Be More Pirate by Sam Conniff Allende | with guest Spencer Gallagher

25 May 2026 · 35 min · 15 chapters

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In short

Using Be More Pirate (Sam Conniff) as a “modern rebel” playbook: build a fear-inducing reputation (Blackbeard/Jolly Roger), avoid mediocrity with authentic, ethical marketing “fame projects,” reinvent the status quo with boundary-pushing (pirate radio, Napster/iTunes parallels), and flatten hierarchies to create ownership and accountability.

Guest backgrounds

Spencer Gallagher, 27-built Blue Halo to ~£12M revenue, exited to Gyro; author of Agencynomics; now runs an AI-first M&A advisory company also called Blue Halo. Former web developer; scales/future-proofs agencies.

Key claims

Pirates were “smart” and avoided fights via reputation; pirates pioneered insurance, equal pay, flat structures, and even same-sex marriage norms. In business, “brand is what people say when you’re not in the room.” Quarterly fame projects beat perfectionism; AI enables autonomous agents for repetitive admin (e.g., NDAs).

Notable examples

Blackbeard’s brand fear; rum + medicinal herbs to prevent scurvy; ice-cream van with branded Soviet napkins; locked Amazon sweets with passcodes; Companies House “robot” letters; pirate radio forcing BBC to launch stations; OpenAI acquisition of OpenClaw; AI orchestrator Tabitha generating NDAs.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Introducing Be More Pirate

0:45 to 2:00

Discussion on the book 'Be More Pirate' and its relevance for modern entrepreneurs.

“At 27, Spencer built Blue Halo into a£12 million revenue powerhouse before exiting to gyro.”

The Concept of Reputation

2:00 to 4:00

Spencer explains the importance of reputation and storytelling in business.

“What does it mean in the book about building reputation?”

Pirates as Pioneers

4:00 to 6:00

Exploration of how pirates were ahead of their time in various practices.

“Do you just want to touch on a couple of those things?”

Avoiding Mediocrity in Business

6:00 to 8:00

Tips on how businesses can stand out and avoid conformity.

“And I was with a client yesterday and they've got a particular target company they want to work with.”

Creative Marketing Approaches

8:00 to 10:00

Examples of creative marketing tactics that can set a business apart.

“So I think it's important that you have an ethical code underneath all of this.”

Authenticity and Integrity

10:00 to 12:00

The importance of authenticity and integrity in business practices.

“So the first letter that any company got between 2003 and 2002 and 2005 was basically from us.”

Reinventing the Status Quo

12:00 to 14:00

Discussion on how pirates challenged traditional business structures.

“Sometimes you have to challenge the status quo.”

The Evolution of Innovation

14:01 to 15:50

Discusses how new innovations push boundaries and create opportunities.

“that actually all new things start the same way.”

Embracing AI in Business Strategies

15:51 to 17:43

Explores the importance of integrating AI technologies in business models.

“But I think there is an ocean of opportunities right now for all of us to be a little bit more pirate.”

Navigating the Now, Next, and Future Framework

17:44 to 21:20

Describes the framework for understanding current trends and future opportunities in business.

“that you can future-proof their lives or their business, depending on what your company.”
Show all 15 chapters

Lessons from Pirate Crew Structures

21:21 to 23:28

Analyzes the benefits of a flat organizational structure inspired by pirate crews.

“One thing I do want to just double click into a little bit is the Now Next and Future framework.”

Building Individual and Collective Responsibility

23:29 to 28:00

Discusses how individual roles contribute to team success in a flat structure.

“Credit card companies wouldn't allow it.”

Empowerment through Meritocracy

28:00 to 29:59

Learn how flat organizational structures foster individual growth and value.

“It's all about building individual and collective responsibility, accountability, but without this need of saying, where do I go next?”

Equity Distribution and Business Growth

30:00 to 31:39

Understand the implications of equity distribution in growing companies.

“The Navy needed to have that really hierarchical structure to make it actually possible to function globally.”

Employee Ownership Trusts Explained

31:40 to 33:29

Explore the concept of employee ownership trusts and their benefits.

“My personal belief is that really you should probably do some kind of performance bonuses in the early years because let's just do the numbers here quickly.”
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Transcript

Automatic transcript. May contain errors.

0:01Sam Conniff Allende:Welcome to Business Book Club, the show where top entrepreneurs break down the most powerful insights from the world's best business books. I'm your host Sam Brown and today we're talking about Be More Pirate by Sam Conniff.

