[Author Series] How To Handle Conflict Like a Pro With Gabe Karp

Gabe Karp is a bestselling author, keynote speaker, and conflict management expert known for his book Don’t Get Mad at Penguins: And Other Ways to Detox the Conflict in Your Life and Business. He began his career as a trial lawyer, later becoming Executive Vice President and General Counsel at ePrize (now Merkle), where he helped grow the company into a global leader in digital promotions.

Currently, Gabe serves as an Operating Partner at Detroit Venture Partners and a Venture Partner at Lightbank, advising early-stage tech companies and serving on multiple boards. His work focuses on transforming conflict from a liability into a strategic asset, drawing from over 30 years of experience in law, business, and venture capital.

Here’s a glimpse of what you’ll learn:

• [5:27] Gabe Karp discusses why he wrote Don’t Get Mad at Penguins
• [9:00] Tools for managing ego-driven conflict with zero cost
• [11:37] How Gabe’s need to win almost sabotaged a client’s case
• [15:48] A behind-the-scenes story of a judge who changed the outcome of a trial
• [19:18] The bully trap and how passion can turn into destructive behavior
• [24:18] How Navy SEAL-style debriefs can transform company culture
• [28:46] Tips for embedding conflict resolution practices into everyday business meetings
• [32:37] Calling out a hospital CEO in front of 50 staff members
• [38:35] Teaching young professionals to challenge authority through mock deception
• [42:22] Handling the difficult task of firing someone you genuinely like
• [50:55] The penguin analogy of managing expectations to reduce frustration and conflict

In this episode…

Navigating conflict is one of the biggest challenges in both personal and professional relationships. Whether dealing with strong personalities, avoiding uncomfortable conversations, or managing unspoken resentment, unresolved conflict can slow progress, damage culture, and erode trust. So, how can leaders turn conflict into a tool for growth instead of a source of frustration?

Gabe Karp, conflict management expert and author of Don’t Get Mad at Penguins, shares a framework for transforming toxic conflict into a productive force. Drawing on his experiences as a former trial lawyer, executive, and venture capitalist, he explains how leaders can shift team dynamics by normalizing direct communication, embracing discomfort, and identifying common conflict traps such as ego, the need to win, and misaligned expectations. Gabe introduces strategies like the debrief/pre-brief meeting format, ego-neutral negotiation, and fostering cultures of candor and accountability, all of which help teams surface issues before they escalate.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz interviews Gabe Karp, Operating Partner at Detroit Venture Partners, about building healthier team dynamics through conflict. Gabe discusses how to dismantle ego-driven tension, the power of cultural feedback loops, and why expectations shape most of our frustrations. He also explores lessons from litigation, handling difficult terminations, and creating space for honest team dialogue.

Resources mentioned in this episode:

• Gabe Karp on LinkedIn | Website
• Don’t Get Mad at Penguins: And Other Ways to Detox the Conflict in Your Life and Business by Gabe Karp
• “How To Thrive With Difficult People” by Gabe Karp

Special Mention(s):

• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship by Ben Horowitz
• The Wisdom of Teams: Creating the High-Performance Organization by Jon R. Katzenbach and Douglas K. Smith
• The Paradox of Excellence: How Great Performance Can Kill Your Business by David Mosby and Michael Weissman
• 80/20 Sales and Marketing: The Definitive Guide to Working Less and Making More by Perry Marshall
• Essentialism: The Disciplined Pursuit of Less by Greg McKeown
• Rocket Fuel: The One Essential Combination That Will Get You More of What You Want from Your Business by Gino Wickman and Mark C. Winters
• The Miracle Morning: The Not-So-Obvious Secret Guaranteed to Transform Your Life (Before 8AM) by Hal Elrod
• Stand Out: How to Find Your Breakthrough Idea and Build a Following Around It by Dorie Clark
• Disciplined Dreaming: A Proven System to Drive Breakthrough Creativity by Josh Linkner
• Big Little Breakthroughs: How Small, Everyday Innovations Drive Oversized Results by Josh Linkner
• The A-B-C of the isms: And other exposes by Dan Gilbert
• Evolution: The root of all isms by Dan Gilbert

Related episode(s):

