Entrepreneurship is shifting and the playbook is outdated with Jeffery Kaplan

Mission Driven You

Episode Description:

What does it really take to build a thriving startup outside of Silicon Valley? In this episode of Mission Driven You, I sit down with Jeffrey Kaplan, the Director of Venture Asheville, to discuss the evolving world of entrepreneurship, the future of startup ecosystems, and the critical skills founders need to succeed.

We explore:

• Why traditional startup playbooks don’t work everywhere and how regions can develop their own strengths.
• The biggest mistakes new founders make—and how to avoid them.
• Why AI and automation are changing the game, allowing startups to scale with smaller teams than ever before.
• How mentorship, community, and consistency create sustainable entrepreneurial success.

If you're an entrepreneur—or just someone fascinated by how businesses grow in the real world—this episode is packed with insights on how to think and act like a founder, no matter where you are.

Show Notes:

Guest Information:

• Jeffrey Kaplan – Director of Venture Asheville
• Website: Venture Asheville
• Entrepreneurial Competency Assessment: Thee13.com

Key Topics Discussed:

1. Why Startup Ecosystems Matter

• The myth of replicating Silicon Valley—why trying to copy the Bay Area doesn’t work.
• How regional strengths should shape startup growth strategies.
• Asheville’s unique entrepreneurial landscape: retiree wealth, high tourism, and rising young professionals.

2. Common Mistakes & Lessons from Successful Founders

• The #1 regret of most entrepreneurs: not focusing enough.
• Why lone founders struggle—and the power of co-founders in long-term success.
• Product-market fit vs. great ideas—why your customer’s emotional experience matters more than you think.
• The most overlooked factor in startup success: cash management, not just fundraising.

3. The Role of Coaching, Community & Consistency in Entrepreneurship

• Jay Shetty’s Three C’s: Coaching, Consistency, and Community—and why all three must be in balance.
• The Want, Need, Win method used in founder peer groups for accountability and mentorship.
• Why entrepreneurs need a place to be vulnerable—and how peer mentorship reduces isolation.

4. The Rise of AI & The No-Employee Startup

• How AI is reducing the need for large teams—allowing founders to scale businesses more efficiently than ever.
• The future of automation in legal work, content creation, and admin-heavy tasks.
• Could a one-person AI-powered unicorn startup become reality?

5. The Future of Entrepreneurship & Solving Big Problems

• Why we need entrepreneurs more than ever to tackle climate change, wealth inequality, and local economic resilience.
• The difference between throwing money at problems vs. real entrepreneurial solutions.
• Why global challenges need hyper-local solutions—and how a regional approach to startups can create lasting change.

Reflection Questions for Listeners:

• If you’re starting or running a business, what’s your biggest blind spot—focus, cash flow, or market fit?
• How can you build a stronger entrepreneurial support system around you?
• What industries do you think will be transformed the most by AI-driven startups?

Resources Mentioned:

• Take the Entrepreneurial Competency Assessment: VE13.com
• Book Recommendation: The E-Myth by Michael Gerber (on the difference between a technician and an entrepreneur)
• Slow Change Newsletter on Substack → [Link in show notes]

Join the Conversation:

• Follow Jeffrey Kaplan on LinkedIn for insights on startups & venture growth.
• Subscribe to Mission Driven You on Apple Podcasts & Spotify.
• Join Will’s Substack for deep dives into entrepreneurial resilience & slow, sustainable change.

💡 Final Takeaway:

"The next generation of startups won’t come from Silicon Valley—they’ll come from founders who build with focus, leverage their community, and embrace the power of AI."