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“We’re going into a world where there will be an increase in inequality in terms of the have’s versus have-not’s. And so if you are invested in some of the have’s, I would actually bet on their acceleration of value aggregation in the later stages of scaling which is why I, personally, think a winning strategy is to hold onto them for as long as possible." Charlotte Zhang from Inatai Foundation is back! And if you've tuned into her first episode on Superclusters, you'll know exactly why. Charlotte has been one of my favorite guests on the podcast, marrying both her profound ability for deep analysis with strong framework-oriented assessments. You might remember her 4 P's to underwriting every manager from our prior episode. Naturally I had to have her back for an El Pack episode 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. 99VC's Lisa Yu asks about what LPs look for in Fund I's beyond track record. Escape Velocity's Mahesh Ramakrishnan asks about recycling and what happens when you have 30% of your fund size as distributions in the first few years of the fund. Founder Embassy's Helena Gagern asks about investing in AI frontier labs where the first round of financing already puts the company at $400M+ in valuation. And also, how do you communicate to LPs that you have an "exceptionalism" bucket to invest out of? As the director of investments at Inatai Foundation, Charlotte Zhang oversees the selection of external investment managers, conducts portfolio research, and helps to institutionalize processes, tools, and resources. She previously served as a senior associate at ICONIQ Capital and, before that, Medley Partners. When not working, you can find her globetrotting (18 countries and counting), writing a Yelp review about the best bite in town, or cuddling up with a book and her two adorable cats. You can find Charlotte on her LinkedIn here: LinkedIn: https://www.linkedin.com/in/charlotterzhang/ OUTLINE: (00:00) Intro (01:04) What's new in Charlotte's life? (04:06) LPs Charlotte would love to meet (05:41) Who is Lisa and 99VC? (09:31) What qualities does Charlotte look for beyond track record? (14:55) How does a GP know if they have a differentiated strategy? (15:49) Charlotte's pet peeve (17:29) The bottoms up exercise of building a fund strategy (18:00) Consistency of execution (20:05) The highest level of signal you can get from a founder reference (22:18) The ask (22:51) Who is better at bowling: Mahesh or David? (24:44) Who is Mahesh and Escape Velocity? (25:20) Why is Escape Velocity spelled as EV^3? (27:10) What happens when you have 30% DPI in the first 2 years of your fund? (30:19) Does early DPI matter more in Fund I than Fund III? (33:26) Should you sell secondaries at the Series B as a pre-seed/seed GP? (37:34) Venture is under siege for no DPI (38:18) Would Charlotte rather have 4X in 10 years or 7X in 15 years? (39:42) Have's and have-not's (40:35) Who is Helena and Founder Embassy? (44:45) What is Charlotte's reaction when a pre-seed GP invests in a $400M post valuation? (49:23) How do the best GPs communicate betting off-thesis? (50:44) How many GPs have an "exceptionalism" bucket to invest out of? (55:56) How much underwriting goes into a GP breaking the rules? (58:10) "A-players are obvious" but what isn't? (1:00:38) Charlotte's last piece of advice for LPs (1:03:43) Charlotte's last piece of advice for GPs (1:07:18) Why you should talk about the anti-portfolio (1:09:33) David's favorite moment from Charlotte's previous episode Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters For Superclusters After Hours: https://superclusterslp.substack.com/ Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

