Why You Should Stop Chasing Money and Start Chasing Obsession, with Bill Gurley

In this episode, Kaila and Kyle discuss drug culture and how to navigate it when it interacts with your professional life. Should you talk about your weekend marijuana use with your colleagues? Is Zyn use at the office hurting your reputation? And how many drinks should you actually have at the company party? 00:00 Intro 01:23 Disclaimer 04:01 Accepted and normalized drugs 08:17 Navigating drinking culture in the workplace 15:11 Discussing marijuana at work 23:07 Zyn  29:13 Per YOUR Last Email  Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/  Watch Per My Last Email on YouTube:   @PerMYLastEmailShow Follow Per My Last Email Instagram: @permylastemailshow TikTok: @permylastemailshow Twitter: @permylast_email Have a question for us? Send us an email or voice note to [email protected] Learn more about your ad choices. Visit megaphone.fm/adchoices Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Kaila and Kyle celebrate the 100th episode of Per My Last Email with a fun and informative variety show, followed by a surprise walk down memory lane at the end. 00:00 Intro 00:32 News You Can Use 07:55 A check-in with our Gen Z correspondents  15:00 Game: Slay or Nay? 18:41 Skillcation report 23:47 Per My Last Email gets a performance review Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/  Watch Per My Last Email on YouTube:   @PerMYLastEmailShow Follow Per My Last Email Instagram: @permylastemailshow TikTok: @permylastemailshow Twitter: @permylast_email Have a question for us? Send us an email or voice note to [email protected] Learn more about your ad choices. Visit megaphone.fm/adchoices Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Kyle sits down with venture capitalist and author Bill Gurley to talk about how to figure out your passion, what people get wrong about networking, and why pursuing your dream career isn’t such an idealistic idea.  00:00 Intro 01:23 How do we recognize if we have a “passion”? 04:40 Do we spend enough time in a sampling period? 08:48 Something Bill advises young people to ask of older adults 09:14 How Bill responds to the pushback that people should aim for a stable, money-making career instead of their dream jobs 11:21 On mentorship and networking 17:09 Bill’s “Go where the action is” principle  21:54 Advice to people early in their career with regards to emerging technologies Be sure to check out Bill’s new book, Runnin’ Down a Dream: How to Thrive in a Career You Actually Love. Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/  Watch Per My Last Email on YouTube:   @PerMYLastEmailShow Follow Per My Last Email Instagram: @permylastemailshow TikTok: @permylastemailshow Twitter: @permylast_email Have a question for us? Send us an email or voice note to [email protected] Learn more about your ad choices. Visit megaphone.fm/adchoices Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Kaila and Kyle discuss their thoughts on the age-old question: is it ever okay to be emotional at work? Listen to hear their anecdotes of crying with colleagues, surface acting vs. deep acting, and why they think emotional intelligence is so crucial at this point in time.  00:00 Intro 04:26 The aim of this episode 07:27 Affective Events Theory 09:53 Primal Leadership by Daniel Goleman  14:15 Is going with your gut an example of being emotional? 17:33 The contagious effect of emotions 20:42 Crying at work 25:16 Surface acting vs. deep acting 27:42 The gender disparity when it comes to emotions in the workplace 29:57 Tactics 32:20 Per YOUR Last Email Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/  Watch Per My Last Email on YouTube:   @PerMYLastEmailShow Follow Per My Last Email Instagram: @permylastemailshow TikTok: @permylastemailshow Twitter: @permylast_email Have a question for us? Send us an email or voice note to [email protected] Learn more about your ad choices. Visit megaphone.fm/adchoices Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Kaila and Kyle revisit the topic of AI (2 years after their first episode on the topic) and discuss the major objections to AI, how the perception of the technology has changed recently, and the best ways to use it to enhance your work. 00:00 Intro 01:27 How our perceptions of AI have changed in the past 2 years 03:56 The shifting public perception of AI - efficiency vs. enhancement 12:38 First objection to AI - environmental concerns 18:13 Second objection to AI - it’s weakening our ability to think 22:08 Third objection to AI - the controversy over the way AI was trained 23:41 Use cases and tactics 31:44 The most common error Kyle sees people making with AI Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/  Watch Per My Last Email on YouTube:   @PerMYLastEmailShow Follow Per My Last Email Instagram: @permylastemailshow TikTok: @permylastemailshow Twitter: @permylast_email Have a question for us? Send us an email or voice note to [email protected] Learn more about your ad choices. Visit megaphone.fm/adchoices Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Kaila and Kyle share their predictions for work and work culture in 2026. From “job kissing” to the careers we think might be eliminated in 2026, you’re not going to want to miss this episode.  