Hay Bales, Head Starts, and Hard Calls

Inside the eight-year grind that turned Jasper.ai from a scrappy startup to a $1.5 billion unicorn

Written by: Taylor Cromwell

Summary

Dave Rogenmoser and Chris Hull spent eight years failing at various businesses before discovering GPT-3 in late 2020 and launching Jasper, which reached a $1.5 billion valuation in under two years.
Their breakthrough came from recognizing GPT-3's potential for marketers and validating the idea immediately, raising $44,000 in pre-sales for a non-existent product through a single webinar.
Jasper exploded from 9 to 200+ employees and crossed 100,000 paying customers within a year, with the founders maintaining their practice of personally conducting 15-minute Zoom calls with users to stay customer-obsessed.
The company faced early challenges, including a Marvel cease-and-desist over their original "Jarvis" name, which they turned into a community engagement opportunity that strengthened their brand.
In September 2023, recognizing they were "0-to-1" founders rather than scalers, Rogenmoser stepped aside for enterprise veteran Timothy Young as CEO, demonstrating rare self-awareness while maintaining their "friendship first, business second" philosophy.

Prologue

Two years ago, we sat down with Jasper’s founding team for our documentary series Spiraling Up: The Journey to Become a Unicorn. At the time, the company was fresh off a $1.5 billion valuation, riding the momentum of a breakout year, and still sporting the friendly robot logo that had become its signature. They were one of the standout stories of season three (now streaming on Hulu), and our cameras captured their rise in real time.

Fast-forward to September 2023: Jasper announced that CEO and co-founder Dave Rogenmoser would step aside for Timothy Young, a seasoned operator who had led product and engineering teams at Dropbox and VMware. The shift signaled more than a leadership change. The brand had eventually shed its playful mascot for a sleek, minimalist “J,” reoriented toward the enterprise market, and evolved its product far beyond the copy-writing tool that first captured attention.

Back when we filmed, there was only so much we could fit into a 23-minute episode. What you’ll read here is the unabridged version: the long-form origin story, as told to us directly by the founders. It’s the inside story of eight relentless years — pivots, missteps, and breakthroughs — that shaped the DNA of one of the fastest-growing companies in AI.

Origin Story

Three years before ChatGPT broke the internet, an unknown AI startup was moving like it had a cheat code. By 2023, Jasper.ai had gone from zero to a billion-dollar valuation — an improbable rise that began with two unlikely founders at a rural Arkansas wedding, surrounded by hay bales, mini corn dogs, and old friends who hadn’t spoken in years.

Chris Hull was 26, living in Atlanta, stuck in a $500-a-month internship, working through an online course on how to start a software company without money, skills, or even an idea. Dave Rogenmoser was 24, carrying around a notecard that read: “By the age of 30, be financially free by starting multiple profitable companies.” Neither knew how to make that happen.

“I didn’t know what I wanted to do,” Hull told us in an interview. “I didn’t want to be a teacher anymore. I wanted to do business, but I wasn’t sure what that looked like.” Rogenmoser was deep into The 4-Hour Workweek and Rich Dad, Poor Dad, trying to figure out how to make $5,000 a month so he could “hang out with friends and figure out next steps.”

When they ran into each other that day, neither could have pictured the path ahead: eight years of false starts, spectacular flops, and constant pivots before landing on the idea that would become a billion-dollar company. “I think what we’ve done best,” Rogenmoser says, “is pivot well and pivot quickly and pivot hard, but always carry the skills, the insights, and the relationships into the next thing.”

That “pivot-first” mindset still defines Jasper today, even as the founders have stepped aside for new leadership for a new era in AI (proving the timeless leadership skill of knowing when to hold ‘em … and when to fold ‘em).

This is the story of how a conversation around a hay bale in Arkansas turned into one of the fastest-growing AI companies in the world.

ai generated shot of Chris and Dave facing each other.

Act I: The Wilderness Years

The Partnership Formation

Hull and Rogenmoser credit much of their early business instincts to a course called The Foundation, which flipped the traditional startup playbook on its head. Instead of building a product and hoping someone would buy it, the course drilled into them the discipline of talking to customers first, finding a painful problem, and getting a commitment to pay before writing a single line of code. It was their first real lesson in grit, fast pivots, and the language of business — skills that would define everything they built afterward.

They also quickly realized they were wired differently. “It was pretty apparent even from day one,” Hull told us. “Our sweet spots are very, very different.”

