The Exchanges

Q Why did you start Lightspeed? Did you, you know, the family there, no background in restaurants. No, like, oh, I saw my grandmother cooking over a stove and I fell in love with restaurants. Why did you start Lightspeed and what was that aha moment?

A The environment that I grew up, so obviously there's a big background in the early Mac and, and, uh, being a part of that Mac ecosystem, whether it was the, the early developers or the dealerships, you know, before there's Apple stores, there was dealerships. Uh, and I grew up in those dealerships. I was doing tech support. I was working in them. I was, you know, major, major little nerd, nerdy dax. Uh, but I started building software for those dealerships. You know, they were building a lot of their own software. Each dealership was building their own software, um, usually in this tool called FileMaker. And it was usually the business owner building their own custom FileMaker. It was like a, you know, an access, Microsoft Access database, homegrown. They were terrible. So over time, I was trying to build more and more software for these dealerships. And if you think about what an Apple dealership would look like, it is, it really is Our ICP, our ideal customer profile at Lightspeed is a complex inventory centric retailer with high value inventory, with serial numbers, multiple locations, purchasing across multiple stores and multiple currencies. It's everything we do as a, as, as a, it's everything we offer in the Lightspeed software today to retail. So I was cutting my teeth, building software, you know, contracted software for these dealerships between the ages of 15 and 28.…

AI assessment note: “that moment of, okay, I'm not going to build another custom piece of software”

Q Why did you decide then was the right time? Seven years in is a long period of time. When did you, why did you decide then and what revenue were at when, when you decided to raise? I'm fascinated.

A We were at ten million, um, And, uh, it was actually, you know, the, those folks that I just mentioned Square and, and, and, uh, that, uh, it was a New York POS company called Shopkeep. They were, you know, there was new players coming onto the scene. Um, cause at this point we were, we were competing with legacy black plastic POS systems. It was easy, you know, to compete with them, but then other, other, you know, uh, uh, POS systems that were more forward looking, more cloud-based, uh, Like square, even though it was very simple at the time and like shopkeep, which was an iPad POS, which we had, but ours wasn't cloud-based. They started to come out and even though they were very simple, they had hundreds of millions of dollars being funneled into them. And it started to be, I went from a, from the perspective of like, Hey, I have no finance background. I haven't really looked for investors too. Maybe it would be maybe not a bad idea. And we didn't actually go out looking for VC money. We, um, we did, we were, We were masters of the trade show. We'd done mackerel for many years, and then we switched to doing NRA, which is National Retail Federation that happens in, um, in New York. And in, in 2000, it was 2000, uh, January, January of 2012, a number of VCs come to our booth, uh, looking for the future of retail, because every retail player is there. And they identified Lights…

AI assessment note: “We were at ten million, um, And, uh, it was actually”

Q I put, I put it in this group of vertical staff nerds and I was like, what's going on here? And they were like, oh, golf's a massive segment, Harry. I was like, what? And so, so I'm just fine. Like golf is a big segment for light speed.

A So it is a retail hospitality hybrid, right? So if you think of a golf course, uh, it's got retail pro shops and it's got hospitality, um, Uh, venues on site as well. Uh, and so what there was a partner of lightspeed called chrono golf integrated the lightspeed systems, the retail one and the hospitality system and, uh, and put, put them together and built a, uh, over top of it, they, they built like a golf management piece, right? So, uh, managing tee times, managing, um, you know, memberships, all of that. And so that was like a really interesting independent software vendor that kind of took all the different Lightspeed components, as well as some e-commerce components and other things

AI assessment note: “So it is a retail hospitality hybrid, right? So if you think of a golf course”

Q So, but I just find it funny, because people often struggle, and I'm like, fuck, I have so many that I could say for myself. Do you think you found yourself as a leader at some point? I know that sounds really weird and spiritual, and I don't mean that, but like, I think you learn who you are in leadership.

