Why Ego Kills Progress - Ray Yee with Lessons from Fintech

Product dies where onboarding breaks. Fintech product adviser, founder and podcast host Ray Yee shares Buy Now Pay Later lessons, audits without the blame game, scaling teams as risk increases, and why FastlaneIQ is helping charities modernise payments. 

You'll learn:

• Why “progress = happiness” in onboarding
• How to run low-risk experiments regulators can live with
• The people problem behind risk & compliance at scale
• When to admit your solution is wrong (and pivot fast)

Follow Ray @rayzworld on instagram and check out his website -> https://www.raymondyee.com.au

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Chapters

• 0:00 Intro
• 0:35 From Canada to Sweden to Melbourne: a global path into fintech
• 2:20 How failure led to Ray’s first fintech break
• 3:40 The biggest mistake founders make: obsession with the solution
• 5:00 The “Buy Now Pay Later” lesson
• 6:40 Scaling pains: the human side of risk and compliance
• 9:00 When things go wrong: leading through audits and recovery
• 11:50 Balancing innovation and regulation through small experiments
• 14:30 Fastlane IQ: building a fintech for good
• 20:00 Why ego kills progress

Transcript

Ray:
I think I see founders come up with an idea that they're passionate about and they become obsessed with the solution rather than the problems that they're solving. The human aspect of implementing change when your company grows is that when you're a small company and you have a few employees, there's less at stake to lose.

Loveth:
It's nice and refreshing to have a fintech that's not just trying to make money and actually trying to do good.

Ray:
And sometimes it's having those really difficult, direct conversations with the team on where the vision is for your company and where it's going to go in the next 12 months and checking in with your team to make sure that they're on board with helping you get there.

Loveth:
Hello crew, let's talk about the climb and not just the peak. I'm Loveth and this is Fail Tales.
So today I'm joined by Ray Yee, a fintech product advisor, the host of Founders and Funders Australia podcast, and also co-host of Super Host Down Under podcast. In addition, he's founder of Fastlane IQ. And to top it all off, he is a model. You really are a multi-dimensional and busy man, Ray.
Over the past decade, Ray's helped fintech companies across North America, Europe and Australia to navigate risk, regulation and product growth. What a background. Where did it all begin?

Ray:
I was born and raised in Canada. And in my early 20s, I moved to Australia. Lived for three years and decided to move overseas to Sweden and spent eight years there. And just moved back to Australia just before COVID.

Loveth:
Amazing. What's it been like coming back?

Ray:
It's very different. I moved to Sydney when I was in my 20s, and now I live in Melbourne. And it's different vibe, like art, culture, the food, big coffee drinker. Those are commonalities. We drink a lot of coffee in Sweden also. So I've been really enjoying my time here.

Loveth:
Nice. And FinTech, how did you get into that space?

Ray:
FinTech was an interesting one. I think sometimes your failures lead to other successes. I was working for a boutique consulting firm in Stockholm, and I didn't get promoted because my Swedish was not good enough. I do speak Swedish—just casually.
And so I didn't get promoted and all the new promoted employees were off-site. And one of our clients in Germany, in Munich, was struggling with the team. And so I jumped on and looked at the project and then wrote a summary with some action points on how to bring it back on course. And they wanted me on the project.
And that was a fintech startup out in Munich to help—pre-Apple Pay, that dates me—take mobile payments with your phone; your SIM card would actually bill to your carrier billing. So you can buy things tapping your mobile, and then all those charges would go on your phone bill. You just pay it, do that.

Loveth:
It sounds pretty standard today, but was very innovative back in that time.

Ray:
Back in the day, yes.

Loveth:
So you've spent over a decade working with fintechs and startups across 3 continents and onboarding new clients. You've seen what works and also what really doesn't. So to start us off, when you look back, what are some of the common mistakes you've seen founders or fintech teams make?

Ray:
I think I see founders come up with an idea that they're passionate about and they become obsessed with the solution rather than the problems that they're solving. And also, neglect how important onboarding is because if you can't onboard your customers, they can't try your product.
And so that became my focus to optimize the funnel for when you're spending money on marketing, it's important to make sure that your customers can get to becoming an active customer quickly and use your product and love your product. And so that was my focus.

Loveth:
Amazing. And often I find that technical people get very excited about the product and about the coding and what it looks like and the different dimensions of it and often don't think about the problem they're trying to solve. So I think that's a very, very good point to highlight.
And was there any particular project or clients that really shaped how you thought about risk and growth as that's an area you specialized in? Did you also have a specific thing that comes to mind, a client or project, when you think about that?

