From Juilliard to $6B AUM: How a Musician Built One of Venture's Most Unconventional Endowments

Origins hosts Nick Chirls (GP, Asylum Ventures) and Beezer Clarkson (LP, Sapphire Partners) react to their conversation with Nicholas Csicsko, a public/private investor at Trinity. They dig into his framing of “cynical optimism” and why it might be the right posture for venture investing, unpack the growing obsolescence risk for SaaS companies from earlier vintages, and cap it off with a live question: if sovereign wealth pulls back from US venture, what breaks first?For a monthly roundup of the latest venture insights, including the newest Origins episodes, subscribe to the OpenLP newsletter – delivered straight to your inbox: https://subscribe.openlp.vcCHAPTERS:00:00 Welcome to Origins00:54 Musicians as Investors01:39 Cynical Optimism Explained02:47 Investor Role Beyond Cheerleading03:11 Steadying Founder Emotions05:59 SaaS Obsolete Before Liquidity07:06 Old SaaS Playbook Breaks08:00 Lovable Growth Reality Check09:01 Creative Destruction Across Portfolios10:17 LP Optimism and Venture Nuance11:26 Ugly Truths About Great InvestorsLearn more about OpenLP: https://openlp.vcLearn more about Asylum Ventures: https://asylum.vcLearn more about Sapphire Partners: https://sapphire.vc

What happens when a classically trained musician from Juilliard ends up managing a $6 billion endowment? Today's episode of Origins explores exactly that journey - and what it reveals about how the best institutional investors really think.Nicholas Csicsko, Managing Director of Investments at Trinity Church NYC, brings a rare perspective to venture capital - one shaped by years of classical music training, a doctorate from Juilliard, and a decade building out one of America's most unique institutional investors. Trinity Church, founded in 1697 and endowed with 215 acres of Manhattan by Queen Anne in 1705, has grown its diversified investment pool to over $4 billion under Nicholas and CIO Meredith Jenkins.Together with hosts Nick & Beezer, the group digs into what institutional LPs really look for in venture managers, and what puts them off. From the tension between patient capital and the need for liquidity, to skepticism around sky-high private market valuations and the growing disconnect between private and public markets, Nicholas delivers the kind of frank, independent thinking that makes for a truly exceptional investor.Along the way, they explore the virtues of "cynical optimism" in early-stage investing, the institutional pressures that push LPs toward brand-name funds, and why Nicholas believes the best venture managers are those who know themselves deeply. From the challenges of scaling a venture firm to whether today's AI-driven capital surge is sustainable, this conversation offers a grounded, data-aware take on what it takes to build lasting returns in private markets.—Quotes"If you could put a bunch of investments into a line item that wasn't going to receive scrutiny, that left tail risk of something going to zero would probably be less. But if it's visible, it's discussable. You probably don't get fired for doing the next a16z fund, but you might be questioned if you take a flyer on someone who's up and coming. And so there's this institutional pressure towards, dare I say, conformity. But what's safe? What's perceived as safe?”"It's all fine and good that folks think they can raise and put more money to work, but I'm a little worried about where it's taking us because when open AI raises around 4x larger than any IPO in history, I kind of worry that we're creating a market that is not sustainable because ultimately there's not enough liquidity. There is a massive disconnect there.”"Knowing thyself is probably the number one thing I would attribute to all of the best investors I've met. And as they get older and more experienced, they know what they think they need more and more without stopping challenging their bias, without adding that new person to make them better.”