45. From One Failed Restaurant to Over a Dozen Businesses & Millions in Real Estate
21 May 2026

45. From One Failed Restaurant to Over a Dozen Businesses & Millions in Real Estate

AJ Osborne Podcast

About

You’ve just started a business. Now what? If you’re Tanner Herget, you build another…and another…and another.


It’s hard enough to grow one business from scratch, but Tanner is the textbook definition of a serial entrepreneur. It’s all he’s known since 22 years old, when he left his full-time job to open his own restaurant.


That business failed.


Most inexperienced entrepreneurs would’ve walked away. For Tanner, giving up wasn’t an option. He quickly pivoted, transforming his struggling restaurant into a popular nightclub. It kept the lights on, but it also gave him the confidence to tackle his next venture.


Over the next 20 years, Tanner started more than a dozen businesses, many of which he still owns and operates today—from cash-flowing, brick-and-mortar establishments to long-term equity plays.


Today, we discuss what makes a business “work,” the hidden risks of partnerships, and the three-pronged approach to building wealth through entrepreneurship. Whether you’re launching your first startup or actively scaling, Tanner shares the strategy, mindset, and grit it takes to keep going when others would quit.


Insights from today’s episode: 



    Tanner’s journey from failed restaurant owner to serial entrepreneur
    The “three-legged stool” that allows entrepreneurs to build massive wealth
    How to optimize an existing business through vertical integration
    Two things that directly impact the success of any new business
    How to balance productive businesses and passion projects
    The biggest risks to keep in mind when forming a business partnership