“I’d been taking this course for six months,” Hull says. “Dave gets it, and within a week, he’s already trying to make sales.” Hull was the analyzer, methodically extracting ideas from physical therapists in Atlanta. Rogenmoser was the doer: get the course, pick up the phone, see what happens.

At first, they weren’t even working on the same thing. Hull and John “JP” Morgan (the third co-founder, and yes, JP Morgan is is his real name. No relation.) were grinding on one software idea. Rogenmoser had another project with a friend in Missouri. Both fizzled. And in that failure, they found their way to working together.

When they officially teamed up, Hull’s wife remembers it as a turning point. “She always points back to the email Dave sent as the moment we ‘made it,’” Hull says. “We were making zero money. I was losing money every month. But for the first time, she knew other families were involved. I wasn’t doing it alone anymore.”

The early days were anything but glamorous. Hull worked mornings at Restoration Hardware’s warehouse; Rogenmoser was in the back of a wine shop nearby. But they shared a commitment: stay in the game long enough to figure it out.

“We didn’t have a great backup plan,” Rogenmoser says. “It’s not like we could go get jobs at Google if this failed. We were going to have to make something work.”

The Spectacular Failures

Before Jasper, before YC, before any real traction, there were the flops. I’m talking full-on misfires that cost time, money, and pride.

Their very first business was a marketing agency. Their first client? A portable restroom business. “He called it ‘portable restroom,’” Rogenmoser laughs. “We called it port-a-potty. We were just begging him to sign. Three hundred bucks a month felt huge at the time.”

That deal led to an instant lesson in finesse. Their first marketing agency client was a portable restroom business—though they called it a port-a-potty company. They convinced the owner to pay $300 a month, which felt huge at the time. After the owner agreed, Dave hung up and tried to call JP to celebrate, but accidentally called the client back instead. Without realizing, he told him, “You’re our first customer,” and the client, Grant, just laughed and said, “Well, I’m excited anyway.”

Then came the Olympic gymnast who was going to make them rich selling Yerba Mate. They spent months building the most elaborate marketing funnel they’d ever made. Revenue? Zero.

Another deal seemed promising: $200 per qualified lead for a software development company. By the end of the first month, they’d made $4,000 … and spent $8,000 to get there.

“We were working 70-hour weeks to lose four grand,” Rogenmoser says. “We would’ve been better off watching TV.”

Hull sums it up bluntly: “We’ve never been married to any idea. When our customers point us in a new direction, we go. That’s what allows us to pivot so fast.”

Looking back, Rogenmoser doesn’t even call these failures. “They were crash courses,” he says. “We picked up skills, learned pricing, met people we’d need later. It was like levels of a video game.”

Those lessons — often expensive, occasionally humiliating — would later become their startup capital. “We’ll never come up with the best idea for our next company by ourselves,” Hull says. “It’s our customers.”

Building Essential Skills

What kept Hull and Rogenmoser moving forward was a steady accumulation of skills they could carry from one failed attempt to the next.

They learned to pivot without attachment. If something wasn’t working, they didn’t stick around out of pride. They took what they’d learned and moved on.

Along the way, they built community. First through the agency, then through their course business, they connected with hundreds of entrepreneurs. Many of those early customers (people they taught how to land clients or run Facebook ads) would later become Jasper’s first paying users.

Most importantly, they got comfortable with what Rogenmoser calls “intelligent failure,” failing in a way that adds to your capabilities, network, and insight. “The only reason we could launch Jasper as fast as we did,” Rogenmoser says, “is because we’d already spent eight years learning the hard way.”

It was those years — grinding in warehouses, losing money on bad deals, fixing mistakes in real time — that quietly built the foundation for their first real pivot.

Act II: Finding the Oasis

The Hot Tub Pivot

Eighteen months into running their marketing agency, Hull, Rogenmoser, and Morgan got their first big break: a speaking slot at a physical therapy conference in San Diego. They flew out with their wives, rented an Airbnb, and celebrated what felt like a turning point. “We finally had steady clients and real revenue. It felt like the momentum was finally there,” Rogenmoser recalls.

The night before the conference, they found themselves in a hotel hot tub, smoking Swisher Sweets. “We thought that’s what fancy people did,” Rogenmoser laughs. Beneath the celebration, something else was brewing.

They were great at landing clients but less inspired by delivering services, always at the mercy of other people’s products. “Are we really business owners,” Hull recalls, “or are we just managing other people’s businesses? We hated it. We joined and started the business so that we wouldn’t have a boss. And now we had like 20 bosses — all mad at us all the time.”

