The Best Job I've Ever Had with Alex Lobert

Alex Lobert
  • 5.0 (1)
  • Entrepreneurship

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.

  1. Sep 14

    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

  2. Aug 4

    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.

  3. May 7

    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

  4. Mar 6

    This History Major Now Invests in Space Lasers (Yes, Really) | Ben Spacapan

    In this conversation, Ben Spacapan delves into the world of private equity, sharing insights on the decision-making process involved in investing in businesses. He emphasizes the importance of building long-term partnerships and the joy of engaging in meaningful discussions about business ownership and collaboration.Takeaways:- The essence of private equity lies in thoughtful decision-making.- Engaging in deep discussions about business ownership is crucial.- Building long-term partnerships is key to success in business.- Objective evaluations help in choosing the right companies to invest in.- The joy of the job comes from meaningful interactions and learning.- Understanding company culture is vital for successful partnerships.- Private equity offers opportunities for collaborative growth.- Investing is not just about money; it's about relationships.- Learning from businesses informs better investment decisions.- The role of private equity is to help businesses thrive.Ben Spacapan Links: * Madison Dearborn Team: https://www.mdcp.com/team/ben-spacapan* LinkedIn: https://www.linkedin.com/in/benjamin-spacapan/

  5. Jan 28

    Harvard PhD to Policy Powerhouse: Jenny Gordon on Reforming Government, Managing Crisis, and Careers

    Dr. Jenny Gordon is a Harvard-trained economist and one of Australia’s most influential policy leaders.In this episode, we go inside the real work of reform—from aged care and early childhood policy to rebuilding Indonesia’s debt system after a financial crisis.Jenny shares what it actually takes to make big changes happen: how evidence meets politics, how to build coalitions, and how to keep going when the incentives aren’t aligned. If you’re curious about impact, public service, economics, or just how the world really works behind the scenes—this one’s for you.In this episode, we cover:- What it’s like being a chief economist inside government- How major reforms (like aged care + early childhood) get designed and passed- The behind-the-scenes reality of crisis response and rebuilding financial systems- How to influence decision-makers when “good ideas” aren’t enough- Career lessons from a life spanning academia, government, and policy leadershipGuest: Dr. Jenny Gordon: https://www.lowyinstitute.org/jenny-gordon

  6. 05/28/2025

    Trust the Fish: Carlos Cabrera’s $500K Bet on Seafood Tech

    Carlos Cabrera, EVP @ Wild Alaskan Company, swapped breaking news for building tech that ships wild-caught seafood to U.S. doorsteps. Carlos's Career Journey: • Passed on a safe consulting offer to chase documentary journalism. • Cold-emailed a fellow Northwestern Wildcat, joined a media startup Storyhunter (now called Glimmer), and fell into product management. • Quit a comfy PM role, went contractor-mode, and helped launch Wild Alaskan Company. Show Links: Carlos' LinkedIn: https://www.linkedin.com/in/%F0%9F%90%9F%F0%9F%91%8D-carlos-cabrera-9b40b813/ Wild Alaskan Company: https://wildalaskancompany.com/

    Trust the Fish: Carlos Cabrera’s $500K Bet on Seafood Tech

  7. 05/08/2025

    Curiosity, Tenacity, Hustle: Lessons from Peter Szabo's journey from radio to tech & music exec

    I talk with music and tech executive Peter Szabo. Peter has had a front-row seat to the transformation of the music industry. Peter Szabo started at KISS 108, an iconic Boston radio station, during the internet's earliest days. His job was to post pictures and videos of bands like Backstreet Boys, Jay-Z, and Dave Matthews Band. Without knowing it, Peter was at the forefront of shaping how we’d all soon connect with music online. From there, he stepped into leadership roles at companies that completely changed the music landscape: Pandora, Shazam, and Spotify. And now with his own company, “The Idea Factory,” he is helping artists and brands harness the power of authentic partnerships. Like the ones where the artist actually enjoys the product – From the Struts to Train. But beyond his impressive resume, Peter brings deep insights about the human side of success—how curiosity and tenacity drive innovation, why great leaders prioritize kindness, and how a single generous act from a boss can leave a lifelong impact, especially during a crisis. Links: Peter Szabo’s LinkedIn: https://www.linkedin.com/in/pszabo/ The Idea Factory: https://www.ideafactory.solutions/

    Curiosity, Tenacity, Hustle: Lessons from Peter Szabo's journey from radio to tech & music exec

  8. 04/29/2025

    Job Shaping, Entrepreneurship & Imposter Syndrome w/ Jessica Hutson, Little Torch Leadership

    In this episode, I talk with Jessica Hudson, an expert in learning and development who has built successful programs at Facebook and TikTok. Now running her own business, Little Torch Leadership, Jessica helps startups and executives enhance their effectiveness. She shares the importance of job shaping, dealing with imposter syndrome, and strategic career transitions. Whether you're an aspiring leader or an entrepreneur, Jessica's practical advice and inspiring stories are sure to resonate. Jessica's LinkedIn: https://www.linkedin.com/in/jessicahutson/ Little Torch Leadership: https://littletorchleadership.com/

    Job Shaping, Entrepreneurship & Imposter Syndrome w/ Jessica Hutson, Little Torch Leadership
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About

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.

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