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    Business

    How I Invest with 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, Stepstone, and other top limited partners.

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    Copyright: © Copyright 2025 How I Invest with David Weisburd

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    Latest Episodes:
    E173: Billionaire Michael Loeb on Risk, Innovation, and Never Giving Up Jun 11, 2025
    Show notes

    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 david@weisburdcapital.com.

    #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 david@weisburdcapital.com.

    (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

    E172: How Cannabis Beverages are Disrupting the Alcohol Industry w/Sasha Pieterse Jun 09, 2025
    Show notes

    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 david@weisburdcapital.com.

    #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 david@weisburdcapital.com.

    (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

    E171: SBIC Funds: How to Raise $175 Million for Private Equity & Credit Funds Jun 06, 2025
    Show notes

    This episode is a masterclass on one of the most powerful — and under-the-radar — capital structures in private markets: Small Business Investment Companies (SBICs). I’m joined by Brett Palmer, President of the Small Business Investor Alliance, and David Demeter, who helps manage Davidson College’s endowment. We dive deep into the SBIC program — a unique public-private partnership that lets private equity and credit funds access 2:1 fixed-rate, non-recourse leverage from the U.S. government. The result? LPs can access equity-like returns for credit-like risk, and fund managers gain scale without sacrificing strategy. Most people haven’t heard of it. That’s exactly why we did this episode.

    Highlights:

    • SBIC funds outperformed benchmarks by ~4% net IRR, per UNC-Chapel Hill study
    • SBICs access 10-year fixed-rate leverage at ~50–80 bps over Treasuries
    • Funds can borrow up to $175M with no refinancing risk
    • Net-of-fee returns can exceed gross-of-fee returns — due to leverage
    • Lower middle market is still inefficient, underprofessionalized, and rich with alpha
    • Davidson College uses SBICs to target 3x net MOIC — with less risk Program has grown from $2B to $50B+ in AUM since 2008
    • LPs include family offices, endowments, and banks — but few large institutions

    -- Guest Bio: David Demeter helps manage Davidson College’s endowment, where he leads investments across hedge funds, venture capital, and private equity. Davidson is known for its barbell strategy — combining high-performing venture and niche private strategies like SBICs.

    Brett Palmer is the President of the Small Business Investor Alliance (SBIA), the leading advocacy group for SBIC fund managers and investors. He’s been at the helm since 2008, helping modernize and grow the SBIC 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.

    #VentureCapital #VC #Startups #OpenLP #assetmanagement

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

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ David Demeter: https://www.linkedin.com/in/david-d-demeter-117aa913/ Brett Palmer: https://www.linkedin.com/in/brett-palmer-2160b95/

    Links: Davidson College: https://www.davidson.edu/ Small Business Investor Alliance: https://sbia.org/

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

    (0:00) Episode preview (1:20) SBIC performance metrics and leverage explanation (4:20) Benefits and growth of SBICs (7:41) SBIC funds' role in private credit, equity, and structural alpha (11:10) Lower middle market investments and economic impact (16:04) Backing and special features of SBIC leverage (18:33) SBIC program awareness and emerging managers (23:24) Challenges and eligibility for SBIC licensing (27:28) Davidson endowment's investment strategy (29:20) Hedge fund and venture capital investments in Davidson portfolio (31:12) Quant strategies and hedge fund allocation challenges (33:18) Resources for SBA funding and parting words (34:27) Closing remarks

    E170: How an AI Agent Is Outperforming VCs w/Andrew D’Souza Jun 04, 2025
    Show notes

    What if your venture partner could talk to a thousand founders a day — and actually listen? In this episode, I speak with Andrew D’Souza, the Founder/CEO (aka Creator) of Boardy and previously the founder and CEO of Clearco (formerly ClearBank). Andrew is building something entirely new: Boardy, an AI super-connector that lives across voice, chat, and email — and introduces people to each other. He describes Boardy as a principal, not an agent — a character with its own goals, who is building goodwill and helping founders, fund managers, LPs, and executives find each other in real time. And here’s the wild part: Boardy is already responsible for over ten multimillion-dollar deals, including helping HF0 select 3 of its 10 portfolio companies, and facilitating LP meetings for emerging fund managers.

