve
How open models vs. closed models will shape the future of AI value capture
Why NEA is doubling down on cybersecurity
What cyber threats will look like in 5 years (spoiler: it's terrifying)
Why pen testing and “exposure management” are the future of security
How AI agents could close the gap between defenders and attackers
What Aaron learned working with Frank Quattrone at Qatalyst
How NEA thinks about multi-stage investing and the future of venture
--
Guest Bio:
Aaron Jacobson is one of the most insightful thinkers at the intersection of AI, robotics, and cybersecurity—and in this conversation, he separates signal from noise. We explore the future of humanoids, the shifting threat landscape in cybersecurity, and why the next wave of industry-defining companies will be built on infrastructure, not just foundation models.
Aaron Jacobson is a Partner at NEA, where he invests in AI, cybersecurity, and cloud infrastructure. He’s backed companies like Databricks, Horizon3.ai and Veza, and previously worked in tech M&A at Qatalyst Partners. In this episode, we dive into what’s real vs. hype in AI, the future of humanoids, and where the biggest opportunities in infrastructure are emerging.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Aaron Jacobsob: https://www.linkedin.com/in/aaronejacobson/
Links:
NEA: https://www.nea.com/
--
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(4:18) Safety and industrial applications of humanoids
(9:01) Breakthroughs and acceleration in humanoid development
(9:38) Value capture in LLM ecosystems and Facebook's LAMA strategy
(14:04) Cybersecurity trends: ransomware and penetration testing
(17:23) AI's impact on cybersecurity and role of insurance
(20:30) Preventative cybersecurity measures and multifactor authentication
(25:48) Closing remarks
...more
28min
June 13, 2025E174: The State of Venture Capital in 2025: Insights from a $1.8B AUM Chairman and Co-Founder
In this episode of How I Invest, I speak with Arjun Sethi—Chairman and co-founder of Tribe Capital, Co-CEO of Kraken, and one of the sharpest thinkers in venture capital and crypto today. Arjun breaks down how he approaches investing in “N-of-1” companies, what most VCs get wrong about data, and why the traditional funding stages like “pre-seed” and “Series A” are being rewritten in real time.
We also go deep into Arjun’s frameworks for scaling world-class companies, the evolution of crypto in a changing political landscape, and the big bets he’s making at the frontier—including humanoid robotics.
Whether you're an allocator, founder, or just fascinated by the future of finance, this conversation is packed with sharp insights and original thinking.
Highlights:
Why Arjun views Tribe as an “operating system” for venture
What makes Kraken different from Coinbase and Binance
The critical difference between a market leader and an N-of-1 company
How Arjun uses leading indicators to invest ahead of revenue
The vision behind Termina, Tribe’s in-house data platform
What most investors get wrong about benchmarks
How tokenized equities could reshape global capital markets
Why humanoid robots could play a key role in defense and logistics
--
Guest Bio:
Arjun Sethi is the Co-Founder and Chairman of Tribe Capital, a venture capital firm managing $1.8 billion across stages. He is also the Co-CEO of Kraken, one of the world’s largest crypto exchanges. Arjun previously worked at Facebook, was a partner at Social Capital, and has founded multiple companies across consumer, enterprise, and deep tech. Most recently, he incubated Foundation Robotics, a humanoid robotics company building toward a future of self-sustaining technology.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Stay Connected:
Twitter/X:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Arjun Sethi: https://www.linkedin.com/in/asethi/
Links
Kraken: https://kraken.com/
Tribe Capital: https://tribecap.co/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(1:06) Differentiation of Kraken from other exchanges and crypto trading evolution
(6:00) Investing strategies: n of one companies vs market leaders
(8:00) Advancements in data utilization for early-stage investments
(11:47) Applying nuanced metrics to traditional and tech companies
(16:16) Knowing your market position and strategic growth
(18:23) Focus and product development in top companies
(20:13) Vertical integration trends in various sectors
(22:25) Strategies for competing with large venture firms and staying private
(27:33) Tokenization in venture capital
(29:49) Foundation Robotics: Mission and challenges
(32:54) Future of humanoid robots in industry and defense
(33:19) Closing remarks
...more
35min
June 11, 2025E173: Billionaire Michael Loeb on Risk, Innovation, and Never Giving Up
What happens when you get fired from one of the most prestigious media companies in the world at age 36? For Michael Loeb, it meant inventing a new category in subscription services, launching one of the earliest venture studios, and incubating Priceline—one of the internet’s first great successes.
In this episode, I speak with Michael Loeb, founder of Loeb.nyc, about how getting fired from Time Inc. led to the $800M sale of Synapse back to Time, his early partnership with Jay Walker to incubate Priceline, and what makes a great entrepreneur. We also dive into how Loeb.nyc works, the role of trust and pivots in building companies, and why pattern-matching VCs often get it wrong.
Michael doesn’t hold back. He’s honest, funny, and full of war stories from decades of building companies—and backing founders through multiple lives.
Highlights:
How getting fired from Time Inc. pushed Michael into entrepreneurship
Reinventing subscriptions with continuous service and beating inertia
The origins of Priceline and early internet innovation
Why successful entrepreneurs are often “unemployable”
The venture studio model behind Loeb.nyc and its high hit rate
How to know when an old idea is worth reviving
Why safety and trust are essential for early-stage teams
Navigating pivots and replacing founding teams
The evolving role of small teams in the AI era
--
Guest Bio:
Michael Loeb is the founder and CEO of Loeb.nyc, a venture collective that builds, funds, and operates startups. Through Loeb.nyc, he has helped launch and scale dozens of companies by combining capital, talent, and shared services in a single ecosystem designed to dramatically improve the odds of success.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Stay Connected: X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Michael Loeb: https://www.linkedin.com/in/michaelloeb1/
Links:
Loeb.nyc: https://www.loeb.nyc/
--
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(0:09) Michael Loeb's journey from Time Warner to entrepreneurship
(2:17) The birth of subscription services and Time Warner acquisition insights
(4:07) The essence of entrepreneurial disagreeableness and innovation
(7:40) The story behind Priceline's creation with Jay Walker
(20:06) Recognizing the right timing for business ideas
(23:16) Key factors for a company's sudden growth
(27:00) The importance of adaptability and pivoting in business
(32:00) Leadership strategies in emerging companies
(34:47) Embracing reinvention for achieving product-market fit
(35:41) The role of small teams in company scaling
(38:13) Debunking the starving entrepreneur myth
(40:03) Understanding the entrepreneurial drive to succeed
(43:22) The American entrepreneurial ecosystem
(46:03) Work-life balance for entrepreneurs
(48:36) The impact of success on perception
(50:43) Michael Loeb's parting wisdom and call for ideas
(52:16) Analyzing success rates and VC partnerships
(53:53) Impact of the NYC mayoral race on the entrepreneurial scene
(56:53) Lessons from founding billion-dollar companies
(57:16) Closing remarks
...more
58min
June 09, 2025E172: How Cannabis Beverages are Disrupting the Alcohol Industry w/Sasha Pieterse
Sasha Pieterse might be best known for her acting career — but behind the scenes, she’s been building a beverage empire.
In this episode, we dive deep into how Sasha's personal health journey led her to launch Hippie Water, a hemp-derived THC beverage brand that’s now in 140+ stores across 9 states. We talk about what it takes to transition from Hollywood to the CPG world, why Gen Z is drinking less alcohol, and how Sasha is redefining what it means to be a “celebrity founder.”
This conversation goes beyond cannabis — it’s about leadership, authenticity, and building brands with staying power.
Highlights:
Why Sasha stopped drinking alcohol — and how cannabis changed her life
The inspiration behind Hippie Water and how it fills a social gap
How she scaled to 140 stores in under 9 months
The science vs. stigma behind cannabis and hemp-derived THC
Gen Z’s changing relationship with alcohol
What it’s really like to fundraise as a first-time, celebrity CEO
Why Sasha believes your team is your real moat
How she balances acting, entrepreneurship, motherhood, and hosting her podcast Women in the Nude
--
Guest Bio:
Sasha Pieterse is an actress, entrepreneur, and co-founder of Hippie Water, a hemp-derived THC beverage brand. She rose to fame on the hit TV show Pretty Little Liars and now splits her time between entertainment and building her consumer goods startup. She’s also the host of the Women in the Nude podcast, where she tackles taboo topics in women’s health, business, and identity. With 21 million followers across platforms, Sasha brings a unique voice to the cannabis space — combining influence with authenticity and mission-driven leadership.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #assetmanagement
--
Stay Connected:
Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Sasha Pieterse-Sheaffer: https://www.linkedin.com/in/sashapieterse/
Links
Hippie Water: https://www.hippiewater.com/
--
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview
(2:31) The science, politics, and decline in alcohol consumption among younger generations
(7:49) Hippie Water's journey from prelaunch to commercial success
(9:54) Insights into the day-to-day life and challenges of a CEO
(15:46) Understanding the target demographic and celebrity founder dynamics
(21:04) Authenticity, competitive advantage, and the industry potential of Hippie Water
(23:24) Navigating the regulatory landscape for hemp beverages
(26:30) Key lessons and best practices for new CEOs
(30:22) Merging corporate experience with cannabis entrepreneurship
(35:22) The transition from acting to podcasting and entrepreneurship
(39:43) Closing remarks
...more
44min

