Freelance to Founder

Should you charge by the hour or by the project? If you've ever struggled with this question, you're not alone. But here's the truth: you might be asking the wrong question entirely. In this episode, Preston and Clay dive deep into pricing strategy with a question from Lanya, revealing why hourly pricing punishes you for being good at what you do—and introducing the game-changing concept of value-...

Feeling pressured to add marketing services to your web design business just because a course told you to? In this episode, Preston and Clay challenge the "supposed to" mentality that keeps freelancers stuck offering services they don't enjoy. Erica, a web designer, asks how to balance project work she loves with repetitive marketing tasks she wants to outsource—but the answer might surprise you....

Feeling paralyzed by the endless stream of marketing tactics you "should" be doing? You're not alone. In this episode, Matt from Barrow Studio asks the question every service business owner wrestles with: with so many marketing strategies out there—from email lists to podcasts to paid ads—where should you actually focus your limited time and resources? What's the "silver bullet"? Clay and Preston...

Feeling nervous about networking? You're not alone. In this episode, Brittany asks how to break into local networking as a shy person, and Clay shares exactly how he built a million-dollar agency through local connections—even as a total introvert. From joining your first chamber event to creative strategies that put you front and center without the awkward sales pitch, this episode is packed with...

As your freelance business grows from solo operator to team leader, the chaos can hit fast. Emma Clark's question about transitioning from inbox management to real systems is one every growing freelancer faces. In this episode, Preston and Christine Olivas dive deep into the practical side of scaling—revealing why your tool choice matters less than you think, and what actually needs to happen firs...

You've built incredible relationships with your clients as a freelancer—but now that you're growing into an agency, how do you transition them to work with your team without losing the trust you've worked so hard to earn? In this episode, Preston sits down with Christine Olivas, founder and CEO of No Single Individual, to tackle this exact challenge. Christine shares her insights on finding team m...

You've made your first couple of hires—congrats! But now comes the tricky part: how do you price your services high enough to pay your team well, while still remaining competitive enough to win clients? In this episode, Preston and Christine Olivas tackle the delicate balancing act of agency pricing, exploring the two-sided marketplace challenge of keeping both clients and team members happy. From...

You're swamped with client work, staying up late to meet deadlines, and turning down opportunities because you simply can't handle more. Sound familiar? In this episode, Preston and Christine Olivas tackle one of the biggest transitions in a freelancer's journey: knowing when—and how—to hire your first contractor. Christine shares her experience growing from solo freelancer to running a 24-person...

Feeling like you're not skilled enough to start freelancing or to grow your agency? You're not alone. In this episode, Preston tackles one of the biggest mental barriers new freelancers face: imposter syndrome. CodeCrafter asks how to build confidence when you don't feel expert enough—and Preston's answer might surprise you. Turns out, you don't need to be the world's best at what you do. You just...

When subcontracting becomes your main income source, it's easy to lose your business identity in someone else's brand—almost like you're getting swallowed up. In this solo episode, Preston tackles a question from Garrett, a 30-year-old nonprofit consultant who's concerned about being overshadowed by the seasoned consultant he subcontracts for. Should he merge his business, continue the partnership...

Every freelancer faces this dilemma: A dream client wants to hire you for a project that's bigger than anything you've tackled solo. Do you hire help first and risk the overhead, or do you say yes and scramble to build a team afterward? Preston and Austin dive deep into this classic chicken-and-egg problem, offering a surprising third option that could save your reputation and your sanity. They br...

Ever wondered if your location outside the US is holding you back from landing American clients? In this episode, Preston and Austin tackle a question from Dieter in Europe who's hesitant about offering his services to the US market. You'll discover how to flip perceived geographical disadvantages into powerful positioning strengths, why cultural differences might matter less than you think, and t...

Ready to hire your first virtual assistant but not sure where to start? Elena's question hits on something every growing freelancer faces: you have a million different tasks that need doing, but how do you find the right person to handle them all? In this episode, Preston teams up with Austin Church (founder of Freelance Cake Community) to break down the hiring process from character evaluation to...