—Time Stamps00:55 Meet Nicholas Csicsko, Managing Director, Investments at Trinity Wall Street02:24 Musician Mindset to Investing03:40 From Juilliard to Finance05:56 Trinity Church Endowment Story09:56 Building the Portfolio and Venture12:31 Institutional Risk and Conformity14:47 Private Public Market Disconnect18:57 DPI, TVPI and Secondaries20:41 Backing Off Radar Managers23:47 Cynical Optimism in Venture28:04 Building a VC Firm Team34:34 Where Venture Fits Today39:02 Too Much Capital and Liquidity?42:20 Closing and Next Episode—LinksConnect with the guest and hosts on LinkedIn!Nicholas CsicskoBeezer ClarksonNick ChirlsLearn more about:Trinity Church NYCAlfred P. Sloan FoundationOpenLPAsylum Ventures

Origins hosts Nick Chirls (GP, Asylum Ventures) and Beezer Clarkson (LP, LGT Capital Partners) unpack a recent conversation with David Clark, CIO of VenCap International PLC on megafunds vs small funds and a16z returns. They also discuss Beezer’s article “I See Dead VCs,” which explores how VC is in the first meaningful industry-wide contraction in modern venture history, risks to seed formation, and the workstreams required for emerging managers to institutionalize and endure.For a monthly roundup of the latest venture insights, including the newest Origins episodes, subscribe to the OpenLP newsletter – delivered straight to your inbox: https://subscribe.openlp.vcCHAPTERS:00:00 Welcome to Origins00:33 David Episode Takeaways02:01 I See Dead VCs Article02:59 Venture Contraction Data04:17 Fund Survival Math05:47 Seed Ecosystem Risk07:35 What Gets You to Fund Two08:48 Building a Durable Firm11:13 Traits of Long Run ManagersLearn more about OpenLP: https://openlp.vcLearn more about Asylum Ventures: https://asylum.vcLearn more about VenCap: https://www.vencap.com/Read Beezer’s article “I See Dead VCs”: https://www.linkedin.com/pulse/i-see-dead-vcs-elizabeth-beezer-clarkson-uc4xc/

What does patience look like today when the best companies take 10–15 years to exit, and is it still worth it to wait that long? Today’s episode of Origins dives into one of the most pressing questions in today’s market: how to balance long-term conviction with the need for liquidity.David Clark, CIO of VenCap and a three-decade veteran of institutional venture investing, returns to the show to bring his rare LP perspective shaped by backing some of the most established venture franchises in the industry. Known for a data-first approach, David offers insight into how top-tier firms consistently generate returns, and how those dynamics evolve as fund sizes scale into the billions.Together with hosts Nick & Beezer, the group explores the implications of venture capital consolidation, the persistence of power law outcomes, and the shifting role of liquidity in private markets. From the rise and returns of mega-funds like a16z, to the growing importance of secondaries and delayed IPO timelines, the conversation surfaces the core tension of capturing extreme right-tail outcomes while still delivering tangible distributions to LPs. Along the way, they debate whether “patient capital” is truly a viable strategy, or if today’s venture structure inherently rewards more active portfolio management. Ultimately, today’s discussion offers a data-driven look at how venture is changing and how fund managers can look to stay ahead.—Quotes“If our managers have one of those top 1% companies, we want to encourage them to let it ride. Because we don't see the very best managers selling their best companies prematurely. That's not how we've seen the best fund level performance. And if you are able to hold those companies through to their full potential, that's where the real value is created.” – David Clark“I actually think the late stage private markets have become the public markets for early stage venture fund managers. And I think if you consider [that possibility], you can find much more predictability and consistency in performance, returns, and