In this insightful episode of "Driving Alpha," host Steve Brotman sits down with Dror Nahumi, a seasoned General Partner at Norwest Venture Partners. Dror’s extensive experience spans operational roles, strategic investments, and guiding startups from seed stage to multi-billion dollar outcomes. He has a strong track record with investments in leading companies like Gong, Vast Data, and Weka.io, making him a key figure in the venture capital world.   Here’s a glimpse of what you’ll learn: 00:00 Introduction to Driving Alpha 00:27 Meet Dror: A Venture Capital Visionary 01:21 Dror's Journey to Venture Capital 02:38 The Role of Operational Experience in VC 04:22 Norwest Venture Partners: A Legacy of Success 05:56 Investing in Israeli and US Startups 08:15 Dror's Investment Strategy and Success Stories 12:51 Advice for Aspiring Entrepreneurs and VCs 17:18 Emerging Trends and Technologies 21:59 The Importance of Unique Value in VC 26:48 Conclusion and Final Thoughts   In this episode...  Dror Nahumi shares his journey from an engineering background to becoming a successful venture capitalist. He discusses the evolution of Israeli startups, highlighting how the go-to-market capabilities have improved significantly, leveling the playing field with U.S. companies. Dror offers a deep dive into his investment strategy, focusing on identifying unfair advantages and backing companies with the potential for substantial outcomes. We also explore his thoughts on emerging trends in AI, the importance of user interface innovation, and why some of the best investments come from the most debated opportunities. Dror provides valuable advice for both entrepreneurs and aspiring VCs, emphasizing the need for unique value propositions and deep market understanding.  

In this engaging discussion, Tim Draper, the founder of Draper Associates and a pioneer in venture capital, shares his journey and insights. He emphasizes the importance of diversification and viral marketing while dissecting emerging trends like AI's role in investment. Tim also explores futuristic markets, including advancements in healthcare and space travel, along with the rise of cryptocurrency. His optimistic views on how startups can disrupt monopolies highlight his belief in transformative entrepreneurship.

In the latest episode of the Driving Alpha podcast, Brian Smiga sits down with Raju Rishi, General Partner at RRE Ventures. Raju brings decades of experience in entrepreneurship and venture capital, sharing his deep knowledge of the tech landscape and investment strategies. At RRE Ventures, he specializes in sectors such as Enterprise Software, Artificial Intelligence, and Robotics, and has built a strong track record in scaling successful startups.   Here’s a glimpse of what you’ll learn: 00:00 Introduction to the Podcast and Guest 00:35 Raju Rishi's Early Career and Background 04:00 Transition to Venture Capital 04:42 RRE's Investment Strategy and Market Insights 07:52 Thesis-Driven Investing and Sector Analysis 11:55 Fund Structure and Seed Investments 14:15 Incubating Startups and Proprietary Deal Flow 19:09 Raju's Personal Unfair Advantage 25:32 The Fourth Inflection Point: AI 32:01 Conclusion and Final Thoughts   In this episode... Raju Rishi discusses the evolving venture capital landscape, highlighting how RRE Ventures approaches sector analysis to identify potential high-growth investments. He explains the process behind selecting venture bets, which involves rigorous research and strategic timing decisions. The conversation covers how RRE leverages long-standing relationships and proprietary deal flow to stay ahead in the competitive VC space. The episode also dives into the common patterns seen in major technological shifts, from the advent of personal computers to the rise of mobile technology. Raju outlines the factors that drive such transformations and the opportunities they create for investors. Additionally, he shares RRE's approach to working with trusted entrepreneurs, often incubating companies and guiding founders toward market success.

