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. (This episode was originally aired on October 26, 2023). PS: Get featured in ...
Jul 10, 2025•57 min•Season 31Ep. 9
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. To submit your question, visit FreelanceToFounder.com/ASK, and we'll feature yo...
Jul 08, 2025•22 min
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 walk her through a few key social media strategies that’ll also help you build...
Jul 03, 2025•39 min•Season 31Ep. 8
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 feature you on an upcoming episode. Listen to our full-length coaching calls...
Jul 01, 2025•20 min
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 course, as marketing geeks Clay and I jump in with some of our best ad...
Jun 26, 2025•54 min•Season 31Ep. 7
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, visit FreelanceToFounder.com/ASK, and we'll feature you on an upcomin...
Jun 24, 2025•15 min
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 clients. Stick around for this fun brainstorming session starting right a...
Jun 19, 2025•49 min•Season 31Ep. 6
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 ...
Jun 17, 2025•12 min
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 solid advice for hiring the best freelancers. This episode was originall...
Jun 12, 2025•53 min•Season 31Ep. 9
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 your question, visit FreelanceToFounder.com/ASK, and we'll feature you on an up...
Jun 10, 2025•19 min
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 Harris, CEO of AthLife, explores how leaders create lasting impact by ...
Jun 09, 2025•46 min
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 f...
Jun 05, 2025•58 min•Season 31Ep. 8
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%...
Jun 03, 2025•22 min
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 m...
May 29, 2025•52 min•Season 31Ep. 7
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-lengt...
May 27, 2025•20 min
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 Se...
May 22, 2025•1 hr 1 min•Season 31Ep. 7
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 ...
May 20, 2025•16 min
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 ...
May 15, 2025•34 min•Season 31Ep. 5
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 tha...
May 13, 2025•13 min
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://freelancetof...
May 07, 2025•48 min•Season 31Ep. 4
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 ...
May 05, 2025•12 min
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 of a freelancer or agency. That and lots more questions are just ahead o...
May 01, 2025•1 hr•Season 31Ep. 3
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 your question, visit FreelanceToFounder.com/ASK, and we'll feature you on an up...
Apr 29, 2025•19 min
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 in place to bring in predictable new work. Her annual goals are lit...
Apr 24, 2025•1 hr•Season 31Ep. 2
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% fre...
Apr 22, 2025•22 min
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 joining. Here we go! This episode was originally aired on August 17, 2...
Apr 17, 2025•53 min•Season 31Ep. 1
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 ...
Apr 15, 2025•20 min
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. This episode was originally aired on February 29, 2024 PS: Get featured in ...
Apr 10, 2025•55 min•Season 30Ep. 10
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 Suppor...
Apr 08, 2025•16 min
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 single platform that she manages? We’ll discuss that and more on today’...
Apr 03, 2025•52 min•Season 30Ep. 9
