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How to Be a Seven Figure Consultant with Douglas Squirrel

April 30, 2021
Episode 8
The Recognized Authority Podcast Cover

The podcast that helps experts & consultants on the journey to becoming a recognized authority in your field, so you can increase your impact, command premium fees, work less hours, and never have to suffer a bad-fit client again!.

People use the word “remarkable” quite often in conversation, but I think we don’t give much thought to the literal meaning. Douglas Squirrel has done just that, and made it a deliberate part of growing his solo consulting business to over $1MM in revenue.

In this episode we talk about how he built a reputation in a small community by delivering big results.

Show Notes

I just love how casual Douglas is about building a million dollar solo consulting business!

I have several take-aways from what Douglas said here:

  1. Firstly, about deliberately making his work remarkable and even spectacular, something people will tell their friends and peers about – that is very interesting and seems like a major contributory factor towards that 7 figure revenue.
  2. Secondly, he’s doubling his pricing all the time. I think this is crucial – when you are providing huge value, you can command very high fees.
  3. Finally, although Douglas said he wouldn’t say he’s specialized, actually I think he is vertically specialized: he said he has done “a lot of different things” in “a community that talks to each other a lot”, the “founders of startups in London” and he’s helping with “their tech team”.

Specialization is a topic that I’m almost a broken record about here on the podcast, because I’ve seen it have such a major transformative effect. If you haven’t already listened to Jonathan Stark (episode 2), or Sara Dunn (episode 3) of the podcast, I highly recommend checking those out.

Links to learn more about Douglas

Guest Bio

Squirrel​ has been coding for forty years and has led software teams for twenty. He uses the power of conversations to create dramatic productivity gains in technology organisations of all sizes. Squirrel’s experience includes growing software teams as a CTO in startups from fintech to e-commerce; consulting on product improvement at over 100 organisations in the UK, US, and Europe; and coaching a wide variety of leaders in improving their conversations, aligning to business goals, and creating productive conflict. He lives in Frogholt, England, in a timber-framed cottage built in the year 1450.


Douglas Squirrel  00:00

So I keep it keep doubling my prices and that keeps working out well. And what I built that on is the very spectacular work that I’ve done for clients and spectacular is to use a word I use intentionally. It is. It is a spectacle. It’s the sort of thing that people want to go and tell their friends about.


Alastair McDermott  00:23

Hello, and welcome to Marketing for Consultants. This is the podcast that helps independent consultants and subject matter experts to get more clients without having to beg for referrals or make soul-destroying cold calls. I’m your host, Alastair McDermott, and today my guest is Douglas Squirrel. He is a software consultant with 40 years of coding experience. For the last 20 years he’s been leading software teams consulting and product improvement, and coaching leaders as CTO and startups in FinTech and E-commerce. He is an independent consultant who has grown his business to over $1 million in revenue with no explicit marketing. So Douglas, can you tell us how did you do that?


Douglas Squirrel  01:02

Did lots of very good work in a community that talks to each other a lot. So there’s a small community of the sorts of people that I talked to the sorts of people that I do work for, I was literally just on the phone with one of them this morning, lining up a new piece of work. And the method has always been to do very good work that they can then talk about. And to make sure that it’s explicit that I asked for referrals that I encourage people to talk about me, and to learn more about what I do.


Alastair McDermott  01:34

Okay, so the first thing is, it’s a small community. Okay. So So I take it to mean that you’re quite specialised, then would that be true?


Douglas Squirrel  01:44

I wouldn’t say that, actually. So I’ve been very generalised. I’ve done an awful lot of different things in that community. So the right, and I wouldn’t mind doing things outside that community. I’m always trying part of being on your podcast is getting more people to know who I am and what I do. So I’m always looking for ways to broaden actually, and I’m not trying to be very specialised at all.


Alastair McDermott  02:06

Right, okay. Can you tell me more about this this community? Like, is it the same kinds of companies in there the same types of people?


Douglas Squirrel  02:13

Yep. So I specialise at the moment. So just talking about specialisation. At the moment, the sorts of people that I talked to, are the founders of startups, and particularly the ones who know me the best, the one where the ones where I have the reputation that helps drive my business are founders of startups in London. So if you’re a founder of a startup in London, and you ask somebody about someone who can help with their tech team, it will be unusual for somebody not to mention there’s this guy who has a name, it’s kind of like a rodent. I don’t quite remember what it is. There’s some guy who does this. I my friend used them, you know, go talk to him. That that is a reputation that I’ve built through that good that successful work over five or six years.


Alastair McDermott  02:58



Douglas Squirrel  02:58

Try to broaden that. So I have some clients in Australia and in San Francisco now. I have broadened out to a local company. Actually, it’s not far from me. That is somewhat bigger is family owned business. I’ve had a few of those. Still a midsize company. So I haven’t worked for the fortune 100 kinds of footsie 100 kinds of companies, and not really terribly interested in those not actively going for them, although I talked to one if they phoned up. But the folks who know me and talk to about me to each other, are in this tight knit community of startup, startup, typically tech startup founders in London.


