Driving Alpha
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.
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Francisco Gimenez (8VC) on Spotting Biotech Unicorns Others Miss
07/16/2025
Francisco Gimenez (8VC) on Spotting Biotech Unicorns Others Miss
Francisco Gimenez, Partner at 8VC, shares his unconventional journey from Stanford PhD to venture capital, where he leads investments in Bio-IT and enterprise AI. Known for his technical background and sharp instincts, Francisco has been pivotal in backing startups pushing the boundaries of biotech and healthcare innovation. Here’s a glimpse of what you’ll learn: 00:48 Introduction to Driving Alpha 01:18 Meet Francisco Gimenez: A Journey from Academia to Venture Capital 02:45 Francisco's Early Career and Academic Background 04:02 Joining Formation Eight and Transition to 8VC 06:18 Investing in Visionary Founders and Unique Companies 08:26 Challenges and Insights in Deep Tech and Biotech Investing 12:15 The Importance of Problem-Oriented Founders 19:51 Exciting Companies and Future Prospects 20:41 Engineering Principles in Biologics 22:26 Innovative Cell Biology Tools 23:36 Biological Foundation Models and AI 24:52 VC Perspective on Biotech and Pharma 26:00 Challenges in Biotech Innovation 33:50 NIH Funding and Indirect Costs 39:13 Advice for Aspiring VCs and Founders 42:20 Conclusion and Final Thoughts In this episode, Francisco unpacks how he spots the kinds of biotech companies others overlook, those “end-of-one” startups tackling massively complex problems with groundbreaking approaches. He explains why he focuses on founders driven by a deep obsession with solving difficult problems, rather than chasing trends or easy wins. The discussion explores the future of biotech, with insights into companies like Big Hat Biosciences and Seleno Therapeutics, pioneers at the intersection of AI and biology. Francisco explains why applying engineering and iterative design principles to the life sciences is unlocking new frontiers in drug development. He also offers his take on NIH funding controversies and shares why decentralized biotech innovation could spark the next wave of transformative therapies.
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AI Meets Venture: Ben Orthlieb (Blue Moon) on Outperforming Traditional VCs
06/25/2025
AI Meets Venture: Ben Orthlieb (Blue Moon) on Outperforming Traditional VCs
What if AI could predict which founders will build billion-dollar companies? Ben Orthlieb, co-founder of Blue Moon, is doing just that, using AI and behavioral science to consistently outperform even the top VC firms. With roots at LinkedIn and Emergence, Ben brings a rigorous, founder-first model to seed investing. Here’s a glimpse of what you’ll learn: 00:00 Intro to Driving Alpha 00:41 Meet Ben Orthlieb of Blue Moon 01:20 Why “2.12” wasn’t working—and how “Blue Moon” captures their true identity 02:05 The meaning behind both names—and what they signal to founders 03:45 Ben’s origin story: building a new kind of VC from first principles 05:30 Why traditional VC falls short—and how Blue Moon is breaking the mold with AI 10:45 Graduation rates as the ultimate seed-stage performance metric 12:00 How Blue Moon wins deals with small checks and a founder-first approach 20:20 Meet Agatha and Da Vinci: the AI agents powering Blue Moon’s edge 23:05 Strategic collaborations and the expanding Blue Moon network 26:50 What’s next for Blue Moon—and how to engage as a founder, VC, or LP In this episode, Ben reveals how Blue Moon evaluates over 9,000 startups a year using their proprietary AI agents, Agatha and Da Vinci, to uncover the top 300 teams with the highest potential. The firm’s two-meeting investment process, rooted in deep founder analysis and cutting-edge tech, allows Blue Moon to move faster and smarter than traditional firms, achieving seed-to-Series A graduation rates nearly 3x higher than the market. We also explore why the firm rebranded from 2.12 to Blue Moon, the psychology behind founder decision-making, and how their tools give them a near-unfair advantage in sourcing, vetting, and supporting startups. If you’re a founder, VC, or LP curious about the future of venture capital, this conversation is a must-listen.
