Personal Leadership Coaching

Oliver Gillespie · Austin, TXIf you're reading this, we've probably already talked — and something in that conversation is why you're here.

About working with me

I'm not someone who has it all figured out. I'm someone who stopped pretending he did.I used to manage startups. Seven years looking like I had it all together, until it crumbled.Not the businesses. Me.I had tightened my grip on everything and everyone I thought I could control, with no idea how to lead the one person I actually needed to.Until I put myself in a room where I couldn't hide. And someone showed me what wasn't working, and handed every decision back to me. That's what I build for people now.I'll give you what I didn't have. Someone willing to get messy, name what's actually there, and stand for who you're capable of being — especially when it's hard to hear.That's the path to lasting change. And exactly what you can expect on a call with me.

What changes over 90 days

I coach you to breakthrough.Awareness, with action. The moment something becomes clear, we move on it. You choose something new and live it out within 24 hours.I don't give answers. I keep asking until the solution is actually yours. Because real transformation is never something that happens to you. It's something you choose.90 days later, you won't be finished, but you'll be leading. Your choices, your standards, your life. That's personal leadership. That's the work.And I'm in it with you, every step of the way.

What you get

  • Kickoff call

  • 12 weekly calls (1 hr each)

  • Spot coaching if needed *

  • Message support between calls

  • Session notes, plus resources customized for you

* Spot coaching — a quick call with me, whenever an urgent situation can't wait for your next session

What you invest

$2,997

For 90 Day Package

Pay in full, or in monthly installments through Affirm

People who know me

"Oliver has a distinct ability to look through me as if I were made of glass. He saw me for who I was, helped me identify emotions I had concealed for years, and supported me through them. 10/10 recommend."— Elizabeth, CEO

"Oliver embodies hard work, ownership, and commitment to change. His passion and his personal journey drive his unrelenting, tenacious approach to personal coaching and transforming lives."— Benjamin, Agency Owner

What's next?

We jump on a quick call. No pitch, no chasing you afterwards. If we are a good fit, I'll send you what you need to start.

FAQs

Do you offer payment plans? Yes. You can use Affirm at checkout to split it into monthly payments. Affirm will show you the terms and any interest before you agree to anything.Is this faith-based? I'm a Christian. It's the reason I believe you were made on purpose, by someone with an intention — and that nothing you've done has revoked that. If you don't bring up faith, neither will I. It will only show up in how seriously I take you and your journey.Is this therapy? No. I'm not a licensed therapist, and this isn't a substitute for therapy if you're dealing with something clinical. This is coaching — forward-facing work on you and how you show up. If I think you'd be better served by a therapist, I'll tell you.

(C) 2026