Merchant Sales Podcast · 2026-07-10 · 8 min
Key moments - from our scoring
Substance score
56 / 100
Five dimensions, 20 points each
This throwback episode pulls from a nine-year-old video to highlight unglamorous but effective merchant services sales fundamentals that rarely get discussed in modern training. Shepherd emphasizes the psychology of entering a business: adopting a customer mindset, looking around casually, waiting for the manager to engage first, and only then transitioning into a quick question about their business. The core insight is that business owners are primed to help potential customers, not dismiss salespeople, so positioning yourself as the former changes the entire dynamic. Specific tactics include complimenting the business, asking how long they've been operating, using the line "I just have a really quick question for you," and having a contextual reason for being in the area (visiting another client, installing equipment) rather than explicitly stating you're there to sell. Shepherd addresses edge cases like busy stores with customer lines and competing customers, advising you to blend in as a regular patron and respect the queue. This episode benefits sales reps and merchant services leaders who want practical, field-tested approaches to cold walks that don't rely on aggressive openers or philosophical sales frameworks.
Enter with a customer mindset, look around casually, let the manager approach you first, compliment the business, ask how long they've been open, and only then transition to your pitch using the phrase 'I just have a really quick question for you.'
If there's a line, get in line like any other customer and hand them your card when it's your turn; if there's just one customer, walk around the store and look at products as if browsing, treating it as a break in your day.
Always have a contextual reason unrelated to selling them - such as checking on another client, installing equipment, or just being nearby - rather than admitting you came specifically to pitch merchant services.
Keep initial rapport-building to roughly 10 seconds of conversation (asking how long they've been in business) before transitioning with 'I just have a really quick question for you.
Focus entirely on the owner and don't be nervous about people around you; if your pitch is interesting, the owner will often ask staff to handle the other customer so they can continue talking with you.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode delivers concrete, field-tested tactics for cold walk-ins (positioning as customer, waiting to be approached, using small talk as rapport-building, having a situational reason) that are genuinely practical and underexplored in typical sales training. However, the advice is relatively narrow in scope - it covers a single interaction phase - and lacks depth on objection handling, closing, or broader sales strategy. The 9-year-old video also adds limited new thinking to what should be current best practices.
I walk in and almost kind of, like, sheepish a little bit. And I just kind of walk in. I'm, like, looking around, you know, everything.
Always make sure you have a reason for being there. If your reason is, I came here to sell you, that's a really bad reason.
The core insight - that projecting as a customer rather than a salesman elicits better receptiveness - is psychologically sound but not novel; it reflects classic sales principles about first impressions and rapport-building taught since the 1980s (Tom Hopkins, Brian Tracy). The specific tactical framing (looking around, letting them speak first, the 10-second small talk window) has texture, but the underlying idea that authenticity and low-pressure approaches work better is well-trodden ground. The speaker himself acknowledges recycling old training wisdom.
Sales training is usually made by salespeople who, you know, used to be really good at selling 20 years ago and now they make these like big philosophical ideas.
I always say that line, just have a really quick question for you.
Speaker A/James Shepherd has legitimate credibility: he personally sold over 700 merchant accounts face-to-face and continues in the field, giving him direct, real-world experience rather than theoretical knowledge. He explicitly positions himself as a practitioner, not a career podcast guest. However, the episode lacks a second guest - it is primarily a solo host replaying his own 9-year-old video - which limits the dimension scoring and reduces the opportunity for diverse perspective or challenge.
I've personally sold over 700 merchant uh, accounts myself face to face walking into businesses.
I doubt you will find very many people that are better at it than I am. Honestly.
The episode includes specific tactical steps (looking around, waiting for 'can I help you', the 10-second small talk, handing a card, saying 'just have a really quick question for you') and real scenario handling (customers at counter, lines, people behind you). However, data is sparse: the claim of 150 cold walks in a week with zero rejections is anecdotal, no conversion rates are cited, no A/B comparison to other approaches is provided, and the merchant services context is narrow. Generalizability to other B2B selling is unclear.
Of the businesses that I've walked into in the last week, not one of them has asked me to leave. Not one of them has been even negative. Not one single business that I walked into out of the, I don't know, 150 or so.
I have a business right downtown here in Altoona.
