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Robin Waite, founder of Fearless Business, shares insights on pricing strategies, mindset shifts, and creating sustainable, profitable businesses. Learn how to attract fewer clients at higher prices, build meaningful client relationships, and avoid common entrepreneurial pitfalls.

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Robin Waite (00:00)
what is realistic? How many clients could, or would you like to work with over the next 12 months?

And that coach might say, well, actually 20 clients, that’d be really great. I could really pour into them, deliver loads of value, get them the results and outcomes, which they want. And I wouldn’t feel like I was overworked, but 20 clients at one case, it doesn’t add up. I’m not going to hit, able to hit my income goal. So what we do then is we take the big number, we divide it by 20. So now it gives us $5,000 for that product or service.

Dylan Silver (01:58)
folks, welcome back to the show. Today we’re joined by Robin Waite, the founder of Fearless Business. He’s a business coach, bestselling author and speaker who helps coaches, consultants and service-based entrepreneurs build more profitable businesses and productize their services. Robin, thanks for joining us today.

Robin Waite (02:19)
It’s a pleasure Dylan. Thank you for inviting me onto the show.

Dylan Silver (02:23)
Now, with so many business owners struggling to charge what they feel they’re worth and having consistent business, what do you see as a common bottleneck that entrepreneurs in this space face?

Robin Waite (02:39)
Yeah, I mean, the bottleneck is quite simple, really, I think there’s this unwritten rule for some reason in entrepreneurship in business where the goal in business seems to be to attract and enroll as many clients as you possibly can do, like all of the clients. And actually, I genuinely believe that the best business is one where you have double the income, but with half the clients. Because that’s a business for me, which is designed around sustainability and profitability. If all you’re trying to do is just

crank the handle and get as many clients through the door as you possibly can do. And I’ve been a party of this through my 22 year career. I’ve fallen foul of kind of burnout and getting to a point where it just becomes unsustainable because my prices have been too low. And I see this like with entrepreneurs all of the time, they just reach a point where they’re just tearing their hair out because they’ve got more clients and they know how to service. They’re not making enough money when they check their profit and loss accounts at the end of the month.

⁓ and ultimately, you know, shouldn’t the, shouldn’t the goal of business, you know, business should be fun. It shouldn’t be stressful. shouldn’t be getting, you know, detrimental to your health. ⁓ it should be fun. It should give you freedom and yes, it should pay the bills as well, but that shouldn’t be the only reason we go into business in the first place.

Dylan Silver (03:54)
Now for folks who are dealing with that bottleneck that you mentioned, know, trying to find more clients and not necessarily increasing their amount that they’re charging, but just increasing their volume. Is this a mindset shift that they have to undertake or is this something that’s purely logistical and they just need to focus on instead of volume clients, you know,

select few and charging more.

Robin Waite (04:27)
It’s a bit of both actually. So on the mindset side of things, we tend to look at other business owners and see them being busy fools. And we think that that’s the model that we have to copy. a lot of business owners are just seeing what others are doing and think that’s the way business is done.

There’s also seems to be a culture now. I don’t feel this was the same when I started my business in the early 2000s. But certainly in 2026, it feels like, you know, there is still this mentality around hustle and grind and

Hard work is the thing which is ultimately going to make you succeed as a business owner. I do think we need to start to reverse some of that psychology because this is a marathon, not a sprint at the end of the day. There are actually very few entrepreneurs who just want to make a million bucks quickly and retire. Most people get into business because they want to solve meaningful problems with their clients, help other people to succeed or help other people with their, you know,

achieve their housing goals and dreams and things like that, for example, in the estate agency world. So the mindset is just copying what other people are doing blindly without then asking whether that is the right way to do it. But there’s also the very practical side of it where a lot of small business owners, come up with these incredible ideas for a business, know, products and services, and maybe a relative or a friend or a colleague says, Oh my God, you should do this thing. You’d be so good at it. It’d be great.

