Freelance to Founder
Freelance to Founder is a unique call-in show helping real-life freelancers grow their businesses and escape the feast-famine lifestyle. The podcast is co-hosted by Clay and Preston, two former freelancers who have started, built, and even sold six- and seven-figure businesses of their own. If you enjoy content fromThe Futur, Being Freelance, The Accidental Creative, Smart Passive Income, or The Side Hustle Show, then you'll love Freelance to Founder. Catch the Tuesday Q&A episodes, dive deeper with Thursday's call-in episodes, or join us on the air and take the next step on your journey from ... freelance to founder.
Episodes
July 10, 2025 • 56 mins
On today’s show, which comes first: hiring to free up time to land big clients or landing big clients to pay for hiring.
It’s a chicken and egg situation that our guest Zach has been stuck on.
We do our best to answer that question, plus a few others he has, including how to combine two completely different offerings into one killer monthly recurring offer.
It’s all in this episode of ‘Freelance to Founder’—here we go.
...
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July 8, 2025 • 22 mins
On today’s show, where do you start when it comes to making a marketing plan for your business?
That’s what Thomassina asks us and—since Clay and I both have extensive marketing backgrounds—we end up having a lot to say about it.
If you’re not sure where to start when it comes to marketing, then this episode is for you.
This is Freelance to Founder. Here we go!
This episode was originally aired on January 23, 2024.
T...
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July 3, 2025 • 38 mins
On today’s show, we talk with Mannat, a student calling from India, with questions about her freelance business.
Mannat is a typographer—she works with lettering and fonts.
But every time Mannat posts her work on social media, she gets packaging design clients and others who don’t match her target audience.
This leaves Mannat asking, “what exactly should I be posting on social media to attract my ideal client?"
We wal...
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July 1, 2025 • 19 mins
On today’s show: can you become a millionaire as a freelancer?
Podcast listener Suman wrote in with that simple yet not-so-simple question, and we do our best to reveal whether or not you can get rich working as a freelancer.
It’s all in this episode of Freelance to Founder. Here we go!
This Q&A episode was originally aired on September 26, 2023.
To submit your question, visit FreelanceToFounder.com/ASK, and we'll fea...
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June 26, 2025 • 53 mins
Have you ever thought: “if I can just get the attention of more people, I could close more clients and grow my business”
That’s where we find today’s guest, Jay. He’s a web developer and SEO expert in Kentucky, USA. And Jay’s only been freelancing for a few months. He’s off to a great start having already closed a half-dozen monthly recurring clients.
Jay’s biggest question is how to get more volume. Or more awareness. So, of...
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June 24, 2025 • 14 mins
On today’s Q&A episode, if you give your client full ownership of your creative work, how much should that cost, and how exactly do you even do that?
That’s the question Nicole hits us with, and it opens up another discussion on who should own your work in the first place.
It’s all in this episode of Freelance to Founder. Here we go.
This Q&A episode was originally aired on December 26, 2023.
To submit your question, vi...
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June 19, 2025 • 49 mins
On today’s show: do you keep hearing how important networking is, but you really just don’t enjoy it?
In this episode, we chat with Morgan, a freelancer from Chicago. Morgan can see the potential in networking with local clients, but can’t quite figure out how to enjoy it.
So, Clay and I start brainstorming a few fun and exciting ways she can leverage her unique talents to network with local business owners and potential cl...
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June 17, 2025 • 12 mins
Today’s question comes from our free Mastermind group on Facebook.
Darielle asks: "What's the BEST Software for getting paid faster?"
Getting paid for your work FAST is key, but how do you make it happen?
You'll get the answer here!
This Q&A episode was originally aired on August 8th, 2023.
To submit your question, visit FreelanceToFounder.com/ASK, and we'll feature you on an upcoming episode.
Listen to our full-length ...
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June 12, 2025 • 53 mins
On today’s show, have you ever thought: if I could just find the right person to hire, I could scale up my business.
That’s how Virginia from Argentina feels about her unique content marketing company.
The challenge? Virginia’s company develops content around witchcraft and spiritualism—so she needs teammates who speak fluent English, write well, and understand her unique niche.
It’s a tall order, but Clay and I offered so...
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June 10, 2025 • 18 mins
On today’s Q&A episode, what are the best tools to use as your freelance business grows?
