Podcast Episode: From Side Hustle to Swim Success: How to Pivot Your Online Business Without Drowning with Joanna Whitbeck

What do you do when you’ve made six figures selling courses about making money online, but you wake up one day and realize you can’t stomach it anymore? Most people would be terrified to walk away from that kind of success. But my guest today, Joanna Whitbeck, did exactly that – and built something even better.

Joanna went from making over $100,000 reselling digital marketing courses to completely pivoting into the swimming niche, building a brand new business from scratch. And in less than eight months, she’s built a swimming account to 45,000 followers and created multiple profitable courses teaching swimmers and triathletes.

Her story isn’t just about pivoting – it’s about what it really takes to build a sustainable online business when you stop chasing quick money and start building something real.

The Physician’s Assistant Who Smelled the BS

Joanna’s entry into the online business world sounds familiar to anyone who was on social media in 2023. She saw women singing and dancing about the millions they were making through “high ticket affiliate marketing.”

But unlike most people, Joanna’s BS detector was working overtime.

“I was like, okay, I can smell the BS from a mile away, but let me just, I’ll pay $7 to step in a little bit of crap here.”

As a physician’s assistant with four kids under eight, Joanna was drowning in the chaos of daily life. She had no hobbies, no time for herself, and when someone asked what she enjoyed, her answer was “I like to go for a foot massage once a month.”

She wanted to build something meaningful but wasn’t interested in the rags-to-riches fairy tales being sold everywhere. When she found my content focusing on education rather than income claims, something clicked.

The Unicorn Beginner Who Actually Made It Work

I call people like Joanna “unicorn beginners.” She had never technically built an online business before, but she had life skills that translated perfectly:

• Time management skills from managing four young kids and a demanding career
• Self-confidence from being a successful healthcare professional
• Natural authenticity that people could feel through the screen
• Clear communication skills from her medical background

She bought my Roadmap course in October 2023 and went on to make over $100,000 reselling it. But here’s what made her different from most course resellers: she actually did the work, learned the material, and genuinely helped people.

“I was really sharing my journey with, you know, okay, this is what I’m learning. This is what I’m doing with it. And I was really talking a lot about the swimming business and my plan to build another business.”

The Reality Check That Changed Everything

Despite her success, Joanna started noticing something that made her uncomfortable. She had what she called “box checkers” – people who were doing everything right, showing up every day, following all the strategies, but still not seeing success.

“I was running out of, like, I was like, I don’t, I don’t know how to help my box checkers other than to tell you, you should pivot out of this space.”

The problem? She was telling people to do something she hadn’t done herself. And as someone with integrity, that didn’t sit right with her.

Add to that the “dumpster fire of income claims” happening in the space – the fake Stan Store screenshots, the outrageous earnings promises – and Joanna realized she couldn’t stay associated with that world.

“I lost more followers than I could have even fathomed when I started sharing content about how to generate income without sharing your income. The people came for me and I’m like, well, wait a minute. I’m trying to do the right thing.”

The Strategic Pivot: From Money to Meaningful

Instead of just walking away from her successful course business, Joanna made a strategic decision. Her husband was a former collegiate swim coach, and she’d been talking about building a swimming business all along. So she decided to actually do it.

On April 17th, she posted for the first time on @swimtrisocial. In less than eight months:

• 45,000 followers on Instagram
• 2,000 email subscribers
• Multiple profitable courses from large comprehensive programs to micro mini-courses
• Consistent sales every Monday from email marketing

Their target audience? Swimmers and triathletes who are overwhelmed by the swim portion of races and just want to survive to get to the bike portion.

What She Learned About Real Business Building

Building a business from scratch in a completely different niche taught Joanna lessons that the course reselling world never could:

1. Brand Awareness Matters

“When I was selling courses within the MRR space, there was already brand awareness. People were aware of the product and you just had to be the person that they would purchase from. When you’re building a business from scratch, all of the things – copywriting, sales funnels, email marketing – became really important.”

