Entrepreneurs share their big mistakes, and biggest learnings

CHICAGO -- Pretty much, America was built on the simplest of business models: Take someone with a not-done-before or a no-one-does-it-better idea. Let that someone tinker in the back room, or the lab, or the storefront, putting that big idea to work.

CHICAGO -- Pretty much, America was built on the simplest of business models: Take someone with a not-done-before or a no-one-does-it-better idea. Let that someone tinker in the back room, or the lab, or the storefront, putting that big idea to work. Watch it fly -- or flop.

Been that way since way before W.K. Kellogg peddled his toasted corn flakes. Or Henry Ford rolled out his odd four-wheeler, and called it, plainly, Model A.

Oh, wait, that reminds us: Edsel.

Need we say another word?

Fact is, entrepreneurs are the backbone of the economic engine that makes this country churn and soar. Boils down to folks with brains and guts. Or maybe just wild-eyed dreamers who don't believe in No.


We gathered up a flock of American small business success stories, picked the brains behind each tale, found out what they'd term their biggest mistake and most lasting lesson.

Listen in.


Thousands of pounds of Early Glow strawberries ago, back in the late 1970s, Justin Rashid was a lifelong wild-food forager from Northern Michigan who'd tried his hand at New York City theater, but went racing back to the woodlands he knew inside out. He was busy picking black morels when he met up with Larry Forgione, a New York City chef.

Wasn't long till Forgione, who'd set his sights on bringing the finest indigenous American foods to the plate, and Rashid, who basically wanted an excuse to poke around the woods every single day, decided they'd cook up the best fruit preserves in the world.

Thus was born, in 1982, American Spoon, an artisanal specialty food company based in Petoskey, Mich. Rashid and Forgione started out with two copper kettles in the basement of a candy shop, and now cook up a line of 100 award-winning spoon fruits, preserves and salsas (to skim the list); count 50 year-round employees; and sell through six retail shops, a mail-order catalog and Web site (

Question: What was your biggest mistake?

Answer: Becoming too invested in a particular market outside your control. From 1993 to 2001, we grew in supplying to food service. We had a couple million (dollars) in sales, supplying first-class and business-class to six airlines. After 9/11, they all canceled our orders and almost took us down.


Q: Biggest thing you've learned?

A: Taking calculated risks thins out the competition. Because, although there are tons out there who will try to steal or copy your ideas, putting money on the table makes all those who are chasing you paralyzed. In the meantime, you can break away.



Maggie Wynja got into the furniture business because she couldn't get enough of Colonial Williamsburg. And from Ames, in the heart of Iowa, that involved a lot of driving.

So she up and opened a shop on Ames' Main Street. A 600-square-foot rented space. Called it American Country Home Store. At first, she was an authorized dealer for Yield House, a mail-order kit-furniture company that had been around for decades. But even before Yield House closed up shop (it no longer manufactures but former dealers can still offer merchandise from its warehouse), Wynja was broadening her wares, adding rugs, wicker and French bistro furniture to the Americana mix.

She leapt on the Internet back in 2000, one of the only shops in downtown Ames to take up a fellow businessman's offer to construct a Web site. And today, she sells coast-to-coast, but still with that down-home-Iowa personal touch that makes a shopper feel as if she's just ambled in off Main Street.

Q: Biggest mistake?


A: Money's the big thing. It takes so much more than you ever think. It's like, "Oh, I'll just open (up shop) and sell $500 worth of product, and put $250 in my pocket." You get in over your head very fast.

Q: Most important thing you've learned?

A: Change with the times. Keep up with technology. We started our Web site when many brick-and-mortar stores were reluctant. We just signed up to have our catalog featured as an app with iPad users (, the first interactive catalogs for the iPad.



It's all about paper and paste -- cutting and pasting paper, precisely. It's called decoupage, an art with roots in ancient Siberian tombs, and one that in 18th-century Europe was all the rage.

John Derian, a decoupage artist with a cult following these days, has made it a whopping business for the last two decades.

His wares -- plates, vases, trays, paperweights, cachepots -- are sold out of his very own quirky retail shops, two in New York City, and a seasonal boutique in Provincetown, Mass. But you can find them, too, around the country at some 400 high-end boutiques and department stores, among them Saks Fifth Avenue, Neiman Marcus and Bergdorf Goodman. Then there's Target, which peddles Derian's signature accessories collection, and thus brings it to the masses.


"I'm passionate about anything created by hand and in sharing those with people who are captivated by artisans and their work," says Derian, a Boston-area native. He works with a small atelier of artists, using color reprints of 18th- and 19th-century images, and piecing them together under glass.

Q: Biggest mistake?

A: I can't really think of any one mistake. It was years of trial and error.

Q: What's the most important thing you've learned?

A: Basically, I've just been very focused on making things. I didn't look up the first 15 years. I've been very lucky. I have always made things, and then in my 20s, I just started selling them. I haven't had an "aha" moment; I feel good about all that I do.



Safari Surf School was formed by Tim Marsh and his brother Tyler in 2000. It's located in Nosara, Costa Rica, on the Pacific side of the country, and offers all-inclusive packages for individuals, couples, families and groups to learn how to surf while experiencing the culture and beauty of Costa Rica.


Q: What was your biggest mistake when you started the business?

A: Not having a proper back-end system to compile my database of clients.

Q: What is the most important thing you've learned?

A: Customer service is the only thing that matters in any type of business. It is the customers who pay your and your staff's salary, so you are working for them. Their review of your business in the new social media world is worth gold. Take excellent care of your customers and care about your customers. Make sure they are enjoying your product to the fullest. Bring them into your "family" and make them feel there is no other place they would rather be than with your company.



Social media has been very generous to Gary Vaynerchuk. It pumped his New Jersey wine shop up to over $60 million in business a year, turned him into an internationally known authority on both wine and social media, made his daily webcast, "The Thunder Show," on a must-watch for more than 90,000 "winos" a day, beamed his "Wine & Web" show onto Sirius satellite radio, spawned a social media consulting firm, and led to a seven-figure, 10-book deal. His next work, "The Thank You Economy" (Harper Business $24.99), shows how companies can succeed over rivals by outperforming, outserving and, yes, outloving customers using the Internet, social media and other platforms. The book is scheduled to be released in March.

Q: What was your biggest mistake?


A: I have too big of an appetite and my eyes are too big. I'm always trying to "eat" more than I can eat. I try to take on more than I can execute. I'd say sometimes just having big eyes has cost me. If I ever drop the ball though, I'll come through tenfold to make up for any mistakes.

Q: The most important thing you've learned through experience.

A: Well, I don't read, so everything. I think experience allows you to be more comfortable. I wasn't a big reader or student so everything I did was based on intuition. Everything was a learning experience. The reason I have big eyes is because I like to experience things because once I taste something, I know the flavor.

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