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

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

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

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

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

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

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

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

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

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