In this episode of the Driving Alpha podcast, Brian Smiga sits down with Jeffrey Berman, a partner at Camber Creek, to discuss the intricacies of investing in real estate tech. Jeffrey brings his unique background as a venture capitalist and former real estate professional to the table, sharing insights into what sets top-performing VC firms apart, how to identify venture-scale opportunities, and the importance of domain expertise in the built world. Here’s a glimpse of what you’ll learn: 00:00 Introduction to Driving Alpha Podcast 00:44 Jeffrey Berman's Unique Investment Philosophy 01:48 The Secret Sauce of Camber Creek 04:00 Investment Criteria and Decision-Making 07:14 Geographical Insights and Market Penetration 10:52 Personal Insights and Fitness 12:20 Current and Future Investment Opportunities 23:32 Closing Remarks and Future Plans In this episode... The conversation kicks off with Jeffrey explaining Camber Creek's investment strategy, which is built on the firm’s deep real estate roots and its network of over 300 real estate developers and owners. He shares how this access provides a competitive advantage when evaluating potential investments, offering insights that generalist VCs might overlook. Jeffrey also discusses the power of the “network effect” in real estate tech, where leveraging connections can dramatically impact the success of portfolio companies. Brian and Jeffrey further explore the concept of "geographic singularity," highlighting the challenges of scaling a solution that works in one market, such as New York, but may not easily translate to other locations. They also touch on the role of alternative materials, AI, and financial wellness in shaping the future of the real estate tech landscape. Throughout the episode, Jeffrey provides practical advice for both investors and founders on navigating market cycles and overcoming the hurdles of selling into the real estate sector.  

Leura Craig is the founder and managing partner at Outlander VC, a venture capital firm specializing in pre-seed and seed-stage investments. A former operator turned investor, Leura brings her entrepreneurial experience to venture capital, having previously bootstrapped and scaled two startups, including L&W, which raised $30M from top investors like CRV and Benchmark. Leura is passionate about discovering diverse founders from unconventional markets, and her current focus includes sectors like AI, hardware/robotics, and the future of work. Recognized as a Forbes 30 Under 30 and named one of Goldman Sachs’ “100 Most Intriguing Entrepreneurs,” Leura is reshaping how early-stage venture is done.   Here’s a glimpse of what you’ll learn: 00:00 Introduction to Laura Craig 00:17 From Designer to Venture Capitalist 00:52 The Value of Operator Experience in VC 03:24 Outlander's Unique Founder Framework 05:36 Outlander's Impressive Track Record 07:01 The Origin Story of Outlander Ventures 12:55 Ruthless Prioritization for Founders 14:43 Fund 3 and Investment Strategy 20:32 The Importance of Trust and Honesty 24:06 Conclusion and Future Outlook   In this episode... How does operational experience transform a venture capitalist’s approach to investing? Leura Craig, founder of Outlander VC, shares her journey from a successful founder to managing a venture capital firm that focuses on early-stage startups. With a reputation for identifying and nurturing high-potential founders, Leura emphasizes the importance of understanding the founder's mindset and building long-term trust. Leura explains how Outlander VC uses a proprietary 38-point framework to evaluate founders, going beyond traditional metrics to focus on human attributes like resilience, vision, and adaptability. In this conversation, she discusses how trust and open communication are central to Outlander's philosophy and shares lessons from investing in 18 multibillion-dollar companies. The episode also delves into why the next few years represent a unique opportunity for first-check investors, particularly in sectors like AI, hardware, robotics, and the future of work. Leura stresses the importance of disciplined investing, prioritizing ownership, and focusing on building diverse portfolios that reflect the changing landscape of venture capital.

