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

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The podcast currently has 250 episodes available.

How I Invest with David Weisburd episodes:

November 21, 2025E247: Why Wall Street Is Wrong About AI w/ Dan Ives
Is traditional valuation dead for the biggest winners of the AI era? Or have investors simply been looking in the wrong place?
In this episode, I talk with Dan Ives, Managing Director and Global Head of Technology Research at Wedbush Securities, and one of Wall Street’s most followed tech analysts. Dan has covered the software and technology sector for 25 years, becoming known for his bold, high-conviction calls on Tesla, Nvidia, Microsoft, and Palantir long before they became consensus.
We break down why Dan calls Tesla the world’s leading “physical AI” company, why he thinks AI is the largest tech transformation in 40–50 years, what investors miss when they rely only on spreadsheets, and how his pattern-recognition framework helps him spot multi-baggers years before the herd.
Highlights:
Why he views Tesla far beyond autos; autonomy, robotics, robo-taxis, and multi-trillion-dollar upside.
Why he believes AI is a 40–50 year mega-cycle with second- and third-order winners.
Why do great companies look expensive every year until suddenly they don’t.
On pattern recognition, global customer conversations, and signals that never show up in models.
Lessons from 2008, 2022, and sticking with calls through volatility.
Why Nadella, Musk, Karp, and Lisa Su are misunderstood and mispriced by Wall Street.
His 1–10 conviction framework and how he sizes up when inflection happens.
Where he’s looking for the next multi-baggers in the AI supply chain.
How setbacks early in his career reshaped his investing worldview.
His role as Chairman of ORBS (EightCo Holdings) and Worldcoin-aligned authentication.
Why he partnered with Snow Milk on a fashion collaboration and how “owning who you are” fuels differentiation.
Guest Bio:
Daniel Ives is the Managing Director and Global Head of Technology Research at Wedbush Securities, where he has been a senior equity research analyst covering the technology sector since 2018. Dan has spent 25 years on Wall Street following software, cloud, cybersecurity, mobile, and the broader enterprise tech ecosystem.
He is also the Chairman of EightCo Holdings (ORBS), focused on authentication and digital identity infrastructure aligned with the emerging AI era.
Dan is one of the most sought-after tech experts globally, regularly appearing on CNBC, Bloomberg, BBC, Fox Business, ABC, NBC, Sky News, France 24, NPR, and many other global outlets. He is frequently cited in The Wall Street Journal, The New York Times, Financial Times, Barron’s, Time, The Telegraph, and other major publications.
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/
Daniel Ives: https://www.linkedin.com/in/daniel-ives-542321a8/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Preview
(1:17) Dan Ives on the AI revolution, Tesla's market dominance, and valuation methodology
(5:10) The importance of long-term vision and global insights in tech investing
(10:52) The role of retail investors and the impact of market sentiment
(14:25) The significance of true believers and early adopters in investments
(16:13) Recognizing when an investment thesis is wrong and adjusting strategies
(22:32) Investment sizing, portfolio construction, and utilizing customer feedback
(26:16) Psychological biases and their effects on investor confidence
(27:06) Leveraging social media and conferences for investment insights
(28:31) Understanding power law returns and second/third order effects in the market
(32:20) Evaluating investment success: hit rates and the role of outliers
(34:09) Influencing stock narratives and decisions at the board level
(37:21) Identifying mispriced founder-led companies and embracing failures
(43:41) Dan Ives' personal background and approach to maintaining conviction
(47:48) Future projects at Wedbush and personal ventures
(49:19) Closing remarks
...more
51min
November 20, 2025E246: Private Equity in 2025: Fees, Rates, and the Law of Large Numbers
Is private equity still worth it — or has the industry scaled its way into mediocre returns?
In this episode, I talk with Nolan Bean, CFA, CAIA, Chief Investment Officer and Head of Portfolio Management at FEG Investment Advisors, an independent, employee-owned firm advising on $90+ billion in assets for endowments, foundations, healthcare systems, and mission-driven institutions. We dig into the state of OCIOs, interval funds, private equity, and why Nolan believes the lower middle-market still offers the clearest path to real alpha.
