Ep 128 Career: How to start your studio or freelance business

Show notes

What’s going on, everybody? And welcome into the 128th episode of The Crazy One podcast. As always, I’m your host, Stephen Gates, and this is the show where we talk about creativity, leadership, design, and everything else that helps empower creative people.

Remember, you can listen to the show, get the show notes, and a whole lot more at thecrazy1.com. That’s always the words “the crazy” and the number “1”.com. And while you’re on your favorite podcast platform, hit the subscribe button to get the latest episodes when they come out. Leave a review if you can—it helps other people find the show and helps me feel like this is all worth the time.

For those of you listening in real time, hello again. It’s been quite a while since I’ve done that intro, and it feels a bit strange. Not much has changed out there—layoffs are still rampant, the hiring process is broken, and companies are tightening budgets. It’s been eight or nine months since the last episode. If you follow me on social media or listened to previous shows, you know I started my own strategy and design studio. Honestly, that move was long overdue. I’m having a ton of fun, working with amazing clients, and doing work I’m incredibly proud of.

This is also the first time I’ve recorded since leaving New York City. I moved back to Pittsburgh, my hometown, at the end of December to build our dream home. Same setup, new studio and view, same cast of characters: Ogie under the desk and Crosby asleep nearby. The more things change, the more they stay the same.

When I sat down to write this episode, like I always do, I started by researching. Since starting my studio, people have asked how I did it, if I like it, or what they should consider if they’re thinking about doing the same. With the job market in chaos, I looked for advice online. And I found a ton of “7 easy steps to start your studio” or “12 things to do as a freelancer” articles. But here’s the thing: most of that advice focuses on your logo, marketing, or website platform. While those are important, they aren’t the foundation you need to succeed.

In this episode, I want to focus on those foundational questions. What do you really need to figure out if you’re considering becoming a freelancer, consultant, or starting a studio or agency?

1. How long do you want to do this?

Is this just a stopgap while looking for your next job, or do you want this to be your future? For me, it started as temporary, but I ended up loving it. After I got laid off, I started consulting. Then clients offered retainers, and I saw a real opportunity.

2. What’s your tolerance for risk and uncertainty?

Do you need a steady paycheck? Can you handle the ups and downs of project work? I lean toward ongoing client relationships, which is why my model is retainer-based. It’s helped reduce volatility and build trust.

3. Are you doing this alone or with others?

I’m the only full-time employee in my studio. I work with others on a 1099 basis, which keeps overhead low and flexibility high. That approach helps with pricing and adaptability.

4. Remote, hybrid, or in-person?

We’re fully remote but travel for meetings and shoots. Our clients span multiple geographies, and we make it work.

5. What will you call it?

I didn’t go with “Stephen Gates Design” because I didn’t want to put myself above collaborators. I chose “CRZY,” a derivative of my personal brand and this podcast. Companies like working with companies.

6. What sets you apart?

There are plenty of studios out there. What’s your differentiator? For me, it was delivering big-agency-level results with creative agility. I sell time blocks instead of specific deliverables. That lets us solve whatever problem comes up—strategy, culture, team dynamics. Clients invest in me, and I invest in them.

7. What size clients do you want?

I prefer small-to-medium clients or focused teams within larger companies. Less bureaucracy, more creativity. We work with 3-4 clients at a time so we can build deep relationships and deliver real impact.

8. Don’t be generic.

Clients want to hire people with a point of view. Be specific. You don’t need to appeal to everyone—you just need 2-4 good clients.

Setting up the business

You need an accountant and a lawyer. An accountant will help you choose an entity (LLC or S-Corp), set up business accounts, manage taxes, and find deductions. A lawyer helps with contracts and reviewing what you’re signing. Don’t skip this. It protects you legally and financially.

Pricing your work

Start with a salary goal. Let’s say it’s $150,000/year. Divide by 52 weeks = ~$2,885/week. Divide by 40 hours/week = ~$72/hour. That’s your minimum rate. Add overhead on top. Adjust based on your desired work schedule.

I use Gusto for payroll and manage my own 401(k) and health insurance. You can build these things over time.

Soft-launch your business

Don’t kick it off with a big LinkedIn post. Instead, start small. Test your name, pitch, and pricing with people you trust. Get early feedback. Then make the public announcement. That approach worked well for me.

Keep evolving

Not everything will work. Let go of what doesn’t. Stay curious. Be uncomfortable. I now work on AR installations, documentaries, and restaurants—things I never imagined. It’s exciting.

One final thought

Sylvia Baffour once told me: “Discomfort is the cost of fulfillment.” That helped me push through fear. I had massive imposter syndrome and questioned if I could do this. But at the end of the day, I realized I was afraid to bet on myself.

You have to believe in your talent. Believe in your ability to figure it out. It’s not easy, but it’s worth it.

Tagged as:
building a studio business clarity career career transition consulting advice creative independence creative industry insights entrepreneurship freelance roadmap freelancing tips going solo navigating layoffs starting a business tephen Gates