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Swimming with Allocators

Earnest Sweat, Alexa Binns

Swimming with Allocators dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. In each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. Follow along and subscribe at swimmingwithallocators.com. See you later, Allocator!

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  • 24 episodes
  • fortnightly
  • Avg 46 min
  • English

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  • Wednesday · 41 min

    What LPs Really Want From Venture Funds

    This week on Swimming with Allocators, Rachel Kloepfer shares her journey from growing up on a farm near Seattle and working as an investigative crime reporter to becoming an institutional allocator at Lenora Capital, the private investments arm of Brighton Jones. She explains how journalism skills like asking sharp, unscripted questions, digging through public records (FOIA), and backchanneling translate directly into better fund due diligence and manager selection. Rachel breaks down how she evaluates mega funds versus emerging managers, the importance of sourcing edge, media strategy, and succession planning, and why DPI and realistic timelines matter for families versus endowments. She also coaches on when wealthy individuals should use diversified vehicles like Lenora versus doing direct deals or backing emerging GPs themselves. Finally, Rachel looks ahead to the “media wars” in venture, predicting that owned media, storytelling, and entertainment-level content will become central to how firms attract founders, talent, and LPs, and how they control their narrative in an increasingly volatile market. Also, don’t miss Sidley’s Michael Podolny, who explains how he helps startups navigate founder separations and complex AI/data deals, and how AI tools are transforming his legal workflow. Highlights from this week’s conversation include: Rachel’s Origin Story and Farm-to-Finance Journey (0:04) Parallels Between Journalism and Investing Question from Alexa (3:10) Using Public Records and FOIA Tools to Backchannel and Check Narratives (8:37) What Lenora Capital Is and How It Fits Inside Brighton Jones Family Office (10:54) Benchmarking Top-Tier Funds, DPI Focus, and Limits of Quantitative Metrics (16:28) AI, Data, and How Generative Tools Are Changing Legal Workflows at Sidley (20:38) Returning to LP Interview and Framing Talent at Mega Funds vs Emerging GPs (22:43) How Rachel Assesses Talent, Network, and Founder Pull Across the Barbell (23:16) Why Succession Planning at Major VC Firms Can Be a Dealbreaker for LPs (25:53) Coaching Clients on Direct Deals vs Pooled Vehicles (33:13) Future of Media Wars, Owned Media, and Entertainmentification of Venture (36:09) Parting Thoughts and Episode Wrap-Up (39:06) Lenora Capital was created in partnership with a group of family offices to deliver holistic private market solutions for deploying capital and providing comprehensive advisory services. The platform is augmented by partners with the expertise to enhance Lenora Capital’s value proposition. We offer select family offices and RIAs tailored investment opportunities, personalized advisory services, and exclusive access to private markets, specifically, to opportunities not easily accessible to individual investors. Learn more at www.lenoracapital.com. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • September 9 · 49 min

    Beyond Consensus: Where Europe’s Next Great VCs Are Emerging

    This week on Swimming with Allocators, Henrik Reimavuo traces his path from teen volunteer at Slush to LP and co-founder of Firm, a fund of funds backing next-gen venture managers. He explains how Slush exposed him to the power of narrative in capital flows, what he learned from legendary investors with low ego and high conviction, and how his stints at Nokia’s NGP and a Swiss insurer shaped his view of incentives. The conversation dives into why Europe’s VC gap with the US is more about quality and misallocation than raw capital, the outsized role of government and corporates, and today’s hot themes like European resilience, defense, and cybersecurity. A key takeaway: incentives and authentic community-building matter more than ever, and the future of European venture will be defined by specialized, culturally rooted managers rather than broad, state-driven capital programs. Also, Sidley’s Michael Podolny shares how he’s increasingly helping startups navigate early founder breakups and complex AI/data licensing deals, and how deeply integrated AI tools have transformed his legal workflow without replacing his core judgment and client relationships. Highlights from this week’s conversation include: Henrik’s Path From Slush Volunteer to Venture (0:14) Scale of Slush and First Lessons on How Capital Flows (1:53) Traits of Great Investors and Lessons from Industry Legends (4:51) Direct Investing Roles at NGP, Tempo Driven Fund, and Swiss Insurer (7:57) Swiss Wealth Culture, Capital Preservation, and Slow Venture Adoption (13:04) How State-Backed Capital Shapes Incentives and Misallocation in Europe (14:50) Defining Next Gen Managers Operating at the Esoteric Edge (18:47) IRL Community Building, Niche Founder Networks, and New Funds (26:43) Frame Overview, Sub 100 Million Focus, and Firm Building Philosophy (30:36) European Focus, Cultural Proximity, and European Links for US Managers (33:34) Why LPs Want More Direct Deals and Power Law Concentration (38:19) Future Role of Fund of Funds as Filters and Strategic Partners (41:32) Emerging Manager Map and VC Fund Benchmarking Tool Insights (43:31) Radical Transparency, LP Behavior, and Just Saying No Clearly (45:27) Closing Thoughts and Episode Wrap-Up (47:02) FIRM Capital is a next-generation fund-of-funds backing next-gen venture managers “defined by a clear strategic edge, formed by firsthand operating and investing experience.” The firm looks for managers who “operate at the esoteric edge, invest at inception, build belief through proximity,” and it aims to become the first call on the cap table — writing up to $10 million as a manager’s first institutional check into sub-$100M funds across Europe and the US, where it looks for a strong European link. FIRM runs a deliberately concentrated portfolio where every manager has to matter, offers its LPs direct, fee-free co-investment alongside its portfolio GPs, and publishes open resources for the ecosystem including its Emerging Manager Market Map and Venture Fund Performance Benchmarks. Learn more at wearefirm.com. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • August 26 · 43 min

