Freelance to Founder

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 operation, revealing why volume of work alone isn't the right reason to hire, and how choosing between "deliverable hires" and "business hires" can determine whether you build real freedom or just create another job for yourself. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Learn more about guest co-host, Christine → https://www.linkedin.com/in/colivas/ — https://nosingleindividual.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 need to be good enough to solve your clients' problems. Learn how to reframe expertise, overcome self-doubt, and start building your freelance business with confidence. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices

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, or strike out on his own? Preston shares practical strategies for testing your market, setting boundaries, and transitioning from subcontractor to independent consultant without burning valuable bridges. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices

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 break down exactly how to de-risk those make-or-break moments when you're ready to level up from solo freelancer to agency owner. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → ⁠⁠https://www.freelancecake.com/community⁠⁠ Get Austin's Book, Free Money → ⁠⁠https://austin-l-church.kit.com/cf0feb3e27⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 the surprising ways that being "foreign" can actually make you more attractive to American clients. If you've ever doubted whether distance or cultural barriers are limiting your freelance potential, this episode will shift your entire perspective. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → ⁠⁠https://www.freelancecake.com/community⁠⁠ Get Austin's Book, Free Money → ⁠⁠https://austin-l-church.kit.com/cf0feb3e27⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 smart delegation strategies. Austin shares real insights from his 4+ year relationship with his VA, including why he prioritizes character over skills and his brilliant low-stakes/high-frequency framework for deciding what to delegate first. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → ⁠https://www.freelancecake.com/community⁠ Get Austin's Book, Free Money → ⁠https://austin-l-church.kit.com/cf0feb3e27⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 good freelancers, and why charging higher prices can actually earn you more respect. If you're planning to transition from freelancer to agency owner, this conversation will shift how you think about value, pricing strategy, and positioning yourself as an authority. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → ⁠https://www.freelancecake.com/community⁠ Get Austin's Book, Free Money → ⁠https://austin-l-church.kit.com/cf0feb3e27⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 through visual content and strategic partnerships. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → https://www.freelancecake.com/community Get Austin's Book, Free Money → https://austin-l-church.kit.com/cf0feb3e27 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 deliver on time? Can she overcome that somehow? We tackle that question and lots more on today’s episode of Freelance to Founder. This episode was originally aired on January 11, 2024. PS: Get featured in an upcoming Q&A! Just visit ⁠http://freelancetofounder.com/ask⁠ and submit a question.  Support our Sponsors Our generous sponsors make this show 100% free to you. Support them at the link below. ⁠https://freelancetofounder.com/sponsors⁠ Get your own on-air coaching call We'd love to feature your business and offer some free on-air advice for growing your business. To see if you're a good fit, ⁠click here⁠. 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 review on Apple Podcasts? We'll love you forever. ⁠Click here to leave a review⁠. More Recommended Listening: This show is a part of the Podglomerate, a company that produces, distributes, and monetizes podcasts. We encourage you to visit the ⁠website⁠ and sign up for our newsletter. We suggest you also try other Podglomerate shows about entrepreneurship, business, and creativity, such as ⁠Rocketship.fm⁠ and ⁠Creative Elements⁠. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 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% free to you. Support them at the link below. ⁠https://freelancetofounder.com/sponsors Learn more about your ad choices. Visit megaphone.fm/adchoices