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.
Tom Loverro, General Partner at IVP is our guest as part of our Venture Unlocked Shorts series intended to go deep on a single topic.
We revisit Tom’s Twitter post from early 2023, which spoke to the market shift that was in motion and the difficulties start-ups would face in a capital-constrained market. Specifically, he spoke about 2024 as being a time of reckoning for many companies that were built with growth at all costs mentality. 
We went through that original post, and what’s transpired since then, including why it’s time for well-positioned startups to go on offense again. 
Tom brought a lot of interesting insights for founders and VCs alike, so we hope you enjoy the episode. 
About Tom Loverro:Tom Loverro is a General Partner at IVP in Menlo Park, California, where he focuses on investing in enterprise software and fintech companies. Since joining IVP in 2015, he has served as a Board Director or Observer for several companies, including Attentive, NerdWallet, Paper, Podium, Skydio, and TaxBit. He has also co-led investments in Amplitude, Datadog, GitHub, IEX, OnDeck, and Tanium.
Prior to IVP, Tom was a Principal at RRE Ventures, focusing on early and mid-stage startups, and an Entrepreneur-in-Residence at Lightbank. He also served as Senior Director of Product Marketing at Drobo, Inc., and began his career as an Investment Banking Analyst at Goldman Sachs within the Technology, Media, and Telecommunications Group.
Tom holds an MBA from the Kellogg School of Management at Northwestern University, with concentrations in Finance, Marketing, and Entrepreneurship & Innovation. He earned a BA in Political Science and History from Stanford University.
In this episode, we discuss:
(01:37) - Discussion on Tom's Twitter post from January 2023 and its context
(02:09) - Tom's insights on the shift from a zero interest rate environment
(02:59) - The concept of a mass extinction event for startups in 2023-2024
(03:31) - Comparison with the Great Financial Crisis and its impact on startups
(04:01) - The role of venture excess in 2021 and its aftermath
(05:00) - Discussion on venture fund deployment and its impact on startups
(06:49) - Dry powder theory and its implications on startup funding
(07:49) - Insights on current market conditions and startup valuations
(09:14) - Strategies startups adopted in response to market conditions
(10:27) - The three archetypes of startups in the post-2021 era
(13:18) - Observations on fundraising challenges and potential outcomes for startups
(14:48) - Impact of LP capital dynamics on venture funding
(16:34) - The evolving role of private equity in acquiring tech startups
(18:09) - Comparison of venture fund impacts on early and late-stage investors
(21:30) - Discussion on the IPO market and its high bar for startups
(24:19) - The broader ecosystem of liquidity options for startups today
(25:41) - Tom's recent post on shifting from defensive to offensive strategies
(28:47) - Characteristics of startups that should consider going on offense
(30:00) - Importance of survival, product-market fit, and unit economics for startups
(31:50) - Potential exogenous events and their impact on market predictions
(34:00) - Tom's advice to founders on acting with conviction
I’d love to know what you took away from this conversation with Tom. 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.
We're re-joined by Mike Maples, Jr. of Floodgate, this time to discuss his just released new book "Pattern Breakers."
Mike was first on the pod in 2021 and it was great to catch up again, this time to discuss the importance of identifying founders who are true pattern breakers. We spoke about how his observations on the last 14 years at Floodgate inspired him to write the book.
We went through concepts such as founder-future fit, the winning formula of inflections and insights, and his experience that 80% of their returns have been from companies with some major insight or pivot.   
You can find Mike's book "Pattern Breakers" and additional insights on his substack at patternbreakers.substack.com.
About Mike Maples, Jr.:Mike Maples, Jr. is a co-founding Partner at Floodgate. He has been on the Forbes Midas List eight times in the last decade and was also named a “Rising Star” by FORTUNE and profiled by Harvard Business School for his lifetime contributions to entrepreneurship. 
Before becoming a full-time investor, Mike was involved as a founder and operating executive at back-to-back startup IPOs, including Tivoli Systems (IPO TIVS, acquired by IBM) and Motive (IPO MOTV, acquired by Alcatel-Lucent.)
Some of Mike’s investments include Twitter, Twitch.tv, Clover Health, Okta, Outreach, ngmoco, Chegg, Bazaarvoice, and Demandforce.
Mike is known for coining the term “Thunder Lizards,” which is a metaphor derived from Godzilla that describes the tiny number of truly exceptional companies that are wildly disruptive capitalist mutations. Mike likes to think of himself as a hunter of the “atomic eggs” that beget these companies.
