In the fall of 2016, I received an email from my agent: Another client they represented noticed I had a new book coming out and wanted to invite me on his show. The request came from Jude Angelini, the host of the All Out Show on Shade 45, Eminem’s SiriusXM hip-hop station. But unlike most requests I get, this one came with a warning: “I’m not sure if you’re interested in going on a show like this. I listened briefly to one interview, and it’s pretty racy, to say the least.”
Now, I don’t shy away from much, so I was sure she was just being overly cautious. I googled “Jude Angelini” and…she was not exaggerating. Jude is what is politely referred to as “colorful”; he tends to ruffle feathers. His style and manner reminded me of old school Howard Stern, and I quickly learned he first made his name roasting people on the Jenny Jones show. (He was REALLY good at it.)
I reconsidered her warning. Was he going to roast me on his show? Did I really want to subject myself to that?
For reasons I can’t explain, I decided to do it.
From the moment I entered the studio, Jude and I clicked. We were the unlikeliest duo — opposites in so many respects, and yet, so incredibly similar in ways those daunting internet clips might not have predicted. That All Out Show appearance was the start of a great friendship (and one I would’ve missed out on, had I not followed my underdog principles of taking calculated risks and leaning into life). Now, nearly 8 years later, my life is richer for saying “yes” to Jude and calling him my friend.
So when I decided to focus on underdogs as the first Sociology of…Everything theme, I knew Jude was the perfect person to tap as my guest. Not only is he one of my favorite underdogs, but there are few people I love analyzing life with as much as him. We can disagree (and we do, often), but we make each other consider a topic from a new perspective, and I can always count on him to join me in finding the funny side of life.
WHY YOU SHOULD WATCH: In this conversation, Jude and I discuss all things underdog: We explore the experience of feeling like an outsider, the benefits of framing oneself as an underdog, and the importance of courage, grit, and resilience. We also discuss the role of creativity and improvisation, as well as the challenges of paying attention and why more people don’t take calculated risks. We analyze gratitude, social media, romanticizing hardship, persevering, rejecting imposter syndrome, bucking assumptions, and finding humor in the struggle.
We close with the 3 questions I’ll ask every guest:
What’s your favorite thing to observe and what has it taught you?
What’s your underdog anthem? (Yes, we play them)
And (most importantly) which karaoke duet would we sing together? (Yes, we sing them)
[If you’ve been thinking: Is any of her stuff actually gonna be worth my $5? I hope this is the moment you answer YES and watch the video.]
What you’ll see / hear:
[Warning! We use adult language in this video.]
00:00 Introduction (and disclaimer)
00:57 Meet Jude
02:30 Jude's forever-underdog status
04:19 Do more people feel like outsiders than ever before?
08:55 Once an underdog, always an underdog? + The underdog advantage
10:26 Grit: the defining ingredient
13:20 Negativity/victimhood vs being an underdog
14:18 Jude’s surprising underdog role model
15:30 Cultivating courage
16:15 The science behind underdog framing
18:30 What do people misunderstand about being an underdog?
22:28 Fighting complacency
26:15 Improvising life
28:00 Why you’re probably not paying attention and why you should
32:23 Finding the funny in life
35:45 The value of taking calculated risks
40:25 Become a “Yes” person (even if you have kids!)
43:40 Worrying about being liked will hold you back (focus on this instead)
46:20 Social Media: Underdog manufacturer or saboteur?
52:50 Saying “No” to imposter syndrome
58:30 The struggle is real + overcoming assumptions
01:00:35 Our favorite underdog anthems
01:03:01 Jude’s current favorite thing to observe
01:06:54 The power of karaoke (+ that time Jude crashed Anna’s karaoke party)
01:10:01 The Jude + Anna duet
Find / support Jude: Buy Jude’s books, join his Patreon, follow him on Instagram.
Enjoy the conversation, leave us your comments, and don’t forget to submit your underdog-related questions, which I’ll answer next week. (And share the video with your friends!)
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