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Brice Penaud & Jonathan Taylor of Water Bear Ventures: Investing in Resilience and Founder Grit
06/12/2025
Brice Penaud & Jonathan Taylor of Water Bear Ventures: Investing in Resilience and Founder Grit
What if the key to outsized venture returns isn’t just a great idea but the unshakable resilience of the founder behind it? Jonathan Taylor and Brice Penaud of Water Bear Ventures believe grit is the ultimate differentiator, and they’ve built a fund around finding it. Jonathan brings years of experience driving strategic outcomes in venture, while Brice draws on a behavioral science background to decode the mindset of top-tier founders. Here’s a glimpse of what you’ll learn: 00:00 Introduction to Driving Alpha 00:43 Meet the Water Bear Team 02:15 The Origin of Water Bear Ventures 05:29 Defining Exponential Value 08:19 Art Meets Science in Early-Stage Investing 11:06 Building Relationships and Measuring Grit 16:44 Hunting Grounds for Gritty Founders 18:40 Involvement Beyond Capital 23:14 Lessons from Fund One and Plans for Fund Two 32:49 Optimizing LP Relationships 37:52 Future Vision for Water Bear Ventures 40:47 Conclusion and Final Thoughts In this episode, Host Sam Silvershein sits down with the Water Bear Ventures team to explore how they invest in adaptability, grit, and long-term value creation at the earliest stages. From the origins of their firm’s name to the behavioral cues they use to identify resilient founders, Jonathan and Brice reveal the real mechanics of building a differentiated early-stage portfolio. You’ll hear how Water Bear's founder-first, anti-hype approach helped them outperform with Fund I and how those lessons are shaping their strategy for Fund II. They also break down how they build trust with LPs, support founders beyond capital, and maintain focus in a landscape full of distractions. If you want a deeper understanding of what makes early-stage investing work, this conversation delivers.
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From Google to Nava: Manish Patel’s playbook for Series A investing
06/04/2025
From Google to Nava: Manish Patel’s playbook for Series A investing
What does it take to turn early traction into scalable momentum? And how do you know if your startup—and your engine—is even built for venture capital? Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha Podcast 02:20 Meet Manishh Patel: From Google to Nava Ventures 03:17 Growing Up in Rural Kentucky 05:24 The Journey to Venture Capital 08:17 Founding Nava Ventures 16:22 The Series A Focus 19:57 Building the Flywheel: Operational Infrastructure 20:41 Refining the Business Model 22:30 Hiring and Team Dynamics 22:52 The Importance of Closing Learning Loops 25:07 The Role of Venture Capital in Building Companies 28:22 Advice for Founders on Raising Venture Capital 35:07 Vetting Venture Capitalists 38:31 Final Thoughts and Contact Information In this episode, Host Zoe van den Bol sits down with Manish Patel, managing partner at Nava Ventures, for a candid and insightful conversation on what really matters at the Series A stage. Manish shares his journey from rural Kentucky to Google PM, to building Nava Ventures into one of the most focused Series A firms in the game. With lessons drawn from his operating days and years of backing breakout companies, this is a must-listen for founders, investors, and anyone building in early-stage tech. They also discussed why Series A is the most critical inflection point for a startup, how to build a real “flywheel” for growth, and when venture capital acts like fuel—or becomes a liability. Manish also shares what he looks for in founders, how Nava’s high-conviction, low-velocity model gives them an edge, and the key signals that differentiate enduring companies from fast, flashy ones.
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Eric Engineer of S3 Ventures: VC to CEO to VC—Lessons in Operating and Investing
05/22/2025
Eric Engineer of S3 Ventures: VC to CEO to VC—Lessons in Operating and Investing
Can deep operational experience shape better venture outcomes? One VC proves it can—drawing from years in the founder seat to back today's most promising startups. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha Podcast 01:05 Eric's Background and Career Journey 03:45 Transition to Venture Capital 06:27 Eric's Role at S3 Ventures 07:19 Investment Philosophy and Market Insights 12:12 Texas Venture Ecosystem 20:18 S3 Ventures' Unique Structure 29:56 Advice for Entrepreneurs and VCs 33:10 Conclusion and Final Thoughts In this episode, Eric Engineer, Partner at S3 Ventures, shares his journey from tech operator to venture investor. With roots in software engineering, leadership roles at Microsoft, and experience as a startup CEO, Eric offers a rare lens on what founders really need to succeed. He reflects on the emotional toll of entrepreneurship, the critical value of founder resilience, and how those experiences influence his approach to investing. The conversation also explores the evolution of the Texas startup ecosystem, S3 Ventures’ unique single-LP structure, and the nuanced decision-making process within the firm. Eric outlines what excites him most about AI’s impact on SaaS and healthcare and why startup longevity and team-building remain core to his investment thesis. For anyone curious about what it takes to win in venture—both as a founder and investor—this episode is full of actionable insight.