    Inside the LP Mindset: What Makes a Venture Manager Stand Out

    This week on Swimming with Allocators, allocator Michael Wooten shares his journey from early fascination with investing to managing capital across multiple family offices and building a venture program in Silicon Valley. He explains how family offices differ based on principals’ goals and control, why venture and growth equity should be treated as distinct risk buckets, and what he learned starting a venture effort from scratch. The conversation also covers trends in secondaries and SPVs, the challenges of liquidity and cyclicality in venture portfolios, the merits of generalist versus specialist strategies, and how LPs really diligence fund managers, emphasizing curiosity, communication, alignment, and not working with people who are difficult or misaligned. Also, Sidley’s Michael Poldony explains how secondaries and tender offers have become a standard step on the path to IPOs, how strategic investors and secondary-only funds are reshaping late-stage liquidity, and why careful structuring, valuation awareness, and legal guidance are critical for both companies and allocators participating in these transactions. Highlights from this week’s conversation include: Michael’s Early Money Story and Buffett Inspiration (0:21) First Atlanta Family Office Role and Exposure to Alternatives (4:57) Control Dynamics at a Silicon Valley Family Office (7:28) Lessons From Building a Venture Program During 2020 (10:27) Curiosity, Tenacity, and Fit for a Career in Venture (13:33) Storytelling, Execution, and Being Differentiated but Underwritable (16:58) Secondaries as a Standard Step on the IPO Journey (21:59) Who Is Buying Growth Secondaries and Related Legal Considerations (24:49) Blended Valuations in Combined Primary and Secondary Rounds (27:56) Reconciling Capital-Efficient Startups With Mega AI Rounds (29:38) How Allocators Should Think About Venture’s Role and Cyclicality (31:39) Pet Peeves About Manager Behavior and Treatment of LPs (37:16) Running Snowball Adventures SPVs and Ensuring LP Alignment (39:25) Final Thoughts and Episode Wrap-Up (41:07) Michael Wooten is the Founding Partner of Snowball Adventures, a private angel syndicate to invest in early-stage companies with adventurous founders tackling big, bold problems. With over fourteen years of experience in alternative investments, asset management, and entrepreneurship, I am a passionate and driven investor. I leverage my expertise and education to invest in and support innovative and impactful startups, such as Boardy, Function Health (via Getlabs acq.), CalypsoAI (acquired), Spoak Décor, Fellow Health, Nota AI, Solace Health, and Chooch AI. Motivated by insatiable curiosity, I bring a diverse perspective and a collaborative approach to my work and I enjoy continuously learning from and empowering others. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • August 12 · 48 min

    Finding Alpha Before Consensus: Data, Judgment, and Early-Stage Venture

    This week on Swimming with Allocators, Earnest and Alexa welcome Kelli Fontaine of Cendana Capital, as she traces her path from journalism to data-driven venture investing and explains how her obsession with finding the truth shapes her work as an LP. She breaks down how Cendana builds and uses its data systems, why early-stage power laws and portfolio construction matter more than headline TVPIs, and how she balances hard data with judgment about GPs. Kelli challenges the idea that pre-seed always outperforms seed, shares why fund I and II managers are uniquely compelling, and explores trends like concentrated portfolios, deep tech, defense tech, AI-native founders, and secondaries. Also, Sidley emerging companies lawyer Michael Podolny explains that rapid growth and complexity in AI-driven startups are driving demand for globally sophisticated legal advice from day one, with a particular focus on repeat founders, control, and tax optimization through QSBS planning. Highlights from this week’s conversation include: Kelli’s Journalism Roots and Early Fascination with Data (0:29) Moving from Finance to Tech and Startups at RPX (2:42) Building Data Infrastructure and Dashboards at Sandana (7:07) What People Mean by the “Sandana Model” and Relationship Focus (10:31) Why Funds Ones and Twos Are Special and How GPs Evolve Over Time (15:09) Why Late-Stage AI and Mega Rounds Don’t Replace Early Stage Alpha (19:30) Sponsor Segment: Sidley’s Work With AI and Sophisticated Startups (21:16) Tax Optimization and QSBS Considerations for Founders and Investors (24:49) KPIs That Matter: Revenue, Customer Quality, and Go-To-Market (28:40) How Changing Graduation Rates Affect Fund One and Fund Two Diligence (30:24) How to Think About Founder Secondaries vs GP Secondaries (34:54) Portfolio Management, Write-Offs, and the Real Role of Acqui-Hires (37:13) Treating Venture Like Public and Private Equity Segments (Small vs Mega) (40:05) Frustrations With AI Hype, FOMO, and Public Perception of Tech (43:50) Closing Remarks and Reflections on Macro Conversation (45:39) Cendana Capital is a venture fund-of-funds focused on investing in seed-stage venture capital firms and partnering with managers at the earliest stages of company formation. The firm is one of the most active LPs dedicated to the seed ecosystem, with a focus on identifying and supporting differentiated early-stage venture managers. Learn more at www.cendanacapital.com. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • July 29 · 53 min

    AI, SaaS and the Next Private Markets Shakeout

    This week on Swimming with Allocators, returning guest Chris Schelling of Aksia joins Earnest Sweat and Alexa Binns to unpack how AI, private markets, and the wealth channel are evolving. They discuss where AI may already be in bubble territory, how it’s reshaping SaaS, services, and investment processes (including AI “agents” on investment committees), and why some SaaS and low-value information services are most at risk. Chris explains Aksia research-driven approach across private equity, private credit, real assets, and hedge funds, and shares why he’s skeptical of layered SPV “sandwiches” and headline-driven fear around private credit. The conversation explores the democratization of alternatives for wealthy clients, the role of content as a strategic edge for allocators, challenges in structuring venture access products, and why early-stage technical venture and quantum computing are compelling. Chris closes with advice for newer professionals: in a world of AI tools, differentiated relationships, networks, and deep domain expertise matter more than ever. Also, Nick Cassin explains how Sidley’s secondary practice spans multiple asset classes and deal types, highlights the growing role of secondaries in venture (including GP‑leds and LP trades), and shares how Sidley’s breadth, commercial mindset, and experience help clients navigate complex liquidity and continuation vehicle structures. Highlights from this week’s conversation include: Chris Schelling Returns & Aksia Career Move (0:13) Why To Be Skeptical of AI Valuations & Bubbles (2:26) How AI Is Reshaping SaaS, Services, and Credit (6:48) Using AI for Diligence, Memos, and Investment Committees (11:29) Behavioral Coaching and Training Analysts With AI (15:06) SPVs, SPV “Sandwiches,” and 2008-Style Layering Risk (19:58) Checklist Ideas for Evaluating SPVs and Access Claims (29:24) How Mega RIAs Are Building Private Markets Platforms (36:38) Strategic vs Tactical Allocations Across Private Markets (41:38) Product Diversity Needed Across RIAs and Client Segments (44:08) Segmenting Venture: Seed, Growth, and Late Stage Dynamics (47:52) Crystal Ball on Venture, Deep Tech, and Quantum Computing (49:39) Skills for Young Investors: Networks, Relationships, and Domain Expertise (54:22) Where To Read Chris’s Research and Writing (55:13) Aksia is a global private markets investment advisory and research platform with deep expertise across private equity, private credit, real assets, and hedge funds. The firm advises institutional investors globally and also manages discretionary capital through customized funds-of-one, co-investment vehicles, fund-of-funds, and wealth-oriented private markets solutions. Aksia is known for its open architecture model, broad GP relationships, and rigorous diligence culture across alternative assets. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • July 15 · 54 min

