This Mistake Cost Me $30,000

This Mistake Cost Me $30,000

Author: Millo February 23, 2026 Duration: 18:49
Lena is a new freelancer staring down one of the most universally dreaded moments in self-employment: tax season. She knows taxes are confusing, but she's not sure whether to invest in an accountant from the start or try to handle it herself. Preston and Austin Church—both of whom learned the hard way—share what they wish someone had told them earlier, including the costly mistake that set Preston back $20,000 to $30,000, and the simple mindset shift that makes all the difference. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

There’s a common gap between working for yourself and truly building something that lasts, and Freelance to Founder lives in that space. This isn’t just theory; it’s a daily conversation for freelancers who are tired of the unpredictable income and ready to create a real business. Host Preston Lee draws from his own journey from freelancer to someone who has built and sold companies, and he brings that grounded perspective to every episode. Nearly every weekday, Preston is joined by other founders and entrepreneurs who’ve navigated the same path, breaking down the practical steps you can take to scale your solo operation. The call-in format means you’re hearing real questions from people in the trenches, facing the same client issues, pricing dilemmas, and growth plateaus you might be. Listening to this podcast feels like having a direct line to a supportive and experienced mastermind group, one that focuses on actionable strategies over vague inspiration. It’s for the designer, writer, developer, or consultant who’s ready to move beyond the feast-or-famine cycle and lay the foundation for something more substantial and sustainable. The discussions are candid, the advice is tested, and the goal is always clear: helping you transition from a solo practitioner to the founder of a thriving business.
Author: Language: English Episodes: 100

Freelance to Founder
Podcast Episodes
5 Places to Get More Leads and Attention [not-audio_url] [/not-audio_url]

Duration: 20:09
Struggling to grow your freelance business and attract quality clients? In this episode of Freelance to Founder, Dr. Noah St. John breaks down his proven MAPSSS method for generating leads that can transform your busines…
These Habits May Be Holding You Back [not-audio_url] [/not-audio_url]

Duration: 24:22
Breaking free from self-imposed limitations isn't just about willpower—it's about understanding the deep-rooted habits that keep you stuck. In this eye-opening episode, Dr. Noah St. John reveals the psychological mechani…
How Long Does It Take to Succeed? [not-audio_url] [/not-audio_url]

Duration: 19:53
Freelancing promises freedom, but the path to steady income can feel uncertain. In this episode, Preston and Meredith dive deep into the strategies that help freelancers build a reliable revenue stream, sharing practical…
What We Wish We Knew Before Jumping In [not-audio_url] [/not-audio_url]

Duration: 17:48
Embarking on a freelance journey can feel like navigating uncharted waters. Many aspiring freelancers get stuck in the preparation phase, overthinking branding, websites, and perfect portfolios instead of taking the most…
Our Biggest Lessons Learned as Freelancers [not-audio_url] [/not-audio_url]

Duration: 17:48
Freelancing isn't just about the work you do—it's about understanding yourself, managing your time, and staying flexible. In this episode, Preston Lee and Meredith Cooley dive deep into the most valuable lessons they've…
Balancing Self-Employment Dream with Full-Time Job [not-audio_url] [/not-audio_url]

Duration: 21:29
Dreaming of launching a freelance business while working full-time can feel overwhelming. What if you could strategically carve out time, optimize your schedule, and build momentum without burning out? In this episode, f…
How We Got Our Very First Clients [not-audio_url] [/not-audio_url]

Duration: 11:43
Breaking into freelancing can feel like an impossible challenge when you're just starting out. But what if landing your first client is simpler than you think? In this episode, Preston and AJ Cassata dive deep into pract…
Buying Back Your Time as a Freelancer [not-audio_url] [/not-audio_url]

Duration: 16:36
Freelancing offers freedom, but it can also lead to working more hours than ever before. In this episode of Freelance to Founder, Preston and AJ dive deep into a listener's struggle with time management, offering practic…
Why You're (Still) in the Feast-Famine Stage [not-audio_url] [/not-audio_url]

Duration: 18:46
Freelancing can feel like riding a rollercoaster of unpredictability. One moment you're scrambling for leads, the next you're buried under a mountain of projects. In this episode, Preston and AJ dive deep into practical…
Stuck with Low-Paying Clients? Here's the Fix... [not-audio_url] [/not-audio_url]

Duration: 21:48
Preston and AJ dive deep into strategies that will help you break free from the local client trap and attract high-value, premium international clients. Learn proven tactics for transforming your outreach, positioning yo…