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Building billion-dollar hubs beyond Silicon Valley with Aziz Gilani from Mercury
04/23/2025
Building billion-dollar hubs beyond Silicon Valley with Aziz Gilani from Mercury
Can Middle America become the next innovation powerhouse? Aziz Gilani, General Partner at Mercury, thinks so—and he’s proving it by backing cloud and enterprise software startups across Houston and beyond. With a track record that includes major exits like Black Lotus and Modus, Aziz has helped Mercury’s portfolio reach over $9 billion in enterprise value. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha 00:51 Meet Aziz Gilani: Venture Powerhouse 02:08 Aziz's Journey to Venture Capital 04:20 Houston: A Hub for Enterprise Software 05:37 The Evolution of Texas's Startup Ecosystem 06:29 What VCs Look for in Entrepreneurs 10:29 The Growth of the Venture Capital Industry 15:38 The Impact of Regulations on Startups 24:29 Future Opportunities in Technology 31:41 Connecting with Aziz and Mercury Fund 34:29 Conclusion and Final Thoughts In this episode, Aziz joins Steve Brotman to unpack how Mercury is scaling venture success outside traditional hubs. He shares the journey that led him from early enterprise software gigs to shaping national innovation policy. Along the way, Aziz discusses the rise of Texas as a startup epicenter, fueled by domain-specific advantages and the growing infrastructure led by institutions like Rice University’s Ion. Aziz dives deep into what he looks for in founders—those with a “spike” of excellence—and why massive market potential, tenacity, and adaptability are essential. The conversation also explores the explosive growth of venture capital as an industry, the evolving regulatory landscape, and why now is a critical moment for sectors like AI, cybersecurity, and quantum computing. If you want insight into how to build capital-efficient, billion-dollar companies outside the coasts, this episode is a must-listen.
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Venture Cycles and Hard Lessons with Matt McIlwain (Madrona)
04/10/2025
Venture Cycles and Hard Lessons with Matt McIlwain (Madrona)
Matt McIlwain, Managing Director at Madrona, has spent over two decades investing in intelligent applications and driving innovation in AI. With a track record including Smartsheet, Apptio, and Isilon, he brings rare perspective from 25 years in venture capital. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha Podcast 00:57 Guest Introduction: Matt McElwain from Madrona 01:41 Matt's Journey into Venture Capital 03:06 Early Years at Madrona and the Dot-Com Bust 04:45 Madrona's Investment Strategies and Success Stories 06:29 Driving Alpha for Portfolio Companies 09:34 Evaluating Founders: The Power of Why 24:49 Navigating Exits and M&A Landscape 28:25 Life Lessons and Long-Term Perspective 32:40 Conclusion and Future Outlook In this episode Matt recounts his unconventional entry into venture capital—from auto parts to Amazon-era Seattle—and how he joined Madrona just before the dot-com crash. He reflects on the firm’s resilience through market downturns, the evolution of their early-stage to acceleration-stage investment strategy, and how conviction-driven bets like Isilon and Smartsheet became fund-makers despite difficult timing. Matt breaks down his “power of why” framework for evaluating startups, emphasizing founder-market fit and the value of long-term thinking. He shares candid insights into Madrona’s hands-on approach with founders, how he spots extraordinary teams, and why curiosity is the ultimate trait in successful entrepreneurs. From navigating exits in today’s M&A climate to building enduring partnerships, this conversation is a masterclass in venture capital longevity.
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Investing in Tomorrow: Lisa Chai of Interwoven Ventures on AI and Robotics
03/20/2025
Investing in Tomorrow: Lisa Chai of Interwoven Ventures on AI and Robotics
Lisa Chai, co-founder and general partner at Interwoven Ventures, joins Driving Alpha to discuss how robotics and AI are transforming industrial technology. With a deep background in venture capital and public markets, Lisa shares her insights into the megatrends driving automation, reshoring, and industrial AI. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha Podcast 00:53 Meet Lisa Chai of Interwoven 01:10 Interwoven's Focus and Investment Strategy 02:04 Lisa Chai's Origin Story 06:24 Challenges and Gender Dynamics in Venture Capital 08:57 Advice for Women in VC 10:54 Industrial Tech and Megatrends 16:51 Tech Infrastructure and Human-Robot Interaction 20:20 Spotlight on Portfolio Companies 23:13 Why Founders Should Choose Interwoven 25:33 Conclusion and Fundraising Announcement In this episode, Lisa dives into the key forces shaping the future of robotics and AI, from workforce automation to the role of government funding in reshoring supply chains. She highlights how Interwoven Ventures uniquely supports founders in this space, offering deep domain expertise and an extensive ecosystem. Lisa also shares her journey into venture capital, advice for women in the industry, and why she believes we are in the early innings of a massive industrial transformation.
