Master the People Side of Scale

The constraint killing your velocity isn't technical—it's human.

I help venture-backed founders turn people friction into competitive advantage.

Sooner or later every founder feels it…

Despite best efforts, everything still flows through you

Working harder than ever but moving slower than you want

Endless firefighting leaves zero space for your best thinking

You thought the team was aligned, but execution tells a different story

Key hires aren't ramping fast enough and you can't figure out why

The pace is relentless, but everyone's running on fumes

Most founders think these are just the cost of scaling. There's a better way.

What if the friction wasn’t a flaw— just a signal?

Signals show you exactly where to level up.

Every point of friction—the busy mind, the overwhelm, the team misalignment—isn't a problem to fix.

It's an opportunity to upgrade.

When you learn to read these signals, everything shifts:

Endless firefighting becomes proactive leadership

This is how you create true leverage.

The result: A company that scales faster because the people side finally matches the technical excellence.

Ready to turn friction into leverage?

Busy mind becomes clear focus on what only you can do

Team misalignment becomes radical ownership at every level

Busy mind becomes clear focus on what only you can do

Communication gaps become precision execution

Endless firefighting becomes proactive leadership

Rebecca Kirstein Resch - CEO/Co-founder, Inqli

“I wasted months circling around on the same issues on my own.  James brought the perspective I was missing.  I should’ve engaged him far sooner!”

How to Work With Me

  • 1:1 COACHING

    Work with me one-on-one to develop the clarity and inner game needed to lead with power and sustainability. 

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  • TEAM COACHING

    Transform your leadership team into a high-functioning unit that thinks strategically and executes with intention.

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  • SPEAKING

    Bring sharp, actionable insights on leadership development and founder psychology to your conference or company retreat. 

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Hi, I’m James Sheppard

I've been obsessed with founder psychology and the human experience since my first startup. I've built three companies as a founder—two successful exits (so far) that taught me as much about leading people as moving product. I've advised Fortune 500 executives on navigating high-stakes decisions and spent years studying what separates founders who scale successfully from those who flame out.

Most discover the hard truth: the skills that got you here won't get you to sustainable scale. The companies that win long-term aren't just well-funded or well-positioned—they're well-led. And leadership isn't intuitive. It's learned.

I became the coach I wish I'd had during those late-night moments when the weight of it all felt impossible. If you're ready to upgrade your leadership operating system—let's talk.

Three Steps to Velocity With Ease

How Does It Work?

BOOK YOUR DISCOVERY CALL

Complimentary session to diagnose your biggest bottlenecks and determine which approach makes sense for you.

BUILD YOUR SYSTEM

Tailored 3-12 month plan designed around your specific bottlenecks, from decision overwhelm to team dynamics.

SCALE WITH CLARITY

Real transformation that gets you out of reactive mode and into strategic leadership—with measurable velocity gains.

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 

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

    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.

  • Freeman White, Head of Product, M-KOPA

    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.

  • Diane Zapata, Director, Second Harvest Food Bank

    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.

You are the most powerful lever in your company.

That means you’re also the biggest risk.

Under-invest in your own clarity, and your team inherits the fallout: misalignment, re-work and a culture of friction. 

But when you clean up the people sh*t—including your own—you unlock real velocity. A team that executes with precision, ownership, and clarity.


This is the highest-ROI investment you can make. Period.

5 ways you’ll know you want to talk to me and 5 that tell you not to bother.

Am I the Right Coach for You?

We’re likely a great fit if you...

See yourself as the highest point of leverage. You recognize that your growth as a leader will ripple across every area of your company—and you're ready to do the work to upgrade your inner operating system.

We're probably not a fit if you...

Value having a no-stakes space for real thinking. You see the worth in having a confidential thinking partner with no agenda—someone who's not trying to sell you, invest in you, or manage your emotions.

Care about personal fulfillment, not just business metrics. You want to build something meaningful while actually enjoying your life, relationships, and the process of leading—not just grinding toward an exit.

Want honest feedback and are open to growth. You're hungry for real, useful input that cuts through the noise, and you can hear difficult truths about your leadership as opportunities rather than attacks.

Think leadership is a craft worth mastering. You don't want to just manage people—you want to inspire them, retain them, and amplify their potential while building systems that scale beyond you.

Think coaching is "soft" or a nice-to-have. If you're looking for tactical quick fixes or see personal development as fluffy, you'll be frustrated. This work goes deep.

Want to fix your team without examining yourself. If you're convinced the problem is entirely "out there"—with your executives, market conditions, or bad luck—we'll hit a wall quickly.

Seek validation over transformation. If you want someone to tell you you're doing great and make you feel better, find a therapist or cheerleader. I'm here to help you see clearly and grow

Can't handle direct feedback without defensiveness. If you spin stories, deflect, or get triggered when challenged, the work won't stick. You need to be coachable to be coached.

Care more about winning than building something meaningful. I get it. I’ve been there. The question I have is, “Do you have even a vague sense that this alone won’t fulfill you?”