Freelance to Founder Podcast Art

Real freelancers. Real growth.

Freelance to Founder is a unique weekly podcast featuring coaching calls co-hosted by Clay and Preston, two freelancers-turned-business-builders. Instead of typical interviews, each week a new freelancer calls in to talk with Clay and Preston with one goal in mind: overcoming the feast/famine cycle and scaling their service business. The highly acclaimed, top-rated podcast is a weekly dive into what it really takes to go from freelance to founder.

In partnership: Millo, Dripify, Podglomerate

New shows every Thursday. Subscribe with your favorite.

S18 E7 — 57 min

Should you tell your boss about your business?

If you’re working as a side-hustler, this can be a tricky situation. It’s where today’s guest Berna finds herself. After working on a side-project for a while, she’s ready to promote it, but isn’t sure how to get the word out without upsetting her boss. So Clay and I walk her through our o ....

13 min

[SHORT] When Sub-Contractors Don't Deliver

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. Today’s question comes from our free Mastermind gro ....

S18 E6 — 52 min

Getting Clients to Treat You Like an Agency

On today’s show, I’m joined by a good friend of mine, Chelsea Baldwin as a special guest coach. Together, we coach Australian freelancer-turned-agency-builder Caroline. She has built up a nice freelance business and has begun to work with subcontractors to begin scaling her business. But she’s ....

15 min

[SHORT] How do I find product/market fit?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. On today's show, Chase calls in with a question: What' ....

S18 E5 — 58 min

The Power of Personal Brand

On today’s episode, we have a coaching call with Denise, a freelancer from South Carolina, USA.  Denise works in higher education and is happy with the way her freelance business is going. But after finding some early success in e-learning thanks to Covid and other factors, Denis is ready to bran ....

17 min

[SHORT] Is Freelancing Really Worth It?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. today's question comes from Travis Hostetter. He says ....

S18 E4 — 55 min

Crushing Your Time Management

On today’s episode: how can you balance client work with growing your business? It’s a question we got from James who calls in from New Zealand.  James has been growing his web security and maintenance company for about a year and he’s starting to feel the all-too-common pressure of getting m ....

15 min

[SHORT] Responding to an Impatient Client

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. Today's question comes from Prithvi in the Millo Mast ....

S18 E3 — 69 min

Getting Attention from Decision-Makers

On today’s episode: how can you actually get the attention of the perfect audience for your business? It’s a question we got from Roopika, who called in from India. She’s got a really unique business—you’ll hear more about that real soon—and she’s wondering how she can get in front of  ....

20 min

[SHORT] How Can I Build My Confidence?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. Robert shared this question in our Millo Mastermind G ....

S18 E2 — 55 min

How to Generate the Best Leads

On today’s show: do you ever wonder how to generate some of the best leads possible?  For most freelancers and agencies, filling your pipeline with quality leads is not only critical to your business’s health, but also one of the toughest problems to solve. That’s how our guest Morgan feels r ....

13 min

[SHORT] How to Handle 5 Common Nightmare Clients

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. We’ve had a lot of you send questions about difficu ....

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