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Bob Ackerman of AllegisCyber Capital: Cybersecurity Investing and AI Threats
03/12/2025
Bob Ackerman of AllegisCyber Capital: Cybersecurity Investing and AI Threats
Bob Ackerman saw the future of cybersecurity before the market did. As the founder of AllegisCyber Capital, the first venture firm dedicated 100% to cybersecurity, and the co-founder of DataTribe, he’s been at the forefront of investing in cyber defense. With a 20+ year track record, Bob has backed some of the most cutting-edge cybersecurity companies, navigating the intersection of venture capital, AI, and national security. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha 01:00 Meet Bob Ackerman: Cybersecurity Visionary 02:15 The Birth of AllegisCyber 06:00 The Importance of Domain Mastery in Cybersecurity 07:17 Collaboration Between DataTribe and AllegisCyber 12:49 AI's Impact on Cybersecurity 19:23 The Future of Network Security 23:46 Investment Opportunities in Cybersecurity 30:35 Challenges and Advice for Cybersecurity Founders 40:25 Conclusion and Final Thoughts In this episode Bob Ackerman sits down with host Sam Silversheen to discuss the evolution of cybersecurity investing and the role of AI in both offensive and defensive strategies. He shares the early insights that led him to focus exclusively on cybersecurity, why domain mastery is essential for both entrepreneurs and investors, and how he identifies non-consensus bets that others miss. Bob also explores the increasing sophistication of cyber threats, from AI-driven attacks to vulnerabilities in critical infrastructure. He explains why cybersecurity is an ever-evolving challenge, how startups can stay ahead of the curve, and what the future holds for cybersecurity investments. If you're in venture capital, tech, or cybersecurity, this episode is packed with insights you won’t want to miss.
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From Law to VC: David Hornik’s Journey to Lobby Capital
02/26/2025
From Law to VC: David Hornik’s Journey to Lobby Capital
David Hornik, founding partner at Lobby Capital, has spent over 25 years shaping the venture capital landscape. Formerly a lawyer with degrees from Stanford and Harvard, David transitioned into venture capital, making early bets on companies like Splunk, Build.com, and GitLab. His career is marked by a passion for helping founders, fostering strong industry relationships, and identifying high-potential investments. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha Podcast 01:57 Meet David Hornick: From Law to Venture Capital 03:43 Early Ventures and Key Investments 07:35 The Importance of Getting Lucky Early 09:44 Big Wins and Missed Opportunities 17:26 The Lobby Conference: Building Relationships 21:36 Adding Value as a VC 25:12 Psychology in Venture Capital 27:21 Conclusion and Final Thoughts In this episode David shares how his background in law unexpectedly led him to venture capital and how he navigated the early years of his career. He discusses the importance of getting lucky early, but also how hard work and strategic networking can help VCs manufacture their own luck. David also opens up about his biggest investment wins—such as Splunk’s $30 billion acquisition—and the key deals he missed, including early opportunities with Facebook and Uber. He dives into his passion for building meaningful relationships through the Lobby Conference, an exclusive networking event that has connected some of the biggest names in tech and venture capital. Finally, he explains why psychology and emotional intelligence are just as critical as technical knowledge in evaluating and supporting startups.
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Laura Chau of Canaan: Navigating Consumer Tech and AI
02/19/2025
Laura Chau of Canaan: Navigating Consumer Tech and AI
Laura Chau is a Partner at Canaan, where she leads investments in consumer technology and commerce tech. With over a decade of experience in venture capital, Laura has backed companies like Clutch, Ollie, Mischief, Solvely, and Nagish. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha 01:07 Guest Introduction: Laura Cho 02:58 Laura's Background and Career Path 05:35 Investment Strategies and Notable Companies 09:26 The Role of AI in Venture Capital 20:20 Traits of Successful Entrepreneurs 22:44 Geographical Trends and Future Outlook 32:10 Closing Remarks and Final Thoughts In this episode... In this episode, Laura shares her journey into venture capital, from her early career at Deloitte and Kabam to becoming a key player in consumer tech investing. She discusses the role of AI in shaping new opportunities, the power of storytelling in fundraising and hiring, and how successful founders build communities around their vision. Laura also provides insights into emerging trends in AI-driven consumer tech, strategies for differentiation in a crowded market, and the importance of go-to-market expertise. Whether you're an investor or an entrepreneur, this episode is packed with valuable takeaways on navigating the fast-evolving consumer landscape.
