Venture Unlocked: The playbook for venture capital managers

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.

This week we welcome the three co-founders of Saga Ventures: Ben Braverman, Thomson Nguyen, and Max Altman. Saga Ventures is a seed-stage investment firm that recently closed its first fund of $125M.

The conversation dives into their experiences in raising their first fund, building a team, and navigating a competitive seed-stage market. The co-founders bring unique skill sets from their previous roles in operating and investing, and this episode sheds light on how they strategically combine those skills to differentiate themselves from other firms.

About Ben Braverman

Ben Braverman is a Co-Founder and Managing Partner at Saga Ventures, a $125M venture capital fund he co-launched in March 2024 alongside Max Altman and Thomson Nguyen. At Saga, Ben focuses on early-stage investments, working with pre-seed and seed-stage companies across various sectors. His background in scaling companies' go-to-market strategies provides valuable insight into helping startups grow efficiently and sustainably.

Before founding Saga Ventures, Ben spent nearly nine years at Flexport, a major player in the logistics space. Starting as Chief Revenue Officer in 2014, he was instrumental in building and scaling Flexport’s global sales and go-to-market teams. Later, as Chief Customer Officer, Ben oversaw customer relationships and corporate development, ensuring the company's growth aligned with customer needs. His final role at Flexport saw him leading Flexport Ventures and Corporate Development, where he focused on the company's strategic investments.

Earlier in his career, Ben held growth and sales leadership positions at startups like URX, which was acquired by Pinterest, and Heyzap, acquired by RNTS Media. He holds a degree from Vassar College and has spent his career helping innovative companies grow through a hands-on approach to business development and customer engagement.

About Thomson Nguyen

Thomson Nguyen is a Co-Founder and Managing Partner at Saga Ventures, where he has been since March 2024. At Saga, he focuses on early-stage investments in technology-driven companies, drawing on his extensive experience in data science, machine learning, and entrepreneurship. Thomson’s deep technical expertise helps him identify promising startups, especially those at the intersection of technology and business.

Prior to Saga, Thomson founded Nearside, a financial services platform for small businesses, which he led from 2019 until its acquisition by Plastiq in 2022. Before that, he was an Entrepreneur in Residence at Kleiner Perkins and the Head of Capital Data Science at Square, where he managed the data science team responsible for critical business areas like default risk, marketing optimization, and product innovation. His career in fintech is rooted in his work at Framed Data, a startup he founded and later sold to Square.

Thomson started his career as a data scientist at tech companies like Lookout and Causes, where he applied his expertise to user segmentation and predictive analytics. He also has a longstanding academic affiliation with New York University’s Courant Institute, where he continues to contribute to research in machine learning and cybersecurity. Thomson holds degrees in Applied Mathematics from the University of Cambridge and Mathematics from the University of California, Berkeley.

About Max Altman

Max Altman is a Co-Founder and Managing Partner at Saga Ventures, a venture capital fund he helped establish in March 2024. Max focuses on investing in pre-seed and seed-stage companies, working closely with his co-founders to identify and support high-potential startups. His experience as both an investor and operator allows him to bridge the gap between capital and company-building.

Before co-founding Saga Ventures, Max was a Partner at Alt Capital from 2021 to 2024, where he invested in early-stage companies. Prior to that, he held a similar role at Apollo Projects, another investment firm focused on startups. His career as an investor began at Hydrazine Capital, where he worked from 2016 to 2019. During his time there, Max honed his skills in evaluating high-growth tech companies and building meaningful relationships with founders.

Earlier in his career, Max gained operating experience at Zenefits, where he worked in product management, and at Allston Trading as a trader. He also spent time at Microsoft as a program manager. Max holds a degree in Computer Science from Duke University and has built his career by combining his technical background with a passion for early-stage investments.

In this episode, we discuss:

* (01:42) The origin story of Saga Ventures, and how the co-founders decided to join forces. Max Altman shares how the idea of starting a fund came about and why he didn't want to follow a solo GP model

* (03:31) The unique, complementary skill sets the team brings to the table—Ben’s expertise in go-to-market strategy, Thomson’s technical knowledge, and Max’s investor relationships—and how this combination is designed to support early-stage founders

* (04:58) Their hands-on, founder-first approach, focusing on critical areas like product development and initial hires, differentiates Saga from other early-stage firms.

* (06:11) The "reality meter" and the importance of being able to take hard hits as an entrepreneur or venture firm, emphasizing how all three co-founders share this mentality

* (07:50) The team reflects on the challenges of raising their first fund, including dealing with partnership risk, self-awareness, and the difficulties of convincing LPs early on without firm commitments

* (10:02) The careful consideration that went into deciding the fund size of $125M, balancing capital deployment with staying competitive in seed-stage deals.

* (12:00) Their fundraising process, the strategic decisions involved, and the importance of securing anchor investors before taking meetings with LPs.

