EPISODE TRANSCRIPT

[00:00:00] We all come up with ideas. It could be riding the bike, it could be having a shower, whatever it is, the drive to work, and you’ll think of something and wow, that’s, that’s probably quite a cool idea. 

I wonder if that would work. What separates the average Joe with a good idea to someone who has the bravery to show up and say, I think I’ve got something here that’s worth investing in. 

What’s the difference in making that jump?  

  

Alright. Welcome back to Things Reasons, the Independent podcast for Australian IT leaders. That’s right. We’re back and it would be remiss of me. Not to ask my co-host Naran what he did on the weekend. 

Oh look, thanks for asking. Um, so every year [00:01:00] there’s a local bike race. It’s called Bobbin Head Classic. It’s organized by a dear friend of mine. His name’s Tony McClellan. He’s 88 years old. He still rides as well. He gets out on an e-bike. We sat behind him doing 60K an hour. He’s gonna get booked one of these days ’cause he’s, he’s got one of these, I shouldn’t mention that out loud, but here we are, allegedly. 

Uh, so he organizes this bike race. He’s about a thousand punters that enter the, the a 100K version. There’s other versions for friends and family and all the rest of it. And of that, I reckon there’s probably about 15, say semi-serious punters, uh, me included. Now the last two times I’ve won it. Oh, wow. 

Right. Somebody has to cross the line first. Um, so I went about the same thing on Sunday when we got up the first hill, the Bobbin Head Climb. Uh, there are only seven of us left. And then we carried that through to the second LA or the last climb, sorry, Akuna climb. There’s me and two young guys got away, couple of under 19 year olds and 47-year-old Naran. 

[00:02:00] And we took that almost to the line. Um, three guys caught up when the lights didn’t play nicely with us, and I crossed the line about half a wheel behind the first guy. Incredible effort. Was it number two out of a thousand? Something like that? Yeah. Utter dominance. Well, I expect nothing less. Yeah. Now my legs have been cramped and destroyed ever since. 

I slept for 12 hours on Sunday night. It was great. I woke up, it felt like I came outta hibernation. Perfect. I was half asleep all Monday. Perfect. It’s the best way. Well, congratulations on your, on your, uh, epic performance at the Bobbin Head Classic. And, uh, and obviously we do have a guest with us today. We today. We do have a guest with us today. I’d like to introduce Jason Serda. Now, uh, uh, I think a lot of our listeners will actually know Jason or know of Jason’s. It’s it. Overdue that Jason told way overdue on the podcast. 

Jason has spent 25 years at the sharp end of the tech industry, building businesses, scaling them, and selling them. He founded his fourth company, Blue [00:03:00] Fire and sold it to Global Tech Giant Dimension Data before taking on a role as global CTO at NTT. He commercialized over 20 enterprise SaaS products into hundreds of enterprise clients worldwide. 

And today he’s the founder and managing partner of Utility Group, a Sydney and US based venture firm that invests in advisors and accelerates high growth Australian tech businesses with a particular focus on helping Aussie founders crack the US market. That’s what we’re gonna talk about today. Come on, come on. 

And with $150 million invested. Over 50 companies backed and 13 successful exits under his belt. That’s a pretty impressive track record. He’s one of Australia’s most active and connected voices at the intersection of tech, venture and global Scale Up. Welcome Jason Serda. Thank you so much for having me. 

This is so good. Come on. Yeah, it is. Love it. It’s awesome. We’re pumped. We’re pumped. And day I’m gonna get us [00:04:00] going. Tell us one thing that we should know about you and one thing about the investment world. That’s a big secret that nobody tells you until you’re in it. Um, I think the personal thing is I want to be a kid in a toy store. 

So I think that I’ve worked very hard to kind of build and surround myself with amazing people, um, that I enjoy to be with every day. And, uh, we work relentlessly and, and incredibly hard, but the key thing is kind of surrounding yourself with really good people. And I think that that’s something that in personal and work goes hand in hand. 

Um, I think that I’m also a builder, so. You know, I refer to builder, like, I dunno if it’s, I liked Lego back in the day, you know, like getting, getting back when, when you were a kid. But it’s, the building doesn’t Lego of something, you know? And I think that that’s kind of extended. Yeah. Who doesn’t like Lego? 

Right? That’s right. But, but I think that, um, the concept here is, um, the building phase, which I refer to [00:05:00] from a work context to that zero to 50 million in a RR and operating in that space when businesses are, are, are still building, um. And then the second question is around, around investment. Um, just to let everyone know it, it is incredibly challenging, right? 

You have to be relentless. It’s about how many times you can get up from being knocked down. It’s never a straight line. Um, it does require absolute determination. And I think that from an investment perspective, um, you know, you really do need to be relentless. Mm-hmm. Yeah. Nobody told me that. So I kind of applauded my way along and kind of got knocked down and got back up. 

But, you know, you, you gotta be relentless. Mm. Well listen, it’s fantastic to have you on the podcast. I think, um, you’re gonna be able to tell a story here that for the most people they’re not really exposed to. I’m sure some of our audience has some exposure to the startup world. Um, there’s all sorts of lexicon and language [00:06:00] and process and things that you do that I think is a mystery to many. 

I, I’m sure we, we’ve all sat back in our armchairs at home thinking, oh, that’s a cool idea. I wonder if that would work on the open market. You know, I wonder whether I would have the courage or the bravery to kick something off myself and what would that involve? 

  

I reckon we might wanna reflect on the Australian market right now because it kind of feels like something’s going on here. 

Right. And I just wanna read out some stats. So let’s see, the first two months of 2026. Australia hit $503 million of funding across 25 rounds, and that was up 25% on the previous period in the previous year. So what’s going on there, right? Is this just a remarkable time to be alive? What’s happening now? 

