The $12B Exit That Defied Venture Logic

What happens when patient execution is paired with strategic discipline?

After Mailchimp launched its Forever Free plan in 2009, the user base jumped from 85,000 to 450,000 in a single year – a 430% lift that lit the path to a $12 billion exit twelve years later.

How do you follow record-setting success? Get stronger. Take Pacaso. Their real estate co-ownership tech set records in Paris and London in 2024. No surprise. Coldwell Banker says 40% of wealthy Americans plan to buy abroad within a year. So adding 10+ new international destinations, including three in Italy, is big. They even reserved the Nasdaq ticker PCSO.

Invest for $2.90/Share

_{Paid advertisement for Pacaso’s Regulation A offering. Read the offering circular at invest.pacaso.com. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals.}

Here’s what you’ll learn: 

In 2008, small business budgets were collapsing. Email marketing companies tightened features and squeezed customers harder. Mailchimp co-founders Ben Chestnut and Dan Kurzius made the opposite bet: they'd remove their paywall entirely. 

The Forever Free tier let firms email up to 2,000 contacts at no cost. It seemed reckless when cash was king. Within twelve months, users ballooned 5-fold, paying customers rose 150%, and profits jumped 650%.

The gamble worked because not only did it build trust, it also solved an immediate problem when customer cash was scarce. But this wasn't desperation, it was necessity, and the foundation for a patient strategy that would pay off over a decade later.

As we look to grow Profit Snack, our goal is to create a valuable experience that extends beyond just the micro case studies you’ve grown accustomed to. As a BITES subscriber, you’ll get a front row seat as the brand evolves +

Refusing outside capital gave Mailchimp something most founders forfeit: control over their own timeline. While VC-backed competitors raced toward aggressive growth targets, burning through cash in the process, Chestnut and Kurzius could make decisions based on customer needs, not investor demands. Free users naturally graduated to paid plans as businesses grew, needing automation, more contacts, and advanced features.

No outside pressure meant they could execute thoughtfully, establishing sustainable unit economics before expanding into an All-In-One solution, successfully moving upmarket without losing their SMB focus. Deepening their engagement and retention with customers, while recruiting new cohorts with a simple, yet effective “Sent with Mailchimp” badge on every free message, helped drive them to 14 million users and over $700M in revenue by 2020, all while maintaining profitability.

By 2021, Mailchimp had built exactly what Intuit needed: a profitable, customer-obsessed platform serving millions of small businesses. Intuit wasn't just buying revenue; they were buying an ecosystem and customer base that not only aligned perfectly with QuickBooks and TurboTax, but also catalyzed their broader vision to move beyond just accounting tools and become the digital backbone for SMBs. A vision that resonated with Chestnut.

The acquisition wasn't luck; it was inevitable. Chestnut and Kurzius had maintained full ownership while building a business so strategically valuable that Intuit paid $12 billion, the largest deal ever for a bootstrapped company. Proving that bootstrapped founders can beat the odds and chart a path to cash out on their own terms.

150% – Twelve-month growth in paying customers after the Forever Free tier went live.

$800M – Estimated annual revenue at the time of sale. 

$12B – Purchase price Intuit paid for Mailchimp in 2021. The largest ever for a bootstrapped company.

70  billion – Total contact records Mailchimp managed across all customer audiences at the time of the Intuit acquisition.

$300M – The shared bonus pool for employees as part of the acquisition.

Our social sucks, and we know it. So we’re looking for an Engagement Manager to own that and develop our voice across platforms. There’s no JD. If you’re interested, just tell us why you’re good by reaching out to [email protected] with “Social Media” in the subject line.

Wethos is a platform built to help freelancers and small studios scope, price, and pitch their work with confidence. Now part of Spark & Code, Wethos is here to stay and ready to support the next wave of flexible, values-driven work. See Recommended Proposal Pricing.

Fund your growth, your way. With Senzu Capital Solutions, you can access up to $2M in non-dilutive capital, giving you flexible options to face challenges head on. You’re 5 minutes away from the financing you need to hit 100% of your growth goals. Get started for free.