Body_BusinessHindsight.jpgby Iris Dorbian.

“Regrets I’ve had a few,” crooned Frank Sinatra in the famous song, “My Way.” That fabled lyric can also apply to many small, established business owners when they look back in hindsight at their entrepreneurial journey, comparing the glorious highs to the abysmal lows. What do some of them wish they had known way back when they launched their business?

Success starts with the right people

David Guralnick, president of Kaleidoscope Learning, which designs and develops online learning courses for companies, wishes he had taken more time to find staffers that were the right fit for his company. He recalls an incident when he needed to hire a lead programmer to design and build a product for a Fortune 100 client, which was also co-funding the project. Because his business was still in its nascent phase, the project’s importance was heightened considerably. Unfortunately, his rush to hire ended up being counter-productive.

“As it turned out, I went through two lead programmers who did not work out before finally finding the right lead,” recalls Guralnick, whose 14-year-old company now has 40 employees. As a result of this staffing debacle, the product not only took longer than planned to complete, it fell short of Guralnick’s expectations. “More patience would have served me well,” he says now. “As an entrepreneur, it’s easy to start to think that you can do everything yourself, or at least to underestimate just how critical it is to work with great people whose styles mesh together well. Even if someone’s very skilled, things may not work out well if they’re unhappy in their role or aren't the right fit in terms of work type or personality.”

Don’t be shy about asking for help

Natasha Ashton, co-founder and co-owner of Petplan (a pet insurance company that launched in 2006), echoes Guralnick’s sentiments and also urges small business owners to surround themselves with experts who can help their company grow. “One of the best decisions we ever made as a company was to recruit Vernon Hill as company chairman,” explains Ashton. “His extraordinary experience in the financial services industry as the co-founder of Commerce Bank, coupled with his passion for creating fans not just customers, and his own experience as a pet parent, allowed us to take the business to the next level.”

PQ_BusinessHindsight.jpgTrust your gut

However, there’s something to be said for believing strongly in oneself. David Black, founder and CEO of Vicinity Media Group, which publishes several Northern New Jersey regional magazines (Suburban Essex, Vicinity, and InBiz), wishes he had placed a greater premium on his own instincts rather than ceding his authority early on to so-called experts.

“I’ve discovered only in the past couple of years that I know more about my business than the experts do,” concedes Black, who launched his company 20 years ago. “I only had a high school education and was never in publishing before. My theory was to get people who knew more than me and let them achieve my vision. It turns out they don’t necessarily get what you’re trying to do.”

Turning obstacles into opportunities

For husband and wife team, Natasha and Chris Ashton, it isn’t so much the regrets that they share, but an awed realization of the challenges they had to grapple with shortly after they began Petplan. Launching their startup in 2006, in the face of skepticism and a combined $250,000 in student debt, the Ashtons quickly found their foothold and by 2007, were seeing double-digit growth each month. But later that year, the burgeoning success of Petplan almost came to a crashing halt thanks to an unexpected turn of events.


“Chris shattered his ankle and broke two ribs in an accident,” recounts Natasha. To make up for his absence—Chris subsequently endured several surgeries and needed six months of rehabilitation—the Ashtons decided they must delegate if the company was to survive. “Our choice wasn’t safety or risk, but rather sink or swim,” she recalls. “By empowering our day-to-day managers, we could focus on our growth strategy.” (By 2008, Petplan’s staff size was 12 employees; today the company has more than 60 employees, according to Natasha).

Maintain focus, but be flexible

“As a small growing business, opportunities can seem endless,” says Guralnick. “There can be a temptation to jump at each new opportunity. On the other hand, being small does often allow you to be flexible. If something isn’t working or there is a particular new idea that is worth exploring, you can make changes. It’s a tricky balance.”

Establish core values

Set parameters for what your company will do and use that as a basis for making decisions.  “Regardless of how exciting an opportunity may seem, if it doesn’t support your core values, it probably isn’t right for you,” says Natasha Ashton. “As an organization of pet lovers, pets’ health and wellbeing is at the forefront of every decision we make.”

Find a space of your own 

In Virginia Woolf’s immortal short essay, “A Room of One’s Own,” published in 1929, she stressed the importance of women finding a private sanctum in which to incubate and cultivate their artistic ambitions and thus put them on par with men. Although Woolf’s admonition wasn’t about business, her passionate exhortation is akin to a best practice that Garden State publisher David Black emphasizes to small business owners just beginning their careers.  


“One of the best things an entrepreneur can do is find a space that they can think and dream creatively as often as possible,” he advises. “Because when you’re trying to do things in your head as an entrepreneur, it’s a lot different from reality.” 


To help him slip into a creative meditation, a state of mind he calls “a zone,” Black says he will often stay at home rather than go to the office and be distracted by the din of daily business activities. Engaging in this kind of focused reverie is an imperative for small business owners, particularly entrepreneurs seeking to embark on a venture. “You need to have a dream first and pursue it,” he reflects.  

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