Ray:
Yeah, I think I was working for a very fast-growing buy now, pay later business.

Loveth:
We won't name them.

Ray:
I was working for multiple ones. I worked with one of the largest in Sweden, and then when I moved back to Australia, I decided to work for a different one.
And it's a balance with FinTech because you're disrupting an industry that has quite strict regulations, and it's making sure that you can comply with those regulations while still running a successful business.
And I remember trying to optimize a specific market to acquire new customers and choosing the solutions that would help meet our regulatory requirements, but then also sign up in a frictionless or low friction way.
And so I had an idea, we designed it, we built it. And as we're monitoring the onboarding, it just wasn't converting customers. The customers would stop at certain points and they wouldn't come back despite trying to retarget them through messaging.
And I think I held on to my solution too long that it was the right one or the best one. And after a while, I admitted that it was not the best way and regrouped with my team and chose a different solution. And we were able to increase our conversion by just changing our solution.
And I think that's really difficult and humbling sometimes to go to your team or your stakeholders and tell them that your solution didn't work and that you need to redesign it and spend more time. Those moments are the ones that I remember the most.

Loveth:
Yeah, but I imagine that the value of that feedback and you really thinking about making it work and for it to be sustainable... You have a lot of experience in different countries and I imagine that there were different cultural components looking at Sweden and Canada and Australia. Despite that, are there key commonalities you saw that were critical to success in onboarding new clients and retaining them over time?

Ray:
I think onboarding customers enjoy a frictionless, like a self-onboarding experience that's mobile friendly. I think that's common across all the geographies. You want to be able to onboard customers at any point in the day, and you want it to be as low friction as possible, the least number of fields to have to enter in order to sign up and be able to start using the product.

Loveth:
Of course, which sounds really basic, but I imagine it's quite easy to get lost in capturing data and wanting to know as much as you can to make that product more enjoyable for them.
So you've worked with companies that scaled really fast over time, as you've mentioned. What are some things that founders often underestimate when it comes to risk and compliance?

Ray:
I think the human aspect of implementing change when your company grows is that when you're a small company and you have a few employees, there's less at stake to lose. Your business is smaller in early stages.

Loveth:
You can make mistakes and take those risks.

Ray:
For sure. And as you grow and there's more monetary risk exposure, you then have to put more controls in place.
And the people who were part of that journey early on that had more free rein or more risk-loving appetite are now having to change their mindset and having to put in more controls and processes. And that's one of the challenging parts.
It's not the documentation that you need to put in place or the reporting to regulators. It's the human aspect of, are these people the right people in this stage in your journey to support the new policies that you have to put in place in the way that you want to run your business.

Loveth:
So do you find that you often have to think about the structure of the company a bit more and you might not phase them out, but including and hiring people who can better take on those roles or manage them in a way that they effectively align to the new policies?
How is that managed, I guess, because it's a very tricky time. They were with you in the cusp of building this new exciting fintech. And yeah, how do you then make sure you grow with them, but also scale in a very appropriate and legally sound way?

Ray:
I think when you plan out your business every year on what growth you're expecting, you have to look at the org structure that supports that and also the people who are going to help you get there.
And sometimes it's having those really difficult but direct conversations with the team on where the vision is for your company and where it's going to go in the next 12 months, and checking in with your team to make sure that they're on board with helping you get there.
And sometimes people are happy to find another organization where it suits their style better.

Loveth:
Yeah, they might just enjoy the startup phase more and not really the scale up or established company experience.

Ray:
And vice versa. There are people who would not join your company as a startup, but they now are great at scaling. Or when you get to a point where your growth slows down and it's about maintaining. There are people who are great operators in that space, but they would not be comfortable with the level of ambiguity early on.

Loveth:
For sure. And your point about having that open and honest conversation is a really good one because there's no harm or hurt there. It's just being honest about where you're at and the key skills and strengths you bring and whether it's going to be right for the next phase of the journey or not.
And when a risk decision goes wrong, let's say it's a data issue or regulatory hit or a product misstep, how do you help teams recover? And what's the right mindset that they often need to have to bounce back after failing to say?

Ray:
Well, earlier on in my career, the things I focused on are very different than what I focus on today. I think there was a focus on accountability and justice, finding out who was responsible for causing those issues.
And I find those really counterproductive later in my career and also is the wisdom of some of my mentors is to focus on gathering your team around the problem and supporting them and working through the problem rather than accounting blame.
And you can focus on the root causes post incident. But when you're in those moments, it's around building the right team who have the skills to get you out of it.
And I think in my past, there's been several audits with regulators and you really need to have the right capability and support in order to get through it.

