Driving Alpha

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.

(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 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.

(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

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 is the Founder of Boldstart Ventures, a true believer and partner from inception for bold founders reinventing the enterprise stack. Ed is currently on the boards of Snyk, BigID, Blockdaemon, Protect AI, Env0, and several other cybersecurity and infrastructure startups. Other notable inception investments include Kustomer, where he was on the board until his exit to Meta, Superhuman, Security Scorecard, and Front. Ed also co-founded MState in 2017, an enterprise blockchain lab in partnership with IBM, where seed investments include Fireblocks. He is known for being a partner from inception, helping founders start, scale, and exit while enjoying the process.

Ed has been recognized as a top 10 investor on the Forbes Midas Seed List for the last three years and as the No.1 seed investor in the Business Insider Seed 100 for 2023 and 2024. He also writes the popular weekly newsletter What's Hot in Enterprise IT/VC, which covers the latest trends in venture capital and enterprise technology. Prior to boldstart, Ed was a Co-founder of Dawntreader Ventures, where he led inception investments in Greenplum (sold to EMC, Pivotal — IPO), GoToMeeting (sold to Citrix), and LivePerson (IPO). He graduated from Harvard with a BA in Economics and was a four-year letterman on the men's lacrosse team.

(00:00) Introduction

(00:41) How Ed Sim's career blossomed over 25 years in the venture world

(02:40) What does it take to be a successful entrepreneur and investor?

(04:09) New York's evolution as a tech powerhouse and what it means for enterprise software

(07:13) How pre-seed and seed rounds came to be, and why we need Inception rounds

(11:33) How Ed's lacrosse background shaped his investment philosophy

(18:33) The importance of finding a balance between "steak" and "sizzle" in founders

(22:03) AI's future and how incumbent companies may compete or collaborate with startups

(25:49) An insider's advice on evaluating companies with "intuitive TAM"

(40:34) The key to sustained content creation discipline and its importance in venture capital

(54:28) Ed's long-term vision for boldstart ventures

What does crafting overnight success stories in the complex tech landscape take? Passion, resilience, and a sharp eye for pioneering technology can ignite the path to building billion-dollar enterprises. Can these same elements apply regardless of market conditions and trends?

Seasoned venture capitalist Ed Sim lays out his blueprint for venture capital triumph, infused with lessons learned from his early days selling kitchenware to standing at the helm of a game-changing tech investment firm. He highlights that the path to industry leadership is paved with a long-term vision, founder empathy, and a focus on problem-solving. With insights on how significant shifts reshaped the stage — such as the adoption of Amazon EC2 and open-source — Ed demonstrates a keen ability to anticipate and leverage the market's evolutionary trends. He offers invaluable guidance to aspiring venture capitalists and seasoned investors alike, proving that relentless commitment and strategic evolution withstand the test of time.

In this episode of Driving Alpha, Steve Brotman chats with Ed Sim, the Founder of boldstart ventures, about Ed's growth in venture capital and insights into modern tech investments. Ed shares the strategic thinking propelling his journey, emphasizing early participation in startups and an unwavering dedication to enterprise infrastructure. He also elaborates on the critical role his passion for sports and grit played in forging relationships and sustaining success through economic cycles.

Hans Swildens is the CEO and Founder of Industry Ventures and manages the overall business. As an early pioneer of the modern secondary market for venture capital, Hans created new ways to get liquidity for venture capital investments prior to an IPO or M&A event. Additionally, he was early to support the development of a new class of venture capital partnerships focused on seed and early-stage investing during the last decade. He directs the firm's investment processes, operations, and limited partner relationships. Earlier in his career, Hans was a successful entrepreneur who co-founded and acted as President of Microline Software. Microline was acquired by Blaze Software (IPO) and was subsequently acquired by Fair Isaac.

(00:00) Introduction

(01:24) The role of Industry Ventures in backing emerging venture capital firms

(02:54) Hans' unexpected transition from an entrepreneur to venture capital

(04:37) The success and sale of Hans' first company, Microline Software

(10:59) Hans uncovers the strategies and pivots behind the growth of Industry Ventures

(17:22) AI's potential impact on industries and innovation cycles

(22:23) Strategies for pitching to venture capitalists for new funds

(25:15) What are the three crucial types of successful VCs Swildens identifies?

(28:40) Work-life balance and its impact on success

(35:08) The nuances and critical importance of partnership dynamics and succession in venture capital firms

In a world where technology evolves faster than ever, is it possible to stay ahead of the innovation curve and reap sizable investment returns? Many investors struggle to adapt strategies while continuing to foster an entrepreneurial spirit, which is crucial for longevity and success in venture capital. How can LPs and VCs navigate these shifting sands without getting swallowed by the next big platform change?

Entrepreneur and venture capitalist Hans Swildens delves into his inspiring journey from tech entrepreneur to leading one of the top venture firms focused on small venture funds. Hans shares how he tackled the dotcom bubble's collapse by strategically pivoting from angel investing to secondary liquidity, ultimately growing his firm's footprint to $8 billion in committed capital. He outlines the inherent unpredictability in venture capital, the excitement around AI's potential to drive an extensive innovation cycle, and the value of maintaining work-life balance.

In this episode of the Driving Alpha podcast, Steve Brotman hosts Hans Swildens, CEO and Founder of Industry Ventures, for an insightful discussion about the unpredictable journey of venture capital investments and maintaining success amidst the challenges. Hans provides strategies for investment management success, highlights the entrepreneurial drive needed to create opportunities from market shifts, and champions the importance of work-life balance in sustaining a flourishing long-term career.

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.

(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

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.

(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?

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.

(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

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.