Super Angel/VC SMACKDOWN: What's so Great about Convertible Debt? (TCTV)

We’ve come to the last installment of the Super Angel v. VC SMACKDOWN and we’ve saved the wonkiest, nerdiest topic for last: Should entrepreneurs swap investor cash for convertible debt or equity?

Somehow, this is the topic that generates the most passion. If you don’t understand the basics, August Capital’s David Hornik– a former lawyer– breaks them down: “It’s about price and control.” Angels are saying that convertible debt deals are more entrepreneur friendly, but Hornik says there’s an easier way to make sure you don’t get screwed: “Don’t take money from people you don’t trust and like.” And then, Super Angel Dave McClure invokes Allah….yeah it doesn’t make a lot of sense in the video either.

The best moment of the entire series had to be in the 8 minute range when Hornik tells McClure to “shut up so he can agree with him.” Feel the love, people.

Beyond the nitty-gritty issues discussed this week, it’s fascinating to step back and look at what’s going on here from a cultural point of view. Venture capital has long been a private clubby world where people have grudges, but they’re kept “within the family” because everyone needs each other to do business. In a world where one homerun can make or break your career and your firm, no one wants to call anyone out.

That has utterly changed over the course of the summer, and it’s not because everyone just cares so much about convertible debt or any other issue the Davids argued about this week. It’s because this industry has under-performed for ten years and is on the verge of something seismic– whether it’s a shake-out or a reinvention or both. As a journalist who has covered this space for more than ten years, it’s going to be a fascinating year to watch and for great entrepreneurs, it’s a great time to make hay while these two groups continue to spar.

Reminder, there’s a live show of the debate at Orrick tonight, but I think it sold out on Tuesday. Our earlier segments were on “Why the Hate?” “Are Super Angels Just a Fad?” “Are Angels Just about the Flip?” and “Is Silicon Valley Getting Disrupted as the Center of Early Stage Funding?”

[NOTE: Was sick of sweaty wrestlers so I opted for a cuter smackdown photo today.]