Connecting Through Guesterly

You can laugh at me, but honestly, I kind of thought I knew what a startup would be like. And you don’t until you do it — like many, many things in life.

As a man who talks with startup people for a living, I can definitely say that the term “pivot” gets thrown around with annoyingly reckless abandon. Most use it to describe a subtle shift in product or philosophy, a unit of measurement that weighs the changes moving a person from point A to point B. This does not interest me. The kind of pivoting that interests me is the drastic kind, a wholescale movement that immensely alters the course of a person’s life.

This is a story about pivoting. Not the type that every startup CEO claims they’ve made, an overused statement that numbs the ears and dulls the brain. This is the story of an honest-to-God, life-changing, opposite-ends-of-the-spectrum pivot and you have my promise that it will be neither dumb nor dull.

As a woman who used to talk with startup people for a living, Rachel Hofstetter heard untold stories of how hard (yet rewarding) the startup creation phase can be. Living in New York, Hofstetter worked as the food editor for Oprah Magazine, interviewing various entrepreneurs about their inspiration and reasons for starting a business. When the articles she was writing struck a chord with readers, Hofstetter parleyed the groundswell of support into a book deal and published “Cooking Up a Business: Lessons from Food Lovers Who Turned Their Passion into a Career — and How You Can, Too” in December of 2013.

“So I have these really in-depth interviews with CEO’s, just hours and hours going through their business and telling their story, but also find out what worked, what didn’t,” Hofstetter said. “By the time I finished writing the book, I was like, ‘I want a business, where did this come from?’ I had spent so much time learning how they did it, I felt like I had my MBA in startups just because I had researched it so extensively.”

As if writing a book wasn’t life-altering enough, Hofstetter was also getting married. Worried about creating the ideal wedding atmosphere, she began bandying about ideas on how to create a comfortable bubble for all the wedding guests to dwell within.

“My husband and I were getting married and kind of like everyone who gets married realizes, it wasn’t all about us,” Hofstetter said. “It’s about our friends, family, and heritage all coming together. I’m from Ohio, my husband is from Idaho, we were living in New York and everybody was coming in for this wedding. So our highest priority was, how do we connect all these people that are coming together for once in our life?”

From this mix of marriage, people, and desire to connect, the first guesterly emerged. Roughly based on college lookbooks, Hofstetter created what amounted to a souped-up, personalized event guide — each attendee was highlighted with a picture and a blurb, then copies were printed and mailed to each of the wedding guests before arrival. Instead of showing up not knowing who was who, guests could browse the pages and familiarize themselves with everyone in a fun, interesting way.

“We have this concept of a book directory that connects everybody,” Hofstetter said. “People want to learn things about other people, they want to connect to other people, and they want to discover new people. It’s totally different from going onto a Facebook group where you see a few other people. They want to discover fun facts — instead of reading a program, they want to flip through a book and discover who all these cool people are so they can get to know them. So that’s really where our ride started.”

Needless to say, the first guesterly was a massive success. Guests ranted and raved about it, to the point that Hofstetter soon was bombarded by requests to create guesterlys for other people’s weddings. She obliged, soon realizing this idea had legitimacy that could evolve into a full-fledged business. Guesterly was officially born.

Now, this is what we call a full-fledged pivot — Hofstetter entered as an unmarried woman writing about entrepreneurs and emerged as a married woman who actually was an entrepreneur. But the beginning was not without trial and error.

“We started running it as a custom-design shop and what we learned very quickly, while it sounds cool to run a custom-design shop, that wasn’t the business model for us,” Hofstetter said. “We were losing money on every job left and right. So we might have $30,000 of revenue come in, except the cost of getting it sold might be $34,000. It doesn’t take a rocket scientist to realize, not a good business model here. But what it did tell us was people wanted this concept.”

When you’re losing money, you go back to the drawing board and start anew. That’s exactly what happened, with a brand-new, software-based guesterly emerging last year. It was initially launched in the wedding market, but has since grown to encompass any event or get-together one could possibly think of. Let’s say you’re planning a wedding. You obviously want all you guests to be familiar with one another before arriving, thus avoiding any awkward encounters between unacquainted individuals. Here’s what you would do: create a guesterly (available in print or digital), create specific questions that you want each attendee to answer, then share the link via email where everyone can answer on their own time. Responses and pictures are then funneled into your very own guesterly, automating the process and creating a unique, funny, event guide for all to enjoy.

“We have something that is so much bigger than hand-designing a custom magazine,” Hofstetter said. “That’s not what we’re about. We’re about making this concept of a directory for any event and any group accessible to everyone. And it should be completely affordable. As an entrepreneur, you know you’re going to iterate, but then you get knee-deep in it and it’s amazing what can happen. The coolest part for me is finally having hit upon exactly what people want.”

You know of the sweet, sweet fruit that Utah’s startup scene can offer. Hofstetter does too, and that’s why she moved herself (and her business) to Salt Lake City in autumn of last year, intent on growing guesterly to Mount Timpanogas-sized proportions.

“We love New York, New York is a great place to be, but there’s also other awesome places to build startups,” Hofstetter said. “In many ways, Salt Lake has everything you want. There’s a huge pipeline of developers, there’s a lot of talent, even things like DevMountain — our junior developer came out of DevMountain — you can’t find an accelerator program like that anywhere else. It’s just a really solid place to build a business.”

Life comes at you in funny ways. We all dream of certain things but many times, we can’t fully comprehend the dream until it’s directly in front of us. Rachel Hofstetter used to write about entrepreneurs for a living. She heard their stories and realized that, in turn, she longed for the emotional rollercoaster of an early-stage startup. But it wasn’t until the first guesterly that she fully realized her dream — being able to connect people.

“You can laugh at me, but honestly, I kind of thought I knew what a startup would be like,” Hofstetter said. “And you don’t until you do it — like many, many things in life. But I wouldn’t want to be anywhere else. There are so many things that we do in life where we talk to people we already know. It’s easier that way. But it’s the people that you don’t know, and that you don’t even know you need to know, that really affect your business and your life. We all need to know the people in the periphery of our networks. We just help you do it in a fun way.”

Published 9/28/2015

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