Superclusters - The Emerging LP Podcast

Carson Monson, a partner at CrossRange Investments, blends his passion for wildlife and venture capital insights in this engaging conversation. He shares valuable lessons from his experience at Greenspring, emphasizing the importance of finding ‘soft landings’ for struggling portfolio companies. Carson passionately discusses the advantages of concentrated portfolios and the concept of playing venture like Moneyball, urging managers to focus on getting companies 'on base.' He also highlights the significance of reputation in building long-term fund strategies.

Apurva Mehta, co-founding Managing Partner of Summit Peak Investments, shares his insights on venture fund investments and the importance of board-level transparency. He discusses how younger investors can harness AI while maintaining core investment skills. Apurva dives into the qualitative metrics that matter in evaluating GPs, advocating for deep relationships over brand names. He reflects on his experiences building a venture portfolio from scratch and the swift decision-making processes at endowments. Plus, he shares fun anecdotes about community-building events!

Caroline Toch Docal, Head of the seed fund / Emerging Manager program at Bain Capital Ventures, shares insights from her journey in early-stage investing. She discusses the delicate balance between supporting emerging fund managers and maintaining a rigorous, GP-friendly diligence process. Caroline reveals how her background shaped her values and views on long-term commitment in VC. Plus, she explores the evolution of BCV's Emerging Manager program and even shares her love for comedy and preference for dogs over cats!

“The intuition part comes from activities of creativity that change your perspective.” — Yiwen LiYiwen Li is a seasoned investor with a successful track record of investing in AI, blockchain, and healthcare tech while developing global business partnerships to fast-scale the business.Yiwen is currently Head of Venture Investments at Bayview Development Group, a global family office with diverse exposure public market, private equity, venture, and real estate. Prior, she was a Principal at Alumni Ventures, responsible for end-to-end multi-stage investments focused on blockchain and fintech. She was Director for Corporate Strategy at Masimo (Nasdaq: MASI). She built an innovation pipeline in healthcare connectivity and data analytics. She was Director for Corporate Development at NantHealth (Nasdaq: NH), where she established the international business division. Yiwen started her career at Capital Group in equity research.Yiwen is an Advisory Board member of C-Sweet. She served on the board of Give2Asia as the chairman of the finance committee and a member of the investment committee. She was an advisory board member for the Asia Society where she co-founded the “Asian Women Empowered” initiative. She was recognized as the” Top 50 Women Leaders in San Jose 2024 and 2025”, “Top 50 Women in 2019” and the “Most Inspirational Women in Web 3”. Yiwen is also the author of one of the best sellers “Make the World Your Playground”, inspiring women to find their unique path. She is a frequent speaker on innovation and emerging technology trends.Yiwen holds a Master from the London School of Economics and a Master from the University of Vienna. She also graduated from the Venture Capital program at UC Berkeley and the Private Equity Program at Wharton. She was selected to be one of the " Young American Leaders" at Harvard Business School. Yiwen is a recipient of the European Union’s Erasmus Mundus scholarship. She is fluent in Mandarin and German, worked and lived in Europe, Asia, and US.You can find Yiwen on her socials here:LinkedIn: https://www.linkedin.com/in/yiwenli999/OUTLINE:[00:00] Intro[02:07] Yiwen's childhood[05:00] Jazz singing[06:14] The value of learning languages[09:01] How to build intuition around emerging managers[14:51] Getting to the bottom of a GP's motivation[16:33] What percent of GPs are not in VC for the right reasons?[19:47] Does success fuel or inhibit ambition?[24:17] The cost of knowledge is cheaper[24:56] Competitive edges in the current world[27:06] Why creative activities matter[31:21] Advice to emerging LPs[32:42] Post-credit sceneFollow David Zhou for more Superclusters content:For podcast show notes: https://cupofzhou.com/superclustersFollow David Zhou's blog: https://cupofzhou.comFollow Superclusters on X: https://x.com/SuperclustersLP