• “[Top Author Series] Does God Exist? with Perry Marshall author of Evolution 2.0” on the Inspired Insider Podcast
• “[Top Author Series] The Essentialism Movement with Greg McKeown Author of “Essentialism” & Founder of ThisInc.co” on the Inspired Insider Podcast
• “[Top Author Series] The Two Leadership Traits To Explode Your Business With Mark C. Winters Author Founder of RocketFuelNow.com” on the Inspired Insider Podcast
• “Leading with Passion with Gino Wickman Founder of EOS Worldwide” on the Inspired Insider Podcast
• “[Top Author Series – Inspiration] Hal Elrod: TWO rock bottoms.” on the Inspired Insider Podcast
• “[Top Author Series] How to Create Your Breakthrough Idea with Dorie Clark, Author of “Stand Out”” on the Inspired Insider Podcast
• “[One Question] Exploring Innovation with Josh Linkner Founder of Platypus Labs” on the Inspired Insider Podcast

Quotable Moments:

• “Catering to your own ego is very costly, but catering to someone else’s ego is free.”
• “My need to win the trial eclipsed the whole goal of why I needed to win.”
• “If you do not speak in this section of the meeting, you are not doing your job.”
• “You’re never going to lose your job for making a mistake. You could lose your job for covering up a mistake.”
• “So much conflict and so much angst and frustration people feel because their expectation is different from the reality.”

Action Steps:

1. Embed debrief meetings into your workflow: Regularly discussing what went right or wrong encourages transparency and surfaces issues before they escalate.
2. Normalize calling out issues in real time: Creating a culture where speaking up is expected keeps communication honest and reduces unresolved resentment.
3. Feed others’ egos when needed: Acknowledging someone’s need to feel respected dissolves tension and opens the door to cooperation.
4. Accept people’s limitations to reduce frustration: Matching your expectations to reality helps preserve emotional energy and avoid repeated conflict.
5. Separate performance feedback from personal judgment: Critiquing behavior rather than character fosters trust while supporting meaningful growth.

Episode Transcript

Intro: 00:00

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz: 00:22

Dr. Jeremy Weisz here founder of InspiredInsider.com where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Gabe Karp. You can check out everything he’s doing at gabekarp.com.

And Gabe, before I formally introduce you, I always like to point out other episodes of the podcast people should check out. Since this is part of the Top Author series, I share some. You know, I love having my favorite authors on here and Gabe has an amazing book, Don’t Get Mad at Penguins, which we’ll talk about I listen to on audible. It’s fantastic, and some of my other favorites. And Gabe off to hear some of your favorites too.

Perry Marshall was on. He talked about the 80/20 Sales and Marketing. I had Greg McEwan on who wrote Essentialism. Mark Winters and Gino Wickman wrote Rocket Fuel, which is a good one. Hal Elrod wrote Miracle Morning, Dorie Clark Stand Out and then the list would be complete without Josh Linkner.

Of course, I know you know Josh well and he was on the podcast. He talked about, you know, he wrote many books, two of which, Disciplined Dreaming and Big Little Breakthroughs. Gabe, do you have some favorite books? Obviously. Besides, Don’t Get Mad at Penguins.

What are some of your favorites?

Gabe Karp: 01:33

I do The Hard Thing About Hard Things. It was Ben Horowitz, I can’t remember. It was Ben Horowitz or Marc Andreessen.

Dr. Jeremy Weisz: 01:41

Ben Horowitz, yeah.

Gabe Karp: 01:42

Yeah, Ben Horowitz, that’s a great one. There’s one called The Wisdom of Teams. I cannot remember who wrote it, but I thought that was insightful. And there’s a short book called The Paradox of Excellence that I thought was also very good. I mean, that’s off the top of my head, I wasn’t yeah.

Dr. Jeremy Weisz: 02:04

No Wisdom of Teams. I’m looking it up here. It looks like John Katzenbach and Douglas Smith. Does that ring a bell?

Gabe Karp: 02:13

Yeah, that sounds right okay.

Dr. Jeremy Weisz: 02:15

Yeah. The Wisdom of Teams. Cool. No, thanks for sharing. All I have for audible credits.

So that’s going to help. So I appreciate that. But check those out. More on inspiredinsider.com. This episode is brought to you by Rise25 and Rise25.

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I’m super excited to introduce Gabe Karp. Gabe Karp is don’t hold this against him. A former litigator turned startup executive turned venture capitalist, Gabe actually had a front row seat to toxic conflicts of others. He built and led successful teams and negotiated business and finance deals in the hundreds of millions of dollars. He’s got over 30 years of experience on how to detox.

