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'Shark Tank' investor Barbara Corcoran recalls her 'worst missed investment': 'If only I knew then what I know now!'

"If the sharks did choose to invest, they and I would be rich," says the face-mask entrepreneur.

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Irina Blok of Face Blok on "Shark Tank."
Source: Shark Tank

Everyone has a story about the one that got away: the giant fish that wriggled off the hook, the buzzer-beater that sunk a gambler's long-shot bet, and of course, investing opportunities that would have made the prospective buyer wildly rich.

Sharks are no exception. If you follow New York real estate mogul and "Shark Tank" investor Barbara Corcoran on Instagram or TikTok, you saw the story play out in a recent post in which a masked Corcoran reacts to a "Shark Tank" pitch from 2009 where the entrepreneur pitched designer surgical masks. At the time, Corcoran, along with all the others, passed.

In text on screen, Corcoran calls it her "worst missed investment." And she captions the video: "If only I knew then what I know now!"

The entrepreneur behind the pitch, Irina Blok, has done just fine in the decade following her rejection — she currently works in product design at Google and continues to work on design-based side projects.

Still, that doesn't mean she doesn't feel at least a tinge of regret. "If the sharks did choose to invest, they and I would be rich," she says. "Timing is everything."

Below, Blok shares her advice for aspiring entrepreneurs, especially those who, like her, are perhaps a bit ahead of their time.

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Barbara Corcoran doesn't regret passing on opportunity to invest in face masks

Identify a need for your business

Unable to see into the future, Blok didn't know in 2009 that a pandemic would eventually make face coverings ubiquitous. Creators on Etsy sold more than 12 million masks in April 2020 alone.

At the time, America was in the grips of a smaller scale pandemic, the swine flu. "As a designer I was thinking, 'What can I do to help?'" Blok says. "'What if I take something like a surgical mask and add designs to make it more fun?'"

Blok saw wider applications too, imagining the potential for doctors in children's hospital wards or pediatric dentists wearing quirky designs to inject some levity into a scary situation for kids. "I was looking to bring some humanity to a grim product," she says.

Don't go all in before you're ready

The sharks didn't go for the face masks. FUBU founder Daymond John said it was unlikely masks could become a fashion statement. Fellow investor Robert Herjavec told Blok, "Keep doing it as a side business. Don't quit your day job."

Blok's burgeoning idea was in need of funding. She hadn't sold many masks, her prototypes weren't surgical-grade, and she needed substantial funds to start manufacturing them at a large scale. She had to make a decision to continue to look for funding or bail.

"There's no formula for that. You just kind of have to listen to your heart," she says. "If I was 100% committed to the mask idea, I would have had to quit my day job to get into scaling, manufacturing, and approvals."

For Blok, that wasn't feasible. "I didn't have the luxury to quit my job because I'm a single mother," she says. "It's a combination of how much time and resources you have and what you can and can't do."

Consider moving on to the next thing

None of that is to say that you should give up on your idea at the first sign of resistance. But it's important to be realistic about your options and assess whether your hustle is a true passion. "The most important thing is to listen to your feelings. If you feel committed, continue with the idea and persevere," Blok says. "Another option is to continue creating new things. That's what I did."

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Barbara Corcoran: How your hobby can become a side hustle

You can find Blok's mask designs on her website, though they're not currently for sale. You can, however, shop her line of "Only in Silicon Valley" greeting cards and T-shirts, featuring send-ups of the overworked, overstressed tech crowd. She also does a fair amount of side work for fun and stress relief, posting comics about pandemic life on her social media accounts and featuring a line of "unwelcome" doormats (optical illusions that make it look like a guest may, for instance, fall into a pit of lava) on her website.

"It's lighthearted stuff," Blok says. "No matter what you do, it's important to have fun."

That's why she's not upset about the fact that other folks have been able to profit from selling masks with quirky designs 11 years after she pitched the idea. "I attribute some of the popularity to 'Shark Tank' — a lot of people saw this, and it inspired them to continue this idea," she says. "It's something that helps people, and that's what motivates me. My goal is to create something that solves a problem and makes people's lives better."

And if her next idea doesn't work out or become financially lucrative, Blok won't sweat that either. "The best advice I can give is to keep going and keep creating," she says. "Each idea is like a lottery ticket. The more you buy, the higher chances you have of making a big impact."

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