In that hot tub, they decided to shut down the agency and pivot to selling their own product: a course teaching entrepreneurs how to start and grow a marketing agency.

The timing was brutal. Their wives were in San Diego to celebrate finally making money. The next day, they’d be back at zero. But the conviction was stronger than the comfort of short-term revenue.

The Course Business Evolution

The course, 6K Success, was scrappy and built on hard-earned lessons. They sold it the same way they’d run their agency: fast, direct, and customer-first.

“Selling a course is really hard,” Rogenmoser says. “You’ve got to be incredible at community, incredible at paid ads, conversion optimization, funnel building, copywriting — all of it.”

They crossed $1M in revenue in the first year.

This momentum led to their first real software play: Proof, a social-proof tool that showed live visitor and purchase notifications on websites to boost conversions. Proof’s rapid early growth — from $0 to $175K in monthly recurring revenue — helped the team get into Y Combinator in 2018.

They saw YC as a chance to learn from people who had already built successful tech companies. As Hull put it, they had “this little widget tool” but lacked the know-how to scale it, and YC seemed like the best place to get that experience.

YC challenged them to think on a much larger scale. Hull recalls being asked, “What’s your big $10 billion idea?”—a question they’d never even considered while running small, scrappy projects. At the time, their mindset was simply to build something people would pay for and try to grow it.

Proof grew, but after the initial lift, revenue plateaued. Competitors caught up. The team shrank from 25 to five as they focused on profitability and watched for the next wave. Still, Proof was pivotal: it gave them SaaS experience, a network of founders and investors, and a seat close to emerging tech trends — exactly what they’d need when GPT-3 appeared on their radar.

The GPT-3 Discovery

By late 2020, with the course business steady but no longer growing and Proof stuck in neutral, Rogenmoser came across GPT-3, a new language model few outside tech circles were talking about. “I was a trained copywriter,” he says. “I knew — this looks pretty good. Like, something I would actually use.”

Through a YC connection, they got early access. Within hours, Rogenmoser turned to Hull and Morgan. “Guys, this is it. This is the business.”

The vision was immediate: package GPT-3 for marketers — Facebook ads, Google ads, headlines, email subject lines — all the copy founders and small teams struggle to produce at scale. Unlike many early testers who saw a novelty, they saw a sellable product.

“We had a whole audience from the last six or seven years that trusted us,” Rogenmoser says. “We understood marketers. We could sell this to them tomorrow.”

It was a classic Chris-and-Dave moment: spotting an emerging technology before it hit the mainstream and shaping it for a customer they already knew intimately.

Act III: The Rocket Ship

The Seven-Minute Decision

From that first message to buying the domain, just seven minutes passed. “It shows how fast we pivot,” Hull says. “How fast we’re willing to say, ‘Courses are great, but this is the next thing we’re going to try.’”

That speed wasn’t reckless. It was the product of eight years spent learning exactly what it takes to spot an opportunity, validate it, and move. They’d already built the skills, the network, and the trust to make a high-stakes call without hesitation.

And they didn’t just jump into building. They went back to their earliest playbook: prove someone will pay before writing a line of code.

Validation Before Building

They went straight to market. Rogenmoser hosted a webinar they called Proof Palooza — a nod to their earlier software company — and pitched the vision: a tool that could write high-performing marketing copy instantly.

For 45 minutes, he painted the pain: low conversion rates, the grind of writing ad after ad, the endless pressure to come up with fresh headlines. Then he offered a solution: access to their new tool for $1,000, payable today, delivery date TBD.

By the end of the webinar, 44 people had paid. Forty-four thousand dollars for a product that didn’t exist yet.

“For us,” Hull says, “it was less about the money and more about the signal. If people are willing to put down a thousand bucks sight unseen, this is worth building.”

Morgan got to work immediately on the MVP. Within weeks, they had a functioning product in customers’ hands and something even more valuable: proof that their audience wanted what they were making.

It was a return to their roots — sell first, build second — and the foundation for the kind of growth they’d never experienced before.

The Explosive Growth Phase

From the very first launch webinars, it was clear they’d struck a nerve. One brought in $100K in signups. Another hit $250K. Soon, they had $1M days.

Then came a curveball: branding. The product launched as Conversion.ai, a name that made sense for marketers but didn’t exactly scream “AI revolution.” Within months, they rebranded to Jarvis, inspired by Tony Stark’s AI assistant, a nod to speed and intelligence.

