62: Generating Lifestyle Business Ideas That Work

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Jesse Krieger is THE Lifestyle Entrepreneur, and author of the book of the same name, subtitled Live Your Dreams, Ignite Your Passions and Run Your Business From Anywhere in The World.

Today we’re chatting about how aspiring side hustlers can come up with new business ideas, validate them quickly, and begin earning money outside of their day job.

It’s a fun session with a lot of brainstorming out loud on various ideas and methodologies of going to market.

I first connected with Jesse through a HelpAReporter query I put out about how to find a business coach, and he was among the responses. Then he sent me a copy of his book and I thought he would be an interesting person to bring on for the podcast.

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  • Why some people think the term “lifestyle business” is a negative.
  • How Jesse recommends side hustlers come up with business ideas.
  • Why competition in your marketplace is actually a good thing.
  • How to put your unique twist on an existing product or service to start your own business.
  • Jesse’s “Business in a Weekend” framework.
  • Our thoughts on start-up costs / investments, and why you should consider the compound effect of investing in yourself.
  • Jesse’s #1 tip for Side Hustle Nation.

Jesse Krieger Quote


What do you think? Does Jesse’s lifestyle business framework work for you? Let me know in the comments below.

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In the comments below, share your biggest takeaway from this week’s show and I’ll select a winner to send a free copy of Lifestyle Entrepreneur! Hurry, this contest closes next Thursday, July 31st.

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

31 thoughts on “62: Generating Lifestyle Business Ideas That Work”

  1. Nick,
    I love the idea of business in a weekend course. Jesse’s example on creating a conference was a great one. I am curious why some people have a negative feeling about “lifestyle business”, or even “internet business”?
    Do you think for “internet business” that tide is slowly turning toward the positive since we are seeing more and more people creating valuable products?
    Great show

    • Hey Ryan, thanks for checking out the episode. It is funny how some people conceive a “lifestyle business” as a negative thing. It’s likely because there are a lot of hucksters out there and there are a lot of crap products, programs, books, etc. that make it sound super easy to “get rich online” – It takes effort to build any business BUT the upshot is that with an online business, you have the freedom to travel and do what you love once it is set up and running

  2. Nick I actually found a number of great takeaways during this podcast but the Biggest Takeaway is building a business around a person’s interest and passion. Afterwards look at the economy around it for products and services. This is essentially how to monetize it. Look for opportunities for training, coaching, information products, or whatever to build a business around this passion. As Jesse said it’s not about a means to the end.

    • Mark,
      Great points. Building a business around interests will keep you fueled when times get tough, or the road is slower going than you had imagined.
      I would also suggest taking a look at products/services you like and see if there is a way to build an insider’s guide, or find a way to create ancillary products and services around them. The one that best comes to mind is Evernote Essentials. I never thought I would have needed that but it has become a useful tool with every update.

    • Hey Mark, glad you liked the episode! You nailed it, business shouldn’t be just a means to an end because it could take a loooong time to get to the end, or it may not work out at all. I’d always rather fail playing the game I want to win, then to “succeed” doing something I don’t enjoy.

  3. You know, as I listened to this, all I thought about was the old quote, “either crap or get off the pot!” when it comes down to starting and investing in yourself/business. So many have the mindset that we got from our schools that failure is a bad thing. As a teacher, I try to share with the kids that failure is a great opportunity to learn something new! My advice to all side hustlers, is to get out there and try and spend a little money on yourself and your business. Just by starting, it is now not a matter of if, but it is now a matter of when you will be successful! And you will learn and be more successful than where you currently sit (that pot-lol!)!!!!!

    • Love it Domenic! Failure is inevitable, there is no avoiding it. And if you fail enough times, then inevitably you have some wins along the way. I use baseball as an analogy…Babe Ruth, one of the all-time greatest home run hitters, still struck out 7/10 times at bat. Thats MORE than 50%! Michael Jordan, same deal. Entrepreneurship is no different, and you learn 10x more from making mistakes than getting lucky the first time.

