Mission-Driven Tech: Inside PlanPerfect with Co-Founder Adam Wolford

Passion meets purpose in today's Wantrepreneur to Entrepreneur Spotlight featuring Adam Wolford, the visionary co-founder of PlanPerfect. Adam's journey from consultant to startup enthusiast to entrepreneur showcases the power of resilience and taking action. Through PlanPerfect, he's revolutionizing how nonprofits approach strategic planning, helping mission-driven organizations maximize their impact with streamlined tools. From exploring multiple startup ideas to finding the perfect co-founder in Sophia Shaw, Adam has discovered that entrepreneurial success comes not from perfect planning, but from simply being "in the game."

Hi, Adam! Thanks for joining us today. Tell us about your business. Who do you serve, how do you serve them, and what's the impact that your business and work makes?

At PlanPerfect (planperfect.co), we help small to medium-sized nonprofits build, execute, and report on strategic plans with ease. Nonprofit leaders often struggle with scattered plans, complex reporting, and limited resources—our platform simplifies the process by providing guided strategic planning, real-time progress tracking, and collaborative tools that keep teams aligned and accountable.

By making strategic planning more accessible and actionable, we help nonprofits increase their impact, strengthen fundraising efforts, and save valuable time. With PlanPerfect, organizations can move from vision to execution with clarity, ensuring they stay focused on what matters most: driving meaningful change.

Tell us about the moment you finally felt like you went from wantrepreneur to entrepreneur.

For me, the moment came in 2023 when I took the leap from a salaried job into the world of entrepreneurship. At first, I set up consulting arrangements just to keep the lights on while exploring startup ideas. But the real shift happened when I went from relying on a company for my livelihood to relying on myself—building something with my own (virtual) hands. It was both exhilarating and terrifying, but it taught me two things: (1) I’m capable of anything, and (2) the most important thing an entrepreneur can do is simply be in the game.

Describe the moment or period in your life/career that motivated you to make the entrepreneurial leap.

For me, business school was the catalyst that encouraged me to explore entrepreneurship. From there, I joined a Series A startup in 2021, where I got my first real taste of the startup world. That was just the beginning.

In 2023, I worked solo to develop a startup but kept hitting roadblocks—whether it was personal fit, not solving a real problem, or cofounder breakups. Then, in 2024, everything changed. When Sophia sent me an email with an idea and a week later, I drove two hours across Florida to meet her in person, and from that moment, we knew we had something worth building.

We started working together soon after, and as I wrapped up other projects, I transitioned to working full-time on PlanPerfect. Building alongside someone you deeply respect and care about makes the journey just as fulfilling as the destination. We work hard for each other and our clients, we have fun in the process, and we couldn’t be more excited about the future of PlanPerfect!

Describe a tool, service, or software that has been a game-changer for your business. How does it contribute to your success?

For us, Fireflies.ai has been a game-changer. As a growing business, it’s inevitable that we have to divide and conquer meetings due to calendar conflicts and the need to stay productive. Without this tool, we’d be stuck taking notes during calls, which would distract us from truly listening to our customers.

For us, hearing our customers, meeting them where they are, and ensuring we’re the right fit is what sets us apart. Fireflies makes that possible by capturing every conversation, allowing us to stay present in meetings while still having detailed records to reference later.

We know that success is very often a non-linear path. Tell us about a failure, pivot point, or lesson that changed your course or direction and helped to get you where you are today.

For most of 2023, I spent the year exploring startup ideas—a journey filled with failures and lessons. My first concept seemed promising, but after months of customer discovery and prototyping, I realized it wasn’t a game-changer for my target audience. In hindsight, I could have validated this in weeks, not months, which taught me a crucial lesson: listen to your customers' real needs, not just what you want to hear.

My second idea had real demand, and I started building it—until a similar product launched at the same time, forcing me to reassess my approach to competition. I learned that competition isn’t a bad thing; it validates the problem, but differentiation comes down to execution, distribution, and customer experience. My third idea got even further, but I hit a wall—I wasn’t obsessed with the industry. Without deep passion or experience, I knew I’d struggle against founders who lived and breathed the space.

The final “failure” was the startup I took the furthest, securing pre-sales and working with a technical co-founder to build the product. But when my co-founder exited to take a full-time job, it reinforced the most valuable lesson of all: your team is everything. That’s why finding Sophia was a game-changer. I deeply trust and respect her, and even when things get tough, our shared vision makes it all feel worth it.

What unconventional strategy did you employ that significantly impacted your business?

Our secret sauce has always been the people. Early on, many of our vendors came from our personal network, creating an inherent trust that allowed us to move quickly in developing our brand and website. For vendors we sourced externally, we prioritized those who understood our mission and were familiar with our nonprofit customers—ensuring alignment with PlanPerfect’s core values.

Most importantly, our incredible team of interns from Kellogg School of Management at Northwestern has been instrumental in our success. Their dedication, talent, and shared alma mater have made building PlanPerfect even more rewarding. Without them, we wouldn’t be where we are today!

What’s something you wish you knew sooner that you’d give as advice for aspiring or newer entrepreneurs?

My advice is simple: go do. While learning from the greats and absorbing knowledge is valuable, the best lessons come from first-hand experience—by taking action, making mistakes, and adapting along the way.

This was a hard lesson for me as a former consultant, where success was often tied to planning rather than doing. But in entrepreneurship, momentum is everything. I’ve learned to prioritize action while still recognizing when to slow down. Progress comes from moving forward, not just preparing to move.

Want to dive deeper into Adam's work? Check out the links below!

• Visit PlanPerfect's website planperfect.co
• Find PlanPerfect on LinkedIn
• Follow PlanPerfect on Facebook
• Find PlanPerfect on X @plan_perfect_co
• Follow PlanPerfect on Instagram @plan_perfect_co
• Connect with Adam on LinkedIn: Adam Wolford