What I learn from Ben Chestnut, Co-founder of MailChimp

2:55 AM Saturday, August 14, 2021 adrian oh 0 Comments

Have you ever researched for tools so you can email blast (ok, spam) your customers? You probably heard of MailChimp. The company with a cute monkey logo wearing a postman hat. It is regarded as one of the most successful bootstrapped, SMB-focused SAAS (Software As A Service) company in the US, and probably the world. 

Need proof? Well, got spare cash? The founders might sell some shares at a $10 Billion USD valuation.

Ben Chesnut, co-founder of Mailchimp. He is one of the legendary SAAS founder whom i admired alot, for his unorthodox, witty way of doing things.

I did an interview with Simon Grabowski, CEO of Getresponse, one of mailchimp competitor a few years back. Hopefully one day, I have a chance to interview Ben, probably at Thailand (since he's half Thai). :)

These are some of the learning I picked up from this video interview he did with Jason Lemkin, founder of Saastr. There is another great video he did with Jazon Nazar too for article in entrepreneurs.com 



1) The 10X feature? Freemium, debuted in 2009~2010. This is where things really skyrocket. It grows like from 100,000 users, to about 1 Million within its first year, then to 3 Million on 2nd years. As you can see, this is not really a feature, but rather an innovation in the business model. (~4:33)

2) 1st Choke (point where one user converts from free to paid)? There isn't really any one choke. Since their targeted market is SMB, 30% of SMB die in 2 years, 50% die in 5 years. So he look at his sales pipeline like 5 to 10 years.  (~7:30)

3) How does Ben view churn? He asked, which industry in which the small business customers are the most tech savvy? That turned out to be the eCommerce customers, they are the one pushing the limit of innovation for mailchimp. The thinking is, how mailchimp can help them to sell more? Then the technology built for these group of high impact, high end customers, it will trickle down on the platform and benefits other customers as well. (~10:10)



4) Small business, frequently using mailchimp as CRM. Probably in a very similar way, Zetpy can copy a page from this too :), which we did. Zetpy can show you who are your Top 100 Spending Customers buying across channels like Lazada, Shopee, Shopify or WooCommerce. (~11:10) 

5) How does mailchimp build brands? Ben experiment with different type of medias (eg podcast). They have a culture of tinkering and experimenting with things. Ben wants something more tangible, where people can see, feel, coz it makes your brands real. Think Billboards, Monkey Toys, Socks! Summarizing Brand building in ABC (~14:20)

A) Care about your brand.
B) Try to get it physical, not just digital only (when you can afford it)
C) Always be tinkering.


6) #DoomFear - We (The biz) could die tomorrow, or becoming slow, then embarrassing descend into irrelevance, which is worse than crash. This probably apply to all of us, where things are moving at breakneck speed nowadays.  (~20:10)

7) What is it that mailchimp brands means to you? Customer said "it's marketing", it made Ben realize it's no longer just about email. this is where they expand beyond email. We should be asking this questions to our customers every quarter! (22:10)

8) Doom is always around the corner, eg GDPR (A real existential threat for any marketing company), and it probably never ends. They could have reacted negatively, but they always think from a customer viewpoint. So MailChimp redo the infrastructure just to cope and help their customers comply with it. Along the process, it builds up (even higher) trust with customers. (~31:00)

9) Any moat at mailchimp? Ben thinks he just wanna keep running faster as speed is his only moat, stay ahead of the curve, listening hard to your customers (Ben's mantra is Listen Hard, Change Fast), and keep adapting crisis after crisis. (~33:00)





10) The 3Cs. Entrepreneur, you are probably pretty good at one way of communicating, for Ben, it's blogging, that's how he marketed mailchimp. So again, the 3Cs, What's your Communication style? What's your Channels that is going to give you the highest Cadence? Stick to what works for you, and tell the stories about your brands!  (6:40)

11) How do you stay focused on the most important things? You really need to the know the goal, what is the end state that you want? Ben doesn't just stop there, he always goes one step further by asking "What are the habits I need, to achieve these goals? What are the habits I need to change? In order to get there?" Then he focus on acquiring new habits, change existing habits or both. Sometimes, he even forgot those goals,  as he get so focused on the habit change, that the goals come. 

So dream, look into the futures, what are the goals to move your company to the next level? What are the behaviours or habit that is going to get you there? Start focused on habit and behavior change!  (31:46)






adrian oh

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