I Asked Listeners for 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

When Meta Deletes a Million Followers Overnight

Bjork from Pinch of Yum and Food Blogger Pro shared the scariest Tuesday of his business: his wife Lindsay’s personal Facebook account got hacked, triggering a Meta rules violation that caused the entire Pinch of Yum Instagram account — 1.1 million followers — to vanish without warning.

The error message simply read that the page didn’t exist.

Despite submitting IDs and following every official appeal step, Meta’s final response was blunt: “This decision is final.”

With no phone number and no human to call, Bjork and Lindsay reached out to their entire network, eventually connecting with a friend who worked at Meta and could file an internal vouching report.

Two reset emails arrived Thursday morning, and the account was restored by that afternoon — about 2.5 days start to finish.

Bjork’s two takeaways:

Clean up any old email addresses tied to your accounts (the breach traced back to a college-era email tied to Lindsay’s profile)
Never stop building owned assets like your email list and website, since a platform can delete your account just as easily as it can shift an algorithm.

When Google Pulls the Rug

Losing 60% of Revenue to a Google Algorithm Update

Jacob Wade from Roadmap Money had just bought a house when a late-2024 Google algorithm update wiped out his freelance writing clients within the same month, cutting his revenue by 60% overnight.

He pivoted into YouTube content, picked up a YouTube client, and clawed back about 40% of the lost income over a few frightening months.

Jacob’s full story and his affiliate marketing strategy for YouTube air in next week’s episode of the Side Hustle Show.

My First-Day Google Slap

Jacob’s story hit close to home. On my very first day of full-time self-employment, I got a similar Google slap, killing roughly 80% of traffic and revenue.

Getting reinstated required about $15,000 in landing page redevelopment and months of uncertainty before Google admitted it had made an error and restored the account.

That same business later got hit by a legislative risk: states pursuing online sales tax revenue pressured retailers to simply stop working with in-state affiliates rather than comply, cutting off affiliate income entirely.

When Your Own Team or Systems Let You Down

Logistics Lies: Don’t Blindly Trust Your Inventory Count

Lana Li of Love Me Like a Robot on Substack trusted her third-party logistics warehouse’s inventory system, which reported 3,000 units left of her bestselling slime/putty product.

The real number was a few hundred. By the time she caught the discrepancy and air-freighted replacement stock from her factory (delayed further after the factory owner suffered a chemical burn), the product arrived around December 11th — missing most of the holiday selling season.

Misprinting 10,000 DVDs

Cheryl from My Memory File Photo Organizing shared a mid-1990s story about ordering 10,000 copies of a stock photography DVD, only to discover a mastering error had made every single copy unusable.

Her company couldn’t cover the reprint cost alone, but the client, trusting the relationship built over time, agreed to split the expense.

Cheryl tightened up SOPs and now triple-checks every project before duplication.

Why Mistakes Can Make You More Relatable

Randall Pulfer had a similar story on the show last year. A shipment of his golf gloves arrived all wrong and couldn’t be sold.

Customers had to wait another 6 to 8 weeks. But Randall shared the story honestly on social media, and he said it earned them a more loyal customer base.

Most mistakes humanize us. When Liz Wilcox had a typo in a subject line, people wrote back that at least they knew it wasn’t AI.

The Scariest Moments Are Sometimes the Ones You Choose

Taking the Leap

Jaron from TrainerMatch left a full-time corporate job to start as an independent personal trainer, skipping the usual step of working at a gym first.

He fought through imposter syndrome by trusting that genuine skill-building creates real value, and by getting in front of the right audience, like asking a gym manager to share his blog post with members.

Thirteen years later, he’s still training and now helps other trainers launch their own businesses.

Walking Away from What’s Working

Corey from Return My Time walked away from a multi-six-figure ARR community business and an eight-figure e-commerce business after nine years in Amazon wholesale, choosing to pivot into AI with no credibility or track record.

About a year later, he’s already doing better than he was in e-commerce.

Corey was previously a guest on the show discussing his Amazon wholesale business in Episode 604.

Shutting Down a Successful Business

Shane Sams, founder of greatmen.org, described the hardest moment of his career: shutting down a successful company with 12 full-time employees and about 20 1099 sales reps because he’d burned out on the CEO life.

He spent three months having difficult conversations and says he broke down after the final layoff call.

Looking back, he says the fear was worse than the reality: “A lot of the scariest things that we go through as an entrepreneur are way scarier in our head than when we actually go do them.”

The Scary Feeling After You’ve “Won”

Justin and Tara Williams, hosts of the Millionaire University podcast and founders of Podcast Collaboration Network, shared two decades of scary moments:

buying houses off courthouse steps sight unseen
borrowing from family to fund early deals
and a night when Tara cried while trying to figure out how to open a credit card just to make payroll.

That same year turned into their first seven-figure year.

Justin’s scariest moment came after they sold their business in 2020 and tried retirement. Months of playing pickleball later, he found himself hit with an unexpected depression: he’d achieved every goal and didn’t know what came next.

That realization led them to start Millionaire University three years ago and, more recently, Podcast Collaboration Network.

Listener Q&A

How do you protect your mental health?

You can’t stop the waves, but you can learn to surf.

What helps me most is minding what Bryan Johnson calls the fundamentals: diet, sleep, and exercise. Am I eating well? Am I getting enough rest? Am I getting a good workout in?

A couple of good days on those can be a powerful reset.

Is rank and rent misleading?

Think of yourself as a marketing service. Testing demand before you build something has plenty of precedent, like Tim Ferriss’s ad tests in The 4-Hour Workweek.

Cody Smith (Episode 555) set out to do rank and rent but ended up doing the pet waste removal work himself.

How can an insurance adjuster sell claims-advice ebooks?

Create Q&A content for people’s moment of need, such as “Should I give a recorded statement?” Lean on your insider credibility.

Partner with body shops and roofers as referral sources. Just watch for conflicts with your employer.

Episode Links

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