Episodes

  • Built to Sell: Design a Business to Run Without You (Greatest Hits)

    Built to Sell: Design a Business to Run Without You (Greatest Hits)
    Feb 6 2025
    Service businesses can get a bad rap. After all, there are clients to deal with, and actual labor involved in fulfillment. They’re just not as glamorous as other more “passive” income models. But you should know that more Side Hustle Show guests started with a service-based business model than any other. This week’s guest has a unique approach to service businesses -- one that doesn't rely on your skills as the expert. Tyler Gillespie has built two successful service businesses and had a clean exit from both -- the last being just 13 months from startup to sale. Tune in to hear: how Tyler comes up with ideas for productized service businesses the processes he implements to put his business in a position to exit how he outsources the mechanism of his businesses Full Show Notes: Built to Sell: Design a Business to Run Without You New to the Show? Get your personalized money-making playlist here! Sponsors: Airbnb — Discover how much your home could be worth and find a professional co-host today! Mint Mobile — Cut your wireless bill to $15 a month! Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post! OpenPhone — Get 20% off of your first 6 months! Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
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    51 mins
  • 654: I Interviewed My AI Self … What it Got Right, Wrong, and a Little Weird

    654: I Interviewed My AI Self … What it Got Right, Wrong, and a Little Weird
    Jan 30 2025
    It’s 2025, and the line between reality and science fiction is getting more and more blurry every day. In this episode, I sit down with someone I’ve never met, but they know me pretty well. He even kind of sounds like me in an eerie sort of way. I was curious how well today’s AI models could pretend to be someone else, given a few simple prompts. The result is this chat with Robo-Nick, my AI alter ego. Let’s see how well Robo-Nick answers these questions, plus my real thoughts about them. (This episode relied heavily on ElevenLabs to generate the voice for Robo-Nick.) Tune in to episode 654 of The Side Hustle Show to learn: The biggest opportunities (and pitfalls) for side hustlers in the AI era. Actionable tips to future-proof your income and leverage new trends effectively. Full Show Notes: I Interviewed My AI Self … What it Got Right, Wrong, and a Little Weird New to the Show? Get your personalized money-making playlist here! Sponsors: Airbnb — Discover how much your home could be worth and find a professional co-host today! Mint Mobile — Cut your wireless bill to $15 a month! Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post! OpenPhone — Get 20% off of your first 6 months! Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
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    50 mins
  • 653: 3 Ways to Escape of the Rat Race

    653: 3 Ways to Escape of the Rat Race
    Jan 27 2025
    Getting out of the rat race is simple, but not necessarily easy. To escape, all you need is monthly income -- from non-job sources -- that exceeds your monthly expenses. For example, if you spend $3000 a month, you'll need to bring in at least $3000 (after taxes) outside of your day job. Simple, but not always easy. In this episode, I'll break down: the most common rat race "escape routes" the pros and cons of each how to choose the right path for you Ready? Let's do it! Full Show Notes: 3 Ways to Get Out of the Rat Race New to the Show? Get your personalized money-making playlist here! Sponsors: Airbnb — Discover how much your home could be worth and find a professional co-host today! Mint Mobile — Cut your wireless bill to $15 a month! Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post! OpenPhone — Get 20% off of your first 6 months! Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
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    34 mins
  • 652: $150k Renting Out Dresses as a Side Hustle

    652: $150k Renting Out Dresses as a Side Hustle
    Jan 23 2025
    In 2022, Summer Fisher discovered the world of renting out dresses. "Oh, well, I have all these dresses. Let me just put one up," she told Yahoo Finance. Now with a streamlined inventory of around 200 pieces, she made $150,000 last year using what she calls a "double-dip profit strategy" — renting dresses multiple times before selling them for more than she paid. (Check out her free masterclass at theprofitcollective.co/RookieResellerMistakes.) Tune in to episode 652 of The Side Hustle Show to learn: Summer's favorite brands to rent out. Her pricing and profit margin math on her inventory. The logistics of shipping and selling dresses. and more. Full Show Notes: $150k Renting Out Dresses as a Side Hustle New to the Show? Get your personalized money-making playlist here! Sponsors: Airbnb — Discover how much your home could be worth and find a professional co-host today! Mint Mobile — Cut your wireless bill to $15 a month! Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post! OpenPhone — Get 20% off of your first 6 months! Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
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    48 mins
  • 651: How to Make Money on LinkedIn

