Building a SaaS is often painted as a story of nonstop hustle, all-nighters, and “move fast and break things.”
But for Tom Buchok, founder of MailCharts and now Principal at Reach Frequency, the journey looked very different. He built and sold a successful, bootstrapped SaaS while also creating space for balance: a four-day work week, a team culture that valued sustainability, and a business model that wasn’t dependent on burning out.
In a recent conversation on SaaS That App: Building B2B Web Applications, Tom shared how he went from ad-tech producer to SaaS founder, scaled MailCharts through product-led growth, resisted the temptation of enterprise distractions, and eventually led his company through a successful acquisition by Validity.
Here’s how he did it and what SaaS founders can learn from his approach.
From Flash Banners to Founder
Like many SaaS founders, Tom didn’t follow a straight line into entrepreneurship. He began as a producer at an ad agency, where building Flash banner ads introduced him to programming. What started as tinkering with ActionScript grew into a deeper technical skillset.
As he moved into freelancing and ad-tech, Tom embraced Node.js early, which gave him the confidence to step into the role of technical founder. That technical foundation, combined with a marketer’s eye, gave him the perfect toolkit to launch MailCharts.
The “aha” moment came at the Recurse Center, where Tom and his co-founder Carl dreamed up a “Wayback Machine for email.” They started by capturing and storing brand emails, and what began as a fun experiment soon evolved into a product people would pay for.
From “Wouldn’t It Be Cool If…” to a Real Business
MailCharts wasn’t a Silicon Valley blitzscaling rocket ship; it was a series of milestones:
- Wouldn’t it be cool if this could pay our rent?
- Wouldn’t it be great if this could cover our salaries?
- Could this be a full-time business?
That “step ladder” mindset helped Tom and his co-founder avoid overwhelm and focus on steady, achievable growth. He notes that SaaS often feels like the “long slow ramp of death,” where $99 or $149 MRR doesn’t feel exciting at the moment. But over time, the compounding growth becomes undeniable.
Every two to three years, MailCharts leveled up. Looking back, Tom says those steps seem quick. But in the moment, they felt painfully slow. Patience and persistence are what allowed MailCharts to grow sustainably over a decade.
The Product-Led Growth Bet
MailCharts went all-in on product-led growth (PLG). Instead of building a sales-heavy organization, they focused on making the product so good that customers could discover, try, and buy on their own.
The model was simple:
- A freemium tier lets users experience real value.
- Paid tiers unlocked additional features, like data exports and advanced reports.
- The product itself was the salesperson, nudging users toward upgrades.
Why PLG? For Tom, it was partly philosophical and partly practical. PLG meant fewer support tickets, less handholding, and more time to focus on marketing. It also enabled something rare in SaaS: a four-day work week.
Saying No to Enterprise Distractions
At some point, every SaaS founder faces the lure of enterprise deals: big contracts, custom requests, and the promise of rapid revenue. For Tom, those deals became a distraction.
While MailCharts did close some enterprise accounts, Tom noticed a pattern:
- Larger deals created one-off requirements.
- They distracted the team from improving the core self-service product.
- They often came with headaches, like renegotiations during COVID.
So he made a bold choice: focus entirely on the self-service, credit-card-driven customer base. Enterprise clients were politely declined if they didn’t fit.
Building for Efficiency = Building for Acquisition
When founders think about exits, they often obsess over finding a buyer. Tom flips the script: build an efficient business first, and buyers will come.
At MailCharts, efficiency meant:
- Clean books and financial transparency.
- Clear standard operating procedures.
- A predictable, low-touch revenue model.
- A product loved by its core customer base.
When Validity came knocking, they weren’t strangers. They were already a MailCharts customer. Unlike the “tire kickers” Tom had encountered before, Validity’s team was professional, prepared, and serious. The due diligence process was smooth, and within a short time, the acquisition closed.
Tom admits he didn’t believe it would actually happen until the deal was done. However, because he genuinely loved running the business, his Plan B was simply to keep going. That mindset made the process less stressful and ensured that, whether or not a deal closed, MailCharts was already a great business.
Final Thoughts
After nearly a decade running MailCharts, Tom didn’t rush into a new startup idea. Instead, he leaned into coaching other founders, inspired by the impact his own coach had on him during the MailCharts years.
Today, through Reach Frequency, Tom helps B2B SaaS founders navigate leadership challenges, growth strategies, and the emotional rollercoaster of entrepreneurship. He brings the same philosophy that guided MailCharts: build sustainably, focus on balance, and define success on your own terms.
The lesson? You don’t need to burn out to build something meaningful. Sustainable success is possible. And sometimes, it even comes with a three-day weekend.
Tom’s Background
Tom Buchok is a SaaS entrepreneur, an expert in scaling businesses in the tech space, and the Principal at Reach Frequency, where he advises and coaches B2B SaaS founders on leadership and growth strategies. As the former CEO and Co-founder of MailCharts, he led the company through a decade of growth before its successful acquisition by Validity in 2022. With deep expertise in bootstrapped SaaS businesses and product-led growth strategies, Tom transformed MailCharts from a 'Wayback Machine for emails' concept into a revolutionary platform for e-commerce marketers optimizing email campaigns. Currently, Tom focuses on helping other SaaS entrepreneurs navigate their growth journeys while maintaining work-life balance and operational efficiency.
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