That’s what Cesar asks us because his business is outgrowing tools like Google Drive.
So, Clay and I launch into our best advice on what makes a good business tool and what makes your business worse…
It’s all in this episode of Freelance to Founder. Let’s go!
This episode was initially aired on September 12, 2023.
To submit you...
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June 9, 2025 • 46 mins
Sharing an episode of the Superhero Leadership podcast, hosted by Marvel's former CEO and legendary turnaround expert, Peter Cuneo. Each week, Peter is joined by top performers from business, media, and beyond, leaders who have mastered the art of impact, resilience, and vision. Together, they explore Peter’s 32 leadership essentials, revealing what it really takes to rise, inspire, and lead with purpose. In this episode, Jon Harri...
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June 5, 2025 • 58 mins
Is freelancing as a family a good idea? Can it actually work?
That’s part of what we get into with our call-in guest, Dave.
Dave is the father of 3 talented young developers. Together, they’ve started an agency.
Well… sort of.
As we talked with Dave, we uncovered this: family dynamics are not the same as business dynamics. And sometimes, managing both can present a real challenge.
If you’ve ever wondered whether or not ...
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June 3, 2025 • 21 mins
On today’s Q&A episode, if a client is willing to pay by the hour or by the project, which one should you choose?
That’s part of Pennygoo’s question, and our answer might surprise you… Here we go!
This episode was originally aired on September 5, 2023.
To submit your question, visit FreelanceToFounder.com/ASK, and we'll feature you on an upcoming episode.
Listen to our full-length coaching calls: http://freelanceto...
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May 29, 2025 • 51 mins
On today’s show: Can you ever step away from your business? Or are you doomed as an entrepreneur to never enjoy a vacation or time off ever again?
That’s just part of what we talk about with our guest Jim, who’s calling back for a second time on today’s episode.
Jim has quit his job and taken his business full-time. But now he wonders: how do I take the next step so I can work more ON my business than IN my business.
If you’r...
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May 27, 2025 • 20 mins
In this Q&A episode, Oliver asks us what it takes to create a portfolio that actually brings in new long-term clients. And since Clay and I are real marketing geeks, we have quite a few ideas for turning your sleepy portfolio into a client-converting machine. It’s all in today’s show, and it starts right now.
This episode was originally aired on August 29, 2023.
To submit your question, visit FreelanceToFounder.com/ASK, and...
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May 22, 2025 • 61 mins
On today’s show: Do you ever feel like you’re just way too busy to actually spend time growing your business?
If so, you’re not alone. We chatted with Will Gibbons, who works with cool clients like Peloton, 3M, and Vizio.
But Will’s got a problem. A great problem. He’s got too much work. Which means he’s busy.
And he’s worried he doesn’t have time to grow.
Clay and I help him punch through those barriers in this episode ...
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May 20, 2025 • 16 mins
Today’s question comes from our free Mastermind group on Facebook.
Anna Keith asks: "I’m getting ready to do my taxes and am considering trying software rather than hiring a CPA.
What insights or pros/cons about using software vs. hiring a professional do you have?"
This episode was originally aired on May 3, 2022.
To submit your question, visit FreelanceToFounder.com/ASK, and we'll feature you on an upcoming episode....
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May 15, 2025 • 34 mins
On today’s show: is it even worth trying to grow your freelance business?
That’s where Rakesh finds himself. He gets most of his clients from freelancing platforms like Upwork.
And the market for web designers and developers is just so saturated, he doesn’t even know if he should continue with his business.
If you’ve ever felt this way, today’s show is for you. It all starts right now on this episode of Freelance to Founde...
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May 13, 2025 • 13 mins
This episode's question came in via email.
Nico works as a designer for a company right now, and he wants to start freelancing on the side and build a business.
He said, “I was thinking of creating a portfolio, including the projects I've completed in my current company, but in a fictitious way (use different names, organizations, etc.) Also, state that this is a fictional project but that the process and outputs are the same...
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May 7, 2025 • 47 mins
On today’s show: Is a VA a good first hire in your company?
We’re joined by call-in guest Nils, who wants to know when and how to hire a VA—a virtual assistant.
But Clay and I slam on the brakes and force Nils to answer the question: Is a VA even the best first hire to make?
The answer might surprise you. It’s all on today’s episode of Freelance to Founder. Let’s go!
This episode was originally aired on September 7th, 2...
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