2. What People Need vs. What They Want

“I know exactly what my audience needs. We help swimmers become strong freestyle swimmers. But what they want is different. It’s my job to figure out how to lessen that gap between what we know they need and what they want.”

3. Emotional Content Converts Better Than How-To

One of Joanna’s biggest realizations was that she was creating how-to content to sell her how-to courses. While this gets some results, emotional content reaches people who are actually motivated to buy.

4. The Power of Focused Effort

Following my advice to “master one thing at a time,” Joanna stopped posting on her affiliate marketing account and focused solely on email marketing for the swimming business. Result? Sales every Monday from her email list.

The Expectation Trap That Derails Most Businesses

One of the most powerful parts of our conversation was when Joanna talked about expectations. Her first live launch for the swimming business generated $700 in sales, and she was devastated.

“I was mortified because my expectations, especially seeing all social media posts and a lot of the big gurus who share their income… I look back and I’m so sad for what I was feeling at that moment because I should have been beyond proud that anyone showed up to listen to my husband speak about freaking swimming.”

This is the trap that kills most online businesses. People see others sharing their $10,000, $30,000, or $60,000 launch results and think that’s normal. It’s not.

“Your expectations have the ability to completely derail your business. If you sell anything, you should be proud of yourself.”

Real Talk About Beginners Selling Courses

When I asked Joanna about beginners selling courses about making money online (which is exactly what she did), her answer was refreshingly honest:

“I think if you come into this with the expectation that you are just a salesperson, you are selling digital courses and you’re going to have to figure it out as you go, I think that it can be done for sure. But I don’t think that I could say that it’s the worst idea.”

The key difference? She actually learned the material. She did the training. Too many people in that space just “plastered the link inside their Stan store” without ever going through the education they were selling.

Why “It’s Oversaturated” Is a Cop-Out

When people say online business is oversaturated, Joanna has the perfect response:

“They are correct if they plan to be the same as everyone else. The problem is not the saturation, it’s the sameness.”

The solution isn’t finding an “untapped” niche. It’s being authentically yourself in whatever space you choose to enter.

Advice for People Who Don’t Know Their Niche

For those who don’t have a “swimming business” in their background, Joanna’s advice is simple:

“I would say developing a personal brand and a community. Show up on social media and share your daily life, share things that you like, see what resonates with the audience that you build.”

The key insight? When you start, nobody’s listening anyway. That’s actually perfect because it gives you time to practice and figure out what you enjoy and what people connect with.

The One Thing That Would Have Changed Everything

When I asked what she wished she’d known in October 2023, Joanna’s answer was simple: expectations management.

“If I had known that the average person does not make $10,000 on a brand new social media account building a completely brand new baby business, I would have been much more content and much more excited to show up to build the business.”

The Bottom Line

Joanna’s story proves that you can successfully pivot from a “make money online” business to something real and meaningful. But it requires:

• Integrity to walk away from easy money when it doesn’t feel right
• Patience to build something from scratch
• Realistic expectations about what success actually looks like
• Focus on mastering one thing at a time instead of trying to do everything
• Authenticity that makes you stand out in any niche

The course reselling world taught her valuable skills, but building a real business from scratch taught her what entrepreneurship actually looks like. It’s messy, it’s slow sometimes, and it requires constant learning and iteration.

But when you’re building something you’re actually passionate about, with people you genuinely want to help, the whole game changes.

Your brain needs evidence that you can make $1. Then it starts believing you can make $100. Then $1,000. Then more.

Stop looking for the one solution that’s going to fix all your business problems. Success is “a culmination of all of the tiny things that you do every day rather than one thing.”

Start somewhere. Be authentic. Help people. The rest will figure itself out.

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Ready to dive deeper into building your digital empire? Subscribe to Beyond the BS and follow me on Instagram @the_no_bs_newyorker. Find Joanna’s swimming business at @swimtrisocial and connect with her at @Thesocialharbor.

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