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How to Scale A Business After Failure And Be A Multi-Million Dollar Success with Shawn Finnegan
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LOVE THIS PODCAST? LEAVE US A REVIEW ON APPLE: Creative Entrepreneur: A Podcast For Business Growth, Strategy and Monetization - Podcast - Apple Podcasts
Most people know Shawn Finnegan as the powerhouse behind some of the fastest-growing brands in the country—think Crumbl Cookies, Swig, and Tax Hive. But before he was partnering with "Shark" Kevin O’Leary, he was staring at a $1.5 million loss and a bank account that couldn't cover payroll.
In this episode, Shawn joins Dom and Julie to get real about the "ugly" side of serial entrepreneurship. He breaks down why failure is just a collection of data points, how he conquered the "pounce per square inch" pressure of debt, and why he attributes his biggest breakthroughs to being a "girl dad."
The Highlights:
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The $1.5M Disaster: Shawn tells the story of his first live events business in 2009—how a hurricane, a $70k speaking fee for David Bach, and a room full of empty chairs taught him everything he knows about persistence.
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Pitching Mr. Wonderful: What it’s actually like to text Kevin O'Leary and pitch a business that turns into a massive partnership.
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The "Micro-Intention" Trick: Shawn’s secret for networking: pausing at the door of every room to decide exactly how he wants to show up. (It’s the difference between hiding on your phone and making a million-dollar connection.)
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The Cookie Debate: We settle the score on the best and worst cookies. From the "angel-singing" Dubai Chocolate Brownie to why Shawn refuses to eat a dry Chips Ahoy.
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Lessons from his Daughters: A powerful story about how Shawn’s 19-year-old daughter taught him more about human connection than any business mentor ever could.
Favorite Moments & Quotes:
On Resilience: "Every storm runs out of rain. You just have to put your shoes on the next day and go back to work."
On Authenticity: "If you paint a picture that everything is cotton candy and rainbows, people won’t believe you. Transparency is your friend."
On Strategy: "I realized my number one failure wasn't operations or marketing—it was that I stopped building relationships. I vowed that day to get comfortable being uncomfortable."
Mentioned in this Episode:
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Tax Hive: How Shawn and Kevin O'Leary are helping small business owners stop overpaying the IRS. www.taxhive.com
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Crumbl Cookies & Swig: The secrets to scaling "treat" culture.
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Brian Tracy: The mentor who gave Shawn the "Girl Dad" reading list that changed his life.
Find Shawn on Instagram-- @finneganshawn
Love the show? If Shawn’s energy fired you up, leave us a review and subscribe! We’ll see you next week—keep creating.
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