Driving Alpha

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, 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.

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, 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.

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

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, 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.