Steve Monaghan flips the script on innovation culture: experience isn’t a relic—it’s a strategic edge. As General Partner at FinMir.ai, Limited Partner at True Global Ventures, Independent Non-Executive Director at RAK Bank, and former Chief Digital Officer at both AIA and DBS Bank, Steve brings a cross-industry view forged through decades of deep transformation. From aviation to fintech to AI, he shows how age fuels better questions, sharper pattern recognition, and global insight in a world obsessed with novelty. Whether he’s building Asia’s first unicorn or designing systems that could restructure entire economies, Steve makes one thing clear: for Gen Xers tired of being underestimated, age isn’t a liability—it’s leverage.Built to Learn, Not to Fit“I wasn’t hired for my experience. I was hired for the questions I knew how to ask.”Steve’s journey—from pilot to pricing guru to product architect—was never about titles. It was about learning faster than the system could teach him.From N-O to K-N-O-W“People don’t fear change. They fear not understanding it.”Steve shares his framework for flipping resistance into insight. At DBS, it became a model: learning, venturing, capital. The goal? Turn skeptics into innovators.Legacy Is Not a Headline“This isn’t my next startup. It’s my swing-for-the-fences play.”Steve’s current project could restructure economies by eliminating capital inefficiencies in payroll and supply chains. It’s big, bold—and designed to help the people most hurt by broken systems.The Advantage of Age in the Age of AI“Older workers know how to ask better questions. That’s the advantage.”Forget the ageist myth. Steve explains why mature employees are becoming AI’s secret weapon—and why experience, not just coding, is the multiplier.Mental Health Is Not a Risk Factor—It’s a Design Factor“You can’t build resilient companies without resilient founders.”As an investor, Steve supports founders with integrity, grit, and humility. That includes stepping back when needed—and being asked, not judged, for how you feel._________________________Connect with Us:Host: Vince Chan | Guest: Steve Monaghan --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.12 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>140,000+ are outgrowing. Act Today.<<<
Chapter 1: Who is Steve Monaghan and what is his background?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Our show is a modernist community for change progressives in organizational and human transformation from around the world. Today, I'll be chatting with Steve Monahan.
I first met Steve back around 2015 or 2016 in Hong Kong when he was the regional director at AIA, one of the leading insurance groups in the Asia Pacific. He was running a unique health technology accelerator at the time. Later, I invited him to be a venture coach and judge for the University of Chicago's first-ever Global New Venture Challenge, hosted right here in Hong Kong.
Since then, he's moved to Tokyo. We've called up a few times, both in Japan and back in Hong Kong. To me, Steve embodies authenticity. He is consistently successful and resilient in the face of setbacks, largely because, I believe, he is always true to himself. He walks the walk and talks the talk. A real leader and an incredibly inspiring speaker. How could I not invite him to the podcast then?
Just how inspiring is he? Stay tuned for the next 30 minutes and you'll find out. Good morning, Steve.
Chapter 2: How did Steve Monaghan transition from aviation to technology and finance?
Good morning, Vince. How are things? I began my career in Australia, started as a commercial pilot and started to learn technology as a function of that. So in many ways, much of my career actually was founded then and there. I used to fly 22 hours a day and I'd run the company during daytime and fly at night.
And as a method of getting some sleep, I taught myself technology, how to use spreadsheets when that was a brand new technology. And it enabled me to get this advantage over my competitors that enabled me to, A, achieve my objective of getting sleep and be able to get quotes in people's hands immediately that would usually take most companies a few days to go and fulfill.
From there, I became more interested in the business side than the flying side. And then I started teaching financial institutions how to use spreadsheets and then started building models that people would build front ends around and payrolls, etc., And moved into the software industry and then moved into the hardware industry with Dell Computer Corporation.
I was on their startup team for Asia Pacific, developed pricing models, all sorts of things. So spreadsheeting really gave me my basis in understanding tech. And then, of course, creating hardware started to teach me about the importance of Moore's Law, Metcalfe's Law and Crider's Law, etc. So as I built the business across Asia Pacific, I moved from Australia into Malaysia.
And then my final role with Dell was in Korea. I set up the Asian Product Development Center for Compact Computer Corporation. That was also an equally interesting journey, working with some really brilliant people. My last role with Dell with Compaq was to set up the Indian business, which was failing miserably. And so I had a very kind boss that said, jump on a plane on Monday to India.
You've got to either fix or close the business. And closing is not an option. So I was given this tremendous opportunity to go and spend some time in India. And I went out to market, looked around and found out that who we thought our competitors were. Everyone said it was impossible that we can compete, but it made no sense because we were the world's biggest PC company.
How could you not be cost efficient? So after looking at how the market worked, how customers interact with the technology, et cetera, went back, financially modeled everything, worked out a better supply chain model to Dell, and then recreated the products to fit the financial model.
And when we did that, we zoomed from number four in the market and unprofitable to number one in a quarter and stayed that way for the next 10 years. That really gave me the basis for moving into finance. I went to Citigroup asking for help to redo my financial supply chain. They weren't so sure what a financial supply chain was, so I moved to Citi.