    How Canada Can Become North America’s Trusted Innovation Hub

    This week on Swimming with Allocators, Earnest and Alexa welcome Senia Rapisarda of HarbourVest, who walks through her journey from Italy and Wall Street to leading venture and growth efforts in Canada, first at BDC and now as a major LP. She explains how Canada’s venture ecosystem has evolved, the creation and impact of the Venture Capital Action Plan, and why innovation capital is critical to national sovereignty. The conversation covers what makes great Canadian fund managers (curiosity, humility, team-building, and agility), how emerging managers should approach institutional LPs and avoid basic fund management mistakes, and why valuation discipline and non-greedy founders matter in down cycles. Also, Nick Cassin explains how continuation vehicles (CVs) give LPs a choice between liquidity and extended exposure to high-conviction assets when a fund’s term and capital are running out. He describes how the market has broadened to more types of investors and fund sizes, and outlines the conflict-of-interest controls that make these GP-led secondaries work. Highlights from this week’s conversation include: Senia’s Background, Global Career, and Move to Canada (0:21) Moving to HarbourVest and Designing Canada Growth Strategy (4:00) Canada’s “Perfect Storm” and Agriculture vs Geology Metaphor for Venture (5:42) What Canada Needs to Fully Capture Innovation Opportunity (8:04) How US Allocators Should Approach Canada and Diversification Benefits (11:21) Expectations of Emerging GPs and Importance of Fund Management Basics (17:59) When Continuation Vehicles Make Sense for Venture (21:39) Trends in New Money Capital and Expansion of CV Market (23:40) Managing Conflicts of Interest in GP-Led Continuation Vehicles (26:29) LP Behavior: Who Rolls vs Sells in CV Transactions (31:14) Four Filters for Durable Companies and Role of Founder Non-Greed (34:29) Longevity as an Asset Class and Implications for Pensions (37:03) Applying Longevity and Defense-Tech Themes in Manager Diligence (41:00) Innovation Capital as Part of Canada’s Sovereignty and Late-Stage Capital Gaps (44:33) How Emerging Managers Should Approach HarbourVest and Build Track Record (47:12) Connecting with Senia and Parting Thoughts (51:01) HarbourVest Partners is a global private markets investment firm managing approximately $150B in assets, with a 45-year history and venture as a core part of its franchise. The firm operates as a multi-strategy, multi-manager platform — primary fund investments, secondaries, direct co-investments, and credit — across North America, Europe, and Asia. Senia Rapisarda leads HarbourVest's Canadian strategy from Toronto, deploying capital across funds and growth-stage companies and serving as a bridge between the Canadian ecosystem and HarbourVest's global LP and GP network. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. HarbourVest Partners, LLC is a registered investment adviser under the Investment Advisers Act of 1940. This material is solely for informational purposes and should not be viewed as a current or past recommendation or an offer to sell or the solicitation to buy securities or adopt any investment strategy. The opinions expressed herein represent the current, good faith views of the author(s) at the time of publication, are not definitive investment advice, and should not be relied upon as such. This material has been developed internally and/or obtained from sources believed to be reliable; however, HarbourVest does not guarantee the accuracy, adequacy or completeness of such information. There is no assurance that any events or projections will occur, and outcomes may be significantly different than the opinions shown here. This information, including any projections concerning financial market performance, is based on current market conditions, which will fluctuate and may be superseded by subsequent market events or for other reasons. The information contained herein must be kept strictly confidential and may not be reproduced or redistributed in any format without the express written approval of HarbourVest. Nothing herein should be construed as a solicitation, offer, recommendation, representation of suitability, legal advice, tax advice, or endorsement of any security or investment and should not be relied upon by you in evaluating the merits of investing in HarbourVest funds or in any other investment decision. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • July 1 · 40 min

    Why This LP Is Staying Consistent in an Unpredictable Venture Market

    This week on Swimming with Allocators, Earnest and Alexa welcome Teddy Repko of the Yuhaaviatam of San Manuel Nation, who shares how his global upbringing, risk-aware personality, and early trading career shaped his investing approach, and how a shift at Columbia’s endowment from hedge funds to relationship-driven venture gave him a front-row seat to the asset class. He breaks down how LPs really underwrite managers—balancing base rates, power-law math, and portfolio construction with deep people and relationship assessment—and flags both opportunities and risks in today’s market, from mega funds, AI-driven valuations, and rapid funding cycles to concentrated DPI, late-stage growth, and crypto. Also in this episode, Nick Cassin explains how Sidley advises on secondary fund liquidity transactions, outlining the legal risks around transfers, why not all secondaries are created equal, and how structures like LP trades and strip sales are used across asset classes, including venture. Highlights from this week’s conversation include: Teddy’s Origin Story and Global Upbringing (1:14) Discovering the Columbia Endowment Allocator Role (3:06) Base Rates, Venture Math, and Manager Differentiation (8:20) Rise of Mega Funds and Impact on Seed Ecosystem (11:07) Valuation Concerns, AI Pace, and Compressed Diligence (13:47) Nick Explains Legal Risk and Why Not All Secondaries Match (16:10) Sidley’s Secondaries Practice Across Private Markets (20:18) Risks in Later Stage Growth and Crypto Ecosystem (23:04) Debating China Risk and Capital Return Constraints (26:23) Background on Yahavitatam Tribe and Sovereign Wealth Fund (0:27:10) How New Allocators Add Differentiated Value to Portfolios (30:15) Israeli Seed Ecosystem and Top of Funnel Differentiation (32:38) Relationship Building, AI Noise, and Handwritten Notes (36:34) Final Reflections on Venture FOMO and Consistent Allocating (37:02) Yuhaaviatam of San Manuel Sovereign Fund is a sovereign wealth fund managed from the Reservation of the Yuhaaviatam of San Manuel Nation near Highland, California. Yuhaaviatam of San Manuel Nation is a federally recognized American Indian tribe that exercises its inherent sovereign right of self-governance and provides essential services for its citizens through infrastructure development, governmental and civil services, and the advancement of social, economic, and cultural initiatives. The assets of the sovereign fund are managed by its executive leadership team in support of the Nation's long-term objectives and future generations. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • June 17 · 42 min

