164 How to Build Billion-Dollar Startups | Osman Rashid, Founder, Chegg & Convo.com

Thursday 12th March 2026

Quotes

“This is a great podcast for those who want to be on a constant learning adventure”
- iTunes Reviewer

“The only podcast I listen to. I don’t have time to listen to podcasts, but I make the time to listen to this one”
- iTunes Reviewer

“So, so good!!! By far my favorite podcast – really enjoy the straightforward, no BS conversations”
- iTunes Reviewer

“#1 Podcast for a reason”
- iTunes Reviewer

“This is not your average self help podcast”
- iTunes Reviewer

“Honesty and passion”
- iTunes Reviewer

“Quite frankly, unlike any other podcast”
- iTunes Reviewer

"Real conversations with no bullshit - the guests get driven away from their standard form responses, and irreverence is valued"
- Podcast Listener

"I listen during my commute. I feel like I learn something new every conversation and I feel energized and empowered to tackle the small and big challenges. "
- Podcast Listener

"There is an authenticity to Christopher's approach that I respect, in addition to the breadth of the subject matter. Also a huge fan of his 2 books. "
- Podcast Listener

"The people that “get it” today are doing things in an authentic manner. They realize that no one wants the over produced glitzy BS and instead they just want to learn. I listen to this podcast because it cuts through the noise and provides incredible insight on how to build a legendary company / career - and it’s coming from folks that have done it, not just talked about it. "
- Podcast Listener

"Good people, good conversations, fun and insightful"
- Podcast Listener

"I love Christopher and TOTALLY relate to how his heart and brain work - just like mine! - and I feel a greater invitation to be more ME - as I am-take it or leave it. Every single guest arrives authentic and beyond inspiring and OMG I LAUGH LAUGH LAUGH! I keep buying all their books! Love you Christopher and love that you share your REAL YOU with all of us and invite us all to do the same!"
- Podcast Listener

"I like being exposed to people and thoughts that I wouldn’t normally get to listen and learn from in the general day to day of life and business”
- Podcast Listener

"It is like being a fly on the wall in a high level conversation and there are great insights from people with proven legendary results "
- Podcast Listener

“Christopher Lochhead is the Joe Rogan of Business”
- Jon Bergoff, CEO, Flourishing Leadership Institute

"Off-putting to some"
- The Economist

"Christopher Lochhead is a human exclamation point"
- Fast Company Magazine

"Christopher Lochhead is one of the best minds in marketing"
- The Marketing Journal

“Christopher Lochhead is an exploding star – a quasar across the sky."
- Bill Walton, NBA Hall of Fame Legend

Latest Episodes

425 The Category Creation Formula: Why Most Business Strategy is a Trap with Kevin Maney & Mike Damphousse

424 AI Agent & Copilot Podcast: Christopher Lochhead on Creator Capitalists and the Future of Work

423 Military Creator Con: Celebrating Military Creators & Entrepreneurs with James Van Prooyen and Marah Lago

422 The Transformation Economy with Joe Pine, World-wide Bestselling Author of “The Experience Economy”

421 Davos Update, What do Earnings From, Apple, Meta, Tesla & Microsoft Mean For You, and the Future of AI, Ray Wang Feb 2026

420 How to Flourish with Daniel Coyle, NYT Best-selling Author of The Culture Code, on new book “Flourish: The Art of Building Meaning, Joy, and Fulfillment”

Listen via these channels

164 How to Build Billion-Dollar Startups | Osman Rashid, Founder, Chegg & Convo.com

Quotes

Sponsored by:

Latest Episodes

425 The Category Creation Formula: Why Most Business Strategy is a Trap with Kevin Maney & Mike Damphousse

424 AI Agent & Copilot Podcast: Christopher Lochhead on Creator Capitalists and the Future of Work

423 Military Creator Con: Celebrating Military Creators & Entrepreneurs with James Van Prooyen and Marah Lago

422 The Transformation Economy with Joe Pine, World-wide Bestselling Author of “The Experience Economy”

421 Davos Update, What do Earnings From, Apple, Meta, Tesla & Microsoft Mean For You, and the Future of AI, Ray Wang Feb 2026

420 How to Flourish with Daniel Coyle, NYT Best-selling Author of The Culture Code, on new book “Flourish: The Art of Building Meaning, Joy, and Fulfillment”

Listen via these channels

GET EMAILS FROM THE CATEGORY PIRATES

Navigation

About

Podcast

Blog

Books

Contact Us

Listen

Latest Episodes

425 The Category Creation Formula: Why Most Business Strategy is a Trap with Kevin Maney & Mike Damphousse

424 AI Agent & Copilot Podcast: Christopher Lochhead on Creator Capitalists and the Future of Work

423 Military Creator Con: Celebrating Military Creators & Entrepreneurs with James Van Prooyen and Marah Lago

422 The Transformation Economy with Joe Pine, World-wide Bestselling Author of “The Experience Economy”

421 Davos Update, What do Earnings From, Apple, Meta, Tesla & Microsoft Mean For You, and the Future of AI, Ray Wang Feb 2026