How To Think Like A Wildly Successful Entrepreneur

Secrets I learned sitting at the knees of entrepreneurial mavericks.

Clare Loewenthal
Ascent Publication
7 min readMar 31, 2019

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Photo by Miguel Bruna on Unsplash

One of the great privileges of owning a business magazine was the enlightening conversation I had with some of the world’s most iconic entrepreneurs.

I’ve always been fascinated — some would say obsessed — with understanding why one start-up soars, while so many others fail.

During my interviews with myriad business owners, I searched for the commonality in their entrepreneurial journeys, so my readers could understand and apply proven growth strategies to their enterprises. The side-benefit was I was able to apply them to my own business as well.

My key learning was that the elements of an enduring business are inextricably linked to the talents, personality, values and mindset of its founder.

Sustained Passion

Creating a business is exciting. In the start-up phase it’s easy to get up early, power through the day and work late into the night. Challenges are seen as opportunities.

Five, seven or nine years down the track, most people’s enthusiasm has waned. The daily grind of managing staff, overcoming cash flow challenges and responding to an ever-changing marketplace takes it toll, and the founder typically finds it harder to get out of bed. Challenges are seen as challenges.

Successful entrepreneurs find ways to sustain their passion year after year. They identify and focus on the parts of the operation that energize them, and delegate the tasks that drain them. This benefits the business as well because what excites people is invariably where their talent and value to the business lies.

The takeaway for my business: The one sure-fire way for me to reconnect with my passion was to interact with my readers. I welcomed people connecting with me through the magazine and I accepted every invitation to speak at conferences and events where I would meet readers. Their love of the magazine filled me with pride and renewed commitment.

Separating Ego from the Business

This is a tricky balancing act. It takes a strong self-belief to put everything on the line and turn your dream into a reality, but being driven by self-belief is not the same as being ego-driven.

The most successful entrepreneurs I met were those who knew that enterprises could only grow if they became bigger than the founder, which meant relinquishing some personal control.

Starting a business requires a different skill set to growing it: some people can make that leap but many cannot. Founders who want to retain control of every element of the company constrain its expansion, and make it harder for them to work on the business rather than in the business.

Successful entrepreneurs happily employ smart people: in fact, many proudly told me that their employees were more talented than they were. Not only did they hire clever people, they let employees do their job unimpeded.

The takeaway for my business: My natural affinity was with the creative elements of the magazine, so I focused on publishing a beautiful magazine filled with inspiring content.

Because I’m not a natural salesperson, I hired top quality sales people and then heavily incentivized them to perform. The sales mindset is anathema to me and this often led to me being disappointed by big promises that were never fulfilled. To avoid this, I made the sales team accountable through rigorous reporting systems.

Concentrating on Your Business not the Competition

In 1996, when I met Subway co-founder, Fred DeLuca, the chain had 11,300 franchisees worldwide. When Fred started Subway at 17 years of age he had massive competitors like McDonald’s and Burger King.

Rather than competing head-to-head with the fast food titans, Fred focused on creating a healthy alternative to the fatty food sold by the established franchise chains, and the rest is history.

Of course, Subway’s success spawned a multitude of competitive food outlets selling submarine-style sandwiches, and today there’s a vertical within franchising just for healthy eating. But Fred had a first to market advantage, and was always a step ahead of his competitors.

Me-too businesses rarely succeed. Smart operators focus on creating a unique offering rather than obsessing over a competitor’s every move. Yes, you have to understand the competitive environment in which you operate, but your best strategy is to learn what customers really want and then deliver that, without becoming distracted by competitors.

The takeaway for my business: My magazine competed directly with a title owned by a high-profile media identity who could cross-sell and access distribution channels I could only dream of.

My competitive advantage was that I was a business owner facing the same challenges as my readers, rather than a media executive sitting is a glitzy corporate office.

I had an instinctive feel for what business owners wanted to read about because my issues were their issues. This gave the magazine’s editorial platform an authenticity that allowed it to become the country’s top selling magazine for small-to-medium businesses.

Understanding Risk and Failure

Successful entrepreneurs understand risk: they understand the difference between impetuous, reckless decisions and considered decisions based on a realistic assessment of a particular course of action.

It’s easy to believe that people who build a global brand simply have the Midas touch, but in my experience their success is underpinned by a thorough knowledge of the market, where it’s heading, and what opportunities that presents. They ask questions and they listen closely to the answers. They understand their customers’ needs and know how to convert unmet needs into dollars.

You have to be risk-taker to start a business but, paradoxically, the more successful you become, the harder it may be to take risks. You have so much more to lose.

If you fear failure, you may never go out of business but you’ll also never make the bold decisions needed for rapid expansion.

One of the magazine’s best selling issues was when we had Robert Kiyosaki of Rich Dad Poor Dadfame on the cover. Robert’s beliefs around failure reflect those of many entrepreneurs I met.

He says, “Winners are not afraid of losing. But losers are. Failure is part of the process of success. People who avoid failure also avoid success.”

Even the giants of business sometimes lose. No one exemplifies the fearless maverick better than Richard Branson. Over 400 brands have been launched under the Virgin banner but not all were profitable. Who remembers Virgin Cola, Virgin Vodka, Virgin Cosmetics, Virgin Brides or Virgin Cars? Branson proves that if your wins are spectacular enough, people forgive you for the failures.

The takeaway for my business: I never considered myself a risk taker but, in retrospect, I see that starting a magazine with few resources and no experience was a huge risk.

I’m an analytical thinker when it comes to business decisions — lots of lists of pros and cons — but over time I also came to trust my instincts. I realised that I made mistakes when I didn’t listen to my gut.

I also became less afraid of failure as the business matured. Publishing is a high stakes game but once the business grew, I knew the custom publishing arm and the established title could mitigate the inherent risk in the new publications I launched.

Knowing When to Pivot and When to Leave

The one certainty in business is that just when you think you have the right offering, the right marketing and the right team, business conditions will change. All the highly successful business owners I met were adaptable and responsive to the market.

One of the current business buzzwords is pivot. There seems to be plenty of pivoting going on, but profitable businesses have always responded to a changing marketplace.

Technological developments are altering consumer-spending habits more rapidly than ever before, and radical, brave changes in direction are becoming necessary for brands to remain relevant.

There are two aspects to this argument. In business you need to be tenacious. Sometimes people become discouraged and change direction too early or too often, or give up completely.

Conversely, sometimes founders are so committed to their original vision that they ignore what the market is telling them, and fail to make the necessary adjustments to meet consumer demand.

The takeaway for my business: The market showed me several years ago that it was becoming increasingly difficult for independent publishers to make money. Technological changes were making print publications harder to sustain because people were getting free information online.

Although we had an online version of the magazine, even the world’s largest publishers were — and still are- struggling to find a viable online revenue model for print titles.

It was a difficult decision to sell the business but it was the right one. My years in publishing were the happiest of my life and by every measure what I created was successful, but I knew that success couldn’t be sustained.

Selling the business would have been much harder had I not had access to the inspiring entrepreneurs I met along the way. The confidence they demonstrated gave me the courage to listen to my instincts and be true to myself.

And after all, I told myself; wildly successful entrepreneurs always know there’s a new adventure waiting just down the road.

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Clare Loewenthal
Ascent Publication

I write about business to pay the bills and everything else to seek meaning and truth.