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Brian Distelburger - From Farmlands to IPO

By: Rahul Rana ・ 9 min read

Call Your Shot

The arc of Brian Distelburger’s story is underscored by an unwavering commitment to doing whatever he wanted to do, on his terms and timeline. It starts with his grandfather, who got his start in entrepreneurship after fleeing Nazi Germany around the start of World War II and settling in Rockland County to start a dairy farm. 


Rockland is just far enough north of NYC that the skyline disappeared, but close enough to feel its gravitational pull. A quiet, working-class, commuter-heavy patch of suburbia, more edge-of-the-city rural than upstate pastoral. 


In a town called New City, Brian Distelburger grew up on a dairy farm doing “real, hard work” with his distinct NYC bravado: gritty with stubborn, relentless clarity.  Amongst his cows and amidst the heyday of the Internet boom, his formative years were defined by a deep, profound urge to build anything that would make money, especially if its on the cutting edge of technology. 


While tending to a farm doesn't directly prepare for building a software business, Brian developed a tolerance for quiet, rhythmic, unforgiving work on this farm. It’s the type of work where brutal consistency and obsessive attention to detail are required, and results compound over time. 

In the throes of the laborious work, he craved to do something to meet the scale of his ambition. So, in a very Babe Ruth-like manner, he called his shot. At 16, he pointed his bat, vowing to one day build a technology company in New York City. 


That was his life’s purpose: 1) build a technology company, 2) in NYC. 


He later admitted it sounded “bizarre” at the time. Strange, even. While the tech world was racing west, toward scrappy Palo Alto garages and flashy VC dinners in Menlo Park, Brian was pulled in the opposite direction toward the pulse of something more home to him. 

“I always knew I wanted to build in New York,” he defiantly said, contrarian for his time. 

Growing Up

A self-proclaimed “oddball,” Brian had a penchant for tinkering with anything that could make him money. His personal ambitions began with a landscaping business, then evolved into buying and selling motorcycles near Cornell’s campus. He founded a motorcycle shop with a few of his buddies, called Ithaca Motorcycle Works, where he received a crash course on everything from starting a real business to co-founder dynamics to customer success. 


That later led to building an online storefront for a Ducati dealership, sparking a rebellious urge to leave everything and do a cannonball run on his motorcycle toward the Darien Gap on the border Panama and Colombia, without telling his parents. Dreaming about driving through 80 miles of dense jungle, Brian let it rip. He bought an almost-wrecked BMW motorcycle and rode it around the country for three months. The further he went, the more he yearned for the journey, crossing into Mexico in September 2001. 


Like many New York and New Jersey kids, his plans had to pivot after 9/11. New York was calling his name once again, spurring Brian to rush back as fast as he could to get back home. Upon some deep reflection, his commitment to building a tech company in the City compelled him to join Traffix, a small publicly traded advertising and digital marketing company. 

In his words, the kindest thing anyone has done for Brian was to tolerate him, specifically his parents, during his childhood. 


His parents embodied the notion of ruling with an iron stomach vs. iron fist — they were willing to give freedom to explore and make mistakes, no matter the circumstances. 

“[Despite] terrible attendance in school, [riding] a motorcycle around the country for three months without telling them, and a bunch of other stuff, I think it was an incredibly kind thing that they were able to tolerate a lot of that [and] give me the freedom to explore and make mistakes and figure a bunch of things out for myself, which I think is one of the better gifts a parent can give a child.”

Growing Up

A self-proclaimed “oddball,” Brian had a penchant for tinkering with anything that could make him money. His personal ambitions began with a landscaping business, then evolved into buying and selling motorcycles near Cornell’s campus. He founded a motorcycle shop with a few of his buddies, called Ithaca Motorcycle Works, where he received a crash course on everything from starting a real business to co-founder dynamics to customer success. 


That later led to building an online storefront for a Ducati dealership, sparking a rebellious urge to leave everything and do a cannonball run on his motorcycle toward the Darien Gap on the border Panama and Colombia, without telling his parents. Dreaming about driving through 80 miles of dense jungle, Brian let it rip. He bought an almost-wrecked BMW motorcycle and rode it around the country for three months. The further he went, the more he yearned for the journey, crossing into Mexico in September 2001. 


Like many New York and New Jersey kids, his plans had to pivot after 9/11. New York was calling his name once again, spurring Brian to rush back as fast as he could to get back home. Upon some deep reflection, his commitment to building a tech company in the City compelled him to join Traffix, a small publicly traded advertising and digital marketing company. 

In his words, the kindest thing anyone has done for Brian was to tolerate him, specifically his parents, during his childhood. 


