The Exchanges

Q Who's the best board member you've sat on a board with, and what, what do they do to be so special?

A One of the folks that we work very closely with here at Lightspeed is a gentleman named John Thompson. John Thompson was the CEO of Symantec for, for about 10 years. He took that company from six hundred million to six It's a billion dollars in revenue. He's now the chairman of Microsoft, and in between, he ran a company called Virtual Instruments, which we actually invested in, and John is a veteran of the enterprise space. He's incredibly insightful. He understands the go-to-market motion. He understands what it means to do company design, and he truly understands what great people, great management look like, and he plays a very, very active role in the companies that he works with, whether it's helping hire people, whether it's helping open doors to the right customers, Or whether it's just mentoring CEOs and helping them think through the challenges that they inevitably face on a daily basis.

AI assessment note: “a gentleman named John Thompson. John Thompson was the CEO of Symantec”

Q Who's the best board member you've sat on a board with, and what, what do they do to be so special?

A One of the folks that we work very closely with here at Lightspeed is a gentleman named John Thompson. John Thompson was the CEO of Symantec for, for about 10 years. He took that company from six hundred million to six It's a billion dollars in revenue. He's now the chairman of Microsoft, and in between, he ran a company called Virtual Instruments, which we actually invested in, and John is a veteran of the enterprise space. He's incredibly insightful. He understands the go-to-market motion. He understands what it means to do company design, and he truly understands what great people, great management look like, and he plays a very, very active role in the companies that he works with, whether it's helping hire people, whether it's helping open doors to the right customers, Or whether it's just mentoring CEOs and helping them think through the challenges that they inevitably face on a daily basis.

AI assessment note: “a gentleman named John Thompson. John Thompson was the CEO of Symantec”

Q When you think about kind of go to market over the last few years and go to market execution, maybe more. When you think about that, who do you think is maybe innovated or kind of executed specifically well in your mind? And what do you think that they did so well?

A There's a number of great companies. We talked a little bit about Slunk. It really did innovate in the early days around matching their product to go after the IT manager and making that IT manager a hero, but then evolved their go to market motion to go capture more dollars. At a higher level in the organization. So they really designed the hybrid model of rapid go-to-market motion coupled with an enterprise go-to-market motion. I think Palo Alto Networks over the last five years has just demonstrated an ability to execute from a direct sales motion as well as from a channel motion to capture the market share and mind share of security professionals about what a next generation platform looks like. In our portfolio, Rubrik, which is one of the fastest growing enterprise companies, has really figured out how How to go to market very, very rapidly with an enterprise sales motion, which is both land and expand, and is upending a number of legacy vendors in the data management and data backup space.

AI assessment note: “Palo Alto Networks over the last five years has just demonstrated an ability to execute”

Q Tell me, final one, what's the most recent publicly announced investment, and why did you get so excited?

A Oh, there's a couple. So, we most recently announced a very big round in trip actions. This is a company in the corporate travel space. They're building, and they have built, the fastest growing online corporate travel management company ever. They now manage over a billion dollars in corporate travel. They're growing 15 to 20% month over month. This is a company I've been privileged and humbled to have worked with from the very, very beginning days to the Steed, and then the Series A, and then through the Series B, and so, although it's something we publicly announced recently, a recent round, it's, it's an incredible company that has a long, long way to go. Another company I'm super excited about is called AppZen. This is a company we announced late last fall. It's using AI and ML in a very practical They go after today expenses and invoices and look at companies expense reports and find fraud. This is something that almost every company in the world has. There's obviously salespeople that go out and do expense things they shouldn't be expensing. There's rank and file that make mistakes on a daily basis on their expense reports. These guys automatically using deep learning, machine learning, plus a workflow and orchestration engine can find those mistakes or find that outright fraud. And delivered not only compliance, but also better usage of travel and expense budgets inside…

AI assessment note: “we most recently announced a very big round in trip actions.”

Q I mean, so many things for me to unpack there as a venture nerd. So, I wanted to start on the valuation element. I had another guest on the show recently, Matt Harris at Bain, and he said that Series A valuations don't matter anymore. Can I ask, how do you feel about that, and would you maybe agree with him?