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Dave Lambert of Right Side Capital: A Data-Driven Approach to Pre-VC Investing
02/05/2025
Dave Lambert of Right Side Capital: A Data-Driven Approach to Pre-VC Investing
Dave Lambert, co-founder and managing director at Right Side Capital Management, has built one of the most active pre-VC investment firms in the U.S. With a portfolio of over 2,000 companies, Dave and his team take a data-driven approach to ultra-diversified early-stage investing, making quick decisions and challenging traditional VC norms. In this episode... In this episode, Dave shares how Right Side Capital identifies high-potential startups before they reach traditional VC rounds. He explains how his experience as both an entrepreneur and an investor led him to see inefficiencies in early-stage fundraising—and how data and systematic portfolio construction can optimize returns. Dave also discusses the evolution of venture capital, the impact of AI on startup scaling, and why ownership percentage is irrelevant when evaluating investment opportunities. His unique approach reveals how ultra-diversification and a power-law mindset can uncover the next billion-dollar companies. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha 00:48 Meet Dave Lambert: Entrepreneur and Investor 01:48 Challenges in Early Stage Investing 04:11 The Data-Driven Approach of Rightside Capital 06:42 Evolution of Investment Strategies 13:47 The Impact of AI on Startups 17:01 Fundraising and Portfolio Management 19:50 Sourcing and Evaluating Investments 31:18 Advice for Aspiring Investors 34:23 Conclusion and Final Thoughts
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Charles Hudson of Precursor Ventures: Navigating AI, Inclusion, and Early-Stage VC
01/29/2025
Charles Hudson of Precursor Ventures: Navigating AI, Inclusion, and Early-Stage VC
Charles Hudson, Managing Partner and Founder of Precursor Ventures, joins Steve Brotman to share his journey through venture capital. With over 15 years of experience, Charles has made more than 400 investments and raised over $200 million, making him a leading voice in the seed-stage community. Here’s a glimpse of what you’ll learn: 00:43 - Introduction to Driving Alpha Podcast 00:53 - Meet Charles Hudson: Venture Capitalist Extraordinaire 03:41 - Charles Hudson's Early Career and Entrepreneurial Journey 06:12 - The In-Q-Tel Experience 08:15 - Transition to Business School and IronPort Systems 09:50 - Founding Precursor Ventures 13:03 - Challenges and Strategies in Venture Capital 14:31 - Portfolio Construction and LP Resistance 19:52 - Reflections on Early Fundraising and Success Stories 22:34 - Investment Beginnings: From Ideas to Tangible Plans 24:40 - Evaluating Founders: The Checklist Approach 26:27 - Geographical Influence on Startups 27:55 - Diversity and Inclusion in Venture Capital 33:36 - Navigating the AI Investment Landscape 41:51 - The Role of Seed and Pre-Seed Funding 45:16 - Connecting with Precursor Ventures In this episode... In this episode, Charles dives into his journey from aspiring public equities manager to leading one of the most successful pre-seed venture capital firms. He shares invaluable insights into his career path, including his work at In-Q-Tel, founding Precursor Ventures, and his investment philosophy. Charles opens up about the challenges of building a venture firm, including navigating LP skepticism, constructing diverse portfolios, and maintaining a founder-first approach. Charles also shares his thoughts on the current state of AI, its potential, and the challenges of finding sustainable, defensible models. From portfolio construction to diversity and inclusion in venture capital, his strategies offer invaluable lessons for VCs and entrepreneurs alike.
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Texas Tech Boom: Joshua Baer of Capital Factory on Startup Ecosystems
01/15/2025
Texas Tech Boom: Joshua Baer of Capital Factory on Startup Ecosystems
How do you turn Texas into a global innovation hub? For Joshua Baer, founder and CEO of Capital Factory, the answer lies in empowering unstoppable founders, fostering a vibrant entrepreneurial community, and leveraging Texas’s unique advantages. Here’s a glimpse of what you’ll learn: 00:43 Introduction to the Driving Alpha Podcast 00:54 Meet Josh Baer: Texas Startup Powerhouse 01:37 The Impact of Capital Factory 03:44 Josh Baer's Entrepreneurial Journey 07:07 Early Ventures and Lessons Learned 11:06 The Birth of Capital Factory 13:58 Investment Strategies and Focus 17:22 The Future of Robotics and AI 18:02 AI's Impact on Humanoid Robotics 18:22 The Inflection Point of GPS in Smartphones 19:31 Capital Factory's Open-Door Policy 20:21 Texas: A Hub for Startups and VCs 21:12 The Path to Becoming a VC in Texas 26:46 Government and Dual-Use Technology 31:15 The Booming Tech Scene in Texas 34:34 Conclusion: Reflections and Future Prospects In this episode... On this episode of Driving Alpha, host Steve Brotman explores Joshua’s journey from launching a startup in his dorm room at Carnegie Mellon to building Capital Factory into the most active early-stage investor in Texas. With nearly 1,000 investments, the firm isn’t just funding startups—it’s creating an ecosystem. Capital Factory focuses on “dual-use” startups that serve both commercial and government markets, with Texas positioned as a leader in AI, robotics, and national security. Companies like Aptronic, a pioneer in humanoid robotics, showcase Texas’s growing role in transformative industries. “Texas is our nexus,” says Joshua. “It’s where we have a unique advantage—a center of gravity for innovation.” By combining talent-driven investing with a collaborative model that partners with VCs, Capital Factory is redefining what’s possible in venture capital.