0:17Sam Conniff Allende:In the next 30 minutes, you'll learn why the most successful founders don't follow the rules, they rewrite them. If you feel like you're constantly fighting the way things have always been done, this episode is your permission slip to stop. Be More Pirate is positioned as the manifesto for the modern rebel. Sam Conniff didn't just write this, he lived it. Founding Liberty, an award-winning creative network that proved purpose-led disruption can scale. And joining me is a man who knows exactly what it takes to scale and exit at the highest level. Spencer Gallagher. At 27, Spencer built Blue Halo into a£12 million revenue powerhouse before exiting to gyro.

0:55Sam Conniff Allende:He's the man behind Agencynomics, a book that gave me the financial framework to scale my own agency with confidence. I may well do a solo episode on Agencynomics when I somehow find the time. And now he's back at the helm of an AI-first M &A advisory company, also called Blue Halo. Today, Spencer is breaking down why a book about 18th century pirates is actually the ultimate guide to 21st century agility, culture building, and systemic change. Spencer, thanks for being here. Why did you choose Be More Pirate as the most impactful book that

1:28Spencer Gallagher:you've read? I chose the book because I think it's one of those books that really gets you thinking about avoiding mediocrity. I think in life it's very easy, especially in this new world of AI, to settle for the average of everything. And I think in business, sometimes we have to take a step back and we have to think about things a little bit more creatively and a little a bit more innovatively. I'm excited to get into these lessons that you've brought.

1:56Sam Conniff Allende:Build reputation, not mediocrity. Let's dive into the reputation bit first. What does it mean in the book about building reputation?

2:05Spencer Gallagher:Blackbeard is probably a wonderful example of this. To be really clear here, by the way, this book is covering the golden era of 17th and 18th century pirates. What was very interesting about people like Blackbeard was they would go around on their ships. Of course, they were looting and stealing, so they weren't particularly all good, but they were challenging authority, but they were all doing it under this pirate flag. And the pirate flag, a lot of people thought that pirates went around fighting all the time, but they weren't stupid pirates. They wanted to stay alive and make money. Reputation was really important for them.

2:38Spencer Gallagher:Reputation was all about how can they create a reputation that makes people fearful of them, so they don't attack them, so they don't fight them, so that actually they were left alone. One of the stories from the book is very much around Blackbeard saying they actually don't even know whether he did get involved in any fighting at all because everyone was so scared of him. His personal brand, his stories that were created of him being this massive tyrant just scared everyone away. And so the reputation in today's world might translate into something like the brand for your business or the brand for you as an individual.

3:10Spencer Gallagher:But it's often the storytelling side of your business. What do they say about a brand? Brand is what people say about you when you're not in the room. And I guess it's the same with the personal brand too.

3:22Sam Conniff Allende:They talk about it in the book quite a bit about the pirates being the world's first super brand and the logo of the Jolly Roger. All the pirates, they had their own version of the Jolly Roger, but they all had very similar themes, all the black background and some similar iconography. If you see this Jolly Roger on the horizon, you would feel the fear from all of these stories that were told. So yeah, the world's first super brand. It was over 150 years before Coca-Cola even existed, which is often cited as the world's actual first super brand.

3:50Spencer Gallagher:Yeah, I think when we go on through this podcast, you'll actually see that pirates pioneered and invented a lot of things many hundreds of years ahead of today's society. They really were the pioneers. Do you just want to touch on a couple of those things? Yeah. So pirates invented cocktails. So obviously they were known for the rum, but the scurvy was rife back then. So they would make a concoction of rum and other medicinal herbs that would help prevent scurvy, obviously vitamin C driven. They also are very progressive in terms of same-sex marriage. They had no issues with same-sex marriage, talking 17th, 18th century.

4:29Spencer Gallagher:They had flat organizational structures. They were very progressive in the way that they had insurance policies against injuries. If some people got injured, they had equal pay. These are all things that we're here fighting about in today's world. Everybody got paid a set amount and then the bosses only got paid a fixed amount. They got paid double what everybody else got paid, but it was fixed. That's just some of the things that they pioneered.

4:55Sam Conniff Allende:You were touching on a minute ago around building the reputation that actually pirates, they do want to avoid battles. They don't actually want to engage in actual fights because, you know, one reason is this insurance policy. If someone dies or loses a leg, they have to pay out to the family or to the individual. So they embellish their stories and use this flag as a symbol. Let's move on to this not mediocrity element of it. How does that come into play?

5:19Spencer Gallagher:It's very easy in this world to not set yourself apart in any shape or form, especially in business. It's very easy to conform. And conformity can be very dull. If you as a business want to stand out, being mediocre is not the way forwards. So it's about thinking about with your business, how will you stand out from the crowds? How will you build your brands and your company brand, your personal brands? What can you do in your marketing, your advertising, your PR, innovation in your business? What can you do that will build stories that will excite people about your business? And I think that's really the context that I'm trying to get across here is challenging business owners to just take a step back from their business a few times a year and ask yourself, what could you do differently?

