freelance to founder

a new podcast from Millo.

Stories from solo to scale.

The real stories of freelancers & solopreneurs who have scaled their business to something much bigger than themselves.

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Season 3 is sponsored by

with additional support from

freelancer to founder podcast ladder

"I dig the honest talk and advice in Freelance to Founder!"
—Paul Jarvis, author & podcaster at

"Anyone who's ready to scale their one-person business should listen to Freelance to Founder." —Nick Loper, host of The Side Hustle Show

3.8 From flailing freelancer to a $500,000/month "unlimited design" business with Russ Perry of Design Pickle

After realizing he wasn't cut out for freelancing or agency life, Russ Perry built a multi-million-dollar business on the back of a crazy idea: sell unlimited graphic design services for unbelievably cheap.

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3.7 From struggling design blogger to building a huge six-figure business with Tom Ross of Design Cuts

Tom Ross used to be a design blogger getting hundreds of thousands of views every month. But he quickly realized almost none of those visitors really cared about him, his brand, or his business. That's when Tom pivoted to build Design Cuts—a decision that would lead him to build one of the most engaged (and profitable) design communities on the web.

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3.6 From 8-yr-old computer whiz to selling his company to Stripe with Courtland Allen of Indie Hackers

When Courtland Allen was an 8-year-old tinkering with computers and teaching adults around him how the machines worked, he probably never imagined that many years later he would build a small company that would eventually be acquired y tech giant, Stripe.

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3.5 From college dropout to $828,000 in monthly recurring revenue with Nathan Barry of ConvertKit

When Nathan Barry dropped out of college a few years ago, he never dreamed he'd soon be running a company that generates over $800,000 every month in recurring revenue. But that's exactly what has happened. And in today's episode we learn how he did it.

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3.4 From quitting law school to building a copywriting empire with Joanna Wiebe of Copy Hackers

Joanna Wiebe thought law school was the right path for her. But after a day—yes, literally one day—she realized she made a terrible mistake. Since then she has built one of the most well-known copywriting brands on the internet: Copy Hackers.

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3.3 From losing everything to building a massive podcast career with Michael O'Neal and 'The Solopreneur Hour'

How many people do you know making a good living as a professional podcaster? Probably not many. In today's episode, you'll hear the story of Michael O'Neal and learn what it takes to build a creative business of any kind as we hear how he became the host of a very popular podcast: 'The Solopreneur Hour.'

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3.2 From financial analyst to million-dollar blogger with Michelle Schroeder-Gardner and 'Making Sense of Cents'

Just a few years ago, Michelle Schroeder-Gardner was a financial analyst with loads of student debt. Now her blog, 'Making Sense of Cents,' brings in over a million dollars annually.

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3.1 From high-school web developer to teaching freelancers how to double their business with Brennan Dunn

Brennan Dunn started freelancing as early as high-school. Now, he teaches other freelancers what it takes to build a thriving business & he runs a couple of growing businesses himself.

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3.0 Season 3 is coming—and we've got Brennan Dunn, Michelle Gardner, Michael O'Neal and lots more!

We're back with an all-new season of 'Freelance to Founder!' This season, you'll hear the stories of incredible freelancers and solopreneurs like Brennan Dunn of 'Double Your Freelancing,' Michelle Gardner of 'Making Sense of Cents,' Michael O'Neal from 'The Solopreneur Hour Podcast' and lots more! Get ready, it's going to be a great season.

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Season 2

2.1 From washing windows to building a massive online brand — the story of Sean McCabe and the seanwes brand

Episode 1 tells the story of Sean McCabe, founder of seanwes. Sean freelanced as a hand-lettering specialist, but ultimately turned the lessons he learned from that nicheinto a successful online business.

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2.2 From getting fired to building a thriving creative agency - the story of Clay Mosley and Rock City Digital

Episode 2 introduces you to Clay Mosley, founder of Rock City Digital agency in Little Rock, Arkansas. Clay went from self-proclaimed job hopper to creative visionary and CEO of an unorthodox agency in the Midwest.