Loveth:
For sure. And what does that look like practically? You have a fintech that there's some issues. How do you approach it? Do you have an example that pops into mind of something that's gone wrong and you had to sort of guide them through that without focusing on the person who caused it?

Ray:
Yeah, I think whether it's something that went wrong, or it's just clarifying or showing to regulators that you've done the right pieces.
For example, one of the audits that I had to do with a regulator, it's around identifying which teams are around the areas under question, and then bringing them into the case that we need to resolve—what evidence do we need to provide?
And then figuring out who are those people internally that would know those systems the best and processes.
And then being able to give them the capacity to investigate and gather the evidence for it to then meet the needs of the regulators.
So I think it's important to create the right team and support from management because these are priorities. And that allows the team to really perform. We have competing priorities all the time.
But these things that come up from a regulatory perspective are really urgent for the continuation of your business. So you need senior leadership to support, you need to identify the teams that would be impacted and responsible in those areas of your business.
And then have—just like a development team would have check-ins—you would have check-ins daily or weekly to look at the problems you need to address, the evidence you've collected.
And sometimes it's being honest that things do go wrong. It's more important to regulators that I've seen when you identify a problem that you have put in controls in place to minimize this from ever happening again.
Because things do happen—operational risks do happen and get realized. It's around how you resolve these problems and what controls you put in place for the future.

Loveth:
For sure, we're not trying to hide those problems.

Ray:
That's right.

Loveth:
Definitely. What really strikes me is with risk management, there's often a balance or a tension between managing the risk and not hampering creativity or innovation. How do you build and create teams and workspaces where there's safety and trust, but you also don't kill creativity and innovation which is needed in the long term?

Ray:
Yeah, very challenging. I think the more customers you have, the more challenging it is because you're impacting more people.
And one thing that helped me a lot when trying to innovate—removing friction while remaining compliant—is running small experiments.
So we'd build features that would reduce friction, and they should meet the regulatory requirements, and we believe that our users would like them. And we would trial it with a small group of users and see what the behavior is.
Because in many ways, you're affecting behavioral change. Whether you want people to continue using your product, you want people to stop certain behaviors, you're putting in features to change that behavior, guide them through a certain set of behaviors.
And by trialing these features with a small group, looking at the behaviors, and then making decisions on whether or not to continue, that's how you mitigate the exposure of everyone's been impacted, they don't like your product anymore.
And for the small group, you can be very selective of who these people are. You can potentially even bring them into the experiment so they know they're in an experiment.

Loveth:
And they might even enjoy being part of that at the forefront, yeah.

Ray:
For sure. And then internally with your team, it's around being honest when things don't go well—to reflect on what were the causes—and then brainstorming on what are the ideas they have on the next experiment moving forward to create that environment that not everything will be successful, but we're going to keep trying because trying helps us find insights and features that will change the behaviors that we want.

Loveth:
Yeah, and improve your product. So it sounds like it really also comes down to culture of the organization and the team.
And some ways I've seen some companies try to inject that is having like entrepreneur of the week or month or failure of the week or month just to promote that culture of trying and failing and not being too complacent in doing your everyday job and to continuously look for opportunities to do something new or to improve the product offering.
So yeah, I think things like that are quite nice to give comfort for the teams that they can fail and try, and it's okay. It's almost sort of celebrated.

Ray:
Yes, and many organizations have organized hackathons where teams get a day or half a day off-site or even in the office where they identify problems in the organization that they want to solve. And then they find those who are passionate about that problem in a very structured way, in a very supportive way.
They're able to feel seen and heard about their ideas, find the people who are passionate about the same idea, and then work on something that would improve it slightly or completely, and then have their stakeholders support this process and see their presentations of what they come up with.
I think it's a good opportunity to step away from the day-to-day and reflect and then also use your creative juices.

Loveth:
Yeah, something like that is killing several birds with one stone because you're team building, you're being creative and innovative, and you're probably achieving new products or ideas by the end of it. Sounds like a great hackathon.
And you've talked a lot about onboarding, which is where a lot of fintechs often then lose users if it's not done properly. What are some of the biggest mistakes you've seen in the onboarding process, especially when you look at startups and then you compare it to scale ups, which is sort of a very different, I guess, lens?