A Valuation always matters, in my opinion, but, you know, you can be less price sensitive on premium companies with premium markets, and what I mean by that is, Teams that are exceptional, that have a very, very strong point of view, clarity of thought, and ability to execute, and potentially have already demonstrated ability to execute, will get premium valuations. Now, Series A valuation doesn't matter, is, is a very general point of view. Can you do a Series A at a billion dollars? Perhaps, but then you'd have to underwrite to at least a 10 to twenty billion dollar outcome. I'd say what we're seeing in Series A is, is absolutely prices have drifted up. When I entered the venture market, Series A's were done anywhere between five and ten million dollar pre-money valuation. Now you're seeing them get into 20 to 50 to 60. But if the market size plus the team can justify an outsized return, then it's potentially worth the risk. And so it does matter, but you can make exceptions for the great, great companies.

AI assessment note: “Valuation always matters, in my opinion, but, you know, you can be less price sensitive”

Q past is, you know what, the team is so good, they'll figure it out along the way, given that they have enough runway to make that happen, but they'll Figure it out along the way, and they'll find the right insertion point, the right adjacent market. Is that a fair argument or gene? That's potentially lazy thinking, and actually markets should be central to when you are making the investment.

A There are many, many different types of venture investors, and some investors will underwrite that. I prefer to have a very strong point of view around market, and markets can be new markets, but you've got to believe that those markets will be very, very large and outsized, or markets can be existing markets where there's shifting in dollars from one pocket to another, from legacy to new. If you're trying to evangelize a market and then underwrite that market size, that can become very, very challenging. You're right. Some great teams will figure it out. They'll pivot once, twice, three times, and there are great stories of those companies that have really pivoted into great markets. The most interesting one being Slack, which pivoted from a gaming company to almost an enterprise messaging company. So great teams can figure it out, but if you're going to pay an outsized valuation behind a team, then at least in your underwriting model, that needs to be part of your mental model.

AI assessment note: “I prefer to have a very strong point of view around market”

Q the upending the legacy companies that we have today, because we've seen a lot of the Qualtrics, the Duos, the AppDynamics, the MuleSofts, which incredible companies and standalone companies could be in their own right, absolutely, but did that end up being acquired by existing legacy incumbents? How do you think about consolidation in the enterprise market moving forward from today over the next kind of three to five years?

A I think the legacy vendors, they're smart, right? They're looking at the, this changing landscape. They're looking at the new technologies that the companies are adopting. They're looking at the massive trends that I talked about cloud and data and AI plus ML. And they're saying we need to, to stay relevant. We need to keep being relevant to our customers. So they will make offers to premium companies. And then it really depends on the leadership teams of those companies that are upending the status quo and their confidence in their product and their determination to To continue to stay private in order to create outsized legacy companies. You're already seeing a little bit of the shift in status quo. You've got companies like Palo Alto Networks, which is north of twenty billion dollars. That's become a platform company that has now demonstrated an ability to innovate, continue to build their, on their platform, and do some strategic acquisitions. So they're starting to look like one of the incumbents in the security space. If you look at a company like Splunk, which is a dominant player in the data space, That was a venture-backed company. That was a company that went public that a lot of people had written off due to questions around market size, and the executive team there is executed almost flawlessly to a twenty billion dollar valuation, and now they're doing their own pl…

AI assessment note: “we're already seeing the upending of the legacy vendors with some new challengers”

Q I mean, so many things for me to unpack there as a venture nerd. So, I wanted to start on the valuation element. I had another guest on the show recently, Matt Harris at Bain, and he said that Series A valuations don't matter anymore. Can I ask, how do you feel about that, and would you maybe agree with him?