Nolan also breaks down the coming wave of 401(k) access to private markets, why large-cap buyout is structurally challenged, and how FEG uses a “crisis playbook” to lean into markets without pretending to time them perfectly.
Highlights:
How FEG advises on $90B+ across 300+ clients, mostly nonprofits.
OCIO incentives, risk-taking, and why some firms drift toward being too conservative.
Interval funds: easy access, hidden liquidity risks, and “Hotel California” redemptions.
Why large buyout PE faces pressure from high entry multiples, rates, and too much capital.
Why lower middle-market buyout still works: founder-led deals, ops value-add, less leverage.
Main risks in small companies: fragility, client concentration, and key-person exposure.
Factor models vs. real alpha: where Fama-French stops explaining PE returns.
Shrinking small-cap universe and why public markets may have adverse selection.
The coming 401(k) and retail flow into alternatives — and shrinking illiquidity premia.
FEG’s VFS (valuation, fundamentals, sentiment) crisis framework for drawdowns.
Four key risks: goal risk, market risk, illiquidity risk, and maverick risk.
Nolan’s top two lessons: don’t fight the Fed, and relationships compound.
Guest Bio:
Nolan Bean is the Chief Investment Officer and Head of Portfolio Management at FEG Investment Advisors, where he has worked since 2004. He leads portfolio construction, research oversight, and investment strategy across FEG’s OCIO and advisory clients. Nolan is both a CFA and CAIA charterholder. He holds a finance and quantitative analysis degree and an MBA from the University of Cincinnati.
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/
Nolan Bean: https://www.linkedin.com/in/nolanbean/
Links
FEG Investment Advisors: https://www.feg.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(0:28) Growth catalysts and criteria for RIAs and investment advisors
(2:13) Criticisms of OCIOs and conservative risk-taking
(3:59) Discussion on interval funds and private equity buyouts in 2025
(7:39) Challenges in large buyout funds and lower middle market opportunities
(16:23) Risks and benchmarking in lower middle market investments
(21:45) Democratization of private markets and 401(k) investments
(24:36) Illiquidity premium and institutional investors' response
(27:06) Identifying opportunities in out-of-favor sectors and portfolio construction
(31:07) Managing risk tolerance and market downturn strategies
(34:24) Behavioral finance and liquidity in portfolio management
(37:18) Evaluating hedge funds and strategies for market downturns
(41:21) Diversification benefits and long-term market trends
(44:03) Public policy influence on markets and timeless investment advice
(47:55) Interest rates' impact on asset prices and politicians' market influence
(53:14) Investing during crises and the importance of relationships
(56:18) Venture capitalists, reciprocity, and value in relationships
(58:22) Closing remarks
...more
1h
November 18, 2025E245: From $0 to Billions in a Regulated Market
How do you build a multibillion-dollar company from scratch, walk away at the peak, and reinvent your life around purpose, generosity, and impact?
In this episode, I talk with Pete Kadens, one of America’s most respected first-generation wealth creators and one of the leading philanthropists focused on closing education and opportunity gaps across the U.S. Today.
Pete and I dive into how he built Green Thumb Industries (GTI) into a multibillion-dollar cannabis company, the unsexy strategies that made it work, and why choosing overlooked markets and consumers unlocked massive profit. We cover the power of ownership cultures, transparency, discipline frameworks, and why giving equity and education to employees creates extraordinary performance. We also explore the character transformation that led him to retire at 40.