    651: How to Make Money on LinkedIn
    Jan 16 2025
    If you’re looking to turn LinkedIn into a money-making machine, you’re in the right place. Joe McKay has taken his LinkedIn ghostwriting side hustle from zero to a multi-six-figure business, generating millions of impressions along the way. And he's here to fill us in on how to make money on LinkedIn this year. We broke down the 3 types of posts you need to make money on LinkedIn, how to navigate the platform as a side hustler, and the most common (and costly) mistake people make. Listen to Episode 651 of the Side Hustle Show to learn: the 3 LinkedIn posts every side hustler must use why building connections strategically changes the game how to avoid the costly mistake most people make Subscribe to Joe's The Thought Follower newsletter for more LinkedIn tips and solopreneur strategies. Full Show Notes: How to Make Money on LinkedIn New to the Show? Get your personalized money-making playlist here! Sponsors: Airbnb — Discover how much your home could be worth and find a professional co-host today! Mint Mobile — Cut your wireless bill to $15 a month! Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post! OpenPhone — Get 20% off of your first 6 months! Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
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    51 mins
  • The Sweaty Startup: How to Start a Local Service Business (Greatest Hits)

    The Sweaty Startup: How to Start a Local Service Business (Greatest Hits)
    Jan 13 2025
    Do you know how much cash flows through your hometown on a monthly basis? In this episode we explore how to get some of that cash flowing toward you! I'm joined by Nick Huber, co-founder of Storage Squad and host of The Sweaty Startup podcast. Storage Squad, a student storage service, has grown to over $3M in sales since starting it as a little part-time project back in 2011. I invited Nick on The Side Hustle Show to help walk us through his "sweaty startup" framework. That is, how you can start a low-risk, low-overhead, local, service-based business, set it up for success, and let that be the vehicle that drives you away from a lifetime of cubicle slavery. Tune in to hear Nick’s thoughts on generating service business ideas you could start today, evaluating the market and competition, and scoring your first customers. That’s why I think this is pretty exciting -- it really doesn’t take many customers to begin to make a meaningful income here. Full Show Notes: The Sweaty Startup: How to Start a Local Service Business New to the Show? Get your personalized money-making playlist here! Sponsors: Airbnb — Discover how much your home could be worth and find a professional co-host today! Mint Mobile — Cut your wireless bill to $15 a month! Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post! OpenPhone — Get 20% off of your first 6 months! Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
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    46 mins
  • 650: 7 Proven Ways to Generate New Business Ideas, with Real-Life Examples

    650: 7 Proven Ways to Generate New Business Ideas, with Real-Life Examples
    Jan 9 2025
    How do you come up with a business idea? Aspiring entrepreneurs often get stuck in the business idea phase — that is, they’re confident they could run a killer business, make a ton of money, and live the good life — if they could only come up with the right idea. If that’s you — the idea seeker — I’ve got good news for you: coming up with new business ideas is actually pretty easy. It’s what comes next that’s hard! But today, let’s go through some of the proven methods you can use to come up with your first (or next) business idea. Full Show Notes: 7 Proven Ways to Generate New Business Ideas, with Real-Life Examples New to the Show? Get your personalized money-making playlist here! Sponsors: Mint Mobile — Cut your wireless bill to $15 a month! Airbnb — Discover how much your home could be worth and find a professional co-host today! OpenPhone — Get 20% off of your first 6 months! Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
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    50 mins
  • 649: This Firefighter’s Side Hustle Grew to $1M in Sales

    649: This Firefighter’s Side Hustle Grew to $1M in Sales
    Jan 2 2025
    Mike Ettenberg spent 10 years as a firefighter, but was constantly losing or breaking his sunglasses on calls. Frustrated, he decided to take matters into his own hands. Frontline Optics makes durable sunglasses for first responders with a no-questions-asked replacement policy. Despite having "no business experience," the Side Hustle Show listener took Frontline from side hustle to full-time venture, selling over $1M worth of sunglasses along the way. Tune in to episode 649 to learn: How Mike found his first customers The "microinfluencer" strategy that generated consistent sales When he felt comfortable quitting his firefighting day job His plans for the future Full Show Notes: This Firefighter's Side Hustle Grew to $1M in Sales New to the Show? Get your personalized money-making playlist here! Sponsors: Mint Mobile — Cut your wireless bill to $15 a month! Airbnb — Discover how much your home could be worth! OpenPhone — Get 20% off of your first 6 months! Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!
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    54 mins