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
Superhero Leadership [not-audio_url] [/not-audio_url]

Duration: 46:18
Sharing an episode of the Superhero Leadership podcast, hosted by Marvel's former CEO and legendary turnaround expert, Peter Cuneo. Each week, Peter is joined by top performers from business, media, and beyond, leaders w…
[Q&A] Charge by Hour or Project? [not-audio_url] [/not-audio_url]

Duration: 19:35
On today’s Q&A episode, if a client is willing to pay by the hour or by the project, which one should you choose? That’s part of Pennygoo’s question, and our answer might surprise you… Here we go! This episode was origin…
Can You Ever Step Away? [not-audio_url] [/not-audio_url]

Duration: 48:47
On today’s show: Can you ever step away from your business? Or are you doomed as an entrepreneur to never enjoy a vacation or time off ever again? That’s just part of what we talk about with our guest Jim, who’s calling…
[Q&A] Client-Converting Portfolio Tips [not-audio_url] [/not-audio_url]

Duration: 18:22
In this Q&A episode, Oliver asks us what it takes to create a portfolio that actually brings in new long-term clients. And since Clay and I are real marketing geeks, we have quite a few ideas for turning your sleepy port…
Too Busy to Grow? [not-audio_url] [/not-audio_url]

Duration: 58:04
On today’s show: Do you ever feel like you’re just way too busy to actually spend time growing your business? If so, you’re not alone. We chatted with Will Gibbons, who works with cool clients like Peloton, 3M, and Vizio…
[Q&A] Should I hire a CPA or use a tax software? [not-audio_url] [/not-audio_url]

Duration: 14:07
Today’s question comes from our ⁠free Mastermind group⁠ on Facebook. Anna Keith asks: "I’m getting ready to do my taxes and am considering trying software rather than hiring a CPA. What insights or pros/cons about using…
Should I Even Try? [not-audio_url] [/not-audio_url]

Duration: 31:18
On today’s show: is it even worth trying to grow your freelance business? That’s where Rakesh finds himself. He gets most of his clients from freelancing platforms like Upwork. And the market for web designers and develo…
[Q&A] Can I Put In-House Work in My Portfolio? [not-audio_url] [/not-audio_url]

Duration: 11:21
This episode's question came in via email. Nico works as a designer for a company right now, and he wants to start freelancing on the side and build a business. He said, “I was thinking of creating a portfolio, including…
Is a VA a Good First Hire? [not-audio_url] [/not-audio_url]

Duration: 44:47
On today’s show: Is a VA a good first hire in your company? We’re joined by call-in guest Nils, who wants to know when and how to hire a VA—a virtual assistant. But Clay and I slam on the brakes and force Nils to answer…
[Q&A] Best Software for Getting Paid Faster? [not-audio_url] [/not-audio_url]

Duration: 10:07
Today’s question comes from our ⁠free Mastermind group⁠ on Facebook. Darielle asks: "What's the BEST Software for getting paid faster?" Getting paid for your work FAST is key, but how do you make it happen? You'll get th…