“How you modulate a good story is by inserting dopamine, oxytocin, serotonin, and endorphins at the right times to be able to deliver that story so that the person listening to that story can form an opinion.” Asher Siddiqui from the Song Family Office joins me 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. Inuka Capital's Gautam Shewakramani asks about what GPs typically overshare and under-share when they're pitching an LP. As well as how an LP identifies if a GP has great sourcing if they're a generalist fund. Unshackled Venture's Manan Mehta asks if VC is still only one asset class. Is early stage now a combination of discovery and validation capital? Keymaker VC's Tim Wang asks what do most LPs overvalue in GPs. Asher Siddiqui is a global tech investor, M&A dealmaker, and venture fund builder with over 25 years of hands-on experience across venture capital, entrepreneurship, and more than $15B in executed M&A transactions. He began his career as a software engineer and entrepreneur in the US and UK before spending a decade leading M&A and corporate venture at Etisalat Group (now e& Group), one of the world’s largest listed TMT investment groups. There, he led acquisitions, exits, and strategic transactions across multiple continents. In 2016, Asher joined the global leadership team at 500 Startups in San Francisco, helping scale the platform to $2B+ AUM, with a portfolio that includes 35+ unicorns and 160+ centaurs. Since then, he has helped launch and scale several institutional VC firms—including Race Capital, Lumikai, Sukna Ventures, Zayn VC, and Humanrace Capital—and serves on the advisory boards of funds such as FootPrint Coalition Ventures, Merus Capital, and The Treasury. To date, Asher has made 100+ venture investments (both direct and LP), raised hundreds of millions in LP commitments, mentored hundreds of emerging VC managers globally, and advised countless founders. You can find Asher on his socials here: LinkedIn: https://www.linkedin.com/in/ashersiddiqui/ X / Twitter: https://x.com/ashercdkey OUTLINE: (00:00) Intro (02:09) The DOSE framework for underwriting pitches (04:19) Asher's new role (05:38) Who is Gautam and Inuka Capital? (09:19) What do most GPs overshare and undershare on? (15:19) How does Asher differentiate sourcing ability in generalist funds? (20:01) The first date analogy (22:38) What emotions do each of DOSE represent? (27:23) Too much dopamine, not enough endorphins (30:02) Who is Manan and Unshackled Ventures? (31:33) Unshackled's most recent big win (32:46) Discovery capital vs validation capital (33:31) Is venture still only one asset class? (43:29) The Song Family Office portfolio construction (51:41) Asher's stance on reserves (55:00) Why it makes sense to go to zero AGMs (56:23) The ask (57:27) Who is Tim and Keymaker VC? (58:45) What do most LPs overvalue in GPs? (1:04:40) A new way to share the team's personality on the deck? (1:08:09) Asher's last piece of advice (1:14:57) David's favorite moment of Asher in S5 Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters For Superclusters After Hours: https://superclusterslp.substack.com/ Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

“The question at Fund IV is, ‘Okay, you’ve proved that you’re a great firm builder. Congratulations, you’re raising Fund IV. Are you still a great investor?’” Zach Ruchman joined HB Wealth in 2025 as a Shareholder after working with WMS Partners since 2023. In his role as Managing Director, Private Markets, Zach leads the team responsible for research and due diligence of private market investment opportunities across a variety of asset classes, including private equity, growth equity, venture capital, private credit, infrastructure, and real assets. Before joining HB Wealth, Zach was a Senior Vice President at RockCreek and a Vice President at BlackRock, where he led direct co-investment transactions as well as manager research for both primary and secondary commitments in the Americas, Europe, and Asia on behalf of both institutional and family office clients. He began his career as a consultant with Alvarez & Marsal. In this episode, we also talk about how he worked out of the National Democratic Institute's DC office writing grants and tracking political regimes in the Middle East, including the Arab Spring. In the community, Zach serves as a member of the finance committee for the Howard and Geraldine Polinger Family Foundation. You can find Zach on his socials here: LinkedIn: https://www.linkedin.com/in/zruchman/ X / Twitter: https://x.com/zmrphoto OUTLINE: (00:00) Intro (03:04) When 9/11 entered Zach's life (12:20) Interest in the Middle East (15:00) Returning to the US (17:49) What's in the foreign service exam? (22:29) From pursuing the state department to consulting (25:39) Consulting to allocating (32:20) Business school and mentors (36:34) The ask (37:07) How Zach makes re-up decisions? (40:15) The difference between a Fund I and Fund IV (43:26) Alignment between senior and mid-level investors (45:33) Deal attribution at big VCs (46:40) Questions to ask to references to find deal attribution (49:12) Avoiding a reference's scripted answer (52:14) Top 1% performers leaving organizations (53:45) The hardest Fund I to underwrite (1:00:57) Does radical transparency work? (1:06:15) "Private assets work best when they're inefficient." (1:09:20) Does AI change VC investing? (1:11:33) Sourcing that AI cannot do (1:14:26) Can AI write good memos? (1:19:11) Pattern vs exception recognition (1:25:03) An example of how a GP proved he worked hard (1:28:00) Best advice for action photography Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters For Superclusters After Hours: https://superclusterslp.substack.com/ Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