6:10Spencer Gallagher:And I was with a client yesterday and they've got a particular target company they want to work with. they've already planning to send in an ice cream van to the offices or that company to give away free ice creams to anyone who works there with branded Soviet napkins to go with it. And also even possibly saying, do you know this person wanted, you know, to talk to and just thinking of funny things. And I've got hundreds of stories like that. I mean, there's a great one with one agency in the north of England who sent out boxes of locked sweets from Amazon. You can get passcoded boxes and then sent it into marketing teams and said, if you want the suites, call my mobile and I'll give you the code number.

6:50Spencer Gallagher:So it's like, how can you apply interesting different approaches to make your brand seem more exciting? Because if you do things like that, then people's perception of your brand is, well, look, aren't you fun? Aren't you going to be good to work with? So there's just a couple of examples there.

7:06Sam Conniff Allende:This standing out thing, it's a great idea when you have these stories of this is what X company and Y company are doing, they sound good. But have you got any tips of how people can get into that frame of mind of coming up with those ideas? For me, it's about authenticity.

7:19Spencer Gallagher:When I was an employee, the people I worked for who were the entrepreneurs, they really inspired me with how they tackled these things. I saw so many wonderful examples of what I'm talking about now. But the biggest thing is, is trying to keep the integrity with it. Like it's one thing to create these stories, but obviously trying to have integrity, watching out for spin and bravado. Don't do things that are lies. There's an ethical side to this. I want to just add in, don't go around saying that you do things you can't do because things will catch up with you. And I think we have been guilty in business.

7:53Spencer Gallagher:I think even now you see it on Instagram of huge amount of false claims all the time by advertisers outside of guidelines about what things to do. So I think it's important that you have an ethical code underneath all of this. So in my day job now, I'm either helping businesses scale up or helping them buy businesses or sell businesses. And then probably the last third chance of my job is to help them reinvent their business and keep them future proof. And so when I'm working with clients to future proof them or to help them with their sustainable growth journey, what I'm doing is I'm telling them to do quarterly fame projects.

8:24Spencer Gallagher:So set a small budget aside. And once a quarter, sit down and come up with an idea. whether you're going to break a world record or you're going to do what I just said like you're going to create some kind of publicity stunt or you're going to use technology in a different way to communicate to people you're going to come up with a creative campaign whatever it is set some time aside each quarter try and create four things a year some things will never see the light of day and some things will don't over complicate them and don't be perfectionist with them because building fame is as much about luck as it is about skill.

9:00Spencer Gallagher:So as much as you can come up with some good ideas, whether or not they really take off, you never really know. But you'll learn lessons continually through this. Just to share with you one thing that happened to me. So when I was a struggling up and coming business, I think I was turning over about quarter of a million. You've read agency nomics. So it's the stage where actually I got my non-exec to come in. I was cause for a million. I wasn't paying myself. I was paying my team first and not me. I had eight employees, if anyone's ever been there. And I was building websites right at the beginning of the website boom.

9:31Spencer Gallagher:And he said to me, Spencer, who is it that needs to buy websites? And I was like, well, you know, anyone forming a company needs to buy a website. And he said, well, where do people register companies? And I went, well, Companies House. And he said, well, what if everyone that registered the company in the UK saw a letter from you first before Companies House saying, you've got the company now why don't you get a domain name and a website and a brand to go with it so i went away and we looked up and obviously companies house back then they sold a cd-rom and that cd-rom contained all of the data from last year's company registrations so what we did was went on the website and we realized that they published all of the companies that were registered before they sent a letter out so we wrote a little agent back in the day robot we well ahead of our time, go in every day to Companies House website, and it would take the name of the company, and then it would go to a printer, print a letter out, look up the domain names for that company limited name, and then send it out first class, which would get there about a week before a Companies House letter would get to them.

10:32Spencer Gallagher:So the first letter that any company got between 2003 and 2002 and 2005 was basically from us. And that was a real pirate idea there, because we just thought, how can we do something differently? How can we get to it? What can we do? And we solved that problem. Let's move on to lesson number two. Reinvent the status quo. Tell me a little bit about how pirates reinvented the status quo. I'm not sure if any of your other readers have talked about a book called Reinventing Organizations by Frederick Lallou. So Reinventing Organizations talks about the history of organizational charts. And actually, if you go back in history, it was pretty much the church and the military that originally created the organizational structures that we have today.

