Venture Unlocked: The playbook for venture capital managers Samir Kaji

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.
We are back with another LP-focused episode with Michael Kim, Founder of Cendana Capital. Michael shares how he started Cendana around his thesis (at the time very early) of backing small, emerging managers. This led to early investments in firms such as IA ventures, Forerunner, and Lerer Hippeau.
During our discussion, we chatted about what qualities he’s seen in great emerging managers as well as his thoughts on portfolio construction.
We also get into the challenges of raising funds today and why the secondary market will a critical component of venture moving forward.
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About Michael Kim:Michael Kim is the Founder of Cendana Capital, a San Francisco-based firm that specializes in investing in very early-stage VC funds globally. Founded in 2010, Cendana Capital has over $2B in AUM.
Prior to Cendana, Michael served as a General Partner at Rustic Canyon Partners where he contributed to the firm's growth and investment strategies. He also was a Board Member of the San Francisco Employees' Retirement System (SFERS), and an Investment Banker at Morgan Stanley focusing on Technology M&A.
Michael holds an MBA in Finance from The Wharton School, an MSFS in International Economics from Georgetown University's Walsh School of Foreign Service, and an AB in International Relations from Cornell University. Michael is a founding board member of the Wikimedia endowment, which supports Wikipedia.
In this episode, we discuss:
(02:49) Michael’s time at Morgan Stanley's tech M&A group in the 90s
(04:11) Cendana’s launch and how it took two years to raise the first fund
(06:16) Seed stage investing has become like early stage venture.
(07:07) The importance of fund managers getting large ownership early
(09:50) Why grit, determination, and hustle are crucial and domain expertise and contrarian thinking are vital
(12:00) Pre-seed is the new seed and rounds have gotten bigger
(14:00) High integrity fund managers need 12-15% ownership
(16:12) Pre-seed managers work with potential entrepreneurs before they start a company
(18:00) Founders now raise more initially for a longer runway
(20:00) How fund size affects ownership and return potential
(23:00) Why smaller funds often outperform larger ones
(25:17) What changes when making the leap from small to large checks
(27:00) The importance of network strength for fund managers' success
(33:00) Fund managers need to explain their investment decisions well
(37:15) Fund managers need to be flexible but transparent
(39:00) The importance of trust and transparency for long-term relationships.
(42:00) Seed funds are best positioned for secondaries
(45:21) The potential rise in secondary market deals
(48:00) Tourist fund managers have mostly exited the market
(50:00) The next few years should be great for venture investments
I’d love to know what you took away from this conversation with Michael. Follow me @SamirKaji and give me

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.
We are back with Amy Saper, partner at Uncork Capital. Amy shares her journey from Silicon Valley operator at Twitter and Stripe to venture capitalist. She talks about Uncork’s strategy, including its recent $200 million seed fund and $200 million opportunity fund, and how the firm balances growth with specialization.
Investors will find her perspective on non-consensus investing particularly compelling, as she outlines how she evaluates technical teams and market potential. Successful founders attract and develop talent. Finally, she reflects on her move to Uncork and shares her key learnings as an institutional investor.
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About Amy Saper:Amy Saper is a Partner at Uncork Capital, where she invests in seed-stage B2B SaaS, API-first, and fintech companies. Previously, she spent four years as an early-stage partner at Accel where she led seed and Series A investments in companies such as Gamma, Beam, Complete, and Sprinter Health.
Prior to her venture career, she worked at Stripe, Uber, and Twitter launching products, business lines and new markets, in product marketing, product management, business development and international expansion roles.
She received her BS and MBA from Stanford University.
In this episode, we discuss:
(02:27) Amy discusses her background, including her experience at Twitter, Stripe, and her transition to venture capital
(08:00) Joining Uncork Capital, the firm's history, and the recent funds they have raised
(09:14) Comparing the culture of a firm with that of a startup and discusses the importance of sticking to the core focus
(15:17) How Uncork Capital decided on its fund strategy and the balance they struck between fund size and being lead investors
(18:28) Product market fit in Venture firm and how she delivers value to founders
(24:27) How constraints can foster creativity and the importance of staying focused in a capital-constrained market
(28:49) The challenges startups face in raising Series A funding and the importance of balancing focus and growth.
