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 234 episodes available.

How I Invest with David Weisburd episodes:

October 27, 2025E231: Lloyd Blankfein: Keynote at AlphaSummit
David Weisburd had a chance to witness live the conversation between Jack Kokko, Founder & CEO of AlphaSense, and Lloyd Blankfein, former Chairman and CEO of Goldman Sachs, during AlphaSummit 2025 in New York City.
In this wide-ranging discussion, Jack draws out Lloyd’s reflections on his early years in Brooklyn, his path to leading Goldman Sachs, and the lessons learned from steering the firm through periods of volatility and transformation. Together they explore how leadership, risk, and technology continue to shape Wall Street—and what it takes to stay adaptable in an ever-changing world.
Highlights:
How Lloyd’s early life in Brooklyn influenced his leadership style
Lessons from being rejected by Goldman Sachs — and eventually running it
Guiding Goldman through the 2008 financial crisis and its aftermath
The value of partnership culture and communication in high-performance teams
The changing dynamics of Wall Street amid AI and automation
Balancing risk, intuition, and data in modern decision making
The evolving relationship between private and public markets
Lloyd’s reflections on adaptability, market cycles, and staying ahead of change
Guest Bio:
Lloyd Blankfein served as the Chairman and CEO of Goldman Sachs from 2006 to 2018, leading the firm through the global financial crisis and major transitions in global markets. He remains an influential voice on economic leadership, risk management, and the future of finance.
Host Bio:
Jack Kokko is the Founder and CEO of AlphaSense, a market intelligence and search platform used by financial institutions and corporations worldwide. His work focuses on advancing decision making through AI-powered information discovery.
Learn more about AlphaSense and upcoming AlphaSummit events at: alpha-sense.com.
(0:00) Introduction
(1:46) Lloyd Blankfein's Early Career and Decision-Making Reflections
(7:13) Leadership, Communication, and Managing Teams
(10:27) Evolution of Wall Street and Technological Impacts
(15:30) Automated Trading: Risks and Trust in AI
(19:23) Investment Banking Risk Control and Balancing Innovation
(21:48) Thought Experiment: Starting a New Investment Bank
(24:12) Equity Market Evolution and the Rise of Private Markets
(31:18) Big Picture Market Changes and Future Speculations
(34:25) Advice for Investors in an Evolving Market
(36:12) Closing remarks
...more
37min
October 24, 2025E230: What Great VCs Actually Do for Founders
How do you invest when it’s “too early for data”—but just right for conviction?
In this episode, I speak with Vivek Ladsariya, Managing Director at Pioneer Square Labs (PSL), about what it really takes to back founders before traction, before funding rounds, and sometimes even before incorporation.
Vivek shares how he partners with founders as a thought partner instead of a coach, why iteration trumps ideas, and how efficiency and automation have rewritten what it means to earn a Series A today. From early-stage pattern recognition to AI-driven productivity and new definitions of founder resilience, this conversation is a masterclass in what “being early” actually means in 2025
Highlights:
How investing “too early” often creates the strongest long-term alpha
Why the best investors act as thought partners, not back-seat CEOs
How ego, relentlessness, and intellectual honesty predict outlier founders
Why great ideas matter less than constant iteration and customer focus
How Series A benchmarks have shifted to roughly $7 million ARR—and what it means for founders
Why AI is the new leverage for coding, sales, and operations efficiency
How language itself has become code, allowing anyone to automate with LLMs
How PSL’s studio + fund model accelerates founders from zero to one
Why small, elite teams outperform larger organizations in the AI era
How becoming a parent sharpened Vivek’s priorities and patience as an investor
Guest Bio:
Vivek Ladsariya is a Managing Director at Pioneer Square Labs (PSL), where he leads pre-seed and seed investments out of PSL Ventures Fund II ($100 million), focusing on AI, cybersecurity, infrastructure, industrial tech, and DevOps.
Before joining PSL, he was a General Partner at SineWave Ventures and an entrepreneur behind ventures such as GameGarage and Moyyer.
His investments include Databricks, Rescale, Osaro, and Evolv Technologies (NASDAQ: EVLV). Vivek holds an MBA from Yale University and a B.E. from the University of Mumbai.