Worried about raising your rates and losing clients? You're not alone. In this episode, Preston and Austin Church tackle one of the most common freelancer fears: how to increase pricing without damaging client relationships. But here's the twist—your clients might care about way more than just saving money. Austin shares eye-opening insights about client psychology, the hidden costs of replacing g...

Lana from Homewear Designs has cracked the code on getting home staging clients through real estate agent relationships in New York and the Hamptons. But she wants to grow faster. Should she double down on what's working or branch out into new channels? Preston and Austin dive into strategies for scaling your proven client acquisition methods while exploring smart ways to reach broader audiences t...

On today’s show, how can you possibly hire other freelancers to help grow your business when it’s hard to know if you can trust them? After all, if someone you hire misses a deadline, you’re on the hook with your client. That’s where Tina finds herself on today’s call.  She’s thinking about hiring and is willing to trust other freelancers' creative processes.  But what about their ability to deliv...

On today’s Q&A episode, A former guest on the show, Jim, writes in with an important question: I know I shouldn’t charge by the hour, but shouldn’t I pay my subcontractors by the hour? You might be able to guess our answer. Or it might just surprise you.  Let’s find out on today’s episode of Freelance to Founder. Here we go! This Q&A episode was originally aired on November 7th, 2023. To submit yo...

On today's show, we get called out by our call-in guest, Erik. Here's the thing: Clay and I are always talking about finding referral partners—other freelancers or businesses who can send you new clients as a sort of trade. You'll refer them to clients, and they'll refer you. It sounds magical. But Erik's question is this: how do you actually FIND these kinds of partners? So we get into it on toda...

I am joined by special guest co-host Austin Church on today's show. He is a very talented freelancer and the author of the new book, Free Money. It's all about growing your revenue as a freelancer, and we talked today about calculating your survival rate. That's the rate you need to stay in business as a freelancer. What's the minimum amount you need to make to stay in business? So, if you've wond...

On today’s show, ⁠Molly Cox⁠ calls in with questions about the freelance business she started just six months ago. Top of mind for her: Should she stay a sole–proprietor or form an LLC? Before the legal terms tempt you to click away, consider this. This single question could save you thousands of dollars a year in taxes. So keep listening. That’s just part of what we chat about with Molly. This ep...

On today’s Q&A episode, Luqman writes in with a question.  He’s a brand-new freelancer and wants to know exactly how to build a freelance network and attract more clients.  We all know your network can lead to massive growth for your business. So Clay and I break down what has worked well for us and what has totally bombed when it comes to networking.  If you want to build your network fast, you s...

On today’s show, how do you escape the trap of one-time projects and convince your clients that they need what you have to offer on a repeat basis? That’s part of the hurdle Aurelie faces as she aims to grow her 3-year-old freelance business.  Aurelie has worked with some huge clients like Wendy’s and the United Nations.  But almost all of her work has been on one-time projects.  Which naturally h...

On today’s show: how many people does it take to call yourself an agency officially? Is it one, two, or more than that? This question got us thinking about what it means to be an agency. Plus, we discuss our ideal team size and answer the question: How many are too many for your team? It’s all on this episode of Freelance to Founder. Here we go. This Q&A episode was originally aired on March 5, 20...

On today’s show: do you ever feel trapped by the decisions you make in your business? Our guest Morgan loves to write. But, early on, she took on quite a few social media clients. Then, those clients referred more clients. And suddenly, most of her client work is focused on social media marketing — not writing. So what do you do when your former choices have boxed you into a future you don’t neces...

On today’s Q&A episode, let’s talk about money. Exactly how much should you save before you can start your agency? We do our best to answer this question, and it got us wondering: What in the world are we spending all of our money on these days in our own businesses? So, as a bonus, we break down our finances a bit more to round out the episode.  It all starts right now on this episode of Freelanc...