My Luckiest Moment as an EntrepreneurFor entrepreneurs, luck is a lot like snowflakes – no two instances of it are alike. Today, we’ve got a panel of small business owners on our blog who have experienced some seriously serendipitous moments with their companies. From signing a deal while at the zoo to feeding Bradley Cooper and Ryan Gosling and plenty of appearances on ABC’s Shark Tank in between, these 45 entrepreneurs prove that everything in life is luck!

1. “Speaking internationally selling marketing training at live seminars, my luckiest moment was with a small group of 23. At the end of the 3 hour training, 21 attendees purchased additional training for $497.00 making it the highest converting training I have given.”

– Nathan Amaral, Owner/CEO, Nathan Amaral International

2. “My luckiest moment came when I least expected it. I was struggling with my bills, because I quit my job several months before to start my own web design company and it didn’t go so well. It was really hard to keep myself motivated, but then the first client appeared from nowhere basically. Till this day, I have no idea how he then managed to find my half-baked website and make a purchase. From that moment on, everything just got better and better!”

– John Perry, Owner, Muse Templates Pro Company

3. “A couple of years after I started my company I had pitched a CEO about a month before I ran into her at a networking event where she was the keynote speaker and her topic was about being a woman leader in a traditionally male-dominated business. I had followed up after sending my proposal several times via e-mail and voicemail but the CEO never returned any of my messages or even acknowledged the receipt of the proposal requested. You can imagine my shock when she announced at this event as part of her speech that she believes it is important to put your money where your mouth is and for women CEO’s to support other respected, well-run women’s businesses and that is why she has hired my firm to handle all her company’s marketing and PR! Everyone congratulated me after – it was a better endorsement than an ad in the New York Times because she was very well known and had the reputation of being very tough with high standards so I got a LOT of business from people in the room that night because they thought if I was able to impress her, I must be very good! For a young company, it was a big moment.”

– Paige Arnof-Fenn, Founder & CEO, Mavens & Moguls

4. “My lucky moment was when I quit my job to start MyBeautyCompare. I did some extensive research and noticed that there was a gap in the market for MyBeautyCompare, as it is the first of its kind. Women these days are too busy and overwhelmed with too many choices when deciding which beauty products to buy. MyBeautyCompare takes the guessing out of the shopping – it’s like for beauty.”

– Nidhima Kohli, CEO & Founder, MyBeautyCompare

5. “My luckiest moment was calling the precise day of the stock market bottom on March 9th, 2009 and publishing an newsletter on that day (and investing a lot around that time)!”

– Mark Daniel Elliott, President, Elliott Asset Management

6. “In 2010 my wife and I both quit our jobs to run the shopping deals website, setting it up for under $500. With no previous experience in running a website full time, we faced stiff competition from big established names in the industry, however the timing proved just right with the UK economy suffering and many more consumers looking to save more money when shopping online. Since then we have helped over half a million people through our site and have expanded the business into the Australian market.”

– Andrew Firth, Director, Red League Media Ltd.

7. “The luckiest moment for me as a business owner occurred just after retiring from the United States Air Force. I accepted a job with a contracting firm, but knew it was not my passion. Inspiring people was my biggest passion, so I became a part-time speaker. One day after delivering a speech to an association, I made up my mind to become a full-time public speaker. I returned to work the following week and resigned, and one of the people I told I was a public speaker to contacted me for lunch and their company hired me to deliver speeches for a 12-city speaking tour throughout the U.S. and Guam. It gave my business, Wealth Building Academy, LLC the push it needed from the start!”

– Paul Vann, Owner, Wealth Building Academy, LLC

8. “My luckiest moment was during the national filming of “The Place Beyond the Pines.” It was filmed in Schenectady, NY starring Bradley Cooper and Ryan Gosling. Because the film company loved my business so much, they asked me to feed Bradley a paleo diet for 7 weeks and we had a cast party for Ryan Gosling. I was paid very well to feed Bradley, and I received a lot of free press. Bradley gave my restaurant several shout-outs and TMZ became interested as Ryan was dating Eva Mendes and they wanted the story. My little restaurant went national – Bradley endorsed my book, Is the Coffee Fresh?, and my business has had a huge increase in sales to this day!”

– Marc Renson, Owner, Ambition Coffee & Eatery, Inc.