    Why Venture’s Best Opportunities Are Moving to the Edges

    This week on Swimming with Allocators, Kate Simpson joins Earnest and Alexa to share her journey from starting as a history major at the UNC endowment to leading the venture strategy at multi-asset OCIO firm GEM. She explains how she learned institutional investing, specialized in private markets, and refined her craft at Parish Capital and Truebridge, including fund-of-funds due diligence, reference work, and the power of platforms and networks. The conversation dives into how to build a venture program from scratch, why alignment, patience, and resource intensity matter, and how GEM uses a barbell approach across top-tier scaled platforms and emerging managers while avoiding the “crowded middle.” Kate breaks down how LPs evaluate managers (source, pick, win), why fund math and ownership are critical, and how today’s AI-driven cycle, secondary markets, and companies staying private longer are reshaping ventures. Also, don’t miss Nick Cassin from Sidley as he explains the rapid growth of the private-fund secondary market, what’s driving the surge in secondary and continuation vehicle (CV) transactions, and how new types of capital providers are stepping in as lead investors to provide liquidity to private-market participants. Highlights from this week’s conversation include: Starting at UNC Endowment With No Finance Background (0:31) Transitioning from TrueBridge to Gem and Taking on a Leadership Role (6:10) Advice for Building a New Venture Program and Aligning Stakeholders (10:12) Democratization of Venture Access and Barbell Strategy for Manager Selection (12:38) Sourcing and Evaluating New Venture Managers with a High-Volume Funnel (16:26) Secondaries Market Boom and Macro Dynamics Driving Liquidity Needs (21:00) Rise of Continuation Vehicles and Structural Evolution of Secondaries (23:36) How to Approach a First LP Meeting and Importance of Fund Math (26:03) Defining Early Versus Later Stages and Gem's Seed and Micro Fund Threshold (28:13) Normalization of Secondary Liquidity for Founders and Early Investors (35:24) Future Opportunities in Smaller Funds and the Dynamic Early Ecosystem (36:12) Final Thoughts and Takeaways (40:12) GEM is an independent investment management firm that provides customized solutions for long-term investors worldwide. Since 2007, we have sought to deliver superior risk-adjusted returns to our clients by combining disciplined investment research and active portfolio management with exceptional service and enduring partnership. With a global platform, broad institutional investment capabilities, and an experienced team, we design portfolios to meet the unique needs of each investor we serve. For more information, visit www.geminvestments.com. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • June 3 · 48 min

    DDQ: Celebrating 100 Episodes with Swimming with Allocators

    In this 100th episode of Swimming with Alligators, Earnest and Alexa dive into how emerging managers and VCs can truly differentiate in a world where everyone shows the same logos and track records. They unpack why LPs increasingly care about who actually sourced and led deals, why personal differentiation matters more than over-explaining strategy, and how consumer investing is quietly coming back into favor. They explore the limits of “AI strategies” that are more theater than edge, the shifting career paths for 30–40-something VCs, and whether the popular barbell approach to venture (tiny funds + megafunds) still fits a rapidly changing market. They also discuss how diligence is evolving, why moats now look more like trust, data, and distribution than pure tech, and what a wave of large IPOs could mean for angels, new funds, and early-stage competition. Highlights from this week’s conversation include: Celebrating 100 Episodes and DDQ Format (0:33) Differentiation in Fund Decks and Shared Logo Problem (2:12) Why Sourced vs Led Matters and Back-Channel Relationships (3:56) Overemphasis on Strategy vs True Differentiation and Team Cohesion (6:25) Pressure to Go Public, Headaches of Being Public, and Lawsuit Risk (10:14) OpenAI, Anthropic, SpaceX, and Logic of If They Do It, We Have to Do It (12:26) Enterprise VCs Moving into Consumer and Founders Rethinking Moats (14:11) Distribution, Brand, Trust, and Proprietary Data as Defensible Moats (16:25) Google, Personal Data, and Unseen Costs of Using LLMs (18:15) LPs Asking About AI Strategy and Congruent Use of AI Tools (20:44) Start ,Bench, Cut, Trade, and Suspend for 30s and 40s VCs (24:46) Allocators Following a Barbell Approach and Conventional Wisdom (27:11) LPs Diligencing Firm Strategy, Hiring, and Seed Creep at Large Funds (34:56) Audience Q&A Segment Introduction and Contact Information (37:13) Tinkering, Experimenting with Workflows, and Evaluating AI Tool Impact (39:07) Durability of Business Models, Trust, Distribution, and Manufactured Momentum (41:02) Post-IPO Talent Leaving, Mafias, and Angel-Backed New Founders (44:11) Closing Reflections on 100 Episodes and Looking Ahead to the Future (46:24) Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • May 27 · 48 min

    Cultivating a Venture Program Without Chasing the Hype

    This week on Swimming with Allocators, Earnest and Alexa welcome Mike Kakenmaster, Director of Investments at Loyola University Chicago, to discuss how a small endowment builds and scales a modern private capital and venture program. Mike shares his journey from hedge funds and a family office to Loyola, explaining how being a generalist across asset classes (hedge funds, buyout, credit, venture) helps him see risks, opportunities, and market cycles more clearly. The conversation covers the shift of LP attention between private markets and hedge funds, how Loyola doubled its private capital allocation, and why they moved deliberately into venture instead of rushing into brand-name funds. Mike also explains why early-stage track records can be misleading, how he evaluates managers (portfolio construction, reserves, access, networks, and founder/company quality), and why smaller and emerging managers can be especially compelling. Also, Chuck Daly of Sidley focuses on how first-time fund managers should thoughtfully build their operational and governance infrastructure, especially around disclosures and conflicts of interest, so they can run a real business, protect LPs, and clearly communicate how they’ll handle inevitable issues. Highlights from this week’s conversation include: From Hedge Funds And Family Office To Loyola Investment Office (0:30) What Keeps Mike Interested in Allocating and Fund Investments (3:14) Advantages of Being a Generalist Across Multiple Asset Classes (5:42) Shift of Capital Between Private Markets and Hedge Funds (10:30) Growing Loyola’s Private Capital Allocation and Building from Scratch (13:22) Early Days Entering Venture During a Hot Fundraising Environment (16:51) Operational Infrastructure, Disclosures, and Conflicts Framework for GPs (19:20) Governance Framework and Handling Unforeseen Conflicts of Interest (22:40) Avoiding Overreliance on Early Venture Track Records and Marks (27:53) Evaluating Reserves, Follow-On Decisions, and Portfolio Construction (32:14) Loyola’s Venture Strategy, Emerging Managers, and Fund Size Sweet Spot (34:34) Advantages of Partnering with Smaller Endowments for GPs (39:16) Advice to Smaller Endowments Starting a Venture Program (43:20) Final Thoughts and Takeaways (46:21) Founded in 1870, Loyola University Chicago is one of the nation’s largest Jesuit, Catholic universities, with nearly 17,000 students. The University has four campuses: three in the greater Chicago area and one in Rome, Italy, as well as course locations at our Retreat and Ecology Campus in Woodstock, Illinois. The University features 13 schools and colleges, including the Quinlan School of Business, Marcella Niehoff School of Nursing, Stritch School of Medicine, Parkinson School of Health Sciences and Public Health, Arrupe College, College of Arts and Sciences, School of Communication, School of Continuing and Professional Studies, School of Education, School of Environmental Sustainability, School of Law, School of Social Work, and Graduate School. Consistently ranked a top national university by U.S. News & World Report, Loyola is also among a select group of universities recognized for community service and engagement by prestigious national organizations like the Carnegie Foundation and the Corporation for National and Community Service. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • May 20 · 49 min

