Dwayne Kerrigan

In this conversation, Dwayne sits down with entrepreneur and creator Scott Clary, host of the Success Story Podcast with 30M+ downloads. Scott opens up about his unlikely path from a government-family upbringing to becoming a media-first entrepreneur, the early exposure that ignited his drive, and why curiosity and tenacity can outperform almost anything.
Scott walks through how small companies create the best “entrepreneurial classrooms,” why every creator should think like a founder, and how success hinges on defining your personal North Star before you start sprinting. The episode dives deep into AI disruption, content strategy, internal vs. external locus of control, personal branding, and how businesses of every size can prepare for the next wave of transformation.
Scott offers tactical clarity on building a media-first business, testing content efficiently, disrupting yourself before the market does, and why attention—sustained over time—is the most valuable commercial asset any entrepreneur can build.
EPISODE HIGHLIGHTS
03:53 - Scott's telecom background
08:22 - How working at a small company provides exposure to all aspects of business
14:27 - The importance of curiosity as a foundational entrepreneurial skill
17:25 - Warning: Be careful what you pursue - success requires understanding your true goals
23:25 - Finding your North Star: Be rigid in goals but flexible in execution
28:10 - Identifying what energizes you through trial and error
32:33 - Building a business while working full-time: The side hustle strategy
38:15 - How AI is disrupting businesses and the need for constant self-disruption
43:15 - The four types of leverage: Capital, technology, people, and media
51:00 - The power of AI to make individuals 10-100x more productive
01:06:30 - Internal vs external locus of control and taking ownership
01:13:30 - Content creation strategy: Testing ideas at scale on forgiving platforms
01:27:26 - How media and AI are already transforming traditional industries like restaurants
KEY TAKEAWAYS
Many people pursue success without clarity on what they actually want — a lifestyle business, a scalable company, privacy, or fame. If you have tenacity and skill, you’ll eventually succeed… so make sure you're climbing the right mountain.
Scott attributes almost everything in his career to relentless curiosity — the willingness to ask questions, learn widely, and self-educate.
The companies thriving in this era are disrupting themselves before someone else does. Every role can be up-leveled 10x–100x with the right tools and mindset.
Capital, technology, people… and media. If you don’t build a personal or company brand, someone in your industry eventually will — and they will take market share.
Social content is the best testing ground for messaging. Use it to refine your voice, validate ideas, influence sales scripts, and improve marketing before spending ad dollars.
The companies, creators, and leaders who show up consistently earn trust — which compounds into opportunity.
Entrepreneurs who take ownership — good or bad — create their own luck and navigate volatility more effectively.
QUOTES
From Scott Clary:
From Dwayne Kerrigan:
Scott Clary is a dynamic entrepreneur, investor, and author. He hosts the Success Story podcast, where he has candid conversations with some of the most prolific business & thought leaders in the world.
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Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.