
Not many people can say they’ve mastered both air traffic control and the financial industry, but Steve Monaghan isn’t most people. A former commercial pilot turned banking and tech innovator, he’s spent three decades reshaping industries with a mix of high-altitude vision and grounded strategy. Whether in the skies or the stock market, one thing’s for sure—Steve doesn’t just follow trends; he charts the course.
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A
Hi everyone. Welcome to our show. Chief Change Officer, I'm Vince Chen, your ambitious human host. Our show is a modernist humility for change, progressives in organizational and human transformation from around the world. Today I'll be chatting with Steve Monaghan. 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 caught 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.
B
Foreign Steve 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 the 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 out 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, et cetera, 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 Kreider's Law, et cetera. 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 Compaq Computer Corporation. That was also an equally interesting journey working with some really brilliant people. My last role with 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 non profitable 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 called a ledger and we used barcode on the phone for mobile payments. Today you use QR codes. Then from corporate investment banking in Citi, moved across opening up a consumer finance division for a CBC bank and then moved to Japan where I got to run a consumer bank and did a turnaround of that business during the Lehman crash. Then I moved across and became an entrepreneur as I've done a few times before. Actually ended up going to Singapore where I became the first Chief Innovation Officer at dbs, helped get them on the path to digital transformation. Then moved across where you and I met at AIA where we run the AIA accelerator and created Hong Kong's first unicorn and then moved across after that to being an entrepreneur again and building the first insurance company underwriting system with AI. And then after that moved across became a digital officer in Saudi Arabia for Riadh bank and then moved back here to Japan after Covid to establish really a focus on advisory investment. I've invested in a bunch of startups and now starting my next big thing which is a swing for the fences player to transform economies. No more Small stuff.
A
Wow. It's fascinating to hear how your career journey has evolved, particularly how you've navigated from aviation to technology, software and hardware, then deeper into various sectors of finance and entrepreneurship across different regions and countries. What's the core motivation that keeps you moving forward, especially in taking on the ambitious projects?
B
Very simply learning. If I distill it down as I reflect on all of those transitions, it was really about this insatiable thirst for learning that I have. Not only that, but being able to work with others and inspire them to get that same thirst for learning. 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 across 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 insuretech. It's all just tech. And all you've got to do is work out how you use that tool set 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.
A
Your personal website kicks off with a bold statement, Learning the foundation for Sustainable Competitive Advantage. You 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?
B
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 and 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. You really don't know. And so repeatedly, most people would be scared to do something new. Absolutely not for me. I thrive on it because I know I'm going to learn something. And failure is just part of that journey. And that's well established in the business world. I've gone on to fail at many things, but each of those things has led me to the next big thing. And I think that's the most interesting part of my journey.
A
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?
B
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 obtained, I'm learning from the other side of the equation.
A
It's really insightful to hear how you've managed 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 no knowledge and acceptance? And what role did learning play in this process?
B
What I distilled it down for 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 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, homework in hr. And so we came up with this program of learning, venturing and capital. So how do you take learning so people are no longer fearful that they know that they can take advantage of that technology and transformation and transform, you know, that learning into venturing experiential learning which is the most powerful form of learning and then into capital for acceleration. How do you really start scaling things? And when you bring that approach to bear it works from the board to the branch really that focus on learning, making sure people are understand getting enthusiastic about change. And in the technology industry change is a constant. We are forever planning to do things that don't where the tech doesn't even exist today. 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, et cetera. 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 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 cost 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 if you give people that understanding and how they can use it as a multiplier such as aix, then gives that growth mindset, which is very important for everyone in business.
A
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 stick and the stronger the impetus needed to push you through a transition. People generally resist change unless it's thrust 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?
B
Absolutely. It's a very simple formula, and I think that you're absolutely correct in summarizing it that way is people don't like being told what 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. And I think that's always been the mark of success of an innovation group or any innovation officer is to have other people take ownership of those ideas and be humble enough to let go and appreciate that other people can actually take it to a level that you mightn't see because you're relying on their expertise. And I think that's the greatest compliment you can place with any employee or colleague is to really try and bring out the best of both sides so you're actually getting the sum of all versus I'm going my way and take it or whether you like it or not. And that's just completely destructive. This is just Game Theory 101.