Clearly there’s some obvious things that we can talk about that might have something to do with it, but what’s your take on it right now in Australia? It’s this fever pitch. What’s going on? I think, I think good businesses are always getting [00:07:00] funded, right? Full stop. Right. I, I think that the good ones, we’ve seen some of them like, you know, get tailwinds very quickly. 

Um, I think that Australia punches above our weight. So I think we are seen very positively from both, uh, us, US investors, US VC funds. Um, uh, Singapore right now has more family offices per capita than any other place in the world. Right. So you’ve got, you’ve definitely got positive, uh, um. Uh, tax benefits and other for those, for, for them to invest in the Australian market. 

So I think, I think that you, that’s, you start to see some of that and obviously, um, you know, they still have some, uh, that they wanna see those businesses enter the US market to address the size of market issue. Yes. But at the end of the day, I, I still think there’s an awful lot of interest. Mm. Um, and I think that, you know, the, uh, projected size of the Australian startup. 

Market is, is due to grow. So I think by 2034, I think, like you’re talking about, up to [00:08:00] 4.5 billion, you know, in CA 8.74% growth, like you, there’s definitely an inflection point that’s happening. Mm-hmm. You’re starting to see some, you know, some real traction. Yeah. Um, so, and, and you’re seeing a lot of active VC funds now, so a lot of opportunity, right. 

Well, I mean, the elephant in the room, let’s just say it for the first time on the podcast. 

  

I’m wondering how many startups you’re likely to see in the next six to 12 months that aren’t in some way related to artificial intelligence. Yeah, I think AI now is in everything that we touch, right? I mean, I, I was referring to this earlier today that, uh, my friend Claude and I, you know, a very close personal relationship, um, you know, my MAC Mini is, is operating using a Claude Cowork at home right now, replying to my emails like, you know, you can do more and more things now. 

It really is next level. So I think the expectation. On a, on a [00:09:00] startup is you need to embrace that. Mm-hmm. Which I think is challenging, right? Like it’s challenging for people that have been operating in a certain way to start adopting AI in the right way. That helps you keep. Your business is lean. 

Mm-hmm. You know, um, uh, here’s a statistic for you. Yeah. Um, they say to get to 10 million a r in an AI first world, you need 15 to 20 people. Right. In the old school way of operating, that would be 50 to 70 people to get to 10 million a r. Right. So, you know, how do you make the money last longer? I think that your friends and family around. 

Especially in Australia is longer. So what that means is, is that it’s like VCs and, and investors wanna see more traction before they invest. Yes. And as a result, I think the, the, the challenge with that is, um, you need the money to go longer. Got it. And you need to get more traction or, [00:10:00] or at least more validation points of. 

Of that, of that, just for our audience there too. And again, going back to the point that there’s, there’s a lot of sort of concepts and, and language here that’s an inherent to your life and the way you work. And you’re talking about a friends and family round. What’s going on with that? Friends and family round is usually the first money into any of these startups, right? 

It’s, it’s the where you’re gonna go to people that. Are gonna really trust you as an individual rather than the concept, you know? So I go to my dad and say, Hey dad, I’m gonna do this. You know, it’s that type of profile. Got it. You’re gonna go to your close relationships. Mm-hmm. And I think that, uh, once you get more traction and validation and revenue and other things ticking over, it’s easier to go to investors that you don’t know, um, for those follow on rounds. 

So I think that is, that is a longer process than what it was two years ago and probably, um. You know, now and longer than again, two years prior to that. So, and, and just to, just to follow on from that, a RR and annual recurring revenue. Annual Recurring revenue. So some of our [00:11:00] listeners will be familiar with that, but this is a common, uh. 

Measure of success in, in sort of B2B Tech or SaaS or, or, or these kinds of businesses? Yeah, it’s, it’s interesting, right? I mean, it, it, it’s designed around recurring revenue. So basically when you wake up the first of the month in any of these type of businesses, you know, you are automatically are already billing you MRR, which is your monthly recurring revenue. 

And then if you multiply that by 12, you get your a r. Yeah. And that’s, that’s a keen indication of, of. Success of of some of these businesses. And it’s interesting though, some businesses we see, they have maybe professional services that enable, they may have other CapEx that’s required in delivering the service, but often we’ll very only concentrate on the MRL or a RR. 

That’s the big prize that. That’s what that all these founders and investors are chasing. It’s, it’s, it’s the sticky part of the, you know, every, every, every, every month you start, you’ve got that revenue. Right. You don’t have to do anything to get it. Yeah. So I think that’s very compelling. You want to build big businesses with big MRR and big a RR. 

Got [00:12:00] it. Yeah. Jay, this stat around needing less people to, to start a business. Yeah. That’s, that sounds to me like, uh, investor expectations now. AI is now putting an expectation in terms of where capital is going to be deployed. Capital will be deployed into businesses that reduce their overheads through the clever use of ai. 

Yep. That has implications in, in startup land. It, it means, it’s, it, it should in theory, if you are, if you adopt AI and you have some maturity and, and invest in. In AI capability, that’s a good thing for your business. Is that also perhaps in in bigger capital markets or for larger organizations, uh, there’s a similar effect. 

So think about something that’s publicly listed. Billion dollar market cap. Is [00:13:00] there pressure now from investors on executives of those businesses to run leaner? Uh, and less headcount through the use of ai? Yeah, I mean, I, I think it’s, it’s every business needs to consider all those elements. I mean, even for running, you know, our, our VC funds, you know, we have, we have about 80 to 90, um, startups that would approach us on any calendar month. 

Um, those decks, um, go into our system. Um, AI will assess them against mandate against the funds. It’ll then complete our questionnaire if it doesn’t. Get all the answers from the client from their pitch deck. It’ll email them without me even being involved in order to ask them the questions that are missing. 

