Unfulfilled Despite a Dream Job at Google, This Bay Area Founder Built a Startup to Cure His Malaise

By most standards, Eric Winters had it all. At a young age, he’d secured a high-paying and flexible job in the Bay Area at Google, managing some of the firm’s largest acquisitions.

But Eric had a problem: He wanted to create a startup but lacked a cause. He quested for years to find his calling be it training for the NFL Combine or teaching himself to backflip. Eventually, he realized he wasn’t missing skills but a community outside of work. 

Eric and Google software engineer, Brandon Pearcy, bonded over their desire to make better communities by constructing an app called Heylo. Originally focused on sports groups, it grew to serve gatherings of all types from social to religious. Its goal is to help people create the communities they desire by focusing on those who make them possible: group leaders.

Today both founders no longer work for Google. They run a profitable business helping leaders organize groups, manage them, and collect payments. Most impressively, they’ve raised zero capital despite their Google reputation (VCs love startups run by ex-Google employees, Eric says). 

What Is Life Without Passion?

Eric says that deep down, he always wanted to be an entrepreneur. Because of that desire, he left school and went to work on Wall Street from 2008 to 2013 during some of the industry’s toughest years. He believed the experience in business would help him when he eventually started his company.

He left Wall Street but not for entrepreneurship. Eric took a coveted Principal Corporate Development job at Google in 2013. In that position, he’d court entrepreneurs in the Bay Area and recommend them to Google for investment or acquisition. He helped broker deals with SpaceX and Motorola in his time.

I realized I’d created my career to stay close to entrepreneurs. I just loved these types of people. I loved spending time with them and I wanted to be like them.

Eric loved the autonomy and pay at Google, but it only substituted his greater passion. “I realized I’d created my career to stay close to entrepreneurs. I just loved these types of people. I loved spending time with them and I wanted to be like them.” 

He searched for something he was passionate about to turn into his business. Unfortunately, he’d spent so much time working in corporate roles after graduation that he’d forgotten which things he loved to do most outside of his social circle. “When I was doing these corporate jobs, I didn’t have anything I was interested in doing outside of work, friends, and family.”

Eric spent the next several years developing his hobbies and interests. He spent a year training for the NFL combine (though he didn’t participate), and practiced backflipping in his mornings before work. 

Eric liked these activities but realized they were missing the crucial element that makes them fun and rewarding: a community.

“I had this moment at eight in the morning when I first successfully did a backflip. I had a meeting I was supposed to run to after. I was in this beautiful field with a mountain view and I looked around and thought, ‘I’m a grown man and I’m by myself trying to backflip.’ Doing it solo just was not a great experience. That kicked off my passion for understanding how people come together.”

Now that Eric realized he missed connecting with his peers, he ran around San Francisco to attend different group events and sports meet-ups. Initially, he did not enjoy the experience.

“Going to one of these online meet-ups for the first time is terrible,” says Eric. “It always looked like everyone was having a great time and then I’d show up and stand awkwardly to the side. Even worse was when I’d show up and no one was there. Eventually, I got used to being new in these groups. However, I knew this was hard for other people too. I wanted to start a group and see what that was like.”

Eric eventually found and founded a handful of communities, including a volleyball club where he felt he belonged. However, those long months of searching proved these connections were exceedingly rare. He wanted to create an application that helped people turn their groups into communities.

Eric realized his dream through his friendship with now cofounder, Brandon Pearcy. Brandon had worked as a software engineer at Google for twelve years on products like Maps, Ads, and a Google division called Infrastructure. He was also the perfect example of the immersive power of groups.

“What’s unique about Brandon is he’d spin up all sorts of projects within the organizations he worked at. He was an organizer for a breakdancing club, a Muay Thai group, and a beach volleyball club at Google. He created these groups and they made him feel like he belonged in America (he’s from Canada). We were on the same page from the beginning.”

Measuring Success Through Connection

The first version of Heylo was an app called Piccup. Eric and Brandon soon changed the company name when people said it sounded like the name of a dating app.

“One of our early beta testers said, ‘This app is awesome, but I just went on a date last night and I received messages on the Piccup app. I then had a weird convo with my date about why I was receiving messages from a dating app. I had to explain it was for my running group.”

Heylo’s beta expanded primarily through word of mouth. They introduced the application to sports and fitness group leaders who shared it with other group leaders. Traffic grew slowly, with a handful of notable spikes.

“At one point, our active users went off the charts and we thought it was a glitch,” says Eric. “It turned out there was a guy in a run club who sent a goodbye letter to his group saying he was moving. He talked about how grateful he was to find this community because it had helped him get in shape and feel more confident in himself and many logged in to respond. That kind of thing doesn’t get shared in an email chain or a one hundred-person Whatsapp chat.”