His parents embodied the notion of ruling with an iron stomach vs. iron fist — they were willing to give freedom to explore and make mistakes, no matter the circumstances. 

“[Despite] terrible attendance in school, [riding] a motorcycle around the country for three months without telling them, and a bunch of other stuff, I think it was an incredibly kind thing that they were able to tolerate a lot of that [and] give me the freedom to explore and make mistakes and figure a bunch of things out for myself, which I think is one of the better gifts a parent can give a child.”

Brian’s Way

Long before he built a company, wrote a line of code, or even made it to NYC, Brian spent his freshman year of college in Israel through a study abroad program, somehow graduating despite being deemed, quite literally, the student with the lowest attendance rate in the school’s history. 


“I had the lowest attendance rate in the history of the school. Kids with better attendance rates than mine got thrown out, Distelburger ironically recalls. “I was excited about [studying in Israel] because I thought it was an opportunity to really travel around the country and really learn that way, [not] sitting in Econ 101.” 

How is that even possible? Well, he simply approached the guy running this study abroad program and declared his intentions painfully direct: 


“I was like, ‘Look, I want to travel and enjoy the country and experience it, not like sit in class. I’m not going to go to class. I’ll show up and take the test. I’ll pass everything. But I’m not going to be sitting in class. If that’s not going to work for you, I can leave now.’”

Brian was not bluffing, but he also never misled his teachers. He set expectations right from the start. His offer was accepted, and the rest is history. 


During his undergraduate years at Cornell, the theme continued. Brian grew tired of the seemingly useless curricula he was forced to engage with. He yearned to capture even just a sliver of the internet and the collective energy around it, to be on the edge of what’s technologically possible. 

“Nothing that was being taught in school had anything really to do with the internet,” he recalled. “It was this emerging thing, and it was overwhelmingly obvious to me that that’s what I wanted to be doing.” 

So, he said ‘screw it.’ Brian discovered that no one checked IDs in the MBA building and took advantage of that opportunity to sneak into graduate management classes, where entrepreneurs like Bill Trenchard, now of First Round Capital, gave guest lectures about building internet companies from scratch and selling startups to companies like Microsoft and others. 

“That was the only place where anything remotely interesting was happening,” he joked. Brian went so far as to declare a General Studies major, a loophole that allowed him to skip required courses and build his own learning plan. Unorthodox, yes, but entirely intentional to chart his own path. 


In a very Sinatra fashion, he did it all his way. Brian’s Way.

The GymTicket Era

As an early 20s new grad, Brian made it to NYC to fulfill his childhood dreams, leading a company called Traffix. 

The NYC startup arena was a barren landscape, but its early inklings were present. Etsy was getting off the ground, Tumblr was going viral, and Kevin Ryan of Alleycorp was ripping companies left and right with Business Insider, MongoDB, and Gilt Groupe. 


Working his way up from low-level operations to running the database marketing team at Traffix, Brian found himself leading a team of 30+ as a 23-year-old and commanding about 80% of the company’s revenue. With a golden opportunity to run a department as a young person, Brian parlayed his seniority to work closely with the company’s leadership, leading him to meet two of his future co-founders, Jay Greenwald and Howard Lerman. 

With Jay, Brian started his first large-scale company, specifically a privacy protection software startup, where he would buy security software licenses such as Norton Antivirus and Webroot at wholesale prices, bundle them, and sell them to consumers on a monthly subscription basis. He scaled this business to $20M of revenue in three years. 

With Howard, he founded GymTicket, a company selling customer leads to gyms. They functioned as an aggregator of consumers seeking gym memberships, while also serving as an online media buyer for the industry. 


Brian did everything right. He knew how to buy the media, drive the traffic, get them to convert, and bring gyms online. He had real momentum until it all blew up due to one unforeseen, overlooked potential disaster. 


Most gyms did not have wifi. 


Naturally, consumers would sign up on GymTicket, and immediately go to the gym wanting to get their first workout in, while the gym front desk had no clue who they were. Much to Brian’s chagrin, being a founder operating on the edge of technology, GymTicket had to humbly revert to using fax machines. 


The fax machine breakthrough brought them to over 4,000 gyms, driving traffic to them on a performance basis at a third of the industry average. The team copied that playbook across veterinarians and chiropractors, and auto repair shops, building a sophisticated model to figure out the best verticals to go after. 


25 verticals later, they felt ready to brand the overall company. Yext was born (from a random name generator for 4 letter domains), and started with a bang.

Farmlands to IPO

From humble beginnings in a rented, one-room basement office in Columbus Circle rose a company that would raise over $120 million before its IPO and become one of the earliest glimmers of New York’s 2010s tech renaissance. Brian did it for himself, and his city. 