Highlights:
The unsexy strategy behind scaling GTI into a multibillion-dollar operator
Why Pete targeted the 30–50-year-old female consumer long before the market noticed
How choosing Toledo instead of Chicago and Erie instead of Philadelphia created monopolistic advantages
The power of ownership cultures, ESOP-style alignment, and financial transparency
Why employees perform better when they are treated like owners
Pete’s shift from business success to a life of impact and philanthropy
The emotional toll, guilt, and clarity that led him to retire at 40
How he rebuilt his parenting philosophy: presence, character, and modeling discipline
Why “how you do anything is how you do everything” became his family standard
The timeless rule he lives by: the gap between “I should” and “I did”
Guest Bio:
Pete Kadens is a serial entrepreneur and dedicated philanthropist who currently serves as Chairman of The Kadens Family Foundation, a national charitable organization focused on closing education and wealth gaps. He is also the Founder and Co-Chairman of Hope Chicago, which is educating tens of thousands of underserved Chicagoans, and a key supporter of Hope Toledo, now serving more than 300 families with tuition-free college and trade-school pathways.
Pete is the Founder & Chairman of Warmer, a new social platform designed to create kind, supportive, and non-toxic peer-to-peer interaction. He also serves as Chairman Emeritus of StreetWise, one of Chicago’s largest homeless assistance organizations, and sits on multiple nonprofit and for-profit boards dedicated to social impact.
Pete is a 2019 Henry Crown Fellow at the Aspen Institute, one of the most selective fellowship programs in the world, recognizing leaders who create ventures solving society’s most challenging problems.
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/
Pete Kadens: https://www.linkedin.com/in/petekadens/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(0:19) Founding Green Thumb Industries and seizing opportunities in the cannabis industry
(2:08) Focusing on profit and choosing unsexy locations
(4:05) Targeting non-obvious customer segments and building partnerships
(7:44) Creating a disciplined framework for employee autonomy and engagement
(13:06) The importance and advantages of an employee ownership culture
(18:54) Transitioning from business to philanthropy
(19:47) Exploring different forms of wealth and personal fulfillment
(24:11) Balancing business success with personal life and trade-offs
(30:30) Role modeling, parenting philosophies, and teaching kindness
(37:40) Pursuing excellence, discipline, and lessons from Aspen Institute fellows
(41:41) Importance of suspending assumptions and embracing rest
(43:37) Valuing idiosyncratic excellence and embracing neurodivergence
(46:28) Turning aspirations into achievements and celebrating progress
(49:09) Concept of the minimum lovable product and reflecting on success
(50:44) Closing thoughts, gratitude, and how to follow Pete Kadens
(51:14) Closing remarks
...more
52min
November 17, 2025E244: Structural Alpha vs. Storytelling w/Alan McKnight
What separates elite CIOs from everyone else?
In this solo-style deep-dive conversation, I sit down with Alan McKnight, Executive Vice President and Chief Investment Officer at Regions Asset Management, to unpack how one of the industry's most respected allocators makes decisions across public and private markets. Alan oversees investment strategy, risk management, and portfolio construction across the firm's full platform — and brings decades of experience from leadership roles at Truist, SunTrust, Equitable, and Morgan Stanley.
We get into the realities of managing capital across different client types, how CIOs should think about illiquidity versus opportunity, where structural alpha truly comes from, and the process-driven framework Alan uses to separate skill from luck. If you're an allocator, founder, CIO, or LP, this episode lays out one of the cleanest mental models you'll hear on building durable long-term returns.
Highlights:
Why liquidity is the most misunderstood variable in portfolio construction
How allocators overestimate what they actually need.
The barbell playbook Alan uses to balance “hyper-liquid” and “hyper-private” exposures across client types.
How to generate structural alpha by lowering fees and accessing co-investments without adding unnecessary risk.
Why outcome-based thinking destroys CIO performance
How process accountability creates compounding advantages.
How to re-underwrite every position with brutal honesty, even when the mark looks terrible in the short term.
The alignment problem: why CIO tenures don’t match fund cycles and what it means for long-term returns.
The traits that separate world-class allocators from good ones
Why the unsexy work often creates the most alpha.
Alan’s advice to his younger self and the career decisions that would have accelerated his trajectory even further.
