Jon Brennan of Developer Squad
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Jon Brennan of Developer Squad
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In Episode 2 of Huckaleros, Mike Brennan sits down with his business partner, cousin, and longtime friend Jon Brennan, President of Developer Squad.
Having worked together for nearly 20 years, Mike and Jon share the story behind their entrepreneurial journey, from early ventures and hard-earned lessons to the successes that shaped their careers. Along the way, they revisit a few epic failures, the challenges of building businesses with family, and the experiences that ultimately informed how they approach entrepreneurship today.
This is an honest conversation about resilience, partnership, risk-taking, and what happens when you keep showing up long enough to learn from both your wins and your mistakes.
Whether you're building a business, thinking about starting one, or simply enjoy founder stories, this episode offers a candid look at the realities behind the entrepreneurial journey.