Craig Hewitt on How AI Magnifies Your Leadership
Click on the photo to watch full episode on YouTube
What does it actually look like to transform a real, running business into an AI-native company — not in theory, but in practice?
In this episode, Olivia sits down with Craig Hewitt — CEO and founder of Castos, fractional head of AI, and CEO coach — to talk about what he learned rebuilding his own seven-figure SaaS company from the inside out, and how he now helps other CEOs do the same.
Craig documented the entire journey publicly through his 100 Days of AI series on YouTube. What started as a content experiment became a playbook. Now he works with CEOs of $3M–$30M businesses to help them move from dabbling to actually leading an AI transformation.
Whether you're a founder, a CEO, or an employee trying to figure out where to start, this conversation will change how you think about what's possible right now.
What we cover:
The moment Craig decided to go all-in on AI, and why he saw it coming
What it actually means to be AI-native vs. just using AI
Why most CEOs stay stuck in dabbling, and how to get out
What has to die in a leader's identity for real transformation to happen
How Craig rebuilt Castos leaner with AI, and the human cost honestly
Why everyone is becoming a leader now whether they're ready or not
Who owns the agents: the organization or the individual?
What to do right now if you're a CEO, and what to do if you're an employee
Why Craig's team celebrated spending $5K in a month on AI tokens
Connect with Craig Hewitt
He coaches CEOs through AI transformation, drops weekly insights for business leaders in his newsletter, and documents everything on YouTube.
Website & Coaching: https://craighewitt.com YouTube: https://www.youtube.com/channel/UCY0w_qU4qO5MgHpEkpRLocg Twitter/X: https://x.com/thecraighewitt LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66 Instagram: https://www.instagram.com/thecraighewitt Podcast: Rogue Startups
He also created a series called 100 Days of AI, where he made a video every day for 100 days straight, all about AI: https://www.youtube.com/playlist?list=PLNhO4I3x7BeZcq8WnekCRYg44UPDs5KJu
Watch our full interview here: