Austin Innovator - Jason Cohen
Austin Innovator - Jason Cohen
A journey of perseverance, intellectual curiosity, and the willingness to learn from both successes and failures
With the steady flow of ideas from the University of Texas at Austin and the influence of visionary leaders over the years, Austin has a long history of innovation. Jason Cohen’s story, shared with our audience during my Austin Innovators series at the Headliners Club last week, exemplifies this innovative spirit.
For several years now, I’ve assigned posts from Jason’s blog, A Smart Bear, one of the blogs I recommended in “In Search of Substance: The Case for Books and Blogs over News.” as readings in my business courses at the UT Austin McCombs School of Business. I’ve long admired Jason’s writing which focuses on starting and running successful businesses and was excited to engage with him in conversation. Jason did not disappoint.
Jason is both an accomplished entrepreneur and a thinker who combines pragmatism with intellectual curiosity. His journey started small but scaled significantly with code review tools company Smart Bear Software and later WP Engine, a leading WordPress hosting company. His experiences offer valuable insights for anyone interested in startups, technology, or business strategy.
The Value of Experience in Entrepreneurship
Jason’s entrepreneurial journey began with modest ventures that, while not financial successes, were rich in lessons. I stress to my students that entrepreneurship leads to two outcomes: success or experience—and Jason has experienced both. After a few small ventures, his startup, Smart Bear Software, became Jason’s first successful company. It was a code review tools company, and when Jason received an unsolicited offer to buy it at what he considered a fair price, he sold it. His wife had observed that Jason wasn’t enjoying himself at the company, so he seized the opportunity. The sale didn’t create generational wealth, but it provided a substantial return, setting the stage for his next success.
Jason shared an important takeaway for aspiring entrepreneurs: don’t be discouraged by failure, it’s often the precursor to success, and persistence is key. As he explained, “I can't find someone who's tried doing a company and failed and wishes they hadn't. They're always like, ‘Man, let’s rewind. I’ll keep that.’”
The idea for WP Engine, Jason’s next venture, came from his frustrations with hosting his own website. As a software developer, he understood the challenges of maintaining a website. To identify the right product offering, Jason conducted 50 interviews with potential customers, using an interesting approach. He offered to pay each person what they felt their time was worth for a one-hour interview. Not one interviewee accepted payment, but those conversations helped Jason shape the right combination of features and services for WP Engine.
Entrepreneurs often romanticize the notion of launching a "big idea." However, Jason’s experience shows that a good idea is just the start—execution, adaptability, and customer focus are key.
Intellectual Curiosity and Its Role in Business
One striking theme that emerged during our conversation was Jason’s intellectual curiosity. His formal education combined a computer science degree with art history—an unusual combination for a tech entrepreneur. Jason explained that his decision to study outside his professional field was driven by curiosity alone, which, for him, was a reward in itself.
This desire to learn for its own sake provides an important lesson: intellectual enrichment doesn’t always need a direct professional application. As Jason put it, “Life becomes richer when you have a wider range of experiences.”
Jason’s time in improvisational theater proved valuable in unexpected ways. He pursued improv for years before eventually leaving it to focus on family and business, but the skills he learned have stayed with him. Improv taught him how to listen, think on his feet, and collaborate with others—all of which are crucial in business. “Speaking and listening at the same time, working things out in the moment, trying to build something together... I do feel improv helps in many ways, including professionally.”
Bootstrapping vs. Fundraising: A Strategic Shift
One of the pivotal moments in Jason’s entrepreneurial journey was deciding when to bootstrap and when to raise capital. In the early stages of WP Engine, Jason bootstrapped, much like he had with his previous ventures. However, after WP Engine hit a certain level of success, he realized the company had the potential for much greater growth, and external funding became necessary.
He emphasized that raising money isn’t always the best strategy at the start, but once a business achieves product-market fit and sees an opportunity for exponential growth, funding can be a useful tool. “We hit product-market fit, and at that point, money can really solve things,” he said. His experience highlights the balance that entrepreneurs must strike between maintaining control and securing the resources needed to scale.
Building a Company Culture: A Lesson Learned
At WP Engine, Jason learned that company culture isn’t just a buzzword—it’s an essential component of long-term success. Early in his career, Jason admitted that he had been skeptical about the importance of culture, focusing more on tangible business metrics. However, his experience with WP Engine shifted his thinking, and he began to prioritize culture as a central part of the company’s identity and success.
He contrasted this approach with his earlier ventures, where he viewed culture as "wishy-washy nonsense." This hard-earned lesson showed him that a strong company culture can be a driving factor behind a company's success.
Do the right thing
Where the best get better
Aspiring to lead, committed to give back
Customer inspired
Built to last
The Art and Science of Pricing
Pricing is an area where many businesses struggle, and Jason’s approach offers practical insights. He emphasized that pricing is both an art and a science—while data can inform pricing decisions, human psychology and market positioning play significant roles. “It’s not extricable from the product,” he explained. If the price is too low or too high, it affects how customers perceive the product’s value.
Jason shared a compelling story about an IT customer who bought $490 worth of products monthly because he didn’t need approval for purchases under $500. This insight into customer behavior allowed Jason to adjust his pricing strategy to fit customer decision-making patterns. Pricing isn't just about numbers; it's about understanding customer decision-making processes. Customer interviews are often the best way to understand a customer's needs and buying process.
The Impact of AI on the Future of Software Development
When our conversation turned to the future, Jason discussed the transformative potential of AI, particularly in software development. He described the current generative AI tools as powerful but limited in scope. While developers are amazed by AI’s ability to assist in writing code, Jason made it clear that AI is far from replacing human developers entirely.
“There’s no limit to how valuable or good [UX design] can be,” Jason pointed out, suggesting that AI may not eliminate jobs but could help developers create better, more complex software. Most companies, he noted, are not completely satisfied with the software they currently use but feel constrained by budget to make improvements. Rather than reducing headcount, businesses will likely use AI to boost both the quality and quantity of their output.
Conclusion: Embracing Both Success and Experience
Jason Cohen’s journey is one of perseverance, intellectual curiosity, and the willingness to learn from both successes and failures. His experiences underscore the importance of customer research, thoughtful pricing strategies, and the realization that building a business is about much more than financial outcomes—it’s about creating lasting value for customers and for oneself.