* (15:19) What LPs are looking for in early-stage venture firms and the role of partnership risk in their decision-making process

* (17:33) Why their shared vision and complementary skill sets have aligned them for long-term success as a team, along with their commitment to focusing on specific sectors like fintech and infrastructure

* (19:22) The importance of having a clear value-add for founders beyond capital, and the importance of storytelling and salesmanship in early-stage companies

* (23:25) The internal decision-making process at Saga, how the partners determine which deals to pursue, and the dynamics of reaching consensus when choosing investments

* (26:45) Patience and long-term thinking are critical when evaluating deals, and how they ensure they don’t rush into investments just for fear of missing out

* (28:19) The importance of founder resilience and self-awareness, noting that the best founders are those who can attract talent and navigate through difficult times

* (30:00) Why salesmanship and charisma are critical qualities in founders, as startup leadership often requires convincing others to join and invest in challenging ventures

* (32:00) The team discusses their approach to sourcing and winning deals in a highly competitive market, focusing on the importance of building trust and delivering consistent value to founders.

* (34:05) Max talks about the significance of being the first firm to back companies and how they collaborate with other VCs to co-lead investments.

* (36:45) Being transparent and responsive to founders creates lasting relationships, even when they pass on deals

* (38:04) How they measure success internally at Saga Ventures, focusing on inputs such as responsiveness and the strength of founder relationships, while understanding that long-term results will take years to evaluate

* (41:00) Key lessons from the fundraising process, stressing the importance of clarity when positioning their fund to LPs and being patient in closing commitments

* (43:25) How the venture landscape has evolved over the past 18 years, highlighting the increasing competition and the need for VCs to be highly self-aware and strategic when entering deals

* (45:40) Building a venture firm requires a long-term mindset, much like running a successful company

I’d love to know what you took away from this conversation with Glenn. 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

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.

Today we're thrilled to be joined by Glenn Solomon, managing partner at Notable Capital. Along with Granite Asia, Notable Capital was one of two groups to emerge from GGV Capital, which recently split into two groups with Notable based in Silicon Valley, New York, and covering companies in the U. S., Israel, Europe, and Latin America.

Glenn brings nearly 30 years of venture experience to the table, and it was great to draw from his insights in investing, building firms, and working with high performing teams.

About Glenn Solomon:Glenn Solomon is the Managing Partner at Notable Capital. He focuses on investing in early to growth-stage companies across different sectors, including cloud infrastructure and business applications. He also serves on the boards of several companies, such as HashiCorp, Opendoor.com, and Orca Security.

Before joining Notable, Glenn was a General Partner at Partech International from 1997 to 2006, where he worked on technology investments. Earlier in his career, he was an associate at SPO Partners from 1993 to 1995 and started as a financial analyst at Goldman Sachs from 1991 to 1993.

Glenn Solomon earned his MBA and BA from Stanford University.

In this episode, we discuss:

(01:42) Glenn’s journey from playing tennis at Stanford to discovering a passion for technology and investing

(02:44) A pivotal moment when encountering the internet for the first time, which sparked a deeper interest in technology

(04:06) The transition from Partech International to joining Granite Global Ventures in the mid-2000s

(05:03) The appeal of GGV's global perspective and innovative approach in venture capital

(07:48) The early strategy at GGV, focusing on differentiation in the venture space

(09:01) The necessity of adapting to the evolving nature of the industry

(10:29) The rebranding to Notable Capital and the strategic decisions following the split from GGV’s Asia team

(12:39) The guiding principles at Notable Capital, emphasizing the importance of speed and maintaining a sector-focused strategy

(15:19) An example of a recent deal showcasing how the firm’s flat structure empowers all team members to contribute significantly

(17:33) Staying focused on specific sectors and building a strong support platform for portfolio companies

(23:25) Engaging with CSOs and CDOs to maintain an edge in cybersecurity and data sectors.

(27:00) Discusses the importance of resourcefulness in venture capital and how they assess this quality during interviews.

(36:31) Advice on being a successful VC, stressing the critical role of building strong, lasting relationships

(39:30) Success in venture capital fundamentally relies on working with exceptional people

I’d love to know what you took away from this conversation with Glenn. 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

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.

In this episode, we are thrilled to be joined by Ben Sun, co-founder of Primary, a seed-stage fund based in New York. Ben shares his journey from investment banking to startup founder, and eventually to co-founding Primary, which has backed companies like Coupang and Jet.

Ben provides deep insights into venture math and the intricacies of completing a GP-led secondary. He discusses his background and the inspiration behind starting Primary in 2015. Ben talks about the challenges he faced as a founder and the importance of truly understanding the business as a VC. He explains Primary's hands-on approach, emphasizing the need for a high seed-to-A graduation rate and how their impact team supports portfolio companies.

The conversation covers the metrics used to measure success and the importance of waiting for the right investment opportunities. Ben explores the changing landscape of venture capital, strategies for finding alpha and generating returns, and the importance of sector specialization and deep sector expertise. He also touches on deal flow challenges at the seed stage and the role of incubations in lowering the cost basis.

So many great nuggets in this episode, enjoy!