11:17Spencer Gallagher:So if you think about the pirates, most of them were ex-Navy. The Royal Navy had very strict hierarchy. They weren't actually offering things like insurance, equal pay. It was a very brutally unfair place to work. And so the pirates pivoted away into this flat organizational structure. They reinvented the way that the ship leadership would work in a way that it would appeal to everyone and to build better crews, to build better teams. And so a good example of reinventing the status quo is not settling for a normal hierarchical business structure, but looking at ways that you could challenge that.

11:55Spencer Gallagher:Just because people do things in a certain way doesn't make it right. Sometimes you have to challenge the status quo.

12:02Sam Conniff Allende:One of the moments where he's talking about this in the book that really hit it on for me was when they were talking about pirate radio. I think he starts one of the chapters actually with the original pirate material song.

12:12Spencer Gallagher:Radio Caroline, Radio Luxembourg were, when I was very young, before BBC One, BBC was playing classical music. Think Radio 4, think the news and the weather shipping forecast. But there was all this pop music. So two separate stations took boats out into the North Sea, just outside of the regulated licensing frequency zones for radio, and broadcasted pop tunes. And actually, it forced the BBC to realise that there was a demand for this. Really, we wouldn't have popular music through BBC if it wasn't for the pirate radio stations of Radio Carolina and Radio Luxembourg.

12:50Sam Conniff Allende:They say in the book that the BBC actually launched, I think, four radio stations within a couple of years and directly in response to this. Yeah.

12:57Spencer Gallagher:And if you look at the other side of things, piracy was a big problem at the end of the 90s. Everyone was ripping CDs onto their MP3 players. And the record industry was losing control of royalties, of money. And then iTunes came in and said, look, we've got a way to fix this. We'll make a regulated platform. They did a deal with all of the music publications. And so they started to find a way to almost reinvent the way that was to stop the pricing. And of course, then Napster came out that people remember Napster and there was file sharing. The MP3 market was clearly a demand. People wanted to carry tunes around with them that wasn't on a radio or a cassette or even a mini disc player back then to be able to have it in digital format.

13:39Spencer Gallagher:But the market hadn't caught up with the demand. And so, yeah, some great examples there of how pirates and pirating has kind of pioneered. In fact, one of the other great books I read over the years is called The Victorian internet. When I first built my agency, it was the beginning of the dot-com boom. And the Victorian internet talked about the telegraph system. And it talked about the fact that actually all new things start the same way. You'll have people having affairs over telegram system. There were people cheating on gambling over the telegraph system. It happens that way. And I think equally, the internet in the early days became this way where it would almost have illicit ways.

14:19Spencer Gallagher:And of course, eventually all systems get regulated.

14:21Sam Conniff Allende:We're not really talking about pirates breaking the law. It's more like pushing the boundaries of what's kind of possible. And then sometimes law has to kind of catch up with it and everything. Which companies do you see that are doing it really well at the moment, pushing these boundaries and reinventing the status quo?

14:34Spencer Gallagher:The biggest one, you know, at time recording this podcast will be OpenClaw. OpenClaw launched the end of January. Everyone's building AI tools or trying to, but there's a huge amount of automation being set up. But a true agentic autonomous automation has been lacking and OpenClaw suddenly builds this framework, which enables you to create agents that are effectively fully autonomous, which sounds quite dangerous. So you have to put certain guardrails up. But now what's happened is because they launched this product and very quickly OpenAI bought them, We're now seeing all of the other AI platforms now releasing their versions or their interpretations of it.

15:14Spencer Gallagher:So again, it's still happening. But actually, I always say to people that the next big thing, the next big company probably doesn't exist right now. If you look at OpenAI, really, it feels like it came from nowhere to be as big as it was. I used to say this line, the Internet's a great leveler. I think today, AI is a great leveler. If you're a small business embracing AI, you're going to be in a better place to compete with a larger company that's got a much larger workforce to evolve, to move, to shift, to train, to educate. So, yeah, I think the next big thing, watch out for it. But I think there's lots of opportunity right now.

15:50Spencer Gallagher:Excuse the pun. But I think there is an ocean of opportunities right now for all of us to be a little bit more pirate. And yes, of course, bending the rules, twisting the rules, breaking them, innovating creatively. but obviously not breaking laws, challenging them potentially, you know, but not doing anything illegal.

16:08Sam Conniff Allende:Let's talk a little bit about how you've implemented this in your current workflow and your current businesses, this kind of reinventing the status quo, because we've been touching on AI being this great level. If someone wants legal advice, you can upload a contract to ChatGPT and it can explain actually what this legal speak means. I imagine that there's a similar parallel in M &A advisory that you can get quite a lot of good advice now from using Gemini? How are you using these new tools to stay ahead of the curve then?