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/
Vivek Ladsariya: https://www.linkedin.com/in/vivek-ladsariya-8a828535/
Links
Pioneer Square Labs: https://www.linkedin.com/company/pioneer-square-labs/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Preview
(0:06) Evolution of programming languages and business automation
(1:05) Welcome and guest introduction
(1:16) Investing early in startups and the role of a VC
(4:17) Creating value in startups and being an effective thought partner
(7:11) Handling crises, feedback, and the role of ego in startups
(11:27) Ray Dalio's concept of believability and startup ideas
(18:22) Customer pain points and the idea maze
(21:17) Predicting entrepreneurial perseverance and evaluating founders
(24:44) Iterating startup ideas and future Series A expectations
(35:16) The impact of AI on programming and business processes
(42:56) Preparing skills for a post-AI world
(46:14) Pioneer Square Labs and thoughts on seed strapping
(50:52) Advice to a younger self and the impact of life changes on investing
(57:07) Closing remarks
...more
58min
October 22, 2025E229: Inside Industry Ventures: The $8 Billion Firm Backing 650 Venture Funds
How does an $8B venture platform turn a 650-fund network into a repeatable co-investing edge?
In this episode, Jonathan Roosevelt, Managing Director at Industry Ventures, explains how the firm evolved from a pioneer in venture secondaries into a platform combining secondaries, co-investments (directs), fund-of-funds, and tech buyout—with AUM “a little over $8B” and 25+ years in market. We break down why Series A/B/C co-investing requires a different lens than seed, how believability guides which GPs get a “stamp” for later-stage deals, and why customer calls are ground truth when underwriting mid-stage businesses. Jonathan also shares how asymmetric information and inflection points create true co-invest alpha—and when to ignore comps for N-of-1 companies.
Highlights:
$8B platform: Secondaries, co-invests, fund-of-funds, tech buyout
650-fund network: ~250 primaries, ~400 via LP secondaries
Co-invest engine: 100% sourced from seed/early GP relationships
Seed vs. mid-stage: PMF stories vs. durable unit economics
Believability lens: Repeatable process before a later-stage “stamp”
Ground truth: Independent customer diligence over CEO references
Asymmetry & inflection: Board insights at turning points drive edge
Do the unscalable: Sector depth, real customer intros, hands-on help
N-of-1 underwriting: Backcast valuation from end-state outcomes
Guest Bio:
Jonathan Roosevelt is a Managing Director at Industry Ventures, where he focuses on originating, valuing, and managing primary fund commitments, early secondary LP stakes, and direct company investments within the firm’s Direct & Partnership Holdings strategies. Previously a Venture Partner at Industry Ventures (2017), he was promoted to Managing Director in 2019; earlier, he founded and led companies, was an early employee/VP of Sales at SoFi, and invested as an angel in Fitbit. He holds an MBA and BA from Harvard.
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/
Jonathan Roosevelt: https://www.linkedin.com/in/jroosevelt/
Links
Industry Ventures: https://www.industryventures.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Preview
(0:04) Customer feedback's impact on investments
(1:03) Industry Ventures' co-investment strategy
(3:44) Co-investment opportunity lifecycle
(7:19) Assessing investment manager credibility and diligence
(17:14) Identifying exciting co-investment opportunities
(19:47) Triangulating information for investment decisions
(23:04) Customer enthusiasm in the investment process
(27:16) Relationship significance in investment decisions
(29:34) Operator vs investor perspectives in venture capital
(34:01) Risk management for seed stage investments
(37:10) Competing as an emerging manager in venture capital
(38:43) Valuation strategies for new venture capitalists
(41:18) Closing remarks
...more
41min
October 20, 2025E228: Balaji Srinivasan: “The Dollar Is Already Dead” and What Comes Next
What if the U.S. dollar’s dominance has already ended—and we’re just living through the lag?
In this episode, I sit down with Balaji Srinivasan, one of the most original thinkers in technology and finance, to unpack his boldest prediction yet: the death of the dollar and the rise of a digital, decentralized global economy.
Balaji explains how inflation, weaponized finance, and technological sovereignty are accelerating a massive shift away from traditional monetary systems—and why crypto, AI, and network states could define the next reserve paradigm.
We go deep into why he believes the internet will replace the nation-state, how founders can build parallel institutions from scratch, and why opting out—not lobbying—is the only path forward.
This is not a doomsday take. It’s a blueprint for builders who believe the future is already here.
Highlights:
The Network State: How online communities will evolve into sovereign cities.
