Wantrepreneur to Entrepreneur | Start and Grow Your Own Business 1118: STRATEGIC PLANNING with technology AND your heart w/ Adam Wolford & Sophia Shaw
In this episode, we dive into the world of strategic planning with Adam Wolford and Sophia Shaw, the co-founders of PlanPerfect—a technology-driven platform making strategic planning accessible and actionable for nonprofits. With deep expertise in both nonprofit leadership and tech innovation, Adam and Sophia share how they’re bridging the gap between traditional strategic planning and cutting-edge AI-powered solutions.
Whether you’re running a business or a nonprofit, this episode will help you understand why having a clear roadmap is essential for success—and how to ensure you actually execute on it. They also share the realities of transitioning from traditional careers to entrepreneurship, the power of partnerships, and the importance of just getting started.
💡 What You'll Take Away For YOUR Business
🚀 Why strategic planning isn’t just about having a plan—it’s about execution
🛠️ How technology and AI can simplify strategic planning for any business
💰 How nonprofits and for-profits can adopt the same growth principles
⚡ Why removing ego is the key to getting teams aligned
📊 The #1 mistake businesses make in strategic execution (and how to avoid it)
👥 The power of co-founder partnerships—and how to find the right one
⏳ Why speed and iteration beat over-planning in entrepreneurship
📝 About Adam Wolford & Sophia Shaw
Adam Wolford has over a decade of experience in technology development, strategy, and operations, with a focus on helping organizations scale and operate more efficiently. He began his career at Accenture and Deloitte before transitioning into the startup world, where he led a product team at a Series A tech company. In addition to his work in technology, Adam has been actively involved in the nonprofit sector, serving on boards and volunteering. He is particularly interested in the intersection of technology, strategy, and impact—helping teams leverage the right tools and strategies to drive meaningful growth and results.
Sophia Shaw is an accomplished nonprofit leader and board governance expert with over 30 years of experience and a deep passion for mission-driven impact. As the former CEO of the Chicago Botanic Garden, trustee, board president, donor, volunteer, consultant, and professor of social impact at the Kellogg School of Management, she brings deep experience in organizational strategy, board leadership, and philanthropy.
🎯 Adam & Sophia’s BEST Piece of Advice for Entrepreneurs
"Stop overthinking and just start. The best way to learn is by doing."
💡 Key takeaways from their advice:
✔ You don’t need everything figured out—the roadmap will evolve as you go
✔ Failure isn’t fatal—iterating quickly is more important than getting it right the first time
✔ Execution is everything—a plan that isn’t acted upon is just a document
💡 Actionable Takeaways
✅ Write down your vision—if your team can’t clearly articulate it, execution will fail
✅ Test your ideas quickly—waiting for the “perfect plan” is a waste of time
✅ Embrace technology—strategic planning tools like Plan Perfect can help you move faster
✅ Find a partner you trust—a strong co-founder relationship can make or break your success
✅ Make strategic planning a habit—don’t just plan once; revisit and adjust regularly
🔗 Links & Resources