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Can Late-Night Conversations Result in Successful Startups? Yes – Just Don’t Give Up On Them, Says Jake

Growing up, Jake Aronskind and Matt Schkolnick spent hours kicking back in the shed behind Jake’s house in Short Hills, New Jersey. The childhood friends stayed up past midnight sharing off-the-wall ideas for million-dollar businesses. Only Pepper the App would succeed.

In July 2019, Matt started a late-night conversation about one of his college GroupMe chats. Every day, people shared cooking pics and meal updates. Sometimes people would ask for the ingredients or recipes, but these messages got lost among 100s of daily posts. 

Jake and Matt wondered why food content was stretched so thin. You might post flashy meal photos on Instagram or a mid-cooking update on Snapchat. Or turn to Pinterest for cooking inspiration and Facebook for Grandma’s family recipe. But what if there was a social media app where you shared your love for food and recipes?

Today, Pepper the App helps around 500,000 foodies share photos and recipes of their meals with friends or a global audience. You can search for recipes, interact with fellow chefs, and keep track of your favorite dishes. 

Read on to discover how these 23-year-olds executed a haphazard plan that turned a budding business idea into one of the top Food & Drink apps on Apple’s App Store. 

The Shed: A Hub for Ideation

Jake Aronskind’s backyard shed was the neighborhood hang-out spot for play and roughhousing before becoming a pseudo think-tank for teens. It’s where he and Matt developed the idea for Pepper and hundreds of other half-baked ventures. 

The boys became fast friends at a summer camp in Pennsylvania when they were under 10 years old. Jake learned Matt lived just 15 minutes away from him in New Jersey, and the pair spent years playing in their backyards and listening to stories from Jake’s father, Ofer.

Ofer Aronskind moved from Israel to the United States as a child in the 1970s. His family owned a summer camp and vending machine business. Ofer passed those entrepreneurial instincts to Jake (and Matt), encouraging them to listen to business podcasts like Guy Raz’s How I Built This.

The shed became Jake and Matt’s creative sanctuary throughout high school and college. And although they went to different universities (Jake at Vanderbilt and Matt at Penn State), they’d return to that spot every school break.

Jake and his friends decorated the shed with cool finds from garage sales, thrift shops, and their own attics. 

After graduating in 2019, the pair decided to move to New York. Jake wanted to become an equities trader for Trillium Management while Matt pursued his master’s in accounting at Rutgers University. But in the meantime, they started outlining a Google Doc titled “Cookbook” with different features for an app. Like Instagram, users would scroll through photos of food, but the posts would also contain ingredients and recipes. 

When Jake told Ofer about their idea, his father said to go for it: “Your twenties are a good time to take risks,” he said. But before Jake could move forward with the app, he started his full-time job in New York while Matt stayed behind in New Jersey to start his master’s program. 

Exploring the “Perfect Intersection of Product and Timing”

When the pandemic hit in March 2020, Trillium sent Jake and the other traders home.

“I had a lot of time on my hands, and I would see so many of my friends posting pictures of the food they cooked at home on their social media,” Jake says. “Sourdough bread was the first trend of the pandemic. Then Matt’s and my idea for social media for food came back to me.”

He called his childhood friend in April 2020. Matt reportedly remembers the beginning of this conversation word for word. Jake said to him, “Matt, remember Cookbook? I’m moving forward with it. I want you to be part of it with me.”

At the time, Matt was struggling to finish his master’s degree and balance a full-time job as a CPA. He recalled the hours he and Jake spent pitching off-the-wall business ideas in the shed –  sixteen-year-old Matt wouldn’t hesitate to start a business with Jake.

One week later, Matt and Jake coined the name Pepper and started writing a business plan while Jake was stuck at home. 

“I knew we would all come out of this pandemic differently. One difference I noticed was socializing in verticals,” Jake says. “Examples include Strava for exercise and Goodreads for reading. The rise of verticals was obvious to us, plus people posted different things on their Instagram story than they do their Snapchat.”

He adds, “The start of the pandemic was that perfect intersection of product and timing. Pepper was the one idea where we said, ‘Hey, let’s go make this thing.’”

Don’t Underestimate the Power of Connections 

Before bootstrapping, Jake and Matt pitched investors for funding as their meager savings wouldn’t stretch to build an app – not even a prototype. But by the end of summer 2020, they’d had enough doors shut in their face to realize bootstrapping was their only option. 

“Investors said, ‘I wish you had tried building something else before because I would believe in your mission ten times more.’ Which I think is ridiculous,” Jake says. “But I also get it. Second-time founders are more likely to succeed. The experience I’ve gained from building this first startup is unbelievable.”

With only Jake’s sketches of a potential newsfeed, investors couldn’t get their heads around the opportunity. 

Jake designed early concepts of Pepper the App during his and Matt’s brainstorming sessions.

“The biggest issues were getting to different milestones. To get further and further away from, ‘Who are you guys?’ to ‘What are you building?’” Jake adds. 

The investors didn’t believe in Jake and Matt’s vision, but their friends and family did. The cofounders raised two funding rounds from their loved ones to build a prototype and an iOS app. 

Twenty-four hours after advertising for a developer, Jake and Matt heard from Boon Chew of Tappalo Media. Boon not only came from a stellar developing background (working on apps like iHeartMedia and DiscoveryGo) but he also loved Pepper’s concept. When the founders saw Boon’s vision for the app’s backend, they had to have him. 

They also needed someone to design the app’s front end. Eli Silverman was a friend of a friend who now runs Pepper’s product department. Back then, he focused on tailoring the app’s visual appearance to improve user experience. 

