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Entrepreneur Stories of Struggle and Success: 7 Founders Tell All

Scaling. Building a stellar reputation. Improvising. Dealing with stress: Here's how six guys (and one gal) did it.

It’s never easy running the show, especially when you’re starting a new business. When I started Tailored Ink, I dealt with my fair share of struggles. Sometimes I was unprepared. Or ignorant. Most of the time, I never saw hurdles coming my way until I had tripped right over them.

Related: 8 Great Entrepreneurial Success Stories

But pretty soon, I learned the truth: It’s okay to mess up. To feel overwhelmed and beaten. Every entrepreneur, no matter how prepared, trips over unexpected hurdles. The successful ones learn to get back up as soon as possible.

To learn how successful entrepreneurs deal with various obstacles, I asked some local New York City business owners about their early stage struggles, how they overcame them and what they learned along the way.

Luke Holden: Scaling with integrity

When you’re desperate for cash, it’s easy to cut corners, compromise your values and deliver a subpar product or service. But the businesses that manage to weather their growing pains and stick to their guns are the ones that last longest and shine brightest.

Luke Holden is the founder of Luke’s Lobster, a seafood chain with high ratings. Asked about maintaining integrity, he said: "A commitment to being an entrepreneur is a commitment to change and evolution. I don't think you ever really know you're going the right way, but you must also be prepared to find, and build, a new way." 

As his business began to grow, he told me, "We were faced with the challenge of how to scale with integrity. When our supplier could no longer meet the demand of our guests, we stuck to our guns and the commitment we made to our guests. We took our profits to date and invested in building our own seafood company to guarantee transparency.

Related: 6 Stories of Super Successes Who Overcame Failure

"We took a risk on our guests . . . It paid off, and today we strive to continuously push our own boundaries by building new relationships at the source."

Ross Sapir: building a reputation

Some owners start out in industries that are popular, appreciated and admired. Others have to put on rubber boots and wade through the mud. Ross Sapir, president of Roadway Moving, had to do just that. Asked how he built an immaculate reputation in a not-so-reputable industry, he told me, “I was in the moving industry for a long time. But there was always a stigma. We have to deal with the customer’s perception that we’re trying to rip them off and we don’t care about their stuff. Changing that perception and building a positive reputation was the hardest thing I had to do."

Sapir said his goal was to build a business "where the day that people moved was the best of their life." He continued: "To do that, I had to invest more in my employees and work harder than anyone else. I had to go out of my way to make sure people knew I actually cared. But it worked.”

Sarah Saltzberg: improvising when necessary

Starving artists and new business owners have one thing in common: They have to be masters of improvisation. The ability to make bold, decisive decisions with incomplete information and pivot quickly in a different direction if necessary is instrumental to early stage success. Asked what she attributes her success to, Sarah Saltzberg, founder of Bohemia Realty Group, told me: "Building a real estate company wasn't easy, but my background in theater and improvisation was instrumental to our success.

"Creating something from nothing is what artists do," Saltzberg added. "The tools I applied to my theatrical endeavors translate easily to business -- knowing how to think and solve problems creatively; being persistent and objective oriented; and [knowing]  how to work collaboratively continue to be the core strengths of our firm.”

Artem Mashkov: handling stress

A common experience for all new entrepreneurs is chronic stress. Some of it is positive and motivating. But too much stress can be crippling. Artem Mashkov is a serial entrepreneur who has started various businesses around New York including DevTribe. And stress, he said, "almost killed me. Around three years ago, I lost 20 pounds due to stress. It wasn't because things weren't going well. I was stressed because things were going too well, and I couldn't capitalize on all the opportunities coming my way.

"But then I went full Zen mode. I started paying attention to my well-being, and the stress went away. Stress isn't external. It's internal. You choose whether you let stress control you. It's all about your perspective on life.”

Alexander Acker: seeking new business

Every business owner has one overriding and often irrational fear: What if all of my clients and customers disappear? What if one month, all my revenue vanishes? What if it’s not even my fault? Alexander Acker, president of the creative agency Adventure House, knows that his business is very seasonal. And that means that even happy clients can can disappear overnight due to budgetary constraints. So Acker made finding new business a constant habit.

“Clients eventually move on; things change, economies tank, so the road to success is to always paved with potholes and sinkholes," Acker told me. "To pull yourself out of it, you always need to have a channel available where you can connect with potential customers. To stay successful, I regularly attend conferences, to give my company exposure to new opportunities. It helps you arm yourself with a plan and dream big.”

Jan Roos: sustaining energy

When a business is new, it’s easy to feel optimistic and excited, but once you’ve been at it for a while, it can sometimes feel just like any other job. Jan Roos, founder of Expert Engines, a lead-generation company, related how he had to adjust to fading enthusiasm while still keeping up his energy levels.

“When you start out in a new business," Roos said, "you have all the optimism about how well things are going to work. But as I started to hear more and more objections, I started losing motivation and thinking that what I was doing wasn't unique or valuable.

"Regardless of the industry, you're going to hit a slump like this. Getting through it is a matter of doing the right stuff, day in and day out, without losing your optimism. This is a grind, but if you persist you can get through.”

Michael Tesalona: automating what works

Some entrepreneurs reach a point where they are more successful than they ever imagined, but they’re working 80-hour weeks. That’s not fun. To continue scaling while working less, some entrepreneurs turn to automation as a solution. Michael Tesalona,  founder of Bradford & Crabtree, an SEO company, is one of them. 

I’ve always been obsessed with the goal of creating a consistent stream of new clients," he told me. "I wanted a machine that I could turn on and off and know with relative certainty how much additional revenue I could expect.

"The process took a long time, required a lot of specialized knowledge and was expensive. But it was worth it. It was a lesson in the importance of positioning in a competitive market and the benefit of having a well-crafted, targeted sales message.”

Where there’s a will . . . 

If there's one common lesson to be learned from the diverse experiences of these successful business owners, it’s that there will always be obstacles to overcome. No one goes from zero to hero without breaking a sweat or feeling that all hope is lost.

This is likely one reason why the vast majority of startups fail. Somewhere along the way, those business owner(s) came up against a major hurdle --lack of budget, dissatisfied customers or an unexpected competitor -- and fell so hard they didn’t even try to get back up.

Related: These 5 Rags-to-Riches Stories Will Inspire You

Yet, when it comes down to it, there is always a way forward. It may not always be obvious, comfortable or even smart. But if you’re going to succeed, it’s up to you to find it.