The inevitable conflicts that come up and an interesting journey took an unexpected turn in the startup world as executive VP and general counsel of E-Prize, which got acquired now Merkel and they grew that company from a scrappy startup into a global leader. They work with 75 of the world’s top 100 brands. We have a small world connection, good friends with Marty Madden, who’s a leadership performance coach, and his wife, Lindsay has worked for E-Prize and for many years. And so. But Gabe has led multiple acquisitions, secured major financing deals, even personally oversaw more than 13,000 interactive promotions across 44 countries.

Now he’s you know, in addition, we talked about, you know, he’s the author of Don’t Get Mad at Penguins: And Other Ways to Detox the Conflict in Your Life in Business. But he’s also an operating partner at Detroit Venture Partners and a venture partner at Lightbank in Chicago, where they help early-stage tech companies. So Gabe, thanks for joining me.

Gabe Karp: 05:01

All right. Thank you. Great to be here. Thanks for having me.

Dr. Jeremy Weisz: 05:04

We’ll start off I mean, there’s so many questions and thoughts I have on this, but I’m going to pull up. There’ll be a video I’m going to pull up Gabe’s site in a second. But what inspired you to write the book? First of all, Don’t Get Mad at Penguins. I mean, you’re a busy guy.

I mean, I listed a bunch of things in, you know, you have no lack of things to do.

Gabe Karp: 05:27

Yeah, well, you know, it’s interesting throughout, at various points of my career, particularly when I was in the when we were growing the startup, I would look back six months, a year and just inventory how I was spending my time. And in the IT, what I found is that I was, regardless of the details of whatever logistic thing I was working on, I was always gravitating toward conflict and as a trial lawyer, as a litigator, of course, I was creating conflict, making it worse. As an executive in a technology company, I was routed, seeking out conflict, rooting it out and then fixing it so we could move along and go faster. So I found I just found that the people around me were very uncomfortable with conflict. I came from the litigation world, so I was very comfortable with it.

I, in fact enjoyed getting into conflict, and I wasn’t aware about how uncomfortable people were, and my lack of awareness made them even more uncomfortable. By the way, if you hit the home button, that’s well, yeah, let’s get mad at Penguins the. So I really enjoyed working with people and solving those problems so we could just move faster Master, and we could make more money and we could increase profit margins and we could grow the careers of the people we were working with more, and we could resolve our differences without drama. And in working with people and seeing how uncomfortable they were with it. I had the conscious thought of, I have to make these people more comfortable with conflict.

We cannot afford the drag on our progress because of this discomfort. And I just started coming up with really simple, easy-to-use tools that anyone could use to sort of navigate difficult situations. And I found that people would come back to me weeks and months later and saying, hey, I just want to let you know, like that. We were talking a while back, you said this one thing and it just really resonated. And I use it all the time now and it’s and it’s great.

So that was the impetus for really focusing on how to make conflict work for us, not against us. And I started doing some keynote speaking, and the first keynote speech I really formulated became the outline of the book. So that’s a very long answer to why did I decide to write a book? I decided to write it because I love conflict. I had an outline for it.

I never thought of myself as an author, but once I realized I had something to say and I had a good framework to say it, I said, all right, let’s sit down and get to brass tacks and start writing this. And by the way, Covid had just hit, so I had a lot more time on my hands.

Dr. Jeremy Weisz: 08:23

I love to hear some of those tools and exercises. I do want to point out up there. You do have a great Ted talk here. So if you go to where I engage, if you’re listening to the audio or GabeKarp.com, if you scroll down, there’s a watch TedTalk link here. And it’s a great again Cliff Notes version of your book.

So I encourage people to check it out. listen to this, and then obviously get the actual book which has everything in it. But what are some of your, you know, the fan favorite tools or exercises?

Gabe Karp: 09:00

There are some good ones. I think one of the good tools is you deal with people with ego a lot. You know, I look as a lawyer and you deal with other lawyers. That’s it’s sometimes hard to fit inside a room because the egos are so big. And I, I, I’m certainly as guilty of that as anybody, particularly earlier in my career.

And I would find that when I would deal with other lawyers and their, and my ego and their ego were bumping up against each other, it just after a while, it just got annoying to me because it because and I annoy, by the way, I annoyed myself. It’s like, why am I dealing with this? And I came up with the really simple statement of catering to your own ego is very costly. But catering to someone else’s ego is free. So if you find that you’re dealing with someone who’s ego is driving that conflict, I say feed that person’s ego.