I developed their first mobile payments patent in 2001, something that most people use today. I called it multi-entry bookkeeping. Today, you call it a ledger, and we use barcode on the phone for mobile payments. Today, you use QR codes.
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Chapter 3: What motivates Steve Monaghan in his career journey?
So many of the folks that have worked for me have gone on to be quite wildly successful chief innovation officers of insurance companies, etc. And they've also transitioned industries. So one thing that you find that's common across everywhere is business is business and technology is technology. There's no such real thing as fintech or health tech or insurtech. It's all just tech.
And all you've got to do is work out how you use that toolset within your business practice. So every time and every transition, every country I went to, there was always something new to learn about that culture, some insight that they had that I didn't. So I learned as much going into each of those roles as I was able to bring to the table with that past experience.
Your personal website kicks off with a bold statement, learning the foundation for sustainable competitive advantage. He also openly mentioned, I've succeeded and I've failed always learning. Could you share with us some candid insights about times when things didn't go as planned?
Specifically, could you tell us about what you've learned from these setbacks and failures in your career and innovation projects?
There's been so many failures. I'll start at the beginning. When I joined Dell Computer Corporation, I had gone through a three-hour interview where the national sales manager had picked apart my resume. I was joining as a product manager. And he basically challenged every line in it. And at the end of the interview, he was so frustrated because he really didn't want to hire me.
He said, I can hire someone with 10 years experience. Why should I hire you? And I said, if I had 10 years experience, I wouldn't be applying for this job. About two months later, I'm sitting in the office at 11pm working on this monstrous multi-spreadsheet model that generates pricing once a month. And I put my head in my hands and I thought, oh my goodness, I've oversold myself.
I really just didn't think I could do it. But I went back and I read every single book I could on pricing, accounting, valuation, everything. And I went in a very short period of time, went back. rebuilt all of those models.
Instead of making them just disparate pass-offs, I actually integrated them all, created configurators in Excel, started being able to do forecasts instantly, which was something that would take days usually. And then I started to look at how you would use for technology the way it's really meant to be used is to arbitrage time.
So how I could actually get a time advantage over my competitors, exactly what I'd done in aviation. So for me, and that experiential learning is the most powerful form of learning was actually became the foundation for everything that followed. So it's a little like riding a bike. You can study it all you want, but until you actually apply it and put it together, you can get on the bike.
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Chapter 4: How does Steve Monaghan handle setbacks and failures?
And I think that's the most interesting part of my journey.
You've really lived and worked all over the globe. Singapore, India, Saudi Arabia, Hong Kong, Silicon Valley, and now Japan. Everywhere you've been, you've been the outsider. How do you think this foreigner identity has shaped your approach as a leader driving change?
Part of that learning process was always I was the outsider. I was the outsider from a company perspective, from an industry perspective. I was the outsider from a cultural perspective because I was from a different country. I've been an immigrant in most of the countries since my 20s, right? So I've lived as an immigrant.
So I've always been the outsider, which gives me an advantage and a disadvantage. And the advantage is I have a view, an external view. I'm not tainted. I'm learning from the other side of the equation.
It's really insightful to hear how you've managed to change and overcome resistance in your roles. Could you elaborate on how you've tackled the challenge of people's natural fear of change in your work? In particular, when introducing new technologies or business models, how have you transformed a simple no? into know, knowledge, and acceptance. And what role did learning play in this process?
What I distilled it down from is the reason that people are fearful that they don't want to change isn't that they don't want to change. Actually, I think everyone wants to change. We love going on holidays to new places. We love having different meals every day.
But if you're going to place a minefield in the middle of that journey and place everyone at risk, no one's going to go and make that journey to do that new thing. And that learning helped me distill into the reason that you get the most no's is because people don't know. They don't understand. They haven't learned. They don't really see what that new thing is.
My full role has been to turn a no into a K-N-O-W. So a no to a no and then into now. And that's really the role of any business person and any innovation officer or any digital officer is to actually go and make that happen.
The way that we made that happen, and it was particularly successful at DBS, where my partner in prime I'd worked with in Japan, and he was the head of talent management for DBS, a gentleman by the name of Tom Patterson. Tom worked in HR, and so we came up with this program of learning, venturing, and capital.
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Chapter 5: How does being an outsider influence Steve Monaghan's leadership?
But we know we can get there and we know that we can actually have that growth mindset to go and scale the business off the back through either price cutting or taking advantage of cost reduction, etc. That doesn't exist in most industries. So that was a huge advantage for me coming from the tech industry into the financial services industry.
The moment you could start helping people understand how the tech industry worked and why their margins keep increasing while everyone else's keep decreasing was because they're driving depreciation costs as well as value in appreciation of features. So they're creating their own markets and then they're driving and making huge amounts.
So if you take Google, it was probably five or six years ago, increased the personal storage from one to two terabytes. has been stable for five or six years. But in reality, the cost per gig has actually plummeted. On average, it halves every 18 months. So their margins continue to improve while your experience of that service doesn't necessarily change.
Once you understand how tech works and apply it into new businesses, and you can give people that understanding and how they can use it as a multiplier, such as AI, then gives that growth mindset, which is very important for everyone in business.
