Episode Summary
In this episode of An Agency Story, the featured guest is Jon Simpson, founder of Criterion B, a branding and content marketing agency focused on the multifamily real estate space. Jon’s journey is far from linear. Originally rooted in web development, Jon evolved from freelancer to agency leader, ultimately transforming Criterion B through several bold, and sometimes painful, pivots.
Episode Highlights:
- Leaving the Safety Net: Why Jon quit his job without a single client lined up and how serendipity filled his pipeline within weeks.
- Scaling Back to Grow: The emotional toll of laying off half his team to survive and how that moment became a turning point.
- Finding a Niche: What drove the decision to double down on the multifamily housing industry and finally build recurring revenue.
- Rebranding Under Pressure: How a cease and desist turned into an opportunity to redefine the agency’s identity.
- Entrepreneurship Reimagined: Jon’s transition from agency work to launching Swifty, a SaaS product built to solve the exact problems his clients were facing.
Agency Info
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Company: Criterion B
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Guest: Jon Simpson
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Year Started: 2008
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Employees: 1-10
If you start a business, you’re not going to get to do what you went to school for…unless it was business.
Jon Simpson
Key Takeaways
Bold Pivots Can Be Survival, Not Just Strategy
When web development became a source of burnout despite being the agency’s most profitable service, Jon chose to walk away. The transition to content marketing wasn’t just a creative choice, it was a strategic lifeline. Knowing when to quit a “successful” track can be the difference between stagnation and evolution.
Retainers Over Projects: A Game-Changer
Jon’s early years were marked by the project-to-project grind, often subcontracting for larger agencies. It wasn’t until Criterion B shifted to a retainer model that financial stability, and business clarity, emerged. If your agency’s revenue resets every January, it’s time to rethink your model.
Crisis Creates Clarity
Facing three weeks of runway and a depleted line of credit, Jon made the excruciating decision to lay off 13 people. That moment forced a hard reset, and it worked. Sometimes, trimming down to essentials is what sets the stage for future growth.
Identity Is More Than a Name
When forced to rename the agency due to a trademark dispute, Jon didn’t just pick a new name, he engineered a new brand narrative. Criterion B wasn’t just a workaround; it was a philosophical reframe. A forced change can become a powerful moment of reinvention if you control the narrative.
Built to Sell Doesn’t Mean Built to Leave
Jon’s embrace of John Warrillow’s Built to Sell model didn’t signal an imminent exit, but it did force a shift in how he structured his business. By making your company less dependent on you, you make it healthier, for you and your team.
Show Notes
Mentioned in this Episode:
- Built to Sell by John Warrillow – A catalyst for Jon’s decision to systematize his business.
- Swifty – Jon’s software solution built for the multifamily industry.
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