(34:37) Non-Consensus investing and what she looks for in founders
(37:17) The importance of a founder's ability to attract and develop talent and shares her thoughts on whether this can be learned
(42:13) What attracted her to Uncork Capital and how the team dynamics influenced her decision
(45:40) The one thing she knows now that she wishes she knew when she started investing
I’d love to know what you took away from this conversation with Amy. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.
Podcast Production support provided by Agent Bee


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.
Today we have another version of Venture Unlocked shorts, and this time it will be focused on topics within the GP/LP world.
Joining me again is Meghan Reynolds, who leads capital formation at Altimeter Capital. 
This time we discuss the significant liquidity challenges in the venture capital market, focusing on the concerns of LPs about funding future capital calls and the longer wait times for returns. With a decline in public offerings and exits, LPs and GPs are now turning to alternative strategies such as strip sales and GP-led secondaries. We highlight the need for GPs to establish clear liquidity management as the dynamics of the industry continue to change.
If you’re a VC investor, then I’m sure you already know about Sydecar, the go-to platform for emerging VCs to manage their SPVs and funds. Sydecar is on a mission to make private markets more accessible, transparent, and liquid by standardizing how investment vehicles are created and executed. Their powerful software allows VCs to launch SPVs and funds instantaneously, track funding in real time, and offer hassle-free opportunities for early liquidity.
Whether you’re syndicating your first or fiftieth deal, Sydecar acts as your silent operating partner, handling all back-office functions in a single place. Sydecar always has your back, so that you never have to worry about chasing subscription docs, lost wires, or late K-1s.
With all the recent ups and downs in the private markets, the last thing you want to worry about is whether your back office is operating smoothly. Sydecar's responsive and proactive customer support team is there to assist, helping you build trust with your investors and tackle the challenges of building your firm.
Visit sydecar.io/ventureunlocked to learn more.
About Meghan Reynolds:Meghan Reynolds is Partner and Head of VC Capital Formation and Fundraising for Altimeter, a lifecycle technology investment firm. Prior to joining Altimeter, Meghan was Managing Partner and Co-head of Fundraising at TPG. She began her career and spent nearly a decade in the Investment Management Division of Goldman Sachs.
Meghan graduated from the University of Notre Dame.
In this episode, we discuss:
(02:00) The current state of the venture capital market and LP perspectives on liquidity and the impact of market resets on traditional exit opportunities like IPOs and M&As
(04:00) Liquidity and the challenges for LPs in funding upcoming capital calls due to increased venture activity and the need to adjust liquidity timeline expectations
(09:00) The complexities of exit strategies and the necessity for alignment between GPs and LPs on exit timing
(12:57) Using “Strip sales” as a liquidity management strategy are detailed, where a portion of a fund’s assets are sold to secondary buyers, and practical examples of how this strategy has been effectively implemented
(21:56) The need for venture capital to adopt more institutional and LP-friendly practices akin to the private equity evolution post-2008, driven by current fundraising challenges that compel VC funds to innovate in liquidity management and LP relationships
I’d love to know what you took away from this conversation with Meghan. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.
Podcast Production support provided by Agent Bee


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.
This week we're doing another special roundtable discussion with a focus on the seed stage market. Joining us are Jenny Fielding of Everywhere Ventures, Kirby Winfield of Ascend, and Nate Williams of UNION Labs.
This whole conversation was focused on seed stage investing. We spent most of our time discussing how the market reset affects seed-stage decision-making, fund sizing, and reserve strategies. We also touched on what they are seeing and hearing from LPs that invest in seed funds.
If you’re a VC investor, then I’m sure you already know about Sydecar, the go-to platform for emerging VCs to manage their SPVs and funds. Sydecar is on a mission to make private markets more accessible, transparent, and liquid by standardizing how investment vehicles are created and executed. Their powerful software allows VCs to launch SPVs and funds instantaneously, track funding in real time, and offer hassle-free opportunities for early liquidity.
Whether you’re syndicating your first or fiftieth deal, Sydecar acts as your silent operating partner, handling all back-office functions in a single place. Sydecar always has your back, so that you never have to worry about chasing subscription docs, lost wires, or late K-1s.
With all the recent ups and downs in the private markets, the last thing you want to worry about is whether your back office is operating smoothly. Sydecar's responsive and proactive customer support team is there to assist, helping you build trust with your investors and tackle the challenges of building your firm.