Although the cofounders couldn’t afford more paychecks, they recruited more people with equity in the company. Matt’s brother and his friends helped with marketing, including the current head of growth marketing, Kayla Menkes. The cofounders also hired a college friend of Jake’s as a CFO to help with financials. And of course, Ofer still offered advice where he could. 

“Some people have the attitude of, ‘No, we can’t do that because of this.’ Others say, ‘Hey, maybe we could try this.’ You need to be surrounded by the latter if you’re going to start something.”

“Some people have the attitude of, ‘No, we can’t do that because of this.’ Others say, ‘Hey, maybe we could try this.’ You need to be surrounded by the latter if you’re going to start something.” Jake says.

Learning From (Failed) Beta Products 

The Pepper beta debuted on TestFlight on May 26, 2021. The founders hoped 10,000 users would sign up. Only about 1,000 did. 

Jake and Matt blamed the low turnout on several disasters. 

The first morning, the app’s follow button stopped working. Then mid-launch, the founders had to wipe all data, accounts, and posts to fix the uploading process. Also, the Pepper trademark failed to come through after months of delay. 

Jake and Matt almost quit right then, but instead, salvaged what they could from the situation. During the beta, the cofounders noticed hundreds of users only used Pepper to post pictures of food, not recipes, making Pepper no different from any other social platform.

“During that beta, we added the requirement of uploading at least one ingredient. Our thought was, if you upload one, you’ll probably upload all of them, which turned out to be a correct thesis,” Jake says. “On top of that, we decided that if you don’t upload a recipe, that’s okay. Your friends can still see the photo and ingredients.” 

Jake and Matt updated the search function, too, so it would only show full recipes rather than a post with just an ingredient list, for example. 

“That’s how we offer helpful content to users while still satisfying those who just want to share pictures with their friends,” Jake says. 

Jake quit his full-time job two weeks after the beta launch. He’d spent the past year working the trading floor from 8 a.m. to 5 p.m. before coming home to work on Pepper. The stress compounded every month. 

“I decided to quit my job when the emotional toll became unbearable,” Jake recalls. 

To Get a “Snowball Effect,” Start Rolling the Snowball Yourself 

Jake and Matt gave themselves three months to turn their beta product into a high-ranking App Store hit. They brainstormed feature enhancements (led by Eli), worked with the developers to deploy them, and tried new marketing strategies. 

Pre-launch, the duo promoted Pepper through social media sites like TikTok and Instagram. But instead of just posting on their own pages, Matt and Jake teamed up with influencers Breanna Stark (@marriedtobbq) and Trazia Rae (@traziarae). These cooking creators spread the word about the upcoming App Store launch by using Pepper to store recipes.

They also ran several giveaways, handing out air fryers, cast iron pans, Amazon gift cards, and other kitchen appliances. Fans’ excitement during the giveaways and in the creators’ comment sections proved that users loved the concept and wanted to explore it. Matt and Jake just needed to reach that market. 

When the iOS app went live on September 4, 2021, Matt and Jake blasted it all over their social media. They reached out to connections from their alma maters as well as close friends and family to spread the word. These connections helped shoot the social food app to the top of the App Store search results whenever someone typed in “Pepper.” 

 “We realized that to get that snowball effect, you’ve got to roll your own snowball and push it yourself for a while.”

Despite a successful launch, ranking on the App Store didn’t always result in new signups. When downloads stagnated, Jake says they had to go so far as standing outside Trader Joe’s handing out recipe cards. The cards contained a QR code for the app plus recipes involving Trader Joe’s ingredients. This helped them gain a bit more traction through September. 

“For the first week it felt like we had just opened up a store and wondered, ‘Why aren’t any new customers coming in?’” Jake says. “We realized that to get that snowball effect, you’ve got to roll your own snowball and push it yourself for a while. Getting Trader Joe’s people to start downloading it helped because there are so many Facebook groups for Trader Joe’s, with hundreds of thousands of people in it, to spread the word.” 

By mid-December, the app broke 10,000 users. Then 15,000 by the end of the year. The founders counted 100,000 by March 2022 and 250,000 by Pepper’s first anniversary in September. 

Execute a Good Plan Now

If Jake and Matt had started building Pepper in 2019, when they’d first brainstormed the idea, they might’ve scaled the business faster. 

If anything, this entrepreneurial journey taught the cofounders that it’s better to execute a good plan now than a perfect plan sometime in the future (paraphrasing George S. Patton). Jake urges fellow founders to always take that step forward, to follow through on those dreams, even when they seem daunting. 

“Even if you fail, the amount that you learn from trying it goes so much further than whatever time you spent on it.”

“Ninety-nine percent of people talk about having million-dollar ideas. Everyone at some point has had one. At the same time, ninety-nine percent of people don’t even try to grasp it,” Jake says. “What I’ve realized is that even if you fail, the amount that you learn from trying it goes so much further than whatever time you spent on it.”

Three years after that late-night talk in the shed, Jake and Matt can now boast that they have a top-ranking app in the App Store. They’ve also partnered with Instacart, so customers can order ingredients and get them delivered to their homes right away. 

Most importantly, Jake and Matt have a bond as tight as brothers. One cemented by shared failures and triumphs that they’ll be sure to reminisce about in the shed for years to come. 

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Leanne Stahulak
Leanne Stahulak
Leanne’s love of books inspired her to become an author at a young age. Though she began as a creative writer, Leanne also built up her skills and experience in journalism at Miami University. After graduating with three degrees, she now tells founder stories at Bootstrappers and writes about growth and entrepreneurship for MicroAcquire.

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