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Chris Farmer of SignalFire: The Data-Driven VC Revolution
12/18/2024
Chris Farmer of SignalFire: The Data-Driven VC Revolution
Chris Farmer, the founder and CEO of SignalFire, is transforming the venture capital landscape through a pioneering, AI-native approach. Leading a $2.1 billion early-stage venture firm, Chris has integrated cutting-edge data analytics to revolutionize how investments are sourced and scaled. His journey began with operational and entrepreneurial roles, including spearheading the turnaround of Skybitz and building early investment sourcing technology at Bessemer Venture Partners. Later, at General Catalyst, Chris led seed investments in groundbreaking companies such as Coinbase, Discord, and Stripe. Now at SignalFire, his AI-driven platform, Beacon, analyzes over 650 million people in the tech ecosystem, empowering founders and redefining the future of venture capital. Here’s a glimpse of what you’ll learn: 00:00 Introduction to Chris Farmer 00:18 Chris Farmer's Early Career and Education 01:21 Journey Through Venture Capital 02:43 Founding SignalFire 04:13 Data-Driven Approach in Venture Capital 06:19 Challenges and Strategies in VC 08:59 Building and Supporting Startups 19:54 Market Dynamics and Valuations 25:07 AI-Driven Paradigm and Sector Selection 25:57 Technology Product Building and AI Applications 26:55 Healthcare and Vertical Specialization 27:44 Underdog Companies with Huge Potential 31:59 AI's Generational Opportunity and Labor Market Impact 39:35 Navigating Labor Displacement and Societal Impact 41:28 Valuation Models and Market Opportunities 44:29 Capital Return and Long-Term Investment Challenges 49:27 Regulatory Impediments and Government Efficiency 51:35 Conclusion and Final Thoughts In this episode... We dive deep into Chris’s journey, from his early career at General Catalyst to founding SignalFire. He shares the inspiration behind leveraging data in venture capital, the challenges of gaining LP buy-in, and how SignalFire was built to solve structural inefficiencies in the VC ecosystem. Learn about Beacon, SignalFire’s proprietary AI platform, and its game-changing impact on startup discovery, founder evaluation, and portfolio company growth. Chris also discusses why he believes AI represents one of humanity’s greatest opportunities, providing unprecedented efficiency gains and reshaping industries. He touches on how AI-native firms have a competitive edge, the role of data in early-stage investing, and SignalFire’s focus on vertical AI SaaS, health tech, and more.
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Securing the Future: Richard Seewald of Evolution Equity on AI and Cyber Investing
12/10/2024
Securing the Future: Richard Seewald of Evolution Equity on AI and Cyber Investing
Richard Seewald, founder and managing partner of Evolution Equity Partners, joins Driving Alpha to share his incredible journey from scaling AVG Technologies to $400 million in revenue to leading one of the world’s largest cybersecurity-focused VC funds. With over 30 years of experience and $2 billion raised to invest in category-defining software companies, Richard offers invaluable insights into the cybersecurity and venture capital landscapes. Here’s a glimpse of what you’ll learn: 00:00 Introduction to Driving Alpha 00:20 Guest Introduction: Richard Seewald 01:55 Richard's Journey in Tech and Cybersecurity 03:42 Investment Strategies in Cybersecurity 06:23 The Importance of People in Investments 07:47 Cybersecurity Landscape in Israel 09:52 Impact of AI on Cybersecurity 16:30 Future Trends in Cybersecurity 24:23 Personal Insights and Advice 28:07 Conclusion and Farewell In this episode... Richard discusses how AI-driven automation is transforming cybersecurity, with companies like Torque and Protect AI leading the charge. He also highlights the unmatched innovation coming out of Israel’s cybersecurity ecosystem and explains why his firm continues to double down on the region despite geopolitical challenges. The conversation delves into the traits that define great founders, the importance of high-conviction investments, and the future of the cybersecurity industry. Whether you’re an entrepreneur building the next big thing or an investor seeking your next opportunity, this episode is packed with actionable insights and inspiration.
