Podcast Summary: The Code To Winning

Episode 072: Why More People Are Choosing Freelancing: How To Start Today

Guest: Jamie Brindle
Host: Kagiso Dikane
Date: December 19, 2025

Episode Overview

This episode centers on the meteoric rise of freelancing, discussing why it’s attracting more people globally, how to get started, upscale, and thrive in the field. Jamie Brindle—successful freelancer, entrepreneur, and educator—dives into his own journey, the mental shifts needed for sustained growth, practical strategies for new and experienced freelancers alike, and future trends in the freelance ecosystem.

Key Discussion Points & Insights

1. The Freelancing Boom ([00:00], [05:00])

• Freelancing's Growth: By 2027, the majority of the American workforce is projected to be freelance. This shift is global—freelancing is redefining work everywhere.
  • Quote: “We’re changing the shape of what work looks like worldwide.” — Jamie Brindle [00:06]
• Pandemic as Catalyst: COVID-19 exponentially increased interest in freelancing as people sought flexible, remote income streams.

2. Jamie's Freelancing Origin Story ([00:21], [05:46])

• Began freelancing in high school (2007), producing local TV commercials door-to-door.
• Built a production studio with his wife, scaling to teams and diversifying revenue.
• COVID-19 led Jamie and his wife to pivot: instead of just selling digital products, they decided to teach others how to build freelance businesses.
  • Quote: “We sat in our second bedroom office and said, what if instead…we helped people that look like us build their business?” — Jamie Brindle [01:11]

3. Key Mindset Shifts: Surviving vs. Thriving ([01:33], [16:24])

• Solutions Over Skills: The biggest shift is realizing business is not about trading skills for money, but solving problems that matter to clients.
  • Quote: “Business is the exchange of money for solutions, not…the thing I do.” — Jamie [01:44], expanded [16:24]
• Shifting communication with clients from talking about technical details to focusing on desired business outcomes (conversion rates, audience engagement, etc.).
  • Quote: “I started being able to position myself…as a strategic partner.” [18:00]

4. Outsourcing & Global Competition ([09:29])

• Outsourcing is a tool—sometimes used to maximize budgets, sometimes for 24/7 operations.
• Local versus overseas freelancers depends on problem specifics (need for onsite work, time zones, or budget).
  • Quote: “The business lives or dies by how specific, how urgent and how painful the problem you solve is.” — Jamie [13:25]

5. The Power of Specificity and Niche ([13:25])

• There’s no “best” freelancing market—a freelancer succeeds by solving a unique, urgent, and painful problem for a particular audience.
• Having connections (family, friends) in a market can provide a leg up, but success comes from identifying and solving the right problem, not just broad skills.

6. AI and the Future-Proof Freelancer ([15:00])

• AI is rapidly transforming what a freelancer can achieve—multiplying output and leveling the playing field.
• Early adopters have a temporary advantage.
  • Quote: “You can yield the results of a team of 10 or 20 as an individual. Right now, that’s still a competitive advantage.” — Jamie [15:28]

7. Overcoming Undercharging & Imposter Syndrome ([19:20])

• Most freelancers undervalue their work.
  • Quote: “If you are a freelancer watching this, you’re undercharging.” — Jamie [19:49]
• Pricing should reflect the value and urgency of the problem solved, not just time or deliverables.
• Higher pricing often attracts better clients and communicates value.

8. Moving Beyond the “Referral Plateau” ([27:53])

• Many freelancers plateau when their business relies solely on referrals—they outgrow their networks.
• To break through, they must embrace social media, paid advertising, partnerships, digital products, and higher-leverage activities.
  • Quote: “Your network has done all it can do or ever will do for you…it's time to start doing some different things.” — Jamie [28:06]

9. Agency & Limitations in Freelancing ([30:28])

• Freelancing is “choose your own adventure.”
• Some accept their income plateau, but Jamie challenges the view that being a solo operator imposes a ceiling.
  • Quote: “The first solopreneur billionaire has been born.” — Jamie [31:10]

