11 episodes

Venture Unlocked is the playbook for starting, operating, & scaling a successful venture capital firm. Samir Kaji, Host of Venture Unlocked has +20-years of experience assisting & advising startups and venture firms. Listen for VC fund guidance.

ventureunlocked.substack.com

Venture Unlocked: The playbook for venture capital managers. Samir Kaji

    • Investing

Venture Unlocked is the playbook for starting, operating, & scaling a successful venture capital firm. Samir Kaji, Host of Venture Unlocked has +20-years of experience assisting & advising startups and venture firms. Listen for VC fund guidance.

ventureunlocked.substack.com

    Venture Unlocked ep. 10 - Costanoa Ventures Greg Sands on building a boutique Venture Firm, firm culture, and portfolio theory.

    Venture Unlocked ep. 10 - Costanoa Ventures Greg Sands on building a boutique Venture Firm, firm culture, and portfolio theory.

    In this episode, we speak to industry veteran Greg Sands, who founded Costanoa Ventures after spending 13 years at Sutter Hill Ventures. Prior to Sutter Hill, Greg serves as the first product manager of Netscape (where he wrote the initial product plan and coined the name “Netscape”).

    He founded Costanoa Ventures as a boutique early stage firm to solve for a gap he saw between seed stage funds and larger lifecycle firms. The firm primarily invests in B2B seed stage companies in categories such as the Future of work, Fintech, Data/Machine learning, and security.

    Although the firm employs a traditional craft approach to venture capital investing, their model is unique in many ways including the incubation/co-creation of companies and the use of in-house operating partners to add value to portfolio founders.

    In this episode, Greg and I discuss:

    What was it like leaving Sutter Hill and raising a fund for the very first time as a solo-GP.

    The role of having mentors and champions around you when starting off.

    How he thinks about hiring team members.

    What it means to build and maintain a culture designed for durability.

    Why they take a relatively concentrated approach to investing, and how this translates to portfolio construction theory.

    Why venture is a service business.

    Mentioned in this episode:

    Costanoa Ventures

    I’d love to know what you took away from my conversation with Greg Sands. 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.

    Get on the email list at ventureunlocked.substack.com

    • 43 min
    Venture Unlocked 009 - Fifth Wall's Brendan Wallace on building a different type of venture firm

    Venture Unlocked 009 - Fifth Wall's Brendan Wallace on building a different type of venture firm

    In just a few short years, Fifth Wall Ventures, which focuses on investing in companies in the “built world” economy, has quickly become one of LA’s largest venture firms with over $1.2B in committed LP capital.

    I met Co-Founder Brendan Wallace when he and Brad Greiwe started Fifth Wall nearly five years ago and the trajectory of the firm has been nothing short of astounding.  

    Brendan started his career at Goldman Sachs in real estate investment banking after graduating from Princeton. What’s always struck me over the years is Brendan’s unique vision on how he thinks about building a consistent alpha generating firm.

    In this episode, Brendan and I cover:

    How to manage a LP based with both corporates and financial LPs.

    Providing value add and driving synergies between his LPs and portfolio companies.

    Why the conventional wisdom that large fund sizes are a direct line to weakening performance isn’t always the case if certain characteristics are present in the firm’s model.

    How he thinks about developing and managing a platform that includes advisory, operations and investing.

    Why he doesn’t think the traditional venture model is well constructed for outsized returns at scale.

    How different type of fund products under one roof can drive cross-over value and improve return profiles.

    Mentioned in this episode:

    Fifth Wall

    I’d love to know what you took away from my conversation with Brendan Wallace. 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.

    Get on the email list at ventureunlocked.substack.com

    • 48 min
    Venture Unlocked Episode 008 - Leo Polovets, Susa Ventures

    Venture Unlocked Episode 008 - Leo Polovets, Susa Ventures

    Leo Polovets is one of the Founding Partners of Susa Ventures, which launched in 2012. Over the last 8 years, Susa has established itself as one of the premier seed funds in the world, and have made more than 80 investments in companies like Robinhood, Flexport, Andela, and Expanse (recently purchased by Palo Alto Networks for $800MM). 

    Leo began his career as a software engineer, first at LinkedIn when it was a start-up, and later at Google and Factual.

    I always enjoy speaking with Leo as he’s always introspective, insightful and stays highly curious about all aspects of venture (check out his great blog, “Coding VC”).

    In this episode, Leo and I discuss the following topics:

    Why Susa had 4 partners for a $25MM fund.

    Leo’s acronym for building a venture thesis: C.A.S.H. (Constraints, Actionable, Special, Helping).

    Can VC firms truly differentiate, and if so, how?

    The importance of being helpful to founders and building those relationships early.

    Portfolio construction: Going all-in on one investment vs. many small investments.

    When to grow fund sizes, and how to think about this.

    The role of opportunity funds and why they raised one alongside Fund III.

    Mentioned in this episode:

    Susa Ventures

    Leo’s blog Coding VC

    Patrick O’Shaughnessy’s podcast, Invest Like the Best

    I’d love to know what you took away from my conversation with Leo Polovets. 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.