Guest Bio:
S. Alan McKnight, Jr., CFA is the Executive Vice President and Chief Investment Officer of Regions Asset Management, responsible for overall investment strategy, portfolio and risk management, and portfolio construction across $70BN in assets under management and $150BN in assets under advisement.
He is Chairman of the firm’s Investment Working Group and serves on the Asset Liability Committee, regularly representing Regions as its chief spokesperson on markets with outlets including CNBC, Bloomberg, FOX Business, The Wall Street Journal, The New York Times, and CNN Money.
Before joining Regions in 2015, Alan served as Head of Institutional Investments for Truist, Chief Investment Officer for SunTrust Institutional Investment Advisors, and held portfolio management roles at Equitable Asset Management and Morgan Stanley Asset Management.
He holds a B.A. in Economics from Washington and Lee University, an MBA from the University of Texas at Austin, and the Chartered Financial Analyst designation. Alan has served on boards including the Alliance Theatre, Cherokee Garden Library, The New Normal Society, and the Woodruff Arts Center Investment Committee.
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 #openlp #assetmanagement
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Alan McKnight: https://www.linkedin.com/in/s-alan-mcknight-jr-cfa-2b69993/
Links
Regions Bank: https://www.regions.com/personal-banking
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(1:05) Assessing illiquidity: willingness, capacity, and psychological aspects
(3:28) Private investment access for smaller investors and alternatives market
(6:42) Challenges for small and mid-sized managers in alternatives
(8:07) Interval funds: characteristics and practicality
(11:06) Liquidity needs and planning across market environments
(18:07) Alpha generation, manager selection, and behavioral economics
(22:45) Neurobiological and human bias in trading decisions
(25:48) Illiquidity benefits and structural alpha in private markets
(31:48) Liquidity management strategies and accountability in investing
(37:19) Team dynamics and incentive alignment in institutional investing
(42:00) Attracting and educating top investment talent
(45:03) Leveraging AI in investment research
(48:09) Evaluating and interacting with new managers
(51:22) Trust and reunderwriting in investment relationships
(54:10) Reflective advice and value in foundational tasks
(56:21) Closing remarks
...more
58min
November 16, 2025E243: The Gift Hidden Inside The Biggest Crisis
What happens when you’re forced to face your biggest fear?
In this solo episode, David Weisburd shares a deeply personal reflection on how moments of crisis can become the crucible that forges strength, resilience, and clarity. Drawing inspiration from Lloyd Blankfein’s reflections on the 2008 financial crisis, David explores why confronting your greatest fears—rather than avoiding them—can transform you into a more powerful, anti-fragile version of yourself.
From Joe Rogan’s public reckoning to founders who rebuilt stronger after near-death moments, this episode unpacks the paradox of hardship: how the moments that almost break you often become the foundation for your greatest breakthroughs.
Highlights:
Why your greatest fear may hold the key to your personal and professional growth
What Lloyd Blankfein learned from leading Goldman Sachs through the 2008 crisis
How Joe Rogan turned public backlash into renewed influence and clarity
Why “manufacturing crisis” might reveal what truly limits you
How top founders come back stronger from near-death experiences
The mindset shift that turns fear into fuel for anti-fragility and leadership growth
Host Bio:
David Weisburd is the founder of Weisburd Capital and the host of the How I Invest podcast. Previously, Mr. Weisburd was a Partner and Head of Venture Capital at 10X Capital, where he led notable firm investments into Robinhood, Honeybook, Palantir, and DraftKings. Mr. Weisburd founded Growth Technology Partners, a solo-GP venture firm, which was acquired by 10X Capital.
Prior to his venture capital career, Mr. Weisburd was on the founding teams of two venture-backed technology startups, iSocket (acquired by Rubicon Project (NYSE: RUBI)) and RoomHunt (acquired by RentLingo).
Mr. Weisburd served as a member of the board of directors of 3 publicly-traded companies.
