AI, Feminine Leadership and the Future of Work

AI is transforming business advice by handling research, planning and documentation, but it can’t yet replace a great advisor because it still struggles with asking the right questions, changing behaviour and owning implementation. Tools like ChatGPT can compress knowledge work, draft strategies and document playbooks in minutes instead of weeks.

Jacob describes how most advisors historically worked: short, exciting engagements with a whiteboard, a model and a few big ideas that never fully made it into day‑to‑day operations. A decade ago, a lot of that could have been replaced by a good YouTube video. Today, AI goes further. It can turn “We need to improve sales” into a full campaign plan, email sequences and a dashboard outline in an afternoon.

But that’s exactly where the gap shows up. AI is still reactive. It answers the questions you ask, based on the assumptions you already hold. If a founder is convinced “sales is the problem,” they’ll ask for better sales scripts, pages and funnels. AI will gladly build those, even if the real constraint is the business model, the founder’s lifestyle goals or a misaligned customer segment. A human advisor can pause the conversation and say, “That’s the wrong question. Let’s talk about the life you’re actually trying to build.”

There’s also the accountability piece. Jacob talks about his own coach as someone who “smacks me in the face with a fish” once a month. That’s shorthand for a very human function: noticing when a client is drifting, calling out avoidance and holding a mirror up to their fears. Generative models can remind you of your tasks, but they don’t yet have the relational weight to make you follow through when things get uncomfortable.

Even AI agents that act more proactively still depend on fragile infrastructure: tools that might not exist in six months, shifting models and brittle product‑market fit. For a small business, rebuilding workflows every time a startup API shuts down is not a rounding error – it’s a real operational risk. Jacob’s portfolio‑entrepreneur clients don’t pay for diagrams or 80‑page decks. They pay for change that actually happens: fewer dropped balls across three or four companies, clearer decisions and less emotional drag. That’s where human context, pattern recognition and trust still matter more than perfect prompts.

Feminine Energy, Leadership and Building Better Businesses

Healthy feminine energy in leadership is about presence, connection and sustainable cultures, balancing the driven, future‑oriented masculine energy that built most modern businesses. Every person carries both energies; the opportunity is to design companies that make space for each instead of rewarding only one.

Jacob draws on long‑standing Eastern frameworks: masculine energy lives in the future, wants targets to chase and problems to solve; feminine energy is rooted in the present, cares about community, relationships and the lived experience of work. Both can be healthy or toxic. Toxic masculinity bulldozes people in the name of results. Toxic femininity shows up as self‑sacrifice – leaders who rescue everyone, absorb every dropped ball and quietly burn out while nobody learns to stand on their own.

The workplace examples are concrete. Jacob sees many founders with strong feminine energy taking all the emotional and operational load. They cover for the team, smooth over client issues and pick up every loose end. Then the one time they need flexibility – say, to pick up a sick child – the team doesn’t step up, because they’ve never been asked to or equipped to. The system silently punishes the very energy that keeps it together.

On the flip side, overly masculine cultures fixate on outcomes and speed. Hiring and promotion skew toward those who “bring home the bacon,” often people who can tune out context and feelings to win deals. Over time, this can mimic what Jon Ronson documented in high‑performing executives: behaviour that looks uncomfortably close to psychopathy, where collateral damage is just that – collateral.

Joe shares how reading Jacob’s work on masculine and feminine energy changed how he built Pinch. Instead of simply rewarding the loud closers, he started intentionally valuing the quiet cultural builders – the ones who keep communication flowing, model care and hold the team together. That shift led to a team that is majority women, steady growth without a hero‑sales mentality and a culture where success is measured in both revenue and how people feel about coming to work.

Jacob offers a practical lens for leaders who want that balance. Autonomy isn’t just about individual freedom (a masculine pull); it’s also about genuine belonging (a feminine pull). Mastery lives between stability (doing work you’re confident in) and risk (stretching into something new). Purpose spans the inspiring future vision and the day‑to‑day experience of working here this week. When leaders design roles, rituals and rewards that honour both sides of each pair, they stop forcing everyone to wear a single “masculine” mask and start getting the best of the whole person.

From Jobs to Output: How AI Is Rewriting the Future of Work

AI is nudging work away from time‑based employment toward output‑based value, echoing pre‑industrial economies where people were rewarded for what they produced rather than hours logged. That shift will likely shrink some traditional roles, but it also opens more space for micro‑businesses, portfolio careers and flexible teams.

Jacob points to economic research showing that before the Industrial Revolution, most people effectively worked as independent operators. They were paid for what they made or did, not for showing up from nine to five. In that world, many people – including women – had far more direct access to economic participation, because output, not attendance, was the primary currency.

Industrialisation inverted that model. Employers started paying for inputs (time on the line) rather than outputs. That change pushed many people out of the formal workforce and embedded a mindset that still dominates: “If I turn up and put in the hours, I deserve the same pay, regardless of what actually happens.” It’s also the mindset that fuels a lot of today’s anxiety about AI “taking jobs.” If your value is defined purely by time in the chair, any tool that makes that time less necessary feels like a threat.

AI, used well, makes output cheaper and easier. A single person can now draft a strategy, spin up content, test messaging and coordinate basic operations at a speed that used to require an entire team. Joe talks about using multiple agents at Pinch to store strategy, answer internal questions and adapt what already works in one market to another. Instead of reinventing the wheel every time, they reuse proven patterns and let humans focus on judgement, relationships and edge‑case decisions.

That doesn’t mean everyone becomes an AI startup founder. It does mean more people can viably operate as specialist independents, tiny agencies or part‑time experts plugged into a few organisations. For businesses, it raises the bar: if talented people can build their own thing with a laptop and a couple of smart tools, you’ll need a compelling culture, not just a salary, to attract them. That loops back to the earlier point – environments that honour both masculine drive and feminine connection will simply be better places to work.

Jacob is blunt about the risks of building a company entirely on today’s AI stack. Tools will disappear. Models will shift. Some “AI wrappers” won’t find market fit. But he’s equally clear that resisting the shift is not an option. The leaders who thrive will do two things at once: use AI to strip out low‑value admin – invoicing, scheduling, documentation – and reinvest that freed‑up energy into trust, coaching, clarity and culture. In other words, they’ll use machines to be more human at work, not less.