    Highlights:

    • 3 of HF0’s 10 most recent investments came from founders surfaced by Boardy
    • Boardy has facilitated over 10 multimillion-dollar deals — including founder-investor and LP-GP introductions
    • VCs are using Boardy to filter inbound, diligence deals, and ideate thesis
    • Boardy works like a McKinsey partner: asking questions, forming opinions, connecting people
    • Designed as a “principal,” not a “tool” — Boardy has its own goals and judgment -Trained through over 50,000 conversations, Boardy’s match rate is compounding fast
    • Andrew’s team uses Boardy daily — including for hiring and internal decision-making
    • Boardy speaks over voice, chat, and WhatsApp — and conversations feel more like peers than prompts

    -- Guest Bio: Andrew D’Souza is the founder of Borty.ai, a voice-powered AI platform that connects people based on real-time, high-fidelity conversations. Previously, he co-founded Clearco (formerly ClearBank), where he helped pioneer revenue-based financing for e-commerce startups. Andrew is also a seasoned startup investor and advisor, and began his career at McKinsey & Co.

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

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

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

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Andrew D'Souza : https://www.linkedin.com/in/andrewdsouza/

    Links: Boardy: https://www.boardy.ai/

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

    (0:00) Episode preview (1:21) Bordy's role and application in venture space and team hiring (3:45) Bordy's experience with HF Zero accelerator and deal facilitation (8:00) Confidence in Bordy's model and matchmaking judgment (15:27) Improving fund performance and early use cases (19:12) Boardy's intelligence growth and internal company use (23:26) AI's impact on business operations and data analysis (25:02) Boardy's scalability and role in asset management (28:25) Boardy's creation, use cases, and product road map (33:39) Future integration of AI and humans in society (37:33) Boardy's market focus and compounding skills (41:28) Hiring at Boardy Inc. using Bordie (44:44) Closing remarks and contact information (46:35) Closing remarks

    E169: How to Build an Enduring Private Equity Franchise w/Alex Robinson Jun 02, 2025
    Show notes

    Alex Robinson is the Co-Founder and CEO of Juniper Square, a company transforming the private markets through technology and service. In this episode, we go deep into how he and his co-founders saw the opportunity to modernize fund administration, why the private markets are decades behind the public markets, and how Juniper Square is building for the future with AI agents. We also discuss how the best GPs scale trust with LPs, why the retail channel still hasn’t arrived in full force, and the challenges of building a system of record in a fragmented industry.

    Highlights:

    • How a FedEx delivery inspired Juniper Square
    • Why crowdfunding was a “dumb idea” and investor relations software was the wedge
    • Building trust with GPs in the early days
    • Why Juniper Square is both a tech and services company
    • The Pareto principle in fund admin automation
    • Why LP experience matters—especially for back-office users
    • Lessons from institutional LP demands and side letters
    • The power law of retail fundraising in private markets
    • What top GPs do to reinforce trust at every touch point
    • How Juniper Square is using AI agents to transform investor relations, fund admin, and portfolio decision-making

    -- Guest Bio: Alex Robinson is the Co-Founder and CEO of Juniper Square, a leading provider of investment management software for the private markets. Before Juniper Square, Alex was a serial entrepreneur in the clean tech space. He holds degrees from Harvard and Stanford, and today leads Juniper Square’s vision to bring the private markets into the digital age.

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

    #VentureCapital #VC #Startups #OpenLP #assetmanagement

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

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alex Robinson: https://www.linkedin.com/in/alexrob22/

    Links Juniper Square: https://www.linkedin.com/company/juniper-square/

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

    (0:00) Episode preview (1:05) Genesis and expansion of Juniper Square (3:12) Growth trajectory of private markets and the impact of the Jobs Act (5:14) Juniper Square’s contrarian view on crowdfunding and strategic focus (7:27) Evolution of Juniper Square’s target customers (10:45) Building a great product and intersection of technology in fund administration (14:45) Organizational design and customer service at Juniper Square (20:56) Juniper Square’s software tools and network effects (25:23) Diverse GP reporting methodologies and back-office experience (27:47) Retail investors' impact and shift in investor data expectations (33:53) Managing side letters and Juniper Square's business model (36:22) LP preferences and fee sensitivity in venture returns (41:17) Juniper Square's customer base and AUM privacy (45:39) Marketing strategies and growth of retail investment in alternative assets (51:28) Reinforcing trust with LPs and best practices for scaling relationships (57:12) Typical growth patterns and expansion strategies of GPs (1:02:57) Juniper Square's investment in AI and upcoming features (1:07:45) Closing remarks

