How I Smuggled A Puppy Past TSA - The Ray J. Green Show

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How I Smuggled A Puppy Past TSA

Most people think sales is a role. It’s not—it’s a constant condition. This episode reframes sales as the ability to navigate other people’s motivations under real constraints, using a story that exposes how decisions actually get made in everyday life.

What You’ll Learn in This Episode:

  • Why “I’m not in sales” is a costly assumption
  • How decisions are shaped by context, emotion, and timing—not logic alone
  • What changes when you start seeing alignment instead of persuasion

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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

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YouTube | LinkedIn | Facebook | Twitter | Instagram

Transcript

Sales is the most underrated life skill on the planet, and I’m going to prove it to you with the story of how I sold my way past TSA with an eight-week-old puppy just a couple days before Christmas.

And here’s what happened: This past December, my wife and I decided we’re going to get our boys a dog, a puppy for Christmas. She wanted a dog, the boys wanted a dog, they’d been asking for months, they finally wore me down. And the deal was, I get to pick the dog. For two reasons: one, it was three against one and if I was going to get anything out of this negotiation it was going to be I pick the dog. The other thing is, my wife picked the last dog and we love him, but he’s bonkers. So this round is on me. And I grew up with German Shepherds most of my life—big dogs, guard dogs, family guard dogs, large dogs, right?

So a good friend of mine has a couple Rhodesian Ridgebacks that we love. So we said, you know what, that’s what we’re doing. So I picked; I said we’re going Rhodesian Ridgeback. And my buddy helped me find a breeder in Missouri. We live in Cabo, so a few days before Christmas, I fly up to pick him up. This is where it gets kind of interesting because at eight weeks, this Rhodesian Ridgeback is already too big for the largest carry-on that TSA approved. So they’ll let you carry on up to a certain size and as long as the dog can stand up with space and turn around—they’ve got like a test, basically. So as long as they’ve got space within this little container, they’re good to go.

But at eight weeks, we got the biggest container we could get to do carry-on, and he could fit in the bag, right? Like it wasn’t... he didn’t have room to stand up all the way and he wasn’t going to pass their turnaround test and all that shit. But he was going to fly comfortably, you know, and he could lay down fine. But if he sat down, his head already popped out of the thing. So there’s zero chance that he’s actually going to pass the legitimate test. And I but I’m not about to drive from Missouri through the states, down the Baja, which is a three-day trip on its own, with an eight-week-old puppy. So I’ve got to figure it out.

And I knew that there’re like two main obstacles here: one is American Airlines at the gate, and then one is TSA, right? So I’m already thinking like a salesperson, being strategic, what are the obstacles and the objections that I’m going to face. Those are the two main things I’ve got to think about.

So the first one, American Airlines, I’m not terribly worried about. Like I’ve flown American for a long time and I’ve got top-tier status, I’ve had that for years. Plus I give them money, right? So they have a vested interest in keeping me happy. I still go in prepared though, right? So I walk up and the agent’s like, “Oh, you have an animal? Okay, you’ll need to fill out this form.” And she hands me the form and she looks down at the carry-on.

I start in to my sale, right? I start in to my pitch like right away. And you know, I’m like, “Yep, new puppy, he’s just eight weeks old, my kids are at home, I’ve got two sons and we’re surprising them for Christmas and my wife is there, she’s getting ready, we’ve got family there because my brother-in-law was there with his girlfriend.” So like I tell this story, you know, and I’m like they have no idea they’re going to be so excited. And I get emotional—like not crying, but I get like pumped up, excited—and I paint that whole picture for, you know, you’ve got kids, you’ve got Christmas surprise, happiness. Who wants to ruin that?

And by the way, that’s not fake. Like that’s real, you know, I am excited and we do have family there and it is Christmas and they are going to be surprised. But I lean into it, for sure. She decides to actually say, “Hey, we need to run this test,” and actually look at all of the answers on this form, then he’s going to fail. Like there’s no way, so I preempted it. I proactively addressed the obstacles and the objections and I leveraged what I know about psychology, I leveraged what I know about sales, and I sold, right? And she didn’t know that she was being sold, but it worked. And by the way, I was better off for it, my family was better off for it, the dog was better off for it, American was better off for it, nobody was harmed in the process of making this sale, right?

