280. Ross Pomerantz: From pro baseball to Corporate Bro, the BTS of navigating his career identity, making over $100K on LinkedIn, Super Bowl commercial with Matthew McConaughey, and beyond
Trading Secrets
Audioboom Studios
4.9 • 5.8K Ratings
🗓️ 23 February 2026
⏱️ 85 minutes
🧾️ Download transcript
Summary
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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Transcript
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| 0:42.2 | Welcome back to another episode of Trading Secrets. Today we're joined by the hilarious corporate bro and Ross Pomerates. |
| 0:47.7 | They're actually two different personalities under one home. |
| 0:51.4 | We'll talk all about it. |
| 0:52.8 | Someone who's lived in the high pressure, high performance |
| 0:55.2 | world of corporate finance and selling at Oracle and actually has the scars and stories to |
| 1:01.0 | prove it. Ross brings a real, unfiltered, hilarious perspective on what enterprise sales |
| 1:06.2 | really looks like behind the scenes. From ambition and burnout to the funny tradeoffs, nobody talks about unless you're deep in it. He's covering it all. In this episode, we get into the psychology of how sales sucked turned into a massive empire. He's a speaker, investor, entrepreneur, and massive creator. Ross, let's get into him. That's good to have you on sharing secrets. I'm honored to be here. Welcome to my city. Let's go. It's good to be in your city. |
| 1:29.7 | So you called, I mean, you are born and raised in Atlanta, right? I moved when I was 13. Okay. So, you know, I'm still a Braves fan. Okay. I was a baseball player. You know, that was my, still play baseball but you know sort of adopted the warriors when they were terrible and the |
| 1:43.1 | niners when they were fine like i just i was always a baseball guy in alana so it's i've just stayed |
| 1:47.5 | true to that. And then |
| 1:48.4 | I guess now I'm a bandwagon fan, so everyone want to call me. Jealous. You know, as a Bill's guy, I'm jealous of that. Well, you'll like this story, actually, when the Braves won the World Series, It was in Houston. |
| 1:57.6 | And we got tickets through the Braves team somehow, |
| 2:01.7 | and we were able to sneak into their after party. |
| 2:04.6 | Oh. in Houston. And we got tickets through the Braves team somehow. And we were able to sneak into their after party. So we were at the after party with the Braves, with the World Series, party in our ass off. My cousins from Atlanta was like the best. God, that was great. That would be like if the Bill's won super rule and I snuck into that. So anyway, I had to put that out there. Wow. Well, I'm jealous. |
| 2:17.9 | Well, that actually connects to where I want to start with you. |
... |
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