Freelance to Founder Podcast Art

Clay and Preston have each grown their own one-person businesses to something much bigger and now they offer weekly coaching calls with freelancers ready to do the same. Your weekly dose of real-world, practical, actionable advice to take your service-based business to the next level—with occasional surprise guest experts or deep dives on must-have skills for success.

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This week on Freelance to Founder:

S11 E8 — Getting More Clients (as an Introvert)

On today’s show, I’m joined again by my friend Matt Olpinski for our coaching call with side-hustler-turned agency-builder Jason Frostholm. After working on the side for years, Jason and his wife finally decided to take their freelancing full-time and build an agency together. That was right bef ....

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More recent episodes:

S E — Introducing 'Creative Elements'

After working with creatives for 10+ years, Clay and I know it can be hard making a living from your art and creativity. If your creative business needs a little boost, I suggest you listen to Creative Elements—a really great podcast from my friend Jay Clouse. Creative Elements is a highly produce ....

S11 E7 — 3 Ways to Finally Raise Your Prices

Today we have a coaching call with Joseph, a digital nomad working in Mexico. Joseph is building his Wordpress development company on the side of his day job with dreams of becoming a full-time entrepreneur. But there’s one major thing standing in Joseph’s way. As you’ll hear him explain durin ....

S11 E6 — Should You Do Your Own Marketing?

Today’s coaching call is with Andy who’s calling in from Colorado, USA. And while Andy runs a business that Clay and I know virtually nothing about, he’s facing a question we have lots of answers to: Should Andy do his own marketing? He’s already working 40-50 hours a week in his business an ....

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S11 E5 — Revenue on Autopilot—Is It Really Possible?

Have you ever found yourself approaching burnout in your business and wondered: is there any way to generate revenue on autopilot? On this episode, Clay and I hit record on a rather personal conversation we were having about our businesses. The question is: can we make enough money on autopilot to  ....

S11 E4 — Getting Press as a Freelancer (from the Editor of Entrepreneur Mag)

On today’s episode Clay and I are joined by the editor of Entrepreneur Magazine, Jason Feifer to talk about how to get press for your freelance business. Whether you want to get more visibility to your brand or attract new clients using earned media, this conversation with Jason will give you acti ....

S11 E3 — Are You Attracting the Wrong Clients?

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 everytime Mannat posts her work to social media, she gets packaging design clients and others reaching out who just don ....

S11 E2 — Unleashing the Power of Local Clients

Today’s coaching call is with Keegan who’s calling in from Louisiana, USA. Keegan is building a web design business (something Clay knows a lot about) on the side of his day job (something I have tons of experience in). And while Keegan has a very clear picture of where he’s going, he’s not  ....

S11 E1 — Hiring 50 Contractors in a Year (Whew!)

On today’s show, we talk with Karl who’s holding on tight while his writing business is growing fast.  After writing for a few highly technical development blogs, Karl’s business exploded and he now works with 50 writers to deliver articles for his clients. And while Karl is crushing it by so ....

S10 E12 — Close 90% of Clients (without Proposals)

On today’s episode we chat with Brady, who is building a web design business from his home in northern Idaho, USA. Brady has already built up a small team of contractors and aims to get the business running almost on autopilot in the next 6-12 months. To do that, he’s got to first perfect his sa ....

S10 E11 — Coaching at Scale

On today’s episode, we chat with Brendan—a sales consultant who wants to scale his business to something bigger. And while he finally started hiring people to help him scale, he’s still a bit unsure about a path forward. He’s working on a course for more passive income and he’s trying to t ....

S10 E10 — How to Speak Your Clients' Language

On today’s show, we chat with Jon who’s a physical product designer and prototyper.  Jon’s got a highly technical business—which you’ll see as we chat with him on the episode today. That means that Jon is very smart when it comes to product design and 3D printing, but has a hard time tran ....

S10 E9 — Should You Branch Out or Niche Down?

On today’s show, we chat with Christine, the founder of Bryant Creative Company. Christine has a nice freelance business where she works on graphic design and branding for her clients.  But over time, Christine has also begun to offer additional services such as web design—which, frankly, she d ....

S10 E8 — Do You Have the Wrong Target Audience?

On today’s show we chat with Augusto who’s running a local branding and video marketing company in the United States. Augusto has chosen to target local latino businesses because he feels they’re underserved and can really use his expertise. But Augusto keeps hitting a wall: his target audienc ....

S10 E7 — You've Been Lied to About "Work/Life Balance"

On today’s episode we chat with Adii Pienaar who recently published a book titled Life Profitability: The New Measure of Entrepreneurial Success. As someone who’s very motivated by the lifestyle that freelancing and entrepreneurship can offer, I was intrigued when I first learned about Adii’s  ....

S10 E6 — Do Clients Treat You Like an Expert? or Employee?

On today’s episode, we have a conversation with Matt Essam who helps freelancers attract and find their dream clients. Have you ever felt like you are more of an employee than a partner when it comes to your client relationships? Maybe you feel like you don’t have any creative input on your proj ....

