"The limiting downside is actually something a lot of emerging managers don’t think about. If you can turn all of your portfolio companies that don’t hit that exit velocity, if you can find a soft landing for those companies versus that’s a writeoff and they’re dead and done, that’s extra effort, but that’s an extra turn on your fund’s performance." — Carson Monson

Carson Monson is a seasoned allocator with nearly a decade of experience backing emerging and spinout GPs across large institutions, government entities, and family offices. After stints at Greenspring, SITFO, and building a fund of funds strategy for a large European single family office, he now runs the fund of funds at CrossRange, which focuses on supporting top-tier emerging and spinout GPs.

Carson has backed everything from micro funds to high-profile managers spinning out of tier-one firms. He is deeply committed to being a thought partner and strategic resource to the GPs he supports, helping them navigate the complexities of fund building and long-term success in the VC industry.

You can find Carson on his socials here:

LinkedIn: https://www.linkedin.com/in/carson-k-monson/

X / Twitter: https://x.com/Monsson_

OUTLINE:

[00:00] Intro

[02:08] Wildlife and wholesome trouble

[06:03] The journey to being an LP

[10:54] How did Carson join Greenspring?

[13:55] Lessons across Greenspring

[15:46] How many deals did Greenspring do per year?

[18:46] An example of a qualitative metric worth measuring

[20:16] How many off-thesis bets is a VC allowed to make?

[21:25] When do GPs move from thematic bets to opportunistic bets?

[25:45] How much AUM should any one GP have?

[29:46] Why does Carson liked concentrated portfolios?

[30:32] The case for concentrated portfolios

[36:40] Relationships with GPs should stay at the LP partner level

[39:49] Fund strategy at Fund (n) vs Fund (n + 1)

[45:19] What the hell is 'critical node theory?'

[49:54] Examples of great references

[52:58] The halo effect of mega funds

[58:48] How does Carson get to inbox zero

[1:02:09] Why is CrossRange different?

[1:08:17] The last time Carson had a pinch-me moment

[1:10:17] Carson's ricotta gnocchi

[1:12:28] Post-credit scene: Ramen, gluten, Tokyo, and Tonkatsu Suzuki Pt 2

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“A manager doesn’t generally fit into their ultimate quartile until Year 6.”

Apurva Mehta is the co-founding Managing Partner of Summit Peak Investments, a fund-of-funds that boasts a portfolio of both venture fund investments and direct investments, including the likes of Affirm, Anduril, Airtable, Opendoor, and Wish, just to name a few.

Prior to starting Summit Peak in 2018 with his co-founder, Patrick O'Connor, he previously served as Vice President and Deputy Chief Investment Officer for the Children's Hospital Endowment Portfolio in Fort Worth, Texa. From 2008 to 2011, he was the Director of Portfolio Investments at The Juilliard School in New York City. Apurva began his career in investment consulting and investment banking at Citigroup and Lehman Brothers. He was recognized for his expertise when he was named to aiCIO Magazine’s Top Forty Under Forty in 2012 and 2013 and honored as a Rising Star by Institutional Investor. He holds a BBA in Finance from The George Washington University.

You can find Apurva on his socials here:

LinkedIn: https://www.linkedin.com/in/apurvaamehta/

OUTLINE:

[00:00] Intro

[01:40] Tennis

[02:45] Lehman Brothers' impact on Apurva

[05:28] What AI is missing in investment management

[14:26] Underestimated qualitative metrics that impact a GP's story

[22:10] Building Cook Children's Hospital foundation portfolio from scratch

[30:24] Moving quickly as an LP

[31:32] What does Apurva look for in the first meeting?

[37:20] Ugly sweater Christmas parties

[39:56] Apurva's favorite ugly sweaters over the years

[41:40] Post-credit scene: What does GFW mean?

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“It’s a mathematical reality that the highest performing GPs in this part of the market often also have the highest kill rates, which means some things are incredible and other things are super wonky and you have to be cool with that. You can’t be doing a six across the board.” — Caroline Toch Docal

Caroline Toch Docal backs early stage fund managers as the lead of BCV’s Emerging Manager Program. She believes in investing in funds as early as the first close, which is a rare focus in the LP landscape. She’s a lifelong early stage enthusiast from her time at Venture for America to Techstars to Chief to Dorm Room Fund to now Bain Capital Ventures, where she runs the emerging manager program there which has seen quite the evolution since 2017.