Yep. It then will go and write an investment memo and score it against the mandate and provide a recommendation. And then in addition to that, it’ll create a small, automated podcast That gives me a five minute summary of those points. Yeah. Yes. Before I get [00:14:00] involved, and then we look at the scoring, we try and determine if it’s on mandate and it, and it makes sense. 

But I mean, that’s just day in the life, right? Mm. But I’m now using ai my, well, I’ve been referred to my friend Claude. Um. You know, to do simple stuff. Yesterday I wanted to reprint all the logos on the entry of our office in Bondo Junction, right? And there’s 40 odd logos or something on the on the wall. 

And so I just went to Claude and say, Claude, can you go download all the logos for all our portfolio companies, print them in an A four on a landscape side and print them. So Claude went and built an app using Claude code and set up a thing unprompted, and then I just pressed the button and print. Okay. 

Yeah. Yeah. How cool is that? It’s pretty good. Yeah, it’s pretty good. And so there was a time when you’d probably, uh, get a grad or someone to go and That’s right. That’s, well muck around with that for you, right? So, well, yeah. Well, a hundred percent. I mean, um. I’ve got some mates that work for some institutional [00:15:00] investors. 

Yeah. Hopefully one of them is listening to this. ’cause I wanna talk about it with him afterwards. Yeah, yeah. Um, but I know for a fact that one of them, um, have a real bottleneck with human beings and the way they evaluate the opportunities coming in. Yeah. They have these single points of choke. Uh, whereby if the human being doesn’t have the time or the bandwidth to evaluate something, you can guarantee the op opportunities passing them by. 

And if they had a better way to do the things that you are describing, right. To ask the basic questions and get under the covers of every opportunity, such that when you do have time, you’re evaluating the right things in the right moment. Um, if you are not doing that, then they are inherently disadvantaged. 

Yeah. Right. And in your game particularly. Uh, you probably don’t wanna miss a really good opportunity, right? We we’re typically making one investment a month, and we will see 80 to 90 every month. Um, so even we struggle to read them all. Sure. So how are they gonna stay out of the crowd? Yeah. You know, um, I think is a, is a real issue. 

And I think [00:16:00] that, um. You know, they, they, AI is just part of the makeup, but it’s, it’s gonna be harder for conventional businesses to raise money if you don’t have that strategy and that consideration. Yeah. Right. I think, I think that what that translates to for me is investors are looking for very efficient use of their capital Yeah. 

To get a return. A hundred percent. And there’s a, and there’s a reasonable expectation now, and it’s becoming firmer that, uh, businesses will, will. Activate on those, those efficiencies with ai, it’s expected six or seven years ago. Uh, five years ago, even, like, there was, there was quite, people were quite comfortable in the forever burn where you were burning money burn’s Another good, good one, which is, we should talk about that losing, which is basically your, uh, your, your revenue. 

The burn is the difference between your revenue top line and your, and your cost base, right? So if your cost base is more than your, your top line revenue, you’re burning mm-hmm. And then there’s a percentage of burn. So [00:17:00] there was a time where. You were forever dependent on the next raise, which means that you had an acceptable level of burn. 

Yeah, and I think we are all happy to invest and spend money in order to get to a goal, but I think that the, the ability for us to drop below the line is only for a a period. Right. So before, um, I think that there was extended periods of burn that people would accept in the name of growth. Okay. Yeah. 

Yeah. It, it’s expected we’re, we’re gonna, we’ve got a war chest. We’re gonna spend the money, we’re gonna spend the money and, and that money’s gone. But we will increase the enterprise value of, of the company. Stay with us. Don’t lose faith. Yeah. That’s, we’ve got this. Yeah. And, and growth will solve All problems. 

All problems, yeah. And if we run out, we’ll raise again. And wipe away our sins. Yeah, yeah. Right? Yeah. Wipe away our sins by, by raising money and then select those sins never happen. Right? Yeah. But the truth of the matter now is, is that this current market doesn’t give you that same ability anymore. Mm. 

You can’t wipe away all your sins. [00:18:00] And I think as a result of that, um, you know, like a new, a new, uh, verbiage has come up, which is profit in months, not years. Which is another interesting thought process. So, you know, we’re happy to invest, but, but profit always needs to be on the horizon. And I think the takeaway there is you gotta build real businesses, you know, not businesses that are dependent on the next raise. 

Mm-hmm. And I think that that’s kind of where that’s evolved to. Mm. You know, um, so for the different startup leaders, ’cause I think going back to one of my original points here, and that is that. We all come up with ideas. It could be riding the bike, it could be having a shower, whatever it is, the drive to work, and you’ll think of something and wow, that’s, that’s probably quite a cool idea. 

I wonder if that would work, in your opinion, and based on all these leaders, these founders that you’ve seen and witnessed over the years. What separates the average Joe with a good idea to someone who has the bravery to show up to someone like you and say, I think I’ve got something here that’s worth investing in. 

What’s the difference in [00:19:00] making that jump? I, I, I think that, um, the best, the best, um, need to be arrogant and strong enough to choose to be a founder. I think that’s true. Um, but in addition to that, need to be open to work with others. You know, you don’t have to be the smartest guy in the room that you know that you can surround yourself with really good people and work together with others in order to reach the goals. 

They’re the ones that always win, right? Right. I think the ones that just want the money and have all the answers. And will one off to go do it themselves. Sometimes they will succeed, but in my opinion, the best ones are the ones that will work collaboratively, are open to other people’s feedback and will work collaboratively in order to drive those outcomes. 

You know, um, yeah, it’s, I I think that’s so true. Nobody can do it all themselves. Although, uh, I’ve seen some press recently suggesting [00:20:00] that perhaps one person. Uh, with the help of AI agents can do it all themselves, and we’re, we’re entering an era where an owner, founder, uh, could create the next billion dollar unicorn, Canva, or something by themselves. 