From Crypto to Cities: Why blockchain can fund and govern real-world nations.
The Balaji Fund: Backed by Brian Armstrong, Marc Andreessen, and David Sachs—investing in “techno-radicals.”
Replacing Broken Systems: How founders can build alternatives to failing institutions like education, healthcare, and media.
Lessons from China: What the U.S. can learn from China's manufacturing and infrastructure speed.
India’s Decade: Why Balaji believes India is becoming the new global tech engine.
High-Risk Seed: Why his investment strategy targets contrarian, world-changing founders.
From Bitcoin to Benchling: Inside Balaji’s personal portfolio and his “index the outliers” approach.
The Frontier Mindset: How today’s founders can reclaim the spirit of Silicon Valley’s pioneers.
Opt-in Capitalism: Why the future of governance will be voluntary, networked, and global.
Guest Bio:
Balaji S. Srinivasan (born May 24, 1980) is an American entrepreneur, investor and author. He co-founded genetic-testing firm Counsyl and led cryptocurrency company Earn.com before becoming first CTO of Coinbase and a General Partner at Andreessen Horowitz. He holds a BS, MS and PhD in Electrical Engineering and an MS in Chemical Engineering from Stanford 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/
Balaji Srinivasan: https://www.linkedin.com/in/balajissrinivasan/?originalSubdomain=sg
Links
Balaji Srinivasan: https://en.wikipedia.org/wiki/Balaji_Srinivasan
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Preview
(3:24) Steps to create a new country and the concept of network states
(7:18) The Internet's transformative impact and decentralized countries
(10:41) Crypto tribalism and Bitcoin's economic role
(14:13) Cryptocurrencies as emerging digital nations
(17:42) Government inefficiencies and the future of democracy with digital currencies
(21:27) The evolution of capitalism and democracy
(23:37) The role of DAOs in digital governance and network states
(31:09) Utilizing crypto for crowdfunding and real estate
(35:01) Introduction to the Balaji Fund and investment strategies
(38:15) Technological solutions for societal problems
(41:16) Profit maximization aligned with values and addressing Baumol's cost disease
(45:03) Regulatory challenges in healthcare and childcare
(47:34) DAOs' potential in real estate and community formation
(51:20) Translating digital processes into physical communities
(54:16) Balaji Fund's investor alignment and societal impact
(1:02:21) Government, technology, and cost dynamics
(1:06:20) Political pressures and pension paradoxes in investments
(1:09:15) Diagnosing inefficiencies in real estate and construction
(1:11:17) China's strategic advantages and US challenges
(1:15:17) US-China strategies and the American dynamism dilemma
(1:25:26) US political and social divides, government failures, and potential solutions
(1:27:49) Competing with traditional institutions through innovation
(1:30:20) Addressing societal issues with technology and portfolio construction
(1:32:37) Investing in high-potential founders and the rise of Indian tech talent
(1:35:28) Global capital impact of crypto and cybersecurity importance
(1:37:14) Balaji's investment strategy and notable successes
(1:41:33) Closing remarks
...more
2h 51min
October 17, 2025E227: The Future of Venture: Ryan Hoover on Productizing VC
What happens when one of tech’s best community builders turns his playbook on venture capital itself?
Ryan Hoover — the founder of Product Hunt and Investor at Weekend Fund — joins me to unpack how he’s reinventing early-stage investing. From building one of the internet’s biggest startup communities to managing a fund with 360+ LPs, Ryan shares the hard-won lessons on productizing VC, scaling systems as an introvert, and finding founders who hold true “earned secrets.”
We dive into his journey from launching Product Hunt to building Weekend Fund’s third vehicle, how he thinks about portfolio construction, why weird ideas often win, and what it really takes to back the next generation of breakout founders.
Whether you’re a founder, operator, or investor — this episode is packed with insights on scaling yourself, spotting alpha before it’s obvious, and turning community into competitive advantage.
Highlights:
How Ryan built Product Hunt into a launchpad for over 100,000 startups.
The story behind raising from 360+ LPs — and why one investor literally became a monk.
Why Weekend Fund prefers staying small to keep conviction high.
The psychology of “weird” investing — and why strange ideas often outperform.
How Ryan productized LP intros and scaled value-add through software.
Why the best investors give without expecting anything in return
How to build a scout network that multiplies your reach without adding complexity.
The key traits of elite super connectors (and why Ryan doesn’t see himself as one).