Ray:
The most frustrating thing for me during onboarding is an unstable flow. So whether the pages don't load, it takes time, or they ask for all the information upfront.
Because for me, I think progress translates to happiness. And so if you're spending 10, 15 minutes filling out a form online on your mobile—

Loveth:
Who's going to do that? I would personally click off and be like, no, thank you.

Ray:
Right. If you don't feel any progress, then it's very easy for me to lose interest and abandon because I don't know the value of your product yet.
So a lot of it for me is staging—what information do we need at each stage? And could we optimize for the user to see the value in the product before they have to provide more information?
I think there are many fintechs who do this really well: you sign up and you get to see the product in full, but not use it. And then you try to use it, and then it's like—you can use this, but we need to know this about you. And then before you can use this function, we just need to know a little bit more about you.
And I think that's a good way to balance the friction with the value, because what's in it for the user is something that solves their problem. And if they're not sure that your product serves their problem, they don't want to give you any more information.

Loveth:
No, just so you can spam them with a problem they don't want.

Ray:
Exactly.

Loveth:
Yeah. And sort of pivoting to today, you've recently founded Fastlane IQ because you're clearly not busy. What is Fastlane IQ and what is it hoping to achieve?

Ray:
One of my previous clients who's now my co-founder, we were brainstorming on problems we wanted to solve in the world. I think one of the challenges I see is that—payments for me has been part of my life for a long time. I worked in banking, I worked at Westpac, I worked with fintechs in three geographies.
But for businesses, payments is only one aspect of their operations. And payments is quite confusing. And I wanted to help businesses find the right products and services for them at the right price.
And having worked in payments, I understand how the commercials work— which things can be negotiated, which things cannot. But also specifically, we're helping charities with collecting donations online.
I think charities often are overlooked because sometimes they may be a fraud target. Other reasons are that due to regulation, they are not charged the same high fees or the same fees as other businesses. So I feel like they're neglected and I want to support them.
And so we've now signed several charities in Australia and we're helping them optimize their payments.

Loveth:
Amazing. And what are your future ambitions with Fastlane IQ?

Ray:
I would love to expand to other verticals. I think something that is important is to keep providing businesses some of the latest tools.
So for example, we see NPP, which is a new payment platform. I'm sure you've used PayID before.

Loveth:
Yes.

Ray:
There's PayTo, which supports like direct debit but using the same technology. So we see new capability come out in market, and it's important for me to provide businesses multiple methods to support their customers in collecting payment.

Loveth:
Amazing. It's nice and refreshing to have a fintech that's not just trying to make money and actually trying to do good. So well done.

Ray:
Thank you.

Loveth:
Before we wrap things up, I'm really keen to hear—and I know that you're also now a fintech founder. If you were to advise a first time fintech founder or yourself right now, what would you tell them to get right from day one?

Ray:
To only get one piece of advice.

Loveth:
Okay, two or three.

Ray:
I think for fintech, as the name says, it's technology and financials. And I think many fintech startups often undervalue the importance of having a founder who is tech savvy.
I think we definitely can have teams prototype and build something that you can use to present to investors. But it's really important—and I've seen it go wrong—when you offshore your development without someone in the company who will stay there for the length of the journey.

Loveth:
Okay, so you just have a rich businessman or woman who has the money and the idea and they just offshore it to someone else to build it for them.

Ray:
Yeah, someone who in-house cares about the problem you're trying to solve, cares about your business, cares about technical excellence, who will be there on the journey with you.

Loveth:
Skin in the game.

Ray:
For sure. I think the other one, which is so challenging, is checking your ego.

Loveth:
Why do you say that?

Ray:
Because I think it's sometimes—and personally, I've held on to ideas longer than I should have, solutions—and it becomes a distraction from pivoting and optimizing.
And so it's being open to what the data is telling you about your ideas through your testing, rather than being fixated on the solution—being obsessed with the problem.

Loveth:
Correct. And being open to finding out that your solution is wrong and maybe you need to pivot or change the core aspect of it. Because you just want to achieve the goal you're trying to achieve. So focus on not the solution, but the goal, I guess, and the problem.

Ray:
Absolutely.

Loveth:
Those are some great nuggets of gold. Thank you so much, Ray.

Ray:
You're welcome.

Loveth:
It's been a great conversation.

Ray:
Thank you so much for having me.

Loveth:
This is Fail Tales, real stories and real lessons. If you enjoyed this episode, share with a friend and subscribe wherever you get your podcasts. You can also watch the full episode on YouTube and make sure to follow us on Instagram, TikTok and LinkedIn to see more clips and get behind the scenes content. Bye.