The name stuck; until Marvel’s lawyers sent a cease-and-desist: change it, or else.

Rather than panic, the team treated it like a marketing sprint. They ran contests in their Facebook group, teased options to customers, and turned the process into a community moment. In the end, they chose Jasper — a name with no existing baggage, easy recall, and, importantly, a clean trademark path.

The rebrand didn’t slow momentum. If anything, it added to the scrappy legend of Jasper’s early days: a company moving so fast that even a Marvel lawsuit couldn’t knock it off course.

Customers reacted like they’d just seen a sleight of hand. “It was a magic trick,” recalls Jasper president Shane Orlick. “People were like, Wait, how does this work? This is incredible.”

In less than a year, Jasper went from 9 employees to over 200. They crossed 100,000 paying customers. In October 2021, they closed a $125M Series A at a $1.5B valuation — officially joining the unicorn club.

“We’d spent two years trying to sell something people didn’t really want,” Rogenmoser says. “This time, they were begging for it.”

With capital in the bank and product–market fit locked, their next move was to build a moat competitors couldn’t easily cross.

The Strategic Moat Building

As the buzz around AI started to spread, so did the competition. But Jasper had a head start, and the founders knew they needed to turn it into a defensible moat.

One edge came from their early access to OpenAI’s GPT-3, something not every company could get at the time. They used it to build capabilities competitors couldn’t easily replicate. “It’d be easy to just say, ‘We can’t do it’ and take it at that,” Rogenmoser says. “Instead, we found this weird workaround.”

They also moved fast on acquisitions. Spotting promising tools on Twitter, they’d DM the founders directly — leading to deals to acquire Headline (an AI tool used for high-conversion headlines and a blog post writing assistant) and Shortly.ai (a tool to help deal with writer's block), both bringing unique features and new audiences.

Some of their most loyal early adopters came from unexpected places. Hull recalls a medical student in the UK using Jasper to save hours on coursework.

It felt more than just an AI tool. They were building a platform that was sticky, community-driven, and several steps ahead of anyone else chasing the same wave.

Customer Obsession at Scale

Even as Jasper rocketed past 100,000 paying customers, Hull and Rogenmoser kept a habit from their early days: talking to users constantly.

“During the first three months of Jasper, Dave and I were on 15-minute Zoom calls separately with customers,” Hull says. “Just asking, ‘What do you think?’”

They didn’t outsource the feedback loop. Every conversation was a chance to refine features, understand edge cases, and turn customers into advocates.

Those early calls also seeded Jasper’s community, a place where marketers, founders, and creators could share wins, troubleshoot, and learn from each other. It wasn’t just a product they were scaling; it was a network effect built on personal trust.

In a hyper-growth environment, that kind of direct connection is easy to lose. For Jasper, it became one of their most durable advantages.

Intentional Culture Choices

Scaling fast didn’t mean adopting a “move fast and break things” culture. From the start, Hull, Rogenmoser, and Morgan made deliberate choices about how and where to build Jasper.

They picked Austin over San Francisco for talent, cost of living, and quality of life. The office even had golf simulators as a reminder that work should be fun.

Most importantly, they kept their weekly “friendship meetings,” a ritual that predated Jasper.

“We want to be friends first, we want to be great husbands, we want to be great dads,” Rogenmoser explained. “And if we can take care of that, which is the core thing in our lives, then everything else is going to flow from that. How do we build a business where it serves our family, and our family doesn’t serve the business?”

That became a cultural north star, part of why they could make hard pivots and stay aligned. The tone at the top shaped the team: kindness as default, curiosity as a requirement, and the belief that relationships outlast any product.

“I tell all of our employees that for us at least, we know that 99.99% of our identity can't be in Jasper or any business we create, because in 300 years, no one's going to care about Jasper, and no one's going to care about generative AI — like it's going to be something new,” Rogenmoser says.

“We wanted to build things that have a lasting impact, and for us, that's relationships. We know that if we treat each other well, if we work on our friendship now, that could actually have an impact in 500 years, because it can change the course of someone's life.”

Act IV: The Ultimate Founder Move

Recognizing the New Challenge

By late 2022, the AI world had changed almost overnight. ChatGPT launched, and what once felt like Jasper’s unique “magic trick” was suddenly … everywhere.