Mr. Weisburd received an MBA from Dartmouth’s Tuck School of Business, and a master’s in psychology from Harvard 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].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
Stay Connected:
X / Twitter:@dweisburd
LinkedIn:https://www.linkedin.com/in/dweisburd/
Weisburd Capital: https://www.linkedin.com/company/weisburd-capital
How I Invest: https://howiinvestpodcast.com/episodes
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(0:30) Reflection on Lloyd Blankfein's career, antifragility, and confronting challenges
(2:42) Closing remarks
...more
4min
November 14, 2025E242: How an 18-Year-Old Harvard Dropout Raised $47M
Can a 23-year-old Harvard dropout build the next billion-dollar company?
In this episode, I talk with Steven Wang, founder and CEO of dub, a U.S. copy-trading platform that lets you automatically mirror the portfolios of real investors and traders. We get into why he thinks most retail investors won’t get good at stock picking, why the future is about picking people, not tickers, and how dub is trying to turn social-media-driven, mimetic trading into better financial outcomes. We also cover the retail trading boom, meme stocks, the “retail army,” what dub’s top creators actually do to generate alpha, and how a creator-led marketplace for strategies could reshape how the next generation builds wealth.
Highlights:
Why dub is America’s first regulated copy-trading platform and how it works
The retail trading boom: meme stocks, FOMO, and 20–35% of daily volume coming from retail
How Gen Z thinks about wealth, risk, and becoming a millionaire through investing
What dub’s top creators actually do to generate alpha (micro-caps, swing trading, social influence)
How momentum trading can become real value (GameStop, Opendoor, AMC)
Steven’s founder journey: VR startup at 16, Harvard dropout, and raising $47M
Leadership lessons: moving from micromanagement to mission-driven culture
The Sisyphus mindset, meditation, and staying grounded during low moments
What Steven would tell his 2021 self about reinvention, feedback, and patience
Guest Bio:
Steven Wang is the founder and CEO of dub, a regulated U.S. copy-trading platform that lets investors follow and automatically mirror the portfolios of real investors and creators. Dub is owned and operated by DASTA Inc., with advisory services provided by dub Advisors, LLC, an SEC-registered investment adviser, and brokerage services provided to retail customers by DASTA Financial, LLC, an SEC-registered broker-dealer and FINRA/SIPC member, with clearing through APEX Clearing Corporation.
Dub has raised $47 million in total funding, including a $30 million Series A, and offers access to 200+ crowdsourced Creators with real, transparent track records that users can copy starting from small account sizes.
Before founding dub, Steven built and sold a VR startup he began as a teenager, worked briefly at Apple, and attended Harvard before leaving to focus on dub full-time.
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/
Steven Wang: https://www.linkedin.com/in/swangentr/
Links
Dub: https://www.dubapp.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(0:14) Retail investors' underperformance and the thesis behind Dub
(0:32) Historical context and explosion of retail trading
(1:19) Cultural zeitgeist, social media, and trading during COVID-19
(3:12) Dub's mission post-2022 crash and entrepreneurial journey
(5:15) Startups: Timing, market conditions, and young entrepreneurship challenges
(7:23) Scaling the business, culture, and hiring practices
(12:11) Anti-selling in interviews and wealth transfer to younger generations
(14:32) Simplifying investing and the importance of trust in decisions
(17:09) Broadening participation in wealth creation and investing habits
(19:20) Operationalizing trends and building a marketplace of strategies
(23:33) Impact of meme stocks and retail investor strategies
(27:11) Legal strategies behind traders' success and building a strong network
(35:50) Mindfulness, advice for entrepreneurs, and decision-making
(38:23) Balancing ambition, patience, and clarity of vision in startups
(41:00) Leadership strategies and the power of compounding efforts
(41:28) Closing remarks
...more
42min
November 13, 2025E241: How Spirits Became a $1 Trillion Alternative Asset Class
How do you turn whiskey barrels into an institutional asset class?
