Hard Work or Luck? 5 Entrepreneurs Reflect on Their Paths to Success

In the unpredictable world of entrepreneurship, the debate persists: is good luck as important as hard work? For many business owners, it's about optimizing bad breaks and understanding that setbacks can provide invaluable lessons to reinvent and refine strategy. While failure might sting, it can also offer crucial growth opportunities. By complementing hard work with personal rituals – like wearing a lucky tie – entrepreneurs can shape a mindset for seizing opportunity. With a combination of intuition, preparedness, networking, and resilience, they can create and recognize serendipitous encounters, and capitalize on them. Against this landscape of chance and grit, these five entrepreneurs shed light on the interplay between effort and fortune along their paths to success.

1. Take advantage of opportunity.

Elana Tenenbaum Cline – founder of Carta Creatives, an interdisciplinary design studio focused on real estate, hospitality, and residential clients – considers luck a pivotal factor in landing a big account. After her firm was featured in one of the world’s leading newspapers, she wisely leveraged the news in her company’s inaugural email newsletter. “I was nervous to send it. Normally, I like to stay kind of quiet on things. But I hoped that one person in particular would see it, and it would strike up a conversation,” she says. The person she had in mind, a busy executive at a major company, happened to open the email from a sea of promotional messages. Serendipitously, she happened to need Carta Creatives’ services at the same time, replying immediately: “I have a new client for you. It’s me.”

2. Don’t be afraid of risk.

When he was 10, Joe Spector and his family fled Uzbekistan to live at an Italian refugee camp before landing in California's Bay Area. Now founder and CEO of Dutch, a telehealth company for pets – a follow-up to telehealth pioneer Hims & Hers, which he founded and took public at a valuation of $1.6 billion – Spector is living proof that possessing a unique openness to risk can pay off. “With my personal experience as a refugee, I've always had to do the hard thing,” he says. “So it’s relatively easy for me to take risks in business, because I've developed a thick skin over time. Before we left the USSR in the middle of the night with just a suitcase, my mom said that going to America was like going to the moon – such an unknown. We did it anyway. As an entrepreneur, you have to be comfortable with the unknown. It’s lucky that I’ve been able to leverage this perspective, and that we ended up in the Bay Area, the hub for startup entrepreneurs.”

3. Be prepared.

No matter how hard Mikey Reen works, Mother Nature rules. With a summer hospitality business dictated by the whims of weather, he and his Riis Beach Cooperative co-founder Dylan Sirgiovanni prepare for the meteorological rollercoaster as much as humanly possible. Their collection of food and retail vendors, bars, live music, and other outdoor events is located along a nearly one-mile-long boardwalk at Jacob Riis Park, part of the National Park Service and known as "The People's Beach" on New York City's Rockaway peninsula. With about 10 weather apps on his phone, Reen adjusts weekly schedules for more than 40 employees and tailors food prep to the forecasts.

As entrepreneurs, we need to think more about the luck we engineer rather than random luck that falls in our lap.

- Joseph Quaderer, founder, StorySavor

“We're lucky to have minute-to-minute updates,” he says – especially given the threat of hurricanes to Rockaway, where he and Sirgiovanni grew up. “We have three big holiday weekends to do much of our business: Memorial Day, Fourth of July, and Labor Day. The Fourth was not all it could be because of the weather. In June, we had wildfire smoke and lots of rain. Fortunately, August turned things around at the perfect moment. With better weather from mid-July on, we were able to even out our numbers.” While unlucky weather is a constant concern, and a major hurricane hasn’t hit Rockaway since 2012, it’s a combination of flexibility and hard work that has kept their business ventures growing since 2015.

4. Be patient, then pounce. 

"As entrepreneurs, we need to think more about the luck we engineer rather than random luck that falls in our lap,” says Joseph Quaderer, founder of StorySavor, a biography writing services company. “It was lucky that in 2021, I had a dinner conversation that sparked the idea to start the company. But at that point, I had a B.A. in finance from Notre Dame, an MBA in finance and strategy from NYU, had spent 17 years as a Wall Street banker, written novels, and graduated from Columbia Journalism School. So while the idea originated at dinner, a lifetime of hard work and dedication brought the concept from ideation into the real world."

5. Expect luck.

When Lisa Ann “LAMARKS” Markuson, founder of the experiential entertainment agency Ars Poetica, got her start in New York City, she was in her early 20s with no industry connections. “My lucky breaks were mostly due to being incredibly naive, hopeful, and enthusiastic. If you truly believe every opportunity is a good one, it somehow becomes true.” With an approach she calls “fake it ‘til you make it,” she used to walk into “fancy-looking venues” as if she belonged, tell people she was “the poet booked for tonight,” set up her typewriter, then schmooze away. “It never didn’t work, and I got lots of legit gigs that way.”

Whether confidently gate-crashing an event, arriving in the right inbox at the right time, or forging a path through sheer grit and determination, these entrepreneurs recognize that while luck can influence success, it can never define it entirely. 

A version of this article was originally published on November 09, 2015.

Photo: Getty Images