S10 E5 — Collabs vs. Hiring

On today’s show, we check in with Margaret Ryland. Now, if that name sounds familiar, that’s because Margaret joined us originally on Season 8 to talk about her branding and design business. Since we last talked, Margaret has had some luck on collaborating with other creatives, but is still stru ....

S10 E4 — 12 Mo. of Revenue in 30 Days

On today’s show, it’s just Preston and Clay. That’s because in early January, Preston asked Clay how things were looking for the new year and his response was something like: "I’ve already hit my 6 month revenue goal." Yeah, it was January 7th. NUTS! A couple weeks later—Before January was ....

S10 E3 — Less Convincing, More Closing.

On today’s episode we have a coaching call with Shelley, who works in the music industry—which can be a tough gig right now, but Shelley is making it work. There’s just a small problem with her principal business—booking artists into venues. Getting clients to understand the value Shelley br ....

S10 E2 — Are You Stuck in "Create" Mode?

On today’s show, we have a chat with Erica who, frankly, intimidates both Clay and me. That’s because Erica is working with some of the brightest people in the world to solve some of the biggest problems faced by humanity. But despite working with some incredible clients and solving some meaning ....

S10 E1 — 3 Ways to "Spy" on Your Ideal Client

3 Ways to Spy on Your Target Audience  On today’s episode, we have a coaching call with Nikolai—a freelance Webflow developer living and working in New Zealand. Nikolai’s entire freelance business completely turned around when he decided to focus exclusively on Webflow, showcasing the power o ....

S9 E14 — Leader vs. Entrepreneur

On today’s episode, we have a great coaching call with Andrea, who’s growing her agency—helping companies get the most out of the popular marketing software, Hubspot.  Andrea has hired contractors to help grow her business in the past and just a month before this conversation, Andrea hired he ....

S9 E13 — Are You Optimizing for Profit?

On today’s episode, we chat with Yusef who’s building his own small product design agency. Yusef’s got a lot going for him: he’s got great cashflow, he’s getting new clients regularly, and he enjoys the work he’s doing. But when it comes to the most profitable projects in his business, h ....

S9 E12 — Getting Out of Your Own Way

In today’s episode, we chat with an up-and-coming agency-builder, Maddie. And during our conversation we come up against one of the most common issues hold many of us back: Getting out of our own way. The thing is, Maddie is extremely bright. She’s got a lot of great things going. And she’s go ....

S E — Will Clients “Subscribe” to Freelancing?

On today’s episode we mix it up a bit with Craig Solid—a consultant in the healthcare space. Craig’s business is going well and he’s trying to figure out how to better serve his clients on an ongoing basis and potential find some subscription revenue as well. What we uncover is a potential m ....

S9 E11 — Make Art, Make Money

On today’s show I (Preston) have a really great conversation with James O-Reilly, an indie artist who’s working on making the transition from freelancer to founder. James has had heaps of work come in over the last year which is good because he's making good money as an artist, but he’s not ex ....

S9 E10 — Working From Anywhere (Remote Works Podcast Sneak Peek)

To listen to more episodes or subscribe to Remote Works, click here. On today's bonus episode, I share with you a fun podcast called 'Remote Work' from the team at Citrix. You know how, before Covid, only a relative few of us knew how great it was to work from anywhere? Well, Remote Works is on a mi ....

S9 E7 — The Truth About Being a ‘Founder’

On today’s episode, we chat with Chase, a co-founder at Electric Eye. They help Direct-to-Consumer Shopify brands make more money. Like Clay and me, Chase started out as a freelancer, but over the last five years he and his business partner have grown their agency to eight employees. In this conve ....

S9 E6 — Giving Yourself a $40K Raise + Investing in People

On this week’s episode, we check back in with one of our favorite guests from last season: Amy Kuo. Amy’s business is growing well and she even hired her first intern this year. But she still has a lot of questions about hiring and outsourcing. And since Clay and I believe whole-heartedly that p ....

S9 E5 — Attracting the Best Projects

You'll be happier and wealthier if you can learn how to attract the right kinds of freelance jobs in your career. On today’s episode, I’m joined by a special guest coach, my friend Matt Olpinski, as we offer some coaching to Wyatt Hill.  Wyatt’s got a really unique situation: his boss allows  ....

S9 E4 — 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 ....

S9 E3 — The Power of Automation

On today’s episode, Preston has a one-on-one conversation with James Rose. James is a total rockstar when it comes to automating tasks in your business. In fact, as you’ll hear by the end of this conversation, in order to accomplish everything James automates in his business, he’d have to hire ....

S9 E2 — Control Freaks Can Scale Too...Here's How

On today’s show, we have a really great conversation with Natalie, who has built a nice freelance design business but has also encountered some serious trouble when it comes to hiring. And even though Clay and I both know how critical hiring can be to your scaling success, we can also empathize wi ....