Full Podcast Transcript:

Transcript lightly edited for clarity, readability and blog formatting. Timestamps, filler words and auto-caption artefacts have been removed where possible while preserving the meaning and flow of the original conversation.

Joe McCord:
That actual implementation is where all the value is. Ideas are worthless, execution’s priceless. And AI is still a fair way away from being like my coach smacking me in the head with a wet fish.

Hello, everyone. It’s Joe McCord here from Pinch Payments once again. This is the third episode of Pinch Me I’m Dreaming, or PMID, the Pinch Payments podcast.

Today, I am joined by a very good friend of mine, a very special guest. In fact, maybe the most special guest, because Jacob is the person that I interviewed on my very first podcast that I ever created some eight years ago that had a single episode.

I am joined by Jacob Aldridge. How are you going, mate? How are you going, friend?

Jacob Aldridge:
It’s good. It’s good to be back. That was a wonderfully fun conversation, Shock the Startup, so I’m looking forward to our conversation today.

Joe:
Yes. Did you get any mileage out of it back then, Shock the Startup?

Jacob:
I have. I’ve referred a lot of people to the video because, as far as I know, it’s still up on YouTube. It’s embedded on my website, because we talked about so many cool things.

Whenever I say something smart, I love pointing people to videos that are that old where I’m saying the same smart things in a much younger man’s body, so that I look like I’ve been smart for longer than perhaps I really have.

Joe:
And of course, you are a very smart man, so you don’t have to pretend all that much. Unlike me at the time, you actually were smart even then. I’d like to think I’ve gotten a bit smarter now.

Before we start going into too much nitty-gritty, why don’t we talk a little bit about you? Just give the audience a little bit of an idea of who you are, what you do, what you’re all about.

Obviously, you are a business advisor, you are also a published author, and you are a digital nomad, which is a lot of things I aspire to be, mind you. I’m thinking a lot of this episode is probably going to end up me trying to figure out how I can emulate that and figure out how to do what you do and steal your life.

Not Single White Female style, but similarly.

So yeah, tell us: where are you at right now? What are you up to? What are you doing with your life right now?

Jacob:
Da Nang, Vietnam is where I am right now.

Yes, full-time travel family. My beautiful wife and I and our seven-year-old daughter have been on the road. We left Brisbane again, but properly, at the start of 2025.

We change countries every two to three months. We worldschool, which is that integration of homeschooling and interconnecting with the locations that we’re at, the communities that we meet, both the local and the other weirdo worldschooling families that are out there.

We work with our advisory business, which is now 20 years old this month, so that’s a cause for celebration, and is now fully remote online.

That’s the life that we lead, and I can recommend it.

Joe:
Yes, I can imagine. Every time I check in with you, you’re in a different country.

How many times a year do you get back to Australia these days?

Jacob:
None. Not yet.

Joe:
Zero times a year.

Jacob:
Yeah. It’s a good number.

We spent a lot of 2025 in Europe and North Africa, and nobody wanted to come and visit us. We shifted to Southeast Asia for 2026 for a few reasons.

Joe:
That’s a little bit closer.

Jacob:
My parents and my in-laws have both come to spend some time with us in this part of the world, so that’s a little bit easier.

We still haven’t had the need to get back to Oz. I think we might be back for Christmas this year just to see the family, make sure that nothing’s gone completely wrong, give the clients a bit of face time.

Apart from that, it kind of works.

We had this moment where Harmony was in with a client, and she had a series of one-on-one meetings with the team, so she was in at the client’s office.

Each of the four or five meetings that she had that day just dropped her a note and said, “I’m actually working from home today. Do you mind if we do this on Zoom instead of in person?”

So we had this weird experience that, 20 years ago when I started doing this, I would never have imagined, where she was in the client’s office and all of the actual clients were working from home.

We thought, “Well, they don’t care where in the world we are. We may as well go wherever we want.”

Joe:
It feels like that, but at the same time, the whole world hasn’t quite caught up yet. There’s still a bit of social pressure. There’s still a bit of corporate pressure. But I suppose it’s relaxed. You can certainly see it coming.

Twenty years is a long time to have a business run in perpetuity. There’s obviously a lot of hard work that goes into keeping a business afloat for 20 years and to transition from a business that you used to run as a traditional business to one that you’re running as a world-travelling family.

How did you navigate the fear? Surely that must have been the biggest thing.

As I mentioned to you before, I’ve had aspirations to do what you do for the entire time I’ve been a working man. Taking the leap of faith to just go and do it — how did you navigate that?

Jacob:
There’s a lot of personal development work.

Business advisory, business coaching, different ways you can tackle it. One of my first mentors described it to me as a professional opportunity for personal growth.

If you go out there, if you run your own businesses, if you help particularly small and medium-sized business owners who are so driven by their emotions, conscious or not, you can’t but tackle that in a way that leads to your own personal development.

Certainly my coach, who smacks me in the face with a fish every month when we have our coaching sessions, that’s a big part of the work that she has been doing with me.

On and off, I’ve had different coaches for what I’ve needed over time, but she was my first coach 20 years ago. She’s the current coach we have in our business.

A big part of that is just shining a light on those fears. Fear is one of the fun acronyms: future expectations appearing real. It’s projecting what could happen in the future and feeling that feeling right now, even though it hasn’t happened yet. It’s completely imaginary.

The best tool that we’ve had to really overcome those is to step into that future and go, “Well, what is the worst case? What is the worst thing that could possibly happen?”

Outside a meteor strike, realistically, what’s the worst thing that can happen? Invariably, it’s actually not that bad.

When we took off in 2025, for example, it was like, well, the worst thing is we get six months, 12 months into this, it’s not working, the schooling isn’t working, we’re not making money.

We go back to Brisbane. We move back into our house that we had rented out. In 12 months’ time, if we do nothing, we’re going to be living in Brisbane, the kid’s going to a regular school, we’re running this business, or we’ve got a job.

