Terry and Sidney O’Reilly talk about big names who faced big rejection on ‘We Regret To Inform You’

September 1, 2021

If you remember Dax’s pick from the 5th episode, he raved about “We Regret To Inform You: The Rejection Podcast.” He and Alesha have since become hooked, and they were lucky enough to be joined by the creators and host themselves: Sidney and Terry O’Reilly.

But first, Dax has another suggestion. This week, he has been binging “The Dropout,” a podcast about the infamous Elizabeth Holmes and her company Theranos. The podcast tells the story of the former business woman who was called “the next Steve Jobs,” whom Dax explains Holmes was obsessed with. She started to dress like him (black turtleneck, you know the look) and even changed her voice to try to sound like him. Anyway, “The Dropout” is a true crime tale of the downfall of the woman who said she was revolutionizing healthcare.

Also, the new season, “The Dropout: Elizabeth Holmes on Trial” just dropped on Tuesday, August 31st and will take us inside the courtroom to find out how this wild saga finally ends.

Next up are the newest Podsauce guests: Sidney O’Reilly and Terry O’Reilly. Dax and Alesha cannot get enough of this podcast – just talking about her admiration for these stories has Alesha in tears. An actor herself, she deeply relates to the stories that are shared every season. The O’Reilly’s describe the conception of “We Regret To Inform You: The Rejection Podcast” and the research they do to create each episode. The conversation between the four jumps between the rejection they’ve faced themselves and the episodes that their own stories remind them of.

The guests then share the podcasts that they are currently obsessing over. For Sidney, she recommends “Where Should We Begin?” a podcast from therapist Esther Perel that Sidney says is like being a fly-on-the-wall of a couples therapy session. She also recommends “Alone Together,” a podcast about loneliness: explaining habits of loneliness and how we as humans combat it.

Terry suggests “Against The Rules,” hosted by author Michael Lewis of Moneyball, which looks at subject matters from different points of view, like the life of a referee. Also, “The Score: Bank Robber Diaries” in which an actual bank robber, who robbed 30 banks, talks about how he did it.

Alesha’s pick/the Murder Most Foul (because, of course) podcast of the week is “Affirmative Murder,” hosted by Alvin Williams and Francel Evans. “Affirmative Murder” is, as Alesha puts it, the Black perspective on true crime. They two hosts swap murder stories from marginalized communities all while putting a comedic twist on it.

That is it for this week’s Podsauce, see below for links to all of the podcasts mentioned this episode. Ciao!


Alesha’s Pick

Affirmative Murder

Listen to ‘Affirmative Murder’

Dax’s Pick

The Dropout

The Dropout podcast art
Listen to ‘The Dropout’

Sidney and Terry O’Reilly’s Picks

Where Should We Begin? with Esther Perel

Listen to ‘Where Should We Begin? with Esther Perel’

How’s Work? with Esther Perel

Listen to ‘How’s Work? with Esther Perel’

Alone Together

Listen to ‘Alone Together’

Against The Rules with Michael Lewis

Listen to ‘Against The Rules with Michael Lewis’

The Score: Bank Robber Diaries

Listen to ‘The Score: Bank Robber Diaries’

What we're listening to this week...

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