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Why I Started a Second Business When I Was Getting my First One Off the Ground

Rachel Hofstetter  |  April 23, 2020

Starting a second business can be daunting, especially when your first is still growing. But sometimes two is better than one.


“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.

The first time

When my co-founder and I came together in 2013 and started guesterly, an online platform to create digital and paper books that wow guests and make a lasting impression, we made a pact that it would be our sole business priority for the foreseeable future. We would write down all the new business ideas we would come up with — and then never look at them.

Most of the time, this “out of sight, out of mind” strategy worked for us. Starting a company takes 2% idea and 98% 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).

How I started my second business

But knowing all that, I nevertheless went ahead with my next venture. I launched a completely new business while my first child was still a needy, on-the-go toddler. 

Here’s why it worked — 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. Then, 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 scored more than 100 major stories in a single 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 would 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 would each bring our own strengths, network, and enthusiasm — with less risk, time, and stress. And by joining forces, we could go fast. We launched Savor PR School just three months after our initial conversation.

Multiple businesses have different structures and timelines. Savor PR School and guesterly had very different models, which means they worked well together. Savor PR School is a low-tech, high-expertise product that could start generating income relatively quickly. On the other side, 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 created cash flow in the short term let me grow the business that had more delayed returns.

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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.

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Editor’s note: We maintain a strict editorial policy and a judgment-free zone for our community, and we also strive to remain transparent in everything we do. This post contains references and links to products from our partners. Learn more about how we make money.
Editor’s note: We maintain a strict editorial policy and a judgment-free zone for our community, and we also strive to remain transparent in everything we do. Posts may contain references and links to products from our partners. Learn more about how we make money.

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