My Sibling's Sidehustle Sacrifices and Strategies for Success - Jenna Kutcher

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My Sibling’s Sidehustle Sacrifices and Strategies for Success

Jenna Kutcher 

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Show of hands… How many of you know that I have a brother? I’m imagining about 4 hands up in the air and they’re all related to me. My brother Joe Shelerud made a short cameo on the podcast once before, during my birthday episode last year, but truth be told, he’s quite the serial-entrepreneur and it seems so funny that I’ve never featured his story on Goal Digger. In fact, he was the one who told me, years ago to start my own podcast, so without him, this show probably wouldn’t exist.

All of my siblings and I are entrepreneurs in some form, and yet we didn’t have any direct influence in this area growing up. My sister runs a thriving blog and Instagram platform in her perfectly-Kate niche, I’ve got my business that you know fairly well by now, and then there’s Joe who built an incredible advertising agency to help small businesses sell their products on Amazon. He also travels the country in an RV with his wife and three children — don’t worry, we’ve got a story around that that you’ll get to hear too! 

It’s such a treat to get to introduce you to my brother on the show. Meet the guy who shared the fire engine bunk beds with me and a human who shares a lot of the same memories I have!

My Brother’s Story

Joe’s entrepreneurial journey began alongside mine — lemonade stands at the end of our driveway on a very quiet rural street. From there, Joe became the true definition of a serial entrepreneur. His background is in chemical engineering, but his side projects ranged from a joke website at age 14 to a device for monitoring the temperature when brewing beer with his college roommate. 

Joe went back to school to get his MBA while working full-time. After, he took a job in Wichita, Kansas and while it was a great corporate opportunity, he realized quickly that he and his wife missed being with family. It was then that he started to take the entrepreneurial route more seriously. 

He studied up on Amazon selling strategies and (this is the short version) went on to do seven figures in revenue once he figured out his own systems that worked well. Joe realized that the tools he’d created for himself for selling and advertising on Amazon could actually help other people do the same. The Amazon and AdAdvance world allowed him to move back to Minnesota and his family. 

Keys to Side Hustle Success

Joe balanced so many things at once when he was getting his business off the ground. For Joe, the key to making the most of limited time was getting really clear on your goals for the business and making sure your partner (spouse, girlfriend, boyfriend, whoever) fully understands that goal. 

When you’re working on a side hustle and you have a full-time job plus you have the other obligations of family and life, there will be things that you cannot manage on your own. Having buy-in from a partner, or even support from a friend or someone who can help you with the things that fall through the cracks is key.

Also, Joe encourages you to make a conscious effort to give up the things that you need to give up in order to have enough time to work on your side hustle. Joe continued, “Once you look at that, they you have to weigh it and make sure that you’re still all in once you realize what you have to give up.”

Going Full-Time

The goal for Joe was to go full-time with his business, but it’s not something that happened without planning and preparation. One step that played a role in his ability to go full time with his business was saving all of the money he’d made with his side hustle in a separate account and not touching it. That became a safety net.

Joe also knew that a key motivator for starting a business was so he and his family could travel. As their kids got older and it reached the point where their oldest was about to enter kindergarten, they knew it was now or never. Having that external motivation to get the business to a place where he could go full-time also helped him focus.

Living in an RV

Did I mention that Joe and his family of five live in an RV and travel the country for part of the year? My brother’s initial pitch to his wife was to sell their home and live in the camper full time… It didn’t sell well. A year later, they’d determined that the opportunity to travel part of the year and still have a home to come back to was the best route for their family.

Now, their kids have been to over 40 states, they explore new places all over the country on a whim, and Joe can still run his business from the road. 

If you want to follow along with their travels in the RV, go follow @wanderingwithfive. It’s so fun to see their adventures and learn how they make it work with three kiddos and a camper.

More from this Episode

What did the pandemic put his ecommerce business through? How did he build a profitable business without much of a social media presence? What is Joe learning now about social media that he previously avoided as an introverted engineer? This is such a different and fun conversation with my brother about business, life, and working hard to achieve the vision you have for both. Press play now wherever you get your podcasts.

Want to learn more about selling on Amazon? Joe put together a few resources for Goal Diggers.


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