Entrepreneur: Austin L. Church

Biz: Freelance Cake

Tilt: Teaching freelancers how to be successful with less runway.

Primary Channels: Freelance Cake website, Austin L. Church website

Other Channels: X (2.1K), LinkedIn (11.7K), Instagram (16.5K), podcast

Time to First Dollar: 6 years (as a content entrepreneur); 2 months as a freelancer.

Rev Streams: Coaching, courses, fractional CMO positions, book 

Our Favorite Actionable Advice:

  • Have the courage to launch: Austin thought about doing a podcast for a while but always talked himself out of it. Last year, he decided to just do it, committing to one season a year. 
  • Get guest gigs: Work with other creators to gain access to their audiences. Secure guest spots on podcasts. Establish yourself as an expert and thought leader through other entrepreneurs’ platforms.
  • Find a negative mentor. Austin believes you need negative mentors in your space or closely adjacent. Someone you can look at and think, “That person isn’t working harder or smarter. If they can do it, surely I can do it too.” Evaluate what’s holding you back. More often than not, it’s a mindset, not a strategy. 

The Story of Austin Church

“I thought I was going to be a college English professor. I went to grad school to get a master’s degree in creative writing and literature. And then I found myself disenfranchised with academia. So now what?”

The “now what” began Austin Church’s entrepreneurial journey as a freelancer, consultant, and coach. The “now what” led to him securing a job at a marketing agency, where he fell in love with business and had a mini-identity crisis. He had wanted to write books, and now, in 2008, his newfound fascination with entrepreneurship and business strategy confused him.

Unfortunately, 2008 was also when a recession reared its ugly head. On a Friday in April 2009, Austin was laid off. He awoke the next Monday scared. “I remember being terrified because I only had $486 in the bank. I will never forget that number. I thought I was so stupid. Why didn’t I save more money,” he recounts to The Tilt.

A layoff prompted @AustinLChurch (who had $486 in the bank) to freelance and eventually become a #ContentEntrepreneur. Click To Tweet

Though he appreciated the gravity of the situation, Austin also had an unexplained sense of levity. Looking back, he says he felt that lighter feeling because his path to entrepreneurship had been decided for him.

In May 2009, Austin began his journey as a freelance writer and unknowingly started his path to becoming a content entrepreneur.

Austin learned as early as middle school that he had a knack for examining a situation and assessing how to get better results with less effort. So when, early in his career, an agency owner taught him about the golden suitcase, Austin eagerly embraced it. He collected different business principles along his professional journey and examined how each applies to his business practice. 

Developing first content products 

In 2011, Austin found himself not only writing but working on product development. He developed Mustache Bash, an app with mustache options that the user could select to superimpose on a digital image.

For four years, Austin developed over 30 apps. He discovered he could make more money licensing the source code through tutorials than selling the apps. He likens it to selling a shovel to gold prospectors.

In April 2015, Austin sold his app business portfolio and founded Closeup.fm – software for ticketing, touring, and communicating by independent bands. Its life cycle ended in 2017.

‘Now-what’ entrepreneur itch remains

In early 2018, Austin found himself in a weird position. After multiple profitable years, he now had no current project but still had an entrepreneurial itch to scratch. He did what a lot of successful founders do – consult and coach.

Austin onboarded his first coaching client at the end of 2018 and went full-time into consulting and coaching. Around the same time, he organized some ideas from his “golden suitcase” into several mental models and frameworks. 

He built a good framework for helping freelancers and consultants make more money with less effort. Austin designed his frameworks into actionable, shareable advantages, like cheat codes for video games.

Achieving content entrepreneur realization

Interestingly, Austin did not consider himself a true content entrepreneur until 2019. Up until this point, he was a freelancer and a consultant and believed he was only being paid for his skills. He had not truly monetized his audience. 

So in late 2019, Austin, who had been thinking about course creation for a while, stopped psyching himself out of doing it and launched his first class. He considers that revenue his first as a content entrepreneur. 

“Of course, I did it the wrong way, and it took me 250-plus hours to create. But I finally launched it in early December of 2019. And I think 10 or 20 people bought it. I was disappointed, but I had to remember some people bought it. It was not a viable, sustainable business model, but someone bought it,” he explains.

Only 10 or 20 people bought the first course from @AustinLChurch, who spent 250+ hours developing it. Though it wasn't a sustainable business model, at least someone bought it. #ContentEntrepreneur Click To Tweet

That first course – Freelance Cake – morphed into Austin’s brand for coaching and courses. Within a year, he launched a cohort-based course and later added a weekly newsletter.

Coaching quickly became the main service of Freelance Cake with three levels – one-off clarity sessions, custom business roadmap engagement, and a group mastermind based on his 300K flywheel concepts. 

His high-ticket engagements and Morning Marketing Habit course bring in the biggest revenue.

Austin credits writing daily on LinkedIn with generating new clients and traffic for his website. He also appears as a guest on as many podcasts as he can, using those expert creators’ audiences to gain new coaching clients.

“My guest episodes on other people’s podcasts have been very effective because people spend an hour listening to you unpack what, for them, is a complex issue. And if you can make people laugh while popping all the objections like balloons, then people are going to say, ‘Yeah, I like that guy’s style, and I’m going to check him out.”

Entrepreneur @AustinLChurch generates traffic to his #FreelanceCake website by posting daily on LinkedIn and appearing as a guest on podcasts. #ContentBusiness Click To Tweet

Last year, Austin created The Freelance Cake Podcast. He publishes one season a year as he does not have the bandwidth to do it weekly. He is working on season two.

Austin is working on his first business book, Free Money with Tilt Publishing. He also is working on revamping his business model between his namesake and Freelance Cake brands. The Austin L. Church brand will focus on his thought leadership and his fractional CMO engagements. His content and coaching offers will continue under the Freelance Cake brand. 

Advice for content entrepreneurs

Among Austin’s advice for fellow content entrepreneurs:

  • Don’t apologize for selling services to pay the bills. It takes a long time to build a loyal audience. Don’t sell yourself short and say, “I’m not full-time yet,” or “I’m a freelance web designer until I go full time.” 
  • Find a negative mentor. Many entrepreneurs credit their growth to the influence and guidance of a positive mentor. However, Austin believes you need negative mentors in your space or closely adjacent. Someone you can look at and think, “That person isn’t working harder or smarter. If they can do it, surely I can do it too.” Then, evaluate what’s holding you back. More often than not, it’s a mindset, not a strategy. 
  • Don’t “work harder.” Instead of working harder and risking burnout, tweak your technique to work smarter. For example, market your consulting clients toward higher ticket offers. You can make more money with fewer clients and devote more time to the content side of your business.
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About the author

Marc Maxhimer is the director of growth and partnerships at The Tilt. He holds a bachelor’s degree in English and mathematics education and a master’s degree in educational administration.  He previously taught middle school for 16 years.  Marc lives in (and loves all things) Cleveland with his wife, two daughters, and dog.