Driving Alpha

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 Leura 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.

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.

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.