9. “I wanted to start investing in real estate and I was introduced to a fellow investor who needed a partner in one property. I became his partner and after 3 years made $35,000.00 profit. I took this money and invested it purchasing another property. He became my mentor and I became wealthy following his tips and tricks of the trade. To this day, 14 years later we keep in touch and we still talk about real estate strategies! He was my lucky horseshoe!!”

– Maria Rekrut, CEO and President, Niagara Vacation Rentals and Niagara Real Estate Investment Group

10. “When I founded TrivWorks in 2009 as NYC’s only corporate event entertainment/team building company specializing exclusively in live trivia, I was seeking above all to differentiate my offerings from pub quiz & bar trivia, and establish credibility in my area. That’s why I was shocked several months later to receive a message via Twitter from Pat Kiernan, longtime NY1 morning news anchor and former host of VH1’s The World Series of Pop Culture, who had discovered my company and wanted to be a part of it. Pat and I have since collaborated on dozens of events, including creating the largest public trivia nights in all of New York City, with 300 people regularly attending events which TrivWorks produces, and Pat hosts. Forming a partnership with a beloved local celebrity who just happens to be a veteran game show host is by far the luckiest thing which could ever happen to a trivia company owner who’s just starting out!”

– David Jacobson, Owner/Producer, TrivWorks

11. “Landing a spot on ABC’s Shark Tank national television show was definitely the luckiest moment for SwimZip! There were over 35,000 applications for the show this year and we got picked. Turned out to be fantastic exposure for our small business – we got over 8 million viewers and the highest rated Shark Tank ever!”

– Betsy Johnson, Founder and President, SwimZip

12. “Over a decade ago, as a freelance graphic designer, a delivery truck carrying my new client’s tradeshow materials and marketing collateral had crashed. The driver was okay, but the truck burned along with everything in it. Instead of reprinting the old content, they saw it as an opportunity to start fresh and asked me to redesign everything. Though it was bad luck on their end, it was a financial boost and time commitment that helped prompt the opening of my own design agency.”

– Corey Wilkinson, Owner/Designer, Wilkinson Brothers, Inc.

13. “My luckiest moment was performing comedy for Obama. How’d I get there? I was a senior engineer with Intel Corporation. My job was to travel the world with Chairman Andy Grove, doing technical demonstrations on stage at events, and I was incredibly nervous about speaking on stage. I took a comedy class to get over the fear, and the comedy kind of took off. Since then, I have performed at the Democratic National Convention, at a TED Conference, at three presidential inaugural events, for Hillary Clinton, for Donald Trump at his golf course in Palm Beach, for Apple Co-Founder Steve Wozniak and for many similar luminaries. I recently performed at the Kennedy Center in Washington DC and on the MDA Labor Day Telethon with Carrot Top and Penn and Teller. Also, I appeared in an Apple Get a Mac commercial. I perform all over the United States as well as in many foreign countries. My life is a little like George Clooney in Up in the Air, just without the sex LOL.”

– Dan Nainan, Comedian/Actor/Voiceover Artist/Computer Geek,

14. “My luckiest moment happened when accounting told the corporate VP I was working for that I’d been slightly overpaid for a year. He decided to threaten me: pay the money back or else. So I simply resigned, and immediately began my business: consulting, writing and speaking. Within a year, that same company brought me in as a consultant, at a rate several times higher than the over payment rate. And several years later, that VP got to sit in the audience and listen as I delivered the opening keynote at his new employer’s annual conference, for a daily fee far more than what I’d been overpaid in a month when working for him.”

– Barry Maher, Owner, Barry Maher & Associates

15. “I was stopped for lunch on the way back from a customer visit. I’d been doing this for 12 years and had been contemplating for some time either selling it all or changing the scope of the business. The phone rang and it was a man I had met years ago. “I have a proposal.” he said and I asked him where he was at. Surprisingly, he was just down the street. Moments later, there at a Starbucks on a loose leaf piece of paper, we outlined a new company plan. Now three and a half years later the company has completed its best year ever and is going strong into 2014.”