A
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?
B
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, you know, the 20 to 30 year olds could do, and made technology so simple to use that it actually engaged from 3 year old kids or 3 month old kids that could swipe a screen all the way through to grandparents that would previously not touch a device. And 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 BENQ 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. 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.
A
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?
B
In this particular instance, the average tenure of someone in that, 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, you know, light bulb switch, it's more a network. So when you understand the network, you're in a better position to actually understand the implications and to craft your question in a way that takes into account some of the constraints of the network or some of the opportunities or accelerants of a network. So that experience is pretty hard to come by. It's why if you look at most AI, what you want to do is take the experience and expertise and encode it. And this is the perfect nexus of that. You are getting people that when they retired in the past would retire with all their knowledge. Now we've got this enormous ability to encode that knowledge and take advantage of it and then pass it down. Younger kids tend to ask simpler questions. They're still learning the basics and the ropes and trying to understand. They've generally got very limited exposure in terms of geographic exposure or business division exposure. Because I think the one other thing I've appreciated as I've got older is humans can't scale. We tend to specialize. We're an accountant or we're a marketing person, or we're a finance person. And very few are able to really succeed in multiple spheres of business. But technology's horizontal technology goes across all of those silos. So one of my favorite sayings is the value lies between the silos, not necessarily in the silos. And that's why the older people definitely have an advantage, because they're not constrained in getting those questions into an AI, which can then draw upon that reservoir knowledge to actually return more valuable responses.
A
They really bring a hands on perspective to the table. These employees have been in the trenches, experiencing the pain points of the workflows long before technology was introduced. They've lived through the problems, which means they are uniquely positioned to see where technology can solve issues or where processes might actually benefit from a more human touch. This blend of human insight and technology leads to a more seamless integration. What I would call a true artificial intelligence, where it's not just tech, but it's more combination of machine and human working together.
B
Yeah, absolutely. These are the core things that you try to get across in any sort of digital transformation project. You want to get some sort of level of emotional engagement. Right. So that's the whole experience side of the equation. Then you want to make things very simple for your customers. And simple or simplicity is cognitive. One plus one equals we all know the answer. So the quicker you can get people to make decisions by giving them the right information, then that's obviously an advantage. And then the last part is effort minimum type, swipes and swipes to actually execute your decision. I refer to that as ese or easy. Right? Experience, simplicity and ease. And they're the three objectives that in any digital transformation that you set as your primary objectives for the customer. That ability to interact with emotion, simplicity and ease.
A
AI is always a big topic. But let's switch gear to talk about your next big thing. You've mentioned to me that you're working on something really, really interesting and meaningful, groundbreaking, if I can use this word. Tell us more.
B
I've been lucky to work for some of the largest corporations in the world and transform them digitally. Now I'm trying to focus on economic transformation. I think one of the things as you look around new generations of technology is that a lot of people forget that the constraints which they take for granted no longer exist. So that's the case today with economics and finance. We have people that are paid in Asia usually every month. Right. And if you actually look at the constraint of that or the belief that's just the way it is, it's actually quite wrong. If you consider that an employee joins a company and doesn't get paid for 30 days means that they're essentially accredited to the company for that 30 days. And what's happening is while they're giving their cash flow to the company to take advantage of, they're actually usually burdened by much higher cost debt. So if you look at that, you're taking very high cost debt to substitute for low cost debt which results in direct capital destruction both at a company and economic level. 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, interacting with governments and regulators and corporations, et cetera. 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 bigger 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.
A
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 supply them through the ups and downs?