16:35Spencer Gallagher:Let's talk about reinventing the status quo, because I think 10, 15 years ago, we said every business was a media business. That's how everyone started to speak. Today, every business really is a tech business. I saw a sandwich shop in Brooklyn last week where you can send your agent to go and buy the sandwich at lunchtime. It doesn't we need the website, she needs to connect to the butcher shop to place the order and get it delivered. Ultimately, every business needs to be thinking about themselves as a tech business, whether you're a live event business and you're human to human marketing. Underneath everything, there are ways that technology will improve the way your business operates.

17:11Spencer Gallagher:But I think I want to start by saying, not necessarily just AI, but every business should be looking at their now, next and future. And this is what I've tried to live by since I started. And Because when I started a business in 1999, it was the beginning of the dot-com boom. It actually crashed in 2000, 2001, and it was a difficult place to be for a couple of years. But understanding your business is now, next, and future will help you future-proof what you're doing. Whilst most of your clients might be in the now, understanding the next, which is probably 10 % of your billings, and maybe the future, which is 5 % of your billings, is important because it helps you demonstrate to your customers that you can future-proof their lives or their business, depending on what your company.

17:52Spencer Gallagher:So the first thing is, I think it's important to have an intention to focus on the now, next and future so that you don't get commoditized or you don't get disrupted. Because I think there's a real fear of that. We saw a lot of that happen, didn't we, with the banks? You know how some had the Revolut and the Monzos. They suddenly reinvented and disrupted the market because they're quicker, more agile to be able to create the tools that people needed before the banks were too big a beast to try and move all of their systems and think about the GDPR and the ISOs and all the other rules they've got to think about and work to.

18:22Spencer Gallagher:The second is, how have we implemented it? My journey started in 2017, but honestly, 2023, when OpenAI really came out and we started to see the large language models work. The first thing is, is that domain authority is still quite important at this stage. So if you're a writer, then you can use AI to write really well. If you're a photographer, you can probably prompt beautiful photography. For me, as an ex-web developer, I can probably use some of the AI development tools better than most other people would. So if you're a lawyer and you're using it, it's going to help you more because you understand law.

18:58Spencer Gallagher:If it hallucinates or gives you wrong information, you'll know it, whereas lay people don't. And that's why everyone's been talking about AI slot, because the moment I start designing logos on AI is the moment everything looks terrible, right? Because I'm not a creative designer in that way. I think it's important that we recognize our own authority, our own skills, and how can we apply them to AI. But reality is, is that agents have become autonomous now. And actually, it is possible for highly repetitive tasks that we all do day in, day out to be replaced. And the most people probably listen to this now are probably using AI on a daily basis to ask questions, to solve problems, to rewrite emails and letters, maybe solve spreadsheet challenges.

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19:40Spencer Gallagher:And then you go up a level and you start to create your own GPTs, you might put all of your information in about a subject like a book and it helps you brainstorm further that subject or create outputs based on that subject. And there may be other companies who have put some automation in. So, you know, if this happens, then that happens and to speed up and automate the way that is working. But the thing that's really shifted in the last couple of months, I hate using the word shifted, because I think I learned it from AI, is this autonomous agent side. And now how can you create ultimately something that can complete a task for you by itself.

20:15Spencer Gallagher:For example, I have 20 agents now in the company that all have job descriptions, job roles. They all have guardrails and boundaries, but they're all doing boring tasks that my team don't like doing. So you talk about M &A. One of the most common things we do in M &A is NDA agreements, non-disclosure. So Abby every day, who heads up our business operations, she has to go to company's house, look up the name of the company, fill all their details in, turn the document into a PDF that's signable and send it off. Now she can just ask Tabitha, who is our orchestrator AI, and she says, hey, Tabitha, I need an NDA for this company.

20:52Spencer Gallagher:Can you go and do it? Here's her email address. Can you send it to them?

20:55Sam Conniff Allende:Yeah.

20:56Spencer Gallagher:And it will happen automatically. In fact, it goes one step further. If a client now emails her and says, we get an NDA, it will proactively say, I've created that for you. We're getting to the point now where Abby's happier in her job because she is not having to do those tasks that she just hates doing, those mundane things, and can move her time onto better high value tasks that are maybe sometimes not getting done because she's wrapped up doing admin.

21:21Sam Conniff Allende:One thing I do want to just double click into a little bit is the Now Next and Future framework. Could you just explain that a little bit more, like how you use it? How often you use it? Is that a process that you go through?

21:31Spencer Gallagher:It really is something that we will talk about on our Monday meetings. And it's absolutely something in a monthly board meeting that should be talked about. The now, next and future, for me, the process around knowing what is the now, next and future, what you do is something that you need to bake into every day. So there will be people in your industry who are thought leaders, who are what we call mavens. These are the people who are always out there talking. I mean, I follow two in particular at the moment on AI. One of them used to work for me as an engineer. He's always about two months ahead of me.