That goodbye letter was exactly the type of connection Eric wanted Heylo to create. Encouraged, he joined groups on the app in his free time and realized he could use the features for much more than sporting groups. The connections between people outside of the events were almost more important than the events themselves. Customers engaged because of these connections.

“We create a lot of qualitative value for people. They might use Heylo to play sports like volleyball but make other connections in the group. Maybe someone lists that they work in real estate on their profile. They’ll suddenly have people reach out to them on Heylo because they’re looking to buy a house in the area. Maybe at a group event, they hear about a group canoe trip on the weekend. It’s a place to meet new friends, find new roommates, or even find romantic partners.” 

Soon, Eric and Brandon acquired enough active groups to begin monetizing the app. It took a lot of soul-searching for both of them to finally leave their jobs to focus on Heylo full-time.

“I got to a point where I couldn’t stop thinking about this,” says Eric. “I couldn’t go to bed because I was writing notes about it every night. I left a few weeks before Brandon in 2018 and then he agreed Heylo was way more fun and joined.”

Eric and Brandon added small fees to platform payments and grew the business through 2019 – then Covid restrictions locked it out of the market in March of 2020.

All of a sudden, it wasn’t safe to host your events. You had to be an infectious disease expert to plan a volleyball game.

“During the pandemic, groups went through the biggest disruptions since probably World War Two,” says Eric. “All of a sudden, it wasn’t safe to host your events. You had to be an infectious disease expert to plan a volleyball game.”

They kept working on Heylo through lockdowns despite no revenue. The cofounders talked about pivoting the business but a handful of groups still used Heylo. They couldn’t leave them behind.

“Those groups stayed together during the pandemic because of Heylo and we loved them,” says Eric. “We made a bet that real-life groups would come back and found a way to generate revenue through payments in the meantime. We eventually generated a profit and now those groups are thriving.”

Betting on the return of in-person groups left Heylo in a perfect position as San Francisco reopened and cooped-up professionals started to look for new places to socialize. Their app offered countless fulfilling communities in the region.

“Trying moments like that make you question everything,” says Eric. “What helps is having a great cofounder and supportive people around you. Just show up to work every day and eventually something great happens.”

Leaders Are a Group’s Most Valuable Asset

While Eric is proud of Heylo’s organic community creation, his main focus is on group leaders. 

“These groups don’t exist without leaders but they lack software built for them. These are the people creating the experience, and they’re woefully underserved and undercelebrated.”

Heylo gives leaders the tools they need to run groups more effectively, such as an intuitive and unintrusive system for collecting payments from group members.

“Leaders don’t want to be the payment police,” says Eric. “We help them either put up paywalls to participate or we help them leverage social status to encourage members to make payments and contributions. That way, the community leaders get the resources they need to deliver incredible experiences. Also, when people pay they are more engaged and it creates a better experience for them.”

Members can easily make digital payments for group formats like membership clubs, coaching, and paid events. Leaders get money deposited into their accounts every Friday minus the small percentage Heylo takes for monetization.

“We don’t serve you ads when you’re messaging or scrolling. We make money betting you find value in being part of a community,” says Eric.

The World Needs More Great Groups

Eric says that the future for Heylo is straightforward: They want everyone to belong to a fulfilling group.

“Groups went through challenging times in the past few decades due to our increasingly online world and Covid. However, we think everyone should be part of a community for the rest of their lives. Unfortunately, we don’t have enough truly great ones out there today.”

For founders trying to make similar projects, Eric’s primary advice is to be careful whose advice you listen to. Many people have opinions, but few have the perspective you need to succeed.

“You’ll never have trouble finding advice. I often got bad advice when I was starting Heylo. Many said we should go raise money since we were both ex-Google. I can’t tell you how many people I have seen do that and not create value.

If you can survive bootstrapping your startup, no one will question your grit as a founder.

“We needed to go in, struggle, and eat ramen. We needed to be obsessed with our customers. I’m glad we didn’t spend our first three months with a pitch deck and an idea and instead focused on talking to the people who would use our app. If you can survive bootstrapping your startup, no one will question your grit as a founder.”


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Andrew Gazdecki
Andrew Gazdeckihttps://microacquire.com
Andrew is an award-winning serial entrepreneur with three exits. He’s the founder and CEO of MicroAcquire, the world’s most founder-friendly startup marketplace, and its rebellious child, Bootstrappers, which gives voice to the entrepreneurial underdog. When not building businesses, he writes for Forbes, Entrepreneur, and now, Bootstrappers.

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