A Yeah. I didn't think of myself as a leader, you know, and that, that two year period I spoke about where it was like four AM in the morning, that was me transitioning from me being that independent software guy, uh, one man show. Just a little bit scared of my team. Like this team, the software was selling really well and this team was growing. I was like on the third floor of this apartment building. I rented the second floor for Lightspeed. Um, and that second floor started to grow, like, There's lots and lots of people starting to show up there, you know, because we were selling, the revenue was coming in, and we were, we needed more folks. Eventually, I had to start talking to these, these people, and I, I was forced to be a leader, and we talked about the dreamer that I was as a kid. I was like an introvert, you know, and I think Lightspeed's pushed me to be able to articulate a vision, to be able to communicate, but it didn't come naturally. And I think that's something that I think a lot of people that, that, um, that are, that are in startups that might be passionate about solving a problem, then they have to figure out, okay, now how do I be a leader? How do I lead these folks? How do I inspire these folks? How do I pivot these folks? How do we, how do I convince the market? How do I talk to media? This is, it's, it's not necessarily something that everybody knows how …

AI assessment note: “Eventually, I had to start talking to these, these people, and I, I was forced to be a leader”

Q Why did you start Lightspeed? Did you, you know, the family there, no background in restaurants. No, like, oh, I saw my grandmother cooking over a stove and I fell in love with restaurants. Why did you start Lightspeed and what was that aha moment?

A The environment that I grew up, so obviously there's a big background in the early Mac and, and, uh, being a part of that Mac ecosystem, whether it was the, the early developers or the dealerships, you know, before there's Apple stores, there was dealerships. Uh, and I grew up in those dealerships. I was doing tech support. I was working in them. I was, you know, major, major little nerd, nerdy dax. Uh, but I started building software for those dealerships. You know, they were building a lot of their own software. Each dealership was building their own software, um, usually in this tool called FileMaker. And it was usually the business owner building their own custom FileMaker. It was like a, you know, an access, Microsoft Access database, homegrown. They were terrible. So over time, I was trying to build more and more software for these dealerships. And if you think about what an Apple dealership would look like, it is, it really is Our ICP, our ideal customer profile at Lightspeed is a complex inventory centric retailer with high value inventory, with serial numbers, multiple locations, purchasing across multiple stores and multiple currencies. It's everything we do as a, as, as a, it's everything we offer in the Lightspeed software today to retail. So I was cutting my teeth, building software, you know, contracted software for these dealerships between the ages of 15 and 28.…

AI assessment note: “I'm not going to build another custom piece of software... We're building Lightspeed here.”

Q thing to me, which is we were so close to the customer, because we couldn't afford customer support, and we had to just do it all ourselves. And I asked them this question. If I had given you five million on a twenty-five million price, like you could probably get today if you go to the Valley, Would Lightspeed in this case have been the same as it is today?

A I don't think so. It probably, it probably could be something different and as, as, as successful, which I don't know what it would look, maybe necessarily look like, look like, but those seven years of bootstrapping, like we're, we're in our profitable growth phase where we're now, you know, out of this growth, growth, growth at all costs phase, and we're now into balancing growth and profit. That's like the early, early first seven years where we were profitable. Uh, and we, we ran the company and grew with a great degree of balance. And, and I think that that's, that those are, that's a great part of our DNA. We also had a really good seven years of, of really solidifying our identity. And that, I think that strong sense of identity and, and who we are and what we represented and, and how we did business, um, helped a tremendous amount when we took VC money, when we went public and also when we, uh, did M and A. Because when you bring, when you merge other companies into your company, you have to have a strong sense of identity to allow other companies to be able to flourish, um, as a part of your company and not try to suffocate them out of insecurity, you know? And so that, that I think that strong sense of identity has allowed Lightspeed to do a lot of the, the, the big, the big things it's done.

AI assessment note: “I don't think so. It probably, it probably could be something different”

Q I put, I put it in this group of vertical staff nerds and I was like, what's going on here? And they were like, oh, golf's a massive segment, Harry. I was like, what? And so, so I'm just fine. Like golf is a big segment for light speed.

A So it is a retail hospitality hybrid, right? So if you think of a golf course, uh, it's got retail pro shops and it's got hospitality, um, Uh, venues on site as well. Uh, and so what there was a partner of lightspeed called chrono golf integrated the lightspeed systems, the retail one and the hospitality system and, uh, and put, put them together and built a, uh, over top of it, they, they built like a golf management piece, right? So, uh, managing tee times, managing, um, you know, memberships, all of that. And so that was like a really interesting independent software vendor that kind of took all the different Lightspeed components, as well as some e-commerce components and other things

AI assessment note: “So it is a retail hospitality hybrid, right?”

Q thing to me, which is we were so close to the customer, because we couldn't afford customer support, and we had to just do it all ourselves. And I asked them this question. If I had given you five million on a twenty-five million price, like you could probably get today if you go to the Valley, Would Lightspeed in this case have been the same as it is today?