The founders could see the competitive landscape shifting. The early-mover advantage was shrinking. Growth in enterprise AI was accelerating, a different game than selling to small businesses and creators.

It wasn’t that Jasper was losing; revenue was strong and the customer base loyal. But Hull, Rogenmoser, and Morgan knew scaling in this new phase would require a different skill set.

“I’ve always been a 0-to-1 serial entrepreneur,” Rogenmoser says. “I love building from the ground up. Running a 175-person growing company isn’t my greatest gift to the world.”

That self-awareness set up what might be their boldest move yet — stepping back from day-to-day leadership while the company was still in its prime.

The Self-Awareness Decision

Most founders step aside when they’re forced to — by investors, by burnout, or by a failing business. The Jasper founders did it from a position of strength.

Rogenmoser had built multiple businesses before Jasper. He knew his sweet spot was the messy, creative early stages and not the operational rigor. “The difference between building and scaling is massive,” he says. “And scaling well wasn’t where I’d add the most value.”

They started looking for someone with that skill set. The search led to Timothy Young, a veteran operator with leadership stints at Dropbox and VMware. He understood both enterprise software and the cultural values the founders wanted to protect.

Choosing Young, they said, was about creating the best odds for Jasper’s next chapter. “We wanted someone who could navigate the enterprise market without losing the founder DNA,” Hull says.

In September 2023, Timothy Young took over as CEO, and Dave Rogenmoser moved into the Chairman role. The friendship and trust at Jasper’s core made the transition possible without drama — a rare feat in tech.

Leadership changes can rattle even the healthiest companies. Jasper’s transition barely rippled.

Weekly friendship meetings never stopped. The families still saw each other regularly. Because the founders framed the move as a growth decision, not an exit, the team saw it as a sign of strength. The same pivot-first mindset that had taken them from hay bales to unicorn status was now being applied to leadership itself.

Act V: Epilogue – The Next Chapter

Today, Jasper looks different than it did when Hull, Rogenmoser, and Morgan were huddled in that Arkansas hay bale moment or smoking Swisher Sweets in a San Diego hot tub.

Under Timothy Young’s leadership, the company has shifted its focus toward the enterprise market, a space where his experience at Dropbox and VMware gives Jasper a significant edge.

The results have been clear. Enterprise ARR has tripled. Twenty percent of the Fortune 500 now use Jasper.

The strategy is deliberate, what Timothy calls a “J-curve” approach: investing heavily in capabilities that position Jasper to win the long game in AI, even as competition intensifies.

And yet, much of what made Jasper what it is remains unchanged. The cultural values that Rogenmoser, Hull, and Morgan built the company on — kindness, curiosity, and putting relationships before ego — remain embedded in Jasper’s DNA.

For the founders, this phase is proof that stepping aside from the CEO seat doesn’t mean stepping away from its impact. It’s just another pivot, one made with the same clarity they brought to every big decision in their journey.

And in some ways, Jasper’s story is still the same as it was in those early days: a group of friends chasing independence, learning as they go, and refusing to let pride keep them from making the right move for the business.

Spiraling Up: Jasper Episode (Director's Cut)

Now you can exclusively see the director's cut episode about Jasper from our "Spiraling Up" film series. Currently, season 3 of the series is only available on Hulu (watch all three episodes here. For a limited time). What viewers were not able to see in the Hulu version was the fun and funny recounting of how Dave and Chris originally named the company Jarvis, and the "communication" they received from a certain "Mouse House" regarding the use of that Marvel-related name.

About "Spiraling Up: The Journey to Become a Unicorn"

LinkedIn and HubSpot for Startups collaborated to create this inspiring documentary film series showcasing the stories of startup founders at various stages of funding and development. If you've ever dreamed of starting and growing a business, overcoming adversity, and impacting the lives of millions, this is for you.

Seasons 1 and 2 are available online at www.spiralingup.film. Season 3 is exclusively on Hulu for a limited time. "Scaling Smarter Magazine" readers can see the full Jasper episode (with the aforementioned "Jarvis deleted scene" below. Enjoy!

Author: Taylor Cromwell

Taylor is a writer, interviewer, and founder of Creator Diaries, a newsletter digging into how real people turn ideas into income. Her editorial work spans HubSpot, beehiiv, Just Go Grind, Confluence VC, and more — covering founder strategy, content marketing, and the business side of the creator economy. When she’s not writing about building businesses, she’s probably wandering an antique market, walking with a podcast, or scheming her next countryside escape.