Recently I spoke with John Larson, founder of Zipwhip, a company that transformed how businesses communicate with customers through text messaging. John grew up in Michigan, learning the ins and outs of entrepreneurship in his father’s small businesses before building a career around innovation in business communication. In our conversation, John shares how fostering strong communities and trusted networks has been central to his success, the role of perseverance and focus in building a company from the ground up, lessons learned from raising capital and navigating enterprise deals, and how AI is shaping the future of communication. He also offers practical advice for young entrepreneurs on balancing passion with focus, embracing feedback, and leading teams to achieve meaningful impact.
The Journey Begins with Family Businesses
Griffin Connolly: Welcome, John. Let’s start with your background — your education, upbringing, and the big-picture view of your journey so far.
John Larson: I grew up in Plymouth, Michigan, where my father owned several small businesses, including a frame shop and art gallery downtown. I spent a lot of time there, watching and helping him run things. It was a tight-knit, small-town environment — the perfect place to learn what entrepreneurship really means.
My dad worked incredibly hard, starting early every morning and still making it home for dinner. Seeing that balance taught me that entrepreneurship is all about choosing your hard. Whether it’s running a small shop or building a larger company, both take grit and sacrifice — but the reward is that sense of ownership and purpose.
Working in the store gave me my first lessons in customer service, responsibility, and what it takes to build something from the ground up. I saw how personal small-town business could be and how much it mattered to people. Those experiences planted a seed in me to someday start something of my own.
I always knew the corporate route wasn’t for me. I wanted the freedom to shape my own path, even if it meant taking the tougher road. Over time, I learned that entrepreneurship really is the hardest path. And that passion and purpose are what keep you going through the grind. You can’t fake that.
Taking the Leap into Entrepreneurship
Griffin Connolly: In the mid-2000s, you were working a traditional job before taking the leap into entrepreneurship. What made you see opportunity in the communications space?
John Larson: My entrepreneurial journey really began with one big bet on text messaging. Back then, texting was clunky, you had to press the same key multiple times to type a single letter, but I saw its potential. It worked on every phone, required no downloads or logins, and instantly connected people. That simplicity and emotional immediacy fascinated me.
I became focused on one question: How can consumers communicate with businesses through text? That became the problem I dedicated the next two decades to solving.
In 2007 and 2008, investors weren’t convinced. Most were betting on BlackBerry Messenger, a closed network, while I believed in SMS — an open, universal system that could reach anyone with a phone. That openness became its greatest strength.
Over time, those 160-character messages evolved into one of the most efficient communication tools ever. Businesses could reach customers instantly and personally, while consumers could respond on their own time without the frustration of calls or hold music. Texting became the new standard for meaningful, fast connection.
For me, it all came down to one idea: communication is about efficiency, connection, and time. Money and products can be rebuilt — time can’t. Text messaging, at its best, gives people a little of that time back, and that’s what made it worth building around.
Building Together: The Power of Community in Entrepreneurship
Griffin Connolly: I’m really interested in the community aspect of entrepreneurship. What does community mean to you, and why is it so important?
John Larson: Community has always been central to everything I’ve done. In my early twenties, I helped start the Detroit Men’s Club with a mentor. We brought together artists, business leaders, and creatives over meals to share ideas. It was my first real experience seeing how powerful genuine connection can be.
I’ve always believed that business success depends on three things: knowledge, network, and passion. You need curiosity to keep learning, passion to push through challenges, and a network of trusted people to help your ideas grow. Too many entrepreneurs keep their ideas hidden, but ideas can’t develop in isolation. They need community to take shape.
Networking, to me, has never been transactional—it’s about real connection. Even in college, I loved introducing people and building relationships the old-fashioned way: showing up, shaking hands, and looking people in the eye. Trust can’t be built through a LinkedIn message; it happens in person.
That philosophy shaped my work at ZipWhip. Our partnerships with major carriers like Verizon and AT&T were built entirely on trust and long-term collaboration. Those relationships became the foundation of the company’s success and eventual sale.
Now, as I focus on investing and advising, I see community as even more vital. It’s about trust, collaboration, and shared success. Community isn’t optional—it’s the foundation for building, growing, and sustaining any business.
The Changing Landscape: How AI is Redefining Human Connection and Efficiency
Griffin Connolly: How do you see AI changing the networking side of entrepreneurship? Will community become less important, or will human connection still matter?
John Larson: I was actually testing an AI voicemail assistant this morning. It intercepts calls, asks follow-up questions, and sends me a text summary—great for saving time, in theory. But the first caller hated it. He found it uncomfortable talking to a bot. That moment reminded me that technology isn’t just about capability, it’s about experience.