A I don't think so. It probably, it probably could be something different and as, as, as successful, which I don't know what it would look, maybe necessarily look like, look like, but those seven years of bootstrapping, like we're, we're in our profitable growth phase where we're now, you know, out of this growth, growth, growth at all costs phase, and we're now into balancing growth and profit. That's like the early, early first seven years where we were profitable. Uh, and we, we ran the company and grew with a great degree of balance. And, and I think that that's, that those are, that's a great part of our DNA. We also had a really good seven years of, of really solidifying our identity. And that, I think that strong sense of identity and, and who we are and what we represented and, and how we did business, um, helped a tremendous amount when we took VC money, when we went public and also when we, uh, did M and A. Because when you bring, when you merge other companies into your company, you have to have a strong sense of identity to allow other companies to be able to flourish, um, as a part of your company and not try to suffocate them out of insecurity, you know? And so that, that I think that strong sense of identity has allowed Lightspeed to do a lot of the, the, the big, the big things it's done.

AI assessment note: “I don't think so. It probably, it probably could be something different”

Q So, but I just find it funny, because people often struggle, and I'm like, fuck, I have so many that I could say for myself. Do you think you found yourself as a leader at some point? I know that sounds really weird and spiritual, and I don't mean that, but like, I think you learn who you are in leadership.

A Yeah. I didn't think of myself as a leader, you know, and that, that two year period I spoke about where it was like four AM in the morning, that was me transitioning from me being that independent software guy, uh, one man show. Just a little bit scared of my team. Like this team, the software was selling really well and this team was growing. I was like on the third floor of this apartment building. I rented the second floor for Lightspeed. Um, and that second floor started to grow, like, There's lots and lots of people starting to show up there, you know, because we were selling, the revenue was coming in, and we were, we needed more folks. Eventually, I had to start talking to these, these people, and I, I was forced to be a leader, and we talked about the dreamer that I was as a kid. I was like an introvert, you know, and I think Lightspeed's pushed me to be able to articulate a vision, to be able to communicate, but it didn't come naturally. And I think that's something that I think a lot of people that, that, um, that are, that are in startups that might be passionate about solving a problem, then they have to figure out, okay, now how do I be a leader? How do I lead these folks? How do I inspire these folks? How do I pivot these folks? How do we, how do I convince the market? How do I talk to media? This is, it's, it's not necessarily something that everybody knows how …

AI assessment note: “Eventually, I had to start talking to these, these people, and I was forced”

Q What's the most contrarian or unorthodox advice that you'd have for founders listening?

A Everybody's so loves their pitch decks, you know, and, uh, I always, I always see a little bit of a frown when I'm, when I suggest to folks that, um, the thing that made a huge difference to me Is that I was forced to write a three year business plan in order to get our early grants. Like I got a 6008 thousand dollar grant, you know, when I was basically on unemployment, when I started light speed, uh, and that three year business plan, I just thought it was so much BS. So I was like, Oh, I just got to do this and mail it in. And, but it, it was a written component and a spreadsheet component. And that, that, uh, business plan, we actually hit that business plan on the nose in year one. Um, no, we, I think we, we, we, we failed a little bit on year one, but year two, we hit it on the mark, and year three, we exceeded it, and it actually changed everything about our pricing, because we actually had to run everything through spreadsheets. It actually solidified and made, helped us decide what we were doing and what we're not doing, and I know it's not fashionable, and I know that people love their 10, 10, 10 slide pitch deck, but that's not a business plan. I think people are a little bit scared by the rigor of what Having to write an essay and then have a three year spreadsheet of what you're going to do. I don't know. I think it's necessary. I don't think we'd be the same compa…

AI assessment note: “the thing that made a huge difference to me Is that I was forced to write a three year business plan”

Q Wow. Okay. And so how, I'm sorry, I'm fascinated. How do you do it? You call them up and say, hey, Dax, um, do you, do you need our help with Lightspeed? Do you go into the stores? What was it?

