How Ben Chestnut Bootstrapped Mailchimp to a $12 Billion Exit

Ben Chestnut, co-founder of Mailchimp joins Rob Walling on the stage at MicroConf US 2024 in Atlanta. They discuss Mailchimp's origin as a side project from a web consulting firm, its accidental yet pivotal adoption of the freemium model, and the company's growth to a $12 billion exit.
Ben shares insights on scaling the business, emphasizing the importance of operational excellence and fostering a creative culture. He also reflects on the challenges of serving small businesses versus enterprise clients and the decision not to develop a customer success team.
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[@El_Diablo_12]

Lol this dude is hilarious. This was the best kinda interview where you can learn something and be entertained at the same time 😄

[@El_Diablo_12]

15:00 we’re all winging it 27:15 Mailchimp hired famous hacker Kevin Mitnick to white hat them 28:00 Robb sold Drip with 10 people, a few million in revenue

[@AnthonySistilli]

Ben is a pleasure to listen to! Down to earth and humble. Would love to learn more from him haha.

[@EcomCarl]

Ben journey with MailChimp is a masterclass in bootstrapping and scaling wisely! His experience underscores the importance of evolving with customer needs and market demands, proving that sometimes the best path is carved by walking it. 🚀

[@AurelienAmackerRMIF]

The man, the legend, thank you for making it happen Rob!

[@tobebuilds]

28:36 That was my question 😀 amazing experience hearing straight from Ben

[@MicroConf]

Great to meet you in Atlanta Tobe!

[@sspykson]

This is so cool, pleasure to listen!

[@chenlim2165]

Legend. Keeping it real.

[@antoan.s]

Ben is awesome!

[@ps-dn7ce]

This is excellent

[@alexmacgregor]

Mailchimp story is wild. Great ep.

[@Greg_Chase]

"The people at the top - they're winging it too" If you have a farm that produces crops, you can hedge the pricing for when the harvest arrives later. Tech is not like that. Tech is like milk or cheese left outside in 80 degree sunny weather. You have to move *_FAST_* and planning is quite difficult. We're in the middle of an AI 'boom' and people still have very little clue where things are going. Farms, you can plan ahead. Tech, no freaking way. Move now or lose the chance. Over a long career, we've all seen Silicon Graphics, Sun Microsystems, Global Village, many others, pop above the surface then disappear. Borland, WordPerfect, Lotus123, Wordstar. Even Apple Computer nearly went out of business (Steve Jobs turned it around). Microsoft, Oracle, Intel are remaining tech giants who were around in the mid-late 1970s. .

[@BondJFK]

Nvidia & Microsoft will survive in another 25-50 years since the Azure cloud and investments in OpenAI, Not sure about other companies

[@thebrogrammer2077]

this is jason cohen tier

[@MicroConf]

We agree!

[@akibo8379]

I love your content. It’s made me jump into saas businesses. Now, I’m working on my first saas idea and would love help with my pitch deck. Can you guys help me with this?

[@VitaliyPodoba]

Hey, I know slidebean guys help with pitch decks for startups.

[@tobebuilds]

You don't need a pitch deck. Start validating by talking to potential customers and learning. Read "Start Small, Stay Small," and "The Mom Test"

[@Gigawattt]

The thumbnail I clicked on said “I’d tell my younger self this…” with a picture of the founder of MailChimp. Spoiler Alert: He has no idea what he’d tell himself 🤣

[@ryanchattertonYT]

Actually not bad and honest “advice” wtf do any of us know what we are doing?

[@BondJFK]

How a billion dollar exit works, I think exit will be difficult once you cross $100M ARR

[@archiee1337]

"You should consider freemium"

[@cairo0009]

He forgot to add the part where you promise you'll never sell your company as an excuse to give your employees 0% equity.

[@sidm9336]

He did not give his employees ESOPs. So what? There's a lot of companies that don't offer ESOPs. On the other hand, there's a plenty that offer them. What stopped these employees from moving?

[@El_Diablo_12]

He could’ve changed his mind. Employees got compensated fairly or else they would’ve found employment elsewhere.

[@tammiesspark]

Equity isn't candy. You never hand it out without a very special reason. Usually it's given for 2 special reasons. 1 -- the founder needs key managers to help grow the business and is unable to provide a fair compensation, so they hope to attract a manager who is fine with a long-term comp if the business is successful many years later. 2--the business needs to attract top tier talent who are paid an above market compensation already and are very limited, a business will offer stock options as a way to increase their offer. FAANG does this. Outside of these 2, giving stock to non-founders and investors is a poor business practice and foolish.

[@oopskapootz7276]

@@El_Diablo_12I know someone who worked there, their comp was massive.

[@mariojohnson4695]

He and the founders got all the equity, the employees got “Ganked”, that’s all I need to know. Bye!

[@BondJFK]

The employees may get a better salary than the rest of the companies

[@mariojohnson4695]

@@BondJFKTrue, a good salary is great equity creates wealth.