00:00 Intro 01:48 Prediction #1: Slight imperfections will be a sign of effort 06:06 Prediction #2: There will be a premium on being able to explain the business impact of your work 08:50 Prediction #3: “Job kissing” 13:06 Prediction #4: Your degree and your network will matter more than ever before 17:18 Prediction #5: The two career paths that won’t exist by 2027 23:54 Prediction #6:  Career growth is going to become a lot harder  27:12 Bonus Wackadoodle predictions 28:32 Per My Last Policy Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/  Watch Per My Last Email on YouTube:   @PerMYLastEmailShow Follow Per My Last Email Instagram: @permylastemailshow TikTok: @permylastemailshow Twitter: @permylast_email Have a question for us? Send us an email or voice note to [email protected] Learn more about your ad choices. Visit megaphone.fm/adchoices Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Kaila and Kyle discuss uncertainty at the individual, external, and societal level, and share their best strategies for managing and coping with the anxiety that comes with it.  00:00 Intro 03:08 Addressing uncertainty on the individual level 08:57 Kyle’s bucketing approach for tackling uncertainty 15:23 Dealing with external, corporate-level uncertainty 22:28 Discussing uncertainty at the societal level Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/  Watch Per My Last Email on YouTube:   @PerMYLastEmailShow Follow Per My Last Email Instagram: @permylastemailshow TikTok: @permylastemailshow Twitter: @permylast_email Have a question for us? Send us an email or voice note to [email protected] Learn more about your ad choices. Visit megaphone.fm/adchoices Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this special bonus episode, Kaila and Kyle sit down with Industrious president Anna Squires Levine to discuss the role that connection plays at work, the future of offices and hybrid vs. remote work, the role of leadership in the modern workplace, and advice on making career pivots. 00:00 Intro 01:16 University of Chicago Booth School of Business study on human connection 07:45 What most companies get wrong about how to design a great working environment 10:31 Advice for companies trying to introduce more fun into their culture  12:42 How should leaders think about creating a great workplace given the mixture of hybrid, remote, and in-office employees? 15:57 Game: Ask Anna 22:43 How Anna approaches building a culture of energy (vs. one of burnout) 25:37 Anna’s advice for those looking to make a career pivot 29:47 What parenting has taught Anna about navigating work This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour.  Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/  Watch Per My Last Email on YouTube:   @PerMYLastEmailShow Follow Per My Last Email Instagram: @permylastemailshow TikTok: @permylastemailshow Twitter: @permylast_email Have a question for us? Send us an email or voice note to [email protected] Learn more about your ad choices. Visit megaphone.fm/adchoices Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Kaila and Kyle get into personal finance—the money lessons they learned the hard way throughout their careers, and how they approach managing their savings, investments, and spending now. 00:00 Intro 02:36 A big wake-up call money moment in Kaila’s life 07:27 Kyle’s big wake-up call money moment 10:21 Kaila’s experience with lifestyle creep 13:56 An important salary negotiation in Kyle’s career  18:10 Learning to how to spend based on your values 21:40 Structuring your compensation 25:18 How Kaila and Kyle structure their savings and personal finances This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour.  Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/  Watch Per My Last Email on YouTube:   @PerMYLastEmailShow Follow Per My Last Email Instagram: @permylastemailshow TikTok: @permylastemailshow Twitter: @permylast_email Have a question for us? Send us an email or voice note to [email protected] Learn more about your ad choices. Visit megaphone.fm/adchoices Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Kaila and Kyle share the productivity tips that help them accomplish their to-do list, and to get your 2026 off to a strong start.  00:00 Intro 02:20 Kaila’s and Kyle’s word of the year 04:30 Productivity tip #1: The Sunday Setup 09:29 Productivity tip #2: The Bullet Journal 13:06 Productivity tip #3: Commit to S*** 16:57 Productivity tip #4: Lean into the Eustress Curve 19:09 Productivity tip #5: Time Block the Bull**** 22:20 Productivity tip #6: Create Boundaries Around Your Energy 25:18 Productivity tip #7: The Great Filter 26:03 Bonus listener question This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour.  Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/  Watch Per My Last Email on YouTube:   @PerMYLastEmailShow Follow Per My Last Email Instagram: @permylastemailshow TikTok: @permylastemailshow Twitter: @permylast_email Have a question for us? Send us an email or voice note to [email protected] Learn more about your ad choices. Visit megaphone.fm/adchoices Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app! Learn more about your ad choices. Visit megaphone.fm/adchoices