AI is incredible for internal operations: automating workflows, summarizing meetings, and speeding up decisions. But when it faces the customer, the challenges grow—issues like robotic tone, misinterpretation, and loss of trust. Once AI becomes reliable and emotionally intelligent, though, it will drive major efficiency gains without sacrificing the human touch.
That’s the mindset behind my new company, Ambassador. We’re not a root-level AI company by some definitions, but we use it across everything we do—aggregating data, automating workflows, and accelerating decisions. With a 22-person team, we’re aiming for $10 million in annual recurring revenue within two years. That growth would’ve been nearly impossible a decade ago.
AI lets small teams achieve more with fewer resources. It doesn’t replace people; it amplifies them. And no, I don’t believe AI will make community less important. If anything, it makes it more vital. Technology will handle efficiency, but humans will always drive trust, creativity, and vision. In the end, relationships are what bring ideas to life.
The Exit: Letting Go, Lessons Learned, and the Power of “We”
Griffin Connolly: Zipwhip’s story is incredible. You built it over nearly fifteen years before it was acquired by Twilio. What was that experience like, and how did it feel to walk away from something you’d dedicated so much of your life to?
John Larson: It’s hard to describe. Zipwhip took fourteen and a half years to build, and much of the final push happened during the pandemic—nine straight months of Zoom meetings with no in-person contact. But the timing couldn’t have been better. The communications sector was booming, Twilio’s stock had skyrocketed, and after years of grinding, our team was burned out. I told our board, “Now’s the time. Let’s sell.” Everything aligned perfectly.
Still, stepping away was emotional. After so many years, it was bittersweet. Gratifying but strangely anticlimactic. Financial freedom doesn’t erase the sacrifices it took to get there.
As part of the acquisition, I stayed on for three years as VP at Twilio, overseeing global regulatory and carrier relations—our team’s specialty and a key reason for the deal. Helping Twilio integrate not just our technology, but our culture was a massive challenge. When my time there ended last July, it closed nearly eighteen years in that space.
Looking back, I’ve learned that entrepreneurship is as much a human journey as a professional one. You start out chasing your dream, but over time, you realize success isn’t about you, it’s about your team. Culture and people make or break a company. When everyone feels valued and purposeful, they’ll give their best, and that’s what truly endures.
Lessons from $850 Million: Things to Do Differently
Griffin Connolly: During our conversations, you’ve mentioned there are things you’d do differently with Zipwhip. Looking back, what are some of those lessons?
John Larson: There are countless lessons. We sold the company for $850 million, and I often joke about starting a blog called 850—not for the dollars earned, but for the 850 million lessons learned. Building a startup is a constant cycle of fumbling, learning, and adapting.
On a personal level, I wish I’d prioritized balance earlier. In the early years, I worked endlessly and tried to make everyone else happy while neglecting my own well-being. Passion can blind you—you want to solve every problem and keep pushing—but without balance, burnout is inevitable.
From a business perspective, the biggest lesson is focus. You can’t sell to everyone or please every investor. You need to define your ICP, your Ideal Customer Profile, and serve them relentlessly. It took us two years to find ours: insurance companies. A chief claims officer managing 6,000 agents could save millions annually using Zipwhip, so committing to a 3 year contract made sense. That clarity came only through trial, error, and listening.
My advice to entrepreneurs is simple: never assume, always test. Talk to customers. Seek negative feedback, as it’s where real growth happens. Most founders are three to five years ahead of their time, so don’t get discouraged when people don’t immediately get it. Focus on the one or two percent who do, and build for them.
Finding Fulfillment in the Journey
Griffin Connolly: I appreciate all of that advice. For my last question, I want to flip it a bit—what have you found most fulfilling in your pursuit of entrepreneurship, from your early days out of college up until now?
John Larson: That’s such a great question. For me, it feels a lot like being a kid again, like when I’d drain ten three-pointers in a row or juggle a soccer ball 150 times. I always loved that feeling of working at something until I finally nailed it. There was always a deep sense of pride proving to myself that I could do something, work through it, and figure it out.
That same feeling carried through my career. There were plenty of moments where we’d leave a meeting drained, not knowing how we’d solve a problem, but I’d tell the team, “We’ll figure it out by 2:00 tomorrow—go home, rest up.” And we always did. The fulfillment came from those victories, big or small, and from celebrating with the people who made it happen.
The most rewarding moments, though, were when employees would come into my office to thank me for believing in them. Hearing that your company has changed their life, that’s what sticks with you. Watching their self-esteem and confidence grow.
At the end of the day, entrepreneurship is really about the people. They’re your biggest investment and your greatest impact. And when you see them succeed, that’s when you realize why you started building in the first place.
Griffin Connolly: Thank you for all the insight. I appreciate you taking time to meet with me.
John Larson: Any time, Griffin. It was great talking with you today.
Read last month’s interview with Norm Allgood here.