Why I'm Starting a Second Business — When My First One Is Still a Toddler


“Get one thing right.”
“You can be a serial entrepreneur — after you sell your first company.”

All good advice, and mantras of many a startup scene. The fast-paced worlds of tech and consumer startups are all about laser focus and fast execution — meaning you have one business, one product, one goal. That’s what I used to think, too.

When my co-founder and I started guesterly about a year and a half ago, we made a pact that it would be our sole business priority for the foreseeable future. We write down all the new business ideas we come up with — and never look at them.

Most of the time, this “out of sight, out of mind” strategy works. Starting a company is two percent idea, 98 percent execution. A great idea is (literally) nothing without the hard work of building the product, marketing, and sales — not to mention the nitty-gritty of regulations, taxes, insurance, and the other non-glamorous roles of entrepreneurship (ahem, taking out the office trash).

But knowing all that, I’m nevertheless going ahead with my next venture. I’m launching a completely new business while my first is a needy, on-the-go toddler. Yet I’m more fulfilled, having more fun, and my first business is benefiting. Here’s why it works — and how you can make it work for you too.

There’s a natural affinity or expertise. Adding a second business should feel so organic that it’s almost impossible not to do it. Launching guesterly required me to take a huge leap, from magazine editor and author to tech entrepreneur. I felt like a butterfly struggling to get out of a chrysalis every day — everything was that new, and I was having mindset shifts like other people have breakfast. But as we grew, I discovered I had a natural affinity for getting press: I use my “editor brain” to give editors and writers exactly what they need.

Soon I was helping my entrepreneur friends do the same, and then getting referred to friends of friends. By last summer, I was spending an hour or two a day consulting (gratis, of course!) and creating PR strategies for a range of businesses. I never thought of it as something to monetize. But it continued to build: I crafted a DIY PR guide to share, and started asking editor friends for insider opinions. That’s when a friend suggested we could make this service bigger.

1 2