    E168: How I Coach The Top 0.1% CEO's in Silicon Valley w/Alexis John d'Amecourt May 30, 2025
    Show notes

    Alexis John d'Amecourt is the coach behind some of the most iconic CEOs in tech today—including the founders of Substack, Eigenlayer, and Booksy. In this episode of How I Invest, I sat down with Alexis to explore what really makes great CEOs tick—and what causes them to fall apart. We talked about how founders can build trust, navigate emotional turbulence, lead organizations as they scale, and get unstuck when things feel overwhelming. Alexis also opened up about his own story—from being raised by his grandmother in D.C. after a turbulent childhood to becoming a three-time founder turned executive coach. This conversation is packed with tactical frameworks, powerful analogies, and a ton of heart.

    Highlights:

    • Why even the best CEOs need coaching—and what coaching actually looks like
    • The most common problems CEOs face at every stage of company growth
    • What to do when you’re stuck, overwhelmed, or panicked as a founder
    • The difference between managing and leading—and how to do both effectively
    • The one skill that top 10% employees all have in common
    • A powerful tactic for giving and receiving feedback that builds trust
    • What ego looks like when it helps vs. when it hurts
    • How childhood experiences shape founders—and how to turn that into fuel

    -- Guest Bio: Alexis John d'Amecourt is the founder of Mishory Method, an executive coaching firm that works with top CEOs and venture-backed founders around the world. His clients include the CEOs of Substack, Eigenlayer, and Booksy, among many others. A three-time founder himself, Alexis brings deep empathy and real operating experience to every conversation. I’ve seen firsthand how effective he is—and I’m excited to share this episode with you.

    Alexis was born into a lineage of remarkable minds and bold innovators. His great-uncle was Stanislaw Ulam, the renowned mathematician who made foundational contributions to nuclear physics—including a vital role in the development of the hydrogen bomb—and who pioneered the use of Monte Carlo methods.

    On his maternal side, Alexis was the great-great-great-grandson of Gustave de Ponton d’Amécourt, the French inventor and engineer who advanced early helicopter technology and coined the very term “helicopter.” Alexis was also the son of Joanna Harcourt-Smith, who was married to Timothy Leary—a relationship captured in Errol Morris’s documentary My Psychedelic Love Story. But his mother left when he was just two years old. Alexis was raised instead in Washington, D.C., by his Austrian grandmother, a sharp and self-made entrepreneur who became his greatest influence.

    Raised between two continents—with one foot in European tradition and the other in American dynamism—Alexis was shaped by the paradox of abandonment and deep mentorship. That duality has become central to his work with CEOs today, offering a perspective grounded in resilience, heritage, and the power of reinvention.

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

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

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

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alexis John d'Amecourt: https://www.linkedin.com/in/alexisdamecourt/

    Links: Mochary Method: https://www.mocharymethod.com/

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

    (0:00) Episode preview (1:39) The role and need for CEO coaching (5:08) Coaching vs. therapy for CEOs (8:08) Overcoming scaling challenges (11:57) Strategies for getting CEOs unstuck (16:11) Coaching dynamics with young CEOs (19:40) CEO misconceptions and role balance (22:33) Hiring challenges and skills of founders vs. traditional CEOs (25:02) Leadership styles: carrot vs. stick and anti selling (29:04) Managing and motivating top performers (31:20) CEO's organizational influence (33:31) Common mistakes and leadership styles of experienced CEOs (37:31) Encouraging employee peak performance (39:18) Feedback dynamics in personal and professional spheres (45:02) The role of psychopathy in scaling businesses (47:02) Ego balance for effective CEO leadership (54:32) Alexis John d'Amecourt's backstory and the power of vulnerability (59:34) Childhood trauma and its influence on founders (1:02:24) Transitioning from insecurity to vision-driven leadership (1:04:22) First principles thinking and immediate CEO improvements (1:08:17) Client profiles and contacting Alexis John d'Amecourt (1:09:19) Closing remarks

