Podcast Summary: Help Wanted

Episode: "Your Colleague Is Being a Jerk... Should You Tell Them?"

Release Date: March 24, 2026
Hosts: Jason Feifer (Entrepreneur Editor in Chief), Nicole Lapin (Money Expert)

Episode Overview

In this engaging and candid episode, Jason Feifer and Nicole Lapin dive into a common workplace dilemma: When a colleague acts like a jerk, do you tell them? Jason brings a real-life scenario involving a professional slight, and together, they unspool the emotional and strategic responses to workplace jerkiness. Listeners are guided through options ranging from confrontation to gracious maneuvering, all laced with the hosts’ characteristic humor and honesty.

Key Discussion Points & Insights

1. The Real-Life Scenario: “Steve” the Expert (05:23–11:30)

• Jason’s Dilemma: Jason recounts his frustrating interaction with "Steve", an expert he invited to appear on his less popular podcast. Steve’s assistant tried to angle for a more prominent guest spot upon realizing Jason’s other show, Help Wanted, had a bigger audience.

  “It's like, oh, hey, thanks for being willing to promote my book. Actually, could you promote it somewhere else? That’s better. I don't really like the thing that you've offered me. Are you kidding? This is the very definition of looking a gift horse in the mouth…” – Jason Feifer [07:02]

• Escalation: After Jason grudgingly contributed a guest post for Steve’s newsletter, Steve published it as a premium (paywalled) post, limiting Jason’s exposure.

  “He did not send this out to his whole audience. He actually made it a premium post, which means...only a small portion of what I wrote is available to his large audience, and then they have to pay him to read the rest of my work. And I saw this yesterday, and I was outraged.” – Jason Feifer [09:38]

2. To Tell or Not to Tell – Emotional vs. Strategic Responses (11:30–15:14)

• Nicole’s Framework: Three Choices

  1. Say Nothing: Vent to your friends, but don't confront the person.
  2. Confront: Tell them off directly (“boo boo head/jerk/whatever”).
  3. Friendly Inquiry/”Fake Nice”: A strategic, professional follow-up asking when the promised wider exposure will occur.

  “Generally we don't know why someone did something...all this stuff in our head...we actually don’t know...If you want to know what someone's thinking, you must ask them.” – Nicole Lapin [12:38]

• Assume Positive Intent: Nicole suggests that approaching the situation factually may produce results or, at the very least, preserve professionalism.

3. Defining the Goal (15:14–17:14)

• What Do You Want to Achieve?: Nicole emphasizes the importance of knowing one’s end goal before acting. Is it revenge, professional value, or closure?

  “We're solving for X. You already know the answer...There was a thing that happened. 2 plus X equals 4. We are solving now for X. And we already know the answer and we're fine with it. And all of those roads will probably lead to that. So which road potentially gets you more of a thing?” – Nicole Lapin [15:30]

• Regrets About Confrontation: Nicole shares personal experience, lamenting direct confrontations in the past.

  “I always regretted it 100% of the time. Life is long, the world is small. Don’t be an asshole is my motto. It does not get you anything, Jason, by telling fucking Steve O.” – Nicole Lapin [16:25]

4. The “Investment” Analogy and Extracting Unexpected Value (17:14–23:18)

• Jason’s Philosophy: He likens time (and favors) to investment. Not every investment will pay off, and it’s best to accept losses and focus on possible gains.

  “If we think of time as a resource...you take 10% of [your time], divide it up into investments, knowing that a whole bunch...are going to be busts...maybe some of those investments is spending a little bit of time writing a guest newsletter for a guy who was already kind of a dick…” – Jason Feifer [18:22]

• Nicole’s Addition: Even “failed” efforts can yield unexpected value, such as stories for personal or professional platforms.

  “You’re getting value in unexpected ways. We’re making a show about it...so content is your least favorite word beast, right? And so collecting these stories and collecting these experiences is actually valuable to you.” – Nicole Lapin [21:13]

• Storytelling as Value: Stories from difficult experiences can benefit others, teaching lessons or informing teams even without direct payoff.

5. How to Handle Future “Steves” (23:18–26:52)

• Spirit vs. Letter of the Deal: Nicole advocates for sticking to the spirit of agreements and maintaining upstanding business practices, even amidst disappointments.

  “Contracts get violated a lot because they're the letter of the law. But the spirit of a deal, I think, is actually much more important. And that’s where the relationship hinges.” – Nicole Lapin [24:18]

• Sample Message to “Steve”: Nicole and Jason brainstorm a diplomatic follow-up that reinforces expectations, expresses hope for wider exposure, remains fact-based, and leaves the “door open” for Steve to do right.

  “Hey, I saw this thing came out. Wish I would have had a heads up...As we talked about, was hoping this would go out to the entire list. Maybe that was an error or an admin error…Would still love to get exposure to the whole audience.” – Nicole Lapin [25:16]

6. Episode Takeaways – The “Poo Poo Platter” Summary (26:02–26:52)

• Rules for Jerk Encounters:

  1. Never just tell someone they’re a “poo poo head.”
  2. Always fun to vent to friends.
  3. Sometimes, treat the “poo poo head” like they’re not—and see what happens.

  “The summary here is: Rules. Number one, never just tell someone they're a poo poo head. Number two, always fun to tell your friends that someone was a poo poo head. And number three, sometimes treat the poo poo head like they're not a poo poo head and see what happens.” – Jason Feifer [26:24]

Memorable Quotes & Moments

• “I want a podcast with nicer numbers. Fuck you.”
  – Nicole Lapin, on Steve’s attitude towards podcast size [07:43]

• “If you want to know what someone’s thinking, you must ask them.”
  – Nicole Lapin [12:38]

• “Life is long, the world is small. Don’t be an asshole is my motto.”
  – Nicole Lapin [16:31]

• “Time is your most valuable resource and therefore you should kind of spend it the way that you think about spending money...”
  – Jason Feifer [18:22]

• “So I think it honors just your general vibe of upstanding business practices. ...there are a lot of people professionally who will play in traffic for you and you do the same for them.”
  – Nicole Lapin [24:43]

Timestamps for Key Segments

• 05:23 – Jason’s story: the “Steve” situation unfolds
• 11:55 – Nicole’s three-pronged response framework
• 15:30 – Defining what you want from a confrontation
• 16:25 – Nicole’s regrets about calling people out
• 18:22 – The time-as-investment analogy
• 21:13 – Extracting value through storytelling
• 24:18 – The spirit vs. the letter of the deal
• 25:16 – Nicole models a diplomatic follow-up message
• 26:24 – The “poo poo platter” summary

Final Takeaways

• Recognize the personal and professional costs and benefits before confronting a colleague over “jerk” behavior.
• Venting to friends is valuable; directly confronting rarely yields career value.
• Approach suspected slights with curiosity and professionalism—it may yield better outcomes or, at the very least, maintain dignity.
• Even negative work experiences can become a resource, either as content or as learning for yourself or others.
• Above all: Don't let a “Steve” derail your mood, professionalism, or long-game strategy.