A Valuation always matters, in my opinion, but, you know, you can be less price sensitive on premium companies with premium markets, and what I mean by that is, Teams that are exceptional, that have a very, very strong point of view, clarity of thought, and ability to execute, and potentially have already demonstrated ability to execute, will get premium valuations. Now, Series A valuation doesn't matter, is, is a very general point of view. Can you do a Series A at a billion dollars? Perhaps, but then you'd have to underwrite to at least a 10 to twenty billion dollar outcome. I'd say what we're seeing in Series A is, is absolutely prices have drifted up. When I entered the venture market, Series A's were done anywhere between five and ten million dollar pre-money valuation. Now you're seeing them get into 20 to 50 to 60. But if the market size plus the team can justify an outsized return, then it's potentially worth the risk. And so it does matter, but you can make exceptions for the great, great companies.

AI assessment note: “Valuation always matters, in my opinion, but, you know, you can be less price sensitive”

Q the upending the legacy companies that we have today, because we've seen a lot of the Qualtrics, the Duos, the AppDynamics, the MuleSofts, which incredible companies and standalone companies could be in their own right, absolutely, but did that end up being acquired by existing legacy incumbents? How do you think about consolidation in the enterprise market moving forward from today over the next kind of three to five years?

A I think the legacy vendors, they're smart, right? They're looking at the, this changing landscape. They're looking at the new technologies that the companies are adopting. They're looking at the massive trends that I talked about cloud and data and AI plus ML. And they're saying we need to, to stay relevant. We need to keep being relevant to our customers. So they will make offers to premium companies. And then it really depends on the leadership teams of those companies that are upending the status quo and their confidence in their product and their determination to To continue to stay private in order to create outsized legacy companies. You're already seeing a little bit of the shift in status quo. You've got companies like Palo Alto Networks, which is north of twenty billion dollars. That's become a platform company that has now demonstrated an ability to innovate, continue to build their, on their platform, and do some strategic acquisitions. So they're starting to look like one of the incumbents in the security space. If you look at a company like Splunk, which is a dominant player in the data space, That was a venture-backed company. That was a company that went public that a lot of people had written off due to questions around market size, and the executive team there is executed almost flawlessly to a twenty billion dollar valuation, and now they're doing their own pl…

AI assessment note: “I would argue that we're already seeing the upending of the legacy vendors”

Q Okay, so I should probably read more than I admit to. What's the favorite book and why?

A I should probably read more than I admit to also. I've got two, I don't have a necessarily a favorite book, but there are two books That I've recently read. One I read a dozen years ago. The one I read, the other one I read more recently. The one I read a dozen years ago really changed my outlook on how I go about my life, and it's called Stumbling on Happiness, and it really exposes how your brain can fill in blanks, either in memory or in the way that you forward project, and how those blanks can actually affect outcomes and your reaction to those outcomes, and that affects happiness, that affects investment decisions, that affects How You Act in Your Daily Life. It's actually a really insightful book, and I'd encourage anybody who's interested in understanding their own psychology to read that book, because it'll, it'll shine a better light on how our brain can play tricks on us. And then the other book I read much more recently is a book called How Not to Die. The name of the book hits you in the face, but if you're interested in wellness and longevity, then I'd strongly recommend you read this book, because it shines a light on some of the things that we as a society have done from a dietary perspective. And how that diet is affecting, not deterministically, but potentially our outcomes as, as human beings, and so I read that book. I don't follow it to the T, but it's cert…

AI assessment note: “I don't have a necessarily a favorite book, but there are two books”

Q When you think about kind of go to market over the last few years and go to market execution, maybe more. When you think about that, who do you think is maybe innovated or kind of executed specifically well in your mind? And what do you think that they did so well?

A There's a number of great companies. We talked a little bit about Slunk. It really did innovate in the early days around matching their product to go after the IT manager and making that IT manager a hero, but then evolved their go to market motion to go capture more dollars. At a higher level in the organization. So they really designed the hybrid model of rapid go-to-market motion coupled with an enterprise go-to-market motion. I think Palo Alto Networks over the last five years has just demonstrated an ability to execute from a direct sales motion as well as from a channel motion to capture the market share and mind share of security professionals about what a next generation platform looks like. In our portfolio, Rubrik, which is one of the fastest growing enterprise companies, has really figured out how How to go to market very, very rapidly with an enterprise sales motion, which is both land and expand, and is upending a number of legacy vendors in the data management and data backup space.

