The Exchanges

Every argument clarity score on this site is built from rows on this page. Each question and answer was assessed with names hidden, the host's own answers included, on four things from 1 to 5: directness (does it answer the question asked), coherence (do the ideas follow), precision (concrete details and clear references), compression (says a lot per word). The weighted mix (30/30/25/15) is the exchange score. A person's published score averages their exchange scores on raw tape only, at least 8 of them, shrunk toward the cohort mean. Full method →

Jana Messerschmidt no published score: no usable exchanges on raw tape, and a fair score needs 8+ · coarse estimate ≈4.5/5 from 24 produced feed exchanges record → ← everyone

Every exchange below was scored with names hidden, four dimensions each from 1 to 5. An exchange's score is 0.30·directness + 0.30·coherence + 0.25·precision + 0.15·compression. The published score averages the raw tape exchange scores and shrinks small samples toward the cohort mean, so five great answers can't beat twenty good ones. Produced feed rows count only toward coarse estimates, never toward a full score.

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Answered produced feed D 5 · C 5 · P 5 · Cm 5 5.00

Q because I mean, one big thing that concerns me is just the core platforms being your Facebooks of the world, being so inefficient from a UnityCon perspective when it comes to customer acquisition today. How do you think about this core challenge that really is Rather new, given the fact that it didn't used to be anywhere near this expensive. How do you think about that lack of distribution today?

A Oh, well, to quote you, I couldn't agree with you more on this point. So we absolutely look for differentiated distribution advantages. So for companies that we've backed, like Cameo, Goop, and Honest, celebrity networks is really that differentiated distribution advantage. For a company like Bird, where I'm a personal investor, or Lime, I think their distribution advantage is that you actually have physical product in the real world. It's super fun to see people on these scooters, and it constantly is a reminder to jump on one. And then I'll talk about a few examples from my operating career as well. But in the early days of Twitter, we worked closely with a bunch of partners to get Twitter content integrated into whether it was websites, search results, or displayed on air and broadcast programming. And this drove incredibly Incredible numbers of signups because the content was so unique and so newsworthy. And then when I was at Netflix, we found a super inexpensive acquisition and retention channel, which was getting big Netflix buttons on remote controls. And you might say remote controls, like that's an interesting kind of place to advertise. But when you look at the lifetime, a typical remote control will sit in someone's home for five to seven years and So for very, very, very little money, we were getting five to seven years worth of daily impressions, reminding people …

AI assessment note: “you've really got to find that distribution advantage.”

Answered produced feed D 5 · C 5 · P 5 · Cm 5 5.00

Q I'm totally with you there on pretty much all of it. I do have to answer one question that makes me stop is how do you stress test the utility value of a potential angel pre-investment when they say, oh, you know, it's very clear that they have great networks or they can help in whatever way that they can help it. How do you stress test that value pre-investment?

A Two things. So first, for every angel investment that I make, I always explicitly ask the founder, what are you looking for out of your investors? Because I want to see if there's a match of the skills that I could bring to the table, as well as the expectations of whether it's time or commitment, or just like the networks that I have to make sure that it's a good match. The second thing is, is If you're a founder, do your due diligence and do your reference checks on the people that you bring onto the cap table. Even if they're small individual checks, you want to talk to other founders that they backed and make sure that they were actually helpful and picked up the phone or answered the email whenever they got the need for help.

AI assessment note: “do your reference checks on the people that you bring onto the cap table”

Answered produced feed D 5 · C 5 · P 5 · Cm 5 5.00

Q In terms of the need for help, and this is totally off schedule, so forgive me for this, but it does amaze me sometimes. I've made some angel investments before. Investor updates Don't really happen until two months before the round, and then it's a very different story. What's your thinking around investor updates, optimizing around them, and the right way to really play that game as a founder?

A I'm glad you touched on this. So the best scalable way I've seen to leverage your cap table is sending out, whether it's monthly or quarterly updates, and putting your explicit top two or three asks at the beginning of that email. And those asks are usually going to be focused around critical hires, VC introductions, or customer introductions. And so one of my personal investments in a B to B SaaS portfolio company, this company called Mutiny, the founder, she put together this master list of the 100 companies that she wanted to target with her product when she was just getting started. She shared this list with her investors and asked each of us to mark in the Google doc where we knew senior folks. So within a few days, she had direct introductions to executives and decision makers Almost all of the companies on her list. That is a way more efficient way to get into customers than having an SDR going around doing a bunch of cold outreach. So one example of how you can really efficiently use your investor base.

