We're Here to Help – Episode 236: ROCKET MONEY BEST ADVICE EPISODE 4

Host: Headgum
Guests: Steve Berg (special guest), callers Max, Talia ("Tally"), Mikey, Anna, Kelsey, Kyle
Release Date: December 3, 2025

Episode Overview

This “Best Advice” installment features Jake Johnson and Gareth Reynolds joined by actor Steve Berg. The trio takes calls from listeners who each share the greatest piece of advice they've ever received. Amid irreverent riffing, impressions, and endearingly chaotic humor, the group mines genuine wisdom and celebrates the quirks of friendship, the weirdness of growing up, and the little things that help us get by—including, unavoidably, the show’s sponsor, Rocket Money.

Key Conversations & Advice Highlights

1. Birthday Antics & Impressions with Steve Berg (00:47–08:10)

• Kicking Off with Chaos: Steve Berg opens by “singing” Happy Birthday, blending joy with bits of stand-up riffing. The guys roast each other about attention-loving, their energy, and general podcasting mayhem.
• Childhood Bits: Steve reflects on why he's always been popular with moms: “They got the keys to the kitchen, baby.” (02:41)
• A Parade of Impressions: Caller Max steals the show by performing spot-on impressions of Eric Edelstein, Steve Berg, Gareth, and Jake—much to everyone’s delight (05:09–06:47).

Memorable Quote:
“Do you want to know why Steve Berg has always been so warm to moms growing up?... They got the keys to the kitchen, baby.” – Steve Berg (02:29–02:41)

2. Best Advice Calls

a. Knowing When to Shut Up – Max’s Story (08:16–11:51)

• Context: Max shares a lesson from his early wine sales career, involving a disastrous dinner where he argued with his boss. Afterward, a friendly mentor gave him this gem:
  • Quote: “Arnold Palmer once said, sometimes what’s more important than knowing what to say is knowing when to shut the fuck up.” (10:10)
• Hosts' Reflection: Jake and Gareth agree, noting this is wisdom “you learn way more as you get older.” (10:42–11:02)
• Sidebar: The conversation derails briefly into jokes about Arnold Palmer, LBJ, and “big hogs” in presidential lore.

Notable Moment:
Jake calls it “such good advice, especially for young people.” (10:42)

b. “Just Call Me Tally” – Navigating Name Mistakes (Talia from Cincinnati, 13:30–20:01)

• Situation: Talia’s neighbor Jeff has called her “Tayla” for years. Embarrassed to correct him after so long, a friend advises: just say, “All my friends call me Tally.”
• Quote: “That way he knows I’m his friend. And he calls me Tally now and still offers me weed every day.” (18:02)
• Hosts Share: Gareth talks about using a friend’s fake ID and transitioning names at the bar—a relatable bit about identity and rolling with social awkwardness.
• Lighthearted Side: Much laughter about the neighborly excess of homegrown zucchini and weed.

c. If You Think It’s Funny, Don’t Do It – Mikey from Brooklyn (24:29–26:58)

• Story: Mikey recalls his dad’s favorite warning after years of childhood mischief:
  • Quote: “If you think it’s funny, don’t do it.” (24:50)
• Reflection: Jake reframes it as, “If you think the mean joke is worth it, think again. Or make sure you know who you’re delivering it to.” (25:53)
• Discussion: They commiserate on growing up as “attention-seeking little shits,” learning humor’s limits, and the times jokes have landed poorly.

d. Shit or Get Off the Pot – Anna from Washington (33:27–37:34)

• Advice: Anna’s dad’s blunt guidance during a driving lesson:
  • Quote: “You either have to shit or get off the pot.” (35:07)
• Application: The crew agrees it’s perfect not only for driving but also for decision-making in life, creativity, and collaborative ventures.

e. Always Consult Children (for Surprising Wisdom) – Kelsey from Connecticut (42:23–46:55)