    E167: The Hardest Questions Limited Partners Ask GPs w/Stepstone’s Hunter Somerville May 27, 2025
    Show notes

    Hunter Somerville helps allocate billions of dollars across venture capital at StepStone—and he’s one of the most thoughtful LPs I’ve ever met. In this episode of How I Invest, Hunter gives us a rare look into how top institutional investors evaluate funds, pick managers, and underwrite spinouts before they even happen. We go deep on what separates the best emerging managers from the rest, how LPs think about performance before DPI, and why some GPs win repeatedly while others fade. Hunter also shares his own personal playbook—from how he manages his time to the biggest lessons he’s learned over two decades in venture. If you're raising a fund, building a firm, or just curious about how top LPs think, this one is a must-listen.

    Highlights:

    • The biggest myths about emerging managers—and what actually gets them funded
    • Why DPI and TVPI can be misleading, and how great LPs evaluate funds pre-liquidity
    • What LPs really think about spinouts—and how they prepare for them in advance
    • How to stand out as a fund manager (hint: it’s not just about performance)
    • Hunter’s framework for attribution, sourcing, and “right to win”
    • What makes an LP want to be your first check—and why StepStone often plays that role
    • Behind the scenes of StepStone’s secondaries, direct investing, and micro growth strategy
    • How Hunter structures his calendar for maximum leverage—and why he believes in being “obsessively systematized”

    -- Guest Bio: Hunter Somerville is a Partner at StepStone Group, one of the largest institutional investors in venture and growth equity. He leads investments across hundreds of funds, directs, and secondaries, and helps back many of the best emerging and established managers in the world. Hunter is known for his deep pattern recognition, clarity of thought, and a relentless work ethic that shows in everything he does.

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

    #VentureCapital #VC #Startups #OpenLP #AssetManagement

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

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Hunter Somerville:https://www.linkedin.com/in/hunter-somerville-2a24117/

    Links StepStone Group: https://www.linkedin.com/company/stepstone-group/

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

    (0:00) Episode preview (0:42) Fundraising market and LP exposure for emerging managers (2:33) Challenges and indexing venture for mid-level emerging managers (5:08) Tracking attribution, performance, and manager skill indicators (9:41) Valuation policies, game theory, and impacts on investments (12:24) Building successful investment firms and reserve strategies (18:18) Deal attribution and components of sourcing in firms (23:32) The impact of brand and right to win at various fund stages (28:42) Differentiation strategies for venture funds (32:32) Current state and evolution of StepStone's venture practice (38:11) Incorporating AI and technology in investment management (42:23) Building and evolving relationships with investment funds (44:20) Strategies for managing a busy calendar and prioritizing tasks (47:11) Mentorship, personal growth, and career reflections (51:01) Trust and reverse references in large investment transactions (54:21) Ego, selling yourself, and StepStone's ecosystem approach (55:59) Aligning incentives and culture in organizational growth (57:07) Closing remarks

    E166: $20 Billion CIO:  Why Small Cap Stocks Have Underperformed  (and why that’s unlikely to change) w/Brad Conger May 23, 2025
    Show notes

    Brad Conger has a rare view into the evolving dynamics of institutional portfolios—and how allocators can adapt. As Chief Investment Officer of Hirtle Callaghan, a $20B OCIO, Brad is responsible for investment decisions across public and private markets, and he's developed a highly nuanced view of what's working, what's broken, and where alpha really comes from. In this episode, we cover the structural decline of the small-cap index, how private markets have siphoned off the highest-quality growth companies, and why illiquidity can actually be a feature—not a bug. Brad also shares how he builds conviction in contrarian positions, what makes a great spinout manager, and why bigger private equity funds may still outperform. If you're building or managing portfolios across public and private markets, this episode is full of actionable insights.