Alastair McDermott  03:39

Okay. It’s interesting you say that, that you’re not specialised. But that seems quite nice. So


Douglas Squirrel  03:48

That’s where I did the work. And this is very important that the people that I started with, were the folks that I knew the mill you that I’ve been working in for 15 years when I started. But I then was very willing to do quite different things for them. So I started doing transformations of tech teams that weren’t functioning well. But I’ve wound up doing documentation, projects, management, coaching, I’ve coached a sales leader. I mentioned going into not a startup, but a company that’s a family owned business. I’ve done a few of those midsize family businesses where their tech isn’t working. So I’ve branched out beyond tech beyond the kinds of projects that I started with a big one that that really paid off for me is doing due diligence for venture capitalists. So those were natural people who referred me because they know all the startup founders, and then I noticed that they had a need. So I said, ‘Hey, I can help you evaluate companies. So would you like me to be part of your do your due diligence process?’ And they said, Yes, please. And now that’s a significant contributor to my business.


Alastair McDermott  04:55

Very interesting.


Douglas Squirrel  04:56

And my strategy is to say yes to things and to not insist specialise and to say I can help with most things that affect people that I encounter. And not to say that’s not for me. I don’t do that. I can’t help you with that. There. There are cases where I do that, but but much more frequently on saying, Yes, I can branch out into that direction.


Alastair McDermott  05:18

Are these typically custom projects and that you’re doing?


Douglas Squirrel  05:22

Yeah, but there’s, yeah, but they are all different, of course. But there are some, there’s some standardisation, for example, you can hire me for advisory work, I call it the squirrel phone, you just, it’s like the bat phone, but it’s better. And you just pick up the phone, and you push the buttons on the phone. And you talk to me. And I describe it in that way. Because so many people have forgotten how phones work. They think that first you have to go to calendly and book something and then confirm it on WhatsApp. And then on the day, you also have to you just don’t do any of that stuff. You just pick up the phone and push buttons and you talk to me. And that’s got a kind of standard price. I’m thinking of you putting it on my website as a product that you can buy. And right people just buy that. So that’s quite standard thing, of course, then all the questions that I get are completely different. And I get to know the company and I help them in that ad hoc way, in different ways. But that’s that and the due diligence are kind of standardised, there’s kind of a price I have for doing it. It’s a standard process and so on a lot more of the work. outside those two areas are customised projects for transformation of teams, and every one of those is different.


Alastair McDermott  06:34

Right? And so, I mean, you must have some pretty high value projects going if you can get to $1 million in revenue?


Douglas Squirrel  06:43

Yep. So I keep, I keep doubling my prices. And that keeps working out well. And what I built that on is the very spectacular work that I’ve done for clients and spectacular to use a word I use intentionally. It is, it is a spectacle, it’s the sort of thing that people want to go and tell their friends about. So taking a team that is completely delivering, you know, has been delayed on a single project for a year. And within a month, they’re delivering new value every day. That’s the sort of thing I do again, and again, and people want to tell that story. So if I had simply taken a team that was kind of not performing great, and I made them poor perform 10% better, that might be very valuable, then that might make the company excited about what I did and want me to come back and help another team. But it wouldn’t make them go down the pub and say, Hey, I have this person. And my team is suddenly so much better. Yeah, this guy Squirrel, you got to talk to him. So your element that’s important.


Alastair McDermott  07:38

Yeah. So so you’re on the transform, transformation end of the spectrum rather than optimization?


Douglas Squirrel  07:45



Alastair McDermott  07:46



Douglas Squirrel  07:47

And where I’m optimising it’s dramatic optimization,


Alastair McDermott  07:50

Right? And


Douglas Squirrel  07:51

You’d want to go and say, you know, this used to be 5%. And and now it’s at 120%.


Alastair McDermott  07:58

This is kind of built in. Built in virality, about the about people wanting to talk about it, because it’s so spectacular. Can you tell me a little bit like, like, did you specifically start to do that? Or did that just come about naturally? Or, you know, which things are about to do? What making it spectacular, making it something that making it relatable?


Douglas Squirrel  08:21

Yeah, that’s new. So I encountered a book called Million Dollar Consulting. Then the reason I said that I, you know, is aiming for a million dollars was was partly due to the title of that book. And this guy, Alan Weiss, who wrote the book and has a lot of other material as well, his who really got me started thinking about how to become as, as notable and dramatic as, as I’ve managed to do. So I credit him with, with that inspiration. So it was a conscious choice. And in particular, one of the constant directions that I chose, after about the first year or so of, of working was to make every project as short as possible, how can I make this one shorter? How can I make it faster? How can I get there, the results in a much in a dramatically shorter amount of time, because that gives tremendous benefits, right? If you’re able to do the same amount of work in a shorter time, you can do more of it. And the client gets better results faster. So it took me about a year to do my first couple of substantial team rescues team improvements in that model that I described at the beginning. And after five years of doing it, I can typically get one of those projects done in two months. My challenge for this year is to see if I can compact that down to a one day workshop. And can people get that much value or some substantial proportion of it in one or two workshops. And that’s even compressing it still further?


