In this episode, Courtney and Jacob explore the art and science of standing out in a crowded market—from shaping a compelling story arc and demonstrating authentic access, to developing a strategy that feels differentiated yet credible. She shares common pitfalls GPs make when pitching LPs, why emotional intelligence and operational polish matter, and how to maintain grace and persistence through the long fundraising journey.

Finally, Courtney offers practical advice for navigating today’s challenging environment: how to right-size your fund, close capital efficiently, and find overlooked LP archetypes beyond the traditional endowment base. For any GP raising a fund or building toward institutional scale, this conversation delivers both high-level wisdom and tactical guidance straight from one of venture’s most respected LP voices.

She walks us through the realities of building as a solo GP, from finding her anchor investor almost by accident, to proving her thesis with small checks before scaling up her ownership strategy. Samara also shares tactical insights on working with institutional and non-traditional LPs, including corporates, family offices, and state treasurers, and how she positioned Chingona to align with both regional development goals and later-stage VCs seeking differentiated deal flow. For emerging managers, her candid perspective on “just getting into business” and proving even a slice of the thesis is an invaluable playbook for raising and scaling a fund.

Finally, Samara dives into timely topics that all GPs face today: liquidity and secondaries, the tradeoffs between following the LP “playbook” and pursuing true DPI, and why proactive relationship-building with bankers and PE funds matters even at pre-seed. Her reflections on staying in the game long enough to let fund-makers emerge, combined with her commitment to mentoring the next generation of investors, offer both practical and inspiring lessons. This episode is essential listening for GPs navigating fund strategy, LP alignment, and long-term firm building.

The conversation also dives into recruiting strategy and execution—from scoping roles and structuring compensation, to deciding between hiring to “sustain” versus “extend” a firm’s strategy. Dan shares actionable benchmarks for comp and carry at every level, explains why sourcing is the biggest reason operator-hires often churn, and unpacks what the best GPs get right when working with search firms. Whether you’re a solo GP about to make your first hire or leading a multi-partner platform buildout, this episode is a blueprint for hiring intelligently in a rapidly evolving talent market.

Yannick explains the different structures available in secondary transactions, including continuation vehicles, tenders, staples, secondary directs, and structured solutions. He emphasizes that continuation vehicles are the most common, allowing managers to hold onto assets longer while giving existing LPs the option to reinvest or cash out. The conversation also touches on the importance of transferability analysis and fairness opinions in these transactions. Yannick advises GPs to consider the market conditions, fund performance, and LP expectations when deciding on a secondary structure.

The discussion highlights the nuances of pricing in the secondary market, noting that discounts are not always negative but rather relative to market conditions and asset performance. Yannick also addresses common misconceptions about the secondary market and provides guidance on managing LP expectations and avoiding pitfalls during the process. The episode offers valuable insights for venture capitalists navigating the complex landscape of secondary transactions.

The information contained in this podcast does not constitute research or recommendation from any Mizuho entity to the listener. Neither Mizuho nor any of its affiliates make any representation or warranty as to the accuracy or the completeness of the statements or any of the information contained in this podcast, and any liability therefor, including in respect of direct or indirect or consequential losses or damage, is expressly disclaimed.

The views expressed in this podcast are not necessarily those of Greenhill or Mizuho, and Mizuho is not providing any financial, economic, legal, accounting, or tax advice, or recommendations in this podcast. In addition, the receipt of the podcast by any listener is not to be taken as the giving of investment advice by Mizuho, nor to constitute that person a client of any Mizuho entity.

Greg discusses the evolving landscape of the secondary market, highlighting how company-sponsored liquidity events and GP-led transactions have become increasingly common as companies stay private longer. He breaks down the ideal characteristics of secondary deals, the types of buyers involved, and the typical transaction sizes, as well as the nuances of price discovery, deal structuring, and the role of platforms versus trusted brokers.

Listeners will gain practical advice on navigating the complexities of secondary sales, including how to approach pricing, the importance of discretion, and the value of working with experienced partners. Whether you’re a GP seeking liquidity for your fund or an LP considering a sale, this episode offers a comprehensive guide to today’s dynamic secondary market.

Matt details the services Two Meter Capital provides, from tracking portfolio company performance and writing reports, to identifying secondary sale opportunities, assisting with follow-on rounds, and supporting annual audits and valuations. He shares insights on when GPs should consider bringing in outside help—typically when managing legacy portfolios becomes a persistent drag on resources, or when firms are deciding whether to raise another fund or wind down operations. The conversation also covers the economics of harvest management, the ideal client profile, and how Two Meter Capital’s tech-enabled approach can add value without replacing the GP’s core decision-making role.

Listeners will gain a practical understanding of the challenges facing today’s venture funds as the industry matures, and how specialized partners like Two Meter Capital can help optimize outcomes for both established and emerging managers. Whether you’re a GP stretched thin by a growing portfolio or a family office grappling with legacy investments, this episode offers actionable advice for navigating the evolving venture landscape.

Ezra introduces the "Magic Box Paradigm," a visual and practical approach that helps founders and investors focus on the unique value their company can unlock for specific buyers—what he calls the "purple squares." He explains why M&A is fundamentally different from fundraising, how to avoid the pitfalls of a sales-driven mindset, and why starting early with strategic relationship-building is key. The conversation covers actionable advice for VCs and board members on how to guide their portfolio companies, the importance of thought leadership, and how to navigate both strategic and private equity exits.

Listeners will come away with a fresh perspective on startup M&A, including when to bring in advisors, how to structure deals creatively, and why conventional wisdom—like relying on competitive bidding or rushing to term sheets—often falls short. Whether you’re a founder, investor, or board member, this episode offers a masterclass in preparing for and executing high-impact M&A outcomes.

Sara breaks down the mechanics and motivations behind GP-led secondary transactions, including continuation vehicles, tender offers, and NAV loans. She discusses why these deals are increasingly popular, how they can help GPs crystallize carry, reset team incentives, and provide follow-on capital for portfolio companies. The conversation covers the importance of aligning with LPs, running a competitive process to determine fair pricing, and navigating complex tax and regulatory considerations—especially for venture funds.

Listeners will gain actionable insights on when a GP-led secondary makes sense, how to structure these transactions, and what pitfalls to avoid. Whether you’re a fund manager considering liquidity options or an LP curious about the process, this episode offers a comprehensive, practical guide to the fast-evolving world of venture secondaries.