
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.
Latest episodes

Jun 5, 2025 • 58min
Good Idea? Freelancing as a Family...
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 to go into business with family, today’s episode of
Freelance to Founder is for you. Here we go!
This episode was originally aired on September 21, 2023.
PS: Get featured in an upcoming Q&A! Just visit http://freelancetofounder.com/ask and submit a question.
Support our Sponsors
Our generous sponsors make this show 100% free to you. Support them at the link below.
https://freelancetofounder.com/sponsors
Get your own on-air coaching call
We'd love to feature your business and offer some free on-air advice for growing your business. To see if you're a good fit, click here.
Leave us a review on Apple Podcasts:
If you enjoy the show, can you do us a favor and leave us an honest rating and review on Apple Podcasts? We'll love you forever. Click here to leave a review.
More Recommended Listening:
This show is a part of the Podglomerate, a company that produces, distributes, and monetizes podcasts. We encourage you to visit the website and sign up for our newsletter.
We suggest you also try other Podglomerate shows about entrepreneurship, business, and creativity, such as Rocketship.fm and Creative Elements. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jun 3, 2025 • 22min
[Q&A] Charge by Hour or Project?
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
Support our Sponsors
Our generous sponsors make this show 100% free to you. Support them at the link below.
https://freelancetofounder.com/sponsors Learn more about your ad choices. Visit megaphone.fm/adchoices

May 29, 2025 • 52min
Can You Ever Step Away?
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’re wondering the same, then stay tuned because we answer that and lots more on today’s episode of freelance to founder. Here we go.
This episode was originally aired on April 18, 2024.
PS: Get featured in an upcoming Q&A! Just visit http://freelancetofounder.com/ask and submit a question.
Support our Sponsors
Our generous sponsors make this show 100% free to you. Support them at the link below.
https://freelancetofounder.com/sponsors
Get your own on-air coaching call
We'd love to feature your business and offer some free on-air advice for growing your business. To see if you're a good fit, click here.
Leave us a review on Apple Podcasts:
If you enjoy the show, can you do us a favor and leave us an honest rating and review on Apple Podcasts? We'll love you forever. Click here to leave a review.
More Recommended Listening:
This show is a part of the Podglomerate, a company that produces, distributes, and monetizes podcasts. We encourage you to visit the website and sign up for our newsletter.
We suggest you also try other Podglomerate shows about entrepreneurship, business, and creativity, such as Rocketship.fm and Creative Elements. Learn more about your ad choices. Visit megaphone.fm/adchoices

May 27, 2025 • 20min
[Q&A] Client-Converting Portfolio Tips
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 feature you on an upcoming episode.
Listen to our full-length coaching calls: http://freelancetofounder.com
Support our Sponsors
Our generous sponsors make this show 100% free to you. Support them at the link below.
https://freelancetofounder.com/sponsors Learn more about your ad choices. Visit megaphone.fm/adchoices

May 22, 2025 • 1h 1min
Too Busy to Grow?
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 of Freelance to Founder. Here we go…
This episode was originally aired on September 14th, 2023.
PS: Get featured in an upcoming Q&A! Just visit http://freelancetofounder.com/ask and submit a question.
Support our Sponsors
Our generous sponsors make this show 100% free to you. Support them at the link below.
https://freelancetofounder.com/sponsors
Get your own on-air coaching call
We'd love to feature your business and offer some free on-air advice for growing your business. To see if you're a good fit, click here.
Leave us a review on Apple Podcasts:
If you enjoy the show, can you do us a favor and leave us an honest rating and review on Apple Podcasts? We'll love you forever. Click here to leave a review.
More Recommended Listening:
This show is a part of the Podglomerate, a company that produces, distributes, and monetizes podcasts. We encourage you to visit the website and sign up for our newsletter.
We suggest you also try other Podglomerate shows about entrepreneurship, business, and creativity, such as Rocketship.fm and Creative Elements. Learn more about your ad choices. Visit megaphone.fm/adchoices

May 20, 2025 • 16min
[Q&A] Should I hire a CPA or use a tax software?
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 our full-length coaching calls: http://freelancetofounder.com
Support our Sponsors
Our generous sponsors make this show 100% free to you. Support them at the link below.
https://freelancetofounder.com/sponsors Learn more about your ad choices. Visit megaphone.fm/adchoices

May 15, 2025 • 34min
Should I Even Try?
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 Founder.
Oh, and really quickly before we start: the audio on this episode is a bit rough. We’ve done our best to clean it up. But between the audio and Rakesh’s very thick accent, you may have to focus extra to follow along. But we believe it’s important to share stories from all over the world whether a guest has a quality mic setup or a flawless accent. Thanks for supporting us as we support freelancers around the world. Ok, now on to the show.
This episode was originally aired on April 8, 2024.
PS: Get featured in an upcoming Q&A! Just visit http://freelancetofounder.com/ask and submit a question.
Support our Sponsors
Our generous sponsors make this show 100% free to you. Support them at the link below.
https://freelancetofounder.com/sponsors
Get your own on-air coaching call
We'd love to feature your business and offer some free on-air advice for growing your business. To see if you're a good fit, click here.
Leave us a review on Apple Podcasts:
If you enjoy the show, can you do us a favor and leave us an honest rating and review on Apple Podcasts? We'll love you forever. Click here to leave a review.
More Recommended Listening:
This show is a part of the Podglomerate, a company that produces, distributes, and monetizes podcasts. We encourage you to visit the website and sign up for our newsletter.
We suggest you also try other Podglomerate shows about entrepreneurship, business, and creativity, such as Rocketship.fm and Creative Elements. Learn more about your ad choices. Visit megaphone.fm/adchoices

May 13, 2025 • 13min
[Q&A] Can I Put In-House Work in My Portfolio?
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 you think this will work to close deals?
If you were a company that would be reviewing my portfolio, would you think that I'm experienced or just someone trying to fool you?”
Note: we are not attorneys, and we will not even touch the question of if it’s something legal or not. We are not providing legal advice in any way. This type of advice should be provided by a certified professional, and we are not.
This episode was originally aired in July 5th, 2022.
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
Support our Sponsors
Our generous sponsors make this show 100% free to you. Support them at the link below.
https://freelancetofounder.com/sponsors Learn more about your ad choices. Visit megaphone.fm/adchoices

May 7, 2025 • 48min
Is a VA a Good First Hire?
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, 2023.
PS: Get featured in an upcoming Q&A! Just visit http://freelancetofounder.com/ask and submit a question.
Support our Sponsors
Our generous sponsors make this show 100% free to you. Support them at the link below.
https://freelancetofounder.com/sponsors
Get your own on-air coaching call
We'd love to feature your business and offer some free on-air advice for growing your business. To see if you're a good fit, click here.
Leave us a review on Apple Podcasts:
If you enjoy the show, can you do us a favor and leave us an honest rating and review on Apple Podcasts? We'll love you forever. Click here to leave a review.
More Recommended Listening:
This show is a part of the Podglomerate, a company that produces, distributes, and monetizes podcasts. We encourage you to visit the website and sign up for our newsletter.
We suggest you also try other Podglomerate shows about entrepreneurship, business, and creativity, such as Rocketship.fm and Creative Elements. Learn more about your ad choices. Visit megaphone.fm/adchoices

May 5, 2025 • 12min
[Q&A] Best Software for Getting Paid Faster?
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 coaching calls: http://freelancetofounder.com
Support our Sponsors
Our generous sponsors make this show 100% free to you. Support them at the link below.
https://freelancetofounder.com/sponsors Learn more about your ad choices. Visit megaphone.fm/adchoices