Why the Second Time Isn't So Easy Either Even when your first business thrived, there's no guarantee the second one will enjoy the same success. But the work is worth it.

By Greg Shugar

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.


"So...how are sales going?"

"Have you had any write-ups in the media yet?"

"How long will you run this before you sell the company?"

These questions, on their surface, don't seem unusual. They're certainly the types of questions you might ask any established business owner. But they seem a bit premature to ask someone who launched a business just three days prior, right?

Apparently I'm wrong.

Within three days of launching my newest business, Thread Experiment (the first ever home bedding brand for men), I fielded these questions and others like it from friends and colleagues.

In some ways, I was flattered by these questions because it assumed I would be successful.

But in other ways, it made me feel more pressure because…it assumed I would be successful.

Some background for you:

Me 1.0

Back in 2004, my wife and I started a quiet little "business' in the basement of our Chicago home. We tried designing and selling neckties over the interwebs. We called it The Tie Bar. A crazy idea back then.

I was a full-time practicing attorney. She was a young mom. We borrowed the last bit of equity from our home to start the business. We did all our work late at night when the kids were sleeping. We did everything ourselves. We had no idea what the hell we were doing. We had fun.

Related: Get Your Product Figured Out First

Over the next nine years, we would grow this company to nearly $20 million in annual revenue. Along the way, our friends cheered us on and sat as surprised as we did as The Tie Bar grew into a household name for men's accessories. Every new achievement felt great. Every press mention flattered us. Every happy customer made our day.

Over the years, we expanded our product line and sold virtually every kind of men's fashion accessory you can think of. Our products graced the covers of several GQ magazines, and male celebrities all over Hollywood were wearing our products.

By 2013, we were acquired by a private-equity firm. We like to tell people we were an overnight-9-year success.

Read that last sentence again – because that's the point of this column.

Me 2.0

After being bought out, we moved to Florida where I quickly grew tired of playing tennis every day.

Eventually, I thought up an idea for a new business and found two partners to join me. After 16 months of hard work, we finally launched our startup in May, fully bootstrapped.

And this is when those questions started pouring in.

"So...how are sales going?"

"Have you had any write-ups in the media yet?"

"How long will you run this before you sell the company?"

As much as I'm flattered by these questions – it assumes Thread Experiment had already taken off like a rocket in just three days – they are also a bit unfair.

Related: Your New Brand Should Be an Extension of Yourself

The Reality

Let me clarify – I am loving this startup thing. As The Tie Bar grew, things started to come easy. Way too easy. I no longer had to pitch a reporter about our company. I no longer had to hope we'd make payroll. I no longer have to do any of the grunt work – I had a staff doing that.

And that's all great. But the truth is, I prefer it the other way.

I love building a brand from scratch. To do all the grunt work myself again. Yes, I have to cold-call people and give them my pitch – but I love that, too.

We are a startup. With the exception of a few "lottery winners,' most startups take time – a lot of time – to get any traction. Like years.

In three days, we launched our website. Began our Google AdWords campaign. Our Facebook Ads campaign. We've pitched the media. We've reached out to retailers. We started our process with Amazon.

But whatever I accomplished with The Tie Bar has no bearing on whether Thread Experiment will succeed. Thread Experiment will be judged on its own merits. Its own products. Its own brand.

And it will need its own luck. Its own good fortune. Its own lessons.

Which means that this startup can fail just as likely as any other. And I'm fine with that.

But I'm not sure my friends and colleagues are.

We all know those statistics about how few businesses even survive for one year. So even if I am lucky enough to last more than a year, I then need patience to grow. Patience to let my startup germinate.

There's a saying that I've heard time and again: Do it once, you're lucky. Do it twice, you're good. I tend to agree with that saying. And I'll do my best to prove I'm good.

Just give me a little time.

Related: Stop Pretending and Just Be Yourself

Greg Shugar

Co-Founder of Thread Experiment

Greg Shugar is Co-Founder of Thread Experiment, the world’s first brand of home bedding dedicated to men. Greg originally founded The Tie Bar and grew it into a $20 million business before a private-equity firm acquired the brand. Greg is now CEO of Shugar Consulting, which specializes in helping new retail brands emerge in the ecommerce and wholesale space. He also regularly speaks on topics related to entrepreneurship and teaches an Entrepreneurship Bootcamp course at Florida Atlantic University. Prior to launching Thread Experiment and The Tie Bar, Shugar was a practicing attorney in Chicago for eight miserable years.

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