It’ll literally cost you nothing. And you just recognize that this person has a need to feel powerful. So just tell them they’re powerful and like respectfully ask. Do not use their power to hurt you. And once you do that, every time I’ve done that, I have found that the other person immediately changes for the positive instead of us butting heads.

I’ve checked off a mental box in their mind, they may not even be consciously aware that they had. They just have. They have that need to be seen as somebody who’s, you know, should be respected and is powerful and is smart. And once you just give that to them, they’ll be very willing to give you whatever it is you want. I mean, now you’re going to some negotiation if it’s a financial deal, but it just makes moving through that process so much easier.

Dr. Jeremy Weisz: 10:49

Yeah. And there’s a great story. If you go to, you know, get his book. There’s a great like real-world story that he tells in the book about how he actually did this when there was this conference call with a group of lawyers. So, you know, look, you know what I’m talking about.

Yeah. That’s a good story in the book. There’s another one. I’m curious. The take-home point.

There’s another one of my favorite stories of the book where I don’t know if it’s really define as ego, but you let your goal-driven ego get away from you. And you had a stern talking to their or he got a stern talking to. Talk about that for a second. And it kind of talks about having the actual goal in mind.

Gabe Karp: 11:37

Yeah this was I now I now know what you’re talking about. There’s a chapter called The Judgment Trap that the book kind of breaks down very common toxic traps that repeat over and over again different names, different dates, different facts, same pattern. Years ago, I was a pretty young lawyer and I had a client who was driving down the road minding her own business. And as she’s turning a corner, a huge one of those huge like city buses, county buses swerves into her lane and it was far ahead of her. So the back end of the bus banged into the front driver’s side of her car and didn’t do a lot of damage on impact, but it forced her off the road.

She crashed right into a telephone pole, and had a horrible. She was disabled as a result of this single mother of three. This dramatically changed her life for the worse. It was bad. And the bus, by the way, just kept going.

Didn’t even stop. And the. The bus company denied that the accident even happened. And I am trying to help her out. They hired one of the biggest law firms in town.

They were throwing all kinds of money at it. And basically I was just outgunned and I knew it. I mean, they had more money, more resources, more time than I had. And all I had was just the word of my client. That was it.

But one day I’m poring through this like mountain of thousands of documents they threw at me in discovery. And I find the smoking gun. It was the log sheet from the bus that day, written in the bus driver’s own handwriting. And if you’ve ever seen anger like, translated into the written word, this was it. At the top of the page.

I remember it said this was supposed to be my day off. The guy wrote it in all caps, three exclamation points, underlined it, and then at the on one corner it said this is an overloaded route with too many rowdy passengers. And then it said per dispatch, pedal to the metal, back to station. And that entry was written six minutes before the accident happened, and the log sheet proved that the boss was in the exact location of the accident at the exact time my client says it happened. So I’m like, this is it.

I’m like, I’m going to win. And I didn’t even tell the other side about it. I didn’t even say I found it. I don’t think the lawyer on the other side even knew this thing existed, because they were just mailing it in at the at the bus driver’s deposition, he just said, I don’t even remember that day. And I didn’t have the log sheet when I had his debt.

But clearly he remembered that day. This guy was pissed off. There was no question about it. So fast forward, we show up for trial, and the judge pulls both lawyers into her chambers like any good judge does, and tries to hold a settlement conference. Like, is there any chance we can settle this before we start picking a jury?

And at some point during the settlement conference, she separates. It talks to us separately. And when she gets me alone, she proceeds to tell me that I have a weak case. And like, she can’t understand why I didn’t accept their settlement offer. So I took a chance.

I tipped my hand. I showed the judge, I said, judge, I want to show you something. You got to promise you’re not going to show the other side. Because they don’t know about it. And I showed her the log sheet and I explained my whole theory of the case.

And she’s like, all right, I got it. And then she calls the other lawyer back in and she says, you got to increase your offer. And the other lawyer says, Your Honor, I don’t believe this action even happened. What do you mean, increase my offer? And the judge said, well, I believe it happened, and I believe he is going to convince a jury that it happened.

And I don’t want to waste two weeks of my courtroom on a trial that should settle. And then she just proceeds to lean on this lawyer. Like, I’ve never seen anyone lean on lawyer before. And at one point, she picked up the phone and she said, do you need me to call your client and get more authority for you? And I got to pause here because.

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