22:04Spencer Gallagher:So I don't need to be on the bleeding edge. I just need to be on the cutting edge. Sometimes in the US, you can look at the US in some ways and see actually where demand is shifting and actually Scandinavia. There are two locations where demand for new areas actually accelerates beyond other geographies like the UK. But sometimes those countries can also be remarkably behind the curve. If you're in tech, you might keep an eye on San Francisco, for example. If you're in advertising, you might keep an eye on New York or these days, maybe Austin, Texas. So I think the process is find the mavens, understand the competitors who are leading the way, but get a good feel intuitively.

22:41Spencer Gallagher:When you grow a business, you start to intuitively know the speed of change. You'll start to see when you've moved from this to that to that. You'll understand when things are too early as well. And actually, here's the big thing I always say to people, when someone says it's a fad. Normally, it's going to be the next big thing, right? I mean, I remember iPhones being a fad. At my wedding in the year 2000, 26 years ago, my father-in-law stood up as father of the bride and said, so Spencer's in the internet business. And the whole congregation laughed out loud. In the year 2000, the internet was a joke.

23:20Spencer Gallagher:It's a bit like if I said I'm in cryptocurrency today, you probably think, oh, here we go. But in the end, do we think that actually AI is more likely to use crypto than your own credit card? Probably to buy things. Credit card companies wouldn't allow it. But would it allow you to give it some currency to use? Yes. To go and buy those sandwiches from that store in Brooklyn I mentioned. So it's a really important part of every business to lead, not follow. Don't be a sheep. What have you got for lesson number three?

23:47Sam Conniff Allende:Flatten the ship. This is a super interesting one. It's essentially talking about the hierarchy of organizations and giving ownership to employees and how that helps drive the business outcomes. And I think it's kind of why startups have adopted this quite well in that the norm in a startup is to give every single employee equity or at least options. So tell us more about your views on flattening the ship and how Pirate Cruise reinvented this, I suppose.

24:14Spencer Gallagher:When I grew my business, for some crazy reason, I had a hierarchy and I got to 40 people doing at the time 2 million in billings because I built so much structure in that I was inefficient. In the next year, between 2 and 3 million, I managed to go to 32 people doing 3 million. So I made myself effectively 30 % more efficient by removing hierarchies. And the reason I did that was I read the book I really wanted to bring to the show, Maverick, but it was a book written in the 80s and it's just too dated to bring it but if anyone can dust it down and dig it out it's worth a read and in that book he felt like there should be a way to create a structure that's maybe more organic more like life and he talks about these pods self-containing ecosystems and I love that and he wrote that book in the 80s I read it in the noughties so I started to experiment because I realized there was like a lack of ownership when someone didn't do something it was sort of pass up the chain to the top no one really took ownership and took accountability and people didn't feel safe to take risks, to try things.

25:20Spencer Gallagher:And I wanted to change and shift that culture. And from my perspective, I put flat structures in. I suddenly had more ownership empowerment. I was more efficient. And the business scaled tremendously well after that with a lot less pain points. And I proved that a flat structure could work when everyone was telling me, you can't do it. I then went into a couple of agencies and put it into other agencies. And I was still being told, oh, it won't scale, it won't scale. and then those companies would outperform the businesses that were telling me they couldn't scale. It will do. The problem is, is that most team members are conditioned to have a manager.

25:55Spencer Gallagher:I mean, is it like 80 % of people in the workplace are disenfranchised with their line manager? And that's the main reason for leaving. But at the same time, people want to know who they're reporting to because it stops them having to have that accountability. So it's still taking time, I think for general candidates, employees to understand that you can do things differently and to expand your mind and open it. But pirates did this. Pirates introduced a flatter structure. They had this autonomy. They all knew how to look after things. They all knew what their roles and responsibilities were individually and collectively.

26:27Sam Conniff Allende:Let's dig into this a little bit more because in pirate crews, it was maybe a little bit different to what a lot of organizations are. They have the captain and the reason that they were different to the Navy was because they had the quartermaster and they were actually on a level rather than being just the captain who was the tip of the pyramid in the Navy. So they've got these two people up at the top. And then I don't know if it went really into detail about if there was another layer just underneath them or if it was just like the whole rest of the 80 person crew.

