Episode 38: How to Learn Freelancing with Matthew Dowling

Episode 38: How to Learn Freelancing with Matthew Dowling

Author: Sarah Duran January 30, 2025 Duration: 39:36

Matt Dowling is the founder of Freelancer Club, a platform born from his personal battle with an unpaid invoice that gained national attention. Freelancer Club equips over 72,000 freelancers with the tools, skills, and connections to thrive professionally.

In this episode, Matt shares the evolution of Freelancer Club from a Facebook support group to a comprehensive platform that combines education, community, and policy advocacy.

His journey shows how personal setbacks can fuel systemic change. His campaigns, including #NOFREEWORK and ‘Rise, Freelancer,’ have championed fair pay, diversity, and inclusion, aiming to support 1 million freelancers by 2026.

Our conversation also explores the changing landscape of freelance work, particularly how younger generations view independent work as less risky than traditional employment. We discuss Freelancer Club's innovative approach to education, teaching business skills by tapping into people's natural entrepreneurial instincts, and their work on policy reform to create better protections for independent workers.

Whether you're an aspiring freelancer, an educator interested in preparing students for the future of work, or someone passionate about freelancer rights, Matt's insights into building a more equitable and supportive freelance ecosystem offer valuable perspective on where independent work is headed.

Learn more about Matt and Freelancer Club on LinkedIn, his website, Spotify, or Apple Podcasts.

For more content and live events go to www.fruitioninitiatives.com.


Hosted by Sarah Duran, The Future is Freelance moves beyond the typical success story narrative to tackle the real, often unspoken, challenges of independent work. This podcast operates on a core belief: the most practical and resilient solutions are forged by the people living this reality every day. Each episode convenes voices from across the entire freelance ecosystem-from solo creators and agency owners to platform developers and policy advocates. The goal is to break down the silos and echo chambers that often isolate us, creating a rare space for genuine dialogue. You’ll hear frank discussions about pricing, client relationships, systemic inequities, mental health, and the philosophical shifts redefining modern work. Rather than offering one-size-fits-all advice, these conversations leverage collective wisdom to explore actionable paths forward. Tuning in means joining a grounded community effort to not just navigate the present landscape, but to actively shape what comes next. It’s for anyone curious about the human and structural dynamics behind the growing freelance economy, seeking both solidarity and substantive strategy.
Author: Language: English Episodes: 72

The Future is Freelance
Podcast Episodes
Episode 29: The Power of Community with Yurii Lazaruk [not-audio_url] [/not-audio_url]

Duration: 30:53
Yurii is on a mission to build connections among freelancers and bring greater visibility to the joys and sorrows that we all deal with. We had a great conversation about the power of community, defining work for ourselv…
Episode 28: The Relationship Business with Reuben Swartz [not-audio_url] [/not-audio_url]

Duration: 39:09
Reuben created the “anti-CRM” for freelancers and consultants based on his own experience building a solopreneur business. His platform is based on key values that successful freelancers share, including valuing relation…
Episode 27: Elevating Freelancing with Úna Herlihy & Peter McPartlin [not-audio_url] [/not-audio_url]

Duration: 39:13
Úna and Peter are some of my most favorite people and this conversation was one of the best so far. They started their freelance ecosystem in Ireland in response to the need for support during the pandemic and it has gro…
Episode 26: Financial Planning for Solopreneurs with Ryan Page [not-audio_url] [/not-audio_url]

Duration: 21:24
I had a great time talking with Ryan about all things soloprenuer finances. Ryan is a solopreneur finance expert who is committed to helping business owners understand their numbers and feel in control of their money. He…
Episode 25: How To Get Started as a Freelancer with David Kaplan [not-audio_url] [/not-audio_url]

Duration: 30:32
David Kaplan might be a new-ish freelancer, but he already knows the key to success - you just have to try! I had such a great conversation with David talking about learning by doing, mindset shifts, and the rewards of p…
Episode 24: Aces on Tap with Chrissy and Jim [not-audio_url] [/not-audio_url]

Duration: 26:48
When you bootstrap a micro-consulting platform as a side-hustle, you are for sure a hustler. Chrissy and Jim not only have created an awesome platform for people to share and monetize their unique talents, they’ve done i…
Episode 23: The Four-Day Workweek with Joe Sanok [not-audio_url] [/not-audio_url]

Duration: 38:32
In this episode of The Hustlers Manifesto podcast, I interview Joe Sanok, a father, entrepreneur, and author of the book "Thursday is the New Friday". Joe shares his journey of starting his counseling private practice in…
Episode 22: The Myth of Competition with Adam Faulkner [not-audio_url] [/not-audio_url]

Duration: 45:11
In this episode of The Hustlers Manifesto podcast, I interview Adam Faulkner, a proud freelance business owner and creator of the "Be FreelanceAF" course. Adam shares his journey of founding his freelance video productio…
Episode 21: A Hyper Curated Freelance Ecosystem with Karina Rehavia [not-audio_url] [/not-audio_url]

Duration: 36:24
Karina Rehavia isn't building "just" another freelance marketplace; she's building an ecosystem for freelancers and their clients that focuses on an amazing experience on both sides of the equation. Plus, she's one of th…