S9 E1 — Crushing Your To-Do List

On today’s episode, we have a coaching call with Ignacio, who’s building a growing web design business in Guatemala. Ignacio’s business is doing well, but he knows if he wants to go from freelance to founder, he needs to get more organized.  So in today’s call, we coach Ignacio through how  ....

S8 E17 — How I Finally Became My Own Boss

On today’s episode (the final episode in our eighth season) I want to turn the tables and share with you an interview I did with my friends Marc and Julia at The Clearing. I’ve done dozens of interviews over the years, but Marc seems to ask the perfect questions in this interview—leading to on ....

S8 E16 — Should You Ever Turn Down a New Client?

Do you ever get the feeling you're attracting the wrong kinds of clients for your freelance business or agency? Today's guest faces the same question: "how can I turn down clients who aren't a good fit?" Paul Chris Luke spent his first few years out of college working at an agency doing digital mark ....

S E — I Caught Covid-19 and Lost Half My Business. But Then....

Imagine catching the coronavirus and losing half of your clients in less than 48 hours. That's what happened to today's guest, Jim Huffman. Jim runs GrowthHit, a conversion-focused agency serving tech companies and startups. When Covid-19 hit the U.S. in March of this year, Jim got an email from one ....

S8 E14 — Getting Clients via Affiliates, Social Media, or Email

On today’s show, we talk with Akshat Choudhary who runs a thriving business called BlogVault. Despite having over 10,000 customers and a growing team, Akshat’s not sure where to go next when it comes to getting more customers. That all-to-common problem leads us to a conversation on building an  ....

S8 E13 — How to Scale When You Feel Too Busy

On today’s episode, we have a great conversation with Will Gibbons—a product rendering expert who works with huge brands like Pelaton, 3M, Vizio and more. After a year of working for himself, Will is facing perhaps one of the best problems you can ask for as a freelancer: He’s got too many cli ....

S8 E12 — Fixing Awkward Money Conversations w/ Clients

On this week’s episode we have a heart-to-heart chat with Bri Earles, a freelance social media manager and virtual assistant. Bri has never had any trouble getting new social media clients. But whenever Bri thinks about having money conversations or raising her prices, she kinda freezes up—using ....

S E — Cold Pitching vs. Content Marketing

On today’s call, we chat with Mihai Zamfir who has done some incredible work in building a presentation design company. Mihai gets a fair amount of new clients using sites like Upwork and other freelance marketplaces, but he’s ready to start finding better clients in more intentional ways. All o ....

S8 E10 — You're a Bottleneck—and it's Killing Your Business

On this week’s episode, we talk with Jason Vance, a former web design freelancer who’s building his next company in marketing. In just 9 months, Jason has hired 9 employees for his marketing agency because there's a whole lot of work that needs to get done. But now Jason feels like he may be hol ....

S8 E9 — An Audience is Not a Business

On this week’s episode, Clay and Preston have a heart-to-heart chat with Rodney Little, a UX/UI designer who wants to build an audience-first business. But Rodney, a side-hustler with a full-time job, has been kicking this idea around in his mind for a whopping five years—so in this episode, Cla ....

S8 E8 — Do I Really Have to Be the CEO?

On today’s show, we talk with Spencer Blaiklok—a freelance animator who dreams of building something bigger. But, like most creatives, Spencer doesn’t want to give up the fun creative work in order to sit behind a desk or in meetings all day, hating his job. In this episode, Clay and I walk Sp ....

S8 E7 — 5 Triggers to Raise Your Rates

In today’s episode, Clay and I talk all about freelance pricing: what to charge, and when to raise your rates. We explore two very different pricing models and reveal 5 triggers you should watch for to signal it’s time to raise your rates. If you’ve ever wondered if you’re leaving money on t ....

S8 E6 — Is Upwork Legit? + What You're Losing by Not Hiring

On today’s show, we have a nice long chat with Carl Smith. He’s been an in-house web developer for the past 20 years, but at the end of 2018, Carl finally launched a small business of his own—L&L Web Consulting. Carl saw some early success on Upwork, but when one client who was taking up 50 ho ....

S8 E5 — Why You're Failing at "Finding a Niche"

On today’s episode, we sit down with Margaret Ryland, a brand and identity designer who started her own design business not very long ago. Margaret is working hard trying to figure out exactly what kind of client to target which has left her listening to and reading a lot of advice about finding y ....

S8 E4 — Building a Business vs. Creating Another Job

Too many freelancers never actually build a business that works for them. Instead, they just build another job for themselves—trading one annoying boss for a dozen high-maintenance clients. Eesh. In today's episode, we sit down with Bobby Macey, founder of Macey Media. After side-hustling through  ....

S8 E3 — Is Social Media Worth Your Time?

Auni Milne can close a deal with just about any client that comes her way. But getting new clients continues to be a struggle. Can being more active on social media help Auni improve her inbound lead generation? We explore that question on today's episode of Freelance to Founder. Leave us a review o ....

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