AI assessment note: “There's a number of great companies. We talked a little bit about Slunk.”

Q when you're self-reflective on how you think about investing, Have you seen your price sensitivity change over time with the lessons and maybe learnings from saying no to companies because of price and then going on to be great successes or maybe having paid up for companies and being thrilled that you did pay up. Have there been any changes in how you view price sensitivity yourself as an investor?

A Absolutely. You know, I, I think more and more about what the outcome can be and about the team's ability to execute. And so with those two core factors, what is the prize and If the prize can justify the entering price, which then helps you underwrite the risk, then it's worth it. Because, you know, as venture capitalists, we take team risk, we take product risk, we take market risk. And I think market risk is the most dangerous risk to underwrite. Even if with the greatest teams, teams can't fight market. Market always wins. And so if the market doesn't justify a potentially outsized return, an outlier return, then it's potentially not worth investing or taking on the risk. However, If it's a team that has shown ability to execute, that has clarity of vision, that has an incredible product or product vision, and can execute in a very, very large market, it's not worth trying to optimize on the edges for valuation.

AI assessment note: “it's not worth trying to optimize on the edges for valuation.”

Q and he said, you know, SMB, it's just such low ACVs that you just need such velocity and traction to make it meaningful. Enterprise, oh, the sales cycles are so long. It's just so cumbersome. And then mid-market, well, we all know no man's land in SaaS pricing. I guess, how would you respond to this, and how do you often think and advise startups on the right insertion point?

A Well, the first advice I give to founders is really think about who your economic buyer is for your product. It's really hard to take an enterprise product and take it down market into an SMB if an SMB is never going to buy that product, and vice versa. If you've got an SMB product and it doesn't have the security, compliance, auditability, scalability, performance that is required in the enterprise, and it doesn't make sense to try to sell an SMB product Into the enterprise, and so this gets back to company design. Figure out who your economic buyer is for your product, for your innovation, and then execute on the best motion to sell into that economic buyer, whether it's an enterprise, whether it's a mid-market, or whether it's an SMB. What we see for a lot of our enterprise customers is they start with a land model, and that land model targets both mid-market and enterprise customers. Really, the reason they do that is mid-market customers move faster, but of course, you You capture less value, but you can get some velocity and you can get some market signals about product market fit in the mid market. And meanwhile, you're executing on a longer sales cycle with enterprises, but perhaps you design your product in a way that it's not a million dollar initial bite size, but maybe it's a 75,000 dollar to a 100,000 dollar bite size that can be expanded into over time, a million …

AI assessment note: “Figure out who your economic buyer is for your product, for your innovation”

Q to ask, you said there about Splunk being kind of potentially questioned in the earlier days for the smaller market. I always worry, not in terms of market size, but I'm always very cautious in terms of market timing. How do you think about market timing? Is that, is that at the forefront of your mind, or is that something that we as venture investors have to get used to?

A Market timing is, it's difficult, but it's an opportunity. And so, remember what I said, you're either investing in an existing market or an expanding, a new and expanding market. And the new and expanding market really does depend on market timing. It depends on when, call it, a trend starts to tip and become more mainstream. And those companies that are very well positioned for the market tipping Can become outsized winners. And so it is a delicate balancing act. And the way I think about it is market timing works in markets where there's dollars shifting from call it one technology stacker or legacy architecture to a new type of architecture. The most recent being cloud. If you can make an argument that cloud is up ending both from a business model perspective, from a consumption perspective, as well as a technology perspective is up ending on premise. Then you make the argument that dollars that were in on-premise are tipping towards cloud. That wasn't entirely clear when that market time was happening, but those companies that were very, very smart, not only about building a new type of product for this new world, but also spending a lot of time with customers to understand those customers' propensity to shift, were the winners.

AI assessment note: “the way I think about it is market timing works in markets where there's dollars shifting”

Q I was chatting to a GP the other day at a Series A fund. And he said that a couple of his companies have raised at a hundred X ARR, both in the enterprise space. And I wanted to start with that being, and I hope this isn't negative or cynical, but do you think enterprise investing is potentially past its peak today, given the hype and excitement around it?

