Successful Entrepreneurs Reveal How to Face Failure With Grace and Grit
Failure is a natural part of life. So, if you ever hope to succeed at anything, learning how to deal with it is critical.
Few understand this better than entrepreneurs, who practically make a career out of failing until they hit that one big break that changes everything.
But if you’re an entrepreneur, you already know this, right? Unfortunately, that doesn’t make it any easier to deal with. For that, you need to turn to the insights and wisdom of the successful business leaders who have come before you.
Success is not final, failure is not fatal: it is the courage to continue that counts.
So, what do some of the most successful entrepreneurs in the world say about dealing with failure? You’re about to find out.
1. Use rejection as a springboard – Airbnb co-founder Brian Chesky
Valued at over 30 billion dollars, Airbnb is one of the single most successful startups to ever come out of Silicon Valley. And that’s saying a lot.
However, before Airbnb exploded in popularity– to the point of becoming a household name– co-founders Brian Chesky, Joe Gebbia, and Nathan Blecharczyk got through their own fair share of failure.
Here is what Chesky wrote in a 2015 piece on Medium:
“On June 26, 2008, our friend Michael Seibel introduced us to seven prominent investors in Silicon Valley. We were attempting to raise $150,000 at a $1.5M valuation. That means for $150,000 you could have bought 10 percent of Airbnb."
"Below you will see five rejections. The other two did not reply...The investors that rejected us were smart people, and I am sure we didn’t look very impressive at the time.”
2. Develop a thick skin – RYOT CEO and co-founder Bryn Mooser
Bryn Mooser, co-founder and CEO of booming virtual reality studio RYOT, says you need to develop thick skin to deal with inevitable bumps in the road and unexpected setbacks:
"I think you have to have an incredibly thick skin...You have to be really passionate. And you have to fail a lot — and when you fail, you have to pick yourself up and learn and change and adjust."
3. Use reminders to maintain an optimistic attitude – Sighted founder Murray Newlands
Murray Newlands, founder of the online invoicing company Sighted founder, understands how draining entrepreneurship can be, but says that looking anywhere outside of yourself is a mistake:
“It’s so easy as an entrepreneur to get sucked into feeling exhausted or frustrated, and often the blame is yours alone,” writes Newlands, “But a negative mindset sucks up mental bandwidth and energy that you need to stay focused and successful.”
"Whenever you see a quote or a picture that helps you stay positive, place it front and center so you can remember what this journey is all about.”
4. Use failure as motivation to do better – Billionaire investor Mark Cuban
In an interview with Bloomberg, Dallas Mavericks owner and Shark Tank co-star Mark Cuban gave insight into how he views failure and how to respond to it productively:
“Every one of my companies, whether something I started or something I invested in, is a scoreboard. How am I doing? A lot of investors or advisers play it as a numbers game.”
“If they invest in 20 companies, as long as one success covers 19 losses, they did OK. I look at every loss as a huge failure. I had an investment go bad recently. I lost $1.5 million on it. It pisses me off to no end."
He goes on to say that, instead of letting failure get you down, if you can respond to it more constructively with the right questions, you can turn a loss into a gain:
"You can also use it as motivation. What did I do wrong? Who did I trust that I shouldn’t trust? What can I learn from this situation so I can avoid it next time?”
5. See failure as the beginning of great success – The Corcoran Group founder Barbara Corcoran
Fellow Shark Tank co-star and founder of New York’s most prominent real estate firm Barbara Corcoran doesn’t just see failure as something which needs to be overcome, she’s shifted her whole perspective about it:
“All of my best successes came on the heels of a failure, so I’ve learned to look at each belly flop as the beginning of something good,”
“If you just hang in there, you’ll find that something is right around the corner. It’s that belief that keeps me motivated. I’ve learned not to feel sorry for myself, ever. Just five minutes of feeling sorry for yourself takes your power away and makes you unable to see the next opportunity.”
Military Dad Defends His 4 Little Daughters When Strangers Make This Rude Remark
Military Dad of 4 Daughters Defends His Girls When Strangers Make This Rude Remark
Austin von Letkemann is the military officer strangers feel "sorry" for — and the reason is infuriating.
Whenever the devoted father leaves the house with his four children, strangers can't help but notice the officer in uniform is holding hands with 4 adorable little girls. They will tell the traditionally "masculine" and "all American" dad they feel sorry for him, because he has no sons. This dad makes one thing very clear: They are his daughters, they aren't a burden.
In a passionate video, von Letkemann took to Instagram to share with his followers that the only thing that's "difficult" about being a girl dad — is clapping back to these sexist remarks over and over again.
They Mock His Daughters To Their Face
When strangers approach Austin von Letkemann and his four daughters, they don't always realize that their comments are being overheard. They seem oblivious to the fact that his girls understand every word. Von Letkemann describes how people will approach him and, without thinking, make remarks like "I'm sorry" or even joke about his lack of sons. What they don't realize is that these comments, intended to be light-hearted or humorous, can be deeply hurtful to his daughters. These strangers are not just disrespecting von Letkemann's choices as a father; they're also sending a message to his daughters that their presence is something to be pitied. It’s a message that von Letkemann won't stand for, and he's speaking out to defend his girls from these insensitive remarksSaying "Get Your Shotgun" Isn't Funny — It's Sexist
Another common comment that Austin von Letkemann encounters is the old "better get your shotgun ready" trope, often delivered with a smirk or a wink. This line is typically intended to suggest that a father with daughters should be on high alert to protect them from potential "suitors," implying that they are objects to be guarded rather than individuals with agency.
Von Letkemann finds this line of thinking outdated and sexist. In his viral Instagram video, he points out that these jokes are not just stale — they're damaging.
By suggesting that his daughters require armed protection, the joke reinforces the idea that women are inherently vulnerable and need to be shielded from men. Von Letkemann argues that instead of promoting this narrative, society should focus on teaching respect and consent, challenging these sexist tropes at their source.
Watch Austin von Letkemann's Video:
"If I Had A Fifth Child, I'd HOPE It Was A Girl" — One Dad's Message For Other Parents
Despite the constant remarks about his lack of sons, Austin von Letkemann is clear: He wouldn't trade his daughters for anything.
In fact, he told his Instagram followers that if he were to have a fifth child, he would hope for another girl. This declaration isn't just about doubling down on his pride in his family — it's a pointed response to those who see fathering daughters as a misfortune.
Von Letkemann's stance is a powerful one, rejecting the notion that a family is incomplete without sons. He encourages others to question the assumptions behind these comments and to appreciate the joy and fulfillment that his daughters bring. By sharing his story, von Letkemann hopes to create a more inclusive perspective on fatherhood, one that values daughters just as much as sons.