“The game you play as you’re building a reputation becomes a different game than when you have a reputation. And I tend to find, from an LP’s perspective, when you’re building reputation, that’s actually when you deliver the most value.” — Alex Felman

Alex Felman is an entrepreneurial and family office professional. For over 10 years, as a second-generation member, he has run his own family office, Felman Family Office, and works with family offices around the world through his family's multifamily group, MSF Capital Advisors. Using his expertise in Molecular Toxicology and Bio-entrepreneurship (B.A from University of California -Berkeley, MBA from Copenhagen Business School), he advises them in biotechnology, healthcare, and other futuristic tech industries with the goal of maintaining long-term wealth through innovation. He regularly speaks at family office and private wealth events on topics such as tech investment, manager selection, generation and succession issues, rising generation trends, and more.

He has used his experience within the family office industry and 20 year background as an educator to create Exponential U, a family office education program designed to help families become multigenerationally sustainable. His proprietary L^3 framework (Learn, Leverage, Legacy) allows the holistic development of family members to ensure a smooth leadership transition.

You can find Alex on his socials here:

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

OUTLINE:

(00:00) Intro

(04:36) The 'tastemaker' for family offices

(05:54) Exploration vs discipline

(08:15) The hero's journey in investing

(09:49) The life line

(13:39) Building and having reputation

(16:06) Risk appetites for asset owners & allocators

(18:44) Why won't an institution invest in me?

(19:50) The quiet thing LPs don't talk about

(25:15) When did Alex get involved with his family office?

(29:09) Writing off sourcing slides

(35:33) Different flavors of "sourcing from YC"

(38:41) Emerging GPs are "investments-as-a-service"

(40:08) Fund power law is greater than startups'

(43:44) Emotional value of investing in funds

(44:45) Most VC funds are scams!

(50:01) Optimistic cynic

(51:43) Reminders today about the good ol' days

(54:17) Late stage capitalism

(59:10) Post-credit scene: Dave Chappelle and podcasts

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“One thing that is unique to private equity and venture capital is persistence is a little easier because of the brand. ‘They did good deals, so therefore, the good deals come to find you.’ If you were in a long-only private equity shop or hedge fund, Amazon is not going to come find you because you invested in Shopify.” — JD Montgomery

JD Montgomery leads the Family Office division at Canterbury Consulting and is a seasoned advisor with nearly four decades of experience serving prominent families with a focus on strategy, organization and measurement. Based in Newport Beach, he serves a select group of multi-generational families and helps them navigate the complexities of wealth, purpose, and legacy. Mr. Montgomery partners with his clients to help them optimize the allocation of their resources across generations. Over the years, Mr. Montgomery has developed a deep network of relationships in the venture capital industry. He has helped his clients gain meaningful exposure to venture funds and direct investments and develop relationships with leading innovators and investors globally. He is a Managing Director, shareholder, and board member at Canterbury Consulting. He graduated from Stanford University and holds the Chartered Alternative Investment Analyst (CAIA) designation.

You can find JD on his socials here:

LinkedIn: https://www.linkedin.com/in/jd-montgomery-6161341b/

OUTLINE:

[00:00] Intro

[02:18] The "some day" exercise

[11:12] Why does JD do "some day" every 6 months?

[12:33] JD's life line

[16:44] When JD is 85 years old...

[18:05] JD's relationship with fatherhood despite the trauma

[22:40] Annual dad report cards

[25:33] Intentionality with GPs

[28:41] How to avoid one-hit wonders

[33:43] How to transfer self-esteem

[36:05] How do you get GPs off of their talk track?

[37:36] Non-obvious things JD looks for in GPs

[41:43] Is selling 0.2X DPI in the first 4 years meaningful?

[44:27] Should you recycle capital or deploy out of the next fund?

[46:34] Why did JD choose to work with families?

[48:07] "Never eat alone"

[51:34] How does JD think about time allocation?

[55:06] How many new GPs does JD meet with?

[59:07] How did JD pass on then back Founders Fund?

