Launching and maintaining a side project can be difficult. There are a lot of ups and downs, roadblocks, questions, and countless little details you didn’t know you’d encounter when you started out. The good news: an entire network of multi-hyphenates on Polywork and beyond are in the trenches with you. The even better news: many of these people who have paved the path before you have shared their stories, expertise, and advice on podcasts.
Here are five of our favorite podcasts to help inspire and instruct you as you launch and run your side business.
1. Freelance to Founder
The lowdown: Hosted by two former freelancers, Preston Lee and Clay Mosley, who have grown their endeavors into six- and seven-figure businesses, Freelance to Founder is a call-in show where real-life freelancers can ask their questions and get advice on how to grow their businesses.
Who it’s for: Freelancers who, well, want to be founders or anyone looking to grow a side project into a larger-scale company.
Why you should listen: Remember in high school when the teacher would say: “Don’t be afraid to ask a question, because chances are, someone else is probably wondering the same thing”? That statement truly embodies the ethos of this podcast. Each episode feels like a taped coaching session, where guests call or write in their questions and concerns, and the hosts walk them through practical solutions and advice. If you have questions about how to run a small business, this is a great resource.
Why you might skip it: Every episode muses on a specific question that you may or may not need an answer to. Maybe you already have an established business model, system for your taxes, process for invoices, or marketing strategy. Take what you need and leave the rest.
2. Side Hustle Pro
The lowdown: In this podcast, digital marketer-turned-entrepreneur Nicaila Matthews Okome interviews Black women founders, sharing how each guest transformed their side hustles into full fledged businesses.
Who it’s for: People with an idea or a passion, looking for the inspiration to take it a step further.
Why you should listen: Every episode is a deep dive into an individual business and its creator, allowing the listener to follow one endeavor—and one compelling narrative— from start to finish. Its approach to storytelling can be really inspirational for anyone who needs a little encouragement.
Why you might skip it: This podcast features guests from a wide range of fields, such as beauty, tech, fashion, wellness, finance, and real estate. It’s entertaining and inspirational to hear about them all, but might not always be applicable to your specific side project.
3. Equity
The lowdown: From TechCrunch—a tech-centric news source behind a handful of other popular podcasts including Found, Chain Reaction, and TechCrunch News—Equity digs into the week’s tech industry headlines, analyzing the implications for start-ups.
Who it’s for: Tech entrepreneurs interested in staying up-to-date on what’s going on in the world of tech.
Why you should listen: No matter where you are in your side project’s lifespan, it’s important to understand your industry, including widespread trends and what other companies are doing. Staying abreast on the goings-on can help you understand where your own project fits into the grand scheme of things.
Why you might skip it: Industry news can be interesting and helpful in a macro sense, but it won’t help you run your business better from a practical day-to-day perspective. Also, if you’re not interested in tech, this podcast is not for you.
4. The How of Business
The lowdown: Entrepreneur and small business coach Henry Lopez guides listeners through practical steps that are required to operate a business. Episodes include topics like how to create an LLC, manage cash flow, hire employees, hone communication, and thoughtfully grow your company.
Who it’s for: Anyone who has questions about the nitty gritty of running a small business.
Why you should listen: As the name suggests, this podcast focuses on tips, tricks, and how-to’s. It’s a manual, full of actionable steps from people who have done it before, packaged in digestible and easy-to-listen-to episodes.
Why you might skip it: Since each episode is tailored to a very specific problem or skill, you can think of this podcast as an à la carte menu at a restaurant: Pick the episodes that are useful to you and skip the ones that aren’t. Or skip the podcast altogether if you’ve already got the basics of your business covered.
While these are some of our favorite side hustle-centric podcasts, they’re far from the only podcasts out there. As of summer 2023, there are more than 4 million registered podcasts worldwide—and by some counts, “business” is the fourth largest genre, so there are plenty to choose from. Find a podcast whose host, format, topics, and tone, speak to you and your unique endeavor.
5. How I Built This
The lowdown: On this NPR podcast, host Guy Raz interviews the founders of major brands such as Airbnb, Halo Top Ice Cream, and Spanx, illuminating each of the entrepreneur’s paths to success.
Who it’s for: Big dreamers who foresee their side project evolving into the next Fortune 500 company, plus anyone who finds inspiration in the great entrepreneurial stories of our day.
Why you should listen: Manifestation can be a powerful tool, and hearing stories about the obstacles these founders faced on the path to success can be really encouraging in the early stages and difficult stretches of your own side business journey. Plus, it’s a long-running podcast with new episodes released every few days, so you won’t run out of listening material.
Why you might skip it: While entertaining and often helpful, hearing the grand, how-we-got-here stories from successful founders can feel unrealistic at times. This tends to be exposed in episodes where co-founders met in MBA programs at Ivy League business schools, a path that is not available to everyone.
If you’re focusing on the everyday logistics to building your side project and want to learn more about practical how-to’s rather than overarching storylines, this podcast might not be for you.