So they launch into it, but the one important thing which they’ve forgotten to do is to create any kind of a plan. Now, I don’t believe we need like 42 page business plans that we’re going to send out to investors and banks and things like that. Cause again, that just doesn’t exist in 2026. However, what we do need to do is have some modicum of a bit of an idea about the direction we’re heading in. So I teach people about this very simple concept, this very, this one page business plan. And it’s literally five questions that you can ask.

which sets the scene for how your business is, how successful and easy or effortless your business is going to be in the future. So I’ll try and, know we’ve only got a short amount of time, so I’ll try and give the very precede sort of breakdown of it, and then you can ask me questions. So the first question is, what’s your dream income goal for the next 12 months? Where do you want to get to? And I’ll keep the numbers nice and simple, so it’s easy on my brain. I don’t have to work too hard doing maths. So let’s say for example, a business owner wants to make $100,000 and maybe they want to be a coach.

so that’s question number one, nice and easy. Let’s pick a number. Question number two is, ⁓ well, what price are you thinking of charging for your product or service? So that coach might say, well, I’m thinking that maybe for my signature coaching program, a thousand dollars. Okay, great. So that’s question number two is easy. just a number, right? Question number three, and this is where we start to get some insights from the, the, the chain of questions. ⁓

What’s your capacity? And to work that out, we take the big number of a hundred K and we divide it by the little number one K. And what we end up with is a hundred clients. And normally at this point, when the people I’m speaking to their eyes pop out their head or out, they got like through their glasses and they’re like, my God, I can’t possibly, you know, work with a hundred clients. That’s just way too many. don’t have the capacity for that. Or they might say, well, I could probably work with a hundred clients, but how do I attract all of those clients? Cause like, I’m doing all the marketing things, but I’m only getting like three clients a year at the moment.

So there’s our first test within three questions as to whether the business model that we’re thinking about building holds water or not. The next question is simply, well, is that, is it realistic or not to work with those hundred clients? And they probably will say, no. Okay. So again, really simple one page business plan guys. It’s not complicated. And then the fifth question is, okay, well,

what is realistic? How many clients could, or would you like to work with over the next 12 months?

And that coach might say, well, actually 20 clients, that’d be really great. I could really pour into them, deliver loads of value, get them the results and outcomes, which they want. And I wouldn’t feel like I was overworked, but 20 clients at one case, it doesn’t add up. I’m not going to hit, able to hit my income goal. So what we do then is we take the big number, we divide it by 20. So now it gives us $5,000 for that product or service.

Again, their eyes pop out the head at this point, because they’re like, Oh my God, I don’t know how I can sell a thousand pound.

thousand dollar coaching package, let alone a 5k package. And it’s like, well, what could you do for that person? We don’t just five XR prices and stack no extra value. It’s like what extra value could you add into your service or your products in order to make it a full and remarkable solution to guarantee the outcome result, to guarantee that client gets the results which are after. And then the cogs start worrying because they’re like, my God, there’s all this that I wanted to.

Send them a welcome pack. wanted to not just work with them for like eight sessions. Maybe I could work with them for six months, really intensively. Maybe I could do like a, ⁓ a retreat with them for three days in person. So they start to get really creative about all this extra stuff they can include that then moves their clients closer towards getting that, that dream outcome. So those five simple questions get us to a point whereby we know like the basic business model. The next thing then is like, how do we, how do we get, how do we build it?

Dylan Silver (10:50)
You know, when we talk about being able to have a more in-depth relationship with clients and help them not just in one specific capacity but in several, I see this as being a way where folks can get more out of their ⁓ client interactions even if it doesn’t translate into the ⁓ transaction amount that they had in mind.

And on a surface level, this can be something as simple as, well, if you’re able to provide value for someone, they could become a referral for you, they could send referrals your way, they could be a review. But then deeper beyond that, you look at all the other ways where they might not need assistance right now, but over the course of building their business or their home ownership journey, if they’re a homeowner and you’re a realtor.

There’s all these other ways where they could be assisted.

Robin Waite (11:47)
Hmm. It’s, it’s for me, it’s about introducing though, being able to introduce those moments of delight. So if you’re, if you’re a cheap commodity, you don’t have the bandwidth or the amount of cash basically cashflow to be able to add in like create moments of delight for clients. So, ⁓ like one of the things I mentioned in that example was, ⁓ I, I send out, just a very simple welcome pack with about 10 things in it, but the value of it’s about $300 worth of stuff that I put into it. And clients are like,

Wow. And it’s like, literally get, you know, voice notes from my clients within the first few days of them working with me. So I’m so grateful for this. It’s given me so much stuff to work on. I’m really excited about it. ⁓ and this came from, I, when I first started coaching, I booked onto a podcast concierge service, ⁓ called interview Valley and, thought nothing of it signed up. They started booking me the, it’s an American company. They were, they were booking me the podcasts, sort of going through the process and about three weeks later.