– Linda Bishop, Owner, LWi Custom Cabinets

16. “My luckiest moment? I showed up when no one else would. We had a very large customer who built luxury apartments who’d just finished a major project to discover there was no broadband to the property. What made me even more hesitant to go was no other suppliers would look at it (it was going to be a major project) but I went anyway. I showed up and IMMEDIATELY sold a multimillion dollar project which a few days later I resold to another company (with the customer’s blessing) who actually could do it (there was NO WAY we could have pulled it off). That was the most profitable 30 minute drive I’ve ever taken.”

– Michael Bremmer, CEO,

17. “I struck a deal while out with my family at the zoo. While we were checking out the monkeys, I told a joke to everyone:

Lawyer: Doctor, before you performed the autopsy, did you check for a pulse?
Witness: No.
Lawyer: Did you check for blood pressure?
Witness: No.
Lawyer: Did you check for breathing?
Witness: No.
Lawyer: So, then it is possible that the patient was alive when you began the autopsy?
Witness: No.
Lawyer: How can you be so sure, Doctor?
Witness: Because his brain was sitting on my desk in a jar.
Lawyer: But could the patient have still been alive nevertheless?
Witness: Yes, it is possible that he could have been alive and practicing law somewhere.

Turns out, there was a man standing near us who was a lawyer with a fantastic sense of humor! After chatting and learning that this particular lawyer connects attorneys with expert witnesses, he told me he had a case for me. We signed a deal that day at the zoo! It turned out to be a really lucky meeting. The lawyer works for a large law firm and not only personally brought a lot of business to The Expert Institute, he also introduced me to many of his peers, opening the door to a great number of business opportunities.”

– Michael Talve, Founder and Managing Director, The Expert Institute

18. “The area we feel we got lucky in, which has given us a great opportunity to claim the beauty swapping industry, has been being first to market. We started eDivv back in May 2013 and launched in January 2014. There was plenty of time for a different company with a similar platform to release their site before us, making it difficult for us to compete, but we managed to be first to market. I guess you can call that luck!”

– Jon Katz, Co-Founder, eDivv

19. “I was the largest publisher of artwork from television commercials in the country and the rubber ducks started out as just a side business. One week, I started mailing out press releases to newspapers all over the country. I get a call back from the paper for Atlantic City, New Jersey. They said we got your release about these celebrity ducks, but why should we do a story about you? I told them that I was from New Jersey and I used to go to Atlantic City as a kid! That weekend a small article appeared in the Sunday edition of the paper about us. It just so turns out that the Vice President of The Philadelphia 76ers happened to catch it! He lived in New Jersey. He calls me and then flies out here to meet to see if we can do Allen Iverson, their superstar player, as a CelebriDuck. It was an unbelieveably successful promotion and picked up by the national media. The New York Yankees and The Chicago Cubs were calling to do similar promotions. Suddenly, I had a whole new company on my hands and I made the decision to sell off the animation and we became all ducks and never looked back! That one lucky moment of the reporter even responding to our press release and it then appearing in the paper that weekend and even being seen by this one man totally changed the history of the company and my life! As I write this, I am literally delivering 10,000 more Allen Iverson rubber ducks TODAY for his retirement ceremony this Saturday. That’s right, it was such a successful promotion that ten years later, they are doing one final promotion with the ducks for the event this weekend!!”

– Craig Wolfe, President, CelebriDucks

20. “The luckiest moment for my business was actually when my business was merely an idea for my first product. I had been searching for a product to safely and naturally help soothe & moisturize my dog’s paw pads, couldn’t find one, and was convinced I needed to create one. The problem was that I was a sound engineer, not a herbalist nor a chemist. I had a day off in San Diego, CA and was walking around when I stumbled upon an art festival, where I then bumped into a good friend I hadn’t seen since high school. We went to lunch to catch up, and as it turned out she had become an herbalist AND chemist with a business of creating natural products. Ten years later, we’ve created my entire product line which has been able to help thousands of dogs with numerous skin challenges form paws to hot spots, cysts, and ear infections!”

– Elyse Horvath, Founder, Natural Paws, LLC

21. “In 2011 when my two fellow Co-Founders, Farbod Shoraka and Gregg Weisstein, and I needed to figure out a way for the initial funding of BloomNation, I came up with the idea to get the money by taking my chances in a game of poker. There was a huge poker tournament coming up in the LA area and the three of us decided to take a chance on the future of the company – I entered in for a grand prize of over $25,000 to fund the initial development of BloomNation. While Farbod and Gregg were working out of the casino’s café area, I was working to beat everyone else in the competition. In the end, I won! Because of that hand of cards, our group of three childhood friends could now start BloomNation together.”

