1530: Scale to Billions: Pivot, Build AI, and Grow Your Business with Entrepreneur & Investor Jason Criddle
Jason Criddle is the founder and managing partner of a multi-entity private investment and technology ecosystem, including Smarter Holdings, Dominate.AI, and Jason Criddle & Associates. Known for scaling businesses through strategic development, acquisition, and a passionate approach to helping entrepreneurs, Jason leverages deep expertise in AI, automation, publishing, and behavioral coaching to drive results for both startups and established organizations.
In this episode of Marketer of the Day, Jason returns after more than a decade to share how his journey from personal health battles to overseeing billion-dollar companies has shaped his no-nonsense philosophy on business growth, digital transformation, and personal fulfillment. Together with Robert Plank, they discuss why most entrepreneurs struggle to scale, the importance of consistent reinvention, actionable strategies for making your business scalable, and how to build infrastructure that lasts. Jason breaks down the value of pivoting early, highlights the role of mentors, stresses the need for clear customer experiences, and shares why celebrating wins big or small is essential along the sometimes-lonely road to legitimacy and authority.
Quotes:
“If your business isn’t producing customers or revenue, it’s not a business, it’s an expensive hobby.”
“You have to be willing to be bad before you can be great. Growth begins the moment you push past the fear of starting.”
“Showing up is a win. If you earned even one today, celebrate it especially with the people who matter most.”
Resources:
Podcast: Play in new window | Download (Duration: 46:20 — 63.6MB) | Embed
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