Visit sydecar.io/ventureunlocked to learn more.
About Jenny Fielding:Jenny Fielding is the Co-Founder and Managing Partner of Everywhere Ventures. She is one of the most active global pre-seed investors, having invested in 300+ companies as the first money in. Jenny has built a thriving community of 500+ founders and operators who help source, diligence, and invest in the next generation of startups across 3 core verticals: money, health, and work.
Prior to Everywhere, Jenny spent 7.5 years as the Managing Director of Techstars where she invested in a portfolio of companies with a current market cap over $10B. Jenny is a 2x founder, a lawyer by training, and an adjunct professor at Columbia University and Cornell Tech.
About Kirby Winfield:Kirby Winfield is the Founding General Partner at Ascend.vc, the most prolific pre-seed stage venture fund in the Pacific Northwest.
Kirby has been operating and investing in Artificial Intelligence and Machine Learning since the 1990s. His first startup pioneered the use of semantic AI for web search. He advised the Allen Institute of Artificial Intelligence on the launch and growth of its highly regarded Ai2 Incubator program, and has backed 30+ AI startups as a VC.
Early in his career, Kirby was a founding team member and operating executive at back-to-back tech IPOs, with Go2Net and Marchex. He is also a two-time venture capital-backed CEO, with AdXpose (DFJ, Ignition) acquired by comScore, and Dwellable (Maveron, VersionOne) acquired by HomeAway.
About Nate Williams:Nate Williams is the co-Founder and Managing Partner of DeepTech seed fund UNION Labs Ventures and formerly an Entrepreneur-in-Residence (EIR) at Kleiner Perkins focused on opportunities in Climate, PropTech, and Mobility. Nate's track record includes senior leadership experiences executing through startup, growth and turnaround stage culminating in successful exits for 4Home (to Motorola '10), Motorola Mobility (to Google '12), Motorola Home (to ARRIS '13) and August Home (to Assa Abloy '17).
Prior to Kleiner Perkins, Nate was CRO & Head of Platform PM at August Home, Inc. a leader in Smart Home Access where he secured August commercial growth with market leaders and integration partners including Airbnb, Wal-Mart, Amazon, Honeywell, Comcast, and Google/Nest. Nate was also Senior

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.
We are thrilled to bring you a conversation with David Sacks, Founder and Partner of Craft Ventures. Based in San Francisco, Craft was founded in 2017 and currently has over 3 billion in assets under management.
Across the last three decades, David has been incredibly influential as an investor, entrepreneur, and public thought leader. When starting Craft, he was able to draw from his deep operating background, having worked as an early leader at PayPal, and then later founding Yammer, which he sold to Microsoft for $1.2 Billion.
He is also one of the hosts of the All In Podcast, one of the most listened podcasts in the world.
We had a wide-ranging dialogue that took us through the evolution of Craft Ventures from its initial days to today, the strategic decision-making behind scaling fund sizes and team growth, and his overall views on the current outlook of venture capital.
If you’re a VC investor, then I’m sure you already know about Sydecar, the go-to platform for emerging VCs to manage their SPVs and funds. Sydecar is on a mission to make private markets more accessible, transparent, and liquid by standardizing how investment vehicles are created and executed. Their powerful software allows VCs to launch SPVs and funds instantaneously, track funding in real time, and offer hassle-free opportunities for early liquidity.
Whether you’re syndicating your first or fiftieth deal, Sydecar acts as your silent operating partner, handling all back-office functions in a single place. Sydecar always has your back, so that you never have to worry about chasing subscription docs, lost wires, or late K-1s.
With all the recent ups and downs in the private markets, the last thing you want to worry about is whether your back office is operating smoothly. Sydecar's responsive and proactive customer support team is there to assist, helping you build trust with your investors and tackle the challenges of building your firm.
Visit sydecar.io/ventureunlocked to learn more.