Do you, do you buy into that? Well, Y Combinator came out and just said that, you know, they used to mandate two founders, right? Technical founder and commercial founder. Now they’re saying, well, you can do it with one. Right? So that’s a, that’s a pretty big change. Um. But I, but I, I agree with you that, um, I still think like you need the right elements around you to set that up for success. 

Can, can I give you example? Uh, an AI specific example. They also say that now the modern AI first organizational startup has very good product management, has a, a solid data scientist, um, and then, and then has a rule set for how you want to build software. Right. So to the technical people audience out there, [00:21:00] you know, that’s a a Claude MD file, which kind of defines the rule set associated with how you build software using AI or in an AI first world. 

But if you have those ingredients, you don’t necessarily need a large scale development team, but you need to be clever enough in order to set it up well. Because the ones that do it badly, I can tell you what happens. You get lots of bugs all the time. It’s done very poorly. A poor client experience. You end up building stuff because it’s easy to build that people don’t want, you know? 

So how do you surround yourself with the right mix of people to help you get to those right outcomes? Yeah. So it still, it still takes a, a team and a diverse set of lived experiences. 10 million a RR now is 15 to 20 people now. Right. So you still, there’s still elements of. I’m doing that right. You know, we talk, I mean, look, culture’s a word that shows up all the time, right? 

Yep. All businesses strive to have a great working culture, and we hear things like, it starts from the top and culture eats strategy for breakfast and all the rest of it. John, are you and I both know, and [00:22:00] Ja, Jay, I’m sure you’re the same that it, it’s a lifestyle choice. This thing, when you commit yourself wholly to something. 

Um, it’s not a nine to five discipline. It occupies every aspect of your mind. And to be honest with you, balancing life with that as well, it becomes crucially important so you don’t lose your damn mind. Yeah. Right. You’ve gotta keep yourself room to relax and break the thought cycle and chill out. And there’s various ways that you can do that. 

Of course. That’s right. Right. But it’s super important. But I think if you are gonna commit yourself wholly to something like that, personally. I’d wanna be surrounded by people who are the same as me. Yes, I would want people around me that I trust 100% that are as driven as I am, because frankly, you need that to feel confident that you’re doing the right thing, right? 

You’re heading in the right direction, and you need to sense, check your ideas and to keep yourself grounded. And having faith in what you’re doing. And I don’t know how you do that on your own. That’s the kid in the toy store, man. Right? Right. That’s the kid in the toy store. Like [00:23:00] I think at the end of the day you have the, you have the right people around you to help you do this. 

It’s gotta be fun. Like, I hope my kids can find something that they love, that they’re amazing at, that they can make money at doing. But I, I really hope that they be the kid in the toy store, that they find something that could do it. I’m confident that I’ll continue doing this until I die. Yep. Right. 

Like, that is the way that I see it. Um, but a lot of that’s about the people that I do that with. Yeah. Right. But I think, yeah, there’s super clever people out there. You just gotta be open, you know? Um. And you know, this, this AI native stuff, right? Um, you know, a lean team of three to five people with the right AI stack can now accomplish what previously was done by 20 engineers. 

Right? That has huge implications. Does that, there’s so many places you can take that conversation and I think, uh, in. In my experience, and certainly we’ve, we’ve had lots of conversations about this on the [00:24:00] show, but also in, in people that Naran and I meet, I, I kind of experienced two, two different viewpoints on this. 

One is an incredibly optimistic view. Yep. Which is, wow. Like what a time to be alive, to be in business. Uh, human progress. Yeah. The, the ability to scale and, and accelerate. Uh, is like nothing we’ve ever seen before in human history. Yeah. It’s a huge opportunity. And then there’s the doom and gloom people. 

Yes. She says, oh my God. Well, what about the, so you just said that 50% of engineers aren’t gonna have a job anymore. How, how do you, how do you address those? Because you would meet two, those two types of people as well. What, how do you, how do you tackle that? I think it’s like a third, a third, a third. And I think the revolution is bigger than the internet, right? 

So I think a third will embrace and, and, [00:25:00] and drive that to success. A third will kind of deal with it and manage, and a third will have to change, right? Mm-hmm. And I think that’s kind of the way these big industrial revolutions typically have operated on. But, but I think it’s, it’s daunting. It’s daunting for everyone because, you know, like, um. 

The way that we have typically worked over the last 25 years, you have to be open to embracing change. And I think it’s gonna touch all aspects of, of how we do things. You know, I, I mean, I have this challenge now. We have people, we have put into some portfolio businesses that are still doing things. The way that they have done them for the last 25 years. 

And, and when I reflect on that, I’m thinking, oh geez. Like how do we keep the business lean? How do we maintain profits, you know, in this AI world and how do we remain competitive when our competitors are gonna be able to accelerate? The development portions are commoditizing if you know what you’re doing, that that’s the reality. 

So I think that, you know, that that AI implications. Uh, people need to be comfortable or more comfortable with [00:26:00] change, and I think people meet, need to be open to where they source to get help. Like we’ve spent huge amounts of time and energy and people power to try and help our portfolios solve the ai. 

What does AI mean for me? How do I execute on it? How do I remain lean like forever now, you know, it’s very hard for them to, where do they go for that? Yeah, I think that’s challenge. Real challenge. Yeah. Because a lot of. A lot, even like the, the big consulting firms, uh, are struggling with this as well. So it’s where, where do you go if, if you’re a founder and Yeah, they’re dropping people, right, John? 

Yeah, that’s right. And I don’t think many, um, many VCs, uh, had the benefit of having someone who, like you, who’s developed product and software for, for 20 years, who’s probably an early adopter of some of this stuff. Like I wouldn’t have built an agent to go and print the stuff. I probably would’ve plotted a, my natural instinct would’ve been to plot along and go and [00:27:00] snip the Yeah. 

