Is it the bootstrapper’s time to jump on the venture treadmill?

Hello and welcome back to Equity, a podcast about the business of startups, where we unpack the numbers and nuance behind the headlines.

This is our Wednesday show, where we niche down to a single topic, think about a question and unpack the rest. This week, Natasha and Alex asked: Is it the bootstrapper’s time to jump on the venture treadmill?

The episode was inspired by Natasha’s recent Startups Weekly column, “The bootstrapped are coming, the bootstrapped are coming” and the companion TechCrunch+ piece, “Will once-bootstrapped startups turn to venture during a watershed moment?” But, of course in classic Equity style, we continued the conversation with nuance and numbers as a focus.

Here’s what we got into:

• The definition of bootstrapping, and our own additions and subtractions.
• The trend of more bootstrapped companies taking on venture, or at least more venture capitalists being interested in bootstrapped companies.
• What the heck is a venture treadmill, and what to drugs have to do with it?
• We ended by both agreeing that we are, indeed, the best.

There’s ample history when it comes to bootstrapping companies eventually raising money. We just want to know if it is going to happen more often today, and earlier. Let’s chat!