– David Daneshgar, Co-Founder,

22. “I got an email out of the blue from one of the executive producers of ABC’s Shark Tank asking me to call her to audition. I made the call, was fast tracked through the process and ended up on season 3 of the show! My sales for that month alone eclipsed the prior year and it completely changed my business and life for the better.”

– Kelly Costello, Owner and Founder, Puppy Cake LLC

23. “I’m a busy mom with an idea. Gandzee offers entire wardrobe collections and individual pieces for babies and kids ages 2 to 6 – perfect for busy parents who want to buy a season’s worth of kids’ clothes with the click of a single button. I was inspired to establish a kids’ clothing company that specializes in styling entire wardrobe collections as a direct result of being a busy mom and trying to dress my kids at the same time. My lucky break came when Katie Couric’s show Katie invited me to participate in their Mothers of Invention segment!”

– Jen Nomberg, Owner, Gandzee

24. “eCreamery Ice Cream & Gelato was founded out of a pure love for ice cream and the power of a personalized gift. We love the idea of making ice cream as a GIFT that will be bringing a smile to someone’s face and make a memory. Whether it’s Birthday Ice Cream, Get Well Ice Cream or Thank You Ice Cream, we want to make the moment delicious. Our big break came when we were invited to participate on Shark Tank on ABC!”

– Abby Jordan and Becky App, Founders, eCreamery Ice Cream & Gelato

25. “RAINRAPS started as a simple idea on a rainy day. Stacy Struminger, a New Yorker transplanted to Richmond, VA, had long seen the need for a more stylish, lightweight, waterproof accessory in the often wet and humid Richmond climate. Sharing her idea with her best friend, Rachel Teyssier, they decided together to make the vision a reality. Our big break came when Sarah Blakely of Spanx announced we were the winners of the Leg Up Competition, this is where Spanx chooses one company they’d love to promote via their catalog and website. After that we were selected as the winners of the TODAY show’s Bright Idea competition, which enabled us to appear on QVC!”

– Rachel Teyssier & Stacy Struminger, RAINRAPS

26. “My luckiest moment occurred back in the ’90s when a couple, who were my clients, owned a business together and broke up. When they broke up, which for the moment ended their business, it appeared that I had lost one of my most faithful clients. Within the next 30 days, each started their own businesses to attempt to regain their clients and expand with their own ideas. They both contacted me and hired my company, resulting in nearly double the revenue for me within the following three months, even though it was less than twice the workload for me.”

– Dave Kohl, Marketing Director, First In Promotions 

27. “The first bit of luck came when a friend shot down my first business idea with the comment, ‘Adults don’t want to wear bibs.’ It forced me to get more creative and design a fashionable dining scarf that serves as an adult bib. My new design has set me apart from the competition. My second bit of luck came when I stumbled on the perfect fabric for my new design. I was looking for something that draped elegantly, but was also stain resistant and machine washable. I found it on an online wholesaler. It turned my hobby business into a substantial business with a product line that is changing the way people protect their clothes from food spills.”

– Kathy Steck, Owner, DinerWear

28. “My luckiest moment was being turned down by CompUSA for a part-time job in high school. After being rejected, I decided to put that time into further developing and expanding my web hosting and server management company, which I later sold from my college dorm room at age 18. I used the money from that sale to invest in five other companies, one of which became TechnologyAdvice – which is now projecting $9.2 million in revenue this year.”

– Rob Bellenfant, CEO, TechnologyAdvice

29. “My luckiest moment was having the Wall Street Journal doing news coverage about my company.”

– Matt Morris, Founder/CEO, CrowdFunding Promotion

30. “Getting let go from my job was my luckiest moment. In the early 2000s, I was (unhappily) working at a marketing firm and had been considering going out on my own for a few months. In fact, I had hooked up with a former coworker and we were doing some really exciting moonlighting work, but I wasn’t quite ready to leave my full-time job (with salary and benefits). Then one day, I got called into the conference room with my boss and my boss’s boss, and they told me I no longer worked there. I freaked out for about 20 minutes until I realized they had done me a huge favor, as I now could pursue a new venture with my former co-worker (now business partner), and I have never looked back.”