You can find Caroline on her socials here:

LinkedIn: https://www.linkedin.com/in/carolinetoch/

X / Twitter: https://x.com/carolinetoch

OUTLINE:

[00:00] Intro

[01:33] BCV Emerge

[02:30] The 13-year summer camp experience

[07:46] From VC to LP

[09:50] Compare/contrast early stage investing to emerging GP investing

[12:51] Behind the scenes of Caroline chose to become an LP

[14:36] Caroline's first investment

[16:24] What is a GP-friendly diligence process?

[21:27] How Caroline pre-qualifies an investment?

[24:50] Understanding if a GP REALLY believes VC is their life's work

[26:25] Examples of long-term language

[31:05] The 3 Acts of BCV's Emerging Manager program

[36:44] What the hell is BGH?

[38:03] Stand up comedy

[39:20] Dogs vs cats

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“The intuition part comes from activities of creativity that change your perspective.” — Yiwen Li

Yiwen 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 scene

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“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 Spurlin

Trish 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/trishdigi

OUTLINE:

[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?

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“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 Miller

Jacob 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?

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“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 Sippel

Eric 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?

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Adam Marchick from Akkadian Ventures joins David on El Pack to answer your questions on how to build a venture capital fund. We bring on 3 GPs at VC funds to ask 3 different questions.

Cocoa VC's Carmen Alfonso Rico asks what belief Adam held firmly for years but changed his mind recently on.

Good Trouble Ventures' AJ Thomas asks about how GPs can better communicate risk to first-time LPs.

1517 Fund's Danielle Strachman asks about the world view Adam has that shapes his investing thesis.

Over the past twenty years, Adam Marchick has had unique experiences as a founder, general partner (GP), and limited partner (LP). Most recently, Adam managed the venture capital portfolio at Emory’s endowment, a $2 billion portfolio within the $10 billion endowment. Prior to Emory, Adam spent ten years building two companies, the most recent being Alpine.AI, which was acquired by Headspace. Simultaneously, Adam was a Sequoia Scout and built an angel portfolio of over 25 companies. Adam was a direct investor at Menlo Ventures and Bain Capital Ventures, sourcing and supporting companies including Carbonite (IPO), Rent The Runway (IPO), Rapid7 (IPO), Archer (M&A), and AeroScout (M&A). He started his career in engineering and product roles at Facebook, Oracle, and startups.

You can find Adam on his socials here:

X / Twitter: https://x.com/adammStanford

LinkedIn: https://www.linkedin.com/in/adammarchick/

And huge thanks to Carmen, AJ, and Danielle for joining us on the show!

OUTLINE:

[00:00] Intro

[01:22] The anatomy of a good story

[02:26] The job of an annual summit

[05:35] How often does VC change?

[07:25] Narratives LPs are looking for at GPs' AGMs

[08:25] "20% overall revenue growth in the portfolio is NOT exciting"

[09:01] What founders talk about at an AGM

[14:01] How does Adam spend time at an AGM

[17:48] Enter Carmen and Cocoa VC

[19:35] What did Adam change his mind about

[21:09] How does an LP assess GP NPS?

[22:16] Picking on-sheet references

[24:33] The origin of Cocoa VC

[26:08] What is Carmen's superpower?

[27:09] What does Carmen want from her LPs?

[29:09] The best answers to "what do you want from your LPs?"

[31:29] Controversial decisions for the LPAC

[33:39] Enter AJ and Good Trouble Ventures

[34:25] Communicating risk to your LPs

[35:58] What about to first-time LPs?

[38:06] Where do first-time LPs come from?

[39:50] What inspired AJ's question?

[42:14] Is the convo different if LPs reach out vs you reach out?

[43:45] The timing of LP conversations: most frequent vs most important

[45:59] The trust equation

[47:45] How to scale trust with LPs

[51:35] How has GPs built trust with Adam?

[53:29] How often does Adam keep in touch with his GPs?

[56:06] Enter Danielle and 1517 Fund

[58:38] What is Adam's mental model?

[1:01:43] How does Adam define low entry prices?

[1:03:25] Tracking trends as an LP

[1:06:55] 80-20 portfolio construction

[1:10:37] Would 1517's thesis 15 years ago count as market risk?

[1:14:12] Adam's last piece of advice

[1:15:46] Akkadian Ventures and RAISE Global

[1:17:06] David's favorite moment from Adam's earlier episode

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“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 Chandra

Anurag 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/achandra41

OUTLINE:

[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 scene

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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/beezer232

LinkedIn: 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 1

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