How the emotional effect of money, and communication, can get you noticed; with Bob Wheeler

In this episode of The Unnoticed Entrepreneur, host Jim James interviews CPA and author Bob Wheeler about the powerful role emotions play in an entrepreneur’s relationship with money and how clear communication can make a business stand out. Wheeler explains that confidence and self‑worth are the foundation of pricing decisions, urging entrepreneurs to calculate their true value, benchmark against competitors, and reframe services as problem‑solving rather than cost. He shares practical tactics for presenting prices—using upfront quotes, retainer models, and transparent timelines—to avoid surprise and build trust. The conversation also covers pricing psychology (e.g., adding a 25 % markup to counter under‑pricing), strategic payment terms such as upfront deposits with discounts, and the use of rush fees to incentivize timely client action. Wheeler highlights personal confidence‑building tools like Toastmasters and list‑making, and describes his systematic client‑communication workflow using MailChimp and an accounting‑specific “OfficeTool.” Finally, he explains how authentic, relationship‑focused engagement helps him get noticed in a crowded market. The episode blends emotional insight, concrete pricing frameworks, and communication best‑practices for entrepreneurs seeking to price confidently and attract attention.
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Hello and welcome to this episode of The Unnoticed Entrepreneur. Today we're going to talk about money and emotions and how your emotional attitude towards money can infect and affect your business and how you get noticed. And for that, we're going all the way to LA to talk to Bob Wheeler, who has over 1,000 clients for his business. He's going to share some wisdom with us. Bob, welcome to the show.
Thanks so much for having me. Excited to be here.
Well, I'm really excited because we've never talked on this show about the emotional aspect of money and how it impacts an entrepreneur gets noticed. And it sounds a slightly complicated topic, but as we were talking before we started recording, money and emotions and communications at the heart of a successful business. So tell us, you've written books about the subject. How does the emotional attitude towards money affect an entrepreneur?
Well, we're all emotional beings. And so we're going to connect emotionally. You may have something that I want, or I have something you want, but at the end of the day, how are we going to resonate with each other? And so for me, whether I'm feeling confident, which to a lot of people feels sexy or like I want more of that, or, oh, let me help you. And oh wow, they're not so confident. Maybe this isn't the path I want to go down. And so just even starting with how we see ourselves and how we value ourselves is going to have an impact on the business.
So let's just talk about that, Bob. So you said, you know, being confident. is sexy, but most entrepreneurs, myself included, you know, we're not mathematicians, we're not accountants, you know, like you are. What can an entrepreneur do to increase their self-confidence around money and around pricing and negotiation? Take us through some of those dimensions if you can.
Absolutely. So it's really important from my perspective to get clear about what I'm worth. What am I going to bill? It might be that I do a spreadsheet and I put in this much time and I use these kinds of equipment and I have all these things that I need to factor in my rent, my overhead, and come down to what am I worth? Now, sometimes people will discount their worth or, oh, you know, I've got to put in 2 hours to bill for an hour. Get really clear about what those values are for yourself. And when you know what you're worth, you can Clearly, confidently express that, communicate that to your client.
So you say, what are you worth? There's that old story, isn't there, that's, you know, what am I worth to myself? But then there's also, what am I worth to the client? What problem am I solving? How do you help entrepreneurs, if you like, to reframe the conversation, not so it's just a cost-up model, but that you're being seen by the client as solving a bigger problem and therefore You know, able to charge more for that?
I think it's important to know what your competitors charge. I want to know what everybody else is out there charging, what they're offering in terms of service, so I can look and evaluate my experience, evaluate my education or anything that might contribute to my value. I want to know what's out there. If other people are charging twice as much as me, what are they doing different? Am I bringing more value and just not educating the client as to what I'm bringing them?
So you talk about, you know, competitor analysis, and we're talking as well about what clients want. Can you give us some practical examples of how a company should communicate pricing? In retail, of course, there's, you know, the price on the internet or whatever, but if you run a service business, what sort of tips can you give us from a communications perspective for entrepreneurs about how to present pricing? Should it come at the beginning in the quote process? Later? Should it be on a website? Give us some ideas there, can you, Bob?