[1:03:22] The difference between unexplored gold veins and rotting trash

[1:08:13] Mayan Mocha at Austin's Picnik

[1:08:58] JD's secret street taco recipe

[1:11:09] JD's reminder that we're still in the good ol' days

[1:13:20] Post-credit scene: No garlic and onions

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“You’re making decisions in an incomplete vacuum. What I think many people should do more of, in terms of those mental models, is frame it in the reverse. Which of these decisions am I going to make that is the most regret-minimizing? That I have the least likelihood of regretting later on in life, assuming that in most cases, I will be wrong.” — Peter Walker

The holiday season has always been a great time to celebrate the movers and shakers in our world. This season we're celebrating my personal favorites in the VC and startup world. This episode, it's with my man, Peter Walker, who creates some of the industry's most talked charts and graphics around the ebbs and flows of tech innovation.

Peter Walker runs the Insights team at Carta, where he works to make startups a little less opaque for founders, investors, and employees. Prior to Carta, he was a marketing executive for the media analytics startup PublicRelay and led a data visualization team at The Atlantic magazine. He lives in San Francisco, but you can find him on LinkedIn (see links below).

You can find Peter on his socials here:

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

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

OUTLINE:

[00:00] Intro

[02:52] Peter's first brush with entrepreneurship

[11:49] 996 work culture

[17:11] Peter's disclaimer on his data

[21:27] Regret-minimization when investing

[24:24] One example of regret-minimization

[26:07] How does Peter choose which conferences to go to

[29:33] Conference panels are often bad

[36:22] The incongruencies of what GPs say publicly and privately

[41:43] Peter's first data visualization

[44:18] Why is soccer underrated in the US?

[46:10] What great lengths has Peter gone for his friends?

[48:21] One worrisome trend we're going to see in 2026

[52:18] One optimistic trend to look forward to in 2026

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For podcast show notes: https://cupofzhou.com/superclusters

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Warning: This is a brief-ish, but hopefully entertaining intermission from the usual Superclusters programming.

When we passed the 50th episode mark more than a few episodes ago, Tyler (my editor) and I thought it'd be interesting to record an episode where I change seats. Instead of me asking the questions, someone else would ask me questions. And I couldn't imagine any better person to do so than my good friend, Allie, who in my humble opinion, is one of the best interviewers alive today.

Allie Garfinkle is a senior finance reporter for Fortune, covering venture capital and startups. She authors Fortune’s weekday dealmaking newsletter Term Sheet, hosts the Term Sheet Podcast, and co-chairs Fortune Brainstorm, a community and event series featuring an annual retreat in Deer Valley, Utah. A regular contributor to BBC’s Business Matters podcast, Allie is also a frequent moderator at major conferences such as SXSW. Before joining Fortune, she covered Amazon and Meta at Yahoo Finance and helped produce Emmy-nominated PBS Frontline business documentaries, including Elon Musk’s Twitter Takeover and The Power of the Fed. A graduate of The University of Chicago and New York University, Allie currently resides in Los Angeles.

You can find Allie on her socials here:

LinkedIn: https://www.linkedin.com/in/alexandra-garfinkle1/

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

OUTLINE:

[00:00] Intro

[02:01] Art

[09:39] Competition

[17:49] Paleontology

[18:14] Allie's Tiki mugs

[22:49] How has VC evolved?

[29:41] Evaluating risk

[43:04] Why is it important for VCs to stay in touch?

[47:10] Are there reliably good investors?

[53:09] Young GPs in market

[54:58] How useful is education that come via public talks?

[57:50] Does your niche fund size make sense for the market?

[1:01:16] Is there too much venture capital?

[01:05:24] How much of VC is art vs science?

[1:07:18] What's going on in Allie's world?

[1:09:45] Post-credit scene: Receipts

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For podcast show notes: https://cupofzhou.com/superclusters

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The holiday season has always been a great time to celebrate the movers and shakers in our world. This season we're celebrating my personal favorites in the LP world. To start this mini-holiday series off, Earnest Sweat and Alexa Binns runs one of the most popular podcasts on venture capital limited partners, Swimming with Allocators. I was also fortunate enough to be on their podcast as well as a bonus crossover episode.