In this episode, I sit down with Giuseppe Infusino, Chief Investment Officer and Managing Partner at InvestBev Group, to explore how a real asset like aged whiskey is quietly becoming one of the most uncorrelated and profitable investments in alternative markets. From his early years at RVK advising multi-billion-dollar allocators to managing institutional portfolios in a niche category few understand, Giuseppe shares how InvestBev has built an entirely new asset class from the ground up.
We discuss the economics of whiskey aging, how barrel pricing creates asymmetric returns, and why alcohol performs differently across economic cycles. This conversation breaks down incentives, alpha generation, and how to educate LPs on emerging strategies long before they go mainstream.
Highlights:
The incentives that keep consultants from finding the “best and brightest” managers—and how RVK broke the mold
Why 90% of RVK’s fund allocations were self-sourced, and how that approach drives better returns
The conversation that led Giuseppe to co-found InvestBev—and how whiskey became a new institutional asset class
The real asset characteristics of whiskey barrels—and why they appreciate over time like fine art
How InvestBev’s analysis with Kellogg proved near-zero correlation between whiskey and traditional markets
Why barrel investments deliver equity-like returns with half the volatility of equities
How to educate LPs when creating a new asset class—and what early adopters get right
Why InvestBev’s edge comes from deep beverage-industry relationships across Bacardi, Molson, and Coors
The scaling lessons from Fund I to Fund V—and how institutional credibility compounds over vintages
Why operational excellence, data, and early hiring decisions define fund longevity
The best LP advice he ever received: “No investor ever complains about getting their money back.”
Guest Bio:
Giuseppe Infusino is the Chief Investment Officer and Managing Partner at InvestBev, where he leads the firm’s investment strategy, sourcing, diligence, and structuring processes across consumer brands, beverage services, and hard assets.
Prior to InvestBev, he spent over a decade managing institutional investment portfolios for prominent allocators deploying multiple billions in private markets. He holds an MBA in Marketing & Entrepreneurship from the Kellogg School of Management, Northwestern University, and a B.S. in Finance & Real Estate from the University of Wisconsin-Madison.
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/
Giuseppe Infusino: https://www.linkedin.com/in/giuseppe-infusino-331b198/
Links
InvestBev: https://www.linkedin.com/company/investbev/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(1:30) Incentive structures in consulting and investment staff
(3:20) Consultants and emerging managers
(4:55) Sourcing and transitioning to bourbon investments
(7:54) Market dynamics and correlation of bourbon investments
(10:27) Asset allocation in bourbon investing
(12:05) Educating LPs on bourbon investments
(14:15) First mover challenges in new asset classes
(16:21) Organizational influence on investment decisions
(17:14) Economics of alcohol production
(19:07) The three-tiered system in the alcohol industry
(19:30) Lessons from starting and scaling a fund manager
(21:11) Growth rates and transitioning to private credit
(25:43) Operational investments and valuation models
(28:27) Best LP advice and perspectives on capital return
(31:01) Utilization of AI in investment strategies
(33:14) Closing remarks
...more
34min
November 11, 2025E240: The Edge: Risk, Discipline, and Judgment in Venture
What separates great investors from generational ones—and how do you actually find the next Elon Musk?
In this episode, I sit down with Mike Annunziata, Founder & Managing Partner of Also Capital, a solo GP fund backing the world’s most ambitious hard tech founders. Before launching Also Capital, Mike spent years at the Cornell University Endowment, helping allocate over $1 billion across venture and private equity managers—giving him a front-row seat to what “world-class” really looks like.
We talk about how LPs identify the next top-decile fund managers, why the best founders are like amateur pilots, and how to find the tiny behavioral tells that separate the merely ambitious from the truly elite. From identifying credibility under pressure to understanding the physics of hard tech investing, Mike shares a rare, insider’s look at the art of backing outliers.