I think it's always important to clearly communicate what they should expect to be charged upfront so that if they've got cold feet, if that feels too much money for them, you can stop the process before you've invested your time and energy. I used to do free consults and people would come in, they'd do an hour and they would ask all kinds of stuff that I should have been charging for. And then later on I'd say, hey, time to do your taxes. You're like, oh, I went with somebody else, but thank you for all the free advice. So that was a place where I was spending a lot of time and not valuing the fact that I'm giving these people some good information. And so I was able to change that model and say, look, you want to meet with me, it's going to cost you, but if you stay on as a client, I'll apply that towards the retainer, towards the ultimate fee.
That's a really, really good idea. What about the sort of presentation as well of let's think about quotes first, or anybody with sort of pre-consultation fees. You talked about embedding that fee into the overall project, but any guidance, Bob, that you see? What works for making the customer feel, oh, this is the company I really want to work with?
So I make it really clear, and I think it's important to communicate to clients, here's what you can expect, here's the timeline. I'll even tell clients, look, during tax time I get a little busy, and if you feel You know, neglected, please call the staff. They will come in and take me to task. It's nothing personal. I just get caught up. And so I try to lay everything out so that I'm managing their expectations so that they can say, okay, I could live with that. This doesn't work. I try not to overpromise because I find I'm going to disappoint. And so I think it's really important to say, this is what you can expect. This is the fee. If there's more work to be done, I will let you know ahead of time. That there's going to be an adjustment to the invoice and you'll need to okay that before I move forward. So I try to keep people in the process the whole time. I let people know if you're confused about the bill or it feels too high at the end, let's have a conversation and we can go through it. I try to be very transparent and I really welcome the client being able to come back to me with me not attacking them or shaming them for questioning how I bill them. I think it's so important to be in communication.
Yeah, so really at the heart of it, that communication side. Fantastic. And then you've also written a book about, you know, emotions and money. Do you want to just maybe talk with us about how an entrepreneur can become more sexy through becoming more confident? We talked about some of the tactical things. From an emotional point of view, how can you help an entrepreneur to feel more bullish about what they've got to offer?
Well, I like making lists. I like writing stuff down because it makes my brain activate when I'm, oh, here's what I'm bringing. I think it's important whether it's, I'm not confident in talking to clients, then I want to learn how to talk better. I joined Toastmasters so I could speak because I could barely say my name without like having a meltdown when it came to public speaking and meeting people in a business setting. I was very awkward. So I did Toastmasters. I learned how to talk, whatever those things might be that will make you a little bit stronger. Go to the places that you feel fearful around your business and get used to it. Say, oh, I like when a client rejects my offer. I'm not taken out. Oh, okay, cool. We're not a fit. I'm not worried about it. I will sometimes meet with clients to decide if we're a good fit for each other, because I don't want to waste my time and I don't want them to waste their time. So I'm constantly trying to figure out how can I make them know that I'm all about servicing their needs, but at the same time, not giving away my services, not undervaluing myself and not apologizing that I'm here to get paid to do work, to help you be the best version of yourself.
Bob, let's just also just think a little bit about pricing, can we? Because most of us Struggle with, you know, we talk about what you're worth and competitive pricing. Can you just give us some guidelines and if you like a way to stop underpricing? Because most of us struggle with that.
So one of the things that I do with a lot of my clients is right now, if you're billing $150 or if you're billing $200, multiply that by 1.25. I figure most of us are discounting ourselves 25%. Maybe more. And a lot of clients are uncomfortable with that. So maybe even if they do 1.15%, if they mark it up 15%, they're still starting to make some movement towards, yes, this is what I'm worth. What's interesting is probably 95% of the time I've encouraged them to change their billing by doing the 1.25%. Nobody says a word. Everybody's like, oh, that's cool. I even had a client of mine said to me one time, you're not billing me enough. I feel guilty because I know what the going rate is when I was first starting. It's like, please bill me more. I mean, don't break the bank, but you're not billing me enough.
