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15 Interesting Lifestyle Entrepreneur Examples You Should Know About in 2020

If you’re looking for lifestyle entrepreneur examples, you’ve come to the right post.

lifestyle entrepreneurs aim to build lifestyle businesses that enable them to prioritize their ideal lifestyle first, profits second. 

I wrote a post about lifestyle entrepreneurship here that takes a deeper dive into this topic. 

So who are some real-world lifestyle entrepreneur examples?

And how do they earn their income? 

Let’s start with perhaps the most famous lifestyle entrepreneur, Tim Ferriss. 

Tim Ferriss 

Tim brought the concept of lifestyle entrepreneurship into the mainstream with his massively popular book, The Four-Hour Workweek.

If you haven’t read it, you really should. 

But for now, here’s a one-sentence summary from fourminutebooks.com: 

The 4-Hour Workweek is the step-by-step blueprint to free yourself from the shackles of a corporate job, create a business to fund the lifestyle of your dreams, and live life like a millionaire, without actually having to be one.

Summary from Four Minute Books

In other words, The 4-Hour Workweek is all about lifestyle entrepreneurship! 

Since this book, he has continued writing popular books and blog posts as well as running a globally renown podcast. 

Tim uses these diverse income sources to build a lifestyle of freedom and travel. 

Michelle Schroeder-Gardner 

Michelle is a personal finance blogger who has achieved massive success driving traffic from Pinterest to her blog. 

More recently, she has diversified her traffic, focusing on SEO and other traffic sources. 

As her business has grown, she has also diversified the ways she earns income from her blog. 

However, she started out earning money from affiliate marketing. 

Michelle stopped disclosing exact income numbers in 2018.

She has made more than $1 million in annual profit from her blog

She has also lived in an RV and sailboat with her husband and two dogs, traveling around the world. 

Like many lifestyle entrepreneurs, she has taken advantage of the location independence her business provides to work wherever (and whenever) she wants. 

Johnny FD

Johnny FD is a great example of a lifestyle entrepreneur who is also a digital nomad. 

All he needs to make money is a laptop and an internet connection. 

So he takes advantage of this, traveling all around the world (particularly Asia). 

Part of the reason he lives in Asia is to leverage the lower cost of living in parts of Asia compared to the US. 

This enables him to save a large portion of his income. 

Working in lower cost of living countries while earning USD is common among lifestyle entrepreneurs for this very reason. 

You can check out Johnny’s income report’s here to learn about the diverse ways he makes a living online. 

Jasmine Alley

This one’s my personal favorite because Jasmine is my wife! 

I also wanted to include an Instagram influencer on this list since the influencer industry is less transparent about their income than the blogging industry. 

Jasmine has managed to make a living as a travel influencer on Instagram through brand collaborations. 

In fact, Instagram brand collaborations are her current primary source of income. 

You can read all about her sources of income and exactly how much she makes on her income report here.  

Jasmine spent two years working on her travel brand after hours before she left her day job. 

Now she leverages her brand to visit beautiful places all around the world with complimentary luxury hotel stays!

Jasmine actually made more from her day job than she is currently making as a travel influencer.

But she now lives her ideal lifestyle of fun, independence, and luxury travel. 

In other words, she has priortized her ideal lifestyle first, profits second. 

That said, there’s no limit to the income she could make from her online business1 

Pat Flynn

Pat Flynn is up there with Tim Ferriss as one of the most famous lifestyle entrepreneurs ever! 

He started blogging before it was cool (and before most people knew you could make a living blogging). 

Today, he runs a content production empire at smartpassiveincome.com.

Although it might not look like it today, Pat started his businesses to prioritize time with his family. 

These are really common motivations for lifestyle entrepreneurs. 

Also, Pat was making millions a year from his blog and is likely making even more today.   

Melyssa Griffin

Melyssa Griffin has a common lifestyle entrepreneur story.

She felt burned out selling services as a graphic designer and then experienced great success selling products instead of services.

Once she started selling online courses, she experienced massive success, riding the explosion in popularity of online courses. 

Melyssa he no longer publishes income reports.

But in December of 2016 she made nearly $200,000 of profit in that month alone!

As her business has grown, we can only assume her income has also grown.  

Brian Dean

Brian Dean’s story is similar to Melissa’s in that he started out selling services.

But he quickly realized he needed to sell a product if he wanted to live the life of his dreams. 

Today, he runs a highly successful SEO blog called backlinko and, like Melyssa, sells online courses. 

Brian has an interesting story you can read more about here.  

Shelby Church

Shelby is a west-coast-based YouTuber and vlogger. 

She is one of the more inspiring lifestyle entrepreneur examples on this list.

Why?

Unlike many lifestyle entrepreneurs mentioned in this post, she doesn’t make millions from her lifestyle business. 

In her 2019 income recap video above, she discloses that her channel brought in about $140,000 in revenue. 

After taxes and expenses, this is probably closer to $100,000 (or less). 

Although still a great income, this seems more achievable than the millions some lifestyle entrepreneurs make on this list. 

I aslo respect Shelby because she practices radical transparency.

She discloses details about her income, a trait seemingly more common among lifestyle entrepreneurs than standard entrepreneurs. 

John Lee Dumas 

John Lee Dumas is a successful podcaster, interviewing entrepreneurs on his hit show, Entrepreneurs on Fire. 

Of the lifestyle entrepreneur examples mentioned here, I appreciate John Lee Dumas’ advice about hard work the most.