Highlights:
How working at the Cornell Endowment shaped Mike’s investor mindset and revealed what “world-class” really looks like
The difference between top-quartile and top-decile managers—and why early risk-taking defines greatness
Why founders who combine ambition with credibility are the ones who build generational companies
What venture investors can learn from Bain Capital Life Sciences and the power of early conviction
The “amateur pilot” framework: how to identify founders who take disciplined risks under pressure
Why great founders are magnets for talent—and how followership predicts success more than ideas
The difference between competitiveness, urgency, and toxic culture in startups
How AI is transforming hard tech—from edge computing to design cycles
What it takes to spot a breakout hard tech company before anyone else does
Why discipline—not deal-chasing—is the real driver of long-term venture success
Guest Bio:
Mike Annunziata is Managing Partner at Also Capital, where he invests in and supports hard-tech companies solving atomic scale problems—across aerospace, defense, robotics, advanced manufacturing, communications, mobility, and applied AI. Since 2019 he’s seeded companies now valued at over $2 billion including Radiant, Varda Space, K2 Space, and Northwood, which have collectively raised over $500 million.
Previously, Mike was Co-Founder & CEO of Farther Farms, a Series B startup out of Cornell University, and spent three years as Senior Investment Analyst at Cornell University’s Investment Office, allocating capital across venture and private funds. He holds a B.S. in Industrial & Labor Relations and an MBA from Cornell University’s Johnson Graduate 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/
Mike Annunziata: https://www.linkedin.com/in/mike-annunziata-12853bb/
Links
Also Capital: https://www.alsocapital.com
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(0:24) Understanding investment talent and managing risk
(0:54) Identifying world-class funds and great managers
(2:03) Example of early successful fund: Bain Capital Life Sciences
(3:26) Building a brand and competitive advantage in investing
(5:00) Traits of successful founders and top decile managers
(8:02) Investment edge and volatility in venture strategies
(12:27) Focus and diversification of Also Capital investments
(16:54) Nonconsensus views and breaking down ambitious projects
(19:04) High IQ and EQ in founders and early leadership signs
(24:08) Competitiveness, sense of urgency, and mission-driven motivation
(31:08) Impact of AI on hard tech startups and identifying big founders
(36:08) Attracting top talent and advising young founders
(41:10) Dynamics of high RPM vs. high gear in startups
(44:20) Timeless advice and understanding pitfalls for new VCs
(46:29) Balancing deal volume with founder quality and knowing your founders
(52:19) Closing remarks
...more
53min
November 10, 2025E239: FemHealth Ventures: Sara Crown Star on Redefining Success Beyond the Family Business
How do you turn purpose, legacy, and innovation into a single investing philosophy?
In this episode, I speak with Sara Crown Star, Venture Partner at FemHealth Ventures and President of SCS Innovations. Sara shares how her experience growing up in one of America’s most prominent families shaped her values as an investor and why she believes the next trillion-dollar opportunity lies in women’s health.
We discuss the evolution of FemHealth Ventures’ investment thesis, the creation of the “FemHealth Framework,” and how it’s redefining what women’s health means across drugs, devices, diagnostics, and AI-driven solutions. Sara also shares personal stories from her family’s legacy—how values like integrity, community, and purpose continue to drive generational success.