Why founders with “earned secrets” beat consensus every time.
Ryan’s one piece of advice to his younger self before launching his first fund.
Guest Bio:
Ryan Hoover is the Founder and Investor at Weekend Fund, an early-stage venture capital firm investing in founders with earned secrets—deep insights derived from firsthand experience.
Weekend Fund has raised three funds and invested in over 100 startups globally, including Deel, Replicate, and Rally, backed by a diverse community of more than 360 limited partners.
Before founding Weekend Fund, Ryan founded Product Hunt, the platform that helped launch tens of thousands of startups and shaped how the tech world discovers new products. He has since focused full-time on building a new venture model centered around community, transparency, and product thinking.
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
Ryan Hoover: @rrhoover
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Ryan Hoover: https://www.linkedin.com/in/ryanrhoover/
Links
Weekend Fund: https://www.weekend.fund/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Preview
(0:14) Secrets, lived experience, and productizing LP intros
(1:51) Fundraising challenges and LP base management
(3:07) Downsides and expectations with 360 LPs
(6:31) Venture capital as a product and Weekend Build experiment
(9:10) Rolodexer success and becoming an elite super connector
(14:18) Using value add to win deals and portfolio construction strategies
(22:10) Ryan Hoover's LP activities, SPVs, and strategic investments
(26:11) Scaling productivity and weekend partners program
(29:17) Transparency and investing in non-consensus companies
(37:42) Information diet, advice to younger self, and early strategies
(42:00) Best product importance vs. portfolio construction and market changes
(43:32) Managing a large portfolio and scaling support with tools
(44:14) Closing remarks
...more
45min
October 15, 2025E226: How Franklin Templeton Built a $1.6 Trillion Business Through Partnerships
Why are Institutional Investors betting big on Private Markets?
Franklin Templeton oversees more than $1.6 trillion in assets, with over $260 billion dedicated to private markets. But what’s driving this massive shift — and how are the world’s largest allocators navigating liquidity, valuations, and the next era of private credit?
In this episode, I speak with John Ivanac, Head of U.S. Institutional Alternatives at Franklin Templeton, to uncover how the firm is positioning itself for the next decade of alternative investments. We explore the evolution of private markets post-GFC, the consolidation wave among asset owners, and why liquidity, governance, and strategy selection are becoming more critical than ever.
John also shares his perspective on Franklin’s acquisition strategy, how they integrate firms like Lexington Partners and Benefit Street Partners, and what it truly means to be a “trusted partner” to LPs in an increasingly complex market.
Highlights:
Structural Shifts: How regulation and capital formation reshaped private markets post-GFC
Private Credit Boom: Why a $3.5T market could expand 10x in the next decade
Secondaries Surge: Inside Franklin’s bet on Lexington Partners and the maturing PE ecosystem
LP Consolidation: Why institutional allocators are backing fewer but deeper partnerships
Holistic Partnerships: How Franklin Templeton redefines client alignment beyond products
Digital Assets Strategy: Why the firm built a 60-person blockchain and crypto investment team
Retail & Institutional Synergy: The future of democratizing alternatives responsibly
Culture of Long-Termism: How generational leadership drives Franklin’s innovation mindset
Guest Bio:
John Ivanac is the Head of U.S. Institutional Alternatives at Franklin Templeton, where he focuses on expanding and managing the firm’s suite of Alternative Investment Solutions for institutional investors.
John brings over 20 years of experience in the alternatives space, having previously served as Managing Director, Head of U.S. Consultant Relations at Partners Group and Global Head of Alternatives at BlackRock. He has also held senior leadership roles at The TCW Group, Scoggin Capital, and Barclays.
He holds a J.D. from St. John’s University School of Law and a B.A. from Rutgers University, bringing a deep understanding of both the structural and human dynamics driving today’s institutional capital markets.
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/
John Ivanac: https://www.linkedin.com/in/johnivanac/
Links
Franklin Templeton: https://www.franklintempletonglobal.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Preview
(0:59) Introduction to Franklin Templeton and private investment strategies
(2:51) Drivers and opportunities in private market growth
(7:15) Institutional investment and volatility in alternatives
(14:44) Future outlook and building a significant portfolio
(19:02) Acquisitions, strategic focus, and consolidation trends
(21:51) Partnering and aligning with asset managers
(25:46) Culture and long-term vision in expanding portfolios
(28:46) Franklin Templeton's benefits for LPs and manager consolidation
(35:58) Digital assets and balancing investor types
(39:40) Retail market practices and investor education
(45:38) Career advice and patience in investment
(47:53) Building credibility, trust, and partnership roles
(50:59) Addressing short termism in public markets
(51:31) Closing remarks
...more
52min
October 13, 2025E225: Inside the $324B Playbook: How Hightower Is Reshaping Wealth Management
Can a $324.3 billion wealth manager reinvent how high-net-worth investors access private markets?
