Ben Chestnut on 20VC with Harry Stebbings

20VC: Mailchimp’s Ben Chestnut on The Biggest Leadership Lessons Scaling to a $12B Acquisition and $1BN+ ARR, The Secret to Happiness, Being a Great Husband and Father, & Why 2021 Was the Right Time to Sell to Intuit | 20VC with Harry Stebbings

Check out the Episode Page & Show Notes

Key Takeaways

  • Mailchimp was kind of an accidental business; it was originally built for just a few customers who were struggling to send out email newsletters 
  • The freemium pricing option teleported Mailchimp’s user base from tens of thousand to over a million users within a year of adding it
  • It is not always better to be faster 
  • It’s okay to be stressed and have chaotic feelings on the inside, but a calm demeanor is important to convey as a leader 
  • “The key to happiness is staying in your lane, and knowing when people need to be in their lane. Don’t get in their lane, and don’t let them get in your lane.”Ben Chestnut 
  • If you are a “hands-off” leader, ensure that you are also not an “eyes-off” leader
  • How you are perceived as a leader is often dependent on the setting in which you are leading
  • Founders tend to conflate their identity with that of their business; but with time, they realize that their life is not their business when they genuinely begin to reflect on their life
  • Ben is grateful for easing into new levels of wealth over the course of his life instead of having a one-time, shocking liquidity event
  • The happiest couples have husbands who keep their damn mouth shut   
  • “What I want the most is to not want.”Ben Chestnut 

Intro 

  • Ben Chestnut (@BenChestnut) is the co-founder of Mailchimp, an all-in-one marketing platform for small businesses that was recently sold for $12 billion. Ben is also a father, husband, design nerd, and cyclist. 
  • In this conversation, Ben Chestnut and Harry Stebbings discuss the origins of Mailchimp, lessons learned from Ben’s childhood, how to be a high performer in business, leadership styles, emotional intelligence, lessons learned from being a misfit, why Mailchimp didn’t take venture capital money, why he ultimately decided to sell after 20 years of running Mailchimp, how to stay humble through success, money, the secret to a happy marriage, advice for parents, and more  
  • Check out these Podcast Notes on How to Be Lucky As An Entrepreneur with Shaan Puri of My First Million 
  • Host – Harry Stebbings (@HarryStebbings

The Genesis of Mailchimp 

  • Ben was an entrepreneur from an early age, selling cartoon flip books he created himself, candies, and comic books on the school bus 
  • Mailchimp is the end of a series of pivots all the way back to grade school 
  • Mailchimp was kind of an accidental business; it was originally built for just a few customers who were struggling to send out email newsletters
    • Web design was the primary business at the time
  • The newsletter part of the business (Mailchimp) continued to organically grow for 3-4 years while Ben and his team continued building their web design agency 
  • A television segment of Robert Kiyosaki talking about passive revenue encouraged Ben to take a closer look at Mailchimp’s growth relative to the growth of his web design agency 
  • After separating Mailchimp’s and the web agency’s revenues, Ben saw just how fast Mailchimp was growing while the design agency flatlined, and decided to pivot the team’s full attention to Mailchimp
    • This was just after the 2000 Dot Com crash  

The Freemium Pricing Model 

  • Incorporating a freemium pricing model into Mailchimp resulted in exponential growth
  • The freemium pricing option teleported Mailchimp’s user base from tens of thousand to over a million users within a year of adding it
  • The user base continued to double in size with each passing year 

How Ben’s Mother Impacted His Life

  • Ben’s late mother was from Thailand; to her, business was just something that you do to make some extra money 
  • Ben’s father was from the United States and thought about business more in terms of what you might hear in a VC pitch 
  • Ben observed his mother’s small business remain a small business; she did not have aspirations to scale it to the rest of the world 
  • This observation is why Ben never externally calls his clients’ businesses “small businesses”, and instead refers to them as “businesses” 

Lessons Learned From Ben’s Father

  • Ben’s father would always take the scenic route when they drove to go fishing 
  • Then when they arrived at the lake, they always took another 1-2 mile hike to get to their fishing hole
  • Ben would complain about the hole hike, but his father never reacted to the complaints; he was stoic 
  • It is not always better to be faster 
  • These experiences with his father taught Ben: “Stuff is going to be hard. It’s not worth complaining.”
  • You do not have to be harsh as a leader
  • Ben’s father normalized being in a state of stress: “If you’re not stressed, you’re insane.” 
  • It’s okay to be stressed and have chaotic feelings on the inside, but a calm demeanor is important to convey as a leader 

High Performance In Business and Leadership 

  • You can increase your performance by removing current habits as much as (or more) than by adding new habits
  • “The key to happiness is staying in your lane, and knowing when people need to be in their lane. Don’t get in their lane, and don’t let them get in your lane.”Ben Chestnut 