That's really interesting how we psychologically undervalue quite often because we're so embedded and invested in that, you know, at the beginning. Bob, what's your view on how early you should be giving a customer like a price sheet, for example, or a price guide? You know, some people leave the pricing To the end of the conversation. Some people feel it should be at the beginning. Any guidance, your experience on that?
For me, when I'm talking with clients, do it in the middle. I want to connect with them first. I want to let them know I'm interested in connecting with you human to human, and here's what I can provide. But pretty much right after that, I want to remind them that there's a fee involved and this is what it's going to cost you. I don't want to leave that to another conversation. I don't want to leave it to the end because I want to make sure that they have time to process, integrate that information that I've just given them so that if it's going to be a go, great, we're on the same page. If there's some hesitation, we can talk it out and then we can decide where we're going to go. But if I save that to the end, to me, that feels like a surprise ending and it doesn't quite feel so good. I feel like I just got weighed. I was just a bait and switch. I want to know early on what I'm getting into so that I can either say, whoa, whoa, that's way beyond my price point. Or yeah, this is totally in line with what I was expecting.
Okay. Yeah, that's really good because there's some sort of one school of thought says name price first to frame the conversation. Others leave it till the end when they've already kind of invested all the time and you're kind of a midpoint, which is a really nice way of doing that. I like that. Now, you yourself have also done some quite interesting things around shifting payment terms and how that can position your company differently. In your case, as a CPA, but not necessarily just as a service firm, to use the timing of payments as part of your proposition. Could you just tell us about that, Bob? Because I think it's a really interesting point we were talking about before we got the mic to record.
Yeah, absolutely. So one of the things that I learned early on, especially in a tax practice, a lot of tax preparers, CPAs, are cash poor at the beginning of the year because they're not going to get paid till April, May, June for a bulk of their money. And so I was struggling with that as well. And I was at the seminar and this guy said, oh, I bill everybody upfront, which was a little bit unsettling for me, but I thought, this is something I like, this idea. And so I sat down and I actually wrote an email to all of my clients. And I said, look, I can either be a banker or a tax strategist. I can either focus on helping you save dollars and give you the best bang for the buck, or I can run around trying to collect money, worrying about I can't pay my staff. And so what I suggested to everybody was I'm going to ask for half of the money upfront. I'm going to ask for a retainer. And hey, by the way, you'll get to deduct that on last year's taxes. If you pay early, you get a benefit. But if you do this, I will be focused on you instead of focused on how am I going to pay the bills? I did not have a single person push back. People love the idea. And what started to happen was by November, December of the year before I started tax season, I'd have $100,000, $150,000 in the bank. So I'm already solid in my financing. The other thing that I would say is In any business, if a customer says, let me give you a deposit or let me put some money towards that, don't say no. Absolutely. Let the cash flow towards you. There's nothing wrong with saying, yeah, absolutely. So I know so many people, no, no, no, no, let me do the work and then take the money.
Um, okay, Bob.
So be confident.
Yeah. Okay. So there's a derivation for you. What would you say is a good strategy around discounts for prepayment and so on? Because You have some guidance for people about that? Because you've mentioned about getting money upfront, but what's the incentive for the customer other than you saying, I'll be committed to you? They would normally say, well, you should be committed to me regardless, right? So any, any guidance about pricing to make it more favorable for the customer to pay early?
Absolutely. So when I tell people that they do the deposit upfront, we give them a 10% discount on the back end. And we also tell people, if you get us the information 2 weeks before the deadline, there's going to be a $500 rush fee. And we start letting people know a month ahead of time, reminder, if you don't get stuff to us in 2 weeks, you're going to get hit with a rush fee. We're going to add on a lot of extra money if you don't get your stuff in. So we try to communicate the whole time, pay us early, we'll give you a discount. Pay it late or get us stuff late, you're going to pay a premium because we will add on a late charge or a rush fee for people because we don't want to be— I don't want your drama to become my drama, right? So just because you're having a crisis doesn't mean I have to have my whole office in a crisis. And so we let people know, if you wait and you don't deliver on your end, you're going to get charged for that because it has to be a win-win for everybody.