– Jeff Kear, Owner, Planning Pod

31. “After buying another losing lottery ticket, I went online looking for an easy way to make some extra cash. I discovered that there are thousands and thousands of businesses that offer cash referral fees in order to seek new business. I wasn’t able to find a single source for finding those referral programs, so I set up a website and started filling it with referral fee programs. Yes, it was a lucky moment discovering a need for a single marketplace, but a lot of experience has taught me to know an opportunity when it is staring me in the face!”

– Richard Houston, Owner,

32. “As a new business owner I was very lucky in starting my first business. The opportunity was literally dropped in my lap by a close family friend who was a supplier in a industry that I knew nothing about. The friend said that a certain city in another state did not have distribution for their wares, which for them as a international supplier of industrial products was unheard of. It seemed as though an old line company had a vice-like hold on the city I was looking at, and no other distributor had taken a run at his business as a new competitor. The thing was, that that owner was getting ready to retire, and it so happened that the business / city was ripe for the picking. I ended up being the main supplier in that town for the next 12 years until I sold out. It was the best business decision I ever made in over 40 years of being an entrepreneur, and it was out of sheer luck.”

– Bill Whitehurst, Owner, Whitehurst Mergers & Acquisitions

33. “My luckiest moment as a business owner came on Dec 19, 2007 when my business and I were featured in the prestigious Wall Street Journal – ON THE FRONT PAGE! When the reporter called I was excited because I thought it was for one of my PR clients – but he said they had been seeing our pitches about our unique clients that we always sent to the WSJ newsroom and wanted to learn more about how this small biz in the Midwest always worked with such interesting companies and products. They flew a reporter out from NYC to my business in Lawrence, KS for a couple days, interviewed me and some clients nationally and the article ran several weeks later. The reporter kept saying all along that this is just going to be a small feature in the business section. Then when he called to tell me the article was running he said that it turned into a better article that they thought and ran it on the front page, smack center in the HEAD!!! As you might imagine, the resulting firestorm of interest from new prospective clients and potential strategic alliances was crazy for months and even years after. Although it certainly went back to more normal operation after a long while, more than 6 years later and not a week goes by where someone doesn’t email or comment about seeing that article.”

– Todd Brabender, Owner, Spread The News PR

34. “I have had two lucky moments that set the stage for my career as an entrepreneur:

1) When I was 19 and working in a restaurant, the owner decided to open a new location and let me participate in the process, from then on I always felt I looked deeper into the why of what was going on at work in any environment.

2) Two years later, backpacking through Brazil and bartending for some extra cash, a regular would come in and discuss the challenges of development in the impoverished Sertao region of Brazil. After a few weeks, he asked why I was knowledgeable about the subject, I told him it was because I studied law and economics. He asked if I would be interested in accompanying his team on work trips to the interior of the country and I accepted. A few months later, I was helping him with projects for Sebrae while starting my own business interfacing between western companies who wanted information about the region and the local agencies in best position to provide it.”

– Brian Meissner, Founder, SA Trails & Owner, El Diablo Tranquilo Hostel & Bar

35. “I believe you make your own luck in business, though hard work to establish a well kept reputation. However, I do believe my luck came into play when picking my team. You take a chance on someone to represent your business and I was quite fortunate to have assembled a great crew. They represent my concept in such a manner that ensured our success, making us the best DJ/Karaoke/Live Trivia Company around.”

– Jeremias De La Cruz II, Owner, SoCal Entertainment

36. “On a slow business day at our little food cart across from Voodoo Doughnuts in downtown Portland, a whole gaggle of pedicabs descended upon us! Apparently, BrandUSA’s MegaFam tour was making their way through Portland and had planned to stop at Voodoo. The pedicab cyclists told the MegaFam tourists about Mix ‘N’ Match Creamery’s liquid nitrogen ice cream and they just *had* to see it for themselves! Not only did we sell a bunch of ice cream to these folks, but as luck would have it, Mix ‘N’ Match’s made-before-your-eyes liquid nitrogen ice cream was in photos and videos all over MegaFam’s Twitter and Facebook pages!”