About Ben Sun:Ben is a Co-Founder and General Partner at Primary. Forbes' Midas List ranks him as one of the top 100 tech investors in the world. His founder-first approach originates from having been one: His experiences cofounding Community Connect, one of the first social networking companies, and LaunchTime, an incubator, inform how he supports founders in the portfolio.

Ben focuses his investing activities on primarily consumer-facing companies. Ben has been active in the NYC tech community for over 20 years. Prior to becoming an entrepreneur and investor, Ben worked at Merrill Lynch in the Technology Investment Banking Group, but he really began his career at the age of eight when he worked in his parents’ Chinese restaurant.

In this episode, we discuss:

(01:21) Journey from investment banking to founding Primary Ventures.

(03:45) Starting Primary Ventures and focusing on seed-stage investments in New York.

(04:12) Emphasis on being hands-on and aligning with founders.

(06:34) Roles and functions of the impact team at Primary Ventures.

(10:00) Measuring success through surveys and key performance indicators

(13:23) The importance of choosing the right investment opportunities and achieving high graduation rates from seed to series A

(22:00) How partners wait for the right pitch using an internal rubric

(26:57) Benefits of sector specialization, with a focus on fintech expertise

(35:00) Strategies for maintaining a low-cost basis and navigating market fluctuations, including secondary sales

(41:00) GP-led secondaries and benefits of providing liquidity to limited partners

(49:00) Advice for new venture capitalists: support founders and develop a long-term strategy

I’d love to know what you took away from this conversation with Lindel. 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

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.

This week I'm excited to sit down with Lindel Eakman from Foundry. Lindel has been an investor in funds and companies since the early 2000s when he started at UTIMCO.

In our conversation, Lindel talks about being one of the first investors in Union Square Ventures, his preference for smaller partnerships, and the art of conducting quality reference calls on GPs. Having known each other for a while, our chat felt like a fun and casual water cooler conversation about the venture capital world.

About Lindel Eakman:Lindel Eakman is a partner at Foundry, where he focuses on early-stage investing. Since joining in 2015, Lindel has been active across the portfolio, working closely with partner funds and leading new direct investments. He is known for his humble and supportive approach, valuing the hard work of founders.

Before Foundry, Lindel managed the private investment program at the University of Texas Investment Management Company (UTIMCO) from 2002 to 2015. At UTIMCO, he built the venture capital program and invested in firms like IA Ventures, True Ventures, Union Square Ventures, and Foundry.

Lindel began his career in finance at KPMG in the M&A Tax Practice from 1997 to 2001 and then worked as a Corporate Finance Associate at Stephens, Inc. in 2002. He holds an MBA from the University of Texas at Austin McCombs School of Business and a BBA in Accounting and Finance from Texas Christian University. He is a CPA and a CFA charter holder.

In this episode, we discuss:

(01:14) Early Career and Union Square Ventures and moving to Foundry

(03:00) Investment Philosophy and Strategy

(04:28) The value of partnering with emerging managers

(05:55) Selecting GPs and Making Investment Decisions

(10:30) The Current Venture Market Landscape in 2024.

(13:00) Challenges and Opportunities for New Managers

(17:00) Future of Venture Capital

(21:00) Importance of People in Venture

(25:00) Secondaries and Liquidity Opportunities

(29:00) The importance of evaluating partnership dynamics in emerging managers

(33:00) Best practices for conducting reference checks.

(37:00) How virtual interactions affect partnership assessments and fundraising

(42:00) Advice for new managers on constructing a venture portfolio, focusing on sectors and small funds

(47:00) Role of Large Funds in a Venture Portfolio

I’d love to know what you took away from this conversation with Lindel. 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

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

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

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 among team members.

I’d love to know what you took away from this conversation with TX. 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

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.

A word from our sponsor:

As a founder, you understand the power of efficiency and growth. And with accelerator checking, earning up to 2.25 percent APY, your money works as hard as you do. For those aiming higher, you can unlock the full potential of your cash reserves with exclusive access to accelerator money market savings earning 4 percent APY on balances over $50,000.

Say goodbye to unnecessary fees and hello to Grasshopper Bank, your next leap forward.

Nationally chartered and headquartered in New York City, Grasshopper is a client-first digital bank built to serve the business and innovation economy, combining the best of banking technology and years of industry expertise to deliver best-in-class experiences with trusted security and unparalleled support.

It's time to switch, and make Grasshopper your financial foundation and watch your cash reserves grow as much as your business.

Grasshopper, the future of startup banking.

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 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

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.

A word from our sponsor

In the fast-paced world of startups, every decision counts. And for venture-backed startups, choosing the right banking partner can make all the difference. That’s why you need to consider Grasshopper Bank. 

Nationally chartered and headquartered in New York City, Grasshopper Bank is a client-first digital bank built to serve the business and innovation economy, combining the best of banking technology and years of industry expertise to deliver best-in-class experiences with trusted security and unparalleled support. 

Join the ranks of forward-thinking entrepreneurs who love their digital platform by applying online in as little as 5 minutes from any device today at www.grasshopper.bank.

Grasshopper - where banking meets innovation.

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

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