What makes a great job? In this podcast, host Alex Lobert talks with a diverse set of people to explore the highlights from their careers.
On each episode, we dive into what are people's best job and why. What people say is their best job may surprise you... It's not all about money and prestige.
Join us for great stories and honest discussion about the highs - and occasionally the challenges - of people's careers.
Joe Martin: Why the Best Jobs Let You “Do More Weird”
Everybody knows B2B marketing can get boring. Joe Martin is just more willing than most to say it.Joe is the marketing lead at PostHog, one of the most distinctive brands in tech. He joined when the company was roughly 10 people and has been there as it grew to around 200 — while somehow keeping much of the autonomy, weirdness, and hands-on energy that made the job fun in the first place.In this episode of The Best Job I’ve Ever Had, Joe and I talk about why PostHog deliberately avoids a lot of traditional B2B marketing, what it means to have “Do More Weird” as an actual company value, and why PostHog dedicates roughly $45,000 every month to ideas that often have no direct ROI attached to them.We also get into Joe’s path from games journalism to corporate marketing to startups, the boss who told him he had become toxic at a job he hated, why finding the right working environment matters so much, and his advice for anyone looking for their own best job: lean into the influences and experiences that make you different.Along the way: art exhibitions, Mr. Blobby, hedgehog soapbox derbies, a possible PostHog telecom company, and the idea that sometimes measuring everything is exactly how you kill a good idea.Find Joe + PostHog:https://linkedin.com/in/joemartinwordshttps://posthog.com/https://posthog.com/merchhttps://posthog.com/handbookThe Best Job I’ve Ever Had explores the jobs people genuinely love — how they found them, what makes the work great, and what the rest of us can learn from their paths.#PostHog #Marketing #Careers #B2BMarketing #Startups
4 Aug 2026
After 15 Years in Tech, The Product Marketer Built His Best Job
After 15 years across Amazon, Google, YouTube, and European startups, Rory Woodbridge bet on himself—and says he’s now the least stressed he has been in more than a decade.Rory is the founder of The Product Marketer, a consultancy and newsletter helping product marketers do better work. In this episode of The Best Job I’ve Ever Had, we explore how an unexpected move into product marketing became a career, why finding his voice meant becoming more opinionated, and what changed when he finally went solo.We discuss:• What product marketing actually is—and why it remains so mysterious• Lessons Rory learned at Google, YouTube, and fast-growing startups• How consistent, opinionated writing helped him reach nearly 6,000 subscribers• Why European product marketing needs its own approach• How AI could eliminate busywork and make marketers more strategic• Why the best job for you will change throughout your life• What it takes to build a career around your energy, strengths, and prioritiesIf you’re considering going solo, building an audience, or creating a career with more autonomy, Rory’s story offers an honest look at what it takes.Follow Rory Woodbridge:The Product Marketer: https://productmarketer.substack.com/LinkedIn: https://www.linkedin.com/in/rorywoodbridge/Subscribe for more honest conversations about the choices, turning points, and lessons behind people’s best jobs.
7 May 2026
The Entrepreneur's Entrepreneur: Nick Tippman of TipTop VC
Nick Tippmann has spent his career building — as a founder, marketer, CMO, and now venture capitalist at TipTop Ventures. But when asked about the best job he’s ever had, he points to his time helping build Greenlight Guru, a mission-driven software company serving medical device companies.In this episode, Nick shares why the best work often comes from a rare combination: doing hard things, with people you trust, in service of a mission that matters. He talks about dropping out of college to teach himself startups and venture capital, joining Greenlight Guru as an early employee, growing into the CMO role, building a high-retention culture, and eventually making the leap into venture capital.We also get into what entrepreneurship really requires, why grit matters more than most people think, how to find the right people to build with, and why Nick believes the future of software is vertical.Links: Nick's LinkedIn: https://www.linkedin.com/in/nicktippmann/TipTop VC: https://www.tiptop.vc/The Best Job I've Ever Had: bestjobever.org
Who has been a guest on The Best Job I've Ever Had with Alex Lobert
Names identified in recent episode analyses. Showing up to five guests.
Carlos Cabrera
Peter Szabo
Jessica Hutson
James Hornick
Dan Gonzalez
Reach and audience
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Apple Podcasts (US)
5.0 / 5
1 ratings
Spotify
4.9 / 5
14 ratings
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