This is a solo monologue replayed from a 9-year-old video, not a conversation. There is no host-guest dynamic, no follow-up questioning, no productive disagreement, and no probing of assumptions. The speaker is occasionally self-aware (acknowledging his weaknesses, crediting other trainers) but there is no interviewer to push back, ask for examples outside merchant services, or challenge claims. The framing as a 'throwback' adds context but does not compensate for the lack of conversational engagement.
So this video I actually did nine years ago.
There's a lot of things I'm terrible at. You can ask my business partner, you can ask my wife.
Computed from the transcript - who did the talking, and the words that came up most.
This week’s Merchant Sales Podcast is a special throwback episode. While on vacation, James revisited one of his favorite sales training recordings from nearly a decade ago - back when he was personally walking into businesses every day and building a portfolio of more than 700 merchant accounts. In this short but practical episode, James shares timeless field sales techniques for approaching business owners, building instant rapport, handling real-world prospecting scenarios, and making stronger first impressions. Whether you're new to merchant services or have been selling for years, these foundational strategies are just as relevant today.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Foreign. Shepherd here with another edition of the Merchant Sales Podcast coming to you today from the Chicagoland area. So got audio only this week. You're gonna hear some background noise here. I'm actually at my parents house on vacation this week and I uh, had
Speaker B: a really cool idea so I spent
Speaker A: a little time just looking through some of my really old videos and I was, what I was looking for was some videos back during the time when I was out in the field nearly full time selling merchant accounts. Um, I've personally sold over 700 merchant uh, accounts myself face to face walking into businesses. And so I wanted to go back to that time and just provide some really practical tips for those of you that are actually selling merchant services or you have a team of people that are selling merchant services and you want to provide them with some real practical insights for the week. Because there's a lot of things that do not get covered in the merchant services industry. Uh, these days around sales, we hear a lot about fintech, we hear a lot about software, but there's just some core foundational things that you need to understand. So that's what I cover in this week's episode. It's very, very short but I think you'll get a lot out of it. Um, if you can get that. I personally enjoyed kind of going back. So this video I actually did nine years ago. So this is, this video is nine years old. So again the audio, I thought it would go well with my intro here where I'm on my earpods at my parents house. Um, but again I apologize in advance, the audio isn't great on this particular episode. But again just a short one to give you some tips. As always, this episode sponsored by Nativia. Head over to nativia.com ccsalespro to check out everything they have to offer. Again, nativa.com ccsalespro but that being said, let's dive into this uh, throwback episode and listen for a few minutes to some sales tips to an earlier version of James shepherd who was actually out in the field consistently selling merchant services.
Speaker B: Welcome to the Merchant Sales Podcast. Hi, my name is James shepherd and today I'm going to talk to you about how to walk into a business to make a sale. It's really simple. But you know what, what the things that just cracks me up about sales training is that sales training is usually made by salespeople who, you know, used to be really good at selling 20 years ago and now they make these like big philosophical ideas. And don't get me wrong I love it. I mean, I'm a big fan of Tom Hopkins and Brian Tracy and, you know, even Grant Cardone. Some of his stuff I like. So I like it. But the funny thing about it is that a lot of times it's just not very practical, and there's so much that they leave out. I actually was out in the field, uh, this last week, and one of the things that really struck me that's interesting is how much there is to know about just how to walk into a business. What do you do when you walk in and there's customers there? You know, like, do you interrupt? Do you, like, just stand around? Do you, like, you know, stalk the manager? What do you do? You know, when the customer leaves and there's a customer behind you, do you let them go? You know, like, what do you do? Uh, it's really, really interesting. So I'm going to talk to you today about this, and I'll be honest with you. Um, there's a lot of things I'm terrible at. You can ask my business partner, you can ask my wife. There's a lot of weaknesses that I have, um, when it comes to walking into a business. I doubt you will find very many people that are better at it than I am. Honestly. Um, of the businesses that I've walked into in the last week, not one of them has asked me to leave. Not one of them has been even negative. Not one single business that I walked into out of the, I don't know, 150 or so, none, um, of them have been negative about it at all. And so I do know how to do this really, really well. So let me tell you what I do and just kind of share my experience of walking into a business and how I make it work. The first thing I do is when I walk into the business, I always, always, always walk into a business like a customer. I get myself in the mental mindset of, um, a