If we do it, in 12 months’ time, worst-case scenario, we’re living in Brisbane, kid goes to a regular school, we’re running this business, or we’re doing a job.

If it’s the same outcome either way, we may as well give it a try.

There have been a few instances of that over that 20-year period where we’ve moved countries, we’ve changed business models, or we had a horrible experience becoming parents, and that took a lot.

Throughout that, it’s just us together as a team going, “Well, what have we got to lose?” Usually, it’s not that much.

Joe:
This is probably a good time to go a little bit deeper into your business, what it is that you do, who it is that you do it for, and I guess what separates you from another business advisor.

What do you teach? What’s your strength? What do the businesses that work with you succeed by doing that they might not do?

Jacob:
Well, I’m ridiculously good-looking and modest, which obviously sets me apart, and a little bit of a sense of humour and a belief that business is best when it’s fun.

There are two businesses really that I’m primarily part of, apart from the others where I’m kind of on the board or an investor.

We’ve got Como Legal Coaching, which is the business that Harmony leads. She had 15 years as a practicing lawyer, so she does the bulk of that work, and I tend to come in and help with some of the more finance or strategic aspects.

That’s primarily transforming female-led law firms in Australia and the UK, although being remote, we can work with law firms around the world because so much of it is the business, not the specifics of legal jurisdictions.

Then my core focus these days is what I call portfolio entrepreneurs. It’s working with those people, mostly men, to be honest, who have a meaningful stake in multiple businesses.

When I made the decision to lean more into the schooling and the parenting and to work fewer days, I realised that my traditional business model of running 12, 15, 20 clients a month was not really sustainable. It didn’t work. I didn’t have the time and capacity to hold that many clients.

But I had worked with a few of these portfolio guys who struggle because, just like a stereotypical business owner with one business, it’s often lonely at the top.

If you’ve got multiple businesses, you might have partners or CEOs that sit across them, but nobody else who is actually across them all.

Having me as the consigliere, as the advisor who can sit with you and hold that space and can jump into all those different businesses, is a valuable, helpful thing to do.

That way I can run a small number of clients, but really give them that depth and availability.

In terms of what makes me different, it’s the context, not the content of business.

I have over 20 years in my training and ongoing training, as well as the development of our tools, built together a whole integrated system that I talk to my clients about.

But it’s not a, “Here’s an ERP or a workflow management system, you’ve got to do all of these things this way.” It’s not EOS, which is like, “Here are the meeting agendas you must run.”

It’s contextual, which means it’s all about what this person and this business want or need, which is a challenge for those portfolio entrepreneurs, because what works in one business is not necessarily going to work in others.

If you learn the content and try to copy-paste it, you can be copying the wrong homework, as opposed to having those contextual tools and having them in such a way that they’re integrated.

I can bounce from recruitment to pricing to vision to culture to strategic growth planning to what are we going to do with the toilets in the office that keep leaking, in a 15-minute conversation, so I can keep up with the entrepreneurial head.

Again, I think it’s reasonable to say most advisors, business coaches, accountants, mentors can’t really do that. They’ve got their specialty or their lane, and business owners, particularly with multiple businesses, your brain just doesn’t work in single lanes.

Joe:
I’m going to go out on a limb and suggest that the proliferation of AI has made your job very different to what it was a few years ago.

Jacob:
Not yet, but it’s coming.

AI can replace, I think, probably 80, already 80 or 90 percent of what the average business coach or business advisor can do.

I remember when I was working in the UK, I was part of a group. I was licensed through a group, and I did some time there as the COO. I did my round within the group, running the operations for the national business and helping overcome a few of the challenges that we had.

Back then, I think we had about 80 coaches in the UK that I was not coaching. I was going, “This is what you need to do. You need to shift.”

The problem even back then was most coaches have a very short engagement cycle with their clients. A lot of advisors do the same, where you’ve got the interesting new conversation, but not the actual implementation experience, and nothing actually changes.

You could replace a lot of what those advisors do when they get up on a whiteboard and draw a diagram with a YouTube video 10 years ago.

What AI can do is take that from the concept inspiration level down to the strategy education level and actually map out, “Here is the plan. Here is what you get to do.”

What AI still can’t do, and frankly what most advisors and business coaches and accountants who sit in that advisory space still can’t do, is ensure the implementation happens.

We’ve got a great AI agent in our business who can do that. He does stuff for me, but he’s not implementing the real change, and he’s not changing my behaviour.

For the people who want that change, they can leverage AI. Maybe they can get pretty close to it today, but that actual implementation is where all the value is.

Ideas are worthless, execution’s priceless, and AI is still a fair way away from being like my coach, smacking me in the head with a wet fish every month.

It’s a fair way away from actually helping with the implementation. That’s why I get paid: to actually implement change that’s valuable to my clients, not to roll out a gorgeous strategy plan that’s 800 pages long, that someone’s just going to take and put back into AI and say, “Hey, can you please summarise this?”

Joe:
When I asked the question, what I more meant was, it should be able to compress a lot of what you do so that you can actually do more of it.

I use AI a lot for developing strategies and plans. I have multiple agents that do things like house all of my strategy in a strategy AI so that, if people need to ask questions about the strategy, they can ask the AI instead of asking me.

Also, to your point, a really interesting point that you made about people having skills that they can really only apply in a single lane: AI has a really powerful way of being able to translate the application of things that you’re good at in one area and apply it to another, and give you a way to actually translate that application into another area.

That’s something that I find we do a lot here at Pinch. Not only that, but actually build the plan in a resilient enough way in the first place so that it has cross-application potential, so that you can avoid that particular problem.

We get a lot of repeatability when we go after a new market or launch a new product. We can do a lot of the same things when we make choices about markets that we go into.

We weigh up whether we already have enough momentum in a relative market so that we can get cumulative value out of what we were already doing, stuff like that.

I think that’s where AI is at now. In terms of assisting with knowledge work and stuff like that, that’s pushing — I’m not including product development and coding. That’s a whole different ball game.

But when it comes to helping knowledge workers out, that’s kind of almost the tip of the spear of where it’s at right now, I think.

Your businesses that you work with, your portfolio entrepreneurs, do they tend to mostly be investors instead of founders, or is it a bit of a mix?

