Jim Olson has spent his career helping businesses navigate moments of intense pressure from corporate crises to deeply personal challenges, running comms at United Airlines and Starbucks. In this episode, the author of Tailwind shares the lessons he’s learned from leadership, resilience, and facing adversity head-on.

Drawing inspiration from Captain Sully’s Hudson River landing, Jim explains why the best crisis leaders follow the same process: aviate, navigate, communicate. We discuss where crisis management often goes wrong, what leaders can learn from failures like United Airlines, and why “black box thinking” matters in both business and marketing.

Jim also opens up about his own cancer diagnosis and the mindset that helped him through it.

Get Jim's new book, Tailwind here:
https://www.amazon.com/Tailwind-Compass-Turning-Setback-Comeback/dp/B0GXCM3VYT/

00:00 - Start
01:11 - Lessons from Captain Sully’s Hudson River landing
06:11 - The black box thinking approach to marketing
07:30 - Other crises Jim has had to deal with in his career
09:18 - When crisis management goes wrong - United Airlines
13:11 - Managing merging two cultures
15:27 - The situation when Jim’s CEO had a heart attack
18:00 - Jim’s cancer diagnosis
23:30 - The power of positive mentality
28:30 - Don’t ask yourself what if, ask yourself why not
31:34 - The power of a fourth space
34:05 - Crisis doesn’t build character, it reveals it
37:02 - Leadership lessons from Howard Schultz
38:58 - Jim’s advice for those people facing a crisis

Dan Taylor has spent over two decades at Google, helping shape how brands grow through search, media, and technology. Today, he leads global advertising at one of the world’s most influential companies, giving him a front-row seat to the biggest shifts in marketing.

In this episode, Dan shares what he’s learned from 20 years at Google, from the importance of simplicity to navigating organisational complexity and the evolving relationship between product and commercial teams. We also dive into the future of search, including AI, new tools like “Circle to Search,” and what it all means for marketers.

Timestamps

00:00 – Start
00:40 – Lessons from being a pilot
05:34 – Lessons from 20 years at Google
06:43 – How Google has changed over two decades
07:46 – The power of simplicity
09:02 – Google’s breakthrough moments
12:11 – The relationship between commercial and product
13:47 – Navigating organisational politics
17:08 – The biggest search trends in marketing
18:24 – What is “Circle to Search”?
20:37 – Opportunities for marketers in new search behaviours
24:52 – How AI is changing search
25:59 – Does Google see AI as competition?
28:09 – Will ads exist in AI search?
32:00 – How brands can improve search performance
33:42 – Making the most of Google and YouTube
35:34 – Measuring the value of brand search
39:56 – AI’s impact on creativity
45:52 – The one lesson from 20 years at Google

Zena Arnold, CMO of Sephora, joins us to break down how one of the world’s most influential beauty retailers continues to set the standard for brand, community, and culture.

From standout branding to record-breaking product launches, Zena shares what’s behind Sephora’s success and how the business stays relentlessly close to its customers in a fast-moving category. We explore the rise of celebrity brands, the power of loyalty, and how Sephora works with creators through initiatives like the Sephora Squad.

Thank you to our sponsor, System1: https://system1group.com/

Timestamps

00:00 - Start
01:13 - Zena’s incredible marketing career
06:02 - Lessons that turned Zena into the marketer she is today
07:41 - What has made Sephora so successful?
10:01 - Why Sephora’s branding stands out
11:30 - What’s trending in the beauty category in 2026?
13:22 - How does Sephora stay close to the customer?
14:45 - The biggest brand launch in Sephora history
15:25 - How to pitch a beauty brand to Sephora
18:00 - How important are celebrity brands?
19:03 - Helping brands launch in Sephora
21:00 - The power of Sephora’s loyalty programme
25:09 - How Sephora attract new customers
27:02 - How Sephora uses creators effectively with the Sephora Squad
29:45 - How to measure the effectiveness of creators
31:12 - The exceptional advertising of Sephora
32:49 - How Sephora uses tech in their marketing
38:09 - Dealing with the speed of retail
39:00 - Creating conditions where you can fail and learn