• Story: As a middle school special education teacher, Kelsey asked her students for advice for her sister. A child responded: “She needs to get a Slinky…it’ll take her mind off things.” (43:45)
• Lesson: “Always consult children. Even though they don’t have life experience, they weirdly get life, remind us to have fun and find the good in all moments.” (45:33)

f. Give More Compliments – Kyle from Oregon (52:03–59:24)

• Setup: Kyle’s wife teaches his reserved family a lesson during a vacation by adding a new rule to their game night: instead of paying to the pot, you can give another player a compliment.
• Quote: “My mom audibly said, ‘Oh, fuck.’... We’re not a very affectionate bunch. We’re emotionally repressed…” (55:19, 56:04)
• Impact: The forced affection leads to “20 minutes of everyone giving compliments,” sparking sweet introspection and warmth.
• Group Compliments: The hosts and Kyle then go around giving each other heartfelt compliments, ending the segment on a genuine high note.

Notable Quotes & Moments

• “If you think it’s funny, don’t do it.” – Mikey’s Dad (24:50)
• “Sometimes what’s more important than knowing what to say is knowing when to shut the fuck up.” – Max’s Mentor (10:10)
• “You either have to shit or get off the pot.” – Anna’s Dad (35:07)
• “Always consult children…they weirdly get life.” – Kelsey (45:33)
• “Give more compliments.” – Kyle’s wife (53:30)
• “They got the keys to the kitchen, baby.” – Steve Berg (02:41)

Memorable Bit:
Steve’s comic riff about why he loved moms growing up, just hanging around for adult snacks, is a show highlight.

Running Gags, Inside Jokes, and Recurring Themes

• Steve's Compliments: Listeners are invited to take a shot every time Steve compliments something or someone—be it a city, a vegetable, or a caller. (“Oh, I love zucchini!” – 16:17)
• Host Dynamics: Jake’s grumbly pragmatism, Gareth’s lightning-fast wit, and Steve’s bottomless positivity create a recipe for both genuine advice and comedic chaos.
• Impression Olympics: Max’s impressions delight the crew and set a playful tone for the advice segments.
• Eric at the Vet: Prolonged running jokes about Eric Edelstein “being at the vet” (“He’s getting neutered…”) add to the episode’s absurdist humor. (13:51)
• Plugging Rocket Money: They weave Rocket Money references throughout, ultimately framing “saving money” as the single best advice, with mock-gravitas.

Listener Takeaways

While the advice veers from the profound (“know when to shut up”) to the practical (“correct a name mistake with a friendly nickname”), the episode’s throughline is how seemingly simple advice can change perspective, ease awkwardness, or open hearts. Amid digressions, jokes about presidential “hogs,” and slinky therapy, the hosts always circle back to the genuine purpose: finding help and humor in the mess of modern life.

Timestamps for Key Segments

• 00:47–03:27: Birthday song & mom’s kitchen keys story
• 05:09–06:47: Caller Max’s impressions
• 08:16–11:51: Arnold Palmer advice: “Know when to shut the fuck up”
• 13:30–20:01: Talia’s story: “All my friends call me Tally”
• 24:29–26:58: Mikey’s story: “If you think it’s funny, don’t do it”
• 33:27–37:34: Anna’s driving lesson: “Shit or get off the pot”
• 42:23–46:55: Kelsey’s story: “Always consult children”
• 52:03–59:24: Kyle’s advice: “Give more compliments”; hosts exchange compliments
• 60:44–68:18: Reflections, gratitude, and closing banter

Final Thoughts

Jake Johnson (61:00):
“There’s a purity, but also just one of the funniest people on planet Earth…”
(on Steve Berg, after the round of compliments ends in classic chaos)

Steve Berg (62:47):
“I would love items very refined palette at a young age, especially for tomato based products…what a perfect way to end a Thanksgiving episode. This is what we’re grateful for.”

The episode concludes with a (tongue-in-cheek) plea to lift the show’s own “ban” on discussing a friend’s Dick Van Dyke-related project and one last heartfelt thanks to Rocket Money—for providing structure to the chaos and, as Gareth puts it, possibly the best advice of all: “save your money.”