    What It Takes to Win With Institutional LPs

    This week on Swimming with Allocators, growth-investor-turned-LP Yuri Lee (TMRS) joins Earnest and Alexa and explains how her global upbringing and love of technology shaped her investing philosophy and belief that talent can come from anywhere. She walks through TMRS’s $3B and growing venture/growth mandate, how they split exposure between early-stage and multi-stage funds, and why they are building an aggressive 50/50 funds and co-investment program. Yuri shares what she looks for in emerging managers in clear, differentiated edge in sourcing, picking, or winning; true product–market fit between a manager’s edge and fund strategy; and non-consensus, outlier ideas. Throughout, she offers candid advice on how GPs can better pitch institutional LPs, why most decks sound the same, and what it really takes to stand out in a consensus-heavy, AI-dominated market. Also, Chuck Daly of Sidley talks about how emerging VC managers should think proactively about compliance, conflicts of interest, disclosure, and performance/marketing practices under (and aligned with) the Advisers Act and SEC’s marketing rule principles. Highlights from this week’s conversation include: How a Global Upbringing Shapes an Investor’s Worldview (0:13) Consumer Investing and Game Development Experience (2:22) Market Cycles in SaaS and Consumer Narratives (4:19) TMRS Mandate and Building a New Venture Program (6:16) Early Stage Managers and Differentiated, Non-Consensus Portfolios (9:20) What Matters Most at Early Stage vs Growth Stage (12:08) What LPs Really Want to Hear About: Companies and Decisions (14:11) How Pensions and Institutional LPs Run Diligence (17:04) Managing Portfolio Company Synergies and Conflicts (23:56) Marketing Rule Principles, Performance, and Case Studies (26:21) Why TMRS Uses Co-Invests and Target Mix With Funds (30:15) Barbell Approach: Early Stage Funds and Later Stage Co Invests (32:02) Information Gaps for LPs vs GPs and Founder Access (35:55) Consensus Rounds, Party Rounds, and Manager Profiles (38:56) Role of Non-Consensus Managers and Unique Edges (42:09) Rethinking AI Thesis and Value Capture by Model Labs (43:22) Advice For GPs Moving to LP Roles and Building Empathy (45:20) Final Thoughts and Takeaways (47:18) The Texas Municipal Retirement System is a $48+ billion public pension plan serving employees of participating Texas cities. TMRS invests across a diversified portfolio including public equities, fixed income, real assets, and private equity, with venture and growth investments forming an important component of its private markets strategy. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • May 13 · 55 min

    How Denmark Built a Big-Tech Future From a Small-Country Base

    This week on Swimming with Allocators, Erik Balck Sørensen joins Earnest and Alexa to share his journey from serial founder in an almost non-existent Danish startup scene to CIO of Denmark’s Export and Investment Fund, a sovereign platform backing innovation at scale. Erik explains how Denmark went from having no venture funds or ecosystem infrastructure to becoming a global player in biotech, green tech, and deep tech, and why “giving back” and tight founder communities were crucial to that evolution. He breaks down what it really means to run a sovereign wealth fund with a dual mandate, balancing financial returns for taxpayers with societal impact, and how political momentum, past missteps, and investment discipline shape their strategy. Erik also details Denmark’s 2030 plan: moving faster, professionalizing as an LP and direct investor, and doubling or tripling down on stronghold verticals like life sciences, selected green technologies, quantum computing, and European growth-stage capital. Additionally, Chuck Daly explains how evolving market dynamics, LP demands, and longer-dated, more complex venture products are reshaping the regulatory landscape for VC managers, driving greater scrutiny on valuation, fund structures, and exemptions, and highlighting the value of Sidley’s deep, shared institutional expertise for GPs navigating this shift. Highlights from this week’s conversation include: Erik’s Journey From Founder to Sovereign Wealth CIO (0:13) Community Building and Giving Back Culture (5:26) Corporates, Biotech, Green Tech, and Deep Tech (8:17) What Denmark’s Export and Investment Fund Is (9:39) Balancing Political Momentum, Purpose, and Profit (12:52) Small Country Strategy and Global Fund Partnerships (15:51) 2030 Strategy to Move Faster and Smarter (19:42) Priority Verticals: Biotech, Quantum, Green Tech, Growth (32:08) Misconceptions About the Fund and New Operating Style (36:58) Infrastructure Bets: AI Supercomputer and Quantum Facility (40:48) Technological Sovereignty and Europe’s Tech Dependence (44:14) Defense Technology Catch-Up with US Partners (48:47) Optimism From Founders and How to Contact Erik (51:01) Denmark´s Export and Investment Fund is a new, state-owned fund which proves a single point of contact to all Danish companies in need of state financed risk capital. We cover both the entrepreneur, small and medium-sized companies who need capital to unfold their full potential, and export companies who wish to conquer new or emerging markets. We can guide you all the way, from the company´s tentative beginnings through substantial growth to entry into the global markets with export guarantees and stock market listings, because our mission is to help to grow the Danish economy and green the globe. http://www.eifo.dk Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • May 6 · 46 min