AI assessment note: “sending out, whether it's monthly or quarterly updates, and putting your explicit top two”

Answered produced feed D 5 · C 5 · P 5 · Cm 5 5.00

Q In terms of the need for help, and this is totally off schedule, so forgive me for this, but it does amaze me sometimes. I've made some angel investments before. Investor updates Don't really happen until two months before the round, and then it's a very different story. What's your thinking around investor updates, optimizing around them, and the right way to really play that game as a founder?

A I'm glad you touched on this. So the best scalable way I've seen to leverage your cap table is sending out, whether it's monthly or quarterly updates, and putting your explicit top two or three asks at the beginning of that email. And those asks are usually going to be focused around critical hires, VC introductions, or customer introductions. And so one of my personal investments in a B to B SaaS portfolio company, this company called Mutiny, the founder, she put together this master list of the 100 companies that she wanted to target with her product when she was just getting started. She shared this list with her investors and asked each of us to mark in the Google doc where we knew senior folks. So within a few days, she had direct introductions to executives and decision makers Almost all of the companies on her list. That is a way more efficient way to get into customers than having an SDR going around doing a bunch of cold outreach. So one example of how you can really efficiently use your investor base.

AI assessment note: “sending out, whether it's monthly or quarterly updates, and putting your explicit top two”

Answered produced feed D 5 · C 5 · P 5 · Cm 5 5.00

Q because I mean, one big thing that concerns me is just the core platforms being your Facebooks of the world, being so inefficient from a UnityCon perspective when it comes to customer acquisition today. How do you think about this core challenge that really is Rather new, given the fact that it didn't used to be anywhere near this expensive. How do you think about that lack of distribution today?

A Oh, well, to quote you, I couldn't agree with you more on this point. So we absolutely look for differentiated distribution advantages. So for companies that we've backed, like Cameo, Goop, and Honest, celebrity networks is really that differentiated distribution advantage. For a company like Bird, where I'm a personal investor, or Lime, I think their distribution advantage is that you actually have physical product in the real world. It's super fun to see people on these scooters, and it constantly is a reminder to jump on one. And then I'll talk about a few examples from my operating career as well. But in the early days of Twitter, we worked closely with a bunch of partners to get Twitter content integrated into whether it was websites, search results, or displayed on air and broadcast programming. And this drove incredibly Incredible numbers of signups because the content was so unique and so newsworthy. And then when I was at Netflix, we found a super inexpensive acquisition and retention channel, which was getting big Netflix buttons on remote controls. And you might say remote controls, like that's an interesting kind of place to advertise. But when you look at the lifetime, a typical remote control will sit in someone's home for five to seven years and So for very, very, very little money, we were getting five to seven years worth of daily impressions, reminding people …

AI assessment note: “we absolutely look for differentiated distribution advantages”

Answered produced feed D 5 · C 5 · P 5 · Cm 5 5.00

Q I'm totally with you there on pretty much all of it. I do have to answer one question that makes me stop is how do you stress test the utility value of a potential angel pre-investment when they say, oh, you know, it's very clear that they have great networks or they can help in whatever way that they can help it. How do you stress test that value pre-investment?

A Two things. So first, for every angel investment that I make, I always explicitly ask the founder, what are you looking for out of your investors? Because I want to see if there's a match of the skills that I could bring to the table, as well as the expectations of whether it's time or commitment, or just like the networks that I have to make sure that it's a good match. The second thing is, is If you're a founder, do your due diligence and do your reference checks on the people that you bring onto the cap table. Even if they're small individual checks, you want to talk to other founders that they backed and make sure that they were actually helpful and picked up the phone or answered the email whenever they got the need for help.