Right. I’m happy to admit it. Like I, I’m, I’m, I’m getting there. Right. I, I’m not as advanced, but, but you need to actually push yourself and get uncomfortable. That’s right. And think about. Through that lens of how, how, how can I solve this problem with AI in my business? Because if you are not thinking about it, your competitors are, well, they’re the hardest things to change. 

Those, those inherent human behaviors and habits and things that we’ve built more important, our brain tells us to do it the same way again, because by God it’s worked for us in the past. That’s right. Right. Yeah. So why would you change it now, John? I know you are 40 something years old probably. Yeah, right. 

So, you know, change. Change is hard, right? Change is hard. I, I used to know a guy who taught me a lot about sales, and he said, um, human beings are naturally resistant to change. Yeah, absolutely. What would it take for me to, like if I ask you, when you get outta bed in the morning, which sock do you put on first? 

Is it the left one or the right one? Everyone will have a sock. They, they and, okay, so let’s just say it’s the left [00:28:00] one. Yeah. What would it take to get you to wake up tomorrow morning and put the right one on? Can I tell you a harder decision of my socks? It’s actually hard. Lot of my socks now have a left at a right. 

And the decision I have to face is when I pick up the right one to put it on the left foot. Do I commit anyway? I don’t care. Yeah. What do, do? I feel bad about it all day. Are do you believe? Do well. Do you believe they’re actually different? Yes, I do. Why else would they put the word on? Is that a conformist? 

Well, we think, but possibly I, I must be walking less comfortably. That must be, and so may maybe an agent can, can help you with that. Yeah. Make that decision. At the start of the day, you’ve ruined your whole day and so cha you’re right. And so change is, change for human beings is incredibly hard and I think people are naturally lazy as well. 

I don’t, and I don’t say that in a negative way. I think, you know, it’s like, like if they have to go to one extra element of effort, you know that that can be hard. Right? You’ve got so many different choices now. You know, now that we’ve got phones with screens, they have. So many different optionality to go [00:29:00] seek something else. 

Mm-hmm. Right. I think that’s so true. So, you know, I think that people need to embrace change. They need to be more open to it. But I guess it’s part of that, it goes back to the kid in the toy store. If you can surround yourself with amazing people that can help you solve some of these problems, like AI’s not going away, where are you gonna go to get it right? 

And, and, and find out how to do it, but do it properly. ’cause like, there’s also the, the ones that are, you know, you can build an app now. You know, in a second we can, you’re like, I, I had a startup that I, I was talking to them about an app I wanted to build, and they built it for me while I was on the phone, while they were presenting to me, they were asking me questions and they just hear the keys go, you know, and I think that’s, that’s the world we are in now. 

But you know, if you don’t apply. Product management and data science and deal with privacy and how you manage privacy and you don’t apply what I’ve been calling a rubric, which is the rule set for how you build AI software and AI first. Mm-hmm. You know, this rubric concept, it’s [00:30:00] rule, it’s just a rule set, right? 

A rule set around building software. You know, we like back in the NTT days, we had service layer, which was a. A bunch of Lego blocks that we reused when we were building software. Mm-hmm. And it eventually was like 40 bits of Lego. And when we wanted to build a new service, we used to assemble them, but we used to operate on, on a very specific rule set on how you build software. 

Mm-hmm. And so that rule set. Incredibly accelerated how we did things. It gave us, it made us nimble. We were able to move fast and we were able to reuse these components. And I think the same logic can be applied in the adoption of, of an AI first world. And if you take that type of concept, I think that you know, you’re gonna go far, right? 

Truly 

  

speaking of going far, if you’re a founder right now. You got a great idea. Yeah. And maybe you’re, you’re a bit bootstrapped. There’s another word for our listeners, which means you used your own money first. Yeah. Uh, [00:31:00] and you want to do your first raise. Yep. And maybe they’re, they’re coming to, they’re thinking about talking to utility. 

’cause they’ve, they’ve, uh, watched the podcast. Of course he has. I think that’d be a good idea. Come on. Yeah. Alright. Um, is this a good moment to make the leap. Is, is this a good time in the market to do it? Is the capital out there, like, are conditions favorable? And how would, how would you then evaluate a good business? 

Let’s say they made it through the ai, um, yeah, the gatekeepers. So maybe you’ve, you’ve touched on that a little bit. How, how would, what would, what would get you to decide to, to back that founder? I, I think that, um. There’s an amazing questionnaire that we talk about a lot. This questionnaire is actually, wasn’t actually my questionnaire. 

It was a questionnaire that we, that was developed from very many smarter VCs. I’m actually mentored by a guy out of the US like incredibly clever guy, [00:32:00] like, you know, he’s got four or 5 billion under management. Like he uses this questionnaire. Okay. It asks the questions that every VC wants to know. And when you have those initial conversations, we end up asking the same questions in multiple different ways to get to the answers that are on the questionnaire, right? 

So the questionnaire is readily available if you know where to look. If you come to me and you answer those questions and your crystal in relation to your, your thought process and answering every one of these questions, you know, who is your customer? Yeah. Who has the pain that you are solving for? Like, these are fundamental problems that help you nail the value proposition. 

The number of people come to me and go, we dunno who your client is. Right? Yeah. You got a great idea, but who’s gonna buy? Yeah. Who, who’s gonna pay you for that? Yeah. Yeah. And, and, and not only that, then there’s sustainable value. So some services that we see great value up front, but how do you sustain? 

Value over time. [00:33:00] Yeah. So that in six months, so a lot of people will sign up, get the value and leave. Mm-hmm. You know, they can’t sustain the value over time. So these are incredibly important questions that need to be considered. So I think part of my thought process, do your research, know your audience, fill in the questionnaire before you come and step in there. 