A I don't think so. I think that the word is out. It's become very, very sexy. I think that a number of other great investors are realizing that you can actually build companies worth 10 to twenty billion dollars in the enterprise space. And so, I think what's happened is over the last decade, you've seen people's point of view around the enterprise stack really, really change, and actually what's driving this is, I think we're in a magical time where the entire enterprise stack, from storage, cloud, networking, through the app tier, CRM, marketing service, etc., I think all of that's up for grabs, driven by a number of really interesting new technologies fueled by cloud, plus data, plus There's a trillion dollars of market cap off for grabs, and so the word is out. As a result of that, great teams who are building very, very innovative product that can upend the legacy vendors are getting premium valuations, and play it forward. You see companies that have executed on their plans, companies like Zoom, which is in the 20 to twenty-five billion dollar market cap, companies like Slack, companies like Palo Alto Networks, Splunk. All of these companies are twenty billion or more, which has been relatively rare in Opportunities in realizing that if these companies execute, the prize is very large.

AI assessment note: “I don't think so. I think that the word is out.”

Q to move a little bit, though, further deeper into the enter Enterprise space itself, because when we chatted before, you said to me, there's a well-trodden path to five to ten billion dollars in enterprise market caps, but this takes special attention to company design, you said. My question to you here is, what did you mean by the attention to company design? How does that look in your mind?

A Yeah, company design in my mind is an art and a science, and it transcends just product design, and I think what I've seen over my career is a lot of great technologists or Product folks really tend towards my product is the best product, and as a result of that, it should be bought. What I've learned over time is the best enterprise companies, the winners, are those that marry amazing product design, which is a combination of technology architecture plus product, which translates into UI and UX, and marry those with a great go-to-market design. So how do you design the best go-to-market motion for the product that you've built, and then how do you architect the team for both the product and And the go-to-market motion. So it really is designing your company to take advantage of your innovation around both the technology and product and designing the go-to-market motion in a way that is true to your product and finding the people, the execs, as well as the rank and file engineers, salespeople, customer success, customer support, sales engineers, who can actually execute on your, the go-to-market motion that you've designed for your product. Company design, it's thinking holistically about your company, about your people, about your product, and about your go-to-market motion.

AI assessment note: “thinking holistically about your company, about your people, about your product”

Q Well, please listen, if you solve that, let me know. I will pay you huge amounts of money. Tell me, what do you know now that you wish you'd known at the start of your career in venture?

A That's an interesting one because I've been passionate about joining the venture capital industry for many, many years. I was driven to join this industry. Once I got in, the thing that surprised me the most was really the long cycles of venture capital and the long, long feedback cycles. And the challenge is to, for someone who comes from industry, who's operational, the feedback in an operational world is very, very quick. In an operational world, you need to go and build a product. You need to go and sell X amount of dollars of product in a quarter. So the feedback loop is extremely fast. In the venture capital world, the feedback loop is slow. You can prove that you can win deals, but you, it takes time to really learn whether you're good at winning the right deals. In many cases, it can take five, maybe 10 years to know if your judgment is right, to know if your intuition is right, to know if your gut is right. So it's one of those industries where You have to be long-term focused. You need to be very, very patient. You need to be iterative yourself at understanding really on a daily basis, questioning some of your, your intuitions, your judgments, your decisions, and learning from those, but keeping in mind that the feedback cycle is a very, very long feedback cycle.

AI assessment note: “the thing that surprised me the most was really the long cycles of venture capital”

Q I was chatting to a GP the other day at a Series A fund. And he said that a couple of his companies have raised at a hundred X ARR, both in the enterprise space. And I wanted to start with that being, and I hope this isn't negative or cynical, but do you think enterprise investing is potentially past its peak today, given the hype and excitement around it?

