Driving Alpha

Alpha Partners

This is the Driving Alpha, where we feature our friends, the out-performing investors, who demonstrate their path to driving alpha, or out-sized investment returns. We’re Alpha Partners, where we partner with a thousand early-stage venture firms as their opportunity capital to invest in their best companies. read less

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Driving Alpha: Seed Stage Investing and the Importance of Pro Rata Rights with Jason Calacanis

Driving Alpha: Seed Stage Investing and the Importance of Pro Rata Rights with Jason Calacanis

Jason Calacanis is the Founder and CEO of early-stage investment firm LAUNCH and real-time business news app Inside.com. A serial entrepreneur, angel investor, and former Sequoia Capital scout, Jason has invested in hundreds of startups, including Uber and Calm, a meditation app now valued at $1 billion. He previously launched Venture Reporter — formerly known as Silicon Alley Reporter — and Weblogs, Inc., which he exited before venturing into angel investing. Jason continues to shape and influence the tech and investment spheres, sharing invaluable insights through his acclaimed book Angel and podcasts This Week in Startups and All-In. His platform Founder University helps founders get funding and launch their products. Episode Chapters: (00:00) Introduction (01:24) Jason Calacanis shares his experiences as a prolific seed investor (05:54) How Jason’s Silicon Alley Reporter grew to $12 million in revenue during the dot-com boom (09:15) The importance of asking insightful questions to uncover a founder’s potential (12:51) Jason reflects on past investments, including Uber and Open Angel Forum (14:46) What are the “three Ds” of identifying winners? (25:24) What are the criteria for identifying successful founder-led companies? (48:33) Jason explains at-scale seed investing strategy, signaling issues, and beta (55:44) Jason’s journey to starting LAUNCH Festival after breaking away from Sequoia Capital (01:10:30) AI adoption in startups, investment climate, and mobile technology In this episode… Investing in startups at the seed stage offers immense potential for growth and innovation, but it comes with hurdles and complexities. From portfolio construction to day-to-day management, navigating this terrain requires a keen understanding of the market, a discerning eye for talent, and a strategic approach to decision-making. What can you learn from a technology entrepreneur whose early-stage investments have achieved billion-dollar valuations? Angel investor Jason Calacanis navigates the complexities of early-stage startups with his 21-person team, serving as a catalyst for hundreds of thriving companies. Drawing from his extensive experience, he delves into the nuances of seed-stage investing, highlighting key factors essential for a successful venture capital firm and the critical importance of identifying exceptional talent and groundbreaking ideas. Additionally, investors must understand potential warning signs that could signal a startup's failure and seek mentorship from experienced investors. Jason also highlights the value of a world-class design and a product outlier in driving sustained growth and market dominance. In this episode of the Driving Alpha podcast, Steve Brotman sits down with Jason Calacanis, the CEO and Founder of LAUNCH and Inside.com, to explore the intricacies of seed-stage investing. Jason shares his experience as an angel investor, insights regarding venture capital and startups, and highlights the crucial role of mentorship from experienced investors.

Episodes

Driving Alpha: Seed Stage Investing and the Importance of Pro Rata Rights with Jason Calacanis

Driving Alpha: Seed Stage Investing and the Importance of Pro Rata Rights with Jason Calacanis

Jason Calacanis is the Founder and CEO of early-stage investment firm LAUNCH and real-time business news app Inside.com. A serial entrepreneur, angel investor, and former Sequoia Capital scout, Jason has invested in hundreds of startups, including Uber and Calm, a meditation app now valued at $1 billion. He previously launched Venture Reporter — formerly known as Silicon Alley Reporter — and Weblogs, Inc., which he exited before venturing into angel investing. Jason continues to shape and influence the tech and investment spheres, sharing invaluable insights through his acclaimed book Angel and podcasts This Week in Startups and All-In. His platform Founder University helps founders get funding and launch their products. Episode Chapters: (00:00) Introduction (01:24) Jason Calacanis shares his experiences as a prolific seed investor (05:54) How Jason’s Silicon Alley Reporter grew to $12 million in revenue during the dot-com boom (09:15) The importance of asking insightful questions to uncover a founder’s potential (12:51) Jason reflects on past investments, including Uber and Open Angel Forum (14:46) What are the “three Ds” of identifying winners? (25:24) What are the criteria for identifying successful founder-led companies? (48:33) Jason explains at-scale seed investing strategy, signaling issues, and beta (55:44) Jason’s journey to starting LAUNCH Festival after breaking away from Sequoia Capital (01:10:30) AI adoption in startups, investment climate, and mobile technology In this episode… Investing in startups at the seed stage offers immense potential for growth and innovation, but it comes with hurdles and complexities. From portfolio construction to day-to-day management, navigating this terrain requires a keen understanding of the market, a discerning eye for talent, and a strategic approach to decision-making. What can you learn from a technology entrepreneur whose early-stage investments have achieved billion-dollar valuations? Angel investor Jason Calacanis navigates the complexities of early-stage startups with his 21-person team, serving as a catalyst for hundreds of thriving companies. Drawing from his extensive experience, he delves into the nuances of seed-stage investing, highlighting key factors essential for a successful venture capital firm and the critical importance of identifying exceptional talent and groundbreaking ideas. Additionally, investors must understand potential warning signs that could signal a startup's failure and seek mentorship from experienced investors. Jason also highlights the value of a world-class design and a product outlier in driving sustained growth and market dominance. In this episode of the Driving Alpha podcast, Steve Brotman sits down with Jason Calacanis, the CEO and Founder of LAUNCH and Inside.com, to explore the intricacies of seed-stage investing. Jason shares his experience as an angel investor, insights regarding venture capital and startups, and highlights the crucial role of mentorship from experienced investors.