Alastair McDermott  09:47

Yeah, I’m, again, I’m on the same page. So you one of the things that I do is I have a website in a day, which I find that website projects tend to stretch and you know take them months, where, whereas they don’t really need to. If you have all your planning done upfront, you can actually get it done very quickly. So yeah, 100% with you there. Okay, I want to just come back to something that you mentioned earlier, you said the part of what you do is explicitly asking for referrals or explicitly asking for, for new business. You talk a little bit about how you do that. And, like, how can you do that? How can you approach that in a way that doesn’t feel like you’re kind of begging people for for business?


Douglas Squirrel  10:30

Hmm. So I don’t do it as well as I would like. So I would like to be more disciplined about that and more aggressive about asking for referrals. One reason I haven’t done it as much is that I get a lot of these current sort of organic referrals where people go down the pub and say, Oh, you’re having this problem, talk to a Squirrel. So I haven’t had to push it. But I think I probably should do more. What I do religiously, with every client is to say, Would you like to, would you mind if I put your logo on my website? So there’s a big client list now and I’ve worked with over 100 different organisations, and a good proportion of them have said, Yes, of course, some say, don’t tell us. We don’t tell anybody you know, we’re secret. We’re in stealth mode, so that I can’t list everybody. But a good proportion of those are on the my clients page at And I ask always, can I put your logo there, and almost everyone says, ‘Yes,’ I asked for testimonials, in many cases, especially where someone is in a new area or in a new direction for me, so I’m going to be asking for that local business that’s family owned, I’m certainly going to be looking for a testimonial there so that people can see the breadth of what I do when they go to my website.  And that’s about as much as I asked for today. The exception is sometimes someone will be particularly well connected. And I will ask them to talk about me at an event that they might go to or in a forum or in a group that they are a part of. And again, they’re in this tight knit community of startups, there’s lots of those. There’s, and sometimes like my San Francisco client, I just was asking last week, can you introduce me to some other people in your area? Who are in San Francisco are in your industry? And the founder said, Oh, well, yeah, actually, I do some angel investing. There’s some folks that I invest in, who should probably use you, then that’s going to hopefully do more San Franciscans in my in my portfolio, which I think will be helpful to broaden that network. But what I don’t do and probably should, is with every client say, Great, can you give me three people that I should talk to? Can you give me give me their email, you know, can you make an introduction? Can I phone them? If I were really in aggressive mode, if I were looking for as much new business as I could find, then that’s what I would be doing. I just haven’t needed to the organic referrals have been enough?


Alastair McDermott  12:47

Right, right. Okay, so one of the things that you do is you try and make the projects as short as possible. They’re inherently valuable projects already, because they are transformative. So so people are willing to pay a lot for them. Are there anymore?


Douglas Squirrel  13:07

Not necessarily. So not everyone is. So one thing to qualify, of course, is whether people are actually see the transformation as valuable enough, right? And there’s always folks who are coming along and saying, well, gosh, you know, if I work out your hourly rate, that’s a high number. And I say, yeah, and that’s good thing, right? You pay more to get a package someplace faster. And you don’t calculate, you know, how many hours are you paying for of the postal person, you know, delivering your package to get there tomorrow instead of next week? You you pay for getting the package there quickly, because that’s a value to you. Not everyone buys that. So so some folks do not value it highly enough. And that’s good, because I don’t want to work with them. Yeah, I want them to go find a cheaper alternative, which is probably better for them. Definitely better for me.


Alastair McDermott  13:48

Yeah. So I know that one of our Alan Weiss books is about value pricing. Have you read that one? Have you integrated that into your your processes and your pricing?


