June 21st, 2016 | By: Katie Parrott
When Jason Ross packed his bags to make the big move to New York City in 2013, it wasn’t for a girlfriend, or to chase his dreams of stardom to the Big Apple. It was for a company – his company, the one he’d started building more than seven years before.
He’d sold that company, the early apparel eCommerce success story JackThreads, to an upcoming media company called Thrillist about three years earlier. The company was thriving in its new environment in New York. But back home in Columbus, Ohio, Jason started to feel like he was on the outside looking in.
“I started to realize all these meetings were happening in New York,” Jason remembers. “So you start to feel like, ‘Oh man, things are happening at my company that I didn’t put in place. I’m going to move up there, so I can be a part of it, take the reigns back.’”
By the time he got there, he says, he realized that “the ship had kind of sailed.”
“I was up there and in all these meetings, but by that point the decisions had been made, the direction of the business was set, and even though I was not in favor of all of those decisions, there was nothing I could do.”
At that point, Jason made one of the most gut-wrenching decisions a Founder ever has to make.
He decided to let JackThreads go.
If you’d told Jason seven years earlier that in less than a decade JackThreads would be acquired and he’d be jetting off to New York to be a part of it, he might have had a hard time believing you.
Back then, he was in full hustle mode in Columbus – “just trying to pull it all together, not go broke, and not quit.”
Pulling it all together was not an easy process – or a fast one. From the time he wrote the initial business plan in January 2006 to when the site launched, it took two and a half years – every day of it self-funded, with the exception of one SBA loan in early 2008.
To make ends meet, Jason made full use of what today we would call the “gig economy.” He leaned on mentors for odd jobs, took on consulting gigs, worked for his uncle’s hotel remodeling company on the weekends, and tended bar at night – all so he could keep his days free for working on the idea that was becoming JackThreads.
To build the site, he tapped into the freelance community in Columbus, plus some students at Ohio State who worked on the site as part of a class project.
“It was kind of a slog, but we got the site built,” he remembers.
Finally, in July of 2008, JackThreads launched. Watching the revenue numbers tick steadily upward in the first few months – $500 one month, $1,000 the next, $10,000 the month after that – that’s when Jason knew that those two and a half years had been worth it.
“We launched in July and by December I knew, ‘Damn, we’ve really got something here.’”
Once JackThreads was live, the name of the game became keeping up with that insane growth.
By the end of year two, the team had grown from Jason and one developer, who came aboard in the summer right before launch, to a full team of about a dozen employees. “We were here in Columbus, we had a nice business – low seven figures in revenue,” Jason remembers. “We were running on this duct-taped-together system, with a great team with a lot of energy and enthusiasm. Not a lot of experience, but we were getting it done. It was fun.”
But as the team and the business kept growing, so did the pressure on Jason as the solo Founder and CEO.
You find yourself thinking pretty much constantly, ‘You’ve got something, don’t screw it up.’ And the thing is, you don’t have anyone to talk to about how not to screw it up.
“We had gotten to this point where we were growing – a few months in, we were already profitable,” Jason remembers. “And that was great, but at the same time that’s when it hit me – it’s just me. I don’t have a co-Founder, I have everything on the line, and on top of that I’ve got ten to twelve people who are all depending on me for their jobs. And I didn’t have anybody to talk to about these bigger business problems – financial challenges we were facing, technology challenges we were facing.”
And that kind of isolation, Jason says, is pretty much guaranteed to get to you after a while. “You find yourself thinking pretty much constantly, ‘You’ve got something, don’t screw it up.’ And the thing is, you don’t have anyone to talk to about how not to screw it up.”
Adding to that pressure, Jason says, was an increasing sense that if JackThreads was going to grow into the brand he knew it could be, he needed to take action.
“Right around that time, the space we were in started to become a big thing. Companies that we were competing against had raised tens of millions of dollars. And people knew about us, but we were in Columbus, hadn’t raised any money, and it’s this small team. So I started having this feeling of vulnerability. I started to feel like, ‘Man I need to protect this business. We’ve got something, I need to protect what we’ve built.’”