In this episode, I speak with Robert Picard, Head of Alternative Investments at Hightower Advisors, who is leading one of the industry’s most ambitious expansions into private markets. We discuss how Hightower is bringing institutional-grade research, access, and due diligence to individual investors, what the NEPC acquisition means for its alternatives platform, and how technology and AI are reshaping the way portfolios are built.
Robert also shares lessons from more than 35 years of building multi-billion-dollar alternative platforms atThe Carlyle Group/Rock Creek, Optima Fund Management, RBC Capital Markets and State Street/InfraHedge, and explains why the future of wealth management will look more like an endowment model than ever before.
Highlights:
How Hightower is bridging institutional research with private-client portfolios
The strategic rationale behind acquiring NEPC and its impact on Hightower’s platform
Why private markets are still under-owned among high-net-worth investors
The “democratization and miniaturization” of private markets and what that means for access
Robert’s framework for allocating 10–30% of portfolios into private assets
Why illiquidity can actually be your ally during market downturns
How AI and technology will transform investment diligence and portfolio construction
The evolution of independent wealth managers competing with Wall Street wirehouses
Why maintaining curiosity, networks, and fun are keys to a 35-year investing career
Guest Bio:
Robert Picard is the Head of Alternative Investments at Hightower Advisors, where he leads the firm’s alternative investment platform and oversees research, due diligence, and portfolio design. He previously held senior roles building multi-billion-dollar alternative platforms at The Carlyle Group / Rock Creek, Optima Fund Management, RBC Capital Markets, and State Street / InfraHedge, and served as Head of Alternatives at First Republic Private Wealth Management.
Robert has over 35 years of experience in global investing, with a background in equity derivatives, structured products, and private markets. He is widely regarded for his insights on the convergence of institutional and private wealth investing
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/
Robert Picard: https://www.linkedin.com/in/robpicard/
Links
Hightower Advisors: https://hightoweradvisors.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Preview
(1:07) Hightower Advisors and NEPC Acquisition Strategy
(2:33) NEPC's Research Benefits and Portfolio Differences
(5:55) Democratization of Private Markets for Individuals
(8:56) Private Asset Allocation Strategies
(13:35) Illiquidity Benefits and Market Downturn Preparation
(17:34) Long-Term Cybersecurity and AI Investment Strategies
(23:06) The 2030 Asset Management Outlook
(24:26) AI in Private Market Research and Growth Projections
(28:40) Life Sciences Investment Opportunities
(30:18) Independent Wealth Managers vs. Wirehouses
(33:20) Evolving Role of Family Offices
(36:00) Diversification in Private Markets and Future Trends
(42:05) Technological Advancements in Private Markets
(45:02) Managing Multiple Advisor Practices and Efficiency with AI
(49:33) Career Advice for Young Professionals
(51:11) Work-Life Balance and Industry Transformations
(51:58) Closing Remarks and Future Podcast Plans
(52:09) Closing remarks
...more
53min
October 10, 2025E224: Ex-CIO of Northern Trust: The Next Decade Belongs to Bonds, Not Stocks
If “fixed income is broken,” what are investors actually missing—and how should they rebuild the 40% to protect and compound through drawdowns?
In this episode, I speak with Thomas E. Swaney II, former Chief Investment Officer of Global Fixed Income at Northern Trust Asset Management, who oversaw more than $600 billion across global fixed income. Thomas explains why traditional bond allocations fail when it matters most, how to separate duration from credit risk, and how to use notional leverage to target true diversification without sacrificing liquidity. We explore the structural flaws in 60/40, how to design a fixed income portfolio that actually offsets equity drawdowns, and why the future of bond investing depends on better risk budgeting—not higher yield.