You can find Earnest on his socials here:

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

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

You can find Alexa on her socials here:

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

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

OUTLINE:

[00:00] Intro

[02:09] Alexa's earliest relationship with money

[03:28] Earnest's earliest relationship with money

[04:45] Earnest's first major purchase

[06:41] Alexa's first major purchase

[08:25] The difference between public speaking and interviewing

[12:19] Memorable guests on the SwA podcast

[14:46] To do or not to do in-person interviews

[18:05] Evolution of YouTube titles

[20:04] Why err towards evergreen content?

[22:30] Was SwA designed for LPs or GPs?

[24:12] How did Earnest and Alexa meet?

[24:56] How did Swimming with Allocators start?

[27:21] The Pandora's Box of intros

[28:02] Alexa's 3 buckets for LP investing

[30:12] What is 'coming soon' for Earnest and Alexa?

[36:58] Post-credit scene: Spider-Man & Investors as Avengers

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For podcast show notes: https://cupofzhou.com/superclusters

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Ben Choi from Next Legacy 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.

Gilgamesh Ventures' Miguel Armaza, also host of the incredible Fintech Leaders podcast, asks Ben what is the timing of when a GP should consider raising a Fund III.

Similarly, but not the same, Strange Ventures' Tara Tan asks when an LP backs a Fund I, how do they know that this Fund I GP will last till Fund III.

Arkane Capital's Arkady Kulik asks how one should think about building an LP community, especially as he brings in new and different LP archetypes into Arkane's ecosystem.

Ben manages over $3.5B investments with premier venture capital firms as well as directly in early stage startups. He brings to Next Legacy a distinguished track record spanning three decades in the technology ecosystem.

Ben’s love for technology products formed the basis for his successful venture track record, including pre-PMF investments in Marketo (acquired for $4.75B) and CourseHero (last valued at $3.6B). He previously ran product for Adobe’s Creative Cloud offerings and founded CoffeeTable, where he raised venture capital financing, built a team, and ultimately sold the company.

Ben is an alum and Board Member of the Society of Kauffman Fellows (venture capital leadership) and has also served his community on the Board of Directors for the San Francisco Chinese Culture Center, Children’s Health Council, Church of the Pioneers Foundation, and IVCF.

Ben studied Computer Science at Harvard University before Mark Zuckerberg made it cool and received his MBA from Columbia Business School. Born in Peoria, raised in San Francisco, and educated in Cambridge, Ben now lives in Los Altos with his wife, Lydia, three very active sons, and a ball python.

You can find Ben on his socials here:

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

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

OUTLINE:

[00:00] Intro

[05:05] Ben's 2025 Halloween costume

[06:44] Jensen Huang's leather jackets

[07:24] Jensen Huang's answer to Ben's one question

10:05] Enter Miguel, Gilgamesh Ventures, Fintech Leaders

[14:43] What are good signals an LP looks for before a GP raises a Fund III?

[22:35] Why does Ben say 'established' starts at Fund IV?

[25:08] Who's the audience for Miguel's podcast?

[27:52] In case you want more like this...

[28:32] Enter Tara and Strange Ventures

[32:46] How does Ben know a Fund I will become a Fund III?

[36:53] How does Ben know if a GP will want to build an enduring career?

[40:58] How does Tara share a future GP she'd like to work with to Ben?

[42:43] Marriage and divorce rates in America

[43:34] What should a Fund I do to institutionalize?

[46:28] Should you share LP updates to current or prospective LPs?

[48:57] Enter Arkady and Arkane Capital

[51:09] How does one think through LP-community fit?

[1:01:31] What's Arkady's favorite board game?

[1:03:08] Ben's last piece of advice to GPs

[1:09:50] My favorite Ben moment on Superclusters

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For podcast show notes: https://cupofzhou.com/superclusters

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"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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For podcast show notes: https://cupofzhou.com/superclusters

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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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For podcast show notes: https://cupofzhou.com/superclusters

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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

Follow David Zhou for more Superclusters content:

For podcast show notes: https://cupofzhou.com/superclusters

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