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2.3 From kindergarten teacher to Kickstarter success & thriving mompreneur - the story of AshLee Winterrose

Episode 3 brings you AshLee Winterrose. AshLee and her husband were dealt a challenging blow while still in college, forcing her to become the primary family provider. Hear how she went from meager teacher's salary to budding entrepreneur.

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2.4 From a Boeing cubicle to making videos for Pat Flynn, John Lee Dumas, Chris Ducker & more - the story of Caleb Wojcik

Episode 4 tells the story of Caleb Wojcik, who purposely avoided the self-employed path his father took...before ultimately being pulled into it after the corporate world let him down. Hear how he navigated from employee to employer.

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2.5 From project manager to highly sought-after hand-lettering instructor - the story of Becca Courtice

Episode 5 introduces you to Becca Courtice. She was a sports nut early in life, and a project manager after university, What does she do now? She has a highly successful, full-time business as a calligraphy instructor.

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2.6 From college drop-out to building a massive social selling business — the story of Phil Gerbyshak

Episode 6 welcomes Phil Gerbyshak. As Phil left the Navy, he was quick to dive into the digital world. As his career moved along, so did his mastery of the web for ethical connections. He now teaches social selling as one of several founders of Vengreso.

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2.7 From receptionist to designing for Google and becoming a bestselling author - the story of Sarah Cooper & the Cooper Review

Episode 7 introduces you to Sarah Chooper. Sarah is the hilarious author of the best-selling book, "100 Ideas to Look Smart in Meetings," a follow-up to her post with 10 ideas.

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2.8 From fortune 500 companies & failed startups to building a successful business on their terms - the story of Fizzle founders Corbett Barr & Chase Reeves

Our final episode for Season 2 brings you Corbett Barr and Chase Reeves, together, as co-founders of We especially cover the mindset of a successful online business builder. The perfect episode to wrap up an incredible season.

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Season 1

1.0 Season One Trailer

Season 1 of Millo's all-new podcast 'Freelance to Founder' is about to launch! Here's a peek at what to expect this season.

1.1 From stay-at-home mom to multi-million dollar brand

Courtney didn't want to start just another mommy blog. She wanted to make money...and fast. After just 3 years, her fashion business grew to employ dozens of moms and bring millions in revenue.

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1.2 From getting paid pennies in royalties to selling art direct to buyers

Greg was an artist getting paid pennies on the dollar in royalties for his religious artwork. But after his son Nate stepped in to help build a direct-to-consumer ecommerce business, profits soared.

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1.3 From a single freelance designer to an agency making millions

Bianca started out as a one-woman graphic design "agency" and has built a thriving Aussie web design business with 20 employees and bringing in millions of revenue along the way.

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1.4 From art enthusiast to empowering women in Nepal

Adrienne never expected a vacation to Nepal would lead to, not only her eventual marriage, but the beginning of an art business that empowers female artists in Nepal.

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1.5 From college grad to working for ESPN, Oprah, & Time Magazine

C.J. was a no-name freelance photographer who walked into the offices of Time Magazine to pitch his work...and got a job! Years later, he has worked for brands like Oprah, ESPN, and Time Magazine.

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1.6 From cubicle-doomed to getting his brand featured on TODAY Show & in the Superbowl

Michael was an accountant with a dead-end job making him miserable. So he decided to purchase a small local coffee business. After attempting a unique online business model, he came within 2 months of complete failure. But after getting on the TODAY Show and in the Superbowl, his brand is now growing like crazy.

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1.7 From designing video games to getting hired by major brands to create custom illustrations & art

Ever since we was a little kid, Howard loved fantasy games like Dungeons and Dragons. But little did he know he'd grow up be hired by Dungeons and Dragons plus other huge gaming brands like Blizzard. Today, Howard does commission work for enormous brands and sells one-of-a-kind commissioned art.

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1.8 From freelance designer to building a luxury fashion brand

Jeff started out with a question: why was it so difficult to find fresh, high-quality, unique fashion items in a modern aesthetic? Then he set out to build Ugmonk—a company that sells luxury items with modern design.

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