Cloud Returns | A SaaS Investing Podcast

The episode is genuinely packed with frameworks (six vertical AI buckets, compete-vs-enable, business-in-a-box plus revenue share, custom automation platforms) and non-obvious claims about where margins and labor budgets shift, though some ideas are acknowledged as circulating VC takes.

“how are you using AI to solve a real-world business problem for a set of users in a way that maybe it doesn't look like a traditional software contract”

“if that's true, it means competing directly will work because you'll be able to have a much bigger end market”

The compete-vs-enable thesis and the argument that services businesses now look better than compressed-margin SaaS are framed with first-principles reasoning, but the guest himself concedes parts are well-trodden VC content.

“I'd rather almost bet on competing directly. 'Cause in either both work or neither works, but there's a lot more positive end cases competing directly”

“you've seen a million VC blog posts on this, you know, software spend will capture labor budget”

An active early-stage investor who leads pre-seed rounds and has concrete deals, making him a real practitioner, though he is a principal at a small fund rather than a senior operator who has built at scale.

“I'm a principal at Bowery Capital. Early stage B2B-focused fund, primarily investing at pre-seed”

“We led a pre-seed round into a company called Enata”

Dense with named companies and concrete numbers - Crosby, Abridge, Moxie, Alpaca Health, Distill, Percepta, BrainCo, Quanta, Harvey, Coverage - plus specific ACV figures, revenue thresholds, and a graduation drop-off statistic.

“Sequoia has backed this company Crosby that announced a significant financing”

“there's a company called Quanta. I think they just raised $15 million”

The host pushes with a genuine devil's-advocate scenario on the compete thesis and asks how it fits VC return horizons, but several prompts are broad catch-alls and the host's own long interjections sometimes substitute for sharper probing.

“And then a bit of a devil's advocate on this compete thesis is you have these— let's use accounting”

“And how well does compete fit within a venture capital framework in terms of horizon capital intensity?”