Because when you come into those meetings, those meetings are more about evaluation of founders. Are they good people? Are they willing to learn? Are they willing to do the hard yards? Are they relentless? You know, um, are they good people that are willing to work together to drive the right outcomes? You know? 

Um, and then I think the funding, you know, the best scenario if, if you want to go out to a pre-revenue vc, be prepared to dilute a lot. So dilution is. You sell more of your company, the more diluted you are. There’s more risk, obviously for the investor. That’s right. More risk. So they’re gonna want a lower valve of course. 

And as a result, you get my [00:34:00] more dilution. So if I was a up and coming startup at early stages, I would embrace the friends and family around. I would come up with and confirm a plan. I would raise the least amount of money that I needed in order to get to maybe a VC round. Yeah. So what do I need? What’s the minimum that I need? 

To get to that next round. Mm-hmm. Which is proof points validation, so that when you sit down with a vc, you’ve answered all questions. You can demonstrate traction, you can demonstrate some revenue, maybe not a lot of revenue, but some, and you know, you’ve got real paying clients that that really value what you do over time. 

And so I think that’s such practical advice. And again, with the lexicon. For our listeners who, who aren’t familiar VC’s, venture capital. So thi this is, this is money that people invest into businesses that are very early in their JO journey, which means if you back a winner, the rewards are better, [00:35:00] but the risk is higher for the investor. 

Yeah. A classic VC investor wants to get a 10 times return on, on their money. Right. Right. So they put a dollar in, they they’d like to get 10 back. Correct. On what typical term? Um, well, typically most VC funds are probably between five, five. To seven years, like investment cycle. Our, our investment cycle is seven years, but we depends on the stage of investment. 

If you go early, they tend to be longer. Yeah. Um. You know, uh, our new fund, we are gearing up for now, will probably aim to provide liquidity in three years. So it’s shorter Liquidity is when the shares turn into actual cash back in your bank. When we, when, when somebody buys the business and we get money back to investors liquidity events, which is, you know, which is very important. 

At the end of the day, our investors have an expectation that money is gonna be returned and that can’t be forever as well. You know, I had investors say to me, Jason, like, you know. I’ll be dead in 10 years. Like, you know, like that kind of [00:36:00] commentary. Look, at the end of the day, you need to be able to bring, bring money back into investors’ pockets. 

That’s key. Yeah. So we work hard, very hard at that. And sometimes those exits are engineered. What does engineered mean? We get on the phone, we call the likely buyers, and we hunt for exits. Right? Truly sell. Sell a business. Truly we’ll sell a business. A hundred percent. Yeah, a hundred percent. Um, so, um. You know, so that everything requires work and effort. 

How much is one of these meetings, like the show Shark Tank? I think, I like to think that it’s a little bit more personal than, than a founder, than Shark Tank founder shows up. Is it like you and three guys, sorry to all the Shark Tank people out there? Um. No, but I mean, I think I heard words like arrogant and confidence. 

That’s, that’s what I’ve taken away. Why should they be scared of this meeting? Like is it an intimidating meeting? No, no, not at all. Actually. Actually, I am more available and accessible than most people realize. I try and take an approach that Is that you or Claude? Let’s be clear. Well, well, yeah. Even [00:37:00] me. 

If you’re clever enough, you’ll get me. I just, yeah. But, but, but I think the thought, the thought process is. Um, I nurture the network. I work really hard. I, I’m always there to help others and I think that comes back in kind 10 times over. And I think that, um, I think that, you know, reach out, you know, and I’ll always try and help wherever, wherever I possibly can. 

Um, but I always appreciate the people that do, do the hard yards and do the research and understand their audience. Mm-hmm. You know, and, and, you know, answer the questionnaire and. And do all of that. But, but to, to answer your question around, is this meetings daunting? No. If anything, they’re relationship driven. 

You know, we sit down and we try and understand, we try to get to know people. Um, at the end of the day, it’s like a marriage, you know, you’re going into a long-term relationship with these people. And I think that the ones that we work very hard at have been very, have been long lasting relationships. 

Right. They’re the best ones. Yeah. So, yeah, it’s definitely [00:38:00] about the people. So if you’re, if you’re an aspiring founder, don’t be intimidated by this process. No. And you’re in more control Jono than, than you realize. I think sometimes it takes time to work out that, you know, you’re not waiting for somebody to give you something. 

It’s on you to to, to step up and take control of your circumstance. And I think people don’t realize that they’re more in control. You know, then, then they think they are, you know. Great. That’s true. Great practical advice, uh, fills us all with confidence. Our billion dollar side hustles. That’s right. 

They’re out there. They’re, they’re ready. And Jay, we’ve got, um, we’ve got three. Three quick fire questions for you. NA’s gonna, uh, hit you with them. Alright, all, let’s go get ready. Let’s, let’s go, let’s do it. Alright. Wes, expect honesty and transparency from you here, Jay. All right, mate. Sure, sure. I’m all out there. 

Let, this is a safe place. Let’s go. Safe place. Alright, let’s go. Go. Question number one, what’s the one piece of advice you’d give your past self before taking on a major tech initiative or investment? Perfect. One for Jay. Mm-hmm. [00:39:00] Yeah. I mean, be brave, be bold. Um, swing bigger. Swing big. Yeah. Like I think that, uh, knowing what I know now, I think having the courage to get out there and do that and do that, like, uh, I think it took me too long to realize, uh, geez, I, I can, I can really do this. 

Mm-hmm. And I think when I, when I stepped out of NTT, which was a big thing in 2019, um, you know, like, uh, when I reflect on that, that journey and you, you step out of a successful. You know, large scale job or whatever. Uh, I, I, I think that you gotta, you gotta have the confidence just and be relentless, right? 