So I get through that. You know and I get on to the real test because I wasn’t too worried about American; TSA’s really like the real issue. And that’s because they don’t really give a shit about me, per se, right? Like I don’t pay them—source sensitive topic, I know, so—but I don’t pay them, right? Like I’m not a customer of theirs necessarily, they don’t have any financial interest in making sure I get on that plane. So I know going in like I’ve got to bring my A-game to this.

So I walk up, I’m the first person in line, the agent mentions the dog as he scans my stuff and I start walking towards the belts and somebody else walks over and says, “Okay, can I see the puppy?” And I don’t know if she wants to see him because it’s a puppy and it’s two days before Christmas like “Oh, let me see the puppy” or “Hey, we’ve got to run this test.” Either way, like it doesn’t matter, so I run the playbook, right?

“Yeah, of course!” and I’m excited, I tell the story, you know, telling them about how my kids have no idea, they’re waiting at home with their uncle and their mom and we’ve been planning this for months and you know we had to get this all timed perfectly—which all of it’s true, by the way, again. Like think about this, we’re timing something months before Christmas, we’re trying to get a puppy on Christmas or right around Christmas—like that’s the... you can’t force pregnancy and babies. So this took planning, right? And I tell the story and I lean into it and I talk about the strategy and I talk about the surprise.

By the time I’m halfway through, one of the TSA agents is holding up the puppy like next to her face and she says, “I need me a puppy for Christmas too!” And they got engaged, right? Like they got into it, and obviously they let me through. So Shadow—which my kids named him—Shadow made it home on time, kids were excited, everything went perfectly. And by the way, if you like ideas like this broken down into something you can actually use, that’s what the newsletter’s for, you can sign up at raizemail.com, completely free.

Here’s why I’m telling you the story though. To me, this is sales. This is exactly why I keep saying sales is a life skill because when you understand how to sell, and really understand what sales is, you understand the power of storytelling. You understand the power of body language. You understand the impact of tonality. You understand how to anticipate objections and put yourself in somebody else’s mindset. You understand the psychology of motivation, where there’s alignment, where there isn’t alignment, how to address those gaps. You start thinking that way.

And when you really get that, you stop seeing sales as a four-letter word, right? Like you stop seeing sales as something to be uncomfortable with because so many people say, “I don’t like sales” or “I’m not a salesperson” or “I can’t do sales.” And when you understand what it really is, you realize we’re all selling, all of the time. Like you are selling something right now, I promise you. And I’m selling this idea to you right now. You know, in a formal sales role or not, like no matter where you’re at in a company, you’re selling your manager on an idea, on your performance, on keeping you employed, on giving you a promotion. If you own a business, you’re selling all day, right? Like you’re selling your vision, you’re selling your business to other businesses, you’re selling your spouse on why you need to clock 14-hour days and you know miss that, you know, whatever appointment in the time that you’re spending building your business.

And even if you don’t have a 9-to-5, you’re still selling. Like my wife sells me all the time, my kids sell me all the time, my damn dogs sell me all the time with the puppy dog look, right? I’ve been thinking a lot lately about why sales is hard for some people and not for others, and I think a lot of it just comes down to a misunderstanding of what sales actually is. And like sales is not pushing products people don’t want onto them with like strong-arm sleazy tactics to get a commission check—like that’s the version that’s been projected for years and a lot of people have bought that story. But that’s the exception, that’s not the rule.

Sales is a skill and it’s used in virtually every aspect of life. I actually have trouble thinking of a single person who doesn’t benefit or wouldn’t benefit substantially from getting better at it. And I can think of a lot of people, though, who’ve been limited in their lives and their businesses, even in relationships, because they bought into the idea that sales means getting what you want at the expense of someone else, and that’s not the case.

You know, like personally, I’m an introvert. I’m not a natural-born salesperson. I had to learn the technical aspects of sales the hard way. I was never extroverted, charismatic, like the glad-handing person you drop into a networking event that you and the person that you usually think of when you hear the word salesperson. And I personally can think of no more valuable skill for anybody to learn than this one.

So if you’re technical, engineer-minded, like operational by nature, like the kind of person who’s listened to this saying, “Yeah, but I’m not a salesperson, I’m not a sales guy, I’m not a sales girl,” I want you to reconsider what sales actually is because if you embrace it as a life skill, like something that can absolutely be learned—I’m living proof—something that creates alignment, growth, and yes, profit... like once you get good at that, it unlocks so many doors, including maybe getting your dog home for Christmas. Hope it helps. Adios.

About the Podcast

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The Ray J. Green Show
Sales, strategy & self-mastery from an operator, not a guru.