Driving Alpha

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:

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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:

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 se...

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.

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 Introdu...

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...

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 - Introduc...

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
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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 ...

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 capi...

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 piv...

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 supp...

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 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:

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 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 doma...

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 unc...

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 Univer...

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 th...