DPI. As much, or maybe even more than large later stage managers.” – Nick Chirls“What I've seen in the last few years is people taking exits into consideration, which makes my heart very happy. Because for years people were not, and they weren't thinking about returning capital along the way. You can take 10%, 20% and return 1x or 2x your fund. That is a very credible conversation to have with your LPAC.” – Beezer Clarkson—Time Stamps01:13 Meet David Clark, CIO of VenCap03:29 a16z Fundraising Surge05:31 First Principles Venture Model07:18 Public Markets And IPO Scale09:32 Do Big Funds Want Private13:17 Power Law Still Rules14:28 Fund Size And DPI Timing16:36 Early Stage Fund Math20:59 Small Funds Versus Platforms24:02 Portfolio Construction Tradeoffs25:40 Late Stage As New Public28:44 Liquidity As A New Skill30:55 When To Take Chips Off33:25 Founder Secondaries And Alignment35:13 Venture Capital Consolidation Risks40:47 Big Firms Funding Emerging Managers44:30 Patient Capital Debate48:00 Going Public Incentive Concerns—Links Connect with the guest and hosts on LinkedIn!David ClarkBeezer ClarksonNick ChirlsLearn more about:Read Packy McCormick's blog post on a16z: The Power BrokerVenCapOpenLPAsylum Ventures

Origins host Beezer Clarkson,  LP at Sapphire Partners and co-founder of OpenLP, and Nick Chirls, GP at Asylum Ventures, dig into their recent conversation with Dan Gray, prolific venture writer and Research Lead at Odin. They discuss various levels of risk tolerance across the ecosystem – including who the data says can stomach more – whether GPs are giving up on founders earlier than they used to, and whether Dan’s recent deep dive into changing LP behaviors matches anecdotal wisdom in the world of venture.Learn more about Sapphire Partners: sapphireventures.com/sapphire-partnersLearn more about OpenLP: openlp.vcLearn more about Asylum Ventures: asylum.vcLearn more about Odin: joinodin.comRead Dan’s Writing on VC: credistick.comRead the Results of Dan’s Survey: credistick.com/lp-2025For a monthly roundup of the latest venture insights, including the newest Origins episodes, subscribe to the OpenLP newsletter – delivered straight to your inbox: subscribe.openlp.vcCHAPTERS:0:00 Welcome to Origins0:44 Questioning Assumptions In Venture3:31 Does Having More Companies In Your Portfolio Increase Your Appetite For Risk?8:41 Nick’s Risk ToleranceOrigins is produced by Sapphire Ventures in partnership with⁠⁠ Pod People.⁠Nothing presented herein is intended to constitute investment advice, and under no circumstances should any information provided herein be used or considered as an offer to sell or a solicitation of an offer to buy an interest in any investment fund managed by Sapphire Ventures, LLC (“Sapphire”). Any offer or solicitation of securities by Sapphire may only be made in accordance with the current offering documents for a managed Fund in which Sapphire is an advisor. Additionally, Sapphire does not solicit or make its services available to the public; such offerings may only be provided to accredited investors and qualified purchasers defined within the Securities Act of 1933 and the Investment Company Act of 1940. Information provided reflects Sapphire Ventures’ views as of a particular time. Such views are subject to change at any point and Sapphire Ventures shall not be obligated to provide notice of any change. Due to various risks and uncertainties, actual events, results or the actual experience may differ materially from those reflected or contemplated in these statements. While Sapphire Ventures has used reasonable efforts to obtain information from reliable sources, Sapphire makes no representations or warranties as to the accuracy, reliability, or completeness of third party information presented herein. Nothing presented herein may be relied upon as a guarantee or assurance as to the future success of any particular investment opportunity or strategy. Past performance is not indicative of future results.