A When it was our direct sales model, like we're doing a lot of, uh, performance marketing, you know, it's, uh, it's for people that are looking for, for, for a retail point of sales systems or later hospitality point of sales systems, you know, you're, You're generating all those leads and you're qualifying the leads, then your salespeople are closing. And then the close rates, you know, we had really, really strong close rates because we prospected, you know, leads that were very much in our, um, in our, in our wheelhouse. It was a good, they were a good match for the product. Now, today we're going after ICP merchants and, um, we're making a transition with locations where before we were going after everything and a lot of our, everything in, in terms of like every range of GTV. Right? So, 500,000 and above is really where Lightspeed's determined where we can, where our product is the best fit. Uh, but we have tremendous, we have a lot of customers that are sub 500,000 as well.

AI assessment note: “we're doing a lot of, uh, performance marketing, you know, it's”

Q Why did you decide then was the right time? Seven years in is a long period of time. When did you, why did you decide then and what revenue were at when, when you decided to raise? I'm fascinated.

A We were at ten million, um, And, uh, it was actually, you know, the, those folks that I just mentioned Square and, and, and, uh, that, uh, it was a New York POS company called Shopkeep. They were, you know, there was new players coming onto the scene. Um, cause at this point we were, we were competing with legacy black plastic POS systems. It was easy, you know, to compete with them, but then other, other, you know, uh, uh, POS systems that were more forward looking, more cloud-based, uh, Like square, even though it was very simple at the time and like shopkeep, which was an iPad POS, which we had, but ours wasn't cloud-based. They started to come out and even though they were very simple, they had hundreds of millions of dollars being funneled into them. And it started to be, I went from a, from the perspective of like, Hey, I have no finance background. I haven't really looked for investors too. Maybe it would be maybe not a bad idea. And we didn't actually go out looking for VC money. We, um, we did, we were, We were masters of the trade show. We'd done mackerel for many years, and then we switched to doing NRA, which is National Retail Federation that happens in, um, in New York. And in, in 2000, it was 2000, uh, January, January of 2012, a number of VCs come to our booth, uh, looking for the future of retail, because every retail player is there. And they identified Lights…

AI assessment note: “We were at ten million... there was new players coming onto the scene.”

Q What's the most contrarian or unorthodox advice that you'd have for founders listening?

A Everybody's so loves their pitch decks, you know, and, uh, I always, I always see a little bit of a frown when I'm, when I suggest to folks that, um, the thing that made a huge difference to me Is that I was forced to write a three year business plan in order to get our early grants. Like I got a 6008 thousand dollar grant, you know, when I was basically on unemployment, when I started light speed, uh, and that three year business plan, I just thought it was so much BS. So I was like, Oh, I just got to do this and mail it in. And, but it, it was a written component and a spreadsheet component. And that, that, uh, business plan, we actually hit that business plan on the nose in year one. Um, no, we, I think we, we, we, we failed a little bit on year one, but year two, we hit it on the mark, and year three, we exceeded it, and it actually changed everything about our pricing, because we actually had to run everything through spreadsheets. It actually solidified and made, helped us decide what we were doing and what we're not doing, and I know it's not fashionable, and I know that people love their 10, 10, 10 slide pitch deck, but that's not a business plan. I think people are a little bit scared by the rigor of what Having to write an essay and then have a three year spreadsheet of what you're going to do. I don't know. I think it's necessary. I don't think we'd be the same compa…

AI assessment note: “I was forced to write a three year business plan”

Q So if we go back to that first product, did we have product market fit from day one? And I'm just interested when you think back to that, what are some of your biggest lessons from that zero to one discovery on that V one?

A The first two years, um, I coded literally till four in the morning. For that first two years every day. I was fueled on, I don't know if you know Tim Hortons here in Canada, but it's like these French vanilla coffees that are like all caffeine and sugar. They're just like fueled by these things. There's like coding. But what, what was, I think what helped the product market fit happen is when I wasn't coding, I was with those, I was with those early four customers, you know, and they were like, I picked a variety of different customers and I'd sit, you know, with those customers and watch them use the software and then iterate quickly so that If something didn't fit with their workflow or, or, or it didn't consider something that they needed to do with their inventory, there would be another iteration of the software that was outs, you know, within a week or so, they got them closer and closer to a perfect workflow.

AI assessment note: “what helped the product market fit happen is when I wasn't coding, I was with”

Q Can I ask you, when you think about your early go to market and early distribution, what did you not do well? What do you look back on and go, ah, that was a big mistake. And what do you learn from that?

