It all started with Jonathan Treble facing a problem everyone can relate to. More than a decade ago, he had trouble printing concert tickets. That frustration led him to start a new company in 2014 that evolved into providing tech-enabled services for apartment buildings. As CEO, he’s grown WithMe Inc. to become a highly successful, profitable business that counts thousands of multi-family apartment locations throughout the U.S. as its customers.
Initially, Treble’s startup partnered with a few hundred independent coffee shops, where it placed its PrintWithMe self-serve kiosks. It was doing okay, but soon realized a better, much bigger market to target with these kiosks was the huge, expanding multi-family apartment segment.
From 2019 to 2024, WithMe achieved an astounding 1109% in revenue growth — a milestone that reflects the company’s rapid expansion across the multifamily housing market and, as the company states, “its sustained investment in people, product excellence, and customer experience.”
WithMe’s amenities are now available in more than 5,300 locations nationwide, serving some two million apartment homes. It expanded to coffee in 2021 and has grown that offering to serve multifamily properties, also targeting student housing, higher ed, commercial offices, and the hospitality industry. Both PrintWithMe and SipWithMe are designed to streamline operations for property managers while delivering reliable, user-friendly experiences for residents.
A graduate of the Wharton School, Jonathan Treble later became a manager in the large product and tech team at pre-IPO GrubHub. He credits part of WithMe’s success to seeing what scale looked like across different functional areas at GrubHub. Once he founded WithMe, he began learning valuable lessons about startup fundraising and hiring.
Steady Growth With a Smart Capital Strategy
“I got advice from a trusted mentor to bootstrap as much as I could to retain ownership. He didn’t think my business was really set up for venture rounds of funding,” said Jonathan. “And I think he was probably right. I’m happy I raised in dribs and drabs, slowly, because I still retain majority ownership today.”
How does WithMe now position its mission? It’s all about “delivering convenient technology-powered solutions that create elevated living experiences.” Its flagship subsidiary, PrintWithMe, now powers printer amenities and staff solutions at multifamily locations across all 50 states. And its newer subsidiary, SipWithMe, is making great inroads in disrupting the coffee amenity category in the multifamily housing industry.
Since its founding, capital efficiency and profitability have been major focuses. It became clear to me when I interviewed Jonathan for a Great North podcast episode that, once he found product-market fit within the multi-family market, he became deeply focused on scaling his team efficiently. Great North Ventures initially invested in WithMe in 2019 along with M25, Network Ventures, and New Stack Ventures, and we’ve been following Jonathan’s impressive success closely since then.
Smart Hiring and Culture Became Front-and-Center
It’s challenging for many startups to consistently recruit and retain top talent at the pace needed to support the growth of their business. Jonathan and his team at WithMe have clearly not been willing to settle when it comes to adding new team members.
“I made a bunch of hiring mistakes after my first large round of raising, which was $500k,” said Jonathan. “I read a couple of the classic recruiting books: ‘The Who Method’ by Geoff Smart and the other ‘Recruit Rockstars’ by Jeff Hyman. Those two books formed the backbone of our recruiting process. I took the processes I learned in those books and melded them together in a way that I thought made sense.”
Culture became extremely important to Treble after surviving and learning from his hiring mistakes.
The Awards Keep Coming
The WithMe team has grown to more than 100, many based in Chicago where it is headquartered, but it is proud to be a 100%-remote team working across the globe. It has been named by the National Apartment Association as a 2025 Top Employer. “Our team loves what they do and where they work,” said CEO Jonathan Treble.
In June 2025, WithMe was named to the 2025 Crain’s Chicago Business Fast 50 list, which honors the 50 fastest-growing companies in the Chicago area based on five-year revenue growth. WithMe’s service commitment has also garnered national recognition. The company’s Client Experience team was recently recognized with a Bronze Stevie® Award for Customer Service Department of the Year in Consumer Products & Services, and also earned a 2024 Gold TITAN Business Award for Customer Service.
WithMe has been named to the Inc. 5000 list of fastest growing companies in 2021, 2022, 2023, 2024 and now 2025, their fifth consecutive year.
Product Expansion and Social Impact
In May 2025, WithMe launched the PrintWithMe Office Solution, a new multi-functional printer aimed at supporting on-site teams in multifamily and commercial workplaces.
SipWithMe, its coffee amenity service, has continued its expansion, having reached more than 500 installs nationwide as of October 2024. It previously had partnered with Groundwork Organic Coffee Roasters to launch SipWithMe in Los Angeles, expanding its reach with Certified Organic, ethically sourced specialty coffee options for residents in participating communities.
In April 2025, WithMe launched GiveWithMe, a corporate impact program formalizing its commitment to families, nonprofits, veterans, employees, and the environment. Through the HOPE (Helping Others Provide Ease) initiative within GiveWithMe, WithMe plans to contribute $100,000 in amenities to Ronald McDonald House Charities locations in 2025. What’s more, WithMe also continues to support community organizations through its Free Recycled Printer Program, donating refurbished printers to nonprofits that support children and families.