just cause it took that long for it to get over the Atlantic ocean, you know, the parcel got this wonderful bright orange parcel. And then it had this, ⁓ I forget the make of it, but it was like a $200 microphone. ⁓ it had, ⁓ it had this, ⁓ microphone thing, unfortunately it doesn’t fit onto my stand, but, it had this little Mike flag on it as well with my brand on it. Have these little, ⁓

don’t know what you call them tabards like and put hang on the door handle to say recording in process. They really thought about this package that they put together. it’s just, it was, it, it just felt me like, made me feel like I was really an important customer to them. Now I know they worked with hundreds of clients, right? But it just in those little things, you feel special. Everybody likes to be chosen. ⁓ and a final example, I was, you know, we moved house nine years ago. ⁓

And the first couple of house moves I’ve done, it was kind of very transactional. It was very much like, here’s your keys, here’s your house go. Like that was it. Like the estate agents didn’t really do too much to kind of really make us feel like exceptional. This house, however, I mean, it was quite a significant investment for me and my wife when we moved here. We should, get, get the keys to the house. We’d had a few issues with the, so I don’t know how it works in the U S but we exchanged in the morning.

We had to hand our keys over, we were effectively homeless for two hours. And we had to sit in the estate agent’s office waiting for our house keys to be ready for that end of the transaction. So now it’s like mid-afternoon, we had two young kids like who are three and one, you know, desperate to get into the house to move in. But we got here and they’d arranged a pizza delivery service for tea for us all. They put a hamper in there. So we had coffee, milk, bread, like all of the essentials. And it was all laid out in the kitchen.

There was stuff in the fridge. So they put all of that on for us. They didn’t have to do any of that. They’d done their job. They’d sold us the house, right? They didn’t have to do any of that. But we had a nice bottle of champagne that me and my wife could enjoy to kind of see our journey into the new home as well and celebrate that. Those little moments are like, who do think we’re going to use next time we want to sell our house? It’s going to be that same company, Just because of that one little moment of delight.

Dylan Silver (14:55)
That’s right.

⁓ Pivoting here, Robin, when we talk about Fearless Pricing what inspired you to write that book?

Robin Waite (15:52)
Yeah, great question. I’ve been in business, so my first business is a marketing agency. And ⁓ as a naive sort of 20 something, maybe slightly arrogant, I didn’t take advice from anyone. I was like, I know what I’m doing. And of course, I had no idea what I was doing back then. So I made pretty much every pricing mistake under the sun.

And in part by the, you know, through the 12 years that I ran that agency and we were able to eventually sell it because of some of the Intellectual Property that I built. um, I, I don’t know, I’m to put it simply. We struggled, we struggled financially for the, at least the first four years in that business before the penny dropped. I was like, we’ve got, it’s, there’s nothing wrong with our service. The reason we’re not making the money we want to make is because we haven’t set the business model up for success. Um, and I just, I’m just so passionate about.

small business in general, I want to see small business owners succeed and not make the same mistakes I made, not have to go through that struggle and try and figure it out for themselves. So fearless, Fearless Pricing is all about, ⁓ goes through some of the most common pricing mistakes, which people make, ⁓ through copying other unproductive like business models, seeing other, you know, real estate agents all charge the same percentage or the same fee structure, for example. And, ⁓

Seeing how you can differentiate your pricing model from that, rather than being stuck with what everybody else does. Practical examples, case studies of the businesses which I’ve helped to restructure their pricing, based around sort of creating profitability. But yeah, the underlying thing is I just want people to succeed. There is nothing better in business than without sounding too capitalistic, but…

Nothing better in business than having 50 grand sat in your business bank account and have a client come in who maybe has a load of red flags and you being able to say, actually, no, I’d rather not work with you. I’d rather not have to take on that client because you can see the problems that are going to unfold. ⁓ That’s, that’s the ultimate goal of Fearless Pricing is to have, have, be empowered to be able to afford to say no.

Dylan Silver (18:01)
We are coming up on time here, Robin, any new projects that you’re working on and then also anything you’d like to mention directly to our audience.

Robin Waite (18:09)
Yeah. So the big one, obviously the Fearless Pricing book is now sort of live on, on, available on Amazon and things like that. I’ve got some really cool partnerships coming up with some well-known influences. So I’m ⁓ got some associate coaching roles now with the likes of Ali Abdel and Daniel Priestley and Christo. These are specialist people, niche people you probably maybe haven’t heard of, but big in my world. So I’ve got some really exciting stuff coming up in that respect.

Um, but yeah, the Fearless Pricing kind of at the moment, Dylan, I don’t really have a big project cause I’ve just finished one. I’m like, right. I need a bit of a break now.

Dylan Silver (18:45)
Fair enough, fair enough, Robin. It was great meeting you. Thank you so much for your time today. Thanks for joining us on the show.

 

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