How to Overcome Fear of Failure in Your Short-Term Rental Business: 4 Lessons From Sara Blakely

The fastest way to overcome fear of failure in your short-term rental business is to redefine what failure actually means — not a bad outcome, but not trying at all. That single shift is what built a billion-dollar company out of a pair of cut-off pantyhose.

For seven years, Sara Blakely sold fax machines door to door. She got kicked out of buildings. People ripped up her business card in front of her face.

Then she took $5,000 of her own savings, cut the feet off a pair of pantyhose, and started a company called Spanx. She never took a single dollar from an investor. Twenty-one years later, that company was valued at $1.2 billion — and because she’d never given any of it away, the payoff was entirely hers.

The real secret wasn’t the pantyhose. It was a question her dad asked at the dinner table every week — one that rewired how she thought about failure. Here’s her playbook, and what it means for your rental business.

Key Takeaways

• A rental business with zero failed experiments isn’t safe. It’s stuck — failure means not trying, not a bad outcome.
• Every “no” from a property owner is a rep, not a rejection, and reps compound into skill.
• Building conviction from your own data protects a new idea before it’s strong enough to survive other people’s opinions.
• Growth you don’t own isn’t the flex it looks like. Patience and ownership are what make the eventual payoff yours.
• Better decisions come from evidence, not from crowdsourcing your dream to people who’ve never built anything.

Want to go deeper? Watch the full YouTube video to discover how Sara Blakely’s approach to failure can help you take smarter risks and move your short-term rental business forward: Watch the full video here

Why Fear of Failure Quietly Stalls Most Rental Businesses

Most hosts don’t think of themselves as afraid of failure. They think of themselves as careful.

Never raise the rate, because what if bookings dip. Never pitch the owner, because what if they say no. Never try the new amenity or the direct booking push, because what if it doesn’t work.

But a business with zero failed experiments isn’t actually a safe business. It’s a stuck one. Sara Blakely’s story reframes exactly why — and gives you a weekly practice to break the pattern.

Lesson 1: Redefine Failure — The Dinner-Table Question

Every week, Sara’s dad asked her and her brother one question: “What did you fail at this week?” Not what grade she got. Not whether she won. In the Blakely house, failure didn’t mean the outcome went wrong. It meant she didn’t try.

Sara failed the LSAT twice. Law school, gone. She worked at Disney World. She sold fax machines. None of it felt like a straight line at the time. But every attempt was a win at that dinner table, because the trying was the point.

How Do You Overcome Fear of Failure as a Short-Term Rental Host?

You overcome fear of failure as a short-term rental host by redefining what counts as failure in the first place. Most hosts unconsciously define failure as a bad outcome — a rate increase that doesn’t book, a pitch to a property owner that gets rejected, a new amenity guests don’t use. That definition makes every experiment feel risky, so hosts stop experimenting altogether. 

A more useful definition, borrowed from Sara Blakely’s family dinner table, treats failure as not trying at all. Under that definition, a rate test that doesn’t book isn’t a failure — it’s information. The practical fix is a weekly ritual: at the end of each week, write down what you tried that could have gone wrong. If the honest answer is nothing, that’s the actual problem, not a quiet win.

Steal the ritual. Every week, write down what you failed at. If your honest answer is “nothing,” that’s not a good week — that’s a week you didn’t swing. Pick this week’s swing: raise a rate on your strongest weekend, message a past guest about booking direct, or test a new hero photo.

Lesson 2: Rejection Is Reps

Seven years of cold doors and ripped-up business cards built the saleswoman before the idea ever arrived. By the time Spanx showed up, Sara had already risen to national sales trainer — the skill the idea needed most was already built.

If you’re co-hosting, or want to be, the number one thing that stops most women isn’t skill. It’s the fear of pitching a property owner and hearing no. But every no is a rep. Every owner conversation makes the next one smoother. Every objection you hear once, you’ll have an answer for twice.

Set a rep goal this month — a number of owner conversations, not a number of wins. After every no, write down the objection you heard. Add a “swings taken” line to your weekly business review, so you’re tracking attempts, not just outcomes.

If you’re ready to start or grow a profitable co-hosting business, grab your copy of The Co-Host Code. This step-by-step guide will help you confidently find and sign property owners, price your services, put the right contracts and systems in place, and build a co-hosting business that’s designed to grow—without all the guesswork.

