Executive Coaching for founders

Building something from nothing is hard.

Make it easier.

I’m James Sheppard.

I help founders accelerate their impact with less stress.

Hi, I’m James Sheppard, a 3x startup founder turned executive coach. I’ve built three venture-backed companies (with two exits, so far). But more importantly, I’ve been exactly where you are.

I know the pressure, the constant grind, the emotional toll, and the overwhelming stress that comes with leading a startup. I’m the coach I wished I had when I was building my companies. Now, I work with founders like you, guiding you to peak performance without the burnout.

My approach? It’s all about the Inner Game—helping you master the mental and emotional side of leadership. The truth is, running a company isn’t just about the right strategies or funding; it’s about how you show up when things get tough. Your emotional resilience, decision-making clarity, and ability to reset quickly under pressure make all the difference.

Whether you’re struggling under the weight of high expectations or navigating the complexities of growth and scale, coaching can make a massive impact on your leadership, mental well-being, and business success.

How Can I Help You Best?

The Foundation Phase

You’re feeling the weight of unmet expectations, investor pressure, and a growing sense of self-doubt. It’s easy to get stuck in the struggle, but the key is getting back on your A-game quickly. With coaching, you’ll gain the clarity and confidence to lead effectively, make better decisions, and recover from setbacks faster.

The Scale Phase

You’re scaling fast, but the challenges are different now—team dynamics, communication breakdowns, and the pressure to keep growing while staying aligned with your vision. My coaching helps you strengthen your leadership, improve team alignment, and sustain peak performance as you scale.  Burnout doesn’t need to be the price of success.

In both cases, Inner Game work is at the core of what I do. We’ll focus on self-awareness, resilience, and mental clarity, so you can lead with confidence and creativity—no matter how high the stakes.

Whether you’re looking to sustain your success or need help getting back on track, I’m here to help you perform at your best—consistently. Schedule a complimentary discovery session.

Testimonials

 James is my secret weapon.

With James on my team I make better decisions, with greater clarity and a whole lot less stress.

Rebecca Kirstein Resch, CEO & Co-founder, Inqli 

  • James has helped me navigate countless problems, decisions, and strategies related to my business. He’s able to quickly come up to speed on the situation at hand and strip away the noise so that I can focus on the core issue that needs to be addressed. 

    I often go into a conversation with James thinking that I have a specific problem that I need help with and then come away with a much clearer understanding of the bigger picture and what immediate steps I need to take to move the overall strategy forward. Having him in my corner has been invaluable to the success of my business.

    Arash Boostani, Co-founder & CTO, Beam Financing Technology

  • Getting coached by James was exactly what I needed.  I give him a lot of credit for coaching me through a very full time in my professional life and helping me see opportunities in each challenge I faced. 

    My needs and focus moved through three distinct phases over our nine month engagement.  James held the north star of our agenda over that time so that our conversations built on each other and progress was easy to see.

    I strongly recommend him to anyone navigating an immense change.  He is an engaged sounding board and valuable guide along the way.


    Freeman White, Head of Product, M-KOPA

  • James's dedication to cultivating high-performing teams is evident in every aspect of his work. We witnessed immediate improvements in our team effectiveness and are actively applying the insights gained for lasting results. James possesses remarkable talent and passion and I wholeheartedly recommend him to elevate your skills and team dynamics.

    Diane Zapata, Director, Second Harvest Food Bank