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

Jude Gomila, Founder and CEO of Golden, shares insights from his journey as a prolific angel investor in over 150 startups, including Carta and Superhuman. He discusses the significance of aligning interests between founders and investors and critiques the spray-and-pray investment strategy. Jude emphasizes the importance of algorithmic investing, advocating for structured approaches to decision-making. He also explores the impact of early liquidity on startups and the evolving dynamics in angel investing, offering valuable advice for both investors and founders.

In this conversation with Shoaib Makani, Co-founder and CEO of KeepTruckin, he shares his journey from Google to revolutionizing fleet management. He discusses the necessity of strong distribution strategies and the importance of understanding customer dynamics for successful adoption. Shoaib emphasizes the evolution of a CEO's role and offers insights on market analysis and investor communication. He also touches on the challenges of integrating hardware in tech products and the critical role of customer success in driving growth.

Todd Jackson, the new partner at First Round Capital, has a stellar tech background, having driven product strategies at Google, Facebook, Twitter, and Dropbox. Joining him is Phin Barnes, known for his insightful blog, sneakerheadVC. They delve into the journey of transitioning from founder to venture partner. Todd shares key learnings from his major roles in tech, while Phin offers advice on thriving in venture capital. They also discuss the challenges of generational shifts within firms and stress the importance of cultivating strong relationships to foster success in startups.

Alexa Von Tobel, Founder and Managing Partner at Inspired Capital, discusses her journey from launching LearnVest to leading NYC's largest female-led VC fund. She shares her unique approach to portfolio construction, including a strategy that segments investments into three buckets. Alexa also addresses the challenges of misalignment between VCs and founders, the delicate art of saying no, and the changing dynamics of fundraising timelines. Emphasizing that capital is no longer the only differentiator, she highlights the importance of relationships in venture capital.

Katie Stanton, Founder and General Partner of Moxxie Ventures, shares her remarkable journey from executive roles at tech giants like Yahoo and Google to becoming a solo GP. She discusses the challenges of raising her first fund, the critical lessons learned, and what she would do differently next time. Katie also tackles the rising trend of multi-stage funds entering seed rounds and offers advice for founders navigating these offers. Her insights on promoting diversity in investment and the emotional hurdles of the fundraising process make for an engaging discussion.

Rick Nucci, Co-founder and CEO of Guru, shares insights on building successful companies outside traditional tech hubs like San Francisco. He emphasizes the importance of a strong company culture, adapting values during growth, and effective hiring practices. Nucci discusses his leadership evolution, advocating for empathy and transparency while navigating challenges. He believes that promoting from within fosters a positive atmosphere and highlights the unique advantages of operating in non-tech locations for talent acquisition and growth.

Howard Marks, co-chairman of Oaktree Capital Management and author of "Mastering the Market Cycle," shares his invaluable insights gained from over five decades in finance. He reflects on how an early job rejection shaped his successful career. Marks discusses the significance of understanding market cycles and the importance of taking a contrarian approach during times of market fear. He emphasizes the need for cautious risk assessment while fostering effective partnerships within Oaktree, all amid the current economic landscape.

Sumeet Gajri, Chief Strategy Officer at Carta and Managing Partner at Original Capital, shares his journey from Scotland to the heart of venture capital in NYC. He discusses his unique approach to portfolio construction, emphasizing optimal sizing and loss ratios. Sumeet explains his strategy for investing in promising startups during "between rounds". He highlights the importance of distribution channels for success and the need for trust-building between investors and founders. His insights on capital concentration and navigating relationships make for an engaging listen.

Samir Kaul, Founding Partner at Khosla Ventures, shares insights from his extensive investment experience, including backing top startups like Square and Impossible Foods. He challenges the norm by arguing that pro-rata rights are a cop-out and emphasizes the importance of embracing technical risks. Kaul also dives into investment decision-making, stressing the need for a proactive mindset in volatile markets. He discusses balancing time allocation across portfolio companies and the evolving role of board members in fostering effective collaboration.

Kurt Rathmann, Founder and CEO of ScaleFactor, shares his journey from landscaping to revolutionizing bookkeeping with an automated solution. He discusses raising over $105 million in 13 months across three rounds and the mental shift from scarcity to abundance. Kurt emphasizes the critical role of venture capitalists, outlining five ways they can add real value. He also dives into building a strong company culture amidst rapid growth and shares insights on recruiting talent outside traditional tech hubs.