Highlights:
Fixed Income Is Broken: Why most bond portfolios don’t diversify when equities fall
Rebuilding the 40%: Duration vs. credit and managing correlation through regimes
Notional Leverage: Using treasury futures and IG CDX to build volatility with quality
Risk Parity Framework: Allocating by contribution to risk, not nominal dollars
Rebalancing Alpha: Liquidity and negative correlation as the real edge
Curve Positioning: Why the belly of the curve often outperforms the long end
Convexity Mismatch: Public vs. private assets and the lagged rebound effect
Inflation Regimes: How correlation flips and when to incorporate TIPS
Leadership & Culture: Lessons from Ellington and Northern Trust on process and debate
The Next Decade: Bonds are relevant again—if built for resilience
Guest Bio:
Thomas E. Swaney II is the former Chief Investment Officer of Global Fixed Income at Northern Trust Asset Management, where he had broad oversight of the $600+ billion fixed income platform, spanning business management, portfolio management, and strategy. As CIO, he chaired the Fixed Income Strategy Committee, guiding macroeconomic themes, risk budgeting, and portfolio construction across all fixed-income portfolios. He also served on Northern Trust’s Investment Committee and Executive Group within Asset Management.
Prior to Northern Trust, Thomas held senior executive and portfolio management roles at J.P. Morgan Asset Management, Morgan Stanley Investment Management, OFI Global Asset Management, and Ellington Management Group. He holds a B.B.A. and M.B.A. with a concentration in corporate financial analysis, as well as an M.Sc. in Finance from the Kelley School of Business at Indiana University, and has more than 26 years of investment experience.
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/
Thomas E. Swaney II: https://www.linkedin.com/in/swaneycio/
Links
Factor Two Capital Management: https://brand.site/factortwocapital
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Preview
(0:48) Thomas Swaney's career and Miller Anderson's open debate culture
(5:00) Challenges and impacts of open dialogue culture in investment firms
(6:42) Education systems and their influence on investment thinking
(7:47) Leadership vs. Investment Skills
(9:40) Shifting Northern Trust's focus and lessons from Ellington
(18:45) The role and strategies for fixed income in a diversified portfolio
(23:35) Understanding market downturns and Bridgewater's equilibrium approach
(27:24) Decomposing and maximizing efficiency in bond portfolios
(33:56) Challenges and strategies with private assets in portfolios
(38:40) The impact and use of leverage in investment portfolios
(42:43) Introduction to Factor Two Capital Management
(44:38) Exploring the relationship between volatility and expected values
(49:16) Fed independence and market reactions to policy changes
(51:35) Misconceptions about monetary policy and economic impact
(53:04) Future outlook on fixed income versus equities and prediction markets
(55:24) Closing remarks
...more
56min
October 08, 2025E223: The Art of Capital Allocation at $86 Billion Scale
What are the real playbooks behind managing an $86B alternative asset platform—and where do the next decade’s returns actually come from?
In this episode, I sit down with Payton Brooks, Managing Director on Future Standard’s Primary Investments team, to unpack the operating system behind a multi-strategy LP: how a combined platform serves both institutions and the wealth channel, why mid-market private equity still offers the best shot at alpha, and how evergreen structures can reduce cash drag while preserving optionality. We cover sourcing (spinouts, emerging managers), what great GPs do in downturns, the co-invest / secondaries / credit toolkit, and the partnership behaviors that earn re-ups across multiple fund cycles.
Highlights:
Future Standard under the FS + Portfolio Advisors merger with ~$86B AUM
How wealth clients access institutional alternatives via structured vehicles
Mid-market outperformance vs. large-cap PE
Operating depth and specialization as scale drivers
Evergreen strategies reducing cash drag
Anchor LPs as credibility signals
Partnership transparency as LP/GP discipline
Co-invest, secondaries & credit augmenting optionality
Patience, credibility & compounding relationships
Guest Bio:
Payton Brooks is a Managing Director on Future Standard’s Primary Investments team, focusing on manager selection and portfolio construction across the private-equity landscape. He joined the firm in 2014, and holds a B.A. from Southern Virginia University and an MBA from the Yale School of Management. Future Standard is a global alternatives platform investing across private equity, credit, and real estate, serving both institutional and private-wealth clients; the firm rebranded from FS Investments in July 2025 following its combination with Portfolio Advisors in June 2023.