26:53Spencer Gallagher:A flatter organizational structure. In some ways, there needs to be some leadership. Now, whilst that can be collaborative, ultimately, as I once heard the founder of Under Armour say, Kevin Plank, he said, this is what I've heard. This is what I think. And now here's what we're going to do. Sometimes you need someone to bring together a collaborative process to an outcome. So think of the captain as the visionary in the business. The quartermaster is the person who's there to make sure that there's accountability and that the captain is doing things in the right way. But I think when a flatter structure works like this, every person has an individual role and responsibility, right?

27:38Spencer Gallagher:Your job is to fire the cannon, but you're also part of the team that fire all the cannons on the ship. So you worked collaboratively with them to sink whatever, when you're going to attack a ship. Your job is to, with a sword, to stop the people attacking the boat, but you and everybody else with a sword, You're also in a crew together and you have a collective role and responsibility to help each other. It's all about building individual and collective responsibility, accountability, but without this need of saying, where do I go next? What do I do now?

28:10Sam Conniff Allende:One of the differences that's in my mind that I'm trying to understand is I don't know what the progression is. Everyone nowadays, you start with like an entry level job. They don't just have their manager to have weekly check-ins with them. They rely on them to help them develop as a professional. I don't know if that was the same in pirate crews.

28:24Spencer Gallagher:great what you're saying then so a flat structure is based on a meritocracy so it's about the individuals and them working on themselves so think about it as an individual with a personal development plan so right now you've got someone on your team who in their spare time is learning about ai they're investing they're learning every hour out of work when they've got spare time in work they're also investing in it and how it can help them what does jim roan say work harder on yourself than you do in your job. So these people are working on themselves to improve themselves. Now, if that swordsman becomes the greatest swordsman of all time, he becomes more valuable in the marketplace because he's invested in himself.

29:07Spencer Gallagher:He's learned new skills. Of course, the more the team becomes more empowered and more skillful, hopefully, the more money they would go and make as a result of it. Flat organizational structures don't pay people based on their job title. They base them on the value they bring to the organization. So you're moving away from everyone getting paid the same rate of money because they've all got the same job title to what's the value that you bring to the business and how can I reward you for that? So the meritocracy is one thing. And then, of course, the meritocracy can improve your job title because the more skilled you are, the more recognized you become and the more valuable become, potentially, the more money you earn.

29:44Spencer Gallagher:With pirates, they kind of had equal pay. They didn't really do that. But hopefully they pillaged more money as a result of all being better trained. And they all survived a lot longer and didn't pay out as many insurance claims for people losing legs and limbs and et cetera, et cetera.

29:56Sam Conniff Allende:I just wonder if there's a size limit to that. If you've got a 10 ,000 person company, does that still work? The Navy needed to have that really hierarchical structure to make it actually possible to function globally. But a pirate ship is contained.

30:08Spencer Gallagher:Blackbeard actually had a fleet of ships, I believe. And so ultimately, he may well have been overseeing all of the captains. I think we call them squads, basically. So when you do a flat structure, you tend to build groups into squads. I saw a massive insurance company in the Netherlands. I read it in the Harvard Business Review who had built flat structures and scaled it successfully, but ultimately by having slightly smaller self-empowered teams of maybe, I think, 18 to 25 people. So yes, of course, it might be that the organization becomes too big. and Peter Drucker, who said, if most organizations lost their hierarchies, they would improve their efficiency by 30%.

30:48Spencer Gallagher:And Peter Drucker was the greatest management consultant in businesses in the 20th century, arguably. Hewlett Packard had 100 levels of management at one point. Can you imagine? So I think equally, things can get lost in layers of hierarchy, just as much as they probably could get lost to overly flat structures.

31:06Sam Conniff Allende:How important is equity to you? A story of the Facebook graffiti artist. He got paid in shares for doing some work in the early days of Facebook, and he ended up being a millionaire because of that.

31:18Spencer Gallagher:Having the bounty shared among all of the pirates, it seems like the right motivating factor.

31:23Sam Conniff Allende:Is it an essential part of this structure?

31:25Spencer Gallagher:I don't think there's any right or wrong here, based on experience and what I've seen. I think there are businesses from day one that completely distribute equity and create a completely collaborative owned business. I think it's something that on one extreme can happen. My personal belief is that really you should probably do some kind of performance bonuses in the early years because let's just do the numbers here quickly. So like only 3 % of businesses in the UK get to 1 million revenue. I think it's 6 % get to a million dollars. Of that, the businesses that get to 2.5%, I think it's something like 5 % of the 3 % get to 2.5 million.

32:02Spencer Gallagher:So you're a very different business at two and a half to three million net revenue. And the team that you have at three million, I think I only had about six people that managed to grow with the business because some people just couldn't keep up because we grew quickly. And I had to bring in people at three million who could help me get to 10 million. And so I've been into business before at three million who gave equity to all the people at 600 ,000. And those people haven't got the skills to get the business any further, but the owner's got no equity to give away to anyone else. So my advice on balance of experience, I've been into two and a half thousand businesses is try and hold back on the equity till you're around two and a half million.