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How Owl ventures is driving the future of EdTech: global insights with Amit Patel
12/03/2024
How Owl ventures is driving the future of EdTech: global insights with Amit Patel
Amit Patel and Brian Smiga discuss the origin story of Owl Ventures, founded in 2014 in response to major shifts in education technology infrastructure and consumer behavior. They cover key trends that enabled the rise of edtech, including the expansion of broadband in U.S. schools and the availability of affordable devices like Chromebooks. Amit shares his unique career journey, starting in film and theatre before pivoting to a career in venture capital. In this episode of Driving Alpha, host Brian Smiga interviews Amit Patel, Managing Director at Owl Ventures, the world's largest venture capital firm focused on education technology. Amit has been instrumental in shaping Owl Ventures' strategy and has led investments in top edtech companies like Codecademy, RaiseMe, and Amira Learning. With deep experience across operations, strategic partnerships, and firm building, Amit shares his insights on the growth and evolution of the edtech sector. Here’s a glimpse of what you’ll learn: 00:00 Introduction and Guest Welcome 00:16 Amit Patel's New York Journey 01:25 The Origin Story of Owl Ventures 02:47 Education Technology Evolution 06:33 Global Expansion and Investments 13:29 Focus on Outcomes and Efficacy 16:19 Key Ingredients for Successful Startups 22:21 AI in Education 27:01 Emotional Impact and Success Stories 28:30 Conclusion and Final Thoughts In this episode… Host Brian Smiga interviews Amit Patel, Managing Director at Owl Ventures, the world's largest venture capital firm focused on education technology. Amit has been instrumental in shaping Owl Ventures' strategy and has led investments in top edtech companies like Codecademy, RaiseMe, and Amira Learning. With deep experience across operations, strategic partnerships, and firm building, Amit shares his insights on the growth and evolution of the edtech sector. The conversation highlights Owl Ventures' global investment strategy and the firm's emphasis on building an international portfolio. Amit talks about how the need for high-quality education worldwide has driven their global expansion, with recent investments in Asia and Europe. He explains their approach to assessing startups, focusing on business fundamentals, team strength, and measurable learning outcomes. They delve into the role of AI in education, exploring how generative AI is transforming personalized learning experiences. Amit emphasizes the importance of leveraging AI to assist teachers, freeing them up for more impactful one-on-one interactions with students.
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From Thesis to Investment: Chip Hazard of Flybridge on Early-Stage AI Bets
11/19/2024
From Thesis to Investment: Chip Hazard of Flybridge on Early-Stage AI Bets
Chip Hazard is a General Partner at Flybridge Capital Partners, where he has been investing in early-stage technology companies since 2002. He co-founded Flybridge, focusing on ambitious founders building the AI-powered future. With a background in Greylock and a proven track record in venture capital, Chip has been a key investor in successful companies such as MongoDB. He also co-founded XFactor Ventures, a fund supporting female founders. Chip’s expertise spans enterprise infrastructure, financial technology, digital health, and AI. Here’s a glimpse of what you’ll learn: 00:00 Introduction to Steve Brotman and Alpha Partners 00:18 Meet Chip Hazard: Early Stage Technology Investor 01:44 Chip's Journey into Venture Capital 02:48 Founding Flybridge Capital Partners 03:59 Flybridge's Investment Strategy and AI Focus 05:21 Key Investments and AI Applications 08:23 The Future of AI and Market Opportunities 09:06 Traits of Successful Founders 19:33 Investment Decision-Making Process 27:48 Advice for Entrepreneurs and Board Members 29:30 X Factor Ventures and Supporting Female Founders 32:05 Conclusion and Fundraising for Flybridge In this episode... In this episode of the "Driving Alpha" podcast, host Steve Brotman dives into an engaging conversation with Chip Hazard. Chip shares his journey from joining Greylock straight out of Harvard Business School to founding Flybridge Capital Partners. The discussion covers Flybridge’s investment strategy, which is focused entirely on AI, and highlights their approach of backing founders at the pre-seed and seed stages. Chip offers deep insights into the evolving landscape of AI, likening the current surge in AI innovation to a "Netscape moment," signaling a monumental shift in technology. The conversation also explores key investments made by Flybridge, including notable AI application and infrastructure companies like Melody Arc, Prime Security, Church AI, and Mako. Chip provides a nuanced analysis of the importance of the human-AI interface and how successful AI startups need to rethink traditional SaaS models. The discussion wraps up with valuable advice for entrepreneurs, insights into Flybridge’s unique decision-making process, and an overview of XFactor Ventures, a fund aimed at supporting female-led startups.
