Side Hustle Hero

Joan Posivy
  • 5.0 (18)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

Side Hustle Hero is the podcast for everyone who wants to build the courage, confidence, and drive to launch, persevere, and succeed at creating a source of income beyond their regular job. Each episode is crafted with the goal of having you take action and win. You'll hear insights from experienced side hustle heroes who share what's worked and what hasn't so you can execute smarter and for more profit. Hosted by Joan Posivy, bestselling author of The Way Success Works, How to Decide, Believe & Begin To Live Your Best Life. Listen online https://www.sidehustlehero.com/ Connect with Joan https://www.joanposivy.com/

  1. 4D AGO

    How One Connection Can Build Your Client Pipeline

    Finding clients can take more time than actually doing the work, especially when you are building a side hustle alongside a full time job. But what if you could bring opportunities to you instead of constantly chasing them? Today Megan Leasher explains how she built a client pipeline by positioning herself inside existing ecosystems instead of relying on traditional outreach. Instead of hunting for clients, she focuses on partnerships, visibility, and strategic positioning that bring opportunities directly to her. She also shares how she structured things with her employer so her side hustle and full time role can coexist smoothly, along with practical steps you can take this week to start building your own pipeline. In this episode, you will learn: The three ways she consistently gets clients without chasing them How contractor pools and partner firms can become built in lead sources Why smaller firms can be powerful allies for growing your client base Low cost and no cost ways to build credibility and visibility How speaking, writing, and communities can act as referral engines What to know about joining a Forbes advisory council and whether it is worth it Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/184 Connect with Megan: LinkedIn Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

    41 min

  2. FEB 10

    How to Finally Follow Through on a Side Hustle

    If you've been thinking about starting or growing a side hustle but haven't yet followed through, you'll want to check out this episode. Here I share a simple two-step accountability process I've used myself many times to move from talking about taking action, to actually doing it. I walk you through; how I create forward progress, why keeping your word matters so much, and how this approach helps you actually stay in motion on your side hustle without overcomplicating things or getting stuck in planning mode. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/183 Be on the show! https://www.sidehustlehero.com/guests/intake/

    10 min

  3. FEB 3

    How a Tour Guide Side Hustle Grew Into a $600K Business

    How do you turn a tour guide side hustle into a $600K local business in under three years? Paul Whitten shares the real strategies behind growing a simple weekend hustle into a high-margin tour company, by starting with just $3,600 and scaling through smart pricing, partnerships, and consistent customer demand. In this episode, you'll learn: How Paul attracted his first customers with no marketing budget Why Google reviews and platforms like TripAdvisor became growth engines The upselling approach that increased revenue without sounding salesy How private and corporate events boosted profits Ways to turn one service into multiple revenue streams If you're building a side hustle, or thinking about starting one, this episode shows what's possible when you dream big, have a vision, and are willing to put in the work. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/182 Connect with Paul: Nashville Adventures website Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

    52 min

  4. JAN 27

    Why We Struggle to Delegate (and How to Fix It)

    Delegating is one of the hardest skills for side hustle owners to master, especially when you care deeply about your business and want everything done right. Today Renee Hastings shares why fear, perfectionism, and trust issues often stop entrepreneurs from letting go, even when they know it's holding them back. You'll learn: What tasks make sense to delegate first  How to set clear expectations so things don't fall apart Common mistakes that can derail the process If you've ever felt overwhelmed trying to do everything yourself, this conversation will help you start building a side hustle that can actually grow. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/181 Connect with Renee: Executive Help Now website Renee's LinkedIn Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