A Well, the reseller strategy was really successful. In those first seven years, it's zero. We spent zero money on, on advertising, right? We, but we spent a lot of money on these reseller conferences twice a year. And we'd have like three, 400 people show up. And actually, When the VCs came and saw that they, they went undercover. They went undercover under false identities with a lot of fun. Uh, during our Dallas, uh, certification camp, our term sheet went from twenty five million to thirty million because they were like, wow, you got a massive community of people around from like Saudi Arabia and like in like Europe and Australia and all over the U S and Canada and like everywhere people are coming to learn how to sell light speed and are generally also Users of Lightspeed. I think we did a good job at first of integrating our direct go-to-market effort because we had internal salespeople, but we always gave priority to the reseller. I think as we got bigger, you know, we had struggles with, okay, when does it become a direct lead? When does it become a reseller lead? Some of the resellers weren't as fast as the other ones. We're like, oh, if we kept that as a direct lead, we could just close that on our own. And then as we went into the cloud and there was less of a need for Uh, reseller to do hardware. We started to lean more and more towards doing everything direct. And th…

AI assessment note: “we cut out a lot of the reseller energy... that might've been a mistake”

Q Wow. Okay. And so how, I'm sorry, I'm fascinated. How do you do it? You call them up and say, hey, Dax, um, do you, do you need our help with Lightspeed? Do you go into the stores? What was it?

A When it was our direct sales model, like we're doing a lot of, uh, performance marketing, you know, it's, uh, it's for people that are looking for, for, for a retail point of sales systems or later hospitality point of sales systems, you know, you're, You're generating all those leads and you're qualifying the leads, then your salespeople are closing. And then the close rates, you know, we had really, really strong close rates because we prospected, you know, leads that were very much in our, um, in our, in our wheelhouse. It was a good, they were a good match for the product. Now, today we're going after ICP merchants and, um, we're making a transition with locations where before we were going after everything and a lot of our, everything in, in terms of like every range of GTV. Right? So, 500,000 and above is really where Lightspeed's determined where we can, where our product is the best fit. Uh, but we have tremendous, we have a lot of customers that are sub 500,000 as well.

AI assessment note: “we're doing a lot of, uh, performance marketing... generating all those leads and you're qualifying”

Q So if we go back to that first product, did we have product market fit from day one? And I'm just interested when you think back to that, what are some of your biggest lessons from that zero to one discovery on that V one?

A The first two years, um, I coded literally till four in the morning. For that first two years every day. I was fueled on, I don't know if you know Tim Hortons here in Canada, but it's like these French vanilla coffees that are like all caffeine and sugar. They're just like fueled by these things. There's like coding. But what, what was, I think what helped the product market fit happen is when I wasn't coding, I was with those, I was with those early four customers, you know, and they were like, I picked a variety of different customers and I'd sit, you know, with those customers and watch them use the software and then iterate quickly so that If something didn't fit with their workflow or, or, or it didn't consider something that they needed to do with their inventory, there would be another iteration of the software that was outs, you know, within a week or so, they got them closer and closer to a perfect workflow.

AI assessment note: “what helped the product market fit happen is when I wasn't coding, I was with those”

Q Final one for you, my friend. What question are you not asked that you should be asked more?

A I think the question, uh, sometimes that once in a while gets asked, and, uh, and I have to, um, I'm happy to give an answer on is like, if you're such an environmentalist, how come you're, Company supports consumerism. You know, it's, um, you're powering, you know, the restaurants and you're powering retail stores. I do believe in local business, uh, being able to make better choices, uh, that are like rooted in the, in their communities, rooted in, in like sustainable, um, options. And so it's going to come more from, from, uh, from the local businesses than it is from the multinationals. And it's, Uh, and I think that it allows people to, um, also make those choices, you know, as consumers. So I, so I think that there's an, there's an alignment there. We have to transform the way that we, the way that we consume, um, If we want to make progress on the environment, like we're not going to stop eating. We're not going to stop buying things, but I think rediscovering retail and hospitality, like it's better to go to a restaurant, uh, with their reusable plates, uh, investing in the, in the, in the, in the people that work in those places. There's less, there's less, uh, waste. You know, if you think about retail stores as like a local warehouse, they don't, they're not sending boxes to your house. You're going to a place where it's already there and you, you make a selection. I…

AI assessment note: “if you're such an environmentalist, how come you're, Company supports consumerism.”

Q Did you have entrepreneurial pursuits when you were young?