B
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 times. And if you don't have integrity, there's nothing built 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. And I've had and currently have a couple of founders that I've worked with and invested in that are actually having quite significant mental health issues. One has completely stepped away from the business at the moment and for the right reasons. And I'm completely supportive of that. And I think that if we look to who we are as human beings, I often take a view which most VCs I think would disagree with. But I actually think the human being is far more important than money. I think that you want to keep these brilliant folks operating, but you don't want to push them over the edge. And I think there's so much pressure in just being an entrepreneur that most folks from the outside don't understand it. Anything can go wrong. I had one company recently that had signed agreements and then all of a sudden, at the 11th hour, the financial institution reneged on them and all done right. So then now they're facing near bankruptcy. Hopefully they'll fight their way through and they're certainly closing some pretty big accounts at the moment. So there's hope. But you can't imagine the toll when you've invested so much of your life into a startup. And in one case that I went through about a year ago, my founder had spent seven years building it up, only to have he had award winning product in the health tech field, very long long tail to get there, had great reviews from some of the best institutions on the planet, but he wasn't yet profitable. And when funding dried up, his company evaporated. The mental toll is just immense because you're not just responsible for yourself as a founder, you're responsible for everyone that works for you. And I think that a lot of people underestimate just how, how onerous that responsibility is. The fact that I have had founders that have mental health issues to show their focus and their feeling is behind that humanity, and I think that's a great thing.
A
Some investors might be less understanding when it comes to situations like this, but you seem more open and empathetic. Perhaps that's because of your diverse experiences in different roles and capacities. There's a common notion among entrepreneurs that discussing mental health issues openly with investors, co founders or even team members might shake their confidence in your leadership or influence their investment decisions. From your diverse perspective as an entrepreneur, as an investor, as an innovator in big corporations, how do you handle this? How do you address the stigma or reservations that some might have about mental health in a high pressure environment of startups?
B
I think it's very common. My response to folks that have that issue is saying is very simply, you have the wrong investors. I think that if you deny people the ability to share, you're actually being part of the problem and actually more likely to lead to the failure of your investment than if you actually have a tolerance or more importantly, an alertness to what's going on. When you see something going wrong in the business, the first thing I ask is always, how are you feeling? And I've had many entrepreneurs that have run. These are like quite well funded startups that come back and say that you're the only person that's asked that question. And if they don't have that outlet, then the chance of that mental health issue either spiking or becoming quite serious actually increases. Everyone knows that founders often suicide. I don't want any of my founders to suicide at all. That would be the worst possible outcome for the company as an investor and for me as an individual. And I think that we need to be far more open to actually being empathetic. If you look at it going back to ese, it's one of the core principles of everything to do with customer interaction and with founder interaction. That emotional quotient is the foundation of everything that we do in life. If you look at there was a book written by Paco Rabanne many years ago which I took to heart is why people buy and they make decisions with emotion, justify with logic and take action when it's easy. Ese this is what drives trade and economies, et cetera. And but more important, at the end of the day, this is all about people and people matter.
A
There's a really important point to emphasize. Mental health issues are not exclusive to entrepreneurs. They affect anyone from entrepreneurs to to employees to CEOs. I've personally faced mental health challenges three times myself, with two of those occurring during my time in corporate roles. It's something many of us might encounter regardless of our position.
B
I asked one of my staff to take leave because it was very obvious that they were having mental health issues and that leave made a world of difference. And that person went on to become very successful and I won't narrow it any further, but was very successful in the career that followed and that was not. That person stayed working with me for quite some period of time before they left and found a bigger and better role. If you don't give people that opportunity to get back in balance, then I think that everyone loses.
A
Absolutely. Before we wrap up this conversation on mental health in particular concerning entrepreneurs, what advice would you give to them or even to those who want to support other entrepreneurs with their mental wellness? What are some possible solutions? You see, perhaps some solutions might be tech driven, while others could be more about creating supportive communities or programs. How can we help entrepreneurs not just move forward, but also regain their confidence to become more resilient, allowing them to fully leverage the brilliance. Confidence, resilience and brilliance. A perfect formula for entrepreneurs.
B
I think the major thing for me is community and that could be private or public, but I think having someone that you can speak to, someone that who's always open and non judgmental is really the first piece. And if you have that and you're willing, it's a two way street, right? You've got to find the people that can be supportive for you. And equally you've got to be open to be real with them and if you're prepared to make that commitment and you found the right people to support you, then I think a lot of these problems can be avoided.
