Happy National Entrepreneurs’ Day! 

The United States is renowned as the most entrepreneurial country in the world, but it wasn’t until 2010 that there was a day set aside to celebrate the achievements of its dreamers and innovators. 

National Entrepreneurship Week was first observed November 14-20, 2010, with November 19 earmarked as National Entrepreneurs’ Day. The holiday is the handiwork of David Hauser and Siamak Taghaddos, two entrepreneurs who lobbied for a nationally recognized celebration of the trailblazing men and women who built something from nothing, created jobs, and made America what it is today. 

As the years have passed, the celebration has evolved and grown. On October 31, 2023, the President declared November 2023 as National Entrepreneurship Month and November 21, 2023 as National Entrepreneurs' Day.

WithMe is proud to celebrate this holiday, and it only seems fitting that we mark the occasion by highlighting the achievements of our visionary CEO, Jonathan Treble, and the entrepreneurial endeavor that brought WithMe to life.

Seizing an Opportunity

It was a blustery day in Chicago, with 10 inches of snow covering the ground, when Jonathan Treble needed to print concert tickets. To add insult to injury, it was the weekend. It took two hours, thirty dollars and one soul-crushing visit to Kinko's to get the job done. 

The year was 2014. PrintWithMe didn’t exist, and mobile ticketing was far from the norm. Concertgoers everywhere were dealing with the same dilemma every day. Where other fans saw major inconvenience, Treble saw incredible opportunity. He set out on a one-man mission to make printing convenient for everyone, everywhere. 

“After experiencing the printing problem a couple of times, I had a ‘lightbulb moment’ and realized that a network of pay-per-use printer stations would not only be feasible from a technology perspective, but also viable from a business perspective,” says Treble. 

So, later that year, in July 2014, Treble bought a printer at Staples and coded a checkout system with the help of some friends. The rest, as they say, is history. What resulted was PrintWithMe, a self-serve, wireless printer station that allows users to print documents via email from any digital device. 

Building a Customer Base 

Two short weeks after crafting the PrintWithMe prototype, Treble found his inaugural champion in Eva’s Café, a cozy eatery situated near his apartment in Chicago’s Old Town neighborhood. Opting for a highly personal sales strategy, he boldly approached a shift leader (who also happened to be Eva’s nephew) about the possibility of placing a PrintWithMe kiosk in the café. Much to Treble’s surprise, his proposition was met with few objections, and the restaurant almost immediately agreed to partner with him. Their PrintWithMe device went live on August 1, complete with a ribbon-cutting ceremony officiated by Eva. 

That initial interaction left Treble optimistic he could earn the trust of other Chicago café owners using the same direct and highly personal approach. 

Inevitably, the enthusiasm of local business owners proved to be overwhelming. However, as with much new-to-market technology, consumer early adoption of the self-service, wireless printer stations was limited. 

“I had to make some inferences that there was enough demand for the business model to work at scale,” explains Treble. “It wasn’t until about two years in that I saw a more robust level of demand and revenue from our first batch of apartment building customers.” 


As Treble began to work more closely with multifamily properties, he noticed a trend in property managers referencing printer amenity misuse and uncontrollable consumption. To address the issue, PrintWithMe developed proprietary Print Allowance technology that gives property managers the ability to set a limit on the number of free pages per resident, actively track usage and automatically charge residents when their allocations are exceeded.

In the words of Treble, the development and implementation of this technology was “one critical feature change that helped us not only survive, but thrive, as a company.” 

Developing a robust client base in the multifamily space also brought about innovative additions to the PrintWithMe product mix. At the recommendation of Bob Flannery, one of PrintWithMe’s multifamily property executives, Treble began to explore the possibility of expanding the company’s services. 

“Bob said the outsourced business model we had pioneered for printing services, where we completely managed and maintained the amenity, as well as developed custom software to suit the apartment building context, would perfectly fit coffee service as well.” 

Upon further investigation, Treble identified striking parallels between mobile coffee and printing amenities in residential spaces. “They both involve hardware, a consumable supply of goods that need to be managed and a tendency for ‘abuse’ by select residents.” Thus, SipWithMe was developed, and the parent company, WithMe, Inc., was formed.  

SipWithMe elevates the resident experience through reliable, easy-to-use technology, barista-quality beverages, and locally sourced coffee - all while helping properties decrease their spend, control costs and save time. The service incorporates the same groundbreaking allowance technology first introduced through PrintWithMe, giving owners and operators full control over resident usage.

SipWithMe was met with overwhelming response, and it is currently disrupting multifamily coffee in major markets all across the United States. 

Building a Team 

Visit the WithMe website or any of its social accounts, and you will quickly discover that culture is of the utmost importance. However, building that culture was a lengthy process. Determined to personally confirm his theory that PrintWithMe was best suited for a direct sales approach, Treble spent more than two years tirelessly canvassing Chicago on his own, often logging more than 80 hours of work per week. 

Throughout the first four years of PrintWithMe, Treble built a small team of contractors and team members, but they all, admittedly, had a “work first” mentality, not unusual for a startup. Unfortunately, that mindset left little time or room for prioritizing culture. It wasn’t until years 4-6, when the team grew to 10, that Treble “started realizing that creating a genuinely positive culture would result in a competitive advantage and long-term benefits to the business.” 

While eloquent words about culture may look impressive on a computer screen, the true indicator of culture lies in employee retention and satisfaction. According to Treble, “We truly live out the values we post on our website. We don’t just pay lip service to them. I have also found that newer employees (those who joined in the last 1-2 years) have self-selected to apply to WithMe because of our clearly stated values. They are, therefore, more likely to stay with us, which is a virtuous cycle.” 

WithMe monitors Employee NPS twice per year, and satisfaction is consistently strong. Despite WithMe’s hypergrowth and the rise of negative employment movements like “The Great Resignation,” the company has also enjoyed relatively stable retention. 

Learning and Growing

For those with entrepreneurial aspirations, Treble’s greatest advice is to voraciously consume literature. He believes in taking the time to identify subject areas that are a source of weakness or challenge – and then reading books at every comprehension level to gain a well-rounded understanding of each subject. 

As Treble says, “Entrepreneurship is like an extreme sport. You need to rapidly learn new things merely to survive in an unforgiving environment.” 

In addition to educating himself through books, Treble has also found podcasts to be crucial to his success. He cites The Marketing Book and Recruit Rockstars as two of the most influential in building WithMe. 

Finally, Treble stresses the importance of finding steadfast mentors to help navigate the taxing and complex world of entrepreneurship. He counts Orazio Buzza at Fooda and Tim Thornton at PayPal as two of his greatest mentors. 

As evidenced by Treble’s path to not only launch WithMe, but to continue to deliver new tech-powered convenience, entrepreneurship is a journey, not a destination. It requires continual self-evaluation, self-reliance, self-discipline and self-confidence. 

Interested in learning more about Jonathan’s entrepreneurial journey? Connect with him on LinkedIn, where he regularly shares entrepreneurial insights and musings, and be sure to subscribe to his podcast, Multifamily Excellence, where he leads candid conversations with mutlifamily’s top minds.