The Best Job I've Ever Had with Alex Lobert

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...

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.- En...

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 go...

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 contra...

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...

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 le...

In this episode, I talk with James Hornick, the Chief Growth Officer at the executive recruiting firm Hirewell and one of the sharpest voices in the recruiting space. As an executive recruiter, James helps companies fill high-impact leadership positions (think Chief Marketing Officer & Chief Technology Officer) — giving him a front-row seat to how hiring decisions really get made. James began...

On this episode of the Show, I’m talking with someone who’s been a friend, a mentor—and at one point, my boss—Dan Gonzalez. Dan’s held marketing leadership roles at Meta, Yahoo, and now Sam’s Club. But his path wasn’t a straight line. He didn’t come out of business school gunning for tech. In fact, he thought he’d spend his career managing a retail store until a pivot to tech during the dot-com bo...

Suvo Sur is an award-winning and Emmy-nominated multi-instrumentalist and composer that has worked across film, TV, and podcasts. But it wasn't always that way. He started his career in data science with degrees in Math and Physics. To learn more about his work visit https://www.suvosur.com/

Kareem Black is an American portrait, celebrity and lifestyle photographer based in New York City. His work has been featured in Time Square over 15 times. You can see his work at https://www.kareemblack.com/

Healthcare is serious business, but does that mean it has to be boring?! The answer is definitely not if you ask Sarah Wilcox . Sarah has had an awe-inspiring career as a marketing executive focused on healthcare. A few of her notable roles include being the Vice President of Marketing at Ann & Robert H Lurie Children's hospital and the Executive Vice President of Healthcare at the advertising...

Rapper, Start-up co-founder, marketing guru… Which one would be your best job?! This is the dilemma for the crazy-talented, Pat Gibson . Pat co- founded the company, Rapchat , which gives artists - especially those in hip-hop / rap - access to a studio in their pocket and the ability to share their music with a community of creators and fans. The app garnered over $2.5 million in investment and 10...

Sometimes in your career you feel like you are a part of history. That is the case with today's guest, Lauren Legette . Lauren has worked at some of the most well known companies in the world: Facebook, Google, and Uber. She currently is the Chief of Staff for Global Marketing at Google. Lauren also founded, Black Women to Watch . Black Women to Watch is a content platform committed to amplifying...