A
Steve, earlier in our conversation you highlighted the critical role of learning in your career transitions and how it's been a sustainable advantage for you. Reflecting on your passion for learning through reading, particularly on complex topics such as AI, could you share how you believe this habit of deep focused reading has impacted your mental wellness? Additionally, do you think there are specific ways that engaging with such intellectually stimulating materials can help others manage their mental health?
B
I'm a bit of a nerd. I tend to follow topics that that are interesting. So one of or interesting to me or the fill a gap in my knowledge. If I look at who's inspired me in the world of finance, it's gotta be Demar Duran. When looking at things like when I wanted to learn how to be a better marketer, I read a copywriting book by William Strunk that said that a sentence should contain unnecessary words in the way that an engine has no unnecessary parts. But there are many books that I've loved reading. But recently on the topic of AI, Mustafa Sulaiman, who was the co founder of DeepMind, wrote a very interesting book which was nothing particularly new but very well researched and very well put through in a very coherent manner to actually explain some of the risks and opportunities of what's happening with AI. And I think that too few people actually understand the ramifications of the directions that we're headed. And as an example, I wrote an article for Forbes, I think in 2016 talking about AI and just saying that we weren't ready and in Forbes refused to publish it because it wasn't positive. They seem to have been positive on lots of other things that haven't worked out very well. But I think realistically Sulaiman paints a very good picture to how you must have a very balanced view of AI. As an example, the ability for people to create bioweapons is now going to the home. AI gives you this enormous compute capability and the ability to do things in ways that weren't possible before. And so the risks around that are growing now. We've dealt with very similar risks in the past as we've evolved with technology. But now we're entering a new sphere and a new age where bioterrorism or the dark side of what happens with AI can be just as bad as the good side of AI. With almost every week we read about new types of cancers being addressed, et cetera. And in the background behind all of these medical developments that we see, it's because of people in a very smart way, scaling AI and understanding permutations of everything. So Solomon gives a very good example of a company that was looking at chemical compounds and had set the gain function for toxicity to be very to be zero, right to find what are the best medicines that you can actually ingest the that actually achieve curative results. And then as an experiment they turned the function from 0 to 1 and looked at the most toxic outcomes and they actually invented new compounds that didn't exist that were more toxic than VX gas. So I really encourage people to go and have a very balanced reading portfolio. One of the books that that I found most intellectually curious lately is Lemon's book.
A
That's a wrap. Thank you so much Steve. I'll surely get you back here very soon. As long as you have time.
B
My pleasure, Vince. Thanks for having me.
A
Let's take a moment to recap the key insights from our conversation with Steve. Here are eight crucial takeaways. Number one Learning is the key to unlocking transformation. Not just for organizations, also for personal career development. 2. Embracing learning means embracing failure. The real value lies in what we learn from those failures. Number three Having an outsider's perspective can be incredibly valuable, offering a fresh, untainted view and adding a new dimension to problem solving. 4. Change is always met with resistance. The trick to overcoming this opposition is by transforming a no into a know knowledge, helping people understand the why and how of change. Number five Empower people to own the change process. This approach helps eliminate their fear and can drive change more effectively and extensively. 6. Mature and experienced employees bring significant advantages in the era of AI. Their firsthand experience with workflow pain points before technology intervention places them in a unique position to integrate technology seamlessly and enhance processes with a human touch. 7. Pay attention to mental wellness. Whether it's for employees or entrepreneurs, everyone can be affected by mental health challenges in one way or another. 8. Maintain a balanced reading portfolio is essential for staying informed, curious and effective in continuous learning. Thank you so much for joining us today. If you like what you heard, don't forget, subscribe to our show. Leave us Top rated reviews, check out our website and follow me on social media. I'm this Chen, your ambitious human host. Until next time, take care.
Episode #195: Steve Monaghan: From Flying High to Finance Disruptor — No Seatbelts Required
Host: Vince Chan
Release Date: February 23, 2025
In this episode of Chief Change Officer, host Vince Chan welcomes Steve Monaghan, a dynamic leader whose career spans aviation, technology, finance, and entrepreneurship across various global markets. Vince introduces Steve by highlighting their first meeting in Hong Kong around 2015 or 2016 when Steve was the Regional Director at AIA, managing a health technology accelerator. Their professional relationship deepened as Steve took on roles such as a venture coach and judge for the University of Chicago's Global New Venture Challenge.
