Tackling the Optionality Trap with Iann Karamali episode artwork

EPISODE · May 11, 2026 · 1H 3M

Tackling the Optionality Trap with Iann Karamali

from The Path That Makes Us · host Will Holbrow, Ari Levine

In this episode, Iann Karamali traces an unlikely path: from helping his family get Monarch Liquor off the ground during undergrad to consulting at Deloitte to exploring the future of AI through entrepreneurship. He gets into what early reps as a small business owner taught him about operating a business, why growing up inside an entrepreneurial family gives you an instinct for opportunity that's hard to replicate in a classroom, and what it looks like to run something as a fresh college graduate. He also talks about what his time in consulting added to the way he thinks about business, how he used Kellogg as a launch pad rather than a safety net, and his candid take on where AI is headed and what it means for small business owners trying to keep up.Chapters00:00 Introduction to Ian Karamali 00:29 Background and the One-Year MBA Program 04:02 Growing Up First-Gen and the Optionality Trap 08:25 Navigating the Prestige Treadmill 12:11 Founding Monarch Liquor in East Austin 16:04 Betting on Delivery and Surviving COVID 21:22 What Entrepreneurship Actually Teaches You 27:44 Joining Deloitte and Early Client Lessons 35:22 Becoming an AI Lead at the Firm 37:22 Why Kellogg, Why Now 42:15 Entrepreneurship at Kellogg and the Levy AI Track 50:23 Being a Dad in Business School 58:51 The Future of AI: Two Frameworks 01:05:51 Lightning Round

In this episode, Iann Karamali traces an unlikely path: from helping his family get Monarch Liquor off the ground during undergrad to consulting at Deloitte to exploring the future of AI through entrepreneurship. He gets into what early reps as a small business owner taught him about operating a business, why growing up inside an entrepreneurial family gives you an instinct for opportunity that's hard to replicate in a classroom, and what it looks like to run something as a fresh college graduate. He also talks about what his time in consulting added to the way he thinks about business, how he used Kellogg as a launch pad rather than a safety net, and his candid take on where AI is headed and what it means for small business owners trying to keep up.Chapters00:00 Introduction to Ian Karamali 00:29 Background and the One-Year MBA Program 04:02 Growing Up First-Gen and the Optionality Trap 08:25 Navigating the Prestige Treadmill 12:11 Founding Monarch Liquor in East Austin 16:04 Betting on Delivery and Surviving COVID 21:22 What Entrepreneurship Actually Teaches You 27:44 Joining Deloitte and Early Client Lessons 35:22 Becoming an AI Lead at the Firm 37:22 Why Kellogg, Why Now 42:15 Entrepreneurship at Kellogg and the Levy AI Track 50:23 Being a Dad in Business School 58:51 The Future of AI: Two Frameworks 01:05:51 Lightning Round

NOW PLAYING

Tackling the Optionality Trap with Iann Karamali

0:00 1:03:55

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

Frequently Asked Questions

How long is this episode of The Path That Makes Us?

This episode is 1 hour and 3 minutes long.

When was this The Path That Makes Us episode published?

This episode was published on May 11, 2026.

What is this episode about?

In this episode, Iann Karamali traces an unlikely path: from helping his family get Monarch Liquor off the ground during undergrad to consulting at Deloitte to exploring the future of AI through entrepreneurship. He gets into what early reps as a...

Can I download this The Path That Makes Us episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.
URL copied to clipboard!