Then, almost as if some startup fairy godmother had been listening to Jason’s thoughts, the companies that had been circling some of his competitors found the promising little flash sale company out of Columbus, Ohio.
Suddenly Jason found himself fielding offers from multiple companies – three of them great opportunities from a financial standpoint. “One of the three, the culture was not a fit for me,” Jason remembers. “One of the three, it was financially better, but it was an older retail company, so I felt like it wasn’t going to be a fit for an upcoming digital company.”
The third one was Thrillist. Pretty early on, Jason says, he knew it was the clear winner – and not just financially. “I was thinking, ‘Alright, we’re in Columbus Ohio with not a lot of money and an inexperienced team – with Thrillist, not only can we get money and help, but we can also tap into two and a half million guys that are our target audience.’”
That audience, Jason said, was the factor that clinched the decision to move forward with Thrillist. “That was the reason I liked them the most, why I did the deal – because it wasn’t just money, it was strategic. It seemed like what was best for my company at the time.”
But not long after the papers were signed and JackThreads had officially been brought under the Thrillist umbrella, Jason realized that the reality of sharing custody of his brainchild with its new adoptive parent was going to be more complicated than he originally bargained for.
“I realized pretty early on that it was a mistake.”
The story of the startup world is a story of big bets. Some of those bets pay off, some don’t, and some of the most interesting moments inside a company are what happens when one of those bets doesn’t turn out the way you expected – and what happens next.
The JackThreads deal was part of a big bet that Thrillist was making on a new business strategy called “content and commerce.” The idea was that if you married a media company and an eCommerce platform, the business that resulted would be bigger than the sum of its parts.
“But once we did the deal and we started doing that, it was pretty clear early on that it was not going to work,” Jason remembers. “A media business exists for a reason: people come to read content, and they trust your voice. And when you start trying to sell shit to them, it just gets blurry.”
Meanwhile, putting that content-commerce strategy in place came with some pretty relentless growth milestones for JackThreads.
“We set these growth goals – and we set them together – because we wanted to shoot for the stars,” Jason says. “But once we had these numbers in place that were so unrealistic, it was all about just grow or die. We had KPIs and we have these budgets and spreadsheets, and it was grow or die at all costs.”
You can be realistic and reasonable as a business, but everything that’s being done has to be in line with, ‘How do we make this the best experience for our guy?’
Before long, Jason started to realize that those growth expectations they’d set for JackThreads had started to get in the way of what he wanted the company to become. “I wanted to build JackThreads into a great brand,” Jason says. “Because it was already growing, on its own, and I thought, ‘If we just invested in this separately, think about it as its own businesses, it will be awesome.’”
For Jason, investing in the business meant making tons of improvements to the brand, touching everything from product to process to user experience. “It’s about doing what is right for the customer,” Jason explains. “What is right for the customer? It’s great product that’s presented with really great creative. It’s making sure the policies are super in favor of the customer. You can be realistic and reasonable as a business, but everything that’s being done has to be in line with, ‘How do we make this the best experience for our guy?’”
But with the budgets they had put in place and the growth goals that JackThreads was responsible for, Jason says, those brand improvements quickly took a backseat. “Any time we missed a number for the month, everything we were working on brand-wise went out the window,” he remembers.
Jason says that experience – of setting razor-thin budgets that push your company and its people to their limits – has taught him something important about how to manage growth. “You have to take the long view,” Jason says. “You have to be able to step back and ask yourself whether all this unnecessary pressure you’re putting on your business is going to be worth it.”
At time time, as he watched the pressure beginning to mount and the creative direction of the company drift farther and farther from what he’d envisioned, Jason’s personal relationship to the company he had built started to change.
“It got to a point where I started thinking, ‘Wow, I can’t do the things I want to do, I can’t build this into the brand that I want to build.’ You lose a little control over what you built. Some people are okay with that. I personally was not.”
And like that, Jason started to realize that the passion and fire that had gotten him up every morning excited to go in and get to work – that passion was gone.
“It just became a job,” he says.
As frustrating as his creative and strategic differences with Thrillist became, Jason is quick to highlight some of the positives that came from his four years with the company.