He says you must F.O.C.U.S or Focus on One Course Until Successful.

John followed his own advice and recorded a podcast episode every single day for nine months without making a penny!

And he continued producing daily content for 2,000 days before he slowed down. 

Now he regularly nets six figures in profit per month from the podcast!

Few people have the conviction and discipline to work on something every day for months without making any money. 

And even when he did start earning income from his podcast, it was a slow build. 

But he stuck with it and now earns a great living from it. 

John illustrates the challenge of lifestyle entrepreneurship in particular (and often entrepreneurship in general): 

That earning a living from a lifestyle business often takes years to accomplish. 

But if you stick with it, there’s the potential to make a great living from your lifestyle business. 

Lindsay Mostrom

Lindsay runs a food blog with her husband at pinchofyum.com.

Although they stopped producing income reports in early 2017, this particular income report shows them making ~$70,000 of monthly profit! 

Since it seems their business has only grown since then, they are likely earning an even higher income today!  

Of course, it took years to get to that level of profit. 

And when they started their blog, there there was less competition in food blog space. 

That said, I’m happy to include a food blogger on this list of lifestyle entrepreneur examples.

It shows just how diverse the opportunities are for lifestyle entrepreneurs. 

Of course, lifestyle entrepreneurs typically choose specific business models to facilitate their ideal lifestyle. 

But the niches and opportunities within these business models is vast. 

Pieter Levels

Pieter Levels runs a handful of SAAS businesses that make him $600,000+ per year

He manages these businesses by himself as a solopreneur and travels the world as a digital nomad. 

For those not familiar, SAAS businesses are typically web applications like Google Drive or DropBox.

SAAS business owners often monetize by requiring a monthly or annual subscription from their users.

DropBox is a good example of a subscription-based SAAS, but there are countless others. 

This business model is so attractive to lifestyle entrepreneurs for many reasons, one of which is the recurring revenue.

Pieter is extremely transparent with his businesses. 

He practices building in public (posting regular updates about his projects to Twitter).

He also lists his traffic, revenue, and more business statistics here.  

If you want to learn more about Pieter’s business philosophy, check out his e-book here.

Marie Forleo

Marie Forleo has a fascinating career. 

Like Tim Ferriss, it seems her work as a New York Times bestselling author launched her career. 

Besides being a popular author, she is a professional dancer and has her own YouTube series and podcast. 

Her diverse sources of income have allowed her to lead an exciting life.

Also, many lifestyle entrepreneurs look up to her for business advice. 

You can learn more about what she’s up to on her blog here.

Daniel Vassallo 

Daniel launched himself into the lifestyle entrepreneur scene with his popular blog post

Only Intrinsic Motivation Lasts: Why I Quit a $500K Job at Amazon to Work for Myself

As you can probably tell from the post title, Daniel has an interesting story.

And he brings a unique perspective to lifestyle entrepreneurship. 

Not many people would leave a corporate job earning a top 1% income to strike out on their own. 

However, Daniel did and has since sold e-books, e-courses, and SAAS. 

You can find detailed descriptions of exactly how much he makes and more in posts like these

I appreciate Daniel’s open style and look forward to what he does next in his journey as a lifestyle entrepreneur.

Kristen Larsen

Kristen Larsen is a personal finance mom blogger who runs the blog Believe in a Budget

Although she stopped reporting income around July of 2018, she made around $15,000 in profit that month.  

In other words, she has made a great living as a blogger. 

Mom bloggers could easily fill this entire list of lifestyle entrepreneurs.

However, I didn’t want to happen because I wanted to include a diverse list of lifestyle entrepreneur examples and businesses.

But I still want to mention Kristen since I don’t have any other mom bloggers on this list.

Why?

The prevailing mom blogger philosophy seems to fit well with lifestyle entrepreneurship. 

Mom bloggers typically want to work whenever and wherever they want so they can prioritize family time first. 

Plus, they leverage technology to do this.

They write about content they find interesting and share it on platforms where their target audience spends time (like Pinterest). 

These characteristics are at the heart of lifestyle entrepreneurship. 

Peter Adeney 

If you’re interested in personal finance, you may have heard of Mr. Money Mustache (aka Peter Adeney). 

Peter is unique in that he built the business of his dreams by accident.

In fact, he started his blog after he had already retired. 

His blog, mrmoneymustache.com is where he writes about index fund investing, frugality, and early retirement. 

He started the blog in 2011 after he had retired in 2005 (in his thirties!).

He was able to retire in part by maintaining a low cost of living.

This way, he could invest more than half of his income in low-cost index funds. 

Once he retired, he started blogging for fun.

And now he makes $400,000+ annually from his blog!

Despite this extra income, he maintains a life of frugal living.

Why?

He doesn’t consider it frugal.

In fact, he says that just the life he wants to lead:

  • spending time with his family,
  • working on whatever he wants,
  • and enjoying the natural beauty of Colorado.   

I’m happy to include Peter on this list as a unique example of someone who created a lifestyle business after early retirement. 

Plus, the concepts of early retirement or FIRE (Financial Independence Retire Early) and frugal living often overlap with lifestyle entrepreneurship. 

Conclusion

I hope this list of lifestyle entrepreneurs has inspired you to get started in lifestyle entrepreneurship if you haven’t already!

Who are your favorite lifestyle entrepreneurs? 

Let me know in the comments!  

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