Douglas Squirrel  13:59

Absolutely. I never charge a day rate. I think it’s unethical as as Ireland does, right. So when people say, what’s your day rate? I say, I never work that way. And I don’t I never want to again, because then I have to have a stupid conversation. Oh, you know, actually, you need another day. And that’s gonna cost you this much more. Do you want to pay that much more? That’s just a dumb conversation and unethical because it gives me the motivation to go slower. Why would I want to go slower? That doesn’t help my client that doesn’t help me. So I’m consistent in only charging a fixed rate. And then that has given me that’s something that has driven me to think up, how can I get to this result faster? How can I work even more efficiently.  In fact, when the pandemic hit, that was an opportunity, in fact, not a welcome opportunity. Obviously, we didn’t want it to hit but it’s an opportunity for me to stay here in my 600 year old house in in folkston. And to work with many different folks in the same day and therefore be more efficient. And if I hadn’t had that motivation that I might have said to myself, my gosh, my business is going to crater All of a sudden, I don’t have travelled time and expenses and going to see everyone and the you know, I’ll be more efficient. And that will be bad because I’ll charge less. Because my hourly rate, I’ll have fewer hours, and I’ll be more efficient. And that’ll be bad for my business. Yeah. And that just does my head. And I can’t understand why anyone would want to work that way. So after, after reading Weiss’s first, the first book of his I read The Million Dollar Consulting, I stopped and have never charged today rate since.


Alastair McDermott  15:28

Yeah. And just as a side note, for anybody listening to this, I also recommend checking out Jonathan Stark and Blair ends. I’ll put some links to the show notes to both of those. Yeah. Okay. So so you


Douglas Squirrel  15:41

May have heard more message in a very good one.


Alastair McDermott  15:43

Yeah, yeah, absolutely. So I’m just just trying to figure things out a bit, getting to $1 million a year here, I see you’re making your projects as short as possible. You’re doing fixed base pricing that’s totally disconnected from from your daily rates. You’re increasing your prices frequently. You have built up a reputation within a very tight knit community, and who are founders of tech startups who you’re able to deliver a big transformation for? Are there any other pieces of the puzzle there?


Douglas Squirrel  16:16

I think just to colour one of them, the efficiency is very important. So the squirrel phone I mentioned before is an evolution. So I noticed people would phone me, and I noticed that I could help them very fast. Then I said, Maybe I should do something with that the fact that people are phoning me means that there’s a demand for filming. And I don’t mind it. And in fact, I can help them very quickly. And if I tell them, I wonder if people will abuse it. You know, I wonder to myself, if I tell people just filming when you need me? Will I get 20 phone calls a day? The answer is no. The answer is no one has ever abused it in 10s of clients who have had access to it. And so now it’s a standard component of my practice. So it’s looking for those kinds of efficiencies that have helped me to help even more clients. So you know, I helped two or three in the first year it was I didn’t even count last year, it might have been 30 or 40. So that’s increasing the number that I can work with at the same time by being more efficient. And that also helps to get to the increased income and increased help for more people.


Alastair McDermott  17:18

Fantastic. Okay. Is there any recurring revenue there in terms of retainers for for phone access? Or is that just paid one off? How does that work?


Douglas Squirrel  17:27

Now, now, this is something my co author is always bugging me about. I wrote a book called agile conversations, you can find it on Douglas scroll, calm and elsewhere. And I wrote it with a co author who’s kind of putting his toe in the water to do consulting. And I tried to encourage him not to make mistakes, I didn’t, didn’t charge a fixed rate and so on. He’s very receptive to that. But the thing he’s always bugging me about, I think he’s right about is that I’m missing the second and third and fourth sale. So I should be, this is actually a perfect reminder, because I’m for that client I was talking to this morning, I need to write a proposal tomorrow. So I’m going to include I’m telling the world now, I’m going to include a option for ongoing retainer work in the proposal, which I should do in all of them. I don’t always Yeah, so I should do that better. I do have clients who continue, they’ll often have a transformation project, and then continue with the squirrel phone for a quarter or two afterwards, to help make sure that the changes stick. And I should do more of that because of course, it’s much easier sale. They already know me. And that’s exactly what this client I was talking to this morning, is they had me do a small piece of work in December originally. And then they came came back and said now you made some recommendations, can you help us make those happen? So I should do a lot more of it. And it would help me more to do more. I’m going to be working on that.


Alastair McDermott  18:45

Okay, so we’re using the word transform and transformation a lot. I know that you’re that the book agile conversations, you have a subtitle transforming conversations, transform your culture. And by the way, Jack’s word


Douglas Squirrel  18:58

I think it’s terrible.


Alastair McDermott  19:00

What’s so hard to


Douglas Squirrel  19:01

The transformation just is so meaningless that people season so we should talk more about it. So yeah, yeah, absolutely. Anyway, he started to say something about like, Oh, God.


Alastair McDermott  19:08

Yeah, he wrote this with Geoffrey Frederick. Yeah.


Douglas Squirrel  19:11

Yeah, that’s right.


Alastair McDermott  19:12

Okay. And is Jeffrey, somebody you’ve been working with for a while? How do you know, Jeffrey?


Douglas Squirrel  19:17

Oh, yeah. 12 years. I hired him. And then he replaced me at a startup I was working in and he’s now the managing director of that startup. And we’ve been working together practising doing a lot of the things that are in the book that improving your conversations in order to improve your team. We’ve been doing that stuff together for 10 years or more.