Ben’s Style Of Leadership 

  • Creativity was everything to Ben in the early days of Mailchimp 
  • Ben brought in the most creative people he could find and stayed out of their way 
  • A company turns into a city once it grows beyond 500-1000 employees
  • The founder or CEO turns into a mayor that must lead the city, which presents a whole new set of challenges 
  • If you are a “hands-off” leader, ensure that you are also not an “eyes-off” leader
  • Becoming a hands-off, eyes-on leader was the biggest leadership change in Ben Chestnut’s life
  • This leadership change forced Ben to become more specific in his rhetoric to the company, such as clearly defining goals, KPIs, etc. 
  • Be self-aware of the areas in that you need to rely on others more, and also the areas in which you are the relative expert 

Advice To Founders

  • Being a founder can be lonely
  • Oftentimes, founders just want someone to listen to their problems and tell them that they are not alone 

Emotional Intelligence 

  • Growing up, Ben was always the leader of the misfits in whatever setting he was in 
  • Sometimes, he thinks of Mailchimp as an island of misfit toys 
  • How you are perceived as a leader is often dependent on the setting in which you are leading
    • In a small meeting with your co-founders, you may be a high-EQ leader
    • In a company  all-hands, you may come off as cold 

Lessons From Being A Misfit 

  • He was a misfit in school 
  • Ben came from a loving home but was “always ready for a fight” when he left the home
  • Being a misfit made Ben want to prove that he was a valuable person 
  • To this day, Ben has instinctive reactions when he feels that someone is pushing him too hard in a single direction 

Do You Wish You Took Venture Capital Money?

  • Founders tend to conflate their identity with that of their business 
  • The notion of selling their business is an absolutely absurd concept 
  • However, with time, founders grow, mature, and change, and may view themselves and their business through a more balanced perspective 
  • Most people begin to change in their mid-40s as some of their close friends and family members start to die 
  • People eventually realize that their life is not their business when they genuinely start to reflect on their life 

On Selling Mailchimp

  • Your entire existence as a CEO is composed of nothing but a set of habits 
  • These habits drive your thoughts, emotions, and actions 
  • When transitioning out of the CEO role, your habits dramatically change, and often rapidly change
    • This can be a brutal transition for many founders
  • Teleporting from poor to rich can significantly impact your brain
  • Ben and his co-founders experienced gradual growth over their time running the company, which resulted in a smoother transition to a life of monetary abundance 

Retaining Humility Through Success 

  • Ben desperately wanted his company to receive media attention in the early days of the company
  • But as the company became successful, the only validation he needed was a paying customer 
  • Ben prioritized humility in Mailchimp’s culture, so he was thrilled when an employee drew a mustache on his face when he was on the cover of a big magazine 

Why Ben Chestnut Sold Mailchimp When He Did 

  • Ben sold Mailchimp to Intuit in September 2021 for $12 billion 
  • He never felt the desire to sell Mailchimp, but he thought it was his duty to listen to people when they wanted to buy 
  • Ben was days away from making the decision to never be acquired or take outside money, and then Intuit called and the team understood small businesses 
  • The due diligence and test-the-waters process with Intuit took an entire year 
  • The Intuit deal was “too compelling” to say no 

Ben’s Relationship With Money 

  • Mailchimp was on the cusp of $1B in annual recurring revenue (ARR) when the acquisition happened, so the deal didn’t fundamentally change Ben’s money profile overnight  
  • Ben is grateful for easing into new levels of wealth over the course of his career 

How Do You Raise Your Children?

  • Ben’s children didn’t know how successful Mailchimp really was until one of their classmates brought a magazine into school with Ben’s face on the cover 
  • Your children won’t remember everything you say to them, but they will remember what you do 

Favorite Books Right Now

Weight Loss Tips 

  • Ben did a lot of cycling and walking to lose weight 
  • Walking is way more effective than people think it is 
  • Get rid of all soda and sugar water 
  • Decrease sugar consumption in general 

Why Ben Buys Lottery Tickets 

  • Ben buys lottery tickets as an inside joke between him and his wife 
  • When they were younger, his wife thought she won the lottery but she misunderstood how the numbering system worked for the tickets 

The Secret To A Happy Marriage 

  • The happiest couples have husbands who keep their damn mouth shut 
  • Listen harder to your significant other 
  • You don’t have to “win” arguments or discussions with your significant other 

Ben’s Guidance For Raising Children 

  • Ben has a parenting acronym known as “BLISS” in his head at all times while raising his children:
    • Balance
    • Love
    • Independence 
    • Self-Sufficiency 
  • Life is about slowing, incrementally improving yourself, and overcoming challenges 

Ben’s Next Five Years 

  • Instead of exploring exciting parts of the world as some founders do after selling their company, Ben wants to explore his own mind and understand why he thinks the way he does
  • “What I want the most is to not want.”Ben Chestnut 
    • This means being content with what you have 
  • There’s always going to be someone with a bigger yacht
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Notes By Stan Rizzo

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