      Investing in your learning, trying out ideas, building things (business, blog, podcast) is always more rewarding that buying stuff. I could go on, but I think we’re on the same page :)

  4. Great episode Nick. I’m checking out the Big 3 websites for value dense products right now. Thanks for another awesome interview. I still want to learn more about Drop Shipping. Have you done a show on that yet? I may have missed it.

    • Hi Krystal, glad you enjoyed the episode! That concept of value density could easily save you a huge business headache, really glad Nick asked me about it. There is a lot of info in my book, Lifestyle Entrepreneur about setting up a drop-shipper, or just shoot me an email.

      Best – Jesse

  5. Great show!! My big takeaway is that everything does not have to be brand new, it can be a crank of something already in existence. I’ve been going crazy trying to think of the ‘next big thing’ and it doesn’t have to be that way! A quick update or a more efficient way to do something is all I may need. Thanks!!

    • Hi Tanisha, glad you liked the show! Yes, that’s a good takeaway. In fact, most “innovation” is really an incremental improvement on what already exists. When you create something brand new you run the risk of creating something no one wants. Finding something successful and adding your own twist to it (ie, adding value) is a faster, easier path to entrepreneurship.

    • Indeed — I like the idea of iterating on a current product or service with your own unique value added twist.

      For example, with my shoe business, it definitely wasn’t the first comparison shopping site in the world, but it was the first (that I know of) completely dedicated to footwear. Because of that, we could have tighter algorithms and work closer with the stores for exclusive deals.

  6. My biggest takeaway was the idea of investing in yourself. I recently read an article about networking that suggested setting aside money each month for an “interesting people fund” so there’s no reluctance or guilt and you can jump on opportunities to meet new people or reconnect with mentors. So a similar idea of setting aside money to spend on yourself and business makes a lot of sense to me. Thanks for the great episode!

  7. Thanks for another great episode Nick and Jesse!

    I love the idea of setting a portion of your earnings to explore new ideas… a “business development” fund so to speak. All too often I’ve had ideas that I wanted to pursue but put it on the back burner because I didn’t want to invest the cash in it on a short-term basis. This is something I’ll definitely be implementing over the next month or two.

  8. My biggest take away was validation. I am already sketching out and outlining ideas, researching if or when I should execute. Setting aside cash and time for development was a key take away for me.

      • I had an hour long business train ride (that’s two hours) so I revisited this podcast and… boom. Realization hit me. I spent a good two hours last night trying out different blog engines and custom coding a web site *but* I already HAVE a website. Anyone that can operate a mouse and type a language can make a page on About.me! I checked tonight and immediately updated my tags and bio. Bonus win: About.me has stats built-in. Even without my keyword tune-up my page was viewed over 800 times this week (over 3K this month, over 24K this year).
        I may still do a custom website but now I am under less pressure for that item and can focus on connecting with new clients instead.

  9. I’m listening to this for the second time as there are so many great takeaways that I couldn’t keep up with all of them the first time around!

    The thing I really connected with the most is idea creation as I really struggle in this area. I’ve always viewed coming up with ideas as a mountain sized thing that has to be invented, but this podcast did an excellent job of helping me to focus on developing related products based upon the main subject (i.e. biking gloves versus a new type of bike).

    This makes things seem much less daunting and gives you the advantage of doing something better than existing products since you can really focus on a specific area instead of trying to cover all the bases.

    Thanks Nick and Jesse for a truly epic episode!

      • Nice! I’m still trying to get caught up on your podcasts so I’ll listen for it. Good news is that the yard needs mowed so I’ll have plenty of time to listen :)

        On a side note I signed up for Ryan Findlay’s Appliance School and plan on documenting it so others can see how this side hustle goes. Pumped to hear that you’re finally going to have him on the show!

  10. Biggest Take-Away – You have to exercise your will in doing tthis….that is, you must make the decision to do it. Until the decision is made, it’s a pipe dream.


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