FAQ: Startup Coaching with James Sinclair

Everything You Might Be Wondering Before Booking a Call

Startup coaching isn't cheap. It isn't fluffy. And it's not one-size-fits-all. You're about to spend real money with a real human who might become a key partner in your founder journey. So it's only fair that you get straight answers to every question rattling around your head.

This page exists to clear up the fog. Nothing hidden. Nothing sugarcoated. Just transparent answers to the most common (and uncommon) founder questions.

🔍 The Basics

What exactly is startup coaching?

It's structured, high-pressure, high-trust co-building. Weekly calls, async support, pattern recognition, decision-making, and unblocking you fast. It's not therapy. It's not training. It's not advice. It's a partnership.

Is this like a business coach?

Only if your business coach has built and sold companies, coached hundreds of founders, and will text you back at 11PM before your investor meeting.

What do we actually do on a coaching call?

We work. We debug your decisions. We prioritize your roadmap. We roleplay your pitch. We clean your GTM. Whatever's highest leverage that week.

What does a typical engagement look like?

1 call per week (90 mins). Slack/text in between. Async problem-solving. Sometimes a second quick call if momentum demands it.

Do I need to prepare for sessions?

Not really. Show up honest. Have something real to work through. If prep helps you think better, do it. But I'll meet you where you are.

đź’µ Cost & Value

How much does this cost?

$5K–$11K/month depending on scope, stage, and intensity.

What do I get for that?

Speed. Pressure. Strategic clarity. And someone who has done this before, who isn't guessing.

Why so expensive?

Because we move the needle. I'm not selling time. I'm selling better decisions, faster traction, and fewer expensive mistakes.

Is there a cheaper version of this?

Not really. If you want watered-down advice or accountability coaching, you can find it elsewhere.

Do you ever do rev share or success-based models?

Sometimes. But only with existing relationships or after several months of paid work. No free rides upfront.

Do you take equity?

No equity up front. If we're still working together after 12 months, I may earn a 1.5% kicker. That's it.

⚙️ How It Works

Do you sign NDAs?

Not before the first call. Yes if we work together. I also sign an IP assignment. Everything we create together is yours.

Do you work with teams or just solo founders?

Both. But the core relationship is with one founder. The calls may include others depending on context.

What if I miss a session?

We reschedule or go async. This is a relationship, not a timecard. Life happens.

Do you have a fixed curriculum or framework?

No rigid curriculum. I have playbooks, tools, and frameworks. But everything is shaped around you and your context.

Can you help with pitch decks / hiring / product / growth?

Yes. All of it. I've helped founders raise rounds, fix positioning, hire execs, and break through plateaus, but you cannot hire me to assist with fundraising.

🤝 Fit & Chemistry

What if we don't vibe?

We won't work together. The intro call is a filter, not a funnel.

What kind of founders do you work best with?

High-agency, no-BS, ambitious operators. Founders who think fast, act fast, and crave clarity.

Do I need to be at a certain stage?

No. I've worked with people at pre-idea all the way through post-Series B. What matters is mindset, not stage.

What if I've already raised money?

Even better. There's often more chaos, politics, and urgency to cut through.

Have you worked with [insert type of startup]?

Probably. But if not, I'll get up to speed fast. My strength is pattern recognition, not narrow niche expertise.

📦 Practicalities

How do I book a call?

You can book directly here.

What happens after I book?

You'll get an email confirmation. Then a text or WhatsApp to coordinate timing. Then we talk.

Is the first call free?

No, the first call is $100. The fee is not credited toward future work—it's symbolic. It ensures you're serious and values both our time.

What is the shortest engagement possible?

We won't work together unless I know I can provide long-term impact. If I do my job, there is no ROI conversation—it's about real, lasting change, not just a quick win.

Can I cancel anytime?

Yes. No lock-ins. Just tell me before your next billing cycle.

Do you do one-off consultations?

Rarely. The real value happens over time. But I occasionally open one-off sessions.

đź§  Meta

Do you coach coaches?

Sometimes. But my sweet spot is high-intensity founders, not folks trying to sell courses.

How many clients do you take at once?

5–7 max. If I'm full, I'll tell you.

Are there case studies or testimonials?

Yes! You can read them here.

Can I talk to someone you've coached?

If it makes sense, yes. But I protect founder time. You'll get clarity on the intro call first.

What if I want to start in 3 months?

Book now. Start later. Slots don't always stay open.

Still have questions?

Contact me directly, or just book the call. That's where the good stuff happens.