Home Advice For The Young At Heart 6 “Don’ts” Of Starting A Successful Business

6 “Don’ts” Of Starting A Successful Business


by Tom Silk, Executive Vice President at WorkStride

key-to-successI’ve always believed that the best lessons are learned through experience rather than in a classroom. And unfortunately, the best of those life lessons usually comes from failures or near-failures, when you’re forced out of your comfort zone. It’s at those moments when you feel like you’re doomed that you’ll often come up with your most creative solutions.

I started as a sales representative more than 15 years ago at WorkStride, where I am now EVP of Sales and Marketing. I’ve seen the company go through ups, downs, more ups, near failure, acquisitions, and incredible growth.

Through this, I’ve learned some things you truly can’t learn any other way than the hard way. Hopefully I can save you a few bumps along the road with these tips:

1. Don’t Be Afraid to Be Different.

When you start your business you’ll be tempted to look around and reassure yourself that what you’re doing is right. You might get nervous if you notice that you’re taking a different path than the more established firms in the industry. For us at WorkStride, that was absolutely the case. We started the business based on a model that made sense to us at the time as a motley crew made up of a lifelong ad executive, a former mortgage salesman, and a professional investor. Like George Costanza, we proceeded to “do the opposite,” and it worked in our favor. Clients responded to our fresh approach and it continues to be one of our differentiators today.

2. Don’t Limit Yourself to Your First Vision.

When you first start your business you’re going to be really passionate about doing whatever it is that you set out to do in a certain way. Then one day you’re going to get a phone call from someone who is willing to pay you a lot of money to do it. There will be a catch though — they will want you to change some things to accommodate them. At the early stages of your business, I advise you to say “Yes” and then immediately hang up and figure out how to make it happen. We did it, and our product ended up evolving as a result. Plus, we still have that customer to this day because we have grown with them.

3. Don’t Stop Looking Ahead.

Eventually, there will come a time when scrambling will pay off and turn into stability. You’ll be tempted to ride it out and just enjoy your success for a while. I advise you to pat yourself (and your employees) on the back, have a glass of champagne, and then get back to work, because this is the time to look ahead! New competitors can pop up daily, the business landscape changes, and next thing you know, you’ll be sprinting just to catch up.

4. Don’t Go It Alone.

When you’ve raised such a beautiful, smart baby it’s hard to let someone else help you take care of it — I know. But sometimes the best thing you can do is bring in someone else who has been where you are trying to go, whether that’s the top of your local industry, or the Fortune 500. A more experienced partner can provide a wealth of new perspectives and unlock possibilities for your company that you could never dream of. When the Riverside Company purchased WorkStride a few years ago, Jim Hemmer was installed as our new CEO. He called us a “six foot two-year old” at the time. We were growing rapidly, doing great work for our customers, but we did not have sufficient coordination or processes to sustain growth. Jim came in and provided that structure we needed to grow in a scalable fashion.

5. Don’t Shy Away from Alternative Funding.

Traditional investors and funding strategies will probably be the first place you’ll look when you need capital. If you fail at attracting these investors or you don’t like their terms, remember that they aren’t the only options out there. Private financing is another source that is rapidly growing in popularity, and these investors are often less risk-averse than their traditional counterparts. Once upon a time, WorkStride attracted over 20 private investors with a well-placed New York Times ad!

6. Don’t Forget That This is Fun!

I often tell a particular story at company meetings, especially when employees perceive that times are challenging. For them challenging means we’re swamped on implementations, or we’re low on headcount. These are great problems to have!

The story is this – I spent a Saturday in the early days of WorkStride on the phone with Fed-Ex literally running down one of their trucks in the middle of Manhattan. Why? Because that truck contained a client payment check that would ensure we could make payroll on Monday and it needed to be deposited before the bank closed. Those were the hard times, but they’re also the times that I wouldn’t trade for the world. So try to enjoy them now, even if you’re a little out of breath.


Tom Silk

Tom Silk is the executive vice president of sales and marketing at WorkStride. He joined the New York City-based company in 2000 as its first salesperson and quickly rose to Executive Vice President of Sales and Marketing. In 2012, he facilitated the company’s sale to The Riverside Company. Silk has a bachelor’s degree from the University of Massachusetts, Amherst.