About David Sacks:David Sacks is Co-Founder and Partner at Craft. He has been a successful founder and investor for over two decades, building and investing in some of the most iconic companies in tech. David has invested in over 20 unicorns, including Affirm, AirBnB, Bird, ClickUp, Eventbrite, Facebook, Houzz, Lyft, OpenDoor, Palantir, Postmates, Reddit, Slack, SpaceX, Twitter, Uber, and Wish.David first got involved in the technology industry in 1999 when he joined early-stage startup Confinity, later renamed PayPal. Serving as the company’s first product leader and then as COO, David built and ran many of the company’s key teams, including product management and design, sales and marketing, business development, international, customer service, fraud operations, and HR. He pivoted the product from beaming money on Palm Pilots to emailing money on the web, and introduced the business model. When the company IPO’d on the Nasdaq in 2002, David was 29 — the median age of the “PayPal Mafia” executives listed on the S-1. PayPal was later acquired by eBay and eventually spun back out into a publicly traded company (under ticker symbol PYPL).David is well-known in Silicon Valley for his product acumen. AngelList’s Naval Ravikant has called David “the world’s best product strategist.” And has received acclaim as one of the Besties on the All In Podcast.
In this episode, we discuss:
(02:56) David Sacks discusses transitioning from being an entrepreneur with experiences at PayPal and Yammer to founding Craft Ventures, emphasizing the focus on SaaS and leveraging operational expertise to support startups.
(04:56) The growth of Craft Ventures from its initial fund to managing $3.5 billion, focusing on SaaS and marketplaces, and how fund size affects strategy
(08:15) Portfolio construction and the strategic shift towards reserving mor

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.
This week we are pleased to be joined by Adam Bain of 01 Advisors, a San Francisco-based firm with nearly $1 billion under management.
Adam and his partners, including Dick Costolo, have taken a very different approach to the venture model, drawing from their experiences as operators. While Adam was COO and Dick was CEO at Twitter, they helped the company scale from zero to in revenue as fast as any consumer tech company in history. During this time, they spent a significant amount of time with the late Bill Campbell, the legendary CEO coach who helped inspire the foundation for 01 Advisors.
Since founding the firm in 2018, they have a uniquely focused approach to venture coaching and unlike other Series B and later VCs, they do not take board seats. We went through the why of this model. Along with topics such as the transition from operating to investing. And the future of potentially using models to determine founder archetypes.
If you’re a VC investor, then I’m sure you already know about Sydecar, the go-to platform for emerging VCs to manage their SPVs and funds. Sydecar is on a mission to make private markets more accessible, transparent, and liquid by standardizing how investment vehicles are created and executed. Their powerful software allows VCs to launch SPVs and funds instantaneously, track funding in real time, and offer hassle-free opportunities for early liquidity.
Whether you’re syndicating your first or fiftieth deal, Sydecar acts as your silent operating partner, handling all back-office functions in a single place. Sydecar always has your back, so that you never have to worry about chasing subscription docs, lost wires, or late K-1s.
With all the recent ups and downs in the private markets, the last thing you want to worry about is whether your back office is operating smoothly. Sydecar's responsive and proactive customer support team is there to assist, helping you build trust with your investors and tackle the challenges of building your firm.
Visit sydecar.io/ventureunlocked to learn more.
About Adam BainAdam is a Co-Founder and Managing Partner for 01 Advisors, a venture & advisory firm that helps founders go from building a product to building a company with operational expertise.He was previously the COO for Twitter and a Board Director for Opendoor.
In this episode, we discuss:
(03:01) Adam shares his journey from Twitter to founding 01 Advisors, focusing on the transition from advertising and social media to a venture model that combines investing and advising
(05:00) The unique backgrounds of 01 Advisors' partners in scaling companies from zero to significant revenues, showcasing a rare collective experience in tech leadership
(08:01) The venture coaching approach at 01 Advisors that was inspired by Bill Campbell
(14:35) Why 01 Advisors chooses not to take board seats, aiming to offer more effective and unrestricted guidance to CEOs
(18:14) Helping CEOs appoint seasoned operators to board positions, ensuring comprehensive support without direct board involvement
(22:08) 01 Advisors' focus on Series B investments, aligning their operational expertise with companies at a pivotal growth stage
(24:16) 01's strategy of a concentrated portfolio to deeply engage and support their investments, contrary to the broader trend towards more extensive portfolios.
(27:25) Diligence process for revenue streams and operational dynamics, aiming to identify areas where 01 can significantly impact growth.
(29:00) The use of cognitive psychology for deeper CEO assessments post-investment, aiming to tailor support strategies to each leader's unique strengths and challenges
(31:16) The early successes of this cognitive approach
(34:42) The transition from high level operator to investor
(39:58) Why he’s excited continuous intellectual growth and the diverse learning experiences