    22 min

  5. JAN 20

    Why Side Hustles Are Becoming a Normal Part of Professional Life

    Side hustles are no longer just about earning extra money. For many professionals, they've become a strategic part of modern career planning. Here we break down why side hustles are becoming a normal part of professional life. We look at how building something alongside your career can help you stay relevant, build real assets, and create options beyond a single employer. We walk through five reasons forward-thinking professionals are choosing to build side hustles intentionally. They can: Keep professional skills current, relevant, and adaptable Allow you to build assets you actually own Increase credibility and professional respectability Create a portable network that stays with you over time Provide leverage, flexibility, and long-term security This episode will help you take a more deliberate approach to building a side hustle, not as a hobby or a backup plan, but as a smart extension of your career. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/180 Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

    16 min

  6. JAN 13

    Be Willing to Fail in Public (or You'll Never Start)

    Most people don't fail because they lack ideas, talent, or motivation. They stall because they're waiting to feel ready. In this episode, I revisit a powerful conversation from the very beginning of the Side Hustle Hero podcast with my first-ever guest, Joel Young. It opens with a simple but uncomfortable truth: you don't really grow until you're willing to fail ... in front of other people. Joel shares how he got started recording voiceovers in his closet with almost no experience, no studio, and no certainty about where it would lead. That willingness to start before he felt ready eventually helped him become one of Fiverr's all-time top earners, with $2.7 million in earnings at the time of our interview. In this conversation, we talk about: why waiting for confidence keeps most people stuck why practicing in private only gets you so far how starting before you feel ready builds real skill how reframing what you think of as "giving something up" can make working on a side hustle feel more empowering If you've been holding back because you don't want to look foolish, make mistakes, or put yourself out there before you feel ready, this conversation will help you rethink what it really takes to get started. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/179 Connect with Joel: Joel's Main Site JumpStart Video Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

    19 min

  7. JAN 6

    Top 10 Side Hustles To Start In 2026

    Most "top 10 side hustle" lists recycle the same ideas with very little context. This episode takes a different approach. These 10 side hustles are drawn from real conversations with guests who are actually doing the work. Some are simple and inexpensive to start. Others require more capital or coordination. None are ranked, because the right side hustle depends on your situation and circumstances. The list includes mystery shopping, selling at farmers markets, printables, online courses, virtual assistant work, AI workflow consulting, fundraising, direct mail postcards, high-ticket dropshipping, and luxury restroom trailers. The focus is on what's working heading into 2026, what often flies under the radar, and how people are building income without chasing hype. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/178 Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

    21 min

  8. 12/30/2025

    Why Most People Quit Their Side Hustle

    Why do so many people quit their side hustle, even when the idea itself isn't bad? Today I break down 3 real reasons most people walk away from their side hustle and why quitting is often more about behaviour than talent, motivation, or market demand. If you've ever started a side hustle, put in the effort, and then stopped (especially when the money didn't show up as quickly as you hoped,)  you're not alone. You'll learn: Why early income is a lagging indicator, not a verdict on your idea The three most common reasons people quit too soon How starting too big actually works against you Why lack of clarity around progress creates unnecessary doubt How isolation sabotages follow-through What to do differently next time so quitting isn't the default response This isn't about pushing harder or working longer hours. It's about setting yourself up with the right expectations, structure, and support so your side hustle has a real chance to grow. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/177  Share this with someone who's tried before and is thinking about giving it another shot. Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

    14 min
See All (184)

Trailer

5
out of 5
18 Ratings

About

Side Hustle Hero is the podcast for everyone who wants to build the courage, confidence, and drive to launch, persevere, and succeed at creating a source of income beyond their regular job. Each episode is crafted with the goal of having you take action and win. You'll hear insights from experienced side hustle heroes who share what's worked and what hasn't so you can execute smarter and for more profit. Hosted by Joan Posivy, bestselling author of The Way Success Works, How to Decide, Believe & Begin To Live Your Best Life. Listen online https://www.sidehustlehero.com/ Connect with Joan https://www.joanposivy.com/

Information

  • Creator
    Joan Posivy
  • Years Active
    2022 - 2026
  • Episodes
    184
  • Rating
    Clean
  • Copyright
    © 2023
  • Show Website
    Side Hustle Hero

You Might Also Like