    Highlights:

    • Why the small-cap index is now “adversely selected”
    • How private equity and venture capital have changed public markets
    • The alpha case for private markets (even at today’s prices)
    • The emotional benefit of illiquidity for investors
    • Why “alpha fetishism” leads to poor portfolio construction
    • A contrarian bet on Europe—and why it paid off
    • Why good process beats good predictions
    • Lessons from writing puts during a market selloff
    • The underrated strengths of large PE firms
    • How to underwrite spinouts—and what can go wrong
    • Brad’s “crazy trade” for his 90-year-old mother

    -- Guest Bio: Brad Conger is the Deputy Chief Investment Officer at Hirtle Callaghan, one of the largest outsourced CIO firms in the U.S., overseeing over $20 billion in assets. He is responsible for investment strategy across asset classes and geographies, leading the firm’s efforts in portfolio construction, manager selection, and tactical asset allocation. Brad previously worked at Goldman Sachs and holds degrees from Harvard and the Wharton School at the University of Pennsylvania.

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

    We’d like to thank @JuniperSquare for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #assetmanagement

    -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.

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

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Brad Conger: https://www.linkedin.com/in/brad-conger-2990884/

    -- Links: Hirtle, Callaghan & Co.: https://www.hirtlecallaghan.com/who-we-are/

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

    (0:00) Episode preview (0:45) Changes in the small cap index and implications for private equity (3:07) Quality and balance of public small cap companies in the new economic environment (7:15) The virtue of illiquidity in investments and issues with LP consultants (9:20) Asset allocation and finding quality in the small cap space (16:32) Thesis on investing in Europe and executing contrarian bets (20:26) Building conviction and the benefits of discretionary investment management (22:54) Role of corporate governance and client-manager relationships (25:45) Leeway for general partners and the European investment landscape (28:00) Navigating tariffs, strategic communication, and risk management (34:43) Bullish perspective on big private equity funds and talent retention challenges (41:06) Effective generational planning and diversifying a private equity portfolio (44:24) Preference for spinouts, their advantages, and fund scalability (52:09) Personal vs. client investment strategies and received wisdom in asset allocation (57:26) Evolutionary psychology and herd behavior in finance (58:33) Closing remarks

    E165: Hollywood Lessons on Risk, Reward, and Relationships with Alexander Ludwig May 20, 2025
    Show notes

    Alexander Ludwig is best known for his breakout roles in The Hunger Games and Vikings, but behind the scenes, he’s a multi-hyphenate: a passionate actor, a devoted entrepreneur, and the co-founder of Their Jewelry—a sustainable, recycled gold and silver brand he runs with his wife. In this episode, Alexander opens up about the brutal realities of Hollywood, the myth of overnight success, and how ego and humility have shaped his 20-year career. We also dive deep into how he's channeling his platform and resources to build a purpose-driven business that could help tackle the e-waste crisis. This conversation covers everything from surviving the actor’s feast-or-famine cycle to the importance of storytelling, Stoic philosophy, and finding peace in a hyper-competitive world.

    Highlights:

    • From Child Actor to Leading Man – Alexander reflects on the slow and painful journey from early Disney movies to The Hunger Games and Vikings
    • Hollywood as a Casino – Why acting success is like rolling dice and how persistence creates your own luck
    • The Myth of "Making It" – Even after Hunger Games, he still had to audition for everything
    • Launching Their Jewelry – The real story behind his sustainable jewelry brand with his wife Lauren
    • How E-Waste Could Power the Jewelry of the Future – Their’s plan to recycle gold from old phones to create luxury pieces
    • Compounding in the Arts – How Alexander thinks about long-term career building like an investor
    • Lessons from Stoicism – Why Ego Is the Enemy changed his life and every actor should read it
    • Child Stardom and Money – How losing money early gave him the financial discipline he relies on today
    • The Power of Entertainment – Why bringing joy to millions is no small feat Risk, Peace, and Purpose – What tech billionaires, actors, and founders all share

    -- Guest Bio: Alexander Ludwig is an award-winning actor and musician best known for his roles in The Hunger Games, Vikings, and The Covenant. He began acting at age nine and has worked in the industry for over two decades. In 2020, he co-founded Their Jewelry, a sustainable jewelry brand using 100% recycled gold and sterling silver, which he runs with his wife, Lauren Ludwig. He’s also an avid country music songwriter, extreme sports enthusiast, and passionate advocate for mission-driven entrepreneurship.

    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.