Do you see people who are founders that then dabble in investment, so they have their one core investment and then they have the ones that they’ve got minor equity stakes in? What’s the mix there?

Jacob:
They’re founders. Maybe they’ve had one successful exit, or they have had a business that’s got to that point where they can shift focus.

It’s not just, “I’m an angel investor now. I’ve got 5% here or 5% there.”

It is where they’ve got multiple businesses where, whether they’ve got 20%, 50%, or 100%, they are putting time and effort into those businesses. It’s not just the dumb, silent money.

Joe:
Yeah. Okay.

Jacob:
The idea that they tend to have — and some of them have invested in some really dumb businesses before they met me — is, “How do I magnify my brilliance?”

Instead, what happens is all the monkeys from all the different businesses get magnified and flung their way.

If they’ve got a business partner or a CEO or a manager who’s running the day-to-day operations, that person is like, “Fantastic. I can just fling all the hard questions up to you.”

Before they know it, they might have four or five different businesses that, instead of magnifying their energy, are just sucking all of their energy because they’re constantly getting all of the problems across all those different areas.

They didn’t need that the first time, because the first time they had a good business that worked. They never needed to think about how business in general might work, or how they could apply those things.

Joe:
Sounds to me like you were AI before AI.

Jacob:
Yeah, well, they were going to call it Jacob, but they went with Google instead. Then ChatGPT talked to me about licensing the name. That’s why it’s ChatGPT. Then there’s Claude and Victor. They were all going to call it Jacob, but again, I was charging them too much, so they went with ChatGPT.

Joe:
The reason I mention that is because, at least for me, I’m not a multiple founder, but if I was, the role that you play in what you call your consigliere role, which I absolutely love — a beautiful way to put it — is certainly a role that I would naturally use ChatGPT to play.

But you raise a really valid point, and it’s a point that I’ve been pondering a lot lately. When this all finally reaches its crescendo, and the speed with which it normalises and gets to the point where this is what AI has done in terms of transforming society, and it’s locked in place now, when we get there, relationships and actual human-to-human contact are still going to be critical.

In many ways, maybe even more critical after we have to go through the experience of losing it, which I think we’re midway through right now. We’re currently coming out of COVID, and we’re seeing nations having issues with population growth because people are not communicating in public anymore, not going out.

We’re going through this meta translation of relationships, and I think on the flip side, coming out the other end, people are going to be longing for it. It’ll end up being overvalued compared to what it is now, even.

So for you to play that role now, where you’re actually being the one — what did you say? Something with a fish?

Jacob:
Getting smacked in the face with a fish.

Joe:
You say you’re the one slapping people in the face with a fish.

Jacob:
That’s what they pay me to do.

Joe:
I think that skill is absolutely critical moving forward, even more so than maybe any other skill.

Jacob:
AI agents are here now. They’re getting better. That took longer than I was expecting, but it’s accelerating faster.

It might be next week, it might be next month, it might be next year where it gets to this point.

But still today, the generative AI enmeshed solutions — Claude and ChatGPT and Gemini — are very much responding to your questions.

The value in a coach and advisor and mentor has always been them asking you the questions, not giving you the answer.

When you’re in your own world and you can’t see the picture because you’re in the frame, it’s very hard to ask a question that broadens your point of view. Because if you had that point of view, you wouldn’t need to ask the question.

Where that gets lost is, if you’re super confident that sales is the problem I’ve got, so I need a better sales page, I need my sales team to be trained better, they need better conversion, they need better scripts and dialogues — which I don’t believe in, but whatever it might be — and you go to those tools and you ask it for better sales, it will give you better sales.

What it won’t do yet is say, “Actually, did you know that in the context of your personal vision, your business model is broken?”

So I can fix sales, but all that’s going to do is embed you worse in the life path that you’re currently going on.

If you want to be a full-time traveller, you can’t have more clients like this. Sales will get you more clients like this, but actually, you need to find out how you can get clients like that.

That takes a different kind of AI — Aldridge Intelligence — to be able to bring that broader perspective.

When clients ask me the questions, sometimes I can just put back, “Actually, I don’t think that’s the right question. Have you thought about this?” in a way that a lot of AI tools currently can’t.

I did an article for the AI Journal about first-mover disadvantage, which I think is playing out a lot in this space, because those businesses that are leaning into AI — because it is so early, and we forget when we’re using the tools, when we’re talking to other people, that the vast majority of business owners worldwide have never used ChatGPT.

They have never implemented AI into their operations.

We’re way ahead of the curve, and some of the technology is very rudimentary, and it will change in a huge way very quickly.

A lot of the tools that a business owner might build solutions on are not going to be there in six months because they haven’t found product-market fit. They fall over.

Small and medium-sized businesses can’t afford that risk of investing all of that time, even if it’s not that expensive, into tools that might not work.

A lot of the people who are at the leading edge or the bleeding edge of this technology, they do it for fun. If you do it for research, if that’s your context, then that’s fantastic.

But if you try and build a business on some of these things, there’s a huge risk that that whole operational model is going to fall apart.

Joe:
I think that if you’re building a business on top of AI right now, it’s more than a risk; it’s a guarantee.

AI is collapsing in on itself, constantly innovating on top of itself, and what it’s capable of doing is changing too fast for you to create something as static as a business, something that you have to actually take into market.

By the time you get it into market and get pilot customers, you’ve taken your eye off the innovation and you will be behind the eight ball.

I totally agree with your point.

Jacob:
Even if you’re a regular business, if you’re a business advisor, if you’re a plumber who is leveraging the tools and going, “Oh, that’s fantastic. I’ve found a way to get my invoicing automated,” or, “I’ve got an AI receptionist now who can answer the phone and take that, and it works really well.”

Then in three or six months, that tool no longer works, or the model changed to fit a different solution a bit better and your AI receptionist is now cranky.

There are those risks still playing out, which has always been the case with any kind of technology. Some business owners succeed wildly because they love constantly chasing the new technology.

But it is still very early days, and we can’t forget that when we’re going out to businesses and talking to them.

Joe:
Receptionists have been getting cranky since receptionists were a thing, right? So what’s the difference?

