Freelance to Founder

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 mismatch between the target client and product offering. All of us leads us into a much-needed conversation a...

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 exactly sure where to go next with his business. Should he hire more artists? Should he hire a project manag...

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 mission to highlight the new ways that millions of people are now working—from wherever they want. Rem...

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 conversation with Chase, we talk about all the things we three wish we had known about making the transitio...

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 people are the best possible investment you can make in your business, we have a lot to say on the subjec...

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 him to make connections with customers at his day job and then pitch them his side-hustle services. While t...

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 realizing it’s harder to transition from solo freelancer to full-on agency than she initially expected. C...

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 a full-time employee. Instead, he leverages affordable tech and brilliant workflows to save money and get...

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 with her feeling like too much of a control freak (her words, not ours) to make the best decision. So ho...

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 to organize his multiple brands, how to pick the perfect project management tool, and how to get his clients...

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 one of the best conversations on freelancing I’ve ever had on the air. We discuss getting freelance jobs, wh...

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 marketing. But then he decided to leave it all behind, sell his house and most of his possessions and mo...

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 of his clients asking to put their work “on hold”—which was all fine and well until another client...

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 affiliate program to get new clients, using social media to build a front-of-mind brand, and taking adva...

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 client requests coming in and too much work that needs done. So in this episode, Clay and I walk him through...

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 words like “awkward” “greedy” or “selfish” to explain how she feels about charging clients. What many f...

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 of this leads us to an answer-rich coaching session all about short-term vs. long-term sales strategies. ...

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 holding his team back by causing a bottleneck. It's hard going from doing everything yourself to hiring and...

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, Clay and Preston call him out. They dive into what’s been holding him up and what it’s really going to look...

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 Spencer through a few different ways he can grow his business without having to become a typical CEO-type. B...

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 the table in your business or if you’re charging the right amount for the work you do, this episode is for yo...

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 hours of his work-week suddenly halted their project, Carl was left wondering if sites like Upwork were the...

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 your freelance niche. Advice to "find your niche" in business is not uncommon on the Internet—you’ve pr...

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 a series of frustrating lay-offs, Bobby finally decided to take matters into his own hands and start a...

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 on Apple Podcasts: If you enjoy the show, can you do us a favor and leave us an honest rating and rev...