Alastair McDermott  19:37

Right. Okay. And so, are you are you looking at this as applied to organisations as a whole, or is this specifically around software teams, people like that.


Douglas Squirrel  19:49

So what we did is we took a practice an academic theory called action science which was developed in the six 60s and 70s and 80s by a guy named Chris Arduous, and then developed further by his students in following years. So it’s an old method, which is very, very helpful for in a in any organisation understanding what conversations are key to improvement, and how those conversation can improve. We always say that you, everybody has conversations all the time. But nobody really thinks about improving your conversations as a skill. So that’s the kind of general theory and through a circuitous route in a very smart guy named Benjamin Mitchell, both Jeffrey and I encountered these ideas. And we said, these would be perfect to use in our environment in the environment of tech startups and engineering teams and folks like that, because what it does is it actually takes a complex area of human communication. And it gives you a set of tools and rules which you can follow. And engineers love that, right. as engineers, we think it’s great if you can tell us step one, step two, step three, if we do this, then go to Step 12. Like, we love that, we eat that stuff up. And that’s what this gives you. And one of the biggest challenges that we have in all the adoption of agile methods, and DevOps and lean startups and all this other kind of stuff, all these buzzwords, and so on.  There’s lots of consultants and others that you can hire who will come and make your organisation work in these ways. But what they don’t tend to do is to improve what everyone says goes wrong, which is the underlying culture and the underlying conversations among the people in the organisation, they start to do the actions but they don’t actually make the the cultural and mental shift that’s needed in order to make whatever it is they’re trying to do work. And so the book is all about how to use these action science ideas, as a template as a tool for applying them to make your transformation work in a typical in the book is all about how you can make it work in a technical environment, where as I was saying, before, I’ve branched out all over the place. So I’m coaching salespeople, and helping founders with their investor problems. And I’ve got one group where their their three founders, all of whom are battling each other, and, you know, helping them to work together better. And it’s not tech focused, as I applied in my practice, necessarily, although that’s where I come from. So that’s what I tend to do most. And the book is about how to apply it in those circumstances. But it’s much more general than that.


Alastair McDermott  22:27

Right, right. Fascinating. Okay…


Douglas Squirrel  22:31

By the way, we didn’t mention we didn’t mention when we’re talking about Marketing for Consultants. One reason for writing the book was to get more business. And it didn’t ask me whether that worked.


Alastair McDermott  22:41

Yeah, okay. Well, let’s talk about that. How has the book worked for you in terms of marketing?


Douglas Squirrel  22:47

Not very well. So it’s, it’s okay. And in fact, Jeffrey and I did one two hour workshop, that earned us more than all the royalties that we got combined from the book so far for, yeah, six, eight months of sales, so that that alone was worth it. So that’s perfectly fine. But directly, it has not led to sales. And I think there’s some mistakes we made, there’s some things we could have done better that I hope to do better. In the next book, talking to the publisher next week, the proposal is out, we’ll see if we, if we can get that in press soon. So there’s some things we could have done better. And there’s some expectations we have that probably weren’t realistic.  So there was some things that we could have done better, or to tie bits of the book, to actions that you can take. So we just wrote a book that had as much information as we could in it, and people have found it valuable. And that’s great. But the book doesn’t have drivers that help you go find out more, engage with us, have us help you. And that’s in retrospect, kind of dumb. Because the book is founded on certain practices that you can follow, you take a piece of paper, you fold it in half, you write down bits of your conversation, these are all these 123 steps that the engineers love. And that really helped them. And that’s fantastic. But we taught people how to do and we didn’t say and by the way, you can come and practice with us go to this website, you know, come and talk to us. We do these practices all the time, you can learn more. And if we done that, and I think we would be driving more people with books, I’m not going to make that mistake again, right future books will have more drivers. And then the other thing is that it doesn’t help that there’s a pandemic, but it it tends to be that books are much broader in their audience, and they don’t tend to drive as much action as I might have thought.  So especially when it’s commercially published, what you get is credibility. And I’m sure it’s helping indirectly in my work. In my in my marketing to have people say, Oh, well, he’s written a book, and I could go read the book. Oh, good. You know, I’ve read the first chapter. Good. This guy knows what he’s talking about. Let’s phone him. So it’s giving that level of credibility, the same as a website. My website is not something that people find on Google very often, but they hear about me down the pub and they said, I wonder who’s is there really a guy named Squirrel? Well, look at that. There’s a guy named Squirrel. I’ve never knew he actually has worked. I’ve looked at all these clients, I should talk to them. book does the same kind of thing. It’s a credibility enhancer.  And of course, I had expected that I’d be handing it out over the place, I have a stack of them under my desk here. And I thought, Oh, yeah, I’ll be handing these out, you know, everybody will get one, I’ll sign them all the time. Well, that didn’t happen, because nobody’s seeing each other. Right. Once that once that diminishes, then I will be handing them out. Even more, I’m sure. And that will help it but really, for credibility, really, for people know it once they already know me sort of saying, Okay, he’s, he’s for real. And I think I had some unrealistic expectations about how much we would actually get from people directly saying, Oh, I read this book. Now I need to get in touch with the author. We didn’t connect that for them. And I think we had an unrealistic expectation about it.


