Driving Alpha

Ben Orthlieb, co-founder of Blue Moon and former LinkedIn and Emergence star, is transforming venture capital with AI and behavioral science. He discusses how Blue Moon identifies top founders and predicts billion-dollar potential through innovative evaluation methods. With proprietary AI agents, they analyze thousands of startups yearly, focusing on true founder potential rather than traditional metrics. Ben outlines their unique two-meeting investment process and emphasizes the importance of small checks to foster entrepreneurial innovation.

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.  

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.  

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.  

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.

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.

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.  

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.

David Hornik, founding partner at Lobby Capital, brings over 25 years of venture capital experience to the table. He discusses his surprising transition from law to VC and the serendipity behind early successes, including Splunk’s massive acquisition. David emphasizes the art of networking through his Lobby Conference, cultivating meaningful connections. He reflects on his biggest wins and missed opportunities—like Facebook and Uber—while revealing how psychological insights and emotional intelligence play vital roles in assessing startup founders.

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.