A I did, yeah. My dad brought home a Mac, you know, when I was eight or nine. You know, he, the Mac had just come out. He was a graphic designer. Actually, he was a welder, and, and, ah, they discovered that back in Africa, he was a journalist, and that he was a communications guy, and so they gave him this opportunity, and I went, I nerded out. You know, you're into vertical SaaS. I, I nerded out on UI design and, um, a tool called HyperCard on the early Mac, and that's how I became a programmer. I mean, by 12, um, I had my own Mac, and by 13, I was working for a Mac developer. Uh, that was, that was building early networking software on the Mac.

AI assessment note: “I did, yeah. My dad brought home a Mac”

Q the same, we have LPs, and it's like, tell me about this company in your portfolio, and you're like, I'd love to talk to you about Lightspeed. And then they're like, okay, that's not what we asked you. Um, here, tell me, what concerns you most in the world today? You mentioned, you know, Love of nature and conservatism. What do you love? What are you most concerned about today?

A The environmental trends concern me. That's why it's a, it's a big part of, part of w where I want to apply my startup DNA. Uh, I believe in the startup model. And so I've applied that to conservation and, and I believe that Lightspeed actually helps with sustainability too, because the local businesses that are supported are like the ones that can actually make more sustainable decisions or more community oriented decisions. But yeah, the environmental trends are, Terrifying. But I also, like, I mean, I already told you, um, that I believe in the power of individuals to get results, and I do believe in nature, because nature's super resilient. Like, in, in the projects that we've sponsored for conservation with Age of Union, it's, I've seen nature come back from destruction. And so, you know, whatever we throw at it, nature can, is, is, uh, create really, uh, really a miraculous thing. So, Yeah, it's worrying. It's worrying that the climate's changing really quickly, but I think nature's a solution that's pretty powerful. Like, I, I also think that in society, we're disconnected from two things. Disconnected from nature or disconnected from spirituality, and I think that's why we're unanchored. Uh, and that's why some of my projects outside of Lightspeed really try to look for how we can reconnect with those things in, in ways that, um, that, that people find Um, unexpected or…

AI assessment note: “The environmental trends concern me. That's why it's a, it's a big part”

Q Now, I always think we're always kind of shaped by something in our childhood that maybe wasn't actually that easy. You know, for me, it was actually my mother having MS and looking after her. When you think back to your childhood, was that something that Shaped you or really impacted how you think and who you are today that stands out?

A I had a really beautiful childhood, but I think the context of where my parents had just immigrated from, ah, the, you know, there was a dictator in Uganda, they grew up in Uganda, and my, my family family's from, ah, originally from, from India, from the Portuguese colony called Goa, but they all moved to Uganda for jobs in the British civil service, and then they were expelled, expelled by a dictator in 72. And, uh, you know, my, my mom was 18. My dad was like 20 to 23. And so in that context, I was born, my sister was born in this new country where they were just super young and, and, and had to carve out a unexpectedly carve out a whole new life. And so the fact that we had like these incredible childhoods that, that like we spent a lot of time in nature doing these low cost things like camping, which is why I'm such a big, big proponent of the environment today. Um, It's, it came from a bit of a chaotic background, and I sort of had the immigrant experience, but I'm, you know, born in Canada, so it's, um, yeah, I think it shaped me. You know, I was a little bit of a dreamer, a little bit of a person that would bike around in circles in their front yard, and just dream up fantasy, kind of like cartoons, and sort of, you know, I was just sort of like a, uh, definitely an introvert.

AI assessment note: “camping, which is why I'm such a big, big proponent of the environment today.”

Q Did you have entrepreneurial pursuits when you were young?

A I did, yeah. My dad brought home a Mac, you know, when I was eight or nine. You know, he, the Mac had just come out. He was a graphic designer. Actually, he was a welder, and, and, ah, they discovered that back in Africa, he was a journalist, and that he was a communications guy, and so they gave him this opportunity, and I went, I nerded out. You know, you're into vertical SaaS. I, I nerded out on UI design and, um, a tool called HyperCard on the early Mac, and that's how I became a programmer. I mean, by 12, um, I had my own Mac, and by 13, I was working for a Mac developer. Uh, that was, that was building early networking software on the Mac.

AI assessment note: “I did, yeah. My dad brought home a Mac, you know”

Q Can I be honest, you may not be able or willing to ask it, Blake. You come back because something's not right. You don't change things that are working perfectly well. What was not working perfectly well?