    Please share Venture Unlocked with others who want to learn about venture capital:

    Get on the email list at ventureunlocked.substack.com

    • 38 min
    Venture Unlocked Episode 007: Sahil Lavingia's learnings as a VC backed founder and running a Rolling Fund

    Venture Unlocked Episode 007: Sahil Lavingia's learnings as a VC backed founder and running a Rolling Fund

    This episode is a fun one as I had the pleasure to interview Sahil Lavingia, founder of Gumroad, an online platform that allows creators to sell directly to their consumers. The company has facilitated the sale of $356 million in products since its launch in 2011 and now helps over 70,000 creators.

    Gumroad raised capital from legendary angels like Ron Conway, Chris Sacca, Naval Ravikant, and from distinguished venture firms such as First Round Capital, Accel Partners, and Kleiner Perkins. After a failed series B in 2015, Sahil was forced to lay off the majority of his staff and pivot his company building strategy to one atypical to the traditional venture model, but in the last year Gumroad doubled its ARR to $10MM.

    Drawing on his experiences as an angel investor backing companies such as Hellosign, Figma Design, and Lambda School, Sahil decided to raise his own venture vehicle and using the nascent AngelList Rolling Fund product, quickly secured $1MM/quarter in LP funding. Today’s he’s the most prominent AngelList Rolling Fund Manager with nearly $10MM of annual commitments.

    In this episode, Sahil and I discuss the following:

    Sahil’s start at Pinterest and how he applies his founder experiences in investing.

    His learnings from working with VC’s and his thoughts on what he believes makes for a great VC partner.

    Why he decided to go down the investment route, and what was it like raising LP capital through a Rolling Fund.

    Why founders may be more inclined to raise early capital from other founders rather than traditional institutional investors, and how Sequoia has created a savvy model to combat this trend.

    Thoughts on the early stage funding market moving forward.

    How he thinks about portfolio construction as a Rolling Fund investor.

    His hopes for innovation in the venture: Expansion of rolling funds, buyers and sellers being directly connected, and the breaking of the geographical privilege bubble.

    Mentioned in this episode:

    Gumroad

    My blog post on rolling funds

    I’d love to know what you took away from my conversation with Sahil Lavingia. 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.

    Also subscribe to Venture Unlocked on Itunes to ensure you’ll get each episode when it’s first released.

    Get on the email list at ventureunlocked.substack.com

    • 40 min
    Venture Unlocked Episode 006 - Ted Maidenberg, Tribe Capital

    Venture Unlocked Episode 006 - Ted Maidenberg, Tribe Capital

    On this episode, we speak with Ted Maidenberg, co-founding partner of Tribe Capital, which he launched with his partners Arjun Sethi and Jonathan Hsu. I’m especially excited to bring this episode to you as Ted draws from experiences working within a Corporate VC (Time Warner), a traditional VC (USVP), and now has co-founded two firms known for their innovative approaches to investing —- Social Capital in 2011 with Chamath Palihapitiya and Mamoon Hamid, and most recently Tribe.

    Ted has also been part of investing teams that count investments such as Slack, Carta, and Survey Monkey.

    In this episode, Ted and I discuss the following topics:

    Starting Social Capital after the global financial crisis

    Starting and fundraising for a new firm (Tribe) in a very noisy market.

    The importance of trust in venture teams, the role of partnership dynamics, and maintaining culture.

    Their use of a data driven quantitative framework to evaluate companies through Cohort behavior and how this gives them an edge relative to heuristic only methods.

    The importance of getting ownership of a company early, and how it impacts reserve strategy.

    Their productized use of SPV’s in driving portfolio construction strategy, adding value to companies, and providing a unique return model for SPV and Fund LP’s.

    Are there any other innovations that can/should happen in VC?

    Ted’s advice for those that are just launching firms today.

    Mentioned in this episode:

    The Magic Eight Ball

    Social Capital and Tribe Capital

    I’d love to know what you took away from my conversations with Ted Maidenberg; 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.

    Get on the email list at ventureunlocked.substack.com

    • 39 min
    Ep 005. Jon Sakoda: Build Your Fund With Founders By Your Side

    Ep 005. Jon Sakoda: Build Your Fund With Founders By Your Side

    Jon Sakoda is the Founding Partner at Decibel, a venture firm that was created in partnership with Cisco (but independent in nature) in 2018 to invest in early-stage companies.

    Hear how Jon, who describes himself as a “recovering entrepreneur,” started his first company, Imlogic, Inc. which was eventually acquired by Symantec, and then joined New Enterprise Associates (NEA) in 2006 where he served as a partner for 12 years. During his time at NEA, NEA clearly established itself as the largest venture firm in the world and had raised a $2.5B fund well before the current mega-fund boom.

    In this episode, Jon and I cover the following topics:

    Jon’s trajectory from being a technical operator to a VC.

    The bundling and unbundling of venture capital, and what we should see going forward.

    Do VC’s really add value? What leads to the belief by founders that they might not?

    The role of Cisco and how it helps them differentiate and punch above their weight in helping founders.

    How traditional economic LPs view corporate LPs and how GPs can navigate the discussions.

    What new GPs often underestimate when starting a fund

    Mentioned in this episode:

    Decibel website, and their partnership with Cisco.

    I’d love to know what you took away from my conversations with Jon Sakoda; 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.

    Get on the email list at ventureunlocked.substack.com

    • 39 min

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