Jacob:
I started my life on the front desk. Undervalued job in most businesses. There are far fewer receptionists now than there were 20 years ago, that’s for sure.

Joe:
Right now, probably the most common job that AI is doing for online businesses especially is triaging that first touch point, and people hate it.

For businesses that have AI as first-line support, which we do, so I’m going to be a little bit of a hypocrite here. We also happen to have very proactive real support, so you kind of can choose A or B. It’s like door one, door two, not door one until you get frustrated and then, “Okay, fine, we’ll talk to you.”

For businesses that are like that though, you pull through their LinkedIn posts and social commentary about them, and it’s just, “I am so tired of dealing exclusively with an AI support bot. I just want to talk to a real person.”

Jacob:
I think you’ve got to go, what’s the comparison?

There’s a great meme that does the rounds. If anyone’s listening to this instead of the visual, you’re going to miss out. But it’s sort of the two faces of the guy.

The first one is him smiling: “When you realise you haven’t seen AI images for a while.” Then it’s like, “Oh, when you realise you haven’t seen AI images for a while.”

People don’t care that you have an AI receptionist, AI help desk, AI-written blog. People care that your receptionist, your help desk, your blog is crap.

If you’re using AI to create crap, that’s the problem, not the AI.

Similarly, what’s the alternative? Because if you’re that plumber who’s elbow deep in “your shit is my breakfast” kind of career, you’re not answering the phone when people call. Having a mediocre AI solution is still better than what you’re currently doing.

We can look on the outside and say, “Well, you’ve got a terrible solution because look at what Pinch are doing. They’re amazing because they’ve got resources and a great product and a team and all of these things.”

But that’s unrealistic. It’s like saying, “Why can’t I run as fast as Usain Bolt? I eat the same number of chicken nuggets. What’s the problem? I should be able to do it.”

Different businesses, different comparisons.

Joe:
I love the analogy. Yes, that’s correct. Not everybody can be like Pinch and not everybody can be like Usain Bolt.

Pinch and Usain Bolt: two peas in a pod. Going places and going places fast.

Okay, you might be sick of talking about this because this goes way back, right? It might show how long it’s been since I’ve logged onto your website. But you were a contributor or author of a book, right?

Jacob:
Be more specific. I’ve written six books.

Joe:
I’m talking about Visionary Male Leaders.

Jacob:
Yeah. Nice.

Joe:
I think you were a contributor, not the author, though, right?

Jacob:
There were a group of 18 guys who wrote about visionary male leaders and embracing feminine energy in the business leadership space.

Joe:
At the time that came out, that was like, “Whoa.” Now, masculine, feminine, gender — it’s so much more of a topic.

When I first saw that book come out, firstly, it resonated with me. I have always been able to acknowledge that at certain times I’m channeling feminine energy, and at certain times I’m channeling masculine energy.

When I read that book, or when I read your part especially, I was like, “That’s it. I just totally understand that.”

I think we should talk about that because I genuinely still feel like it’s such amazing information, and this is not talked about enough.

Can you go ahead and just establish the premise?

Jacob:
The challenge I have with it is it’s thousands of years of mostly Eastern research and application that have led to this masculine-feminine conversation, which then gets confused with male-female binary gender conversation.

I think that then blurs into the confusion and the problem, particularly in workplaces, which is my area of expertise, but more generally in society, where we know that there’s a lot more to gender and sexuality than a binary nature.

Any kind of conversation around masculine and feminine feels like it’s tapping into that conversation, when actually it’s not. It’s a different conversation, and it may be the solution to a lot of those binary, non-binary problems.

The idea, and the yin-yang diagram that a lot of us are familiar with, is part of this history. We are all a combination of masculine and feminine energies.

The masculine energy tends to live in the future. It wants to go and hunt the next kangaroo. It’s driven and motivated by that sense of purpose, and it wants to find that way to have the solution, to fix the problem, to find new challenges.

The masculine can be healthy, and it can be toxic. Most of us are familiar with toxic masculinity as a concept.

The feminine energy is much more rooted in the present. It has a drive for the sense of connection, of community, and that need to be present in the right community, connection, group, in a way that the masculine is less oriented.

The feminine can be healthy, and the feminine can be toxic.

Toxic femininity is where you, as an individual, sacrifice yourself for people who wouldn’t return the favour.

I see this so often in female business owners, where they will take the muggers, they’ll take the tasks, they’ll take the responsibility, they’ll rescue their team, and then the one time a year where they have to go and pick up a sick kid from school, the team don’t step up to help them.

They’re not empowering the team, but they’re just sucking their own energy and their own ability to help team, clients, family, all of those kinds of things.

It’s healthy and unhealthy on both sides. We’re all a combination of both.

Most men are predominantly masculine, and I am definitely predominantly masculine energy. What’s the drive? What’s the purpose?

Most women are predominantly feminine, and so that’s where the confusion gets in, because a lot of modern business — 20th and 21st century business — has been built by men from a masculine space.

If you look at even some of the language, it’s like you need a mission statement. Mission is a military word.

We started applying that in businesses after the First World War, particularly after the Second World War, where it was the military. What’s that mission? What’s the purpose? What’s the thing that we’re attacking right now?

When I started 20 years ago, using some of that language and some of the training, it never occurred to me that maybe it wasn’t universal. I just observed that most of my clients were dudes.

Then I ran a workshop maybe in 2009 or 2010, before I moved to London. I was still in Brisbane.

I did this great exercise that everyone loved, where I walked the people out of my office and out onto the street, and I got them to look at the horizon and look at the footpath and feel that difference and all of this kind of thing.

I’m doing the feedback at the end, and there was a female architect, a very successful architect in Brisbane. She was like, “I didn’t get it.”

I thought, “Oh, wow, aren’t you dumb?” I didn’t say that, but it was like, okay, not everyone’s going to understand business, right? So here’s someone who doesn’t understand business.

Then you learn more, and you do more training, and you do more research, and reflect on it. Actually, not only were most of my clients men, but the female clients I had were actually quite masculine in their approach to business, naturally or because that’s the mask they had been taught.

So what if we actually did this differently?

