Jordan Fliegel and the advantage of having a coach

Jordan Fliegel once recruited a founding engineer with a flyer in a bathroom. CoachUp needed somebody who could build the product and work alongside its small team in Cambridge, Massachusetts. Fliegel was already working inside the Cambridge Innovation Center, surrounded by people who might fit the description. He printed tear-away notices and put them around the building. Gabe Durazo arrived carrying a strip of paper. “I have a ticket,” he said. A founding team grew by one.

It is a pleasingly modest entrance for a business that would later partner with Stephen Curry. Before the famous basketball player, there was a piece of paper and someone willing to put it where people would see it. The anecdote also offers a useful introduction to Fliegel: he looks for the person who can help, then makes an introduction possible. Sometimes the technology can wait.

The first useful introduction

His own basketball story began well short of professional promise. As a freshman, Fliegel was a backup on his high school team. Private instruction helped him become a varsity starter as a sophomore. The coach was Greg Kristof, a former college player who taught him the game in detail. Fliegel credits their work together with changing his expectations of what he could accomplish.

He went on to Bowdoin College in Maine, where he played basketball and earned a degree in philosophy and government. Professional basketball in Israel followed. His educational path also included an MBA at Tel Aviv University. The eventual entrepreneur had experienced several different kinds of instruction before he started charging customers for any of it.

Fliegel’s explanation of his progress leaves room for work. Kristof helped him break the game into smaller tasks, practice them and develop confidence through competence. Years later, Fliegel still described him as a lifelong friend. The relationship mattered alongside the technical advice. A useful coach could make an ambitious goal feel like something a player might actually attempt.

During summers home from college, and later between periods playing overseas, Fliegel began coaching young basketball players himself. The beneficiary became the instructor. He built a small local business, BostonBasketballInstruction.com, and brought in other coaches as demand increased. There was already a service people wanted; making it easier to find would become the larger business.

Footwork before fireworks

Ask Fliegel about a basketball lesson and the glamour disappears rather quickly. He emphasizes footwork, balance and removing unnecessary movement. He works through finishing moves until a player is comfortable, recaps the session, and assigns things to practice before the next meeting. It is the sort of description that would disappoint anyone hoping to buy a spectacular dunk by the hour.

“I’m patient,” he says of his coaching style. One early client arrived as a high school sophomore struggling even with layups, hoping simply to make the varsity team. Fliegel later recalled that the player had reached college basketball. That is a coach’s satisfying anecdote: an individual’s progress, with enough specificity to remember where the work began.

His favorite coach is Pete Carril, whose Princeton teams made intelligence, skill and coordinated play competitive weapons. Fliegel singles out Princeton’s victory over UCLA in the 1996 NCAA tournament. The preference fits his teaching method. A team can get more from what it already has by learning how to use it together. It is an appealing thought for an entrepreneur with a small payroll.

“The idea has to make sense, but the ideas will change.”

Jordan Fliegel

A marketplace with chalk on its shoes

Fliegel founded CoachUp in 2011; the service launched publicly in May 2012. He and co-founder Arian Radmand were connecting two groups that had trouble finding one another: athletes seeking qualified private instruction and coaches seeking students. The company began in greater Boston with more than 100 coaches, with plans to expand across the country.

He brought relevant business experience, too. At Zintro, an information-sourcing marketplace, he had led business development and learned about the mechanics of matching buyers and sellers. Basketball supplied familiarity with the customer’s problem. Marketplace work supplied another way to think about solving it. Having a good reason to start was only part of the preparation.

The early product let customers compare coaches by sport, location, price and rating, then book sessions. Payments and repeat bookings gave the platform work to do after the introduction. That detail matters. Once a coach and athlete meet, they can arrange another lesson themselves. A marketplace has to keep earning its place in the relationship.

Fliegel also supplied the first inventory in a rather literal way. He has recalled being CoachUp’s first coach and telling the parents of his basketball students to book him through the platform if they wanted to keep training with him. The founder was asking customers to use a service he was using himself. His calendar became an early test of the product.

By 2015, CoachUp was reporting 13,000 coaches and 100,000 athletes across 30 sports. Those are historical figures, a snapshot of the company during its expansion. They show the distance between a local basketball instructor’s client list and a service encompassing many kinds of athletic instruction. The original problem had traveled beyond the founder’s own sport.