    A New Playbook for Deep Tech Fund Investing

    This week on Swimming with Allocators, Wes Panek joins Earnest and Alexa to share his unconventional journey from consulting and international development to venture capital, and ultimately to his current role as an LP at the Astera Institute, a multi-billion-dollar foundation focused on deep tech and frontier science. Wes explains how his family background shaped his desire to make markets work for everyone, what he learned evaluating hundreds of emerging managers at Screen Door, and why he believes there is no single playbook for success in venture. He breaks down how and why Astera is adding fund investing alongside grants and research, the structural advantages of foundations backing deep tech funds, and the gaps he sees in LP coverage of technical managers. Wes also offers practical lessons on building a new fund-of-funds program from scratch, including the importance of deploying capital sooner, being highly selective with time, and leveraging flexibility without losing discipline. For LPs and GPs interested in deep tech, he shares advice on underwriting technical strategies without a PhD, the rare “unicorn” profile of ideal managers, and concrete qualifiers for funds that might be a fit for Astera’s capital. Additionally, Chuck Daly of Sidley explains how today’s SEC and global regulators are refocusing on core anti-fraud, valuation, conflicts of interest, and disclosure principles for venture managers, with growing state and international scrutiny—especially around process, governance, and ESG — outside the US. Highlights from this week’s conversation include: Wes’s Journey From Consulting to International Development and Venture (0:35) Learning GP–LP Dynamics and Two Customers in Venture (3:55) Mission of Astera Institute and Focus on Frontier Tech (5:54) Adding Fund Investing and Deep Tech Focus at Astera (7:19) Designing Astera’s Deep Tech Fund Strategy as an Experiment (11:05) Regulatory Priorities for VC Managers: Communication and Anti Fraud (15:45) SEC Expectations on Valuation Process and Consistency (20:21) Global Regulatory Trends and ESG Focus for Venture (23:20) Foundation vs Fund of Funds: Flexibility, Risk, and Time Horizon (28:36) How Astera Underwrites Deep Tech Funds and Direct Investments (29:09) Do LPs Need To Be Technical and How To Skill Up (34:43) Ideal Traits of Deep Tech GPs and Wes’s Bias Toward Technical Founders (39:52) Fund Parameters Wes Backs: Size, Stage, and Themes (43:20) Astera Institute is a philanthropic organization dedicated to advancing frontier science and technology for the benefit of humanity. The Institute supports in-house scientific research, grantmaking, direct investments, and fund investing to accelerate progress in areas such as artificial intelligence, neuroscience, energy, and other deep-tech domains. Learn more at asterainstitute.org. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • April 29 · 46 min

    Aligning Capital With Community Impact

    This week on Swimming with Allocators, Alexa Binns and Earnest Sweat talk with Avivar Capital Co-Founders Lisa Richter and Tina Castro about how they built an impact investing firm focused on aligning capital with social and environmental outcomes. They trace their paths from ShoreBank, Goldman Sachs, and the California Endowment to launching Avivar, and explain why all investing has impact, positive or negative. The conversation covers place-based investing, creative deal structuring for disaster recovery (like post-wildfire efforts in California), using venture capital as the right tool for scalable solutions such as edtech, and their distinctive approach to diligencing emerging managers without conventional track records. Key takeaways include starting with the end impact in mind, matching capital type to the problem, the power of proximity to communities being served, and why persistence and thoughtful risk-taking are essential to building more equitable capital markets. Also, don’t miss Michael Podolny from Sidley as he explains that his startup clients are increasingly dealing with early founder breakups and complex AI/data licensing issues, and that he now relies on AI tools daily to dramatically speed up legal work while preserving his core advisory value. Highlights from this week’s conversation include: Lisa’s Path From ShoreBank to Impact Investing Advisory Work (0:34) Transition from Wall Street to Impact Investing (2:46) Launching Independent Practices and Merging Into Avivar (4:09) Moving From Impact Theory to Practical Execution (8:37) Comprehensive Mission‑Aligned Investment Approach (11:23) Starting With Outcomes and Choosing the Right Type of Capital (14:31) Creative Structuring Example for Wildfire Recovery Capital (17:35) AI, Data Licensing, and Deal Structures (20:31) Handcrafted Deals, AI’s Role, and Scaling Impact (24:30) All Investing as Impact and Reframing Positive Impact Investing (27:39) Diligencing Emerging Managers With Nontraditional Track Records (32:11) Venture Capital for Scaling Digital Education Solutions (35:43) Standout GP Characteristics and Key Signals (38:37) Reflections on a Decade of Building Avivar (41:52) Pride in Team, Talent, and Firm Culture (43:09) Final Thoughts and Takeaways (44:06) Avivar Capital is a women-led registered investment advisor founded to advance impact investing and system-level change. Emerging from The California Endowment and built on decades of mission-driven experience, Avivar specializes in rigorous evaluation of first-time managers and partners only with investors who share a vision for equity, inclusion, and catalytic capital. Learn more at www.avivarcapital.com. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • April 22 · 40 min

    Rethinking the Venture Co-Investment Playbook

    This week on Swimming with Allocators, Juan Diego Briceno (JDB) shares his journey from New York private banking and Latin American wealth management to building and spinning out Pomifer Capital, an “extension of family office teams” focused on private equity and venture capital. He explains how sophisticated family offices think about alternatives, why many learn the hard way that they shouldn’t try to be full-time VCs, and how to avoid adverse selection in both direct deals and co-investments. The conversation covers hype cycles and climate investing, the dangers of over-concentrating in themes, what makes a family office truly institutional-ready, and how to design a durable venture program through vintage diversification, strategy mix, and manager selection. JDB also breaks down key differences between PE and VC (from GP backgrounds to data transparency), why traditional PE-style co-investing often fails in venture, and how creative structures like lower management fees with higher carry can better align GPs and LPs. Also, Michael Podolny of Sidley explains how current macro uncertainty and the AI boom are slowing some venture deals, concentrating capital into a few “prized” AI companies, driving consolidation and acqui-hires, and sparking an early comeback of SPACs for high-growth startups. Highlights from this week’s conversation include: Learning to Relentlessly Advocate for Clients in Wealth Management (1:10) ​​Climate Co Investments and Managing Venture Hype Cycles (3:26) Why Family Offices Should Not Do All Venture Deals Direct (5:38) Spinning Out to Create Pomifer Capital (8:02) Designing PE and VC Programs With Patient, Flexible Capital (10:03) Examples of Patient Capital and Holding Concentrated Winners (12:12) Macro Environment and AI-Driven Markets (15:12) How Startup Legal Practice Has Evolved and Globalized (18:25) Automating Rote Legal Work and Focusing on High Stakes Advice (19:55) Why Starting a Venture Program Is Hard for Family Offices (21:08) Traits of Top-Performing Venture Managers (23:31) Questions to Test GP Self Awareness and Blind Spots (25:52) Data Transparency Differences in Private Equity and Venture (28:05) Who Should Reach Out to Pomifer For Capital (34:23) What Juan Wants to See More of in GP Strategy and Firm Design (35:27) Final Thoughts and Takeaways (37:43) Pomifer Capital Partners is a Registered Investment Adviser based in Texas, serving as an extension of family office investment teams. Pomifer focuses on differentiated venture capital and private equity fund investments, co-investment opportunities, and other distinctive private-market strategies. Registration as an investment adviser does not imply a certain level of skill or training. The information provided is for informational purposes only and does not constitute a solicitation or recommendation. Additional information, including services, fees, and potential conflicts of interest, is available in Pomifer Capital’s Form ADV Part 2A. Learn more at www.pomifercapital.com Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • April 15 · 48 min

