Jay Clouse is a freelancer-turned-creative entrepreneur who wears multiple hats.

He runs a community of entrepreneurs, a podcast (with over 2 million downloads), a newsletter (with 54,000 readers), a freelancer hub, YouTube, and social media.

70% of his annual revenue of $600,000 comes from his community called "The Lab." It is a close-knit group of 200 entrepreneurs that Jay personally manages.

Jay doesn’t have a massive social media following. His follower count is 45K on Twitter, 37K on LinkedIn, and 70K on YouTube.

But his major currency is trust with his network. Jay studies top creators, analyzes strategies that work, and shares them with the world.

He started as a freelancer after quitting his job in 2017. In a few months, he ran out of money.

The first community he started back in 2017 took him 3 years to get to 115 members.

Table of Contents:

1. Life Before Content Creation

2. How Jay Started Creating

3. First Big Money

4. Jay’s Advice for Beginners

5. Jay’s SIDE (Strengths, Interests, Demand, Execution)

6. How Beginners Can Apply the Lessons

1. Life Before Content Creation

Jay is from Coldwater, Ohio, a small rural town of about 4,000.

His parents were both public high school teachers. They raised their three kids to value education and to be open-minded.

Jay believed in freedom and being recognized for one’s ideas and art.

Days at College

He graduated from Fisher College of Business at The Ohio State University with a degree in marketing.

He tried journalism for a couple of years. While studying journalism, Jay developed a love for deadlines because he had to finish writing before the print date.

His first love in college was comedy. He auditioned for the Student Improv Team and wrote for ‘The Sentinel’, a satirical magazine similar to The Onion.

When he became the leader of The Sentinel, he stopped writing and didn't publish ever. That’s how he learned every business needed a succession plan.

He got interested in business because of an entrepreneurship club at Ohio State. So he started doing internships in small companies.

His journey in community-building started in 2012 with his first Startup Weekend event.

He organized around a dozen of these events where people pitched ideas on Fridays, formed teams, and built functioning MVPs by the end of the weekend.

These events typically hosted around 150 people, forming a powerful community.

Jay’s curiosity and entrepreneurship bloomed as a member and eventual president of the Business Builders Club.

Networking through the club led Jay to his first job right after graduation as co-founder of a software startup, TIXERS.

Life after College

After graduation, Jay shared his apartment with 6 other people.

All of them were passionate entrepreneurial individuals, musicians, and friends who were working on various passion projects.

They hosted house shows for two years, where they brought in local musicians for live performances.

In 2015, Jay and his business partner Alex sold TIXERS.

After the sale, Jay took a job as a product manager with CrossChx, a healthcare startup in Columbus.

There he learned about sales and strategic growth, but he was restless after only a year. He missed the autonomy of TIXERS and wanted more control of his time.

In April 2017, he found out his role in the job would change a lot, so he took just 72 hours to decide to quit with no plans.

He called his parents, saying he quit and might never do a job again.

2. How Jay Started Creating

Jay wanted to use his experience around founders and VCs, along with his rich knowledge as a product manager.

With the desire to freelance, he launched Unreal Collective - a virtual accelerator for founders. It’s like a mastermind where entrepreneurs gathered for 12 weeks with Jay as their mentor.

He started the podcast Upside FM, focusing on startups outside of Silicon Valley.

However, 6 months after quitting his job, Jay ran out of money due to a misunderstanding of his cash flow. He was doing freelance marketing and WordPress development to pay the bills.

While Unreal Collective showed promise, it was still unproven. Many joined the program on blind faith in him. Luckily, he managed to gather 15 people in a cohort.

The Beginner’s Luck

Jay had a stroke of luck when a presentation he uploaded to YouTube caught the attention of the Linkedin Learning team.

He was hired to produce a course in their Product library. This opportunity eventually resulted in him producing four courses with the Linkedin team in 2018.

This was the video that got him the attention.

Jay built a supportive net for freelancers and entrepreneurs through his community.

He taught the same thing repeatedly to freelancers who couldn't afford his growing hourly rate due to increasing demand.

So, he made courses for LinkedIn Learning. He then published them on Freelancing School, a new business he created.

With Freelancing School, Jay created dozens of new videos, proposal templates, email templates, a custom CRM, and more.

3. First Big Money

Jay’s first freelancing project involved helping a client pick a name for his company.

With each subsequent project, he discovered his skills aligned with a particular demand - a blend of website development and copywriting.

It reminds me of Dan Koe who had a similar freelancing experience.

Jay began writing a newsletter that year, laying the groundwork for his community.

The Beginner’s Break

Jay’s community, Unreal Collective grew to over 110 members before being acquired by Pat Flynn who ran SPI (Smart Passive Income) in 2020.

Following the acquisition, Jay led the Community Experience team at SPI, focusing on developing their membership community, course community, and cohort-based courses.

In May 2020, Jay launched his second podcast, 'Creative Elements'. His inaugural guest was Seth Godin, a dream guest for many podcasters. Jay also brought James Clear a few episodes later.