“Once you hit a billion dollars, you should probably consider some sort of internal team. Just to mitigate risk. There’s audit risk involved when you have such a small number of people managing a huge pool of capital. It’s going to differ for everyone. That’s probably a good benchmark.” — Trish SpurlinTrish Spurlin is the Investment Director at Babson’s $800M endowment, covering private markets investing with a large focus on venture. In fact 70% of their private equity portfolio is venture capital. Quite a unique strategy for an endowment to take. Why? An endowment is required to provide, in this case, the university money every single year, anywhere from 5% to 60% of a university’s annual budget. And to invest in an illiquid asset class aka venture capital that doesn’t return capital till a decade later, if not longer, takes courage.You can find Trish on her socials here:LinkedIn: https://www.linkedin.com/in/trishspurlin/X / Twitter: https://x.com/trishdigiOUTLINE:[00:00] Intro[01:45] Sports in Trish's life[05:10] How does success fuel inhibit ambition? How does it inhibit ambition?[07:35] How do you underwrite long term motivation?[13:21] How fast you order something might matter[16:04] Can Trish angel invest outside of Babson?[17:08] Endowment with a $80M budget[19:54] Should you hire an outsourced CIO?[24:18] Endowment with a $8B budget[27:47] Babson's liquidity requirements[30:33] How to ask about a senior partner leaving[34:05] How does Trish build trust with her GPs?[37:48] Trish's interests vs Babson's interests[45:24] Hank sauce[47:26] Why is Ocean City Boardwalk special?[48:51] What serves as a reminder to Trish we're still in the good ol' days?Follow David Zhou for more Superclusters content:For podcast show notes: https://cupofzhou.com/superclustersFollow David Zhou's blog: https://cupofzhou.comFollow Superclusters on X: https://x.com/SuperclustersLP

“There’s this thing called alpha, which is returns driven by skill not market return. And when you start to think about what does that mean, skill means you’re doing something that other people aren’t. You have to be different from the average. What can drive that? How are you going to have that be positive expected value? You need to have unique information, unique insight, unique access, or get uniquely lucky." — Jacob MillerJacob Miller is the Co-Founder and Opto’s Chief Solutions Officer, a key figure in its leadership team and central to its growth strategy. He spearheads initiatives for Opto's fiduciary partnerships and the systemization of institutional-quality private markets investment techniques and programs.Before co-founding Opto, Miller spent nearly five years as an investor at Bridgewater Associates. Miller has a passion for sensible long-term investing, systematizing investment processes, and distilling complex market dynamics into clear, logical linkages that help people better understand their investments. Having managed money for family and friends since he was 16, Miller is a certified market junkie. While he has a background in macroeconomics and high-yield debt, he finds the challenges and opportunities in the private markets space far more interesting and important, both for investors and society.You can find Jacob on his socials here:LinkedIn: https://www.linkedin.com/in/jacob-m-08b32967/OUTLINE:[00:00] Intro[01:49] Why did Jacob start investing at 8 years old?[07:20] The fallacies of storytelling[08:49] Inputs, framework, and outputs[09:21] Jake's mental framework for alpha[12:31] Pete Soderling's unique access[13:49] Jacob on defense tech VCs[14:57] How does Jacob underwrite relationships in defense?[16:30] How do you know if someone's been preaching a story before it became a story?[20:16] The difference b/w an opinion and an insight[23:07] Why does Jacob write?[25:42] Running with Joe Lonsdale at 8:30AM[29:12] 2 wildly different billionaires[31:48] What does Jacob want for the world?[36:23] What keeps Jacob humble?Follow David Zhou for more Superclusters content:For podcast show notes: https://cupofzhou.com/superclustersFollow David Zhou's blog: https://cupofzhou.comFollow Superclusters on X: https://x.com/SuperclustersLP