    What LPs Want and GPs Need to Hear

    This week on Swimming with Allocators, Earnest and Alexa chat with Regina Green as she shares her journey from growing up as “the different one” in Georgia to spending 17 years at Goldman Sachs and leading the Launch With GS initiative focused on channeling capital to underrepresented founders and fund managers. She explains how that experience led her to Catalyze, where she now supports “capital entrepreneurs” through a GP fellowship and the GP Runway Fund, providing working capital loans to emerging managers building institutional-quality firms. Key takeaways include the importance of context and empathy in investing, why diversity strategies must start early in the capital stack, how GPs should think about firm-building beyond deal-making, and why Regina is optimistic about the rise of innovative capital products and more inclusive asset management over the next three to five years. Also, Michael Podolny of Sidley explores how secondary and tender offer markets have evolved into a standard part of late-stage private companies’ path to IPOs, highlighting who’s buying these shares, how deals are structured, and the legal/structural pitfalls GPs and companies need to navigate. Highlights from this week’s conversation include: Identity, Perspective, and Being Different In Predominantly White Institutions (0:21) Southern Upbringing, Magnet Schools, and Becoming a Listener (3:04) Launch with GS and Diversity in Venture (4:09) Rethinking Institutional Diversity Programs in 2020 (9:44) Equipping New Managers and Filling Early Stage Capital Gaps (12:32) Catalyze, Capital Entrepreneurs, and Innovative Capital Products (16:02) Firm Infrastructure, Service Providers, and GP Working Capital (19:07) Strategic Investors and Secondary Only Funds In Growth Stage Deals (24:29) Blended Valuations Across Primary and Secondary Rounds (27:36) Staying High Touch with Capital Entrepreneurs at Catalyze (29:09) GP Stakes Versus Non-Dilutive Working Capital Loans (31:55) How LPs View GP Stakes and GP Loans (35:50) Treating LP Outreach Like a Sales Process (39:06) Signals of Enduring Firms and Long-Term Orientation (42:00) Innovative Capital, Wealth Building, and Future Optimism (45:40) Catalyze is a national platform that provides Capital Entrepreneurs with the capital and support they need to build enduring firms. Catalyze also operates capital solutions including the GP Runway Fund, extending flexible working capital loans to underrepresented and innovative investors raising funds one through three. https://catalyze.community/ Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • April 8 · 44 min

    The Allocator’s Checklist: How LPs Size Up Managers

    This week on Swimming with Allocators, Earnest and Alexa welcome Charlotte Zhang, Senior Portfolio Manager at Inatai Foundation. Charlotte shares her unconventional path from tech investment banking into LP life, her work at Inatai Foundation, and how she evaluates fund managers across asset classes. She explains Inatai’s mission-driven, endowment-style strategy centered on efficiency, innovation, and impact, and how they manage capital for other aligned foundations. She also shares how generalist allocators run thematic research sprints, why they avoid rigid asset class buckets, and how they think about biotech, crossover, and platform value creation. For venture managers, she outlines what LPs look for: real differentiation rooted in an unmet need, some form of specialization, strong networks and early access, and the “four Ps” all anchored in people with integrity and learning agility. Also, don’t miss Michael Podolny as he explains how Sidley’s emerging companies practice is increasingly busy as AI-driven and globally ambitious startups seek sophisticated, full‑lifecycle legal and tax advice from day one, with a particular focus on planning early to maximize QSBS tax benefits and founder outcomes. Highlights from this week’s conversation include: Charlotte’s Path From Banking to Allocator (1:12) Inatai’s Mission and Investment Focus On Racial Justice (6:12) Investment Strategy and The “Three I’s” (Inefficiency, Innovation, Impact) (7:54) Managing Multiple Asset Classes W\with Thematic Research (12:23) How Sidley Supports Sophisticated, AI-Driven Startups and QSBS Planning (18:25) What Emerging Managers Get Wrong With Foundations and OCIOs (23:39) Why Specialization and Differentiation Matter in Venture (24:09) Charlotte’s Take on Venture Versus NASDAQ and Top-Decile Returns (36:38) Charlotte’s Immigrant Background and Empathy or Underdogs (41:19) Inatai Foundation is a 501(c)(4) philanthropy seeking to transform the balance of power to ensure equity and racial justice across Washington state and beyond. The organization is accountable to leaders and organizations building power in racially diverse communities in Washington state and seeks to primarily fund community based organizations led by people of color. With a team based throughout Washington, it works to advance four distinct areas of work: relationship building, policy and advocacy, investment management, and grantmaking. Learn more at www.inatai.org. Inatai Investment Management Company is guided by the belief that successful investing is about more than money. The organization leverages extensive expertise, deep resources, nimble governance structure, and knowledgeable investment managers to generate long-term, sustainable returns for Inatai Foundation and other mission-aligned organizations, using a cost-sharing model. The investment options chosen are determined not just for their potential for growth but for how they support our values and the positive impact they may achieve for the world. Our goal is to become a proactive, community-driven force for change in capital markets and in the investment sector at large. Learn more at www.inatai.partners. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • April 1 · 45 min

