BEN Founder Spotlight: Meet Jonathan Treble of WithMe

Jonathan Treble is the Founder of WithMe, a company bringing modern, tech-enabled amenities to multifamily properties, student housing, higher ed, coworking spaces, and beyond. Through its PrintWithMe and SipWithMe solutions, WithMe elevates the day-to-day living and working experience with amenities that drive joy while making work easier and costs more predictable.

This week, Jonathan enters his third round of the BEN Signature Program, a highly personalized 12-month advisory experience designed to help scale-up founders and CEOs navigate their biggest growth challenges. The program pairs business leaders with seasoned advisors who’ve built and scaled companies themselves, providing the kind of insights that stick long after the sessions end.

Jonathan Treble and former BEN CEO Kay Henze at BEN’s Celebration of Entrepreneurship in April 2024

As Jonathan begins this new chapter, he shares what keeps bringing him back to the program, how WithMe has grown alongside his own leadership, and what’s next on the horizon.

Q&A with Jonathan Treble

1. What made you decide to go through the BEN Signature Program for a third time?

Every time I’ve gone through the BEN program, I’ve walked away with priceless insights that have helped me transform my business and get through each distinct phase of growth. First from $5M to $10M and then from $10M to $20M. Now that we’ve surpassed $25M, and I’m contemplating a step back from the day-to-day of my business onto a board-level role, I have a whole new set of considerations to think through and I’m sure BEN will be invaluable yet again.

BEN has this unique way of curating really thoughtful, experienced voices. Leaders who’ve built and scaled companies before. And they’re not afraid to challenge your assumptions. They don’t sugarcoat things. They ask tough questions and help you pressure-test ideas before you roll them out.

Going back to BEN for a third time felt less like a “nice to have” and more like a necessary step to help me see the big picture, gut-check our strategy, and make sure we’re still growing the right way, not just the fast way.

2. What are the biggest takeaways and successes WithMe has seen through each round of the program so far?

Each round of working with BEN has helped us level up in a pretty meaningful way, just in different seasons of the business.

The first time I went through BEN, I was deep in day-to-day execution. That experience helped me zoom out, adopt a company “operating system,” hire a strong COO (who was one of my BEN advisors), align my revenue team, and start working more strategically across the board. That shift in mindset made our operations tighter and sped up decision-making.

The second round was more about pressure-testing our growth strategy and rounding out our executive team. We sharpened how we track performance — clearer KPIs, more predictability in our revenue model, and more accountability across teams.

3. What is the biggest change you see in yourself as a founder and leader, as a result of your work with BEN Advisors?

BEN has helped me shift from doing to building. In the early years, I carried a lot of the weight myself – like most founders do. But BEN challenged me to step back, empower others, and build systems that don’t rely on me being in every room or making every decision.

The advisors in those sessions bring a mix of tough love and empathy. They’ve been in the trenches, and they get it. So their feedback lands differently. It pushes you, but in a way that’s rooted in generosity. That really helped me evolve into a more thoughtful, systems-minded leader.

It also gave me permission to lead in a way that reflects our values. We’ve always cared about more than just profit. Whether it’s launching our employee ownership model, working with veteran service orgs, or designing tech that actually makes people’s lives better, we’re trying to build a company that does good while doing well. BEN helped me build the kind of foundation where that purpose doesn’t get lost as we scale.

4. What would you tell a founder who was considering the BEN Signature Program?

If you’re serious about not just scaling your company, but growing as a leader, BEN is worth it. But go in ready to be challenged. It’s not a pat-on-the-back kind of environment. The advisors will push you to confront blind spots and think differently.

For me, that kind of feedback has been invaluable. You also get a network of peers who are navigating similar challenges, and that support doesn’t end when the program does. Just be coachable and willing to engage.

If you’re willing to engage with that kind of humility and vulnerability, the upside is huge. You’ll walk away with sharper instincts, a stronger game plan, and a support network that actually sticks with you beyond the program. It’s absolutely been worth it for me, every single time.

5. You are running for Congress in 2026. What inspired you to do so?

This decision comes from personal experience and a deep sense of responsibility. A few years ago, I needed brain surgery – life-threatening, urgent – and I struggled with insurance throughout the process. That moment opened my eyes to how broken our healthcare system really is, especially when time is critical and the system still fails to show up.

The best place to fix healthcare, and improve the lives of all Americans, is in Congress.

6. Any lessons learned already from the challenges and opportunities of running for office and running a high-growth company?

A lot carries over between lessons learned in running for office and running a high-growth company. In both cases, you need a clear vision, the ability to inspire people with your vision, and the tenacity to stay resilient when things get tough.

At WithMe, I also had to learn to delegate—and I mean really delegate—and trust the people around me to lead. The same is true on the campaign side. You can’t do everything yourself, and you shouldn’t try. It’s about bringing together the right people who believe in the mission and letting them run.

And then there’s the resilience piece. Startups are full of curveballs. So is campaigning. You’ll hear no. You’ll hit walls. But if you’re clear on why you’re doing it, you keep moving.

For me, both efforts are tied to the same mission: building stronger communities. Whether it's through better tech in housing or policy work on healthcare and education, it all comes back to helping people live better lives.

Jonathan’s journey with WithMe reflects the kind of bold leadership and purpose-driven growth that the BEN Signature Program is designed to support. As he embarks on his third round, we’re proud to continue walking alongside him, providing the candid insights, experienced voices, and trusted network that help founders scale their companies and themselves.

At BEN, it’s never just about the next milestone. It’s about helping leaders like Jonathan grow the right way, build lasting impact, and stay connected to a community of peers and advisors who push them to think bigger.