“I hate checklists. I like outlines. I don’t like checklists. A checklist says ‘I have to have this, and then I’m good. An outline is ‘This is my starting point. These are the kinds of things I want to talk about or kinds of things I need to look at.” — Eric SippelEric Sippel currently runs his family office and is an active investor in and adviser to many venture capital, private equity, hedge and real estate funds. He is a member of the RAISE Global selection and steering committees (the premier emerging VC manager conference) and often speaks to emerging venture manager groups. Previously, Eric was the COO of Eastbourne Capital Management, a multi-billion dollar hedge fund firm, and a Partner at Shartsis, Friese & Ginsburg, where he was a nationally recognized hedge fund and venture capital lawyer. Eric serves on more than a dozen LPACs and has served on many for profit and non-profit boards.You can find Eric on his socials here:LinkedIn: https://www.linkedin.com/in/eric-sippel-976770/OUTLINE:[00:00] Intro[02:13] Why Eric's name on LinkedIn is lowercase?[02:44] Oceanside[04:18] Eric's grandfather and education in the family[07:06] Basketball[07:58] Eric's first venture fund investment in 1996[12:05] How does Eric invest below the minimum check size requirement?[14:51] How to decide your LP check size[17:47] Today, when does Eric invest in a new GP?[21:14] Time x capital 2x2 matrix[24:32] Tough conversations with Eric[27:00] The minimum viable value-add for LPs who write small checks[32:02] Eric's most impactful mistakes[35:11] How do you know if a GP is GOOD at adding value?[43:42] How many other funds in the same space does Eric look at before investing?[46:36] Breaking down Eric's deal flow[49:35] How many references does Eric do?[50:27] Who does Eric trust for LP references?[52:34] Other references for diligence[55:23] How does Eric approach a founder reference?[59:09] Biggest lessons from CIA training[1:05:16] Mike's Pizza[1:06:18] If everything were to change tomorrow, what would Eric photograph?Follow David Zhou for more Superclusters content:For podcast show notes: https://cupofzhou.com/superclustersFollow David Zhou's blog: https://cupofzhou.comFollow Superclusters on X: https://x.com/SuperclustersLP

In this engaging discussion, Adam Marchick, seasoned investor and fund manager, delves into shifting beliefs about ownership requirements and how LPs can be effective thought partners. Joining him are Carmen Alfonso Rico, who explores Cocoa VC's founder-first approach, and AJ Thomas, who analyzes communication strategies for first-time LPs. The conversation sheds light on the importance of building trust, the dynamics of sector-specific investments, and the need for clear storytelling in venture funding. A rich dialogue on the evolving landscape of venture capital!

“There are a thousand ways to put lipstick on the pig and there are a thousand skeletons [in the closet]. I’ve only seen five or six because I’ve only seen three startup experiences. And so you need to deputize as many people as you possibly can to essentially triangulate.” — Anurag ChandraAnurag Chandra has spent over two decades in Silicon Valley as an investor, operator, and allocator. He has helped lead four venture capital funds, managing over $2.0B in aggregate AUM. Anurag has also been a senior executive in three enterprise technology startups, two of which were sold successfully to public companies. He is currently the CIO of a single-family office with an attached venture studio and a Trustee for the $4.5B San Jose Federated City Employees Retirement Fund, serving as Vice Chair of the Board, and Chair of its Investment and Joint Personnel Committees.You can find Anurag on his socials here:LinkedIn: https://www.linkedin.com/in/anchandra/X / Twitter: https://x.com/achandra41OUTLINE:[00:00] Intro[02:10] Why is what Anurag is wearing a walking contradiction?[06:08] The man without a home, but comfortable in everyone's home[10:17] The Stanford Review[12:55] The four @%#-holes of America[20:13] How did Anurag schedule regular coffee with Mark Stevens?[25:31] Mark Stevens' advice to Anurag about staying top of mind[26:42] How often should you email someone to stay in touch?[30:33] Why should you be an asymmetric information junkie?[34:21] Where should you find asymmetric information in VC?[36:02] The 'Oh Shit' board meeting[40:09] How San Jose Pension Plan views GPs[43:55] Defining the 'venture business'[49:09] Process drives repeatability[54:06] How San Jose Pension Plan built their investment process from scratch[58:43] What is a risk budget?[1:01:52] What did San Jose Pension Plan do about their risk budget?[1:05:05] The people who changed Anurag[1:11:10] Post-credit sceneFollow David Zhou for more Superclusters content:For podcast show notes: https://cupofzhou.com/superclustersFollow David Zhou's blog: https://cupofzhou.comFollow Superclusters on X: https://x.com/SuperclustersLP

