
767: Listeners Share Their Scariest Entrepreneurial Moments
What’s the scariest moment you’ve faced as an entrepreneur? For Halloween, I asked Side Hustle Show listeners to share theirs. You’ll hear about a 1.1 million-follower Instagram account deleted overnight, a Google update that wiped out 60% of one freelancer’s income, a warehouse that miscounted inventory right before the holidays, and 10,000 unusable DVDs. You’ll also hear from entrepreneurs who chose to be scared: quitting a job, walking away from an eight-figure business, and laying off a team they loved. I’ll share a few of my own along the way, including a Google ad ban on my first day of full-time self-employment, a ladder crash from my house-painting days, and a Bitcoin ransom email that came from my own address. Tune in to Episode 767 of the Side Hustle Show to learn: how platform risk (Meta, Google, logistics partners) can wipe out revenue or an entire following overnight, and what to do when it happens why owning your audience through email and your own website matters more than ever how entrepreneurs recovered from lost accounts, blown inventory, costly mistakes, and layoffs — and what they'd do differently Full Show Notes: Listeners Share Their Scariest Entrepreneurial Moments New to the Show? Get your personalized money-making playlist here! Sponsors: Freshbooks.com – Get 90% off your first 4 months! Shopify — Sign up for a $1 per month trial! Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses! Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post! Monarch — Get an extended 30-day free trial! About The Side Hustle Show This is the entrepreneurship podcast you can actually apply! The award-winning small business show covers the best side hustles and side hustle ideas. We share how to start a business and make money online and offline, including online business, side gigs, freelancing, marketing, sales funnels, investing, and much more. Join 100,000+ listeners and get legit business ideas and passive income strategies straight to your earbuds. No BS, just actionable tips on how to start and grow your side hustle. Hosted by Nick Loper of Side Hustle Nation.