AI assessment note: “do your reference checks on the people that you bring onto the cap table”

Answered produced feed D 5 · C 5 · P 5 · Cm 4 4.85

Q time, I think there's actually quite a lot of opaqueness and lack of clarity, actually, for what certain founders maybe need at certain stages. And so very hard of me to ask, and it's all kind of thumb in the air, so to speak, slightly. But just as a ballpark, let's start with, say, a D to C Series A brand. What would those metrics be that you'd look for?

A Yeah, you know, I'll start by saying, of course, it depends to some extent. So I'll give some ballpark numbers. So for DTC brand companies that are raising a Series A, I have two partners, Nicole Quinn and Alex Tosig, who have backed quite a few DTC companies, Daily Harvest and Goop, to name a few. And I've spent a bunch of time with them here as I've been new at Lightspeed. To get a sense of what gets them excited about DTC brands. And I think in general, you're starting to look for a company who's having breakout revenue and maybe approaching the 750 K to a million dollars a month rate. And also you want to see strong growth coming from organic or word of mouth. And these moment in time statistics are important, but so is the velocity of the curve at the point in time which you raise money. So we'd much rather back a company who's gone from like zero to 500 K in a few months with strong organic traffic than a company who hit a million dollars a month rate, but the growth has slowed significantly. So the velocity of the curve going into your fundraise matters quite a bit.

AI assessment note: “approaching the 750 K to a million dollars a month rate”

Answered produced feed D 5 · C 5 · P 5 · Cm 4 4.85

Q a winner. I do have one final one though, before my favorite being the quickfire. And it's the element of ensuring that we really optimize the The cap table and the work with hashtag angels is incredible value and proof of this, but how do you think we can increase female representation, underrepresented minorities on cap tables? What do you think we can do to actively move the needle here?

A So I think the first thing that you have to do is to actually measure the diversity on your cap table. And so I'll give you a little bit of history in terms of how we started focusing on this. So after we had been angel investing for a few years, we had I've never seen enough cap tables to form a point of view and hypothesize that women's representation as employees in tech probably looked vastly different than women's representations as owners in tech. And so we put out this blog post called The Gap Table, and it really was a call to action to the industry that they should start to measure their cap tables, not just measure the representation of their employee bases. And we did this without really having much data. I mean, we had our small sample set of our portfolio companies, and we really were hoping that people would start doing this in earnest. And one of the phenomenal things was that Henry Ward, he's the CEO of Carta, which is both a hashtag angels and Lightspeed portfolio company. He reached out and he said, I've got your data. And so we went into this deep data science project with him and his team, and we analyzed more than Across more than a 180,000 employees to understand how equity is allocated. So we ended up, we use inferred gender amongst founders and employees. And unfortunately we didn't have the right data to look at nine non-binary gender or ethnicity as we…

AI assessment note: “the first thing that you have to do is to actually measure the diversity”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q of the metrics themselves, I had someone the other day on the show say the first Before meeting post their investment, they set the first item on the agenda to be kind of metric setting for the next round. Is that the right time? When should this metric setting be? And should it be with your investors and board that you set the metrics or is it an independent exercise?

A Yeah, great question. So I think you should set those metrics immediately whenever you raise that round. And then you can use every single moment and resource that you have for the next, you know, whether it's 12, 24 months. To hit those metrics and share them with your board or your close group of advisors immediately and get feedback. And the other thing I would add is, is that even though you might have a sense of what you think those metrics look like right now, continue to ask the market because the market shifts and, you know, something that maybe a direct to consumer investor looked for 24 months ago, it might actually start to look different once you're a little bit further out. So continue to go out to the market and make sure that you're getting the right metrics that you're going to be able to easily raise capital.

AI assessment note: “you should set those metrics immediately whenever you raise that round”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q switching to now the side of the table that you're on being the venture side, we see more and more founders raising than ever before. And there's the common suggestion that founders should always be raising. Now there's many opposing views on this one. You've also worn many different hats and seen many different founders raising. So fundamentally should founders always be raising? And how do you think about this?