32:39Spencer Gallagher:At that point, then ask your team if you're going to invite people in, get them to pitch to you. How are they going to help you go from two and a half million to five million or beyond wherever you're trying to get to and ask them to help you with that? Because you're not just giving equity away to lock people into a job because there are other ways you can do that, right? You're doing it because they're going to add value and you want to reward them for the value they bring to the business from that moment forward for everything they've done to get you to where you are today. So it's very common now.

33:08Spencer Gallagher:However, in the UK, especially, there's something called an employee ownership trust. One of the biggest problems in business is when owners get old and the transfer of wealth from elderly people down. Of course, we have inheritance tax. We have all these different things in there to get the government to benefit from it. But as a business, I work with quite a lot of people who are looking to retire. They've got to, you know, 60 and they don't want to see all their hard work going. They don't want to let their team down. So they will consider doing an employee ownership where they sell the business to a trust and the employees are members of that trust and they can then get benefits and bonuses of that.

33:43Spencer Gallagher:And that's happened quite a lot in the UK over the last few years.

33:47Sam Conniff Allende:Yeah, thank you for the amazing lessons. I just want to give you a minute to tell people how to get in touch with you and what's going on with Blue Halo at the moment.

33:55Spencer Gallagher:bluehalowithoutanee, B-L-U-H-A-L-O.com. You can read all about us there. And myself, probably best just LinkedIn, Spencer Gallagher, just send me a message. I tend to connect to people I've met in real life or send me a message that we get to know a little bit about each other. So please send a message in if you connect there. Today, typically I'm helping agencies future-proof their businesses. A lot of people are talking about the end of agencies. I don't believe it. I don't buy it. I've been in this business 26 years. I've heard that been said all the way along. I see a future for agencies that's very different to today, but I certainly know that agencies are businesses that ultimately solve problems that other organizations can't solve themselves because they don't have the time, the money, or the resource.

34:38Spencer Gallagher:And so as long as you can solve a problem that another company hasn't got, whatever that problem is, there'll be agencies around. I'm long on agencies.

34:46Sam Conniff Allende:Amazing. Thanks so much. And if you want to buy a copy of Be More Pirates and leave a link in the show notes. Thank you so much, Spencer. It's been really fun talking to you and thanks for suggesting this book. It's been great to learn about pirates.

From the publisher

If you feel like you're constantly fighting "the way things have always been done," this episode is your permission slip to stop. Be More Pirate by Sam Conniff Allende is the ultimate manifesto for the modern rebel, proving that the most successful founders don't follow the rules—they rewrite them.

Joining me is Spencer Gallagher. At 27, Spencer built Blue Halo into a £12 million revenue powerhouse before a massive exit. He is the author of Agencynomics and the founder of the M&A advisory company also called Blue Halo. Spencer knows exactly what it takes to scale, reinvent, and exit at the highest level.

Today, Spencer breaks down why a book about 18th-century pirates is actually the ultimate guide to 21st-century agility. We cover why the Jolly Roger was the world’s first super brand, why "good enough" is a death sentence, and how a flat organizational structure will make your company dramatically more efficient.

Key Takeaways & Timestamps

00:00 – Introducing Be More Pirate and why 18th-century pirates were actually pioneers of modern organizational structure.

04:05 – Pioneer Thinking: The surprising things pirates invented, including cocktails (to prevent scurvy), flat organizational structures, insurance policies, and equal pay.

05:16 – The "Quarterly Fame Project"

10:51 – Reinvent the Status Quo: Why you must constantly challenge the "this is how we've always done it" mentality, just like Radio Caroline and Radio Luxembourg challenged the BBC.

16:09 – AI as the Great Leveler: Why autonomous agents (like OpenAI's tools) allow small businesses to fiercely compete with massive corporations.

17:23 – The Now, Next, and Future Framework

23:48 – Flatten the Ship: Spencer explains how he became 30% more efficient by completely removing the hierarchical management structure in his agency and moving to a meritocracy.

26:28 – The Captain vs. The Quartermaster: How a flat structure still maintains accountability by separating visionary leadership from operational accountability.

Get the book here

📚Be More Pirate by Sam Conniff Allende

Mentioned in the episode


Spencer Gallagher, Founder of Blue Halo & Author of Agencynomics

Follow Sam on LinkedIn

Want to get in touch? Whether you want to suggest a guest, sponsor the show, leave some feedback or just get in touch to tell me what you're working on, here's the link for you: https://forms.gle/NHGL9ftFRhu4cKFLA

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