customer always. Okay? And the first thing that I say is always something that a customer would say without fail. So when I walk in, I'm not carrying anything. I have my, uh, well, you can't see here, but I got my one hand in my pocket where I have my business card so I can quickly pull a business card out, um, and my other hand out of my pocket, and I walk in. And when I walk in, I first walk in and look around. Now, let me tell you why this matters. This is so important. It's a little detail. Boy, it really, really matters when you walk in and start looking around. Guess what the manager is thinking. They think that you are a potential customer that's looking around, and they get into this mode where they want to come to you, and they want to try to sell you on one of their products and services. And it just puts them in a very, very different mindset. And one thing that, uh, you know, if you walk in super confident, and you just, like, walk right up to the counter, hi, I'm James Shepherd. You know, I'm here to sell you something. Um, that doesn't work nearly as well. I walk in and almost kind of, like, sheepish a little bit. And I just kind of walk in. I'm, like, looking around, you know, everything. And then usually I wait for them to say something first. So usually they're going to say, can I help you with something? Or are you trying to find something? And when they say that, I always say exactly the same thing. I say, wow, you know, uh, this is really a nice place. I didn't even realize this was here. I don't think I've ever been in here before. How long have you guys been in business? And so I start with something that a customer would say that kind of gets a conversation going about their business. I still haven't even pulled my business card out yet. They don't even know I'm there to sell them something. They think I'm a customer. So we start to have a little bit of rapport, and then it's very difficult for them to switch gears from that to saying, get out of here. We don't want anything. You know, So I talked to them, just. And I mean, I'm talking about. I'm talking about literally 10 seconds of small talk. You know, how long have you guys been here? 15 years. Wow, that's awesome. Then I transition right into me. Well, you know, I actually just have a really quick question for you. I always say that line, just have a really quick question for you. And they're like, okay, I have a business, uh, right downtown here, uh, in Altoona. And I go through my little spiel. I have a business right downtown here in Altoona. And then I talked about that, and then I just said I just wanted to stop by and drop off my business card. Then I hand them a business card. Then I continue with the rest of my pitch. Okay, so that's how I do it. Now, a couple of special case scenarios. You walk in, there's customers at the counter. What do you do? You walk around the store and look at things as if you are a, uh, customer. And you can do that for five minutes or 10 minutes. Look at that as your break for the day. Um, so if you walk into a store where it's like, there's not a big line of customers, there's just one customer at the counter. And then you just walk around the store. If you walk in, there's a line of people get in line, and when it's your turn, you hand them your business card. You say, I just have a really quick question for you. And you do your whole spiel about that. The only thing you skip is if there's a line of people and it's your turn, you don't say the whole thing about, how long have you been here? You just go right into, um, yeah, I just had a really quick question for you, and you handed me your card. Um, the other thing is, always make sure you have a reason for being there. If your reason is, I came here to sell you, that's a really bad reason. Your reason needs to be something like, I was actually in the area because I was checking on my client XYZ company or I just came from installing a new credit, uh, card machine. You see the new emv, the chip card terminals? They're like, yeah. Oh, yeah. Well, I. I was installing one of those over here at this place. That's why you stopped by. There has to be a reason you stopped by. It's not just to sell them. What was the other thing I was going to tell you then? What if you come in and there are people behind you, you always go ahead and you wait your turn like any other customer would, and then you say what you're going to say. Um, and then you move on. Don't be nervous about the other people around. It's just you and the owner. If you can really focus in on that, you'd be surprised how many times the owner will say, this happened to me several times. The owner will say, uh, hey, Susan, come here. Can you take this customer here? And they'll move to the side to have a conversation with you if they feel like what you're saying is interesting. And that's where it goes into what you're selling. Obviously, you got to be selling something that's of interest to them. Otherwise, you know, you're not going to get anywhere anyway. So that's really it today. I know that doesn't really sound like a lot of, uh, you know, it's just details. It's like, little stuff. But if you're actually out in the field walking into businesses, it does matter. How you do that and hopefully those tips will help you today. Thank you for listening to the Merchant Sales Podcast. Whether you are an industry veteran processing executive or just trying to learn about the payment space, we appreciate your time. We hope you will tune in next week for more information and tips on building your merchant services business.
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