Alastair McDermott  25:46



Douglas Squirrel  25:47

But nevertheless, I’m very glad to have written it and starting on the second one now,


Alastair McDermott  25:50

Yeah. Okay. The so I’m interested, the decision to go because I mean, these days, we really do have a choice to go self published, or to to work with a publishing company. Was it the lack of hassle? Or was it the credibility factor that that brought you?


Douglas Squirrel  26:09

I have more hassle with the commercial publishers? Seeing the battles we have? Yeah, there was one, one debate over whether there when I said, folding the paper, whether you should have the certain bits of the writing on the left hand side of the right hand side, I can’t tell you how much argument we had over which way we should put it in the book. So we would have had none of that had we published ourselves. But we wouldn’t have had the distribution to new areas. So no part of my marketing activity with being with you, as I said, is to talk to new people who’ve never heard of me before, and might come along to my podcast, or read the book or something. And then they’ll know me and refer me to their friends that, that that is something is also happening from the book, because it goes well on at least virtual bookshelves and people find it and then they read it. And we’re about to get reviewed by the Standish group, and I think they’re famous. So I think a lot of people will find it there. And then they’ll say, they’ll know about me and Jeffrey, and that will be helpful. So it helps in in getting to new audiences.


Alastair McDermott  27:07

Okay, and so, I’m interested well, so you’re, you’re planning to write a second book, what are you going to change with the second book in how you approach us as a project?


Douglas Squirrel  27:18

Well, the main thing is, is what I was saying before, which is getting as many hooks into the book as possible as the commercial publisher, let me get away with I can’t have on every page and phone me today. You know, here’s my number in big, bold, flashing text, then that would be spammy and explicit marketing that wouldn’t match my brand. So I wouldn’t do that anyway. But in weiss’s is remarkably good at this. So if I can do half of what he does, I’ll be very happy. If I can fit in references that really do fit the topic of the book two opportunities to practice opportunities to learn more kinds of ways that I’ve helped clients. So the people who read it think, ah, this is a person not only who’s written a book, and who has a funny name, but is somebody who I can pick up the phone to and get some help from, if I if it’s on my aiming to include a lot more of that in the forthcoming book.


Alastair McDermott  28:14

Right. Okay. Do you have a an email list?


Douglas Squirrel  28:18

Yes, but don’t use it as well as I could. So Jeffrey, and I started one, again, thinking we’d get a whole lot of people kind of coming to our website, that website, if people want to check it out is conversational transformation, calm, agile conversations, calm also works. But we had to buy it after the book went to press, because we were trying to find the person who owned it. So we bought the other one, they both go to the same place. And there’s a mailing list on there. And there’s a standard thing, you get a video of us, teaching you about one of the topics in the book, if you sign up to the mailing list. And we have a small group there, and we just made a mailing to them yesterday, or co author. I ignored him completely while he was setting one up, and Jeffrey went off and sent it off. And I’m very glad he did, because I was busy with other things. But that’s the level of attention that we’ve paid to the mailing list. So far, we have not aggressively around it. There’s something like three or 400 people on it. We’re mailing that when we kind of have an event or something that we think of, but we have not gone after it with any aggression at all. I think that’s probably especially if I want to move to this workshop model, where I’m doing the same kind of thing I do in two months and previously in a year, and I get that compressed down into a day or two. That’s the kind of thing I’m going to need to do much more of, but right now I don’t do much.


Alastair McDermott  29:36

Okay, excellent. So, alright, let’s see. Okay, so one thing that I’m always interested in hearing stories about our how people have failed and what they’ve learned from that. Do you have any any examples or something you did that that kind of failed or failed spectacularly? What what did you learn from that in your business?