That’s what eventually led to me being connected with the editor of Visionary Male Leaders and contributing to that.

My part was particularly: how do you, regardless of your preference or if you’re balanced — and I’ve got an online quiz we’ll put out there for anyone who’s interested about which is your strength — wherever you are, what are the systems you can put in a business that attract both?

It’s not just then, “How do we help women rise in business?” It’s about, how do we embrace all of all of us?

Because we are all a combination. If our business is only established to support the masculine energy needs, then all of us lose, because part of us, whether it’s a small part or a predominant part, is not being embraced.

If we can build the systems in business that embrace both, then everybody wins, and we lose the whole, “I’m a white man, therefore I can’t get promoted” kind of nonsense that goes on around diversity, equity, and inclusion conversations.

Joe:
You’ll probably be happy to know I was extremely inspired by reading what you wrote in that book. There was a little bit of an epiphany for me.

I’ve certainly gone on and embraced the idea of creating an environment that embraces both energy types, not just one over the other.

Like you, acknowledging that I was more naturally geared the masculine way.

Honestly, it’s been super transformative, because by creating space where people who are more naturally feminine — i.e. women — are actually able to be acknowledged and recognised and validated for the strengths that they bring, it has this transformative impact on the entire culture, but also on them.

I was actually having a conversation with my team earlier this week where I was thinking to myself, “I want to make a LinkedIn post, and I want to say, ‘Let’s talk about the growth hack of hiring competent women and trusting them.’”

Jacob:
Yep. And particularly part-time, because then you only have to pay for three days, but they still give you five days’ worth of time and 10 days’ worth of effort.

Joe:
I do have a couple of women on my team that work part-time. But I’ve got a team of nine now, and eight of them are women.

To be honest, the growth is not what you would expect to see in the sense that it’s not driven by sales, it’s not driven by KPIs.

Jacob:
It’s not hunt the kangaroo.

Joe:
No, but it’s steady and consistent, and it comes with this energy that’s actually super, super lovely.

We’re succeeding with this cultural payments technology by real people caring for one another, having fun, communicating, being present with each other, talking to people. It’s honestly amazing.

I’m a little bit of a contrarian, so part of it was that I probably pushed the boundaries of it a little just to see if I could actually almost make it work in spite of leaving even the masculine stuff completely off to one side.

It has. It has absolutely worked.

I think I owe that to you, to be honest, for opening my eyes up to the business application of the concepts. Not to the concepts, because the concepts are natural to me, as I said, but the business application of the concepts. The business application of the concepts was genius to me.

To further the point, have you ever — are you familiar with Jon Ronson, the author?

Jacob:
No. Not off the top of my head.

Joe:
Jon Ronson wrote the book The Men Who Stare at Goats, which was about the CIA MKUltra, and also The Psychopath Test.

Jacob:
Yeah, yeah.

Joe:
Both quite famous books. The Psychopath Test was a book where he basically did a whole bunch of research into high-powered executives in American businesses to discover whether there was a correlation between high-level performance in business and psychopathy, which he discovered that there was, in fact.

Jacob:
Yes, there was.

Joe:
I actually wrote a LinkedIn post about this, and I think it sort of touches on your point a little bit.

When you have a corporation that’s completely masculine and becomes over-masculine, generally what happens is that everything gets analysed by the ultimate outcome, the hunter-gatherer stuff.

Who brings home the bacon? They rise to the top.

In that culture, the people who rise to the top are generally people who put their blinkers on and go after the target, and they don’t focus on anything else.

They don’t contribute to the creation of community. They don’t worry about other people’s feelings. They don’t necessarily intentionally cause problems. They’re not necessarily toxic. It’s collateral damage, to take another military—

Jacob:
It’s collateral.

Joe:
Yes, but that’s what happens.

Then what happens is, in an organisation that only understands how to be a masculine business, those sorts of people rise into leadership positions in the business, and they don’t understand how to actually manage people.

Jacob:
Or that there might be a different way, because this has worked for them.

Joe:
The LinkedIn post I put up was like, if you can find ways in your business to attach tangible enough metrics to the performance of people who are performing the other role in your business — i.e. the quiet culture builders, the people who are keeping the glue together — and actually tie what they do to business outcomes, and give them just as much validation and just as much respect when it comes to performance review and things like that, you find that they’re more equipped to actually lead or co-lead.

Obviously, because as you say, you still need both energy types.

But you create an organisation that people want to be a part of. It’s enjoyable, even for the people who have masculine energy, because suddenly they’re not having to fight for every scrap, which creates a scarcity complex.

It’s honestly great. It’s actually amazing, and I think I owe all of that discovery to the trigger, the seed, that you planted in my head.

Jacob:
Thank you. I’m glad to hear it’s landing.

One of the smaller things I do is fly around for keynote speeches and conference workshops and that kind of thing, and it is one of the ones on my list.

I’ve had the opportunity to run it a few times, like embracing feminine energy for more successful leadership.

But I still find when I pitch that with some others, people are a little bit scared of that conversation or what that conversation means.

I remember the very first time I did it. It was an audience of 50. There were 50 people in the crowd, 49 of them were women.

I’m like, “Well, if the people with the power don’t want to change, it’s not going to change, so let’s have the conversation.”

Joe:
That’s bold, man. Bold.

Jacob:
They did the mic at the end. It’s like, “Any questions?” One of the women put her hand up and said, “Actually, I don’t have a question. I just want to say, when you stood up there as a man in a suit and said you were going to talk about feminine energy in business, I thought, ‘What is this bullshit?’ But actually, now I can’t imagine anybody else having that conversation as well as you’ve just done.”

That’s kind of cool as well.

I hope to do more. I’d love to speak about that every week to businesses and communities, because it’s a rapid change. I talk about AI and being a generalist, and I do some other more wacky, cool, smart-dude presentations.

But that feminine energy piece, you can take that on a Friday and implement it in your business on Monday, and you’ll get immediate effects. So I’m glad to hear it’s working. I’m glad you’re a case study.

Joe:
Yeah, man.

At the moment, I’m also working with a wonderful organisation called Tech Ready Women. Tech Ready Women is an accelerator. At the moment, we’re mentoring through 51 female founders, generally ex-professional women who have had a dream and are trying to get off the ground and pivot into first-time founding.

