meta_pixel
Tapesearch Logo
Log in
Masters of Scale

The case for bootstrapping, w/Mailchimp's Ben Chestnut

Masters of Scale

WaitWhat

Business, Jeff Berman, Startups, Reid Hoffman, Management, Diversity & Inclusion, Mindset, Bob Safian, Entrepreneurship

4.64.4K Ratings

🗓️ 21 May 2019

⏱️ 49 minutes

🧾️ Download transcript

Summary

You can bootstrap your business to scale, but you'll have to make your own luck. Nobody knows this better than Mailchimp's Ben Chestnut. He used a DIY ethos to grow a $600M company without ever raising a dollar of outside funding. The Mailchimp story is the exception to Reid's rule (always raise more money than you think you need!). The episode explores a range of options for those who don't fit the VC-funding mold. Cameo appearances: LeVar Burton (Star Trek, Reading Rainbow, LeVar Burton Reads), Don MacKinnon (Milq), Karen Cahn (iFundWomen).

Read a transcript of this interview at: https://mastersofscale.com/ben-chestnut-the-case-for-bootstrapping/

Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Transcript

Click on a timestamp to play from that location

0:00.0

Hi, it's Bob Safian. You've been hearing me as the host of rapid response in this feed for a few years now,

0:07.8

with short newsy interviews alongside the deeper dives of Masters of Scale. Well, I'm excited to share that rapid response is expanding into its own feed.

0:17.0

We'll be putting out shows twice a week, focusing on the urgent issues that business leaders are dealing with in real time.

0:24.8

So search for rapid response in your podcast player

0:28.0

and subscribe to make sure you get all our episodes.

0:31.2

I'll see you on the other side.

0:33.8

To be an artist has always required that you find a way to solve for the financial equation of the cost of producing your art.

0:49.0

In the old days, it was a sponsorship system, right? In medieval medieval times which was one of the greatest

0:55.2

explosions of art culture on the planet it was all about finding a rich patron to

1:02.0

support you, right?

1:05.0

That dynamic has always been present in the creation of art and the stories that are so important to the advancement of culture.

1:17.0

If you grew up in the 80s or 90s, you probably recognize that voice from Star Trek,

1:26.4

the next generation, or the kids show Reading Rainbow.

1:30.4

It's LaVar Burton.

1:32.0

Over the years, he's emerged as a steadfast champion. It's

1:33.0

a steadfast champion of literature and the arts.

1:36.0

He has a podcast now called

1:39.0

La Var Burton Reeds and a company called La Var Burton kids. He thinks a lot about the power of stories.

1:46.0

It is literature that ultimately connects us to our imaginations and our own

1:50.7

innate birthwriters storytellers.

1:53.0

Like artists and writers through the centuries,

1:57.0

Lavaar has grappled with that age-old question.

...

Please login to see the full transcript.

Disclaimer: The podcast and artwork embedded on this page are from WaitWhat, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of WaitWhat and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright © Tapesearch 2026.