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.

Don’t go it alone. My friend Angela Jia Kim is a PR whiz herself. Her three companies got more than 100 major stories last year alone. We asked ourselves: “What if we created a PR school and made this information available to everyone?” Soon we had a win-win plan. We’d piggyback off Angela’s Savor the Success website, team, and sales channels; I’d get top editors involved as mentors; and together we’d craft material. We each bring our own strengths, network, and enthusiasm — with less risk, time, and stress. And by joining forces, we can go fast: We’ll launch Savor PR School this January, just three months after our initial conversation.

Multiple businesses have different structures and timelines. Savor PR School and guesterly have very different models, which means they work well together. Savor PR School, a low-tech, high-expertise product, will generate revenue in months; guesterly involves high-tech, patent-protected software and a long-lead sales channel (most of our leads are for events a year out!). Having a business that creates cash flow in the short term lets me grow the business that has more delayed returns.

Stagger workloads and cross-pollinate. When one company goes through a slow period or has a bad day, the other is there — it’s the startup equivalent of dating a few people at once. And there’s more variety to keep things interesting. Another perk: A strategy, suggestion, or research project for one business often generates an idea for the other. As a bonus, it’s made me better at organizing and prioritizing.

You have more fun. Stepping on the startup carousel for the second time is way more fun than I ever expected. Just like a second-time parent, I barely realized all the insight, confidence, and mentors I picked up on my first go-round. And now I get to “play business” in more areas that I’m passionate about, and work with more of my favorite people. Two really is better than one.

For years, Rachel Hofstetter (@rachelhoffy) was a food editor at places like O, the Oprah Magazine and Reader’s Digest. Besides copious amounts of chocolate and cheese, her favorite part was talking with up-and-coming food entrepreneurs. Their stories led to Cooking Up a Business, a book about food startups, which gave Rachel the entrepreneurial itch. She left her editor career to launch guesterly, a software platform that enables anyone to create a custom event playbill. Now she’s combining her two worlds into Savor PR School, an A-Z guide to getting great PR.

This piece originally appeared on DailyWorth in January 2015.

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