    Power Laws, Secondaries, and Staying Consistent: StepStone’s VC Framework

    This week on Swimming with Allocators, Earnest and Alexa chat with Anthony Giambrone, Partner at StepStone Group. Anthony shares his unconventional path from gas station manager and nightclub worker to leading a major global venture allocation platform. The conversation covers his break into investment banking, the scaling of GreenSpring into StepStone, and why relationships, EQ, and consistency across vintages matter more than market timing in venture. Key takeaways include the power-law nature of VC returns, how emerging managers and spinouts can stand out with a real edge and long-term relationship-building, why asset quality matters more than discounts in secondaries, and how AI, liquidity pressures, and longer private company lifecycles are reshaping the next decade of venture capital. Also, Rebecca Stuart, an employment-focused partner at Sidley, explains how she helps venture-backed companies navigate complex employment and co‑founder separations, equity and vesting pitfalls, evolving worker classification and pay transparency laws, and the fast-changing regulatory landscape around AI in hiring and employment decisions. Highlights from this week’s conversation include: Anthony’s Background and Humble Beginnings (0:42) Importance of Empathy and Relationships in Venture (4:16) Applying Greenspring/StepStone Experience to Today’s Market (6:15) StepStone Venture Team, AUM, and Global Footprint (8:07) Why You Can’t Time Early Stage Venture (9:38) Vintage Volatility and Power Law in Venture Outcomes (11:23) How Founder Ambition Affects GP and Fund Diligence (14:28) Insider Segment: Co‑Founder Divorce (18:04) Using New Investments to Clean Up Equity and IP (21:43) Employees Demanding Human Review in AI‑Driven Processes (25:43) Fund Slot Constraints and LP Down‑Selection (28:33) Advice for New LPs on Capturing Upper Quartile Returns (31:36) Is Top Quartile Performance Still Good Enough? (33:08) Secondaries Strategy and Asset Quality Over Discounts (34:31) Liquidity Pressures, DPI, and GP‑Led Solutions (38:37) StepStone’s 10‑Year Lifecycle Partner Vision (40:35) StepStone Group is a global private markets firm focused on providing customized investment solutions and advisory and data services to its clients worldwide. The firm’s venture capital and growth equity platform, built on the foundation of Greenspring Associates, manages $25B+ in AUM across primary fund investments, secondaries, and co-investments, as of June 30, 2025. Learn more at www.stepstonegroup.com. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • March 25 · 39 min

    DDQ: Founders, Fraud & ‘Fake It Till You Make It’

    This week on Swimming with Allocators, it’s time for another discuss, debate, and question (DDQ) episode as Earnest and Alexa riff on founders behaving badly and the cultural and governance failures enabling fraud-like behavior, then dive into how enterprises will actually adopt AI and what that means for the future of SaaS and vertical software. They unpack the rise of GP-led secondaries, strip sales, and mounting impatience around liquidity, using recent market data to explain why secondary activity is accelerating. The conversation shifts to Brendan Baker’s three-tier venture framework (mega, middle, and small funds), where they debate where innovation, desperation, and real differentiation will come from. They explore whether LPs should back first-time fund managers without a traditional track record, what “track record” should really mean, and why softer skills, pattern recognition, and learning velocity matter. They also discuss treating fundraisers like enterprise B2B sales, how to qualify LPs and build authentic GP–LP relationships, and close with a playful “start, bench, cut” on SpaceX, OpenAI, and Anthropic to frame how they think about pre-IPO AI and space bets. Highlights from this week’s conversation include: Prediction: 2026 as the Year of Founders Behaving Badly (1:16) Misuse of Startup Funds and Rise in Legal Issues (1:48) Narrative-Driven Investing and Weak Governance in VC (2:28) Enterprise AI Adoption: Rory O’Driscoll’s Five Paths (3:25) Will Big SaaS Survive the “SaaS Apocalypse”? (5:43) LP Liquidity Pressure and GP-Led Secondaries (9:19) Data on Secondary Pricing, Continuation Vehicles, and Strip Sales (12:04) Venture Splitting into Mega, Middle, and Small Funds (15:26) Desperation, Differentiation, and Innovation Across Fund Sizes (17:52) Should LPs Back First-Time Fund Managers Without a Track Record? (21:41) Learning Velocity, Curiosity, Kindness, and Willingness to Schlep (24:49) The Value of Apprenticeship and Seeing Portfolios Over Time (25:50) Game: Start, Bench, Cut – SpaceX, OpenAI, Anthropic (30:16) One Question to Ask a First-Time Fund Manager (34:32) Signs of Strong GP–LP Fit: Informal Contact and Vulnerability (36:48) Closing Remarks and Episode Wrap-Up (37:40) Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

  • March 20 · 49 min

    How to Separate Yourself When Everyone Has the Same Deck

    This week on Swimming with Allocators, Earnest and Alexa welcome Zach Ruchman, Shareholder & Managing Director, Private Investments at HB Wealth. Zach shares how his unconventional path through the Middle East, international development, consulting, and BlackRock has helped shape the way he makes decisions under uncertainty and evaluates managers. He talks about why venture requires comfort with long duration and illiquidity, why fund size defines strategy, and how alignment of incentives between GPs and LPs really works. Zach explains HB Wealth’s multi-family office approach to private markets across credit, real estate, private equity, and venture, and stresses that in a crowded VC market, authentic differentiation, deep curiosity, and long-term relationship building still matter more than any tool or trend. Also, Rebecca Stuart of Sidley explains how founders and VCs should think about non‑competes, non‑solicits, and trade secret protection in a multi‑state, remote‑work world, emphasizing practical, enforceable ways to safeguard talent and IP as restrictive covenant law shifts across the U.S. Highlights from this week’s conversation include: Zach’s Non-Linear Path and LP as the Best Job in Finance (0:31) Investing Into Uncertainty and the Need for 10x Venture Outcomes (2:33) Fund Size as Strategy and How Cost of Capital Shapes Venture Models (4:44) HB Wealth Overview, AUM, and Focus on Private Markets (7:25) How HB Packages Private Offerings for Different Client Profiles (8:35) Incentive Alignment, Fees, and Why Zach Prefers Smaller Managers (11:09) What True GP-LP Partnership Looks Like Beyond Formal Diligence (12:45) Radical Transparency, Learning Velocity, and Updating Investment Priors (15:07) Full Life Cycle Counsel for Venture Backed Companies (17:29) Non Competes, Regulatory Shifts, and Implications for VC Portfolios (19:31) Non-Solicitation Agreements, Remote Teams, and Multi-State Compliance (22:32) Trade Secrets, IP Assignments, and Layered Protection Strategies (24:59) Differentiation in a World with Thousands of Venture Funds (27:07) Authentic Superpowers, Avoiding Generic YC Adjacent Strategies (32:58) Venture as an Essay Test and the Industry’s Maverick DNA (35:52) What Drives Quick Passes and Alignment Issues for New Funds (39:18) How LPs Triage Email, Say No, and Capacity Constraints on Commitments (41:24) Advice To High Net Worth Families Entering Venture (44:03) Long Term Optimism About Innovation and Private Markets (45:54) HB Wealth is a national independent wealth management firm providing fiduciary, fee-only investment management and financial planning services. With over $28 billion in assets under management and more than 3,700 client relationships nationwide, HB helps families, executives, and entrepreneurs steward their capital with purpose. Learn more at www.hbwealth.com. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

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