One huge improvement: he finally found what he’d been missing as a solo Founder in Columbus. “In the first year after that deal, I found the right counterpart for me – I found the right person who could sit next to me and we could have these real conversations,” Jason remembers. “So that was a big help, because now I had someone to be strategic with.”
Gaining access to Thrillist’s pool of investors also gave Jason a lot of valuable insight into some of the strategic aspects of building a business. “I learned a lot of great things from them about how to structure a company,” he says. “The KPIs and the transparency we had into everything we were doing was awesome. That’s how you run a business. I’ll never run a business differently.”
And then there were those growth expectations, which Jason says forced him to start thinking more in-depth about the kind of company that he wants to build moving forward. “How will I manage my culture, and what will I do when we set up a budget that we think we can hit, but we’re not hitting it?” he says. “What kind of pressure am I going to put on the business, or what kind of pressure am I not going to put on it?”
I did what I set out to do. I wanted to protect the company, and that’s what I did – I protected it.
Looking at where JackThreads is today, Jason says he’s happy about the direction the company has taken since he left. In September 2015, the announcement came that JackThreads and Thrillist were being split back into separate entities – an evolution which Jason says is “great, because it puts more emphasis on brand, experience, and putting the customer first, which is what’s right for JT.”
On a business level, Jason says, he’s at peace with the decisions he made for JackThreads. “I did the right deal,” he says. “I did what I set out to do. I wanted to protect the company, and that’s what I did – I protected it.”
But while Jason is satisfied with the deal from a business perspective, on a personal level, he says, it’s a different story.
“That’s what I mean when I say it was a mistake — for me personally, it was a mistake to give up control the way I did,” he explains. “It took away everything I loved about JT.”
Hindsight is 20-20, and we can only ever make decisions with the information we have available to us at the time. Still, I ask Jason what he would say to himself if he could travel back to the time of the acquisition, knowing everything he knows now.
“I would say, trust your instincts, because you’ve got something special,” Jason says. “You’ve got a good gut, you’re making good decisions, you’ve got good people around it. Just trust what you’re doing and keep going. You can make sure the business is protected, but you don’t have to give up control to do it.”
Today, Jason is back in Columbus, but if you think he’s sitting back and twiddling his thumbs, think again.
After his official departure from JackThreads in Winter 2014, he took some time to process and decompress. “I went out to California for three months, got a beach house, got healthy, ate good food, slept well – all the things I wanted to do, I did.”
As great as that relaxation was, he says, it wasn’t long before the impulse to be doing and building started to rear its head.
“I’d say after about six months of being off, I was like, ‘Alright, I’m ready to do it again.’ You get a little bored and you’re like, ‘Okay, what’s next?’ ”
As for what is next, Jason says he’s taking his time. “Sometimes you just want to rush into it, because you’re like, ‘Man, I had this great thing,’ and you want to recreate that after it’s over. But it took eight years to build that. So to recreate it, realistically, that’s another eight years.”
I think if I find the marriage of passion and solving a problem, and I have great people around it, something’s going to happen.
More than anything, Jason says, he’s honing in on the key elements of what made him fall in love with JackThreads in the first place.
“JackThreads worked because it was a combination of passion, great people, and solving a problem,” he says. “So I’ve looked for that again. I don’t necessarily know that I’ve found the perfect fit yet, but I’ve found some great things to get started with, and I think if I find the marriage of passion and solving a problem and I have great people around it, something’s going to happen.”
As for whether he feels any pressure to match the success of his first company with his next project? “There are days I’ve thought about it, that for people to think you’ve had another success, you have to match the success you had before,” he says. But at the end of the day, Jason says, that external perception of success is just not what it’s about for him.
That wasn’t always the case, he admits. “When I was younger, with JackThreads, it was like, ‘It’s gotta be a hundred million or bigger – that’s success,’” he says.
Now, though? “Honestly, if I found some great business that I cared about, that solved a real problem, and had great people around it, and you never heard from me again, I’d be happy as hell.”
Every entrepreneurs struggles. Yes, even Elon Musk. Heading both Tesla and SpaceX was never the original plan, and unsustainable at that. But, by building a stronger team and selectively adding talent and expertise through levels at both companies, Musk was able to maximize his productivity and have some semblance of work/life balance.