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
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...
Mark as Played
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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May 5, 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 fu...
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May 1, 2025 • 60 mins
On today’s show: What should you do when you’re not getting the kind of respect you deserve from your clients?
That’s just one of many questions we got today from our guest, Cathal, calling in from Germany.
A few times now, Cathal has been hired by a manager only to later have that manager’s team give him pushback once he gets to work.
So, we work with him on a few ideas on how to get everyone on board with the outside help ...
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April 29, 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 yo...
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April 24, 2025 • 60 mins
On today’s show, if you get most of your clients from referrals, is that a good thing? Or is your business at risk of failing?
You’re about to hear a coaching call with Dwaynia, who’s calling in from Alabama in the USA. Dwaynia has a great writing business going. She’s working with clients she loves and has a small team to support her.
But, Dwaynia literally lies awake at night worried about not having a client generation system ...
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April 22, 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://freelancetofounder.com
...
Mark as Played
April 17, 2025 • 53 mins
On today’s show: Do lead magnets really work? Like, can you actually get new clients by giving away something for free first? Or are they a waste of your time?
I’m flying solo today on a coaching call with Garrett—who has questions about using AI to generate lead magnets, how to price his work when he has a unique offering and non-traditional clients, and more.
It’s all in today’s episode of ‘Freelance to Founder.’ Thanks for joi...
Mark as Played
April 15, 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 we'll...
Mark as Played
April 10, 2025 • 55 mins
On today’s show: you’re dead without a vision for your business.
That’s because without a vision—or a north star—to guide your business, you can very easily end up chasing the wrong things.
In today’s episode, we chat with Alan, who’s ready to grow his family business, but he’s not sure
where to start when it comes to strategy and processes.
If you find it hard knowing where to start, this episode is for you. Here we go.
Thi...
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April 8, 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.
Listen to...
Mark as Played
April 3, 2025 • 52 mins
On today’s show: should you spread yourself across each of your client’s project management tools? Or should you make them join yours?
It’s a question Taylor’s facing as she grows her business.
We spoke with Taylor about a year ago, and things are going great.
But she works with so many clients now; they each have their preferred project management tool.
So, should she keep going from tool to tool? Or make her clients join a...
Mark as Played
April 1, 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. Do...
Mark as Played
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