Douglas Squirrel  30:00

I don’t know if I have any marketing spectacular fails, because I just don’t do very much marketing. That nothing that’s very explicitly marketing? Um, well, there are a couple. So, Jeffrey and I did a lot of promotion for the book. And I think now having gone through, I’m very glad to have learnt from it. And I think I know better, what kinds of things to pay attention to, and which not. And I did well, actually, no, I do have a good failure story. So out of that, one thing that I tried to do, which just really didn’t get very far, was to individually target people who commented on the book and tweeted about it and LinkedIn posted, which that’s got a verb and about it, and so on whatever they did. And some of them turned into something successful. So one of them turned into that project, or we did a two-hour dojo session is what we call it. And we did a practice session with a company and that’s likely to lead to more work with that company. And that’s good. So that was a targeted approach. Somebody responded to a LinkedIn post, I said, Hey, you look interesting. Can we talk to you, and six months later, it was it was a slow burn. But we eventually got to a sale there. But that wasn’t terribly efficient, wasn’t like I published the book, and then the phone started ringing. It was it was a hard grind. And there were a lot of people I was getting in touch with many of whom didn’t respond, and some of which just really didn’t mean much, that didn’t lead to very much at all.  So I’d say that’s not maybe not a spectacular failure. But it’s a notable failure, that I thought that investing that time and energy in individually targeting people who commented on the book would be successful, it really wasn’t, and still haven’t quite understood exactly why that is. But my suspicion is, again, that they they’re not kind of the motivated buyer ready to go. I haven’t given them a lot of opportunities to interact with me and get to know me and, and work with me on another area that I am thinking of intimacy and connecting with people is, I have done some and again, I haven’t invested a lot in this. I think if I did more, I would do better. I hold office hours periodically, kind of when I feel like it or when I have a question that I think I can help people with. And I’ll invite somebody on who’s asked me a question. And I’ll answer that question publicly, and help out that person. And I live stream it on Facebook and YouTube, I do it on LinkedIn if they’d let me in, but for some reason they haven’t approved me. And I get a few viewers. But you know, it’s mostly friends. It’s mostly people who already know me, it hasn’t led to any sales. I also haven’t invested very much in it. But I really think there’s a lot of benefit from that I think used well, that kind of thing can create that feeling of intimacy where somebody says, ‘Well, yeah, I know this guy. I mean, I read his book,’ and I went to his live stream, and you know, I should go to his workshop. Yeah, that’s on Thursday. I’m gonna go sign up. I think that’s true, but I haven’t validated that yet. So there are two failures. I’m trying to individually target folks and live streaming. But I think at least the live streaming has legs for the future.


Alastair McDermott  33:00

Yeah, absolutely. I did my own live streaming experiment in November, where I did a live stream every day. And I found it very useful. Did that work out? In terms of allowing me to create a lot of content very quickly, it was very useful. And also, what it did is it reminded me of the accelerated effect of doing something daily. When you do something daily, as opposed to weekly or monthly, you just you improve as you get much better. And, and…


Douglas Squirrel  33:30

People come to expect it? I mean, that’s one problem with my live streaming is I kind of do it when I feel like it. And I promote it beforehand when I’ve decided to do it. But it’s not that somebody can set their calendar and say, okay, it’s four o’clock time for squirrels live stream this week.


Alastair McDermott  33:42

Yeah, yeah, absolutely. Yeah. So in fact, it’s one of the things that that has caused me to think about doing this podcast, releasing twice a week, as opposed to once a week, just that accelerated effect. By the end of the year, I’ll have 100 episodes as opposed to 50 episodes. So yeah. That that accelerated effect to think of the daily thing was was very good. And live streaming, I think as a, as a, as a platform. I think it’s good because it gives people you tend to be a little bit more raw. It’s live, it’s on attitudes, and it tends to be a bit more behind the scenes. So it’s a bit more intimate, I think, so allows people to have a kind of a more of a connection with you. So yeah, that is definitely an


Douglas Squirrel  34:26

Intimacy is important. And we’re already finding that with our podcast, we’re on episode 153, or something like that. And again, we haven’t exploited it to the degree that we probably could, but we we’ve got a consistent, you know, 1000s of listens every every month, Jeffrey likes to remind me, I never remember what the number is. But we’ve got consistent people listening to us who get to know us and for example, the guy who bought the the the two hour dojo listens to us on his run every day. And the consistency of coming out every week has been very, very helpful.


Alastair McDermott  35:00

Right. Okay, and can you tell us where to find the podcast?


Douglas Squirrel  35:03

Oh, sure. Sorry. That’s Troubleshooting Agile, you can find that again on the or probably easiest if people are on their own runs is have a look for or


Alastair McDermott  35:16

Super. Okay. I have a question like to ask people. Can you give me a breakdown of how many hours you spend on marketing or sales related activities compared to actual project delivery and things like that?


Douglas Squirrel  35:33

So explicit marketing, zero. I mean, I really spend nothing on on anything that I’m explicitly explicitly thinking myself, this is a marketing activity only. This is the only thing I’m doing. I’m just trying to get more people. I expect to change that, as I start to do the workshops, because I’m thinking I’m going to need to broaden that. So actually, learning for me this coming quarter is gonna be how do I do that? Do I write daily to my mailing list? Should I do daily live streams? Like Alastair did? I’m not sure. So I’m What?


Alastair McDermott  36:04

Did you consider that marketing at the time you were doing it?