“Our best GPs are talking to their founders all the time. And our best GP relationships, we talk to all the time.” — Apurva Mehta “If you can’t handle something going to zero, then you shouldn’t do one.” — JD Montgomery 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/ 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 (01:53) How did this episode come to be? (06:56) What do LPs get right/wrong with co-invests? (12:06) GP best practices for co-investments (14:35) How do you know a GP is capable of pre-empting a round? (16:37) How often should GPs be talking to their portfolio founders? (17:52) Why Apurva goes to AGMs (18:17) How Apurva/JD stays in touch with GPs (23:33) The ask (24:01) Solo GPs (31:42) Types of solo GPs who join multi-stage firms later (34:32) What's the skew in the benchmarking data? (39:22) What lawyers don't tell you about carveout capital in LPAs (44:46) LPA terms that LPs redline (45:44) Carry ratchets that LPs hate (48:15) How higher fees impact IRR (49:39) Outlandish fees on SPVs (50:49) How much should a GP's salary be? (52:56) Cashless GP contributions (53:59) Do $1T outcomes change venture math? (59:17) Should private market investors be public market investors? (1:04:30) What made Apurva nervous? What does he love? (1:07:57) What does JD love? Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters For Superclusters After Hours: https://superclusterslp.substack.com/ Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

"In private equity, some of the older tricks about just picking on more leverage are not going to work as well now because rates are higher. We need to have more focus on operational improvement and margin expansion. And in venture, you’re not expected to have good margins.” — Julia Rees Toader Julia Rees Toader is the Founding Partner of PrinCap, an independent investment portfolio strategy firm working with institutions and individuals on manager selection, asset allocation, and strategic advisory. Prior to PrinCap, she was the Head of Portfolio Strategy and Head of Relationship Management at Heritage Holdings, a multi-family office. Before Heritage, Julia was the head of Portfolio Strategy at Goldman Sachs Asset Management ($3Tr assets under supervision). She and her team advised sovereign wealth funds, pensions, financial advisory firms, private banks, and other long-term asset owners on asset allocation. She studied mechanical engineering and computer science at Princeton University and is a CFA charterholder. Before Goldman Sachs, she worked on M&A and business development for an early-stage medical device biotech firm. You can find Julia on her socials here: LinkedIn: https://www.linkedin.com/in/julia-rees-toader-cfa-22871030/ OUTLINE: (00:00) Intro (01:38) A 'happy accident' at 16 (04:03) Julia's first startup experience (06:32) Why did Julia join Goldman Sachs? (07:30) When did Julia's appreciation for finance start? (08:05) Conversations around the Rees and Toader dinner table (09:48) Finance vs mechanical engineering (13:26) On exceptional talent (15:18) How to keep a cool head when you're successful (20:19) Do small emerging managers outperform? (22:27) How do you know if a GP is founder-friendly? (23:39) The bad pitch meeting (25:00) Value adds in PE vs VC (29:49) Difference between PE vs VC portfolio construction models (31:19) Timelines to return in PE and VC (33:17) Secondaries (34:34) The ethics of continuation vehicles (36:07) The subscription ask (36:40) Are all secondaries created equal? (38:30) What is 10+1+1? (40:32) Hedge funds looking like private market funds (41:16) What do you do when you have $3B? (44:43) What is home country bias? (46:40) How do you know you're overweighted on allocation? (47:15) The endowment effect in secondaries (48:32) Leaderless investment committee sessions (49:52) The merits of GP stakes (54:10) Why private credit is interesting (56:21) The duration of GP stakes (57:36) The duration of hedge fund GP stakes (58:11) How much GP stake is worth it? (1:00:33) Hedge funds: How much is a good GP stake? (1:02:00) How much is the max an LP wants to own of a hedge fund? (1:03:12) Tax structuring is another form of alpha (1:06:52) Cheetos Pelotazos (1:09:15) Advice to women in finance (1:12:28) Post-credit scene: Age of Empires, Starcraft, and Zelda Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters For Superclusters After Hours: https://superclusterslp.substack.com/ Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