And I think before I realized that I was back to where I was before I even knew it. Right. So, Jay, is this, is this, and it’s great advice by the way. Is this the luxury of someone who can afford to do it? Right. And I say that carefully ’cause you know, cost of living and people are working hard and they’re, they’re paying bills, they’re paying mortgages, right? 

Yeah. So, um, is [00:40:00] there a path for somebody who is more exposed to that than less as well? Yeah. Well, I think, I think like everything, like there’s, uh, there’s people around, you don’t have to do it by yourself, right? I’m a firm believer in surrounding yourself with good people, right? Yes. I think that’s, that’s, that’s a thing. 

I think that. You know, there are friends and family around you, um, based on the relationships you have that you can go to in order to support. And if these ideas are truly, truly good, you will get support from those people. Got it. And I think that you gotta be courageous. Give yourself an opportunity to, to prove out something that you have conviction in. 

Yeah. And if you sign up to a plan and you’ve got conviction in it and the people around you have got conviction in it, then I think you can really do it. Mm-hmm. Right? I mean, there is a little bit of crazy in there. Yeah. Yeah. Like, and, and I think it’s not for everyone, right? Let’s be clear. No, no. And I think, like, I’m a, I’m a tech investor, right? 

So I look for stuff that, um, we have an unfair advantage in order to invest in. So, you know, we are investing [00:41:00] in, in, in deep tech, tech, critical tech data centers, ai. Sure. Like this is stuff that we have built over time that we have a lot of experience in, and we have relationships. All around us. 

Everywhere. Yes. That we can kind of bring in. Yes. Yeah. Yes. And I think so we, we call that unfair advantage, but the unfair advantage is when we’re investing in something, we already know who we can sell it to. We’ve already got relationships that can materially help these businesses be successful. It’s mechanical almost to that point, isn’t it? 

Yeah. But invest in what you know. Sure. So to that person that’s coming out, looking to, um. You know, embrace something that they’re passionate about. Invest in the elements that you know really well. Yes. And that you have conviction in invest where you’ve got those relationships around you that can do that. 

You could do so, so well with Love it. You know, it’s that stuff. It’s so hard to have that depth. Yeah. You know, people do really well in, in that space. Yeah. Great advice, mate. Um, this is a good one for you. You spend a bit of time at the top, right? In [00:42:00] a, in a pretty big business. Yeah. Uh, what’s something that you used to believe in tech leadership that you no longer believe in you, you probably had some preconceptions about what it’s like at the top of when you got there. 

What don’t you believe anymore? I think, I think we were arrogant, right? Like, you know, we were back in the day we were building cloud before it was cloud. Yeah. So, you know, we were like, who’s these Amazon guys? Come on. We can do it better than them. Yeah, we do better them. You know, who we’re, I’ve heard this before. 

I’ve heard this somewhere else. You remember, right? I was there. We were there, we were there, we were there together. And you know, we, we, we were pro, we were arrogant, but we were bold and we still built a very big business in and around that, that, that tech. But I, I think that, um, you know, I see a lot of startups that, that. 

Show me this amazing UI and they get really excited about it. And then I ask a couple of key questions. Um, give me the login [00:43:00] statistics of your tech and you know, we can see either very low engagement or no one right logs in. And you go, what the hell is that about? Mm-hmm. Or let me ask you another, this is, this is one of the best ratios that just. 

Bring tears to many startup founders’ eyes. Um, what is the, the maximum money that you’ve raised divided by the amount of a RR that you have? Hmm. Maximum money divided by the annual recovery revenue. So you’ve raised a million dollars Yes. And you’ve got a hundred thousand arr, right? Say Yes. Okay. So what that is a determinant of is your execution capability. 

Hmm. So for every dollar that I give you, Aaron? Yes. How much a RR are you gonna give me? Keeps it honest, doesn’t it? Yeah. Come on. Cut. Cut. Hide from the numbers. Come on. You can’t hide from the numbers. And, uh, investors leave and, uh, go back to their nine to five. No, but I happy to have [00:44:00] tried. Yeah. But I, but I think, I think good luck to them. 

Yeah. But, but I, I, I think these, some of these, some of these statistics like investors are not silly though as well. No. But I think part of this. Is, uh, how do you get to the right place? But I think, look, the more informed you are and the, the better understanding you have is, you know, spend the money like it’s yours. 

You’re like, these investors are giving you, you, you know, they want you to spend it in a wise way. Yeah. And we’re entering a new world, AI first world that, um, you know, you want to be, you wanna be spending that money wisely. So if I play that back to you saying, uh, there was a time in, in perhaps your tech leadership career where you were leading. 

Perhaps with a bit of hubris or, or arrogance. And if, if you had a bit wiser now. Yeah. It’s, uh, focus more on, on certain metrics and be a bit more brutal about the, the value of what it is you’re creating. I’m, is that, is that, is that a fair, I’m, I’m a big [00:45:00] believer in, um. In product and the, and the power of product and the voice of the client and building things that have intrinsic value. 

And sometimes when you give technical people a screwdriver, we will build you something Jono just ’cause it’s fun. Because Yeah, yeah. It doesn’t mean it’s the right stuff. It doesn’t mean it’s the right stuff. Doesn’t, doesn’t mean that actually people want it. Yeah. But you know, like, but, and, and I think, I think there was some elements of that where we probably, uh, were too certain of our own beliefs. 

And I think that, you know, you want the right people around you to, to challenge you and to make sure that you’re building the right stuff. So, so true. Um, we had a, we had a concept called a zoo. Okay. You are familiar with the zoo, don’t you? The zone of the zone of uncomfortable discussion. Ah, yeah, yeah, yeah. 

Where we would sit down. In, in, in a friendly, you know, all friends. Yeah. And we would say, guys, we, we need to have some challenging conversations. So that kind of conversation in the event that we were thinking, we are building something that other people don’t want. That’s a pretty big topic. [00:46:00] And can, people can get very, very, uh, emotional about the Thomas. 