One fateful day after a capital raise led by Sutter Hill, Distelburger brought his company to their third office, finally having the space to work alongside his 25 employees at the time. Yext was barreling through new offices, their third in two years. They were outgrowing their spaces at a invigorating rate. This new one brought a buffer for the team to expand without stepping on each others’ toes. 

Their energy was high. The team felt great. They individually lugged their monitors and chairs from their last office as a moving company was too expensive for the scrappy startup. After their collective workout, they celebrated with a quick team lunch, squeezing into a small glass-walled conference room and eating takeout out of paper bags. Someone cracked a joke about an odd smell permeating the new office, and that’s when the light changed.

A yellowish hue suddenly filled the room. Out of the back window, the team saw flames and smoke bellowing up from the restaurant beneath them. In an instant, the Yext crew rushed out of the office as the fire department arrived. 


“It’s always a good reminder,” Brian half jokingly said, “that just when you think everything’s all set, you may have flames shooting up in the floor underneath you.”

They survived. And they thrived. Conversations eventually turned from stretching runway to discussing when to go public. An IPO was an inevitability for Yext, about 10 years after its founding. They had amazing customers, a fantastic product, and were notoriously capital efficient. Upon crossing $100M ARR, the management team started to think about what the future held. Going public was just a step on the journey. 

In early 2017, the moment finally came. Brian made it. More than a decade of calling his shot led him to this moment: IPOing his New York-based technology company. 


“I remember having to get dressed nicely because you're going to like the stock exchange… there's like a big banner on the side of the New York Stock Exchange with your company's name and logo, and they do a great job with all of [the] pomp and circumstance… it was just honestly the coolest thing [to ring] the bell.”

Opening day had Brian feeling like he was “sort of floating through this whole crazy day” with his team. Trading began, confetti flew. The draped YEXT banner looked surreal: showing a scrappy SaaS company logo against the backdrop of a century-old institution. Surrounded by his long time friends and employees that surpassed the capacity allowed by the NYSE, Brian took in the moment second by second. 

Back in the office by 11am that morning, he soaked it all in, reflected, and pinged his entire team to call up a bunch of their earliest customers to thank them for their resounding support. And then he partied. But, first came the customers. 


“I told everyone that day to just call a bunch of our customers who were very early on the journey, just to thank them. I thought that was an important way to spend the day.” 

Spirits high, Brian went headfirst into the first few years as a publicly traded company, seeing very high highs around 2018 and an unfortunate struggle during COVID. With a business entirely predicated on people visiting physical locations, Yext was heavily vulnerable to lockdowns. 


COVID disruptions forced Yext to make a decision in light of customers cutting contracts and lost revenue. Brian chose the way of protecting his “extraordinary” employees. 

“We made a choice at the early onset of COVID… we saw the business was heavily impacted… and we basically made the choice that we wanted to try to… we had an extraordinary team and we wanted to try to keep the team intact... Even though basically customers were cancelling and we couldn't really sell our product at the time… we tried to pivot our product strategy and our go-to-market… Long story short, that did not work… In hindsight, we couldn't bring ourselves to like lay off a ton of the company at the early onset of a global pandemic, and in hindsight that probably would have been the right thing to do.” 

Brian admitted to making a core lapse in judgment during this time. He did not adapt quickly enough. After stabilizing the company upon lockdowns being lifted, there was massive leadership churn, which led to Brian moving out of an operating role and to a Board role, and then stepping down within a few months. 

He did the job, and rode off into the sunset.

Farmlands to IPO

From humble beginnings in a rented, one-room basement office in Columbus Circle rose a company that would raise over $120 million before its IPO and become one of the earliest glimmers of New York’s 2010s tech renaissance. Brian did it for himself, and his city. 


One fateful day after a capital raise led by Sutter Hill, Distelburger brought his company to their third office, finally having the space to work alongside his 25 employees at the time. Yext was barreling through new offices, their third in two years. They were outgrowing their spaces at a invigorating rate. This new one brought a buffer for the team to expand without stepping on each others’ toes. 

Their energy was high. The team felt great. They individually lugged their monitors and chairs from their last office as a moving company was too expensive for the scrappy startup. After their collective workout, they celebrated with a quick team lunch, squeezing into a small glass-walled conference room and eating takeout out of paper bags. Someone cracked a joke about an odd smell permeating the new office, and that’s when the light changed.

A yellowish hue suddenly filled the room. Out of the back window, the team saw flames and smoke bellowing up from the restaurant beneath them. In an instant, the Yext crew rushed out of the office as the fire department arrived. 