A I don't think so. I think that the word is out. It's become very, very sexy. I think that a number of other great investors are realizing that you can actually build companies worth 10 to twenty billion dollars in the enterprise space. And so, I think what's happened is over the last decade, you've seen people's point of view around the enterprise stack really, really change, and actually what's driving this is, I think we're in a magical time where the entire enterprise stack, from storage, cloud, networking, through the app tier, CRM, marketing service, etc., I think all of that's up for grabs, driven by a number of really interesting new technologies fueled by cloud, plus data, plus There's a trillion dollars of market cap off for grabs, and so the word is out. As a result of that, great teams who are building very, very innovative product that can upend the legacy vendors are getting premium valuations, and play it forward. You see companies that have executed on their plans, companies like Zoom, which is in the 20 to twenty-five billion dollar market cap, companies like Slack, companies like Palo Alto Networks, Splunk. All of these companies are twenty billion or more, which has been relatively rare in Opportunities in realizing that if these companies execute, the prize is very large.

AI assessment note: “I don't think so. I think that the word is out.”

Q when you're self-reflective on how you think about investing, Have you seen your price sensitivity change over time with the lessons and maybe learnings from saying no to companies because of price and then going on to be great successes or maybe having paid up for companies and being thrilled that you did pay up. Have there been any changes in how you view price sensitivity yourself as an investor?

A Absolutely. You know, I, I think more and more about what the outcome can be and about the team's ability to execute. And so with those two core factors, what is the prize and If the prize can justify the entering price, which then helps you underwrite the risk, then it's worth it. Because, you know, as venture capitalists, we take team risk, we take product risk, we take market risk. And I think market risk is the most dangerous risk to underwrite. Even if with the greatest teams, teams can't fight market. Market always wins. And so if the market doesn't justify a potentially outsized return, an outlier return, then it's potentially not worth investing or taking on the risk. However, If it's a team that has shown ability to execute, that has clarity of vision, that has an incredible product or product vision, and can execute in a very, very large market, it's not worth trying to optimize on the edges for valuation.

AI assessment note: “it's not worth trying to optimize on the edges for valuation.”

Q to ask, you said there about Splunk being kind of potentially questioned in the earlier days for the smaller market. I always worry, not in terms of market size, but I'm always very cautious in terms of market timing. How do you think about market timing? Is that, is that at the forefront of your mind, or is that something that we as venture investors have to get used to?

A Market timing is, it's difficult, but it's an opportunity. And so, remember what I said, you're either investing in an existing market or an expanding, a new and expanding market. And the new and expanding market really does depend on market timing. It depends on when, call it, a trend starts to tip and become more mainstream. And those companies that are very well positioned for the market tipping Can become outsized winners. And so it is a delicate balancing act. And the way I think about it is market timing works in markets where there's dollars shifting from call it one technology stacker or legacy architecture to a new type of architecture. The most recent being cloud. If you can make an argument that cloud is up ending both from a business model perspective, from a consumption perspective, as well as a technology perspective is up ending on premise. Then you make the argument that dollars that were in on-premise are tipping towards cloud. That wasn't entirely clear when that market time was happening, but those companies that were very, very smart, not only about building a new type of product for this new world, but also spending a lot of time with customers to understand those customers' propensity to shift, were the winners.

AI assessment note: “And the way I think about it is market timing works in markets where”

Q Well, please listen, if you solve that, let me know. I will pay you huge amounts of money. Tell me, what do you know now that you wish you'd known at the start of your career in venture?

A That's an interesting one because I've been passionate about joining the venture capital industry for many, many years. I was driven to join this industry. Once I got in, the thing that surprised me the most was really the long cycles of venture capital and the long, long feedback cycles. And the challenge is to, for someone who comes from industry, who's operational, the feedback in an operational world is very, very quick. In an operational world, you need to go and build a product. You need to go and sell X amount of dollars of product in a quarter. So the feedback loop is extremely fast. In the venture capital world, the feedback loop is slow. You can prove that you can win deals, but you, it takes time to really learn whether you're good at winning the right deals. In many cases, it can take five, maybe 10 years to know if your judgment is right, to know if your intuition is right, to know if your gut is right. So it's one of those industries where You have to be long-term focused. You need to be very, very patient. You need to be iterative yourself at understanding really on a daily basis, questioning some of your, your intuitions, your judgments, your decisions, and learning from those, but keeping in mind that the feedback cycle is a very, very long feedback cycle.