Dan Gray is a prolific thinker, writer and researcher in the VC world, who describes himself as best known for  “long walls of text on Twitter about the venture industry.” Now the Research Lead at Odin, he sits down with Nick Chirls,  Partner at Asylum Ventures, and Beezer Clarkson, Partner at Sapphire Partners, to discuss the bifurcation of VC, the different types of risk in venture, and the role geography plays in investing. He also unpacks a survey he recently conducted that dives deep into how early-stage VC is faring in a challenging year.Learn more about Sapphire Partners: sapphireventures.com/sapphire-partnersLearn more about OpenLP: openlp.vcLearn more about Asylum Ventures: asylum.vcLearn more about Odin: joinodin.comRead Dan’s Writing on VC: credistick.comRead the Results of Dan’s Survey: credistick.com/lp-2025For a monthly roundup of the latest venture insights, including the newest Origins episodes, subscribe to the OpenLP newsletter – delivered straight to your inbox: subscribe.openlp.vcCHAPTERS:0:00 Welcome to Origins2:16 Unpacking the Early-Stage VC Survey12:27 Who’s Participating Where and When?15:30 The Importance of GP Branding22:19 Dan’s Advice to Early Managers29:47 What the New Normal Looks Like32:20 How Can Smaller Firms Compete?40:34 What Does This Mean for 2026?Origins is produced by Sapphire Ventures in partnership with⁠⁠ Pod People.⁠Nothing presented herein is intended to constitute investment advice, and under no circumstances should any information provided herein be used or considered as an offer to sell or a solicitation of an offer to buy an interest in any investment fund managed by Sapphire Ventures, LLC (“Sapphire”). Any offer or solicitation of securities by Sapphire may only be made in accordance with the current offering documents for a managed Fund in which Sapphire is an advisor. Additionally, Sapphire does not solicit or make its services available to the public; such offerings may only be provided to accredited investors and qualified purchasers defined within the Securities Act of 1933 and the Investment Company Act of 1940. Information provided reflects Sapphire Ventures’ views as of a particular time. Such views are subject to change at any point and Sapphire Ventures shall not be obligated to provide notice of any change. Due to various risks and uncertainties, actual events, results or the actual experience may differ materially from those reflected or contemplated in these statements. While Sapphire Ventures has used reasonable efforts to obtain information from reliable sources, Sapphire makes no representations or warranties as to the accuracy, reliability, or completeness of third party information presented herein. Nothing presented herein may be relied upon as a guarantee or assurance as to the future success of any particular investment opportunity or strategy. Past performance is not indicative of future results.

2025 was, undoubtedly, the year of AI. In the first episode of 2026 Beezer Clarkson, Partner at Sapphire Partners, and Nick Chirls, Partner at Asylum Ventures revisit some of their favorite moments from the year before to see what the top voices in VC saw as emerging AI trendlines and how the venture ecosystem and global markets might respond next. In this episode we’ll hear from – among others – Sarah Tavel of Benchmark about what it means to be truly AI native, Sunil Dhaliwal & Mike Dauber of Amplify about finding technical VCs in the age of AI, and Micah Rosenbloom of Founder Collective on how early stage venture often misses major trends like AI until it’s too late.Learn more about Sapphire Partners: sapphireventures.com/sapphire-partnersLearn more about OpenLP: openlp.vcLearn more about Asylum Ventures: asylum.vcLearn more about Benchmark: benchmark.comLearn more about Amplify: amplifypartners.comLearn more about Founder Collective: foundercollective.comLearn more about Curie.Bio: curie.bioRead Sarah’s Substack Posts: sarahtavel.comCHAPTERS:0:00 Welcome to Origins3:36 Being AI Native with Sarah Tavel10:36 Finding Technical Founders with Mike Dauber & Sunil Dhaliwal14:31 Early Stage Founders Are 7 Years Too Late with Micah Rosenbloom23:04 What AI CAN’T Do with Zach Weinberg28:37-Technical vs. Product Genius with Sarah Tavel38:49 Nick & Beezer’s AI Trends to Watch In 2026For a monthly roundup of the latest venture insights, including the newest Origins episodes, subscribe to the OpenLP newsletter – delivered straight to your inbox: subscribe.openlp.vcOrigins is produced by Sapphire Ventures in partnership with⁠ Pod People.Nothing presented herein is intended to constitute investment advice, and under no circumstances should any information provided herein be used or considered as an offer to sell or a solicitation of an offer to buy an interest in any investment fund managed by Sapphire Ventures, LLC (“Sapphire”). Any offer or solicitation of securities by Sapphire may only be made in accordance with the current offering documents for a managed Fund in which Sapphire is an advisor. Additionally, Sapphire does not solicit or make its services available to the public; such offerings may only be provided to accredited investors and qualified purchasers defined within the Securities Act of 1933 and the Investment Company Act of 1940. Information provided reflects Sapphire Ventures’ views as of a particular time. Such views are subject to change at any point and Sapphire Ventures shall not be obligated to provide notice of any change. Due to various risks and uncertainties, actual events, results or the actual experience may differ materially from those reflected or contemplated in these statements. While Sapphire Ventures has used reasonable efforts to obtain information from reliable sources, Sapphire makes no representations or warranties as to the accuracy, reliability, or completeness of third party information presented herein. Nothing presented herein may be relied upon as a guarantee or assurance as to the future success of any particular investment opportunity or strategy. Past performance is not indicative of future results.

Origins host Beezer Clarkson,  LP at Sapphire Partners and co-founder of OpenLP, and Nick Chirls, GP at Asylum Ventures, dig into their recent conversation with Micah Rosenbloom, Managing Partner at Founder Collective. They discuss the EQ and self-awareness required to switch from operator to investor, how to separate signal from noise in venture cycles, and how the speed of iteration is now such that a window of one or two days can change the entire calculus of an investment.Learn more about Sapphire Partners: sapphireventures.com/sapphire-partnersLearn more about OpenLP: openlp.vcLearn more about Asylum Ventures: asylum.vcLearn more about Founder Collective: foundercollective.comFor a monthly roundup of the latest venture insights, including the newest Origins episodes, subscribe to the OpenLP newsletter – delivered straight to your inbox: subscribe.openlp.vcCHAPTERS:0:00 Welcome to Origins0:34 How Involved Should Operators Be With Their CEOs?2:16 VCs and Trends Are Seven Years Too Late3:19 Repeat Portfolio Companies: Courageous Or Insane?5:42 How Do VCs Handle the Speed of Iteration?Origins is produced by Sapphire Ventures in partnership with⁠⁠ Pod People.⁠Nothing presented herein is intended to constitute investment advice, and under no circumstances should any information provided herein be used or considered as an offer to sell or a solicitation of an offer to buy an interest in any investment fund managed by Sapphire Ventures, LLC (“Sapphire”). Any offer or solicitation of securities by Sapphire may only be made in accordance with the current offering documents for a managed Fund in which Sapphire is an advisor. Additionally, Sapphire does not solicit or make its services available to the public; such offerings may only be provided to accredited investors and qualified purchasers defined within the Securities Act of 1933 and the Investment Company Act of 1940. Information provided reflects Sapphire Ventures’ views as of a particular time. Such views are subject to change at any point and Sapphire Ventures shall not be obligated to provide notice of any change. Due to various risks and uncertainties, actual events, results or the actual experience may differ materially from those reflected or contemplated in these statements. While Sapphire Ventures has used reasonable efforts to obtain information from reliable sources, Sapphire makes no representations or warranties as to the accuracy, reliability, or completeness of third party information presented herein. Nothing presented herein may be relied upon as a guarantee or assurance as to the future success of any particular investment opportunity or strategy. Past performance is not indicative of future results.

