Bootstrapping SaaS: 15 years of organic growth with Anthony Eden @DNSimple

saas.unbound is a podcast for and about founders who are working on scaling inspiring products that people love, brought to you by https://saas.group/, a serial acquirer of B2B SaaS companies.

In episode #14 of season 5 of the saas.unbound podcast, Anna Nadeina chats with Anthony Eden, the founder and CEO of DNSimple, a hosting and domain management automation solution. Anthony shares his fascinating journey from early days in domain registration to building a lean, profitable SaaS business over 15 years. This article dives into the story of DNSimple’s organic growth, the transition from consulting to product, team dynamics, and the company’s thoughtful approach to scaling and innovation.

Anthony’s Journey into Domain Management

Anthony’s path into domain management started in 1999, working as CTO for one of the first seven domain registrars after the deregulation of the .com domain monopoly. This early exposure to the commercialization of domain names planted the seed for what would later become DNSimple.

After a startup that didn’t take off in 2010, Anthony grew frustrated with the existing DNS management interfaces and decided to build his own DNS company. Within just three months, he launched DNSimple, initially focusing on DNS management through a command-line interface. Customer feedback soon encouraged him to add domain registration services, which accelerated growth.

Bootstrapping DNSimple: From Consulting to Product

Initially, DNSimple was developed under Anthony’s consulting company, Atreion LLC. The company slowly evolved from a consulting business to a product-focused SaaS company. The transition was marked by structural changes, including selling the LLC to a Delaware C-Corp in 2018 to enable future growth options, even though they never took outside funding.

Anthony started the company with just himself and his brother, who handled server operations. The first employee was acquired through a small adjacent company specializing in domain-related services. Over time, as the company stabilized and grew, Anthony hired more team members, reaching around 25 employees today. The growth has been steady and deliberate, averaging about 0.7 new hires per year, reflecting a conscious choice to prioritize profitability and sustainable expansion over rapid scaling.

Customer Support and Team Dynamics: Everyone is Involved

One of DNSimple’s unique approaches is that every team member, including engineers, participates in customer support. Initially, the whole team shared a support queue, picking up requests as they could. As the company grew, they hired dedicated support staff to triage and handle common non-technical issues, while technical questions are routed to engineers.

This hands-on approach keeps the team connected to customer pain points and feedback, directly influencing the product roadmap. Balancing new feature development with maintenance and bug fixes remains a constant effort.

Fun and Accessible Marketing

DNSimple is known for its approachable and fun marketing style, which stands out in a typically technical field. This creative flair comes largely from a team member who is both a designer and developer, responsible for the company’s popular web comics and playful website elements like an Easter egg music player that turns DNS records into tunes.

Anthony emphasizes that running a business should be enjoyable, and creating a little fun for customers helps make mundane tasks like DNS management more engaging.

Scaling and Team Growth: Knowing When to Step Back

As the company grew, Anthony experienced the classic founder’s challenge of knowing when to transition from hands-on technical work to strategic leadership. The turning point came when he no longer felt confident participating in the on-call rotation for production incidents. This shift allowed the CTO to focus on long-term technology strategy while Anthony concentrated on marketing, sales, and overall business operations.

Hiring at DNSimple focuses on finding people comfortable with a fully distributed, asynchronous remote work environment. Candidates must be proactive communicators who embrace the trade-off between work hours and salary, valuing flexibility and balance over high pay with burnout risk.

A Measured Approach to AI Integration

Despite the AI buzz, DNSimple has taken a cautious, thoughtful approach to generative AI. Team members experiment internally, but the company has not rushed to add AI features to its product or marketing. Anthony highlights the importance of having a safe usage policy and understanding AI’s potential pitfalls before integrating it into customer-facing solutions.

For 2025, one of DNSimple’s key objectives is to determine AI’s appropriate role in their business, balancing innovation with responsibility and customer value.

Setting Annual Objectives and Strategic Focus

DNSimple’s planning process has matured from ad-hoc development to a structured annual goal-setting exercise. Each year, Anthony drafts a document outlining big ideas and goals, which he reviews and refines with the executive team before sharing with the broader company at their team meetup.

For 2025, the three main objectives are:

• Growing the enterprise customer base while continuing to serve individual engineers and smaller customers
• Exploring the role of generative AI within DNSimple
• Reducing single points of vendor failure to ensure stability and longevity

These goals reflect a balance between sustaining core customers, innovating cautiously, and managing operational risks.

Long-Term Vision and Exit Strategy

Anthony envisions DNSimple as a generational business but remains open to an exit if certain financial and stakeholder satisfaction thresholds are met. His priority is ensuring customers remain happy and the distributed team is cared for, ideally transitioning to a company that values remote work as much as DNSimple does. He emphasizes that an exit should be driven by a pull toward something new rather than push factors.

Biggest Wins and Failures

Anthony’s biggest win was reaching the point where DNSimple could pay his salary and provide financial stability, fulfilling his vision of a sustainable business. The biggest failure was a personal one: the souring of his relationship with his brother, who was an early partner in the company. This difficult experience taught him valuable lessons about working with family and shaped how he approaches collaboration today.

Secret Hack: The Power of Conferences

To maintain motivation and keep the business growing, Anthony relies on attending and speaking at conferences. Being around other founders, engineers, and industry experts energizes him and provides fresh perspectives. This “gorilla marketing” approach of showing up in person and engaging with the community has been a key part of DNSimple’s long-term success.