– Eric and Genevieve West, Owners, Mix ‘N’ Match Creamery

37. “My company got a great boost when the patent holder of Instament contacted me. Donald’s concrete material is lighter than typical concrete allowing monolithic concrete homes to be built, 4 inches of concrete from roof to foundation faster and cheaper. Currently, DRD Enterprises is offering concrete mobile homes that will not blow away.”

– David Pressler, Owner, DRD Enterprises Inc of Davie SAM Reg

38. “Our luckiest moment we’ve had while operating the business was how we earned our first major client. Our first official client under the company name quadrupled our income at the time, and actually came (quite by accident) from my previous employer. This happened about 2 months after starting the business, so it gave us a real shot at surviving right out of the gate.”

– Jared Carrizales, Founder, Heroic Search

39. “My luckiest moment as a small business owner occurred when I met my current business partner. The initial meeting was entirely coincidental and we were both interested in striking out on our own at the time. The reason I consider that to be my luckiest moment is because we are basically a perfect fit. His talents center more on the technical aspects of owning and operating a website, while mine are more geared towards marketing and business development.”

– Andrew Schrage, CEO/Editor-in-Chief, Money Crashers

40. “My luckiest business moment occurred at roughly 2:10 PM MST on February 24, 2006. A senior executive of my client’s company had just come back from lunch the moment I was describing a product we offered (to one of his colleagues) that he had been desperately trying to find. Since no others existed, we evolved our technology for the next 7+ years to suit their ongoing needs. On August 1, 2013, we had a successful exit on that product (sold to our client), which has positioned my company to pursue more opportunities going forward.”

– David Mizer, Owner, LookatUsedCarsServiceDrive, FindMyLostLove

41. “The luckiest moment of my business was when, having only $100k in funding to start the company, we were able to order our key piece of manufacturing equipment for $3 million with no deposit or down payment. It took the manufacturer 9 months to build the equipment and we were able to raise the necessary capital to purchase the equipment by the time it was delivered.”

– Larry Amon, Chairman/CEO, The Alternative Board, SW Florida

42. “Our luckiest business moment occurred when we first rolled the dice and put an ice rink in Bryant Park – on the roof of the New York Public Library’s lower level, no less. It had never been done before, and nobody knew what kind of attendance potential or penchant for ice skating the middle of the Bryant Park lawn could have. Our luck came when we took on the full financial risk of this project, and then in a very short period of time designed, installed and operated the first, modular, temporary, seasonal and FREE ice skating rink facility in NYC. The rink, which coincided with our Holiday Shops and food concepts for the Winter Village at Bryant Park, led to a far more unique and special winter NYC experience in a public space that has become a destination for tourists and locals alike, as well as an amenity to the city. (The Winter Village at Bryant Park is completely privately funded, no public tax dollars used in exchange for a viable economic benefit to the city.)”

– Itai Shoffman, Founder, Upsilon Ventures

43. “My lucky moment came after starting a PC repair business, which was going okay but was not really profitable. A couple of clients mentioned, in passing, that the presentation folders they had printed up (from different vendors) were all disappointing. Hearing their complaints, I felt like there must be a better solution for my customers’ problems with presentation folders. I launched Company Folders in 2003, shut down the PC repair business, and has built a business that is scalable, and continues to grow.”

– Vladimir Gendelman, Founder, CEO, Company Folders

44. “My luckiest moment as a business owner was when a redundancy freed me from the cloying crush of corporate lethargy, and allowed me to start my business in the first place! To think I could still be trussed up in a collar and tie, smiling politely and feigning interest at some half-wit while, enraptured, he espouses his latest illogical, irrelevant business philosophy to a sycophantic group of business colleagues, all of whom want his job!”

– John Strahan, Managing Director, Outdoor Living Direct

45. “I knew I wanted to share my knowledge of healthy living and fitness with the world, but I didn’t know how. So, I did the logical thing, I quit my 60 hour a week job as a Pilates instructor, to figure it out. Three months later, I met my business partner, Robert Wald, who was about to launch The Body Archer Back Stretching Chair. Within fifteen minutes of seeing the product, I designed an entire core strengthening program and laid out several potential marketing options for The Body Archer. He made me a partner on the spot!”

– Kim MacKenzie, President, The Body Archer

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