AI assessment note: “the thing that surprised me the most was really the long cycles of venture capital”

Q Well, that is very kind, but I would love to kick off today with a little bit about you and the best question of all, which is how did you make your way into the wonderful world of venture and come to be partner at one of the world's leading firms today in the form of Lightspeed?

A Well, it's a lot of luck. It's a little bit of zigzagging, and it's a little bit of making my own luck. So if you hear an accent, Harry, it's because I'm, um, I'm Canadian. So I grew up in, in Montreal, Canada. I studied computer engineering in the nineties, and in the mid nineties, I started to hear about this place called Silicon Valley. Back then, it wasn't necessarily the standard path for people from the University of Waterloo or other places in Canada to make their way out to California. California was viewed as a place of filled with people who eat kale and do a lot of yoga, but not necessarily a Technology Mecca, but you know, what was happening It was magical, and I decided I really wanted to go see what was happening, and so I made my way out here. My first job was literally in a garage, 13 people at a small company called Nomadic, and we were building robots. It was the most fun I've had until then in my career. We were soldering and building boards and building robotics back in 1997, and then I became a chip designer later on at a company called Web TV, which was eventually acquired by Microsoft. At that point in time, I decided this is where I wanted to make my home, and it had a little bit to do with the weather. You know, coming from Montreal, where in the winter it's minus And here in the winter, it's about plus 30. I'm talking Celsius. And also with the fact th…

AI assessment note: “Well, it's a lot of luck. It's a little bit of zigzagging”

Q Well, that is very kind, but I would love to kick off today with a little bit about you and the best question of all, which is how did you make your way into the wonderful world of venture and come to be partner at one of the world's leading firms today in the form of Lightspeed?

A Well, it's a lot of luck. It's a little bit of zigzagging, and it's a little bit of making my own luck. So if you hear an accent, Harry, it's because I'm, um, I'm Canadian. So I grew up in, in Montreal, Canada. I studied computer engineering in the nineties, and in the mid nineties, I started to hear about this place called Silicon Valley. Back then, it wasn't necessarily the standard path for people from the University of Waterloo or other places in Canada to make their way out to California. California was viewed as a place of filled with people who eat kale and do a lot of yoga, but not necessarily a Technology Mecca, but you know, what was happening It was magical, and I decided I really wanted to go see what was happening, and so I made my way out here. My first job was literally in a garage, 13 people at a small company called Nomadic, and we were building robots. It was the most fun I've had until then in my career. We were soldering and building boards and building robotics back in 1997, and then I became a chip designer later on at a company called Web TV, which was eventually acquired by Microsoft. At that point in time, I decided this is where I wanted to make my home, and it had a little bit to do with the weather. You know, coming from Montreal, where in the winter it's minus And here in the winter, it's about plus 30. I'm talking Celsius. And also with the fact th…

AI assessment note: “I studied computer engineering in the nineties... made my way out here”

Q Okay, so I should probably read more than I admit to. What's the favorite book and why?

A I should probably read more than I admit to also. I've got two, I don't have a necessarily a favorite book, but there are two books That I've recently read. One I read a dozen years ago. The one I read, the other one I read more recently. The one I read a dozen years ago really changed my outlook on how I go about my life, and it's called Stumbling on Happiness, and it really exposes how your brain can fill in blanks, either in memory or in the way that you forward project, and how those blanks can actually affect outcomes and your reaction to those outcomes, and that affects happiness, that affects investment decisions, that affects How You Act in Your Daily Life. It's actually a really insightful book, and I'd encourage anybody who's interested in understanding their own psychology to read that book, because it'll, it'll shine a better light on how our brain can play tricks on us. And then the other book I read much more recently is a book called How Not to Die. The name of the book hits you in the face, but if you're interested in wellness and longevity, then I'd strongly recommend you read this book, because it shines a light on some of the things that we as a society have done from a dietary perspective. And how that diet is affecting, not deterministically, but potentially our outcomes as, as human beings, and so I read that book. I don't follow it to the T, but it's cert…

AI assessment note: “I don't have a necessarily a favorite book, but there are two books”

Q to move a little bit, though, further deeper into the enter Enterprise space itself, because when we chatted before, you said to me, there's a well-trodden path to five to ten billion dollars in enterprise market caps, but this takes special attention to company design, you said. My question to you here is, what did you mean by the attention to company design? How does that look in your mind?