Jay was clear he would ask big names to be on his show.

Having exchanged a few emails with Seth and met James Clear before, he approached them first. Their positive responses made it easier to recruit other guests.

In 2021, most of his income came from sources other than freelancing - digital products, affiliate commissions, and sponsorships.

This marked a stark contrast to his best year of freelancing in 2020, when he barely managed to cross $100K.

How The Lab started

After the acquisition of Unreal Collective, Jay found himself with a lot of free time. He continued to run his newsletter and podcast.

With a desire to create a new community from scratch and leverage his experience and goodwill, Jay began working on the idea in November 2021.

He created a Discord group with 40 people, offering weekly updates on his progress with building the new community as an incentive for those who joined.

It took him three months to design the program, weighing aspects like the stage of the creator, group size, and pricing.

These were the offerings.

Jay then took to social media and offered half-price lifetime memberships to his community even before the program was live. It was named ‘The Lab’.

He leveraged the trust he had built through his newsletters, podcasts, and social media presence. This was his way of rewarding those who took a leap of faith in him.

He attracted his first 100 members in just four months, a number that took him three years to reach with Unreal Collective.

The Lab, Jay's new community, now has a cap of 200 members based on his time commitment and boasts an impressive 90% retention rate.

Here’s what the page reads.

There are 3 pricing tiers - basic ($699), Standard ($1999) and VIP ($2999). Here’s the offer.

This is how his revenue progression looks.

Here’s the tweet on Jay’s revenue timelines.

Jay’s students, like Miles McNair (Google Ads expert teaching SEO) built multi-5 figure of his membership community.

4. Jay’s Advice for Beginners

Freelancers Routes

Freelancers take one of the three routes over time:

1. Create an Agency

2. Create leveraged income through digital products

3. Join a job again

It should be a personal decision.

Transitioning from freelancer to creative entrepreneur requires a mindset shift.

Leverage 2 types of platforms

Begin by utilizing discovery platforms to attract attention, such as social media, YouTube, and search engines.

Then, bring people to relationship platforms like email, SMS, podcasts, and communities.

For Jay, email serves as the primary relationship platform, directing users to his podcasts. His top discovery platform is YouTube, which consistently brings in a high-quality new audience for him.

Mix 2 or more skills

Rather than creating only what you love initially, start by making what the market wants but add your unique twist.

Jay excelled at website copy, email systems, and email writing for clients, making him more valuable in the market.

Audience specificity

Certain niches may lack disposable income, while others may readily accept higher prices. It's essential to select a niche with a high disposable income to ensure profitability.

Show confidence

As a freelancer, your aim is to be better than your clients, not necessarily the best.

Rather than faking it till you make it, convey confidence in your abilities, albeit with honesty. This confidence stems from experience, so practice regularly and maintain a record of successful projects.

5. Jay’s SIDE

Any creator can succeed when they get their SIDE right. It’s a simple framework beginners can use to start creating online.

SIDE = Strengths + Interests + Demand + Execution

Let’s look at Jay’s SIDE.

Strengths

• Focus on excellence

• Sales and marketing

• Writing

• Creativity

• Networking

Interests

• Building products

• Community

• Entrepreneurship

Demand

• Freelancers wanting business guidance

• Website development

• Email integration

• Copywriting

Execution Milestones

• Quit job (2017)

• Started community - Unreal Collective (2017)

• Started Newsletter - Creative elements (2017)

• Launched podcast - Upside FM (2017)

• Started website - Freelancing School (2019)

• Launched podcast - Creative Elements (2020)

• Sold Unreal Collective to Pat Flynn (2020)

• Started The Lab (2022)

Pause here for a moment.

Think of what can be your SIDE. Write on paper or digital notes.

Use it as a starting point to pick ideas you want to write about.

6. How Beginners Can Apply the Lessons

Set up systems

When doing multiple tasks, it's important to create systems and processes.

Jay emphasizes releasing products on a schedule, which he calls creative commitments.

Here's Jay's plan:

• Newsletter: Every Sunday

• YouTube video: Every Monday

• Podcast: Every Tuesday (based on the YouTube video)

• Social media (Twitter, LinkedIn, Instagram): 1-2 times a day

Know your audience

To solve problems effectively, you need a clear understanding of your ideal audience.

Jay initially worked with founders and creators, but with the Lab, he focuses solely on intermediate creators, avoiding the need to persuade beginners to start creating content.

Build trust through free content

It's important to build trust with your audience by consistently providing free content.

Jay's journey began with writing in 2017, which laid the foundation for success in all his ventures.

3 types of creators

There are three main types of creator spaces: education, entertainment, and a combination of both. It's crucial to define your space clearly.

Jay primarily works with creators in the education sector, finding it more profitable and engaging.

Promote your work

As a freelancer or creator, it's important not to hesitate in promoting yourself.

Jay's strategy involved maximizing the value of every project. He aimed to get a testimonial for each client project, transforming it into a case study showcased on his website.

This approach allowed Jay to appear accomplished when he started, despite having only a few clients, comparable to someone with years of experience.