For daily thoughts on the venture landscape, follow me @samirkaji on Twitter. Chris Douvos is the Founder of Ahoy Capital, a boutique Fund of Funds that focuses primarily on allocating into early-stage venture capital funds, while selectively co-investing directly into companies. Chris started his career at Morgan Stanley while still at Yale earning his MBA. From there he worked at Princeton University’s endowment fund where he got his start in venture before moving onto The Investment Fund for Foundations (TIFF). At TIFF he decided that the right strategy was to make “heroic investments” and invest in very early stage, and often unproven managers. This method paid off as Chris was one of the first institutional Limited Partners to back First Round Capital (and remains so). Chris then went on to Venture Investment Associates  (VIA) prior to spinning out to start Ahoy Capital in 2018. Ever engaging, Chris covers a whole host of emerging VC topics and he and I discuss the following:6:20 Why Chris started a fund that invests in emerging managers and how he’s arbitraging people’s inattention to get to true outsized returns.9:00 The process for raising a FoF, and what his LP’s are looking for. 10:59  Ahoy’s portfolio model on managers, and why he thinks concentration is the right avenue for them. 11:54 Why looking at past performance shouldn’t always be the leading indicator in evaluating firms, and why he looks at other specific factors. 13:35 His thoughts on GP/Thesis fit 16:51 How he was introduced to Josh Kopelman of First Round Capital 22:13 Why you need to be able to articulate a sustainable competitive advantage; funds that are good examples of this25:21 Why Chris looks to invest in Venture business builders, not option seekers28:18 The “return the fund” mental model managers should use. 33:00 Why there’s currently a need for liquidity in the ecosystem and why SPACs and direct listings are helpful37:25 Why he’s excited about the diversity, equity, and inclusion GP investments 39:25 Thoughts on Rolling Funds42:18 Chris’ missed investment opportunities43:11 How to pitch Chris (and Fund of Funds in general). Mentioned in this episode:* Ahoy Capital* David Swenson’s Pioneering Portfolio Management* Chris’ blog post: “All About the Benjamins”* Micro VC - Smaller is better, but the math is hard. I’d love to know what you took away from my conversations with Chris Douvos; Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest.Podcast Production support provided by Agent Bee Agency 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

In this episode, we speak with Nate Williams, Co-founder and Managing Partner at UNION Labs. Nate Co-founded UNION Labs in 2018 with his partner, Chris Kim while an Entrepreneur in Residence (EIR) at Kleiner Perkins.Nate is a seasoned Operator and angel investor including August Home, where he served as Chief Revenue Officer and Head of Business. Following their acquisition in 2017, he went on to join KPCB as EIR where he spent time helping entrepreneurs and sourcing investments including Proxy. While EIR, Nate formed a thesis on the opportunity in verticalized IoT which he published in TechCrunch and began to see a lane for a new type of fund.UNION Labs is an early stage firm that both backs and builds companies. They deploy venture investments, as well as manage a structured EIR co-creation program to incubate companies. The core firm focus is on the commercial application of deep technology in artificial intelligence, machine learning, and robotics, that solve real-world problems in smart cities, intelligent homes, or connected transportation. Since its inception, UNION has made five investments, been the lead on three deals, and averages 11% ownership across its current investments.In this episode, Nate and I discuss the following:03:04 - What it was like being an EIR at Kleiner Perkins, and what he learned.06:51 - The dramatic changes in the venture capital industry over the past decade.13:16 - The venture studio concept and when and why it makes sense for a seed firm like theirs to co-create a company.16:47 - Why growth in new corporate venture capital funds may signal a lack of alignment between Fortune 500 companies and Sand Hill Road.17:47 - Nate’s three-pronged approach to raising funds, aka “The Sandwich Strategy.”23:51 - Why transparency is so important both for both Limited Partners and General Partners26:11 - A key observation UNION made early in fundraising from LPs.33:18 - The structural advantages of being a small and specialized fund35:40 - Why deep tech doesn’t automatically mean capital intensive and doesn’t have to include hardwareMentioned in this episode:·       UNION Labs·       Nate’s thesis on the opportunity on verticalized IoT in TechCrunch·       Elizabeth Yin on Venture Unlocked·       OpenLP·       Charles Hudson’s podcast·       Laurence Toney’s post on Quora, “What Is An Entrepreneur in Residence? What Do They Do? How Does It Work?Podcast Production support provided by Agent Bee Agency 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