I think that what you talk about, you probably have some really good insights to share with people like that.

Can you take the time to think of something to say? What would you say to a female founder who may have come from a corporate or business background and is taking that next step?

Jacob:
I think the first thing is don’t throw the baby out with the bathwater.

This is a common mistake I see, especially when I talk about the female-led law firms that I’m increasingly doing some work with, which I never would’ve got if I didn’t have a strong female co-founder in my beautiful wife.

They know what they don’t want, but they tend to throw it all out.

So, “I don’t want the hierarchy, so I now sit in the open-plan office myself, and it’s frustrating the heck out of me because I can’t get things done, and I can’t take half the phone calls because the team can hear the conversations around the business.”

They go too far. So it’s just avoiding that trap. That’s a small thing.

I think the big thing, and it’s a broad contextual framework I use a lot that I stole from a coach in Perth called Millie Aitcheson, is: permission, listen, choose.

Give yourself permission to do anything, to create anything, and that’s the business model, and it’s the culture, and it’s your personal life.

You can choose anything, because women particularly are trained to wear the mask. You wear the mask at school, you wear the mask at university, you wear the mask in your career to get through, to get by, to play the game in the way it’s currently being played.

It’s very hard to get that mask off, and that mask is very limiting.

So the first thing you have to do, which sounds easy but can be quite challenging, is genuinely give yourself permission to go and create whatever you want, and then have the space to listen.

Permission, listen, choose.

Listen to what your heart, your soul, your gut is saying you want to go and build.

The pin brain, thinking brain — the brain wants to be right, the body wants to be happy. Listen to your body when it comes to that.

Because you can do the pin brain thing. You can sit down with AI later and go, “Is this viable? Is this realistic? I want to be a billionaire who sells flowers on the side of the road.”

That can come later. Don’t let that get in the way of listening to what your heart has to say.

Then once you’re connected with that, which can take a long time, choose. Choose it genuinely. Don’t just go, “That’s a good idea.” Go, “That is me.”

If you’ve done the permission and the listen bits well, then that choice becomes really, really powerful.

That is then what drives you. You don’t have to change the world to be innovative. That is what’s going to drive you to change your world.

Business exists to add value to other people. If you’re successful in business, you will be helping other people, and that’s how it works.

If you choose what is going to work for you and your heart and soul, then that is going to go out and help other people.

Joe:
Man, that was awesome.

Let’s turn it around on the flip side. Let’s say there are male business owners listening to this podcast, or masculine female business owners. Let’s say they’re inspired by the idea of being able to create space for both energy types.

How would you consult with somebody and help them figure out how to transform their business in a way that’s going to create that space from one that’s masculine to one that’s feminine?

Very hard question, I know.

Jacob:
It’s got the balance.

The framework I developed and shared in Visionary Male Leaders was building on Dan Pink’s work around autonomy, mastery, and purpose, which is great, but can be misapplied, I find.

The struggle with the application there is that, across each of those, there is this dynamic pulling between the masculine and feminine energy sides.

With autonomy, it’s the pull between the sense of independence, individuality, and that need to belong. People move along that continuum constantly, which is what makes people leadership so hard for a lot of people.

It’s like, “I think I’ve got Joe pegged. He really wants to be an individual and a leader.” Then we catch up six months later, and all of a sudden you’re building a team, and you’re belonging, and you’re talking culture.

That’s not a change. That’s just different parts of you taking priority.

So you’ve got individuality, you’ve got belonging.

Mastery is about stability and risk: trying new things, but having the opportunity to do good work that you’re confident you can do, which is much more of that feminine.

The male wants to try new things. The joke is quite true: if there’s a job ad, the feminine says, “Oh, I’ve only got 95% of the attributes. I’m not qualified.” The bloke goes, “I’ve got 10% of those. Let’s give it a crack. I’ll learn it on the job. I’m happy to take that risk.”

Whereas the feminine prefers the stability, the presence.

Then the purpose is around the future and the present.

We often talk about the big vision, the janitor that tells JFK, “I’m helping put man on the moon,” and that’s a great story you’ll hear 100 times at every conference. That’s the future, which is the masculine.

What’s the present? What is the experience you and your team have when you come to work every day?

Because if that’s crap, then the feminine energy isn’t going to hang around to put man on the moon, and that’s going to make it harder.

So it’s getting that balance.

Individuality and belonging: what are you doing on both of those?

Stability and risk: what are you doing on both of those?

Presence and future: what are you doing on both of those to lift everybody?

Because we all have all of them.

Joe:
I’ve been thinking about ways to develop a system or framework that is able to directly correlate business growth — revenue, share price, all that good stuff — with your employee morale.

That’s something that I don’t think was possible until recently, with the way AI is able to compress information.

In the past, you could say, “We’re doing employee surveys once a month, da da da. We’ve got good employee morale, and we’ve got good revenue.”

But then somebody else would come along and be like, “Well, we’ve got good revenue because we’re hitting the numbers, we’re making all the phone calls, we’re closing the deals. It’s all happening that way.”

Now, because you can actually compress the data even more, and you can even run models where you say, “If you removed the one aspect from it, what would actually be the case?” I feel like that’s such a powerful area of exploration of business philosophy.

We’re about to enter a transformative labour workforce era. We’ve started seeing it: the rise of the gig economy and digital nomads and things like that. But I think by force it’s going to happen, where a lot of people are going to be — I don’t know whether it’s fair to say that AI is going to take people’s jobs, but it’s going to transform the workforce.

Jacob:
It will take jobs that exist. I think other jobs will be there.

Joe:
That’s the hope. That’s the optimistic perspective.

Jacob:
I’m an eternal optimist.

Joe:
I kind of am too. I kind of live there.

But what that is going to mean is that it’s going to create a labour workforce that becomes a lot more capable.

There’ll be a lot more micro businesses, a lot more small businesses, a lot more sole traders, a lot more people who are going to find ways to make business online and find other ways to get by.

Actually getting somebody to work for you is going to be really hard in the not-too-distant future.