Notable Quote:
Vince praises Steve's authenticity and resilience, stating, “Steve embodies authenticity. He is consistently successful and resilient in the face of setbacks, largely because I believe he is always true to himself” (00:12).
Steve Monaghan details his unconventional career path, starting as a commercial pilot in Australia. Balancing piloting and running a company, Steve self-taught technology, particularly spreadsheets, which provided a competitive edge by optimizing processes and reducing turnaround times. This foundational skill set led him to roles in financial modeling, software, and hardware industries, including pivotal positions at Dell and Compaq Computer Corporation.
Key Highlights:
Notable Quote:
Steve reflects on his drive, “learning... being able to work with others and inspire them to get that same thirst for learning” (07:12).
Steve candidly shares his numerous failures, emphasizing that each setback was a stepping stone to his next success. He recounts his challenging start at Dell, where his capabilities were initially doubted. Overcoming this, he immersed himself in learning, rebuilt complex models, and leveraged technology to gain a competitive advantage, which became the foundation for his future endeavors.
Key Insights:
Notable Quote:
Steve emphasizes the importance of experiential learning: “It's like riding a bike. You can study it all you want, but until you actually apply it... you really don't know” (09:00).
Having lived and worked in multiple countries—Singapore, India, Saudi Arabia, Hong Kong, Silicon Valley, and Japan—Steve discusses how his status as an outsider has been both an advantage and a challenge. This unique vantage point allows him to offer fresh perspectives and innovate by integrating diverse cultural and business insights.
Key Points:
Notable Quote:
Steve shares, “I have a view, an external view. I'm obtained, I'm learning from the other side of the equation” (11:46).
Steve explores strategies to mitigate resistance to change within organizations. He posits that fear of change often stems from a lack of understanding. By transforming a simple "no" into "know"—through education and clear communication—leaders can foster acceptance and enthusiasm for new initiatives.
Key Strategies:
Notable Quote:
Steve articulates his approach: “My full role has been to turn a no into a K N o W... to make that happen the way that we made that happen” (12:24).
Challenging the stereotype that older employees are less tech-savvy, Steve highlights the unique advantages they bring, especially in the context of AI. Their extensive experience enables them to ask more insightful questions and understand complex networks, enhancing the integration of technology with business processes.
Key Insights:
Notable Quote:
Steve states, “The value lies between the silos, not necessarily in the silos” (22:30).
Steve delves into the critical issue of mental health among entrepreneurs. He emphasizes the importance of community and support systems in managing the immense pressures of building startups. Steve advocates for empathetic investor relationships where mental well-being is prioritized over financial outcomes.
Key Points:
Notable Quote:
Steve underscores the need for empathy: “Anyone can face mental health challenges... you have the wrong investors” (32:24).
Steve shares his current focus on economic transformation aimed at optimizing capital flow across companies and supply chains. By addressing inefficiencies, this initiative seeks to increase GDP by approximately 20%, with significant social impact by alleviating financial burdens on the poorest employees.
Project Highlights:
Notable Quote:
Steve describes his project as his “legacy project” with immense social implications (25:12).
Concluding the discussion, Steve emphasizes the importance of emotional engagement, simplicity, and ease (ESE) in digital transformation projects. These elements ensure that customers and employees alike feel connected, understand the changes, and can interact with new technologies effortlessly.
Key Takeaways:
Notable Quote:
Steve summarizes his approach: “Experience, simplicity and ease... are the three objectives that in any digital transformation that you set as your primary objectives for the customer” (24:54).
The episode wraps up with Vince recapping eight crucial insights from his conversation with Steve Monaghan:
Final Thought:
Vince encourages listeners to subscribe and engage with the podcast for more transformative insights, emphasizing the ongoing mission to help individuals outgrow themselves and achieve exceptional outcomes.
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This detailed summary captures the essence of episode #195, highlighting Steve Monaghan's multifaceted career, his philosophies on change and learning, the importance of mental wellness, and his visionary approach to economic transformation.