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Welcome back to Insider Pix, where we uncover what entertainment and culture insiders are watching, reading, and listening to! Next up:
Jessica Geran Straw
Jessica Geran Straw is the Director of the Executive-in-Residence (EIR) Program at Progress Partners, an investment bank and venture group focused on the technology sector, with a foundation in Media, AdTech, and MarTech. With a background in venture capital and operating experience, Jessica also advises growing companies on strategy and investor readiness.
Jessica’s 5 Picks
A hidden gem you wish more people knew about?
I’m Sorry. I’m a huge comedy fan, and I watched this at a time in my life that felt pretty parallel to the show. There are scenes that still make me laugh just thinking about them. It’s painfully relatable in the best way.
Best TV show you’ve watched recently?
Shrinking. It’s the perfect combination of funny and deep. It captures how messy life is and how flawed we all are, but ultimately, how much the people in our lives make the hard parts more bearable and the good parts that much better.
A 5-star-worthy book you’d recommend to anyone?
I’d actually tweak the question to “any adult.” This summer, I was talking with a highly respected colleague turned friend about how I think classic literature is wasted on high school and college students. You’re asked to appreciate these books before you’ve had much real-world experience, all while juggling schoolwork and the pressure to perform.
We both decided to revisit authors we’d hated as young adults. I chose Steinbeck and dove into The Grapes of Wrath. It hits hard. The themes transcend time, and I finally understand why it’s considered one of the great American novels. I just don’t think I could have appreciated it as a teenager.
Best movie you’ve watched recently?
Ha! I’m a mom of three elementary school-aged boys, so my recent movie viewing has been limited to their preferred cartoon genre. Of those, I’d pick GOAT. As for movies I’d choose for my own enjoyment, someday I’ll have both the time and the ability to stay awake again.
Go-to weekly podcast?
Pivot to keep up with the news and Wiser Than Me for some entertaining wisdom. One keeps me informed; the other gives me perspective - everyone’s life takes unexpected turns, and there’s something to learn from how people navigate them.
Pix: You're a big believer in the power of connection. What's one networking tip you swear by that more people should know about?
JGS: Human first. Business follows. The best professional relationships grow out of genuine human connection, not a transaction.
Pix: If you had $1 million to invest in any fictional character's business venture, who would get your check?
JGS: I’d invest in Rebecca Welton’s AFC Richmond from Ted Lasso.
Sports are hot right now, across men’s and women’s leagues and teams, and it’s a fun space to be in. Professional sports offer multiple revenue streams, from media rights and sponsorships to ticketing, merchandise, and global fan engagement.
But with AFC Richmond, I’d be betting on the community around the team as much as the team itself. A strong culture gives fans a reason to stay invested and creates opportunities for the brand beyond the field.
And it would be so fun to root for!
Pix: As a self-proclaimed “Brainstormaniac,” what's your secret to a truly productive brainstorming session?
JGS: Everything is on the table. You never know when a completely illogical, out-there idea will spark the right one. Create a space where people feel safe enough to say the thing that might sound ridiculous, and resist the urge to shoot ideas down too early. You can edit later. First, give creativity some room to work.