Driving Alpha: Redefining Venture Capital and the Future of AI with Steve Brotman and Ron Insana

Driving Alpha: Redefining Venture Capital and the Future of AI with Steve Brotman and Ron Insana

Steve Brotman is the Managing Partner at Alpha Partners, a company that co-invests with the world’s best VCs by sharing economics with early-stage VCs. With extensive experience in venture capital, Steve co-founded and managed venture capital firms such as Greenhill SAVP and Silicon Alley Venture Partners, with notable investments in companies like LivePerson and Medidata Solutions. His entrepreneurial journey began with AdOne, a venture-backed company that revolutionized online classified advertising and garnered significant industry recognition. A recipient of multiple accolades, Steve has been named in Crain's Tech 100 and 40 Under 40 among New York business leaders. Episode Chapters: (00:00) Introduction (00:36) Steve Brotman reflects on launching the Driving Alpha podcast (01:59) Steve discusses venture capital trends (02:50) Changing the venture capital model to benefit both parties (04:02) Why Steve partners with 850 VCs to provide funding for technology companies (04:27) AI's potential impact on jobs and industries (13:00) How has technology influenced the democratization of education? (18:00) What is the future of biotech and an AI-driven society? In this episode… Venture capital, an ever-evolving landscape, serves as the engine driving innovation and growth in the tech realm. How can investors in this space harness technology for positive societal impact while navigating ethical considerations? Venture capitalist Steve Brotman delves into the future of VC, highlighting the transformative impacts of emerging technologies like AI. As the discussion extends to early-stage investments in drone and robotics companies, Steve explores the ethical considerations surrounding autonomous driving and the prospect of robots serving humans in the future. By prioritizing ethical considerations, venture capital can emerge not only as a vehicle for financial gain, but as a catalyst for innovation that balances progress with social responsibility, shaping a future where technology serves humanity's collective interests. In this episode of the Driving Alpha podcast, we flip the script as veteran journalist Ron Insana interviews Steve Brotman, podcast host and Managing Partner at Alpha Partners. They discuss the evolving models of venture capital, AI’s benefits and potential impact on the VC ecosystem, and the viability of biotech investments.

Driving Alpha: Exploring Early Tech Ventures and the Evolution of Financial Media with Ron Insana

Driving Alpha: Exploring Early Tech Ventures and the Evolution of Financial Media with Ron Insana

Ron Insana is an award-winning financial analyst and commentator at CNBC, where he shares insights into economic trends. In addition to writing for Money magazine and USA Today, Ron has hosted two nationally syndicated radio programs. He previously served as the CEO of Insana Capital Partners, which, at its peak, managed the $125 million Insana Capital Partners "Legends Fund.” With a background in film production, he ventured into financial reporting in 1984, eventually becoming a regular anchor at CNBC. Ron has authored four books on investing and is recognized as one of the "Top 100 Business News Journalists of the 20th Century." He is a sought-after lecturer on economics and financial markets, graduating with honors from California State University Northridge. Episode Chapters: (00:00) Introduction (05:37) Ron Insana’s journey climbing the ranks of the media industry (09:37) The impact of the Great Recession (11:21) Ron recounts interviews with Bill Clinton, Warren Buffett, and Steve Jobs (15:26) What is the future of financial media? (19:18) The impact of new technologies like AI on news reporting (23:25) The intersection of US politics, economy, and media (24:21) Ron’s thoughts on the US financial market In this episode… Financial media has come a long way in a short span of time in the transition from traditional to digital platforms. This shift has led to the ubiquity of newer formats such as online news sites, podcasts, and social media influencers. How has this transformation changed the way we access financial information, and what does it mean for the future? With a career spanning the early days of CNBC to the present, Ron Insana, a veteran financial analyst and commentator, has witnessed this transformation firsthand. Reflecting on the pioneering days of financial news networks, he highlights the profound shift toward accessibility and interactivity. However, while technological advancements offer new opportunities for engagement and outreach, the proliferation of misinformation and the increased politicization of news present formidable challenges. With the rise of AI-based fintech platforms and the fragmentation of media consumption habits, financial media outlets are challenged to adapt to changing consumer preferences while maintaining the integrity and credibility of their content. In this episode of the Driving Alpha podcast, Steve Brotman discusses the evolution of financial media with media veteran Ron Insana. The two discuss Ron’s media career trajectory, emerging trends in financial media, ethical considerations regarding the use of AI, and the intersection of US politics, economy, and media.