In this episode, Josh Oliver joins the show for a candid conversation about leadership, entrepreneurship, and building companies with intention rather than ego.

Josh shares his journey through startups, acquisitions, and high-growth environments, offering honest reflections on what it takes to scale responsibly while staying grounded. He speaks openly about decision-making, learning through failure, and why clarity of values matters more than speed when building something that lasts.

Throughout the conversation, Josh emphasizes the importance of self-awareness, surrounding yourself with the right people, and resisting the pressure to chase every opportunity. His perspective offers a practical and human look at leadership in environments where momentum, risk, and ambition collide.

This episode is especially valuable for founders, operators, and leaders navigating growth without losing alignment.

⏱ Timestamps

00:00 — Welcome and episode intro

00:49 — Introducing Josh Oliver

01:38 — Early career path and entrepreneurship

03:21 — Learning through building and selling companies

05:04 — Leadership lessons from growth stages

07:12 — Decision-making under pressure

09:44 — Knowing when to say no

12:16 — The cost of chasing everything

14:05 — Building teams you trust

16:37 — Ego, humility, and leadership maturity

18:58 — Learning from failure

21:31 — Values-based leadership

24:09 — Staying grounded as momentum grows

26:47 — Advice for founders and operators

29:14 — Final reflections and close

📣 CALL TO ACTION

If this episode resonated with you:

👍 Like the video

💬 Comment with your biggest takeaway

🔔 Subscribe for more leadership and founder conversations

📤 Share this episode with someone building something meaningful