Beezer Clarkson from Sapphire Partners joins David on El Pack to answer your questions on how to build a venture capital fund. We bring on four GPs at VC funds to ask four different questions.Precursor Ventures' Charles Hudson asks what is the one strongly held belief about emerging managers that she no longer believes is true.NextView Ventures' Stephanie Palmeri asks how much should an established firm evolve versus stick to their guns.Humanrace Capital's Suraj Mehta asks what the best way to build brand presence is.Rackhouse Venture Capital's Kevin Novak asks if you've deployed your capital faster than you expected, what's the best path forward with the remaining capital you have left?Beezer Clarkson leads Sapphire Partners‘ investments in venture funds domestically and internationally. Beezer began her career in financial services over 20 years ago at Morgan Stanley in its global infrastructure group. Since, she has held various direct and indirect venture investment roles, as well as operational roles in software business development at Hewlett Packard. Prior to joining Sapphire in 2012, Beezer managed the day-to-day operations of the Draper Fisher Jurvetson Global Network, which then had $7 billion under management across 16 venture funds worldwide.In 2016, Beezer led the launch of OpenLP, an effort to help foster greater understanding in the entrepreneur-to-LP tech ecosystem. Beezer earned a bachelor’s in government from Wesleyan University, where she served on the board of trustees and currently serves as an advisor to the Wesleyan Endowment Investment Committee. She is currently serving on the board of the NVCA and holds an MBA from Harvard Business School.You can find Beezer on her socials here.Twitter: https://twitter.com/beezer232LinkedIn: https://www.linkedin.com/in/elizabethclarkson/Check out Sapphire's latest breakdown on if venture is broken: https://www.linkedin.com/pulse/venture-broken-what-2000-priced-early-stage-rounds-tell-clarkson-sjvjc/And huge thanks to Charles, Suraj, Steph, and Kevin for joining us on the show!OUTLINE:[00:00] Intro[01:22] Where does Beezer's advice come from?[04:03] Charles and Precursor Ventures[04:47] What's something Beezer used to believe about seed stage venture that she no longer believes in[08:04] Why did Charles choose to bet on pre-seed companies?[10:21] What did LPs push back on when Charles was starting Precursor?[12:18] Definition of early stage investing today[14:38] Steph and NextView Ventures[18:13] When do you stick your knitting or move on from the past as an established firm?[30:48] Is venture investing in AI fundamentally different than investing in other types of companies?[32:52] Does competition for a deal mean you've already lost it?[36:09] Suraj and Humanrace Capital[36:54] How should emerging managers build their brand?[38:38] The audience most emerging managers don't focus on but should[40:39] How much does visible brand presence matter?[43:47] Useful or not: Media exposure in the data room[45:40] Backstreet boys[46:37] Kevin and Rackhouse Venture Capital[47:28] What Kevin is best known for[48:03] Updated fund modelling when you're ahead on your proposed deployment period[58:00] The typical questions Beezer gets on LPACs[1:03:22] Is venture broken?[1:06:41] David's favorite Beezer moment from Season 1Follow David Zhou for more Superclusters content:For podcast show notes: https://cupofzhou.com/superclustersFollow David Zhou's blog: https://cupofzhou.comFollow Superclusters on X: https://x.com/SuperclustersLP