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5 Leadership Tips from a Former Stockbroker Turned Entrepreneur

5 Leadership Tips from a Former Stockbroker Turned Entrepreneur

I have this friend, let’s call him Sam. Sam was once one of the most sought-after stock brokers in Manhattan but recently gave up his very lucrative career for one in entrepreneurship. His new venture? A mobile dog-grooming business that takes care of every need you could possibly want, without you ever having to physically take your dog down to the spa. Before you laugh, I guess I should tell you that last year, he grossed mid to high six figures in revenue. Who’s laughing now?

Sam is not unique, even though his business venture might be. He is among a growing number of people who are leaving high-paying corporate jobs to start their own business. But like most “wantrepreneurs,” Sam struggled with many of the same questions others have: how do I grow? How will I sustain growth? And most importantly, how do I lead a team?

I asked Sam to give me some of his tips, and I want to share some of them with you today.

  1. Value Your Team’s Skills

As a stockbroker, Sam was used to working long hours by himself, which gave him the benefit of keeping all the rewards for himself, as well as putting in as many hours as he needed to. Even in the early stages of his business, he was still able to work mostly by himself. When he started his business and began to hire employees, all of that shifted to a team mindset.

He started off bitter, believing that others were slowing him down, either because they couldn’t match his drive, or, even worse, they didn’t want to match his drive. Over time, he began to see the benefit that each one of them brought to his team, and instead of fighting against them, harnessed the collective power they all possessed for the betterment of his company.

  1. Dream Big

As an entrepreneur, your reality is only governed by how big you can dream, whether that’s a $60,000 a year side hustle, or a multi-million-dollar corporation. What Sam found was that he often underestimated his own dreams, and not only short-changed himself but short-changed his staff as well.

If your employees have signed on to work for you, even if it’s more than a simple “startup,” it’s most likely because they believe in you and in your vision. They deserve for you to develop a long-term plan for the company that will continue to grow, not stunt their potential earnings by dreaming small. When people feel like they are part of a team that is bigger than just themselves, they are guaranteed to work harder and better.

  1. Always Learn

Sam had an incredible amount of knowledge in one specific area (finance) but almost none in the one that he was passionate about (dog grooming). How could he ever hope to start a mega-conglomerate if he didn’t have any expertise? Simple: he learned.

One of the hardest things for anyone to do in any walk of life, but especially one as competitive as stockbroking, is to admit when you simply don’t have the answers. In this case, you have one of two options: you can either stumble along, fumbling through failure after failure, or you can lean on others’ who have expertise in that area. Fortunately for Sam, he chose the latter.

“I wanted to cut the learning curve,” Sam said. “I realized that I could either grow this company to the size I wanted in ten years or two years, but if I wanted it to be the quicker of the two, I had to get some help.” Sam put an ad on the local Craigslist classifieds looking for an experienced dog groomer and had twenty applications the first day. He hired three of them within two weeks and had his business up and running in four. How’s that for swallowing your ego? 

  1. Maintain Positivity around Your Staff

Entrepreneurs have a high attrition rate, most likely due to the enormous number of challenges that they often face. Businesses begin and end within a matter of months these days, right before they would have been successful – had the entrepreneur just stuck with it.

Sam faced a similar challenge. “When we were six months old, we were having a hard time maintaining working capital, and I figured we would have to file chapter 11 bankruptcy. I called some attorneys I know [side note: Sam used a group called Wasatchdefenselawyers.com, who specialize in business law], and they gave me some solid advice about how to keep the lights on. It really was simple; all I needed was a little push.”

Moral of the story? Don’t give up, and even if things do go bad, try to stay upbeat about it around the people that are working for you.

  1. Steady the Ship

“When I first started, I was all over the place,” Sam told me. “I was advertising here, thinking of new product offerings every twenty seconds, and it got to the point where my staff couldn’t keep up. I had to learn to maintain a balance in order to keep the business afloat.”

Sam is a classic case of “shiny new thing” syndrome, where a person chases every rabbit trail possible to the expense of their most important project. As a leader, that’s an error you simply can’t afford to make. Instead of going after every quick buck and chasing the latest in advertising, provide a calming force amongst your employees, who look to you for peace. If you’re calm, they’ll be calm.

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