The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Jeff Russakow, CEO of Boosted, a pioneering electric skateboard startup, shares his journey from leading enterprise companies to rethinking urban travel. He discusses the crucial question founders must ask when selecting investors and the common pitfalls they face. Jeff elaborates on the challenges of Series B fundraising, focusing on balancing unit economics with a long-term vision. He also critiques the notion that "hardware is hard," advocating for a richer understanding of product challenges and innovation in transportation.

Garry Tan, Co-founder and Managing Partner at Initialized Capital, shares insights from his extensive experience in early-stage venture capital. He emphasizes the critical role of trust and relationships for founders facing challenges, especially around product-market fit. Garry also discusses the evolution of ownership requirements as funds grow, revealing how his mindset has shifted from angel investing to handling larger stakes. He reflects on the importance of delivering constructive feedback and the need for technical expertise in driving innovation.

Joel Gascoigne, Co-founder and CEO of Buffer, discusses his journey from web developer to running a profitable social media management tool. He highlights the critical moments when founders risk losing control, emphasizing that fundraising decisions are more significant than many realize. Joel critiques the current VC landscape and advocates for alternative financing to ensure founder independence. The conversation also touches on team transparency and Buffer's future plans for sustainable growth and product diversification.

Alex Clayton, a Partner at Spark Capital, shares his journey from investment banking at Goldman Sachs to becoming a key player in growth-stage SaaS investments. He explores how to effectively source deals, emphasizing the significance of network-driven sourcing and the nuances between early-stage and growth investing. Alex discusses the importance of market depth in analyzing investments and shares insights on the dynamics between founders and investors. Additionally, he draws parallels between competitive sports and investment strategies, highlighting skills that translate from tennis to venture capital.

Mike Hirshland, co-founder of Resolute Ventures and former partner at Polaris, shares his journey from legal clerk to venture capitalist. He discusses the nuances of seed investing, identifying acceptable risks, and why some firms shouldn’t operate with large funds. Mike emphasizes ownership over loss ratios, advocating for strong founder-VC relationships and the need for diversification in portfolios. He also explores an exciting investment in a new SaaS startup, showcasing the essential resources that support emerging entrepreneurs.

In this discussion, Adam Pritzker, Chairman & CEO of Assembled Brands and co-founder of General Assembly, delves into the intricate dynamics of financing consumer brands. He highlights the broken VC mechanisms and the need for tailored solutions for emerging brands. Adam shares his optimism about the retail landscape's evolution and the rise of niche markets. He also sheds light on Instagram's pivotal role in modern commerce, the challenges of customer acquisition, and the importance of adaptive marketing strategies for sustainable growth.

Victoria Treyger, General Partner at Felicis Ventures, shares her wealth of experience from scaling revenue at Kabbage to her current role in venture capital. She reveals surprising challenges in transitioning from operations to VC, emphasizing the importance of trust with founders. Victoria discusses effective coaching strategies for investors and the vital role of independent board members. Additionally, she highlights disruptive trends in consumer goods, including the clean movement and innovations for underserved markets, pointing to future opportunities.

In this engaging discussion, Austen Allred, the Founder and CEO of Lambda School, dives into his transformative journey from living in his car to building a leading coding school with a unique income share model. He tackles the future of unemployment as an optimization problem and discusses the importance of thoughtful decision-making in startups. Austen also explores the shift in his perspective on venture capital and shares vital questions founders must consider before seeking funding, shedding light on resilience, risk, and innovation in education.

Jeff Richards is Managing Partner @ GGV Capital, one of the leading venture firms of the last decade with a portfolio including the likes of Alibaba, Slack, Square, Xiaomi, Peloton, OpenDoor, just to name a few. As for Jeff, he sits on the board of or is an observer at BigCommerce, Brightwheel, Gladly, Lambda School, Namely and Tile just to name a few. Jeff also led GGV's investments in Buddy Media (acquired by Salesforce), HotelTonight, Flipboard and has been actively involved in GGV's investments in Opendoor, Domo, Square and Wish. Prior to joining GGV, Jeff founded two software companies: R4 (acquired by VeriSign), and QuantumShift, backed by Texas Pacific Group (TPG). In Today's Episode You Will Learn: 1.) How Jeff made his way into the world of VC with GGV from founding and scaling 2 software companies in the 90s? What were Jeff's 2 biggest takeaways from having the company he founded raise over $100m then go to $0 in the crash? 2.) How does Jeff approach and see the transition from founder to CEO today? When does this transition need to occur? How do first-time founders differ compared to experienced serial entrepreneurs when it comes to building their teams? Where do they often struggle or make mistakes? What advice does Jeff offer them? 3.) Jeff has previously said, "do not raise for the highest valuation", what is his thinking here? What specific examples does Jeff have of why it can hurt and damage both the founder and the company? How does Jeff think about his own price sensitivity today? How does he determine when a stretch is a stretch too far? From backing the likes of Alibaba, Xiaomi and Didi, what were his biggest takeaways when it came to price? 4.) Decision-making is one of the only products venture has, how does Jeff and GGV approach decision-making as a firm today? Being a slightly later stage firm, how do they think about reserve allocation? What does the re-investment decision-making process look like? How does GGV think about attribution as a firm today? What are the benefits? 5.) What advice would Jeff give to an individual that has just entered VC? What does Jeff know now that he wishes he had known at the beginning? How does Jeff think about what it takes to be a truly special board member? What one or two things can a board member do to move the needle in their relationship with their founder? Items Mentioned In Today's Show: Jeff's Fave Book: In an Uncertain World: Tough Choices from Wall Street to Washington Jeff's Most Recent Investment: Lambda School, Electric As always you can follow Harry, The Twenty Minute VC and Jeff on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rob Sadow is the Founder & CEO @ Scoop, the startup that dramatically improves your commute providing convenient carpools with co-workers and neighbours. To date, Rob has raised over $37m in funding for Scoop from the likes of Danny Rimer @ Index, Brook Porter @ G2VP, Zaw Thet @ Signia Venture Partners and BMW i Ventures just to name a few. Before founding Scoop, Rob was a Manager @ Bain & Company and before that spent time in Israel with Better Place, working to provide electric vehicle networks to help accelerate the global transition to sustainable transportation. In Today's Episode You Will Learn: 1.) How Rob made his way from the world of consulting and Bain to founding the future of convenient commutes with Scoop? 2.) How does Rob approach key decisions? What does Brook Porter @ G2VP mean when he says, "from a first principles perspective"? How does Rob determine when to make decisions with the head or the heart? Does Rob agree with Fred Destin, "as a founder, decisions are never perfect, it is about batting average"? Where does Rob see many make mistakes when it comes to decision-making? 3.) How does Rob find the dynamics of working with his brother as his co-founder? What are some of the core challenges? How does one make it scale and how does the relationship need to change over time? What is Rob's biggest advice to others when thinking about the person they partner with? 4.) How does Rob think about board construction? What have been some of Rob's biggest lessons in really using your board to get the most out of them? What works well for this? What does not work? How can founders create this level of relationship with their board members? Should founders direct their ask to specific individuals when soliciting help from their board? 5.) Why does Rob believe that they have next to no attrition of employees at Scoop? What have been some of Rob's biggest lessons when it comes to both culture creation and maintenance? How does Rob think leaders can invest more in their employees? What does this look like? Where do many go wrong or misallocate? Items Mentioned In Today's Show: Rob's Fave Book: The Wheel of Time As always you can follow Harry, The Twenty Minute VC and Rob on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.