Stephen Curry joins the practice

In March 2015, Fliegel announced Stephen Curry as a CoachUp partner. They had met through a mutual friend. Fliegel had followed Curry’s development from Davidson College while playing at Bowdoin, and saw the guard’s commitment to individual training as a fit for the business. The partnership joined a recognizable athlete to a service built around the hours spent practicing.

There was commercial sense in the arrangement: Curry made private coaching easier to explain to a parent who knew his name. There was also a shared belief in the value of instruction. Fliegel wrote about Curry’s continued work with coaches even after reaching the NBA. Improvement remained part of the job after the audience arrived.

The company has since continued with Fliegel as chairman. His career has accumulated recognizable partners and investors, but the CoachUp origin remains unusually concrete. A teenager got help. The teenager became a player, then an instructor. The instructor tried to make similar relationships easier to arrange. Celebrity entered a business whose purpose was already established.

A childhood friend and a different game

Fliegel’s next operating chapter involved Jeremy Levine, a childhood friend, and Draft, a mobile fantasy-sports company. He served as co-CEO. The move kept him in sports while changing the customer experience: the business concerned fans selecting players and competing through fantasy contests, rather than athletes booking instruction.

In May 2017, Paddy Power Betfair announced its acquisition of Draft. The terms were $19 million paid at completion, with up to another $29 million payable over four years depending on performance. That produced the widely repeated $48 million figure. The distinction between a payment and a possible payment belongs in the story, especially when the protagonist’s current work involves evaluating acquisitions.

The buyer said Levine and Fliegel would continue running Draft, with access to its marketing and technology resources. Selling the company therefore came with a continuing operating assignment. For Fliegel, the transaction added experience of working inside a larger organization to the experience of building and financing a startup.

Coaching the people who build companies

In 2019, he launched the Techstars Sports Accelerator in Indianapolis. The program combined early investment with mentorship and practical support. Its partners included organizations such as the Indianapolis Colts and Pacers Sports & Entertainment. Fliegel was now helping founders reach people and institutions that could be difficult to approach alone.

The sports accelerator’s 2024 class included ten startups from six countries. Its 13-week program covered customer understanding, sales strategy, hiring introductions, goals and weekly accountability. Almost 250 mentors formed part of the network. Read the assignment list and there is something familiar about it: instruction, practice, feedback and a date on which participants have to show their progress.

He also led the Techstars New York City accelerator. The winter 2023 class brought twelve companies into a three-month program with access to more than 125 mentors. Here the subjects widened beyond sport, including laundry services, project management and fragrance. Helping a founder understand a customer could be useful in quite a few markets.

Fliegel’s interest in leadership had already reached print. His 2016 book, Coaching Up!, has a foreword by Shane Battier. In his writing about criticism, he urges leaders to restore connection, offer support and then give direction. Publicly humiliating a player may protect a coach’s ego while doing very little to improve the next possession. Office managers can recognize the same temptation.

Buying a business, finding a team

Acquisition entrepreneurship brought Fliegel a new set of problems. He and Tim Ericson each bought a small profitable business and found the process difficult. Searching, financing and completing a purchase required one set of skills; operating afterward demanded another. Familiarity with venture-backed technology companies did not automatically supply the support system they wanted as small-business owners.

Ericson had joined Acquisition Lab as a member in 2022. He and Fliegel began backing qualified buyers who needed equity alongside their acquisition financing. That effort became Shareholder Ventures. Ericson’s operating experience also helped produce SMB Edge, which offered financial and hiring support. Each business addressed a different part of the ownership process.

In late 2025, Acquisition Lab and Shareholder Ventures merged, with SMB Edge incorporated into the services offering. Fliegel became CEO of the combined Lab. Ericson serves as chief operating officer, Chelsea Wood as chief community officer, and Walker Deibel as board member and venture partner. The organization brings education, community, capital and operating services together.

In July 2026, Fliegel described his ambition as helping the acquisition entrepreneur throughout that journey. His concise instruction for building a business was: “Your hero needs to be your customer.” It brings the attention back to the person attempting something difficult. The platform, the investor and the CEO have supporting parts to play.

That is a useful place to leave him. His career has moved from a basketball court to marketplaces, fantasy sports, accelerators and business acquisitions. The recurring interest is a person trying to improve, surrounded by people who might help. Greg Kristof supplied that relationship early. Fliegel has spent much of his working life finding ways to make the next introduction.