FAQs about How I Invest with David Weisburd:

How many episodes does How I Invest with David Weisburd have?

The podcast currently has 184 episodes available.

More shows like How I Invest with David Weisburd

Money Guy Show by Brian Preston and Bo Hanson

Money Guy Show

3,159 Listeners

Investing Insights by Morningstar

Investing Insights

490 Listeners

Motley Fool Money by The Motley Fool

Motley Fool Money

3,178 Listeners

Masters in Business by Bloomberg

Masters in Business

2,172 Listeners

The Meb Faber Show - Better Investing by The Idea Farm

The Meb Faber Show - Better Investing

937 Listeners

The Investing for Beginners Podcast - Your Path to Financial Freedom by By Andrew Sather and Dave Ahern | Stock Market Guide to Buying Stocks like

The Investing for Beginners Podcast - Your Path to Financial Freedom

1,392 Listeners

Capital Allocators – Inside the Institutional Investment Industry by Ted Seides – Allocator and Asset Management Expert

Capital Allocators – Inside the Institutional Investment Industry

800 Listeners

NerdWallet's Smart Money Podcast by NerdWallet Personal Finance

NerdWallet's Smart Money Podcast

746 Listeners

The Long View by Morningstar

The Long View

880 Listeners

All-In with Chamath, Jason, Sacks & Friedberg by All-In Podcast, LLC

All-In with Chamath, Jason, Sacks & Friedberg

9,095 Listeners

The Personal Finance Podcast by Andrew Giancola

The Personal Finance Podcast

1,353 Listeners

Money Rehab with Nicole Lapin by Money News Network

Money Rehab with Nicole Lapin

1,727 Listeners

The Money Mondays by Dan Fleyshman

The Money Mondays

413 Listeners

Wake Up to Wealth by Brandon Brittingham

Wake Up to Wealth

33 Listeners

I am Charles Schwartz Show by Charles Schwartz

I am Charles Schwartz Show

272 Listeners