Micah Rosenbloom is a Managing Partner at Founder Collective, a firm dedicated to seed investing and, crucially, to keeping their fund sizes below $100 million. Micah talks with Beezer Clarkson, Partner at Sapphire Partners, and Nick Chirls, Partner at Asylum Ventures, to discuss Founder Collective’s philosophy of keeping their fund size small to avoid the “billions or bust” mentality, how most investors have a bad track record of spotting trends at seed, and how consumer goods are still worthwhile investments even against the backdrop of AI. They also debate a recent post from Nick to get to the fundamental question of whether investors taking big risks are courageous or lucky.Learn more about Sapphire Partners: sapphireventures.com/sapphire-partnersLearn more about OpenLP: openlp.vcLearn more about Asylum Ventures: asylum.vcLearn more about Founder Collective: foundercollective.comFor a monthly roundup of the latest venture insights, including the newest Origins episodes, subscribe to the OpenLP newsletter – delivered straight to your inbox: subscribe.openlp.vcCHAPTERS:0:00 Welcome to Origins2:16 What Can Small Do For You?8:57-A Whole Team of Ex Operators14:52 How Micah’s View of the Market Has Changed18:48-Why the Market’s Tough Right Now21:49 Early Stage VCs Are Usually Seven Years Too Late30:14 Investing: Courage or Luck?42:59-Predictions for 2026Origins is produced by Sapphire Ventures in partnership with⁠⁠ Pod People.⁠Nothing presented herein is intended to constitute investment advice, and under no circumstances should any information provided herein be used or considered as an offer to sell or a solicitation of an offer to buy an interest in any investment fund managed by Sapphire Ventures, LLC (“Sapphire”). Any offer or solicitation of securities by Sapphire may only be made in accordance with the current offering documents for a managed Fund in which Sapphire is an advisor. Additionally, Sapphire does not solicit or make its services available to the public; such offerings may only be provided to accredited investors and qualified purchasers defined within the Securities Act of 1933 and the Investment Company Act of 1940. Information provided reflects Sapphire Ventures’ views as of a particular time. Such views are subject to change at any point and Sapphire Ventures shall not be obligated to provide notice of any change. Due to various risks and uncertainties, actual events, results or the actual experience may differ materially from those reflected or contemplated in these statements. While Sapphire Ventures has used reasonable efforts to obtain information from reliable sources, Sapphire makes no representations or warranties as to the accuracy, reliability, or completeness of third party information presented herein. Nothing presented herein may be relied upon as a guarantee or assurance as to the future success of any particular investment opportunity or strategy. Past performance is not indicative of future results.

Origins host Beezer Clarkson,  LP at Sapphire Partners and co-founder of OpenLP, and Nick Chirls, GP at Asylum Ventures, dive into their recent conversation with Kyle Samani, Founder and Managing Partner of Multicoin Capital. They discuss their learnings on crypto, including why Nick is more bullish on bitcoin than Kyle, and how LPs conceptualize investing in firms like Multicoin. They also break down why people who came up as Crypto traders and investors are uniquely positioned to excel in early stage venture.Learn more about Sapphire Partners: sapphireventures.com/sapphire-partnersLearn more about OpenLP: openlp.vcLearn more about Asylum Ventures: asylum.vcLearn more about Multicoin: multicoin.capitalFor a monthly roundup of the latest venture insights, including the newest Origins episodes, subscribe to the OpenLP newsletter – delivered straight to your inbox: subscribe.openlp.vcCHAPTERS:0:00 Welcome to Origins1:02 Is Bitcoin an Unproductive Asset?1:56 The Problem With Web3.03:49 Assessing Crypto Managers As an LP6:21 The Hard Part Isn’t Buying Bitcoin, It’s Holding It8:21 Trained In Crypto, Excelling In Traditional MarketsOrigins is produced by Sapphire Ventures in partnership with⁠⁠ Pod People.⁠Nothing presented herein is intended to constitute investment advice, and under no circumstances should any information provided herein be used or considered as an offer to sell or a solicitation of an offer to buy an interest in any investment fund managed by Sapphire Ventures, LLC (“Sapphire”). Any offer or solicitation of securities by Sapphire may only be made in accordance with the current offering documents for a managed Fund in which Sapphire is an advisor. Additionally, Sapphire does not solicit or make its services available to the public; such offerings may only be provided to accredited investors and qualified purchasers defined within the Securities Act of 1933 and the Investment Company Act of 1940. Information provided reflects Sapphire Ventures’ views as of a particular time. Such views are subject to change at any point and Sapphire Ventures shall not be obligated to provide notice of any change. Due to various risks and uncertainties, actual events, results or the actual experience may differ materially from those reflected or contemplated in these statements. While Sapphire Ventures has used reasonable efforts to obtain information from reliable sources, Sapphire makes no representations or warranties as to the accuracy, reliability, or completeness of third party information presented herein. Nothing presented herein may be relied upon as a guarantee or assurance as to the future success of any particular investment opportunity or strategy. Past performance is not indicative of future results.