First Person Coaching
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.Then I got into a room where I couldn't hide. From there, someone showed me what wasn't working, stood with me while I chose, and ran with me while I changed. That's what I build for people now.I'll give you what I needed — someone willing to get messy, name what's really 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 it's what you can expect on every call with me.
What you can expect
I'm not here to help you inch forward. I'm here so you will choose to be unrecognizable.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 happening to you, it's something you choose.Six months 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 the fire with you, every step along the way.
What's included
Kickoff strategy call
24 coaching calls (1 hr each)
Spot coaching as 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
$8,000
For 6 Month Package
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 personal journey drive his unrelenting, tenacious approach to personal coaching and transforming lives."— Benjamin, Agency Owner
How to get started
We jump on a call. 45 minutes. No pitch, no chasing you afterwards. If we're a good fit, I'll send you what you need to start. That's it.
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 pay.Is this faith-based? I'm a Christian. I believe you were created on purpose, to know love and to live free, no matter what you've done. If you don't bring up faith, then 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.