Highlights:
How FemHealth Ventures is redefining women’s health through the “FemHealth Framework”
How AI and data analytics are transforming fertility outcomes through Cercle, backed by Sheryl Sandberg
Why innovation in postpartum depression could save lives—and how Reunion Neuroscience is pioneering new treatment paths
The overlooked investment opportunity in women’s health—and how half the population remains underrepresented in clinical trials until 1993
What the Crown family’s story teaches about values, reputation, and resilience across generations
The founding lessons of Henry Crown during the Great Depression—and why character still compounds
How the Henry Crown Fellows Program at the Aspen Institute turns success into significance
Why purpose and meaning unlock the “sixth gear” for investors and founders
Advice for future generations: raising independent thinkers, building genuine friendships, and preserving family values
Guest Bio:
Sara Crown Star is a Venture Partner with FemHealth Ventures, a top-decile VC firm with $100 million in AUM, focused on advancing innovations in women’s health. FemHealth Ventures invests in companies developing drugs, devices, diagnostics, and digital/AI-enabled solutions. Sara is also president of SCS Innovations, which connects entrepreneurs with capital to bring new technologies to market. She serves on the board of 1871 (Chicago’s entrepreneurial hub), is a life trustee of the Erikson Institute, and is President of the Colonel Henry Crown Scholarship Fund. She is also a director of Musicians on Call, the Jewish United Fund of Chicago, the Ortus Foundation, and the Crown Family Foundation. Sara graduated with a B.S. from the University of North Carolina at Chapel Hill and a J.D. from Georgetown University Law Center. She also completed the Wexner Heritage Program and received an Executive M.B.A. 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/
Sara Crown Star: https://www.linkedin.com/in/saracrownstar/
Links
FemHealth Ventures: https://www.femhealthventures.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(1:18) Sara's passion for women's health and career beginnings
(2:34) Investment highlights: Gynesonics and Reunion Neuroscience
(7:28) Women's exclusion in clinical trials and market potential
(9:13) Future trends and family values in women's health investing
(14:08) Community impact and the role of purpose in success
(22:23) Challenges of prominence and wealth management in the Crown family
(25:23) Closing remarks
...more
29min
November 09, 2025E238: Acting Fast and Slow
Why are we wired to chase quick wins instead of lasting breakthroughs—and how can investors reprogram that bias?
In this third solo episode, David Weisburd unpacks the neuroscience of decision-making and how understanding dopamine can dramatically change the way you operate as an investor, founder, or builder.
Drawing on insights from his conversation with Dave Fontenot of HF0, David explains why long-term rewards (“slow dopamine”) create compounding advantages while short-term hits (“fast dopamine”) destroy focus. He shares tactical strategies for building “monk mode” systems that protect deep work, how to avoid the illusion of productivity, and why the most valuable ideas require discomfort and delay before payoff.
This episode is about rewiring your brain for compounding—not con
Highlights:
How fast dopamine (short-term gratification) undermines long-term focus
Why slow dopamine is the neurological key to compounding performance
How to structure your day for deep work and “monk mode” productivity
Why checking emails or chasing small wins creates addictive behavior loops
How to identify the most important, non-urgent tasks that create 10x leverage
Why most founders confuse activity with progress—and how to fix it
The mental models behind HF0’s ability to 20x ARR in just 12 weeks
How to replace short-term dopamine hits with long-term focus triggers
What Ryan Hoover’s automation philosophy teaches about time leverage
How to act “slow” in a world addicted to fast—and win over decades
Host Bio:
David Weisburd is the founder of Weisburd Capital and the host of the How I Invest podcast. Previously, Mr. Weisburd was a Partner and Head of Venture Capital at 10X Capital, where he led notable firm investments into Robinhood, Honeybook, Palantir, and DraftKings. Mr. Weisburd founded Growth Technology Partners, a solo-GP venture firm, which was acquired by 10X Capital.
Prior to his venture capital career, Mr. Weisburd was on the founding teams of two venture-backed technology startups, iSocket (acquired by Rubicon Project (NYSE: RUBI)) and RoomHunt (acquired by RentLingo).
Mr. Weisburd served as a member of the board of directors of 3 publicly-traded companies.
Mr. Weisburd received an MBA from Dartmouth’s Tuck School of Business, and a master’s in psychology from Harvard 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].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
Stay Connected:
X / Twitter:@dweisburd
LinkedIn:https://www.linkedin.com/in/dweisburd/
Weisburd Capital: https://www.linkedin.com/company/weisburd-capital
How I Invest: https://howiinvestpodcast.com/episodes
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(3:50) Aligning business goals with slow dopamine and differentiating career paths
(4:59) Ryan Hoover's approach to problem-solving and long-term efficiency
(6:53) Dramatic upside of slow thinking and human evolution
(7:08) Closing remarks
...more
8min

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