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/
Payton Brooks: https://www.linkedin.com/in/paytontbrooks/
Links
Future Standards: https://www.futurestandard.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(0:44) Client base and portfolio construction
(1:40) Differences between high net worth individuals and pension funds
(3:02) Access for high net worth investors to asset classes
(4:05) Characteristics of successful private equity funds and large cap buyouts
(9:21) Evaluating middle market managers and building relationships
(16:40) Utilizing secondaries, co-investments, and internal team structure
(19:01) Traits of elite superstar GPs and repeatable value creation
(23:22) Decision-making process and portfolio construction within the buyout fund
(28:39) Pension fund investment in Evergreen Fund mechanics and benefits
(34:14) Evergreen Fund strategy, market impact, and comparison to drawdown funds
(41:32) Challenges and strategies for emerging managers
(44:02) Securing anchor investors and LP decision-making
(47:58) Importance of time optionality in fund investments
(51:08) Balancing early and late fund investments
(53:20) Career reflections and advice to younger self
(55:23) Enhancing investment knowledge and leveraging partners for insights
(57:06) Closing remarks
...more
58min
October 06, 2025E222: Why 90% of Managers Fail Before Fund 3
Why do ~90% of first-time managers fail before Fund II/III—and what separates durable fund builders from good investors?
In this episode, I unpack that question with Conrad Shang, Founder & Managing Partner at Ensemble VC. We examine why being a great investor is necessary but not sufficient to be a great fund manager, how to build for durability across cycles, and the partnership practices that earn long-term LP trust. Conrad shares lessons from UTIMCO, Norwest, and Bain Capital Ventures; why sometimes the hardest move is sitting out frothy markets; and how Ensemble uses a team-first lens and internal data products to focus time on the few opportunities that matter. We also discuss defense tech’s shift from “taboo” to mainstream, and why communication cadence and transparency determine who survives the first four to five years—when most managers wash out.
Highlights:
Investor ≠ fund manager: portfolio construction, firm-building, and 10–12 year horizons matter as much as deal picking.
Durability over cycles: sometimes the right move is doing zero deals for ~12 months to avoid overpaying.
Power laws require survival: stay in the game long enough to catch the outliers; size and pacing are part of edge.
LPs as partners, not capital: trust, warm introductions (“trust by proxy”), and over-communication—without “crying wolf.”
Team > solo founder myth: first hires and sequencing reveal how companies will actually be built.
Defense tech arc: from taboo to obvious—examples include ICON (3D-printed homes), Saronic, and Manifest (ex-Palantir).
Data-driven firm design: internal platform (“Unity”) reallocates time from low-yield first meetings to high-conviction winning.
Pilot fund outcomes: Ensemble’s Fund I (pilot) marked ~12×; scaling the model required re-architecting org + software.
Guest Bio:
Conrad Shang is Founder & Managing Partner at Ensemble VC. Previously, he led/managed venture investing at UTIMCO and invested at Norwest Venture Partners and Bain Capital Ventures; earlier he was a consultant at Bain & Company. He’s a Kauffman Fellow and has sat on both the GP and LP sides of the table—experience that informs Ensemble’s product- and data-driven approach to firm building.
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/
Conrad Shang: https://www.linkedin.com/in/conradshang/
Links
Ensemble VC: https://www.ensemble.vc/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(1:25) Fund management skills beyond investing
(2:06) Time horizons in investments vs. fund management
(4:24) Navigating economic cycles and long-term strategy
(7:06) Venture investing and the power law paradox
(8:24) Emerging challenges for new fund managers
(10:48) Investment timing in defense tech and 3D printing
(11:44) Team dynamics and talent as success predictors
(14:57) Trust-building lessons from UTIMCO
(19:04) The critical role of trust in LP-GP dynamics
(21:21) Treating LPs as partners and the educational aspect
(23:50) Mutual benefits of LP-GP collaboration
(29:55) Fostering trusted long-term LP relationships
(33:46) Transparency and communication with LPs
(36:19) Investment theses and relationship importance
(41:58) Insights from LP experience at UTIMCO
(46:41) Practices of successful GPs
(51:58) Relationship alpha and its impact on venture success
(52:32) Ensemble's Fund One and its approach
(54:16) Data and software in Ensemble's investment strategy
(57:06) Data-driven investment case studies
(1:00:37) Ensemble's Unity platform and efficiency tools
(1:03:04) Using data for informed investment decisions
(1:06:06) Team cohesion and its importance
(1:08:14) Closing remarks
...more
1h 9min

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