“It’s always a good reminder,” Brian half jokingly said, “that just when you think everything’s all set, you may have flames shooting up in the floor underneath you.”

They survived. And they thrived. Conversations eventually turned from stretching runway to discussing when to go public. An IPO was an inevitability for Yext, about 10 years after its founding. They had amazing customers, a fantastic product, and were notoriously capital efficient. Upon crossing $100M ARR, the management team started to think about what the future held. Going public was just a step on the journey. 

In early 2017, the moment finally came. Brian made it. More than a decade of calling his shot led him to this moment: IPOing his New York-based technology company. 


“I remember having to get dressed nicely because you're going to like the stock exchange… there's like a big banner on the side of the New York Stock Exchange with your company's name and logo, and they do a great job with all of [the] pomp and circumstance… it was just honestly the coolest thing [to ring] the bell.”

Opening day had Brian feeling like he was “sort of floating through this whole crazy day” with his team. Trading began, confetti flew. The draped YEXT banner looked surreal: showing a scrappy SaaS company logo against the backdrop of a century-old institution. Surrounded by his long time friends and employees that surpassed the capacity allowed by the NYSE, Brian took in the moment second by second. 

Back in the office by 11am that morning, he soaked it all in, reflected, and pinged his entire team to call up a bunch of their earliest customers to thank them for their resounding support. And then he partied. But, first came the customers. 


“I told everyone that day to just call a bunch of our customers who were very early on the journey, just to thank them. I thought that was an important way to spend the day.” 

Spirits high, Brian went headfirst into the first few years as a publicly traded company, seeing very high highs around 2018 and an unfortunate struggle during COVID. With a business entirely predicated on people visiting physical locations, Yext was heavily vulnerable to lockdowns. 


COVID disruptions forced Yext to make a decision in light of customers cutting contracts and lost revenue. Brian chose the way of protecting his “extraordinary” employees. 

“We made a choice at the early onset of COVID… we saw the business was heavily impacted… and we basically made the choice that we wanted to try to… we had an extraordinary team and we wanted to try to keep the team intact... Even though basically customers were cancelling and we couldn't really sell our product at the time… we tried to pivot our product strategy and our go-to-market… Long story short, that did not work… In hindsight, we couldn't bring ourselves to like lay off a ton of the company at the early onset of a global pandemic, and in hindsight that probably would have been the right thing to do.” 

Brian admitted to making a core lapse in judgment during this time. He did not adapt quickly enough. After stabilizing the company upon lockdowns being lifted, there was massive leadership churn, which led to Brian moving out of an operating role and to a Board role, and then stepping down within a few months. 

He did the job, and rode off into the sunset.

Broken Promises

After leaving Yext, Brian made a quiet promise to his family: no more companies. At least not for a while. 

“In that few month period [after Yext], I promised my wife and everyone I know, [that] no matter what, I just won't start another company. [It is] definitely off the table,” Brian chuckled with a smirk on his face. 

“Everyone who knows me well was like ‘okay, whatever. I don't believe you.” 


His childhood goal of building a tech company in NYC did not just stop after Yext. 


Seeing first hand that NYC was still second to Silicon Valley as a startup hub, Brian once again said ‘screw it’. He brought the ecosystem to him, starting and joining the Board of Tech:NYC, a nonprofit advocating for the tech community in the Greatest City in the World. Brian’s knack for programming his reality and morphing his surroundings into his way struck again in a big way. 

 

But he couldn’t sit around idly without a company to build. An intense urge to get back to operating left Brian focusing his attention and energy on what would become Windmill. 


The idea came from his Yext days, when he felt the strain of poor HR software that attempted to manage tens of thousands of people. He led thousands of people, yet had no effective tools to scale his people management. Most HR software, in his mind, are “giant flaming piles of garbage,” because it is built for HR teams, not for people. Obsessed with optimizing for talent density, Brian explains: 


“How do we make sure we’ve got the right people on the team, in the right roles, working on the right stuff through all our stages of growth? I tried everything in the book, and all I could see was how we were falling short. The answer is, unfortunately, pretty simple. People are terrible managers.” 

So he built what he wished he had: an AI-powered assistant for managers. Windmill creates systems for people management, such as weekly accomplishments, employee profiles, real-time feedback, and more. 


“You end up with a team that's really focusing their energy and attention in the right way, you're reducing cycle times, and employees can have a better experience because they're actually doing meaningful work, [getting] help, feedback, and coaching.” 

Rethinking decades-old management philosophies and systems is no joke. Easily almost every company in our economy worked that way, built upon trial, error, and mundane business textbooks. 

But, one thing you can always bet on is that Brian will figure it out, Brian’s Way. 

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