In this episode, we speak with Soraya Darabi, Co-Founder and General Partner of TMV.  The firm primarily focuses on investing at the seed stage through Series A and is active in areas such as the future of work, education tech, logistics and mobility, and sustainable solutions. While not specifically diversity-focused, the firm’s portfolio is nearly 2/3rd comprised of female or minority-led companies.Earlier in her career, Soraya served as the Manager of Digital Partnerships & Social Media at The New York Times, where she spearheaded social media and digital partnerships. In 2009, she co-founded Foodspotting, named “App of the Year” by both Apple and Wired (later acquired by OpenTable, then Priceline). Over the years, she has been named one of Fast Company’s “100 Most Creative People in Business” for which she was featured on the cover of the magazine. Additionally, Soraya founded and manages Transact Global, a community for female investors to share ideas on firm building and investing.Soraya founded TMV in 2016 with her business partner Marina Hadjipateras. Each utilized their unique backgrounds  -- Soraya in social media and entrepreneurship and Marina in working for her family’s global shipping business. TMV is committed to investing in diverse, purpose-driven founders serving large markets, and leverages a strong operating team to help drive value well beyond what typical seed firms might be able to provide.In this episode, Soraya and I discuss the following:07:46 - Soraya’s definition of a purpose-driven fund10:49 - Key lessons she learned in raising her first, proof of concept fund12:46 - Why TMV and venture is really a services business13:56 - How they prepared themselves between fundraises for scale17:03 - TMV’s deal structure and process for mentoring investments20:35 - The benefits of the TMV’s Venture Partner program27:43 - Why she thinks there will soon be diversity mandates from LPs31:10 - The story of Transact Global34:49 - The GP she most respectsMentioned in this episode:* TMV* Soraya’s podcast Business Schooled* The Venture Hacks Bible* The Operator Collective* All Raise* Darshan Somashekar of TMV’s TechCrunch post on why he left ed tech to go into gamingI’d love to know what you took away from my conversation with Soraya Darabi. 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 Agency 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

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 VenturesI’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. 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

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 WallI’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. 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

Leo Polovets, Founding Partner of Susa Ventures, discusses topics such as building a venture thesis, the differentiation of VC firms, the importance of being helpful to founders, and portfolio construction. He also talks about the early days of Susa Ventures, the challenges of operating with a small fund size, and the process of raising funds and determining fund sizes. Additionally, he emphasizes the need for curiosity and open-mindedness in investing.

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 fundsI’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. 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

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 CapitalI’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. 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

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 fundMentioned 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. 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

Jodi Sherman Jahic is a managing partner of Aligned Partners, a Silicon Valley-based venture fund investing in early-stage, enterprise technology companies that are have a lean toward capital efficiency. Jodi has nearly 20 years of venture experience and started Aligned Partners in 2011 with her co-founder Susan Mason. A meticulous designer of market strategies and a fierce ally of entrepreneurial founders, Jodi is recognized for her thought leadership in go-to-market strategies. Aligned has raised a total of $125 million across three funds.Prior to co-founding Aligned Partners, Jodi led the wireless sector for Voyager Capital and was co-founder and Managing Director of SCG, a pledge fund headquartered in San Francisco focusing on capital-efficient investments. Jodi was selected as an early Kauffman Fellow during her time at Battery Ventures. Previously, Jodi was on the founding team of three startups in North America and Europe, and she worked in the technology industry group at Andersen Consulting (now Accenture). Jodi is co-author of a 2007 book on venture capital investing. She is also a proud founding member of All Raise, focusing on fostering gender diversity in venture capital and tech. In this episode Jodi and I cover the following topics:* How working at larger funds motivated her to start a small fund focused on capital-efficient startups.* How she and her co-founder discovered that they’d work well together and how managers should think about partner selection* Her thoughts on portfolio construction and why they use a concentrated strategy. * The market incentives and social pressure to raise a large fund, and why they are committed to stay small. * Why it is critical to maintain transparent communication with LPs, and how they do it. * What could threaten the modest gains in gender equality in venture capital.Mentioned in this episode:* Aligned Partners* Kauffman Fellows* All RaiseI’d love to know what you took away from my conversations with Jodi; 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. 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