So we would call, we would sit down and we’d say, guys, we are calling a zoo and everyone just kind of park your emotions at the door, but we want to have some really tough conversations. Yeah. But the key thing is who is actually gonna tell you. That your baby is ugly. Mm. Okay. I think people need to be told. 

Right? So the baby’s sake No, but, but, but, but I guess the, the thought process is, you know, sometimes you need the right people around you to challenge you and actually stop you from making maybe some of the decisions that I made back yourself. Yeah. Right. That’s right. And um, and if you can do that and you can have these zoo conversations Yeah. 

That you can drive the right outcomes and you can get. You know, you can get to building a product that is truly exceptional. Alright, great advice. Jay. Here’s with the next, the last one. Last question. Last question. All right. Now this clearly, this is a one hour topic on its own right? So pick something random here, something that our, our audience may [00:47:00] not have thought about. 

What’s your gut check for spotting a good investment or walking away from a bad one? Is there something that just sticks out for you when you see, oh, this is shit already, I’m out. Yeah. I mean, I, I, I mean, I think it’s all about the people, right? I, I think you gotta start with that because you know, at the end of the day, your minority investors mm-hmm. 

You know, so you’re very reliant on the founders doing the right thing. You have to use influence rather than command and control. You know, PP people, like I always used to say, private equity people, private equity people can often breed bad behavior, right? But I think that they have some of, they’ve got the battle scars of working, you know? 

And when things don’t go right, that’s when things can, can be challenging. So I think part of it is, you know, in the world that I operate in where minority investors. We need to use influence in order to drive the right behaviors. Yeah, so a lot of that comes down to the relationship with the founders and making sure that we can have challenging conversations and that we can kind of work through any [00:48:00] issues. 

’cause nothing is a straight line. Every one of these engagements are riddled with challenges and problems. Got it. Does that mean that sometimes you’ll sit down and it’s immediately obvious to you, at least in the moment that you are not gelling with an individual and it’s gonna be a hard road ahead? 

Does that happen? Definitely. Right. Got it. And I’m usually pretty, I’m pretty casual, but I think part of that is, you know, we want to know that these people wanna work together. And we do get people, I have had many people that just said, look, Jason, um, you’re a nice guy, but I just want the money. And, you know, that’s just not the type of invest investor that I want to be. 

Yeah. So, you know, um, you know, the, the, the outcomes we get, um. Uh, it’s, it’s all about the people. Great. Well, you’ve done well on those questions. Thank you very much. Appreciate that. And, uh, look, I think that’s been a great episode. I’ve learned an incredible amount from you, Jay. Thank you very much. Thanks for having me. 

So before we wrap though, there is one thing we need to talk about. Oh, yeah. Let’s talk about the [00:49:00] rule of 40. You are watching your own podcast. What’s going on there? Well, I, I’m following you boys’ path to kind of get out. Did we inspire you? Come on. You did inspire me. You definitely, definitely. Right? Like, like we, we in 2026, we are, we are trying to, uh, uh, get out there and have something to say. 

Mm-hmm. Um, I think that we want to kind of, we, we’ve been poor in advocating for ourselves, right? Like we are good at advocating for our portfolio companies, but actually getting out there and advocating for ourselves. So I think part of this is we wanna get out there and have these kind of conversations. 

I feel like we’ve got something to say. I feel like we want to. We wanna hunt for our people out there, you know, investors and um, and. Portfolio companies alike, um, who are wanting to work together in order to go do great things? Yes. Um, in, in 2026 as well, we’re, we’re launching our new fund, which will be our later stage fund, which is about doubling down on the businesses that are working, [00:50:00] that are succeeding in their local markets, that are entering the US market and international markets. 

Um. You know, and we have an amazing portfolio of amazing founders that are kind of reaching that level of maturity. Get your pitch decks ready. Come on, Jay’s got coin. Come on, let’s go. Come on. So, so I think that, um, as much as we love to hear our own voice at times. I think it’s good to be able to get out there and, and try to share more of that. 

So, you know, you guys definitely inspired, you guys have been doing it for a bit and doing it so well, thank you. So thank you so much. You’re very kind Jay. Very kind, very kind. Well that, uh, we’re looking forward to the first episode of Rule of 40 Dropping. It’s coming out within weeks. At weeks. It’s, it’s coming. 

Oh, it’s already out now remember? Are we It’s already out. It’s already out in the future. Okay. Ah, we’re, we’re in the future. Where time travelers on things, reasons. Well, I, I, I learned a lot. I think there’s some great stats in there. I love, uh, I love the, the zoo meeting. Oh yeah. I think we need more of them. 

We do. Yeah. We need more of them. Product market fit is a real thing and [00:51:00] bad product market fit kills your business. So I, I, I love that one. And surrounding yourself with good people. Be brave. Yep. Yeah, exactly. Control. Swing bigger, right? Yeah. You control more than you think you do. That’s it. Get out there. 

Reach out. Happy to help in any way. Ah, thank you, Jay. Fantastic. Thanks. Jay. Narron, where can our listeners find the show? Wherever you find your podcasts? We are, of course, things, reasons. We are published on Spotify, on Apple Podcasts. We, of course, on YouTube. Good luck avoiding us on LinkedIn. Right? Come. 

It’s our platform now. All right. For our own broadcasting reasons, we’re everywhere. We are everywhere. We are, of course, produced by Pru Loon. Karina Aguilera, uh, we’ve got the wonderful Sofi as well out of, uh, south America. You can reach us at pru@thingsreasons.show Reach us for everything and anything. 

And thank you once again for listening in. Thanks listening. Thanks. So guys, thanks. Good everyone.  

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