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BenChestnut

INSIGHT

Bootstrapped Stories

In the earlier years, our firm focused primarily on supporting venture-backed businesses endeavoring to raise subsequent financing rounds. While this boded well in 2021 and 2022, as the market turned our team identified the need to pivot to capital-efficient and profitable companies. We pivoted our efforts to identifying bootstrapped companies: ones with little or no outside capital raised. These businesses were far more likely to be profitable and usually had very strong unit economics. The real challenge was finding them at the inflection point where they were looking to take on capital. The math for these founders is usually simple: will the cash and guidance provided by investors propel the business enough to offset the dilution incurred. For example, owning 60% of a $40 million ARR SaaS business is usually a better outcome than owning 100% of a $15 million ARR SaaS business. That said, it doesn’t always make sense, and our team has seen countless stories of raises and partnerships that don’t bring the level of accretion initially postulated. Furthermore, there are an array of companies that have reached impressive scale without raising outside capital. Below we chronicle three of them.

MailChimp

One of the greatest bootstrap stories is MailChimp's evolution into a leading email marketing platform. From its inception as a side project started by Ben Chestnut and Dan Kurzius in 2001, the company quickly carved out a niche by providing an email marketing solution for small businesses, reaching $1 million in ARR. This early phase was marked by a bootstrapped model, leveraging profits from the founders' web design agency and building around a freemium model to attract a wide user base. This approach helped establish a solid foundation, with the freemium model encouraging both initial use and gradual customer upgrades.
 
As MailChimp grew from $1 million to $10 million in ARR, it continued to reinvest earnings into product development and customer engagement. The company expanded its features based on customer feedback and invested in content marketing, building a loyal customer base. This period of growth was characterized by the freemium model's success and impact, driving user acquisition and retention through valuable, no-cost services alongside premium upgrades.
 
Navigating from $10 million to $100 million in ARR, MailChimp adopted a more aggressive growth strategy, including strategic acquisitions like TinyLetter in 2011, financed through its own revenue. This acquisition broadened MailChimp's appeal by adding a tool designed for simple, personal newsletters, complementing its existing services. Throughout this phase, MailChimp continued to innovate and diversify its offerings, demonstrating a scalable, user-centered approach to growth that maintained its original bootstrapped, self-funded ethos. Mailchimp never received external funding before being acquired by Intuit for $12 billion in cash and stock. Mailchimp has become an icon amongst bootstrap companies with many companies trying to replicate its success and proliferation. 

Craigslist

Craigslist’s inception and slow but steady rise in growth is from a very simple philosophy of “customer-focused” services, rather than focusing on immediate profits. Craigslist started initially as an email list in the San Francisco Bay Area back in 1995 as a simple email list. It was focused around software engineers in the area and postings generally were for social events for gatherings. As Craigslist grew, sections such as job postings allowed it to expand and it eventually became a webpage for online postings. Because Craigslist started as a pet project, there was little funds required to run the operation, as web pages were kept simple. This is a theme that still translates to present-day.

As the demand for Craigslist began to expand, the offerings expanded as well, with Craigslist charging a small fee for its job postings section. However, it was careful not to grow too much too quickly, as the team made sure that their first priority was the practicality and the usefulness of the site was maintained. By charging a small fee for these ad postings, however, Craigslist was able to hire its first employees and become a functioning company. Without competition and keeping their simplicity, Craigslist had little need to run ads on the website or update its technology while still growing due to the demand for a cheap method of ad postings. For the majority of users, Craigslist was still free, which allowed it to attract more and more users during this period of time.

By the time Craigslist reached $10 million+ ARR in 2004, it received attention from larger companies, specifically eBay, who purchased a 25% stake in the company after it was referred to by a former employee of Craigslist. However, this did not change their initial mission in having it remain as non-commercial as possible, as they kept to their original promise of not running banner ads on their website or having increased fees. The only difference, however, is that while keeping costs the same with the same basic features, Craigslist was able to expand from $10M ARR to over $100M ARR in just three years by the time 2007 came around. The combination of being the sole player filling a much needed hole and keeping to their non-commercial ideology since the beginning has allowed Craigslist to grow their user base organically and has encouraged them to remain loyal, a story rather difficult to replicate today with the focus on short-term gains.

Aha!

Aha!'s initial growth from $0 to $1 million in ARR in the absence of outside capital was due to a strong understanding of its target market and a commitment to solving real problems for product managers. The founders, leveraging their previous experience in product management and software development, identified a gap in the market for comprehensive, user-friendly product roadmap software. By focusing on customer feedback and adopting a lean startup methodology, Aha! developed a minimum viable product that directly addressed the needs of its target audience. Upon reaching the $1 million ARR milestone, Aha! focused on scaling its operations while maintaining capital efficiency. They achieved this by investing heavily in automation and streamlining internal processes, which allowed for rapid scaling without the need for proportional increases in staff or resources. This period of growth was characterized by a bootstrapped approach to financing, as well as reinvesting profits to fuel expansion. As Aha! crossed the $10 million ARR threshold, their team began looking for opportunities to accelerate growth through strategic acquisitions. Instead of raising outside capital, Aha! leveraged its strong cash flow and profitability to finance these acquisitions. Aha! also expanded its focus beyond product managers to serve a wider range of roles within organizations, including marketing and strategy teams, significantly enlarging its total addressable market.

A common trend across all three of these bootstrapped companies was their experienced founders, freemium business model, and scrappy management teams. 

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