Douglas Squirrel  36:07

Um, it had a marketing purpose. But But I would define it differently. I would say there’s a lot of things that I do that increase visibility, generally, that I’m not doing them with the mindset, how am I going to measure the success of this by the number of people who sign up to my mailing list? Or the number of people who attend my next live stream or something like Yeah, yeah, I got likely to think that wasn’t my thinking. My thinking was, how can I get a book out? So that when I go on a sales call different from marketing, when I go on a sales call, somebody said, Oh, yeah, I bought your book. And that that does happen.


Alastair McDermott  36:40



Douglas Squirrel  36:40

And that person says, okay, you know, my team’s read your book, or we’ve had a look at that. Or I’m, I see you have a book, haven’t read it. I don’t care whether they read or not. Yeah, I’m not at all fussed at my publisher cares a lot about making various sales figures, I don’t care at all. I just want people to know there’s a book. And if they read it, that’s great. If they just know I have a book on a topic that’s relevant to them, and it’s from a commercial publisher giving it credence, and that’s good enough for me. So I didn’t think of any of those as explicitly marketing. You did say also how much on sales and there’s a fair amount on that. So that’s the organic references coming in. And occasional visibility, increasing activities like being on this podcast or being talking to you know, later this month, I’m talking to a group of CFOs about how to talk to your tech team then how to detect baloney. So that that kind of activity this week, Jeffery, right, and I are on a, an agile meetup in Salt Lake City of all places. So we’re staying up a little late in the UK and getting on a meetup in Salt Lake City to talk about our book and what we do. So I’d see those not as explicitly marketing, but as increasing visibility and increasing sales credibility. Maybe that’s a distinction without a difference. I’m not


Alastair McDermott  37:55

Yeah, yeah. Yeah. Interesting. I mean, personally, I would see some of that, like, the lines are very blurred. But some people will see that as content marketing and networking. So yeah, it’s it’s it, I guess, it depends on on your view, and it could just be semantics. So. Okay, so something else I’m always interested in it. Do you have a favourite business book?


Douglas Squirrel  38:17

Favourite business book? Goodness, I don’t like very many business books. So that’s a good puzzle. Let me think for a second that the fact that I have to think suggests that maybe I don’t have one. Crossing the Chasm is pretty good, has a lot of good information in it. See, I tend to think of books more when I need them. When when they they solve a problem that I have in front of me sort of generically, what’s a good book that’s generally about business? Not sure there are many that are that are good in general in that way.


Alastair McDermott  38:50

Okay, and in terms of nonfiction, sorry, in terms of fiction, what’s your favourite fiction book?


Douglas Squirrel  38:57

Oh, goodness. Well, the ones I read most recently that I really liked, were the and I’m gonna remember that titles wrong there by a Chinese author. And she, he sorry, writes about future society that encounters aliens, and I’m trying to I’m sorry, I’m just chattering while I try to remember what it’s called. But one of them is called the Dark Forest. And I think it’s called it’s called the Dark Forest Trilogy. That’s the way I can I can put it is that yes, the Dark Forest Trilogy


Alastair McDermott  39:27

Is it The Three Body Problem?


Douglas Squirrel  39:29

The Three Body Problem? I couldn’t remember that. Thank you, Alastair. Yep. So the Three Body Problems the first book, the trilogy is called the Dark Forest. I found that entertaining.


Alastair McDermott  39:38

Okay, cool. Yeah. Interesting. Yeah, I’m a big science fiction fan myself, so I’m gonna put that on my list. Super. Okay. Is there anything else that you want me to ask you about?


Douglas Squirrel  39:53

I never answered that question, because I never know quite what to help people with. So yeah, I think you’ve asked me all kinds of great questions. I don’t have anything to add other than you don’t have to do as much marketing as you think you do. Because I’ve done various things, as I was saying in my failure, yeah, list the various things that really haven’t produced much the main thing that is produced really stellar results, is doing tremendous work, letting people know about it and making sure they know where they can find me. And I’d love to talk to any of your listeners who are interested in chatting more about how I market or how I do this. I’ve had occasional coaching clients who want advice on this so they are welcome to get in touch with me on that. Or just to chat to me or to refer me to some one of their friends if they feel like doing that. And you can find all my information everything about me at


Alastair McDermott  40:41

Okay, well, thank you so much for being with me here today. Toggle squirrel calm, and the book is agile conversations. And the podcast is


Douglas Squirrel  40:51

Troubleshooting Agile


Alastair McDermott  40:53

Troubleshooting Agile. Douglas, thank you so much for being with us today. I really appreciate your time.


Douglas Squirrel  40:58

Glad to be here. Thanks, Alastair.


Alastair McDermott  41:03

So that was Douglas Squirrel, and I love how nonchalantly he talks about having a million dollar consulting business. It’s really an inspiration. Thank you for listening. If you get any insights or tips from the episode, please share it. It might just be the thing that helps somebody else in your network. And if you share the show notes link it will include a podcast player and all the other information from today’s episode. See you in the next one.