We were lucky to catch up with Amy Kauffman recently and have shared our conversation below.

Amy, thanks for joining us, excited to have you contributing your stories and insights. Alright, so you had your idea and then what happened? Can you walk us through the story of how you went from just an idea to executing on the idea

Let me take you back to the summer when the idea for my tech company first sparked. I was running another business in the tech space, and every conversation with my customers seemed to revolve around one glaring problem. It wasn’t just one or two clients—every single one was venting about the same issue.
I remember walking out of a coffee shop after yet another chat with a frustrated customer. The summer heat was bearing down as I crossed the parking lot, and it hit me: Why doesn’t a solution for this exist? Then came the next thought: Maybe I can build it.
Immediately, self-doubt jumped in. I didn’t have a tech degree, and I certainly didn’t have $200k sitting around to fund a software project. What did I know about building a tech solution? The idea seemed far-fetched, but it wouldn’t let me go.
The very next day—this is where it gets wild—I got an email in my inbox about a course: “How to Create a Software Company in 6 Months.” I didn’t think twice. I signed up on the spot.
That course became my roadmap. One of the first lessons was about “idea extraction”—a fancy way of saying, go talk to your customers. Instead of guessing what they needed, I got on the phone with over 80 potential users and asked them directly. I listened as they described their pain points, frustrations, and even what they imagined a solution might look like. By the end of those conversations, I didn’t just have an idea—I had a crystal-clear picture of the problem and how to solve it.
Next, I sketched out wireframes—simple visuals to show what the software could look like. I circled back to those same customers, showed them my ideas, and asked, “What do you think?” When they got excited and asked, “What’s next?” I gave them my pitch:
“I’m looking for five founding users at $3,500.”
Then I held my breath and waited.
To my amazement, a few of them said yes right away. They didn’t just agree; they mailed me checks for $3,500 each—Clif Bar, Honest Tea, and Cabot Cheese, to be exact. And get this: at that point, I didn’t even have an LLC! I had built enough trust that they were willing to bet on me and my vision.
With their investment, I hired a developer, built the MVP, and launched the platform less than four months later.
Looking back, what stands out most to me is how little I knew going in—and how much I learned by simply talking to my customers. I didn’t guess what they needed or fall in love with my own idea. Instead, I let them guide the process. That’s the lesson I’d pass on to anyone starting a business: don’t build in isolation. Get out there, ask questions, listen closely, and let your customers shape the solution.
You don’t need all the answers to start—you just need to start.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m someone who thrives in the tension between quiet moments of joy and an insatiable drive to make the most of this life. Whether I’m laughing with my girls, wrestling around on the living room floor, or standing on the edge of an adventure, I’m fully present. Those moments light up my soul. But just as much, I’m fueled by purpose—the relentless desire to grow, improve, and accomplish something meaningful with the time I’ve been given.

Outdoors is where I feel most alive—wind in my hair, sun warming my skin, the grounding hum of nature all around. And when life calls for pause, you’ll find me savoring a blissful cup of black tea, letting its warmth remind me of the beauty in simplicity.

I’m intentional about everything I do. Whether it’s guiding executives to step boldly into their potential, helping leaders clarify their vision, or building platforms that spark lifelong learning, I believe every action should align with a greater purpose. It’s not about being busy—it’s about making every moment count.

I’m also a builder—not just of businesses, but of opportunities for connection, clarity, and transformation. I co-founded an education platform because I believe in the power of curiosity and growth to change lives. I invest in people and ideas because I see potential as a gift meant to be nurtured.

At my core, I’m a woman of contrasts. I treasure the spontaneity of adventures with my daughters, but I’m fiercely disciplined in my practices and pursuits. I love moments of lighthearted play but carry a deep-seated drive to accomplish, grow, and give back. Every choice, every action, is rooted in purpose.

If you truly want to know me, picture this: I’m outdoors, my girls by my side, hearts racing from some spontaneous escapade. The sun is setting, the world feels both expansive and close, and in my hands is a cup of black tea—my grounding bliss, my moment of gratitude for a life lived with intention, joy, and fierce resolve.