A Yeah, company design in my mind is an art and a science, and it transcends just product design, and I think what I've seen over my career is a lot of great technologists or Product folks really tend towards my product is the best product, and as a result of that, it should be bought. What I've learned over time is the best enterprise companies, the winners, are those that marry amazing product design, which is a combination of technology architecture plus product, which translates into UI and UX, and marry those with a great go-to-market design. So how do you design the best go-to-market motion for the product that you've built, and then how do you architect the team for both the product and And the go-to-market motion. So it really is designing your company to take advantage of your innovation around both the technology and product and designing the go-to-market motion in a way that is true to your product and finding the people, the execs, as well as the rank and file engineers, salespeople, customer success, customer support, sales engineers, who can actually execute on your, the go-to-market motion that you've designed for your product. Company design, it's thinking holistically about your company, about your people, about your product, and about your go-to-market motion.

AI assessment note: “Company design, it's thinking holistically about your company, about your people, about your product”

Q In terms of kind of execution on the go-to-market, if we take that kind of one logical step further, how do you think about testing for the team's ability to execute on the go-to-market strategy? And how does one plausibly do that in the fundraising environment that is traditionally more compressed now than it has been before?

A That's both an art and a science. So depending on the company stage, if it's a series A, then you look at their prior history. You look at what does that team do? Done before. What have they achieved in their past lives? Because that's in many cases, a good proxy for what they can achieve going forward. If it's a company that's at the later stages, call it series B or beyond, then you've got some data. Then you can really understand how did they land? What is their strategy? Where are they landing? And you can talk to some of these customers either directly or through back channels to really understand how they sold, what their ability to execute on selling was, and why they bought. Sometimes it's just hard to dispute great product market fit. And so companies that find product market fit find lightning in the bottle. Those are the ones you just want to get behind in a big, big way.

AI assessment note: “depending on the company stage, if it's a series A, then you look at their prior history”

Q In terms of kind of execution on the go-to-market, if we take that kind of one logical step further, how do you think about testing for the team's ability to execute on the go-to-market strategy? And how does one plausibly do that in the fundraising environment that is traditionally more compressed now than it has been before?

A That's both an art and a science. So depending on the company stage, if it's a series A, then you look at their prior history. You look at what does that team do? Done before. What have they achieved in their past lives? Because that's in many cases, a good proxy for what they can achieve going forward. If it's a company that's at the later stages, call it series B or beyond, then you've got some data. Then you can really understand how did they land? What is their strategy? Where are they landing? And you can talk to some of these customers either directly or through back channels to really understand how they sold, what their ability to execute on selling was, and why they bought. Sometimes it's just hard to dispute great product market fit. And so companies that find product market fit find lightning in the bottle. Those are the ones you just want to get behind in a big, big way.

AI assessment note: “depending on the company stage, if it's a series A, then you look at their prior history”

Q What's the single biggest challenge of your role with Lightspeed today?

A I absolutely love my job, and the job is an incredible one, but it's one in which there's a lot of context switching. As venture capitalists, we're working with a number of portfolio companies. We're looking at new potential investments. We're thinking strategically about how to go globally, grow globally, for example, and grow our platforms. So I'd say the challenge is really, it's a little bit like an air traffic controller, keeping everything straight in our, in, in our head and staying very, very organized and prioritizing where our time needs to be spent, where my time needs to be spent and why, and then making sure that I'm spending the right amount of time and giving the right amount of energy to the portfolio companies that I work with, as well as to potentially interesting new companies that can become outliers. And then of course, working with my partners here inside the firm to help think through strategically where we're going as a firm.

AI assessment note: “there's a lot of context switching”