    We’d like to thank @JuniperSquare for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #assetmanagement

    -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.

    -- Stay Connected: Twitter: David Weisburd: @dweisburd Alexander Ludwig: @alexanderludwig

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alexander Ludwig: https://www.linkedin.com/in/alexander-ludwig1/

    -- Links Their Jewelry: https://theirisours.com/pages/about

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

    (0:00) Episode preview (1:28) The role of luck and timing in an acting career (3:02) Keys to success and misconceptions in Hollywood (5:20) Ludwig's journey and persistence to his first big break (9:30) Career trajectories and the intrinsic love for acting (12:20) The impact of entertainment and audience connection (15:04) Maintaining humility and gratitude in the industry (18:50) Staying in the game through longevity, passion, and dealing with ego (22:04) The interplay of hard work, smart work, luck, and humility in success (24:46) Financial prudence, living within means, and the reality of success (31:00) Long feedback loops, compounding, and contrarian bets in careers (33:16) Passion as a driver for long-term success and career focus (39:36) Achieving success through focus vs. diversification (42:01) Synergies between podcasting and fund management (43:22) Staying within your circle of competence and balancing interests (45:38) Evaluating new opportunities and Alexander Ludwig's startup, There (48:23) Differentiating in a saturated market and sustainability initiatives (54:29) Billionaires' motivations and the drive for innovation (1:01:56) Lessons from starting as a child actor and the importance of passion (1:03:29) Balancing vision with focus and Kobe Bryant's philosophy (1:05:13) Closing remarks

    E164: How I Built a Billion Dollar Company by Failing Fast w/Howard Lerman May 16, 2025
    Show notes

    Howard Lerman has founded six companies and taken one public—he's a relentless builder with an obsession for speed, innovation, and execution. Currently the Founder and CEO of Roam, Howard is reimagining what the modern workplace looks like by building the “Office of the Future,” where AI agents work alongside humans to accelerate output. In this episode, Howard joined me in How I Invest Podcast to share the frameworks and mental models behind how he leads teams, scales product-market fit, recruits S-tier engineers, and instills an almost maniacal level of urgency and creativity across the organization. We talk about what it means to enter "founder mode," why professional managers may soon be obsolete, and how cultural memes shape everything from product design to company mission. If you’re building, investing in, or simply curious about the future of work and AI-native companies—this episode is a must-listen.

    Highlights:

    • Why being a "cockroach" founder is a superpower in company survival
    • How Roam is using AI agents to automate workflows and enable 24/7 productivity
    • The "Office of the Future" and why presence matters—even virtually
    • How to spot S-tier talent (and why they might be a pain to manage)
    • Why product-market fit should be the last thing a founder gives up
    • Howard’s nightly “founder mode” ritual and obsession with speed
    • The evolution of memes and how they shape product adoption
    • The dirty secret about obsession: it’s more about the people than the mission

    --

    Guest Bio: Howard Lerman is a serial entrepreneur and currently the Founder and CEO of Roam, a startup building the "Office of the Future" by integrating AI deeply into the work experience. Previously, he was the Founder and CEO of Yext (NYSE: YEXT), which he led from startup to IPO. He is known for his strong views on founder-led companies, speed as strategy, and hiring only the best—what he calls "S-tier" talent. Howard is also an early adopter and evangelist of AI agents in the workplace.

    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.

    We’d like to thank @JuniperSquare for sponsoring this episode!

    #VentureCapital #VC #Startups #OpenLP #assetmanagement

    --

    Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.

    --

    Stay Connected: X / Twitter: David Weisburd: @dweisburd Howard Lerman: @howard

    LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Howard Lermar: https://www.linkedin.com/in/howardlerman/

    Links: Roam: https://www.linkedin.com/company/roam-hq-inc/

    --

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

    (0:00) Episode preview (1:55) Applying cockroach principles and pivoting at Yext (3:38) Company structures, founder authority, and employee empowerment (6:16) Instilling speed and operating at warp speed in a company (10:01) Delegating and recruiting top talent (17:10) Building urgency and an obsession for success in teams (21:11) Howard Lerman's formative experiences and co-founder relationships (24:12) The role of memetics and memes in business (28:31) Closing remarks

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