Bob, I'm interested in obviously that as a strategy, but from a communications perspective, when you say I let my clients know, Can you just give us a little bit more detail? When do you let them know? Is that in like the advance at the very beginning in the quote stage? Is it in an invoice? Is it so, uh, yeah, in informal email? Just give us some guidance there of how you implement that because that could go very wrong as well, couldn't it?
For sure. So when people come on board initially as a client, I let them know we're going to send out an engagement letter. It will include the pricing. And you'll get that in November and we'll ask you to pay a retainer. If you don't pay the retainer, you won't get the discount. And you may not get a face-to-face appointment with me before April and you may have to go on extension, right? So there are benefits to making sure you get that retainer in. You've saved your spot. You're guaranteed that we've made space for you. And so I do that upfront. Then during the tax season, we'll send out an email. Hey, you've got 6 weeks left. We haven't heard from you. You've given us a retainer. We need to see the information. What's going on? We communicate a lot with the clients because we want to make sure, hey, did something happen? We were communicating, then all of a sudden no more documentation. Oh, you need to go on extension? We'll go on extension. But we're in a constant communication with the client because people get emotional around money, right? And so they shut down when it comes to doing their taxes, or they might think they're going to owe money. So now they don't want to talk to me anymore until the last day. And so we're trying to stay engaged to let people know, hey, we're with you the whole way. We get that this can be emotional and we need to get it done. It's a requirement. You need to file your taxes. So we're communicating throughout.
That's perfect. From a practical point of view, can you just share which tool do you use for your email marketing?
We use, is it Chimp?
MailChimp?
MailChimp. I know it's an animal that we can track everybody. And then we also in the accounting world, the tax world, there's a program called office tool that also lets us track and list and modify. We have like pro forma letters that we can send out.
Okay, nice. So really systematized. Now, Bob, final question. You know, I love to ask entrepreneurs like yourself how you get yourself noticed. You've gone, built this practice. You said you're managing 3 businesses combined out of LA. How have you got yourself noticed as an entrepreneur or got your own businesses noticed? As an entrepreneur?
I think the way that I get myself noticed is I engage authentically with my clients. People know that I'm going to bat for them. People feel that. People will tell me, look, I know, I get the sense that you're actually going to bat for me. I'm here to help people. And so I let people know, I like people. I want to help you, right? If you work with me, I'll work with you. But it's a two-way street. I need you to be the team player so I can give you the best service. But I'm truly engaged. I follow up. I check in with my clients after tax season's over. I send an email, I make a phone call. I know whose kid just graduated. Like I'm fully invested in the relationship. I'm not looking at it like a transaction. And I think my clients and potential clients can resonate with the fact that I'm actually there to be in relationship.
Bob, that's wonderful. Look, and thanks for sharing some great advice. We only have 20 minutes, as you know, to cover such a huge topic. You've got a book, Mastering the Emotions of Money. And if you want to find out more about you and how to get ahold of you, where would they do that?
Best place is themoneynerve.com. That's nerve, not nerd. I'm both. I get on people's nerve, but I'm a nerd. themoneynerve.com. And there's lots of resources, information. You can contact me through that.
Bob Wheeler joining me from LA to talk about money. And the reason I want to share it on a podcast around getting noticed is because often as entrepreneurs, We do all the great brand building, we do all the great product building and the service building and development, and then we kind of crumble when it comes to the pricing and where we put the pricing and how we position and ultimately how we negotiate. So Bob, thank you for telling us, you know, being confident is sexy and we could do that by preparation and through communication. Thank you so much.
Absolutely. Thank you so much.
Great. Well, you've been listening to me, Jim James, on this episode of The Unnoticed Entrepreneur. And as always, I'll put all the links in the show notes. And if you've liked this, please do share it with a fellow entrepreneur. And if you've got a chance, rate the show on the player. Really all helps. Until we meet again, I do wish you the best and do keep on communicating.
Thank you.
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