A We all want to see, um, Investor confidence return, uh, in the stock. I mean, that's not been a good story. Uh, and I think that the story is, the story is the profitable growth, uh, adult version of Lightspeed, right? That's got all of these things in balance. Uh, and I think that I felt, JP felt, the board felt that the founder, it's a good, it's a good moment for the founder to be able to tell that story and lead the team through the transitions that are necessary. And we had to do some, in the five months I've been back, we've had to do some tough things. We had, we've had to do a reduction in force. Um, we've had to, you know, get into the capital allocation strategy. We've had to, um, you know, had to make some big clear statements, uh, that, that, that, uh, Calm down nerves about no more, no M&A, no large M&A, and, and show great growth numbers, show, show, like, a great forecast of a balance of profitability and growth. Like, so there's been lots of, lots of, uh, not resets, but clear definitions of what it's going to look like for investors, and now I think that they, they want to see that consistency.

AI assessment note: “Investor confidence return, uh, in the stock. I mean, that's not been a good story.”

Q the same, we have LPs, and it's like, tell me about this company in your portfolio, and you're like, I'd love to talk to you about Lightspeed. And then they're like, okay, that's not what we asked you. Um, here, tell me, what concerns you most in the world today? You mentioned, you know, Love of nature and conservatism. What do you love? What are you most concerned about today?

A The environmental trends concern me. That's why it's a, it's a big part of, part of w where I want to apply my startup DNA. Uh, I believe in the startup model. And so I've applied that to conservation and, and I believe that Lightspeed actually helps with sustainability too, because the local businesses that are supported are like the ones that can actually make more sustainable decisions or more community oriented decisions. But yeah, the environmental trends are, Terrifying. But I also, like, I mean, I already told you, um, that I believe in the power of individuals to get results, and I do believe in nature, because nature's super resilient. Like, in, in the projects that we've sponsored for conservation with Age of Union, it's, I've seen nature come back from destruction. And so, you know, whatever we throw at it, nature can, is, is, uh, create really, uh, really a miraculous thing. So, Yeah, it's worrying. It's worrying that the climate's changing really quickly, but I think nature's a solution that's pretty powerful. Like, I, I also think that in society, we're disconnected from two things. Disconnected from nature or disconnected from spirituality, and I think that's why we're unanchored. Uh, and that's why some of my projects outside of Lightspeed really try to look for how we can reconnect with those things in, in ways that, um, that, that people find Um, unexpected or…

AI assessment note: “The environmental trends concern me. That's why it's a, it's a big part”

Q Can I be honest, you may not be able or willing to ask it, Blake. You come back because something's not right. You don't change things that are working perfectly well. What was not working perfectly well?

A We all want to see, um, Investor confidence return, uh, in the stock. I mean, that's not been a good story. Uh, and I think that the story is, the story is the profitable growth, uh, adult version of Lightspeed, right? That's got all of these things in balance. Uh, and I think that I felt, JP felt, the board felt that the founder, it's a good, it's a good moment for the founder to be able to tell that story and lead the team through the transitions that are necessary. And we had to do some, in the five months I've been back, we've had to do some tough things. We had, we've had to do a reduction in force. Um, we've had to, you know, get into the capital allocation strategy. We've had to, um, you know, had to make some big clear statements, uh, that, that, that, uh, Calm down nerves about no more, no M&A, no large M&A, and, and show great growth numbers, show, show, like, a great forecast of a balance of profitability and growth. Like, so there's been lots of, lots of, uh, not resets, but clear definitions of what it's going to look like for investors, and now I think that they, they want to see that consistency.

AI assessment note: “Investor confidence return, uh, in the stock. I mean, that's not been a good story.”

Q How did you think about building what they needed and not what they wanted? Cause sometimes what they want isn't necessarily right.

A A hundred percent. Right. And so that's where you've got to be. And I think that's like a little bit of where the tech support background comes in of like, okay, the, this user wants to accomplish this. And they think they want to do it this way, but from your observations of what they, of what their operations look like, and that's why you have to kind of in our, in my case, I want it to be physically there with the customer. It's probably not possible for every type of scenario, but I wanted to observe what it looked like, you know, and I wanted to see what they were trying to pull off so that with what I wanted to create as a user experience, maybe we're going to leapfrog their expectations of, of what we want to do. And so there was like, nobody asked for, uh, the mobile checkout. No, we, we didn't raise money for the first seven years.