Can you talk to us about how you funded your business?

Funding your business – tell us the story of how you put together the initial capital you needed to start your business?
At the very beginning of my journey building a tech company, I had no idea how I was going to fund it. What I did know, though, was that the problem I wanted to solve was real, and companies were feeling the pain. So, I started where I could—with conversations.
I reached out to companies that struggled with the exact issue my tech would address and asked for interviews. These weren’t sales calls; they were genuine conversations. I wanted to understand their frustrations and see if my idea resonated. To my surprise, everyone I spoke to lit up at the idea of a solution. At the end of each chat, they’d say something like, “Keep us in the loop—this sounds amazing.”
Encouraged by their enthusiasm, I created wireframes—a rough blueprint of the solution I was envisioning. Then I circled back to those same people for Zoom calls, walking them through my vision. Each time, the response was the same: “This is incredible! So, what’s the next step?”
That’s when I’d take a deep breath and deliver my pitch—the one I’d rehearsed in front of my mirror a hundred times.
“I’m looking for five founding users at $3,500 each,” I’d say, my heart pounding in my chest. And then I’d shut up. No follow-ups, no extra words. Just silence, waiting for their response.
And wouldn’t you know it? Three companies—Clif Bar, Honest Tea, and Cabot Cheese—said yes. They didn’t just say yes; they wrote checks for $3,500 each, made out to me, Amy Kauffman. I didn’t even have an LLC at that point, but I’d built enough trust that they didn’t hesitate.
With that $10,500 in hand, I got to work. I hired a developer, built the MVP, and just a few months later, we launched our tech platform.
Looking back, that experience taught me a powerful lesson about funding: You don’t always need a huge investor or a perfect business plan. Sometimes, all it takes is listening, showing people you understand their pain, and building trust. When you do, people will believe in your vision—and sometimes, they’ll even write you a check to prove it. It’s hard to get money when we don’t ask for it.

Conversations about M&A are often focused on multibillion dollar transactions – but M&A can be an important part of a small or medium business owner’s journey. We’d love to hear about your experience with selling businesses.

“Why don’t you want to sell your business?” Uncle Rodger asked, leaning back in his chair and looking at me like he already knew the answer. “Is it because you want to keep the business… or because you don’t want to quit?”
It hit me like a gut punch. Quit? Was that really what this was about? Was I holding on to something, pouring years of my life into it, just because I didn’t want to let go?
I sat there, stunned, realizing how much truth was packed into that question. I didn’t want to quit. That was it. And honestly, it wasn’t a noble reason to keep a business alive. It was ego. The fear of failure. The embarrassment of walking away from something I had built from scratch.
And I know I’m not alone in this. I’ve seen so many entrepreneurs do the same thing. They cling to their businesses like it’s their baby. They can’t imagine letting it go or, heaven forbid, seeing it fail. The idea of handing it over to someone else feels like a betrayal. The shame, the judgment—it’s overwhelming.
But here’s the thing: clinging out of fear or pride isn’t what a business deserves, and it’s not what I deserved either. When I realized my tech company wasn’t “setting my soul on fire” anymore, I knew deep down it was time to move on.
It wasn’t easy, but I made the decision to sell. And when I did, something incredible happened—I saw the business thrive in the hands of someone who had the passion and vision to take it to the next level. Someone who was excited to run it with joy and energy.
That was the lesson for me. Letting go isn’t failure; it’s recognizing when you’ve done your part and when it’s time to let someone else step in. As entrepreneurs, we start these businesses because we’re passionate, but sometimes, the bravest thing we can do is step aside and let someone else carry the torch.
So, if you’re thinking about selling your business someday, ask yourself this: Are you holding on because you truly love it? Or are you holding on because you’re afraid to quit?

Contact Info:

• Website: https://coachofceos.com/
• Linkedin: https://www.linkedin.com/in/amy-kauffman-a2691417/

Image Credits

Reneé Veniskey