“Start deep and narrow.” - Casey Allen

In this episode of Tech Scenes Malibu, Jeff Martin sits down with Casey Allen, founder of Enterprise Rising, to talk about grit, failure, and building the Midwest startup ecosystem from the ground up.

Casey’s journey didn’t start with privilege. Raised by a single mom and determined to create opportunity, he became an entrepreneur out of necessity — launching his first company at 18. He went on to start four more profitable companies, but without major exits. His reflection? Early success without mentors left him stuck below the $1M revenue ceiling.

Now, he’s committed to changing that for the next generation of founders.

The conversation dives into the rise of Midwest SaaS, the launch of Enterprise Rising as a focused room for enterprise tech founders, and why community matters more than hype. They explore the impact of AI on entrepreneurship, the increasing importance of unit economics, and why founders must raise their bar for metrics and discipline in today’s funding environment.

Casey also shares candid lessons on failure, ego, and what it really takes to build something meaningful outside Silicon Valley — emphasizing that the future of innovation isn’t coastal, it’s distributed.

Chapters:

00:00 The Midwest Startup Landscape

02:09 Enterprise Rising Conference: A Celebration of SaaS

04:50 The Impact of AI on Entrepreneurship

09:05 Unit Economics and the New Funding Landscape

11:48 The Importance of Metrics in Startups

16:16 Embracing Failure in Entrepreneurship

19:46 The Journey of a Founder

27:02 Creating Community for Entrepreneurs

32:29 The Art of Hosting Meaningful Events

Watch now to hear why the Midwest startup ecosystem may be one of the most underrated forces in tech — and what founders must master to thrive in today’s environment.

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