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Dror Nahumi of Norwest: How to Build Unicorns in Venture Capital
11/12/2024
Dror Nahumi of Norwest: How to Build Unicorns in Venture Capital
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.
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Tim Draper of Draper Associates: Future Markets and Viral Innovation
11/05/2024
Tim Draper of Draper Associates: Future Markets and Viral Innovation
In this latest episode of Driving Alpha, venture capitalist Steve Brotman welcomes Tim Draper, founder of Draper Associates, DFJ, and Draper University. Known for his visionary investments in companies like SpaceX, Tesla, and Coinbase, Tim Draper has left an indelible mark on the venture capital landscape. Here’s a glimpse of what you’ll learn: 00:00 Introduction to the Episode 00:56 Tim Draper's Journey into Venture Capital 02:28 Building DFJ and Draper Associates 03:36 Tim's Mission to Spread Entrepreneurship 04:39 Advice for Aspiring VCs 06:18 The Importance of Diversification 08:12 Viral Marketing and Its Impact 10:53 AI in Venture Capital: The New Frontier 11:36 Advice for Aspiring Entrepreneurs 13:02 Reaching Out to Draper: Tips and Tricks 13:28 Future Market Perspectives: AI, Healthcare, and Space 15:09 The Rise of Bitcoin and Smart Contracts 16:58 Political Views and Optimism for the Future 18:15 Transforming Monopolies with Startups 19:37 Final Thoughts and Farewell In this episode... Tim's career began with a family legacy in venture capital, but he quickly made his own name with bold bets and groundbreaking contributions to viral marketing. With a legacy rooted in innovation and decentralization, Tim shares his unique insights into emerging technologies, market trends, and what it takes to support ventures that change the world. Tim discusses the vital role of diversification, the power of AI in venture capital, and his belief in the power of startups to challenge monopolistic structures. This episode is a must-listen for anyone interested in the future of finance, AI, and the power of viral growth.
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Raju Rishi (RRE Ventures): Navigating the Shifting Dynamics of Venture
10/29/2024
Raju Rishi (RRE Ventures): Navigating the Shifting Dynamics of Venture
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.
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Jeffrey Berman of Camber Creek: Outperforming in Real Estate Tech with Domain Expertise
10/22/2024
Jeffrey Berman of Camber Creek: Outperforming in Real Estate Tech with Domain Expertise
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.
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Leura Craig of Outlander VC: A Unique Journey from Design to Venture Capital
10/15/2024
Leura Craig of Outlander VC: A Unique Journey from Design to Venture Capital
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.
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Investing in Trust: Matthew Greenfield of Rethink Education on Relationship-Driven Venture
09/10/2024
Investing in Trust: Matthew Greenfield of Rethink Education on Relationship-Driven Venture
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.
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High Conviction, Low Velocity: Rebecca Kaden of Union Square Ventures on Strategic Investing
09/03/2024
High Conviction, Low Velocity: Rebecca Kaden of Union Square Ventures on Strategic Investing
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.
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Ed Sim of Boldstart Ventures: Inception Investing in Technical Enterprise Founders
08/21/2024
Ed Sim of Boldstart Ventures: Inception Investing in Technical Enterprise Founders
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. Episode Chapters: (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 In this episode… 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.
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Navigating VC Volatility: Hans Swildens (Industry Ventures) on Staying Ahead
07/26/2024
Navigating VC Volatility: Hans Swildens (Industry Ventures) on Staying Ahead
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. Episode Chapters: (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 this episode… 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.
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Pro Rata Strategy: Jason Calacanis of LAUNCH on Seed Stage Edge
04/29/2024
Pro Rata Strategy: Jason Calacanis of LAUNCH on Seed Stage Edge
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.
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Steve Brotman of Alpha Partners: Redefining Venture Capital and the Future of AI
04/29/2024
Steve Brotman of Alpha Partners: Redefining Venture Capital and the Future of AI
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.
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Driving Alpha: Exploring Early Tech Ventures and the Evolution of Financial Media with Ron Insana
04/29/2024
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.
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