The Grass Isn't Always Greener on the Entrepreneurial Side

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Entrepreneurship is often glorified as the ultimate career goal, but what happens when running your own business loses its luster? Jason Gintert takes us behind the scenes of his journey from corporate life to co-founding WAN Dynamics, and then back to the corporate world as CTO of Laketec.
The entrepreneurial path wasn't always smooth. "The first two years were kind of rough," Jason reveals, describing how his income dropped to half of his previous corporate salary and required significant belt-tightening at home. Even as the business grew, unexpected challenges emerged – from the stress of having employees depend on you for their livelihood to the constant cash flow battles when large clients took 60-90 days to pay invoices.
Perhaps most surprising was Jason's realization that business ownership didn't provide the freedom he expected. "It's a misconception that when you have a business, you're your own boss," he explains. "You report to your employees, your customers, your stakeholders – everybody who depends on you." Despite successfully growing the company and navigating the explosive demand for remote access solutions during COVID, Jason found himself increasingly forced into sales roles he didn't want.
After selling WAN Dynamics and briefly working for the acquiring company, Jason took four months to decompress before joining Laketec. His transition back to corporate life brought welcome relief – consistent schedules, healthcare benefits, and the ability to focus
Connect with Jason:
https://www.linkedin.com/in/jasongintert/

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Chapters

1. The Grass Isn't Always Greener on the Entrepreneurial Side (00:00:00)

2. Welcome and Introductions (00:00:14)

3. Inside the US Network User Association (00:02:07)

4. The WAN Dynamics Origin Story (00:13:00)

5. Early Struggles of Business Ownership (00:16:35)

6. Growing Pains and SD-WAN Evolution (00:22:46)

7. From Business Owner to Corporate CTO (00:32:15)

8. Reflections and Final Thoughts (00:41:24)