Jacob:
That’s the historic norm.

It was the 2024, it might’ve been ’23, Memorial Prize for Economics. It was won — I’m not going to remember off the top of my head what her name was — but her research was into female participation in the workforce.

It highlighted something I talk about when I talk about deep generalists versus AI, and how we as humans leverage our advantage.

Pre-Industrial Revolution, so we’re talking 1700s and 200,000 years prior to that, work was much more independent. It was much more individualised, and you were paid on output.

A lot of it was survival. It wasn’t necessarily a great place to live, and you couldn’t specialise. You couldn’t be the podiatrist in the village. You had to be doing a lot of all these different things.

But because you were paid on output, women were on equal footing with men.

Maybe there were some tasks where they weren’t able to produce as much, but if you had a woman who, in a day, with the strength, could make 10 of these things, and a man could make 20, the man made twice as much because they produced twice as much, and that was fair.

There were obviously some areas where women could produce more and men less.

Most research into women’s participation in the labour force has looked at the Second World War and afterwards, and how it started really low, and then wartime job shortages led to some change, and then evolution, sexual revolution, all of these kinds of things, women take off.

Her research went further back. It went back to the 1700s, and what it revealed was that where we’re at today with female participation in the market and the workforce is where we were in the 1850s.

That declined when we went into the current labour model, which is, “I don’t pay my employees for output, I pay them for input of time.”

So now you have a woman who can produce 10 units in a day and a man who can produce 20, and this is Industrial Revolution if we’re thinking, but I’ve got to pay them the same amount of money.

Obviously back then they didn’t, and we’ve now got equal pay for equal work, which is fair and reasonable, and I support.

But you do have that situation where women were pushed out of the workforce because they were being paid for time rather than for output.

What AI is helping us to create — and this is happening a lot, I do it in the worldschooling stuff, we do all of these kinds of things — is it is allowing people to be valued on their output.

Now, it’s very different now to the 1700s: the knowledge economy, gig work, the complexity of society, workforces, all of those kinds of things. I don’t have all of the answers.

I think some people will struggle because they’re used to being paid for input. “I show up, I do the work, I get paid. I have a really productive week, I get paid. I have a really crappy week where I’ve got a hangover or I’m just not feeling it, I still get paid the same.”

The majority of people live in that paradigm, and that’s why they’re scared of AI taking jobs.

But if we look at the vast majority of human history, humans have used the tools available to them to create output and value, which has then allowed them to look after themselves and their family.

Yes, I think we will see a great shift back to that. I think it’s been underway for some time, just in terms of tools and the economy. Now AI forcing that upon a lot more people is going to be scary for many, but is a huge opportunity and actually better reflects who we fundamentally are as a creature.

Joe:
Before we wrap things up, I think we could sit here and straight up talk nonstop for the rest of time, to be honest.

I genuinely would rather be nowhere else than just literally sitting here and philosophising with you. I’m not even joking.

The one thing we haven’t talked about is payments and technology and Pinch.

Jacob:
Yeah.

Joe:
Talk to me.

Obviously, you’re a fan. You’re a Pinch partner. What is it about Pinch Payments that you like? Aside from the fact that we’re friends and you do it because you like me.

Jacob:
It’s twofold.

This is where I think a lot of the big concepts, which are a lot of fun, then I get to have those chats with clients, and they just go, “Okay, well, so what does that actually mean?”

First and foremost, payments. Small and medium businesses — every business, but particularly small and medium businesses — it’s a challenge. It’s a pain.

You do the work, and that’s the job done, is kind of the mindset. In reality, you’ve got to do the work, you’ve got to get the invoice out, you’ve got to get paid.

You don’t get paid to produce invoices. You don’t get paid to check debtors. You don’t get paid to chase debtors. That’s not the value you bring in whatever it is that your business does.

To be able to streamline that and to find some novel solutions that solve that problem for both the business and their customers and clients — and that’s where I think a lot of payment providers forget, is they serve one of those two but not both.

Whereas Pinch has absolutely come at that problem and gone, “How do we help both of these people so it becomes easy?”

So in a practical sense, that’s why I love and recommend Pinch, because you’re able to help the business with something which is fundamental, and you actually are able to make it easier for the customers to do what they need to do to get the value of working with that business.

Over and above that, the second reason why I love Pinch is because of that local, approachable element to how you’re building the business.

It doesn’t mean you have to be in the same city or the same country.

The growth that I have seen with investment and potential and those kinds of things in the product, in the years that I’ve been a Pinch partner, is huge, because that fundamental problem is universal.

The way you approach it, with some of those cultural contexts as a filter for dealing with customers, building the product, communicating the solution, is very different from how a lot of people in the finance space are playing.

To be able to support that and recommend that and trust in that is huge. Whenever you’re an advisor, whenever you make a referral, you’re putting your own reputation on the line, and that’s something that I’m happy to do when it comes to recommending Pinch.

Joe:
He’s not on payroll, by the way, everybody.

Jacob:
Not in the slightest.

Joe:
Look—

Jacob:
I’m going to see that clip more than any of the others, aren’t I?

Joe:
Maybe. No, probably not, because I reckon this episode was amazing, honestly.

The insights that you’ve shared today are going to resonate strongly with our audience. It’s going to resonate strongly with our network and our partners and our staff even, 100%.

Before we wrap things up, I will say, Jacob, I’ve met a lot of people in my career, and fundamentally, you are one of the best people I know, one of the best people I know in business, one of the best minds I know, one of the kindest men I know.

I wish you all the best in everything you do, and I think that you should have such a bigger platform, because the messages that you put out there and the things that you have to say are so important for people to hear.

Gender be damned, just people. Everybody needs to hear this stuff, because this is the way the world’s moving.

Jacob, thank you so much for being on PMID. I hope you enjoyed the talk today.

Jacob:
Absolutely. I hope I didn’t talk too much and not get some of that conversation out.

It’s always a joy. I’ll go to the opening of an envelope if they let me talk.

If anybody needs another talking head at a conference or a podcast to really spread that message, then I do it for the joy.

Joe:
Thanks everybody for joining us today. This was Jacob, Joe, PMID, episode three. Cheers.