 

Lesson 3: Protect the Idea, Then Bet on Yourself

Sara kept the Spanx idea a secret for a full year. Her reasoning: ideas are the most vulnerable in the moment you have them. When she finally shared it, her own family asked why nobody had done it already — and if she’d heard that on day one, before she had any conviction, the idea might have died at the kitchen table.

If you’re in the early season of your rental dream, don’t crowdsource it too soon. When you announce plans before you’ve built conviction, you’re not gathering information. You’re gathering opinions. And opinions are drama.

Run the actual numbers on the market and the deal. Write the three data points that tell you this can work, and let evidence make the call. Where you can, be resourceful — furnish creatively and learn the tools yourself. Resourcefulness compounds.

Lesson 4: Ownership Pays Patience

Spanx was profitable almost from the start. Sara could have taken investor money and grown three times faster — everyone told her to. Instead, she grew the company from its own revenue, at its own pace, for twenty-one years. When a $1.2 billion valuation finally came, she still owned a hundred percent of the company.

There’s enormous pressure in this industry to grow fast — partners on every deal, leverage to the eyeballs, five properties by next year or you’re behind. But growth you don’t own isn’t the flex it looks like. One property that cash flows, that you control, growing at the speed of your own profits, can be worth more to your life than five properties carrying five partners and a mountain of stress.

Audit your growth pressure: are you expanding because your numbers say so, or because you think you need to? Write down what you actually own today — property equity, brand, guest list, systems. That list is your real net worth as a host.

Frequently Asked Questions

How do I get over the fear of pitching property owners for co-hosting?

Reframe every pitch as a rep, not a make-or-break moment. Set a monthly goal for the number of conversations you have, not the number of yeses. Each no teaches you the objection you’ll be ready for next time, so the skill compounds even when an individual pitch doesn’t land.

Should I tell friends and family about my rental business plans before I’ve run the numbers?

Not yet. Build conviction from your own data first — market research, deal analysis, real criteria. Sharing an unproven idea too early invites opinions from people without real information, which can talk you out of something the numbers would have actually supported.

How do I know if I’m growing my rental business too fast?

Ask whether your expansion is following your actual profits and booking data, or whether it’s following pressure to keep up with other hosts. Growth funded by partners or heavy leverage can cost more in stress and lost ownership than it looks like it’s worth on paper.

What if I haven’t failed at anything in my rental business lately?

That’s the flag, not the reassurance. A week with nothing to report usually means you didn’t try anything new — not that everything is running perfectly. Use it as a prompt to take one small, calculated risk this week.

Is it better to grow a short-term rental business with investors or bootstrap it?

There’s no universal answer, and both paths have real tradeoffs. Investors can accelerate growth, but they also mean sharing the eventual payoff. Bootstrapping is slower, but every dollar of the outcome stays yours. The right choice depends on your goals, your risk tolerance, and the specific numbers in front of you.

How many “no” conversations should I expect before landing a co-hosting client?

There’s no fixed number, and it varies by market and pitch. What matters more than the number is treating each no as training rather than proof you’re not cut out for it. Tracking your attempts, not just your wins, keeps you moving instead of stalling after the first rejection.

What does it actually mean to “own” your short-term rental business?

Ownership means holding the equity, the brand, the guest relationships, and the systems that make the business run — not just having your name on a listing. A property that’s heavily leveraged or dependent on partners can still be technically yours while giving away most of the eventual payoff.

Final Thoughts

Seven years of slammed doors. Five thousand dollars. Twenty-one years of patience. And a payday big enough to hand every employee first-class tickets anywhere in the world. Nobody handed Sara Blakely anything. She bet on herself.

What did you actually try this week — not just what worked, but what you were willing to risk not working? Are you building conviction from your own numbers, or letting other people’s opinions make the call for you? And is the growth you’re chasing something you’ll actually own, or something you’re quietly giving away one partner at a time?

You don’t have to answer those questions alone. That’s exactly why I built the STR Sisterhood — a place to bring your real swings, your real setbacks, and your real next decision, and get honest feedback from women who’ve taken the same risks already. Learn more about the STR Sisterhood here.