Mike is the host of the Pattern Breakers podcast, which shares startup lessons from the super performers.
In this episode, we discuss:
(02:00) The story behind writing "Pattern Breakers" and the investment in Twitch and the importance of pivots
(04:07) Insights from returns on pivots and major insider pivots
(05:02) The concept of founder-future fit and initial skepticism
(07:04) The inflection point of Twitch pivoting from Justin.tv
(10:28) Authenticity and insights in startup founders
(14:32) The role of pattern recognition in startup success
(16:24) Creating movements and attracting early believers
(21:12) Importance of inflection points in startup success
(25:00) Non-obvious inflection points and backcasting
(29:52) The formula of inflection plus insight
(32:00) Non-consensus and right: key to venture success
(34:52) Venture capital and risk-taking
(38:00) Inflections and protecting unconventional ideas
(41:00) Patience as a form of arbitrage in venture investing
(45:00) Insights from Annie Duke on decision-making in venture capital
I’d love to know what you took away from this conversation with Mike. 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.
We're joined by TX Zhuo, Co-Founder and General Partner of Fika Ventures. His tech career began in college when he started an online textbook marketplace.
After working at McKinsey and as a CFO at an operating company, TX joined Innovation Endeavors. He then co-founded Karlin Ventures, which was backed by a single family office. In 2016, he co-founded Fika Ventures, which now has a 10-person team and has raised three funds.
During the pod, we discussed the culture needed to run a successful VC firm, how they've thought about innovation, LP fundraising as a first-time fund, and how they think about valuation methodology.
About TX Zhuo:TX Zhuo is a General Partner at Fika Ventures, a boutique seed fund in Los Angeles investing in data, AI, and automation technologies. He co-founded Fika Ventures in August 2016 and has been dedicated to solving systemic problems through innovative platforms ever since.
Prior to this, he was the Managing Partner at Karlin Ventures from 2012 to 2016, focusing on early-stage investments in various sectors including education technology, digital media, and healthcare. Before Karlin Ventures, TX worked at Innovation Endeavors from October 2010 to May 2012, managing deal screening and outreach initiatives. He also served as the CFO of Lit Motors, an electric vehicle startup, after his tenure at McKinsey & Company from August 2008 to August 2010, where he contributed to financial services and consumer goods projects. TX's entrepreneurial journey began in college when he founded and successfully sold an online textbook marketplace, EMT Alliance, which had significant sales and a cost-efficient distribution center in India.
He holds an MBA from Stanford Graduate School of Business and a Bachelor's degree in Mathematics and Economics from Wesleyan University.
In this episode we discuss:
(01:32) TX Zhuo’s Path to Venture Capital(03:04) Inspired by his own experiences and wanted to create a more institutional platform with Fika Ventures, focusing on supporting seed-stage entrepreneurs with a peer-like approach(05:12) The importance of being founder-first and not imposing advice, adopting a humble approach when communicating with founders(07:14) The difficulties raising the first fund, pitching to 700 investors to get 105 commitments, and learned the importance of storytelling and perseverance(12:49) Radical transparency and conservative financial prudence with LPs, focusing on over-communicating and being proactive about potential issues(16:14) The need to focus on high-impact areas like customer introductions, talent, and follow-on investors, emphasizing trust and being an extension of the management team(19:22) Why TX conducts an expectation-setting exercise early in the relationship with founders, focusing on under-promising and over-delivering to maintain trust and satisfaction(22:39) Navigating 2021's Rapid Fundraising Environment(25:09) How to handle tough conversations with Founders(27:56) Fika’s unique advisor model the uses 73 advisors to support functional and domain-specific needs, and created the Fika Fellows program to up-level senior hires within portfolio companies(34:15) How Fika uses a pod system for focused research and decision-making, requiring a high bar of consensus and a structured voting system for investment decisions(31:39) Why TX screens for a service mentality and resourcefulness in new hires, ensuring they align with Fika's values and ethos through practical evaluations and interactions with current founders(37:43) TX’s Advice for Aspiring VCs: the importance of consistency in approach and team cohesion, advocating for treating every entrepreneur consistently and building a strong, unified brand(39:13) The importance of a consistent experience for entrepreneurs interacting with Fika, valuing a strong apprenticeship model and internal trust

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.
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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