Matthew Greenfield is a Managing Partner at Rethink Education, a venture capital firm dedicated to innovative educational technology. He holds multiple board seats, including at SNHU and BrightBytes, and has co-founded several successful technology companies, such as near-unicorn Rethink First. An accomplished educator and thought leader with a BA, MA, and PhD from Yale, he is former professor at Bowdoin College and the City University of New York. Episode Chapters   (00:00) Introduction (01:57) How familial influences shaped Matthew Greenfield's passion and direction in venture capital (02:30) The impact of female venture partners in Matt’s father’s VC journey (06:04) How Matt leveraged his background for Rethink Education's mission (06:42) The importance of relationship-building for venture capital investments (09:27) Matt illustrates the power of strategic advice and networking through Rethink First’s success story  (11:08) The key to being a successful VC: recycling people (16:50) How to be a good giver without letting it overwhelm you (18:45) Adapting an open-minded, unbiased approach to discovering innovation (23:37) The intersection of product-market fit, addressing genuine human needs, and venture capital success In this episode… In the fast-paced world of startups and funding, maintaining and rejuvenating relationships can be as valuable as the capital itself. This cyclical nature of relationships helps VCs stay connected with past successes and ensures they remain relevant in an ever-evolving market. How can you leverage relationships in the venture capital ecosystem to achieve outsized investment returns? Matthew Greenfield, an ex-professor turned venture capital partner, shares how strategic relationships, mentorship, and candid guidance have shaped his approach to nurturing successful enterprises. Highlighting the importance of targeting real human problems for venture growth, Matt emphasizes assisting aspiring technologists and executives while being open to innovation from unexpected sources. Whether reconnecting with a successful founder for a new project or leveraging an old network to discover the next big idea, recycling relationships is a powerful tool for long-term success in the venture capital landscape. Matt’s reflections underscore the power of embracing innovation from all corners and honest feedback's transformative impact on founders and investors alike. In this episode of the Driving Alpha Podcast, Brian Smiga chats with Matthew Greenfield, Managing Partner at Rethink Education, about shaping the future of education and venture success. Matt dives into his transition from academia to venture capital, the importance of building a diverse network of investors, and how to strengthen trust through constructive feedback to entrepreneurs. He also explores the concept of “thrifty recycling” and the benefits of CRMs for tracking and nurturing connections.

Rebecca Kaden is a Managing Partner at Union Square Ventures, a New York-based venture capital firm. She began her career as a journalist, and prior to USV, was a General Partner at Maveron, a consumer-focused early-stage fund. Rebecca was born in New York City. She studied English and American Literature at Harvard and received her MBA from Stanford. Episode Chapters (00:00) Introduction (2:46) Rebecca Kaden highlights the role of early mentorship in a successful VC career (6:27) How Rebecca’s liberal arts background influences her VC perspectives (8:29) Union Square Ventures' thesis-driven approach to investing (15:00) USV's investment strategy in the healthcare sector (17:04) How USV collaborates with other VCs and values syndicate participation (22:04) Why should investors prioritize businesses with unconventional models? (26:42) The philosophy behind the concept of "high conviction, low velocity" investing (33:42) USV’s unwavering commitment to decentralization and the future of blockchain investments (39:42) Rebecca’s advice for junior VCs In this episode… Can high-conviction investments yield the results venture capitalists strive for? What does it take to pursue an unusual and non-competitive market? With a deep understanding of the industry, a journalist turned VC specialist brings a unique perspective to the untapped potential in sectors like healthcare and the revolutionary applications of AI and blockchain technology. In this episode of Driving Alpha, Steve Brotman chats with Rebecca Kaden, Managing Partner at Union Square Ventures, about the strategies that drive USV's investment philosophy. Rebecca dives into the value of thesis-driven investments, USV’s unwavering commitment to decentralization, and the future of blockchain investments. She also explores the importance of mentorship, collaborating with other VCs, and a deep understanding of markets.  Mentored by Bill Campbell, Rebecca Kaden leverages her journalism background and business acumen to drive investment in companies reshaping entire industries. Her insights into Union Square Ventures’ thesis-driven investment approach reveal how low investment velocity along with high conviction can make all the difference. From innovative healthcare companies like Thirty Madison to unconventional investments in platforms like Team Shares, USV’s philosophy centers on finding and nurturing non-traditional opportunities. With a significant portion of the firm’s portfolio dedicated to decentralization and cryptocurrency, Rebecca highlights how investors can cultivate a portfolio characterized by strong conviction and innovative solutions by staying informed on emerging technologies.

Ed Sim, founder of boldstart ventures and a prominent venture capitalist, discusses the art of inception investing in enterprise technology. He highlights the evolution of New York's startup ecosystem, underlining the importance of personal relationships for capital raising. Ed shares insights on the traits of successful founders and the complex challenges of investing in cybersecurity. He also delves into the impact of AI on enterprises and the need for innovative solutions to address evolving technological threats.

Hans Swildens, founder of Industry Ventures, discusses staying ahead in venture capital, navigating tech evolution, and adapting strategies for success. He shares insights on balancing work-life, managing partnerships, and building relationships in the industry.

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.