Distress, Discipline and Gasoline - Season 5: Episode # 97

Not every great company is a venture company. And not every great venture investment looks like the kind of deal everyone else is chasing.

Brad Kotansky, Venture Partner at Copper Sky Capital, has built an investing philosophy around looking where the market isn't. With venture dollars increasingly concentrated among a handful of companies and fewer startups making it from Series A to Series B, Brad sees opportunity in places that don't always fit the traditional VC mold. That includes recapitalizations, distressed businesses, overlooked industries, and companies with broken capital structures that can be reset for their next stage of growth.

That perspective requires a different definition of a good investment. A company doesn't need to become a thousand-times return to create an exceptional outcome, and raising more capital isn't always the answer. Brad shares why investors need to understand the business beneath the valuation, why founders should resist the pressure to "incinerate money," and why the best time to pour gasoline on a company is only after you've found the fire.

Chapters

00:00 Introduction and Guest Introduction

00:24 Market shifts and venture focus

02:11 Justin Gray's background and office tour

04:02 Justin Gray's discussion on venture themes

05:26 Introduction of Brad and his background

07:20 Why B2B SaaS dominates venture capital

08:08 Emerging sectors and opportunities in venture

11:14 Venture investment criteria and valuation insights