Can a PhD in accounting build a top-tier VC firm in the heartland, and beat the coastal giants?

Ira Weiss did just that. As founding partner of Hyde Park Venture Partners and a professor at Chicago Booth, Ira has quietly helped turn the Midwest into a serious startup engine, backing breakout companies like ShipBob and Audit Site before they were household names.

Here’s a glimpse of what you’ll learn:

• 00:48 Introduction to Driving Alpha

• 01:00 Guest Introduction: Ira Weiss

• 01:14 Ira's Academic and Professional Journey

• 01:50 Hyde Park Venture Partners

• 03:07 Personal Connection and University of Chicago

• 05:00 Transition to Venture Capital

• 06:25 Routes to Becoming a Venture Capitalist

• 08:51 Evaluating Startups: Then and Now

• 12:23 Case Study: ShipBob

• 18:32 The Importance of Sticky Products

• 19:34 Exciting New Ventures: Audit Site

• 22:46 AI's Role in Auditing and Financial Systems

• 24:31 AI Adoption in Companies and Investment Strategies

• 28:45 AI's Impact on Academia and Student Learning

• 31:45 Investment Decision-Making Processes

• 38:06 Midwestern Entrepreneurship and Investment Insights

• 42:01 Reflections and Closing Remarks

In this episode,

Ira shares how his journey from academia to early-stage venture capital gave him a unique lens for spotting high-potential founders in overlooked markets. He dives into the importance of founder chemistry, sticky products, and the traits that separate real moats from hype. You'll hear how ShipBob scaled in a gritty, unsexy market and how Audit Site is transforming the world of financial audits using cutting-edge tech.

We also explore how AI is reshaping the startup world, from reducing headcount to disrupting traditional B2B models, and what that means for investors. Ira offers tactical advice for aspiring VCs, insights into how investment committees really work, and why the next breakout startup might not be in San Francisco or New York.