Good Idea? Freelancing as a Family...

Good Idea? Freelancing as a Family...

Author: Millo June 5, 2025 Duration: 55:25
Is freelancing as a family a good idea? Can it actually work? That’s part of what we get into with our call-in guest, Dave. Dave is the father of 3 talented young developers. Together, they’ve started an agency. Well… sort of. As we talked with Dave, we uncovered this: family dynamics are not the same as business dynamics. And sometimes, managing both can present a real challenge.  If you’ve ever wondered whether or not to go into business with family, today’s episode of Freelance to Founder is for you. Here we go! This episode was originally aired on September 21, 2023. 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

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
Am I Too Shy to Network? [not-audio_url] [/not-audio_url]

Duration: 21:45
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 connection…
There Must Be a Better Way [not-audio_url] [/not-audio_url]

Duration: 23:37
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 e…
Please Don't Kill My Baby... [not-audio_url] [/not-audio_url]

Duration: 21:46
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…
Am I Ripping Off My Freelancers? [not-audio_url] [/not-audio_url]

Duration: 23:52
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,…
Is Now the Right Time For This? [not-audio_url] [/not-audio_url]

Duration: 21:06
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 big…
What if I'm not 'Expert Enough'? [not-audio_url] [/not-audio_url]

Duration: 14:31
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. CodeCraft…
Getting Swallowed Up [not-audio_url] [/not-audio_url]

Duration: 13:14
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…
Should I Say "Yes" to This? [not-audio_url] [/not-audio_url]

Duration: 19:00
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…
Will American Clients Even Hire Me? [not-audio_url] [/not-audio_url]

Duration: 18:10
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 t…
What to Look for in a VA [not-audio_url] [/not-audio_url]

Duration: 20:41
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…