Guesterly's Rachel Hofstetter: What it's Actually Like Starting a Business
When Rachel Hoffstetter said “I do” at her wedding, it wasn’t just a marriage that was formed—it was a business.
Hoffstetter and her husband had printed short, fun magazines featuring each of their guests to help ease introductions during the day, an idea that quickly caught on with their friends and family. Soon, the couple found themselves fielding requests from others eager to add that special touch to their ceremonies, and Guesterly was born.
But Hoffstetter readily admits that starting a business—even one centered on weddings—is far from romantic. She is the first person to tell you just how tough it is, which is why we think she is the perfect person to turn to for advice.
We caught up with Hoffstetter in her home-slash-office to find out what it’s like having your husband as a business partner and her best advice for others looking to create their own careers.
Before starting Guesterly, you kept busy as the food editor at O, The Oprah Magazine, and you wrote a book, Cooking Up a Business. With an already fun and challenging career, what made you want to take on something new?
I think a lot of things came together at once. The first was writing my book, Cooking Up a Business, which is about all these awesome food entrepreneurs—people I consider heroes both then and now, people who started from nothing but had an idea and decided to do it.
Being food editor for O, The Oprah Magazine, was a fantastic job, and writing a book was just a part of that, it was my big side passion project. But while it was supposed to be a passion project focusing on the food, it turned out my interest was more in the entrepreneurship side of it.
The second major thing that happened was my wedding, where my husband and I first created the concept that became Guesterly. For our ceremony, we created mini magazines with pictures and fun bios of everyone there to help people really get introduced and get to know each other. It made our wedding feel that everyone knew each other, and it had that feeling of old friends. And while we had created it just for ourselves, soon our friends were calling us and asking us to do it for them.
Was there a moment you realized that your idea could really become a business?
I think the “aha” moment for us came when a friend of a friend, someone we didn’t know, called and said, “Hey, I saw this at Zack’s wedding, I would love to do it at my wedding, and I’ll pay you.” That was when my husband and I realized we had something people are excited about and willing to pay for. Starting a business is full of so many uncertainties and so many unknowns. That’s really all it is—startups equal uncertainty! But now, we at least knew one thing—we had an idea people were excited about that, an idea that no one else was doing. It turns out that there were about a million other things we didn’t know, but we knew those, and so that’s really when we decided to give this a try.
People are often nervous to enter into a business with a significant other or close friend out of concern that it will affect the personal relationship. Was this a conversation you and your husband had?
I’ll be totally honest, we did not have that kind of conversation. I think I just knew that he was somebody I trusted a lot. My husband, Lorne, had a side business along with his full-time job that I did marketing for, and he’d helped me edit my book, so we had definitely been involved in each other’s side projects. But when it came to Guesterly, we didn’t have that “big talk.”
What we did have was a discussion that we would put a small amount of money into it and three months. We had a date set—July 15—to have a sane conversation and reevaluate. We were completely ready to basically stop doing it if it wasn’t getting traction and people weren’t getting excited. So, we did have a pause date and the feeling that we were doing it on a very trial basis. Luckily, on July 15, we had so many orders that it was a fast conversation!
Lorne and I started this in our first year of marriage, so we still haven’t even gone on our honeymoon. This is definitely not the normal way to do things! Still, we try to set it up that one afternoon a month, we’re 100% off, and we made a promise to ourselves that we will go on a honeymoon this year. A lot of it comes down to the fact that we are both all in this. What I think would not work is if one of us was doing a startup right now and one of us wasn’t—I think that would be really hard. And while it feels like our whole life is Guesterly, it’s kind of amazing that we’re able to do that, to build something together.
I love this idea of setting a date for yourself to really check on your progress.
It comes from a belief I have, which is not to worry about something until you need to. This is something I started doing when I was searching for my first job. I said, “I’m not going to worry about this for six months,” and I was able to really put my heart into the search. What setting a date does is keep you from having that daily up-and-down roller coaster of worry, because that feeling does nothing to help when it comes to making big decisions.
You and your husband work out of your apartment. How are you able to separate your Guesterly life from your personal life with this setup?
We’re really lucky that we have an extra bedroom that we turned into the office. I think without that, this would not be a possibility whatsoever, because at least this way, I can close it off. We only work in the office, we don’t bring our laptops out into the living room, for example, and we try to keep the door closed.
I won’t lie; it is all encompassing right now. We are in the stage of the startup where it is our life, and my definition of sane right now is very different than it has been the rest of my life. The way I see balance right now is that sure, I’m going to go through two or three years that are really crazy, but I’m trying to build it up so that over the next 10 to 15 years I have more balance, more control over what I do. It’s almost like I’m frontloading my investment right now.
With the knowledge you have now, what advice would you give to someone who has an amazing idea like Guesterly and wants to take the first step toward building a business?
Try putting it out there in a small, side-hustle way. I’m a big advocate of not leaping completely. Having a job really is an amazing thing—I 100% took it for granted! So, I think there’s a lot to be said for what you can do on the side, whether it’s writing or baking or blogging. In our case, we did it for our own wedding and then our friends’ weddings, so it let us see if it was something people really do want. Once you know people want it, you can make a much more educated decision of what to do next.
Photo courtesy of Pinsi Lei.
As a freelance multimedia journalist, Colleen has spanned the globe with her camera in hand to share unknown, interesting, and inspiring stories. Some of her most recent pieces have taken her from Thailand, where she spent a night on an uninhabited island, to Australia, where she covered a rare disease affecting Tasmanian Devils. She started her career at NY1, reporting on major stories including Hurricane Sandy and the 2014 mayoral elections.More from this Author