In this episode of REIA Radio, hosts Ted Kaasch and Owen Dashner sit down with longtime friend (and legendary Omaha character) Thomas Kelly Klein Jr. for a funny, honest look back at what it really took to build OmahaNightlife.com—and what that season of life turned into later.

Kelly breaks down how OmahaNightlife.com started with a simple goal—get into events for free—and somehow turned into a major platform that helped shape Omaha’s nightlife scene. They talk about the early hustle, building attention before social media was even a thing, and how the “photo tag” era basically had everyone hunting for their picture the next day like it was the original Instagram.

From there, the conversation drifts (in the best way) into the friendships behind the business—like the long-running Risk board game nights, cigars, drinks, and Sunday night football that kept their crew tight for years.

They also get into the real entrepreneur scars: how running a chaotic business teaches you more than any class ever will, and why learning to pivot fast is survival. Kelly shares how their web business leaned hard into Flash… and then the iPhone came along and basically deleted that plan overnight.

A big thread through the episode is how reputation and relationships compound. They talk about using the platform to support charity events, how that shifted public perception, and how those moves opened doors with people they never would’ve met otherwise.

By the end, it’s less of a “nightlife story” and more of a real conversation about friendship, growth, mentorship, and choosing a life that feels worth living—without pretending the messy parts didn’t happen.

OmahaNightlife.com was ahead of its time—and Thomas Kelly Klein Jr. was right in the middle of it.

In this episode of REIA Radio, Ted Kaasch and Owen Dashner unpack the wild (and hilarious) rise of OmahaNightlife.com, the marketing tricks that worked before social media existed, and the hard lessons that came from building something big with your friends.

If you want a real entrepreneur story—wins, screwups, pivots, and everything in between—this one delivers.

Listen now, and if you want to connect with Kelly after the episode, reach out to Ted or Owen, or find him on LinkedIn.

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