This week, Jason is joined by the hilarious Corporate Bro, Ross Pomerantz!
He is someone who has lived in the high pressure, high performance world of corporate fiance and selling at Oracle and actually has the scars and stories to prove it. Ross brings a real unfiltered hilarious perspective in what enterprise sales really looks like behind the scenes. From ambition and burnout to the funny trade-offs nobody talks about unless you’re deep in it, he is covering it all. He is a speaker, investor, entrepreneur, and massive creator.
Ross breaks down everything from playing two seasons of Single-A pro baseball to selling luxury apartments in Oakland during Occupy Wall Street, and the identity shift from athlete to enterprise sales at Oracle. He shares what it was like training to cold call, navigating an identity crisis, and clarifying that “Corporate Bro” was always meant to satirize the industry — not glorify it — after getting his start on Vine in 2013. We dive into spending a decade in sales before business school, negotiating lessons, trusting timing, and earning admission to Stanford, along with the fear of fully committing to content creation and how he scripts and produces highly shareable videos with his team. He also talks about appearing in a Super Bowl commercial alongside Matthew McConaughey for Salesforce, leveraging opportunities on LinkedIn, his speaking business, co-hosting a podcast with Corporate Natalie, angel investing, building alongside his wife, and what’s next.
Ross reveals all this and so much more in another episode you can’t afford to miss!
Host: Jason Tartick
Co-Host: David Arduin
Audio: John Gurney
Guest: Corporate Bro Ross Pomerantz
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