The motto of a podcast is make your laws of change. Steve has shared his own laws of change on his website, which I'll link in the show notes to those interested. He outlines three core principles. First, that change is always met with opposition. Second, that implementing change requires a forceful effort And third, that the larger the organization, the greater the force needed to enact change.
These principles aren't just relevant to organizational shifts. They apply to personal transformations too, such as career changes, something many of us are facing today. Take the first principle, change is always opposed If you are in a stable job with a decent income, why risk what you have for the uncertainty of change? The second principle states that change requires force.
Whether it's due to layoffs or needing to relocate, the push and pull factors must be compelling enough to drive the change. Finally, similar to large organizations needing greater force to change, the higher you are in your career, the more you have a stake, and the stronger the impetus needed to push you through a transition.
People generally resist change unless it is stressed upon them unexpectedly and without clear reasoning, logic, or alternatives, as many experienced during COVID. However, if the conditions for change are managed well, involving and consulting those affected throughout the process people can and will embrace change. Don't you agree, Steve?
Absolutely. It's a very simple formula. And I think that you're absolutely correct in summarizing it that way. People don't like being told what to do. They like to be part of the journey. They need to understand. They need to be brought along on that journey and then given the ability to contribute to it and actually enhance upon it.
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Chapter 6: How does Steve Monaghan transform resistance to change into acceptance?
So speaking of innovation and change and how it's sometimes resisted or embraced. You and I previously discussed an interesting case involving a bank in the Philippines. You mentioned that a particular segment of the staff there, the more mature, often overlooked group, actually contributed significantly to innovation efforts after you engaged with them.
I wanted to bring this up because there's a common belief in the tech world that older employees might not be as tech savvy as their younger counterparts, which can lead to ageism in the workplace. From your experience, can you share how you've seen mature employees contribute to innovation And what are your thoughts on overcoming this legacy mindset that sometimes holds back valuable talent?
Sure. Actually, I'll start back earlier.
I think when Steve Jobs introduced the iPhone, that he actually moved technology from something that only the young could do or that the 20 to 30-year-olds could do and made technology so simple to use that it actually engaged from three-year-old kids or three-month-old kids that could swipe a screen all the way through to grandparents that would previously not touch a device.
If you look at it in the same context now with what we're seeing with generative AI, it's now making technology so much more accessible to people that would have felt somewhat alienated by technology in the past.
So the bank that you refer to in the Philippines, one of the observations that I shared when I was working with their leadership team was that this is the first generation of technology where actually older people have an advantage because they know how to ask better questions.
And I think that's a very profound point because a lot of the younger kids may actually be somewhat disadvantaged because they don't know the right questions to ask. At this stage of generative AI, I think that makes quite a significant difference, as we know, with what we see in prompt engineering, etc. Older people do have an advantage.
Why do you think the younger people don't know how to ask relevant or right questions as opposed to the older members of the team?
In this particular instance, the average tenure of someone in that leadership team was ranging, I think, between 27 to 40 years. And they'd worked across every element of the business. So being able to ask the right questions, if you think of technology as not an individual light bulb switch, it's more a network.
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Chapter 7: Why are mature employees an asset in tech innovation?
And if you look at it, if you're able to actually optimize that across companies and supply chains and economies, we feel that you should be able to increase GDP by about 20%. So it's a very big play and it relies on knowledge of legislation, finance, supply chains, a whole range of different factors and looking for those inefficiencies between each of the silos.
And so that's where I'm really focused on now and been working here and interacting with governments and regulators and corporations, etc. And the new year has started well, so we'll see if I can bring it to take off. But as with everything in my career, it's a big mountain to climb. And this time it has such incredible social impact.
If you look at this capital inefficiency, it actually hurts the poorest in our poorest employees and the poorest in our communities the hardest because they pay the most for alternative debt while they fund their employers cash flow. This just makes no sense to me in a modern and real time world. This is an initiative that I've undertaken with a small team.
So I'm just part of the team that's going and developing platform, et cetera, to go and kickstart it. We've been spending a lot of time talking with banks and trying to educate them and with regulators and trying to educate them and with politicians, et cetera. So I sit there as part on the execution, part the investor behind it. We'll be going for capital at some point. This is my legacy project.
This is the one that I really want to happen because it has such an enormous social impact.
That sounds exciting. I can't wait to see the progress. It's bound to have a huge and tremendous economic and social impact. When you're ready, let me know and I'll send in my resume, okay? Now, you mentioned you are deeply involved in both executing and investing in this project. This brings me to another critical issue many entrepreneurs face, mental wellness.
Could you share your observations or experiences with your investees on how they manage their mental wellness How do you support them through the ups and downs?
Yeah, absolutely. When I look at investing in entrepreneurs, I usually look for humility, grit and integrity. And if you can bring those magical things together, if you're not humble, you can't learn. If you don't have grit, you won't see through the hard times. And if you don't have integrity, there's nothing to build on.
So if you try and take those three things and look at it, I get to work with a range of quite tremendous entrepreneurs. And every single company that I've invested in, either myself or I was an LP in a global fund, every single company comes across a point of hardship. And it's incredibly mentally taxing on some of the founders.
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