That moment entrepreneurs realize they’ve made it

It’s easy to see when an entrepreneur hits the “turning point” in a career, however it’s hard to pinpoint exactly how it came about. Was it a happy accident? Perfect timing? A bout of good luck? Or was it a series of small, incremental milestones?

For Nimit Sabharwal, the road to entrepreneurial success was paved with questions—specifically, those of defining his customer base and customizing his product offering. Finding the answers to these types of questions led to a breakthrough moment for his mobile payments startup.

“The product we had was really a mobile platform that could be used in any industry,” Sabharwal says of Global Bay, which offered businesses cell phone-based point-of-sale capabilities, inventory management, and clientele solutions. “Between 2002 and 2008, we were anything to anyone who needed some kind of mobile solution. Because each deployment was different and each customer had very different needs, it was difficult to scale.”

Faced with a scalability problem presented by a too-diverse client base, Sabharwal, then Global Bay’s chief financial officer, changed course slightly in 2008 to focus exclusively on the retail sector. The move came shortly after Global Bay signed on with the clothing and accessories brands Coach and Guess.

“That’s when we really started to scale the business,” Sabharwal says. “It was a happy accident. We were able to get three to five retail customers pretty quickly, so we made a strategic decision to focus on retail and to try and ignore any other distractions, as hard as it was.”

By 2011, Verifone had come calling, and Sabharwal sold Global Bay to the telecommunications giant, earned out for a few years, then happily walked away.

Hitting the ‘turning point’

Sabharwal has no doubt shared his story with the fledgling entrepreneurs whose startups he advises a WeWork Labs in Chelsea.

That’s where Philip Arkcoll is building his second company, a tech-focused human resources startup called Worklytics. The idea came about as Arkcoll and his partner were growing their previous venture, Tuenti—the largest social network in Spain—and they came across the problem of evaluating a team that had grown to 100 engineers, product managers, and designers.

“The biggest challenge was how to manage a team of that size,” Arkcoll says. “It grew more and more complex with scale. How do you measure and track the productivity and performance of technology and software teams?”

As Arkcoll struggled to decide what kind of feedback to give, how to improve his team’s technical skills, determine promotions and bonuses, and track productivity, he realized there was a dearth of great HR tools specific to technology companies that could provide solutions to these problems. And so, Worklytics was born.

Eight months down the road, Arkcoll has a team of 100 engineers and has rolled Worklytics out at two companies, with a plan of increasing his client base fivefold. He points to refining his product offering to ready it for his first customers as a major landmark in Worklytics’ journey.

“With the first two customers, we worked with them very closely on getting the product to where it was ready for a larger group of customers,” Arkcoll says. “Rolling it out at the first customer was big. Having people actually using it to evaluate their engineers and getting good feedback about it—that’s the biggest milestone we have had so far.”

Still, Arkcoll is reluctant to think in terms of one major turning point to account for Worklytics’ early success. He would rather view each step of the process as a subtle yet positive change in momentum.

“There’s never one big step; it’s a series of incremental milestones,” Arkcoll says. “Having 10 other companies try Worklytics out is the next target that we set. That will be a big milestone for us. The next major milestone is to take the product commercial, and so by the middle of next year, our goal would be to grow, in terms of customers, as quickly as possible.”

Getting ‘better and better’

Arkcoll isn’t alone in his preference for viewing the minor victories of his burgeoning entrepreneurial career as part of a collective roadmap to success—as opposed to identifying one specific game changer.

“You don’t ever feel like you’ve made it,” says Jason Stein, founder and CEO of social media powerhouse Laundry Service, which was recently acquired by the sports agency giant Wasserman Media. “Up until the point where we were acquired, and even still, we have always felt like there was a lot to do. I don’t think a true entrepreneur ever thinks they’ve made it; they just focus more on what they need to build and getting better and better.”

Laundry Service, which started out as a video production company focusing on digital videos and web series, hit its stride when Stein recognized a way to combine services and fill a market gap nobody even thought existed.

“We very quickly realized, after a few videos, that making the video wasn’t enough—you had to make sure it was seen by a lot of people and have a really great distribution strategy,” Stein says. “So I said, ‘Why don’t we start a creative and distribution agency?’ And people just said, ‘You can’t do it.’ The more people who said, ‘You can’t do it,’ the more I realized this was a great opportunity.”

A ‘recipe for success’

This kind of aggregational innovation, according to another veteran entrepreneur, can be a recipe for success.

“Creating a business that, in its component parts might exist in other places, but, those components combined, has never existed before—we’re really, really proud of that and what it’s resulted in,” says Andrew Deitchman, co-founder of advertising behemoth Mother, who recently left to launch The New Stand, an underground retail venture that’s part high-end convenience store, part media company, and part technology startup.

The New Stand offers memberships through its app that allow customers to pre-fund their accounts in order to easily make purchases in its upscale underground marketplaces—currently in New York city’s Union Square subway station and Brookfield Place shopping center. The New Stand app also provides daily newsletters and playlists with carefully curated articles and music that Deitchman hopes will resonate with the company’s customer base and hopefully bring a few smiles.

And while he points to unexpectedly high retail sales and app downloads as noteworthy turning points for his nascent venture, Deitchman also subscribes to the theory of the slow and steady tackling of hurdles as the key to entrepreneurial success.

“It’s more of a culture or empire building than getting a hit,” Deitchman says. “It’s every day, checking in—how is the vibe? How are our people feeling? How do people out there feel about us? How is our work doing? Pay attention to this every single day. Incrementalize every single day.”

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