AI assessment note: “I wanted to observe what it looked like... see what they were trying to pull off”

Q Talk to me about that, because, you know, you're chairman, you can be chilling on a beach, or, you know, doing whatever you want to do, you know, you obviously weren't chilling on a beach, but you can do whatever you want to do in a different capacity. Why did you decide to come back, and why was then the right time?

A What's great about being the executive chair is, it's great for a founder, because you can be on the email, you can be on the slack, you can be in the, get the pulse of the business, but you really aren't in the day-to-day operations. You know, you can kind of see it happening, uh, and unfolding online, um, But being in the chair is very different, you know, and I think that we are in a new phase and we've had, we've pulled off some incredible things, the acquisitions, getting to two flagships, uh, making the payments thing. A lot, a lot of the, the market was skeptical on the payment that we'd be able to execute on the payments thing. All that's been done. But now I think we're in this grown up phase. Like we are no longer a teenager next year. We're turning 20, right? Like I want us to be a great adult. You know, we're we've, we've, uh, We know what the formula is, you know, and I think that, uh, that's, it's a good time for a founder to, um, lead people through some, maybe some structural changes, you know, like.

AI assessment note: “it's a good time for a founder to, um, lead people through”

Q I need you in payments. And you're going, huh, payments. We should look more, and suddenly you're pulled into doing payments in year two. I'm just saying that. You didn't, you didn't know that you'd ever do payments. You thought you were just rational software, but you would not do payments because it didn't go to your model. But payments may have been perfect. Do you see what I mean?

A Yet, Harry, I would say that, um, if I look at that original Lightspeed business plan, Or Exilva systems, as we recall back then, ah, with the product of Lightspeed. That is really the same customer, and, and, ah, it's, it's so much is, almost 20 years later, so much is at the, it's the core of, it's still relevant in terms of who we define ourselves as, and who we define our customer as. So, yeah, we've expanded to payments, we've expanded to another vertical beyond retail, but it's crystallization of what we're offering, and what we're doing on the value, and And then, and how we're going to market, even though that's evolved, um, it was a, it was a moment of clarity.

AI assessment note: “So, yeah, we've expanded to payments, we've expanded to another vertical”

Q Okay, but my point being, like, that was kind of slow trajectory, and so it's like, do you think SaaS investors today have broken models that will miss great companies like Lightspeed, given the new demands of venture?

A I know that when I've mentored companies that are building these, these SaaS solutions, um, they're, you know, They're having to, in order to have attractive metrics that are going to be interesting to VCs, they're shortcutting a lot of the, a lot of the product development and like the bare, the basics of building a business like we did. Obviously, there's less room to, to, to, to test and battle test, uh, and get to something really phenomenal, potentially. I, I'm sure there's, there's outstanding entrepreneurs to get there, uh, despite all those constraints of having to do it quickly and prove and prove, you know, prove, um, Prove what they've got is worth a big term sheet. The slow burn, you know, like, I think that's, there's quality that happens in, in, in, in that process, and, you know, let it cook, right?

AI assessment note: “in order to have attractive metrics that are going to be interesting to VCs”

Q Talk to me about that, because, you know, you're chairman, you can be chilling on a beach, or, you know, doing whatever you want to do, you know, you obviously weren't chilling on a beach, but you can do whatever you want to do in a different capacity. Why did you decide to come back, and why was then the right time?

A What's great about being the executive chair is, it's great for a founder, because you can be on the email, you can be on the slack, you can be in the, get the pulse of the business, but you really aren't in the day-to-day operations. You know, you can kind of see it happening, uh, and unfolding online, um, But being in the chair is very different, you know, and I think that we are in a new phase and we've had, we've pulled off some incredible things, the acquisitions, getting to two flagships, uh, making the payments thing. A lot, a lot of the, the market was skeptical on the payment that we'd be able to execute on the payments thing. All that's been done. But now I think we're in this grown up phase. Like we are no longer a teenager next year. We're turning 20, right? Like I want us to be a great adult. You know, we're we've, we've, uh, We know what the formula is, you know, and I think that, uh, that's, it's a good time for a founder to, um, lead people through some, maybe some structural changes, you know, like.

AI assessment note: “it's a good time for a founder to, um, lead people through some, maybe some structural changes”