10. Three Pillars: Marketing, Sales, Fulfillment ([32:31])

• Fulfillment is most misunderstood—it’s not just “doing the thing,” but intentionally delighting clients and guiding their experience.
  • Nail the start and end of every project; over-deliver at key moments.
  • Turn clients into ambassadors and repeat customers.
  • Quote: “You knock fulfillment out of the park, your sales and marketing are pretty much handled.” — Jamie [35:15]

11. Biggest Failures & Lessons ([36:04])

• Dependence on a single large client nearly crippled Jamie’s business; raising rates and diversifying clientele was essential.
  • Quote: “I realized what needed to be done was…I needed to charge them substantially more so that I could hire help so that I could go run my business instead of being in their business.” — Jamie [38:44]
• Sometimes, standing firm on pricing means risking the client, but it’s often necessary for sustainable business growth.

12. Dealing with Lowballing Clients ([40:53])

• Best to negotiate scope, not price—offer a reduced deliverable but maintain rates.
• For must-have cashflow, limit concessions and avoid entering a “race to the bottom.”
  • Treat existing clients as long-term partners, advising them for mutual benefit.

13. The Future of Freelancing ([44:18])

• Jamie predicts a future where “everyone has an LLC” and works for themselves, forming temporary collectives for projects.
• Even C-suite roles are going fractional/freelance.
• Knowledge and tools are freely available; opportunity is abundant for those who pursue it.
  • Quote: “In the time it takes somebody to interview nine times for a job, they could have built a freelance business that made more income.” — Jamie [47:50]

14. Jamie’s Definition of Winning ([48:59])

• Agency: Winning means having the freedom to structure each day as you wish—agency over one’s own life and business.
  • Quote: “Being able to wake up in the morning and do whatever the hell it is you want to do. Agency.” — Jamie [48:59]

Notable Quotes & Memorable Moments

• “Freelancing has become ever so popular, especially from 2020 due to Covid.” — Kagiso [05:36]
• “Your clients are spending against the problem. It has very little to do with how much you cost and more to do with the certainty that you’re going to solve the problem for them.” — Jamie [21:00]
• “The cheaper option is not always the best. Matter of fact, sometimes it’s always the worst option.” — Kagiso [24:20]
• “We’re all selling one or more of three things: more money, more time, mitigated risk.” — Jamie [25:44]
• “There are millions of new businesses formed every year. A freelancer needs like nine of them to have a great career.” — Jamie [40:54]

Useful Timestamps for Key Segments

• Freelancing’s Rise & Global Shift: [00:00], [05:36]
• Jamie’s Start & Evolution: [00:21], [05:46], [07:10]
• Mental Shift (Skills vs. Solutions): [01:33], [16:24]
• Pricing & Imposter Syndrome: [19:20]
• Referral Plateau & Breaking Through: [27:53]
• Pillars of Freelancing Success: [32:31]
• Overdependence on One Client—Cautionary Tale: [36:04]
• The Future of Freelancing: [44:18]
• Definition of Winning: [48:59]

Jamie’s Contact Information

“Follow me on Instagram or LinkedIn and shoot me a DM there…let me know what you’re up against in maybe these next 12 weeks. I’d love to chat with you and strategize a little bit.” — Jamie [50:18]

Tone & Language

The conversation is direct, energetic, and supportive—Jamie combines lived expertise with encouragement, while Kagiso’s tone is friendly and curious. Real-world stories and practical how-to’s reinforce the learnings throughout.

Summary Takeaways

• Freelancing is entering a golden age—powered by technology, remote work normalization, and the democratization of business knowledge and tools.
• Success is rooted in solving urgent, valuable problems and communicating your value as a strategic partner, not just an executor.
• Scaling beyond plateau means embracing high-leverage strategies, digital products, and building an intentional client journey.
• Agency—personal and professional freedom—is the truest definition of “winning” in freelancing.
• Now is the best time to start and thrive as a freelancer; the only real limitations are mindset and willingness to experiment and adapt.