In 2001, three web designers built a quirky email tool called Mailchimp.It wasn’t their main business.It wasn’t even meant to make real money.For years, Ben Chestnut and his partners survived on web-design gigs, while Mailchimp earned just enough to cover lunch.Then…one surprising spreadsheet changed everything.In this episode, Ben reveals:The decision that ... Show More
Aug 3
Serena & Lily: Serena Dugan and Lily Kanter. They Built a $20M Brand—Then One Investor Almost Destroyed It
Many founders think the hardest thing about business is finding customers.It's not.It's surviving success.When Lily Kanter and Serena Dugan launched a luxury baby linen business, they had no manufacturing experience, no inventory, and barely any capital. But after their first cat ... Show More
1h 15m
Nov 2021
The case for bootstrapping, w/Mailchimp's Ben Chestnut
This week, we’re returning to an episode of Masters of Scale featuring Ben Chestnut, the co-founder and CEO of Mailchimp. The email marketing platform was acquired this year by Intuit in a multi-billion-dollar deal that closed this month. Hear how Chestnut used a DIY ethos to gro ... Show More
44m 56s
Dec 2022
20VC: Mailchimp's Ben Chestnut on The Biggest Leadership Lessons Scaling to a $12Bn Acquisition and $1BN+ ARR, The Secret to Happiness, Being a Great Husband and Father & Why 2021 was the Right Time To Sell to Intuit
<p><!-- wp:paragraph --></p> <p>Ben Chestnut is the Co-Founder of <a href= "https://mailchimp.com/">Mailchimp</a>, the all-in-one marketing platform for small businesses. Last year, in Sept 2021 it was announced that Intuit would acquire Mailchimp for a reported $12BN. There are ... Show More
50m 42s
Oct 2025
How to sell a billion dollars of snacks, with the founders of Chomps
Chomps co-founders Rashid Ali and Pete Maldonado had an unusual side hustle: selling meat sticks online. The co-founders join host Jeff Berman to reveal the phone call from Trader Joe’s that changed everything, how they used lessons from failed startups, and how they built Chomps ... Show More
32m 10s
Jan 2021
The Art of the eCommerce Side-Hustle with Ben Jacobs
Ben Jacobs worked at successful tech start-ups: Jet.com, Bird Scooters, and Salted. He has run a successful eCommerce drinking game side-hustle biz. He left his full-time job to build new retail/eComm venture. Top 3 Value Bombs: 1. Get out there and do it. 2. It takes years, a lo ... Show More
27m 27s
Oct 2025
How to Bootstrap to $1Million ARR [REVEALED]
In this episode of Startup Strategies, Juliana sits down with Ish Jindal, the engineer-turned-entrepreneur who spent four years not knowing what MRR meant while bootstrapping TARS to $1M ARR. After discovering the internet in his second year of college, Ish went from building edu ... Show More
1h 2m