“GPs over-index on how that value-add ties into a portfolio strategy.” — Stacey Kline Stacey Kline and Ben Gallacher are co-founders of February Capital, a fund-of-funds dedicated to providing access to the best in venture. Prior to starting February, they've each held roles as professional athletes, corporate lawyers, startup founders, emerging managers themselves, family office allocators, just to name a few. We spend much of this episode talking about their backgrounds that led them to where they are today, but also on why Stacey and Ben spend so much time underwriting emerging managers' value-adds, as well as their controversial take on it. You can find Stacey on her socials here: LinkedIn: https://www.linkedin.com/in/staceykline/ You can find Ben on his socials here: LinkedIn: https://www.linkedin.com/in/benjamingallacher/ OUTLINE: (00:00) Intro (04:03) Why did it take 22 months to set up fund of funds in Canada? (07:22) Toughest moments when building February Capital (10:12) How did Ben know he wanted to be an LP? (12:58) How did Stacey know she wanted to be an LP? (16:53) The doctor's advice no one expected (18:32) Ben's first NO from Stacey (23:06) Why is it called February Capital? (23:58) What is the role of the LP today? (27:59) What Ben and Stacey look for in GPs (31:08) When does non-consensus thinking lead to portfolio divergence? (36:28) How much portfolio overlap is fair for February? (39:31) How large is February's portfolio? (43:17) Picking an ecosystem vs picking an investor (46:24) What types of GPs did Stacey change her mind on? (47:56) Underwriting a GP's story (49:44) Stacey's controversial take on value-adds (53:07) Why value-adds affect sourcing (57:10) Examples of negative value-add (59:19) Refreshing your value add (1:03:36) An example of when GP and founder incentives are misaligned (1:05:12) The February Capital OS you don't see Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters For Superclusters After Hours: https://superclusterslp.substack.com/ Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

“To whom much is given, much is expected.” — 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 (02:00) The definition of family offices (03:01) Generation 1 vs 2 (06:25) Building a family office at Gen 1 (07:48) The 3 considerations for succession planning (11:14) The "why" of succession planning (12:59) Building self-esteem in children (17:14) How do you help children choose their long-term passions? (20:16) When should next gen of family offices know how rich they are? (23:35) How do next gen family office members first get exposure to VC? (32:25) When do you give next gens influence over the family's capital? (35:28) What % of the family capital should you give a next gen? (37:42) The ask (38:09) The hard and soft issues of wealth (42:41) How often do next gens inherit their parents' support system? (46:35) How does a GP know how sophisticated an FO is? (53:43) How does an advisor know an FO's sophistication? (59:10) Sophisticated simplicity (59:50) When's the last time JD's OS changed? (1:05:23) Post-credit scene: Time is a construct Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclustersFor Superclusters After Hours: https://superclusterslp.substack.com/ Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

“Lower barriers to entry doesn’t mean higher probabilities of success.” — Sam Huleatt Sam Huleatt is the co-founder of The Side Letter, a platform driving network-based research for capital allocators. Prior to The Side Letter, he created and ran the The LP Institute at VC Lab, as well as let On Deck Angels at On Deck. Moreover, he's a serial founder, active angel investor in over 35 companies, and an active allocator in emerging fund managers, including the likes of Notation Capital, Orange Fund, Inuka Capital, Asylum Capital, and more. You can find Sam on his socials here: LinkedIn: https://www.linkedin.com/in/samhuleatt/ X / Twitter: https://x.com/samhuleatt OUTLINE: (00:00) Intro (01:34) Sam's childhood (03:24) The most persistent myth about Sam he never bothered to correct (05:47) Bottom-up vs top-down investor (13:37) Can career VCs develop empathy for the founder (18:43) Traits of someone who should definitely start a fund (26:45) Traits of someone who should NEVER start a fund (28:09) Air of inevitability (33:44) Why was Outlander VC inevitable? (36:11) Where should 60% of your Fund I capital come from? (41:47) Starting a VC fund is hard (44:46) Do LPs like GP accelerators? (51:35) Top 3 considerations for first-time LPs (58:03) How many GPs should 1st-time LPs meet? (1:01:06) Governing law of VC: Adverse selection (1:04:40) Incentive alignment on fees (1:06:36) Terms in LPAs vs side letters (1:11:16) What is The Side Letter? Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters For Superclusters After Hours: https://superclusterslp.substack.com/ Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

“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 Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters For Superclusters After Hours: https://superclusterslp.substack.com/ Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

“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 Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

“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 Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

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 Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

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 Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

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 Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP

"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 Follow David Zhou for more Superclusters content: For podcast show notes: https://cupofzhou.com/superclusters Follow David Zhou's blog: https://cupofzhou.com Follow Superclusters on X: https://x.com/SuperclustersLP