A Yeah. I love that you asked this question. So first, I think it depends on what your definition of raising is, but here's the deal. Unless you're running a profitable business, you're going to run out of money, typically one to two years after you raise. And so you're absolutely always going to have to raise more capital. So you're actually always raising until you're profitable. So for me, the thing that I always encourage founders to think about is the absolute top level goal of For every founder should be ensuring that they are on track to hit the metrics that they need to raise their next round of capital. So at the early stages of company building, like when you're pre-seed, seed, series A, you really shouldn't be focused on anything else other than do I have the right tactics in place to hit those metrics that are going to give you more money. So I've backed more than 50 early stage companies myself as an angel investor, and I've looked at over a thousand pitches at this point. And I am always surprised by how few founders that I talk to really have a clear sense of what it will take to be in a good position to raise a series A or whatever their next round is.

AI assessment note: “you're actually always raising until you're profitable.”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q I mean, that is incredible from the remote perspective. I didn't know that. And what a hack that is. I do have to ask, kind of speaking of the metrics that we look Or is investors and naturally incites the investing class. When founders ask investors, one, should investors give clear metrics of what they're looking for? And two, what should founders do if they don't?

A Yes. So founders should constantly ask investors what those metrics are. And I believe that if VCs are interested in the business, they should take the time and do the work to tell you. Because each business is going to be a little bit nuanced. There's some general guidelines for things like DTC or subscription But businesses are usually more nuanced than that. And so make VC do the work. Make them go through the mental exercise to think through what would it take to back your business. I think also, like, if you already have existing institutional investors on your cap table, obviously ask them. They've seen this play out with a ton of other companies in their portfolio. But in general, make your VCs, whether it's your existing ones or ones you might want to partner with in the future, do the work.

AI assessment note: “if VCs are interested in the business, they should take the time”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q switching to now the side of the table that you're on being the venture side, we see more and more founders raising than ever before. And there's the common suggestion that founders should always be raising. Now there's many opposing views on this one. You've also worn many different hats and seen many different founders raising. So fundamentally should founders always be raising? And how do you think about this?

A Yeah. I love that you asked this question. So first, I think it depends on what your definition of raising is, but here's the deal. Unless you're running a profitable business, you're going to run out of money, typically one to two years after you raise. And so you're absolutely always going to have to raise more capital. So you're actually always raising until you're profitable. So for me, the thing that I always encourage founders to think about is the absolute top level goal of For every founder should be ensuring that they are on track to hit the metrics that they need to raise their next round of capital. So at the early stages of company building, like when you're pre-seed, seed, series A, you really shouldn't be focused on anything else other than do I have the right tactics in place to hit those metrics that are going to give you more money. So I've backed more than 50 early stage companies myself as an angel investor, and I've looked at over a thousand pitches at this point. And I am always surprised by how few founders that I talk to really have a clear sense of what it will take to be in a good position to raise a series A or whatever their next round is.

AI assessment note: “So you're actually always raising until you're profitable.”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q I mean, that is incredible from the remote perspective. I didn't know that. And what a hack that is. I do have to ask, kind of speaking of the metrics that we look Or is investors and naturally incites the investing class. When founders ask investors, one, should investors give clear metrics of what they're looking for? And two, what should founders do if they don't?

A Yes. So founders should constantly ask investors what those metrics are. And I believe that if VCs are interested in the business, they should take the time and do the work to tell you. Because each business is going to be a little bit nuanced. There's some general guidelines for things like DTC or subscription But businesses are usually more nuanced than that. And so make VC do the work. Make them go through the mental exercise to think through what would it take to back your business. I think also, like, if you already have existing institutional investors on your cap table, obviously ask them. They've seen this play out with a ton of other companies in their portfolio. But in general, make your VCs, whether it's your existing ones or ones you might want to partner with in the future, do the work.

AI assessment note: “if VCs are interested in the business, they should take the time and do the work”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q Totally. And so let's, let's say we did hit them and we've got our lead. If we think about the wider cap table, what do you think? And this is really interesting considering, well, A, the 50 angel deals you've done, but also the hashtag angels experience. What do you think are the biggest consideration points for founders when it comes to constructing that cap table?

A I'm so glad you asked. This is one of my favorite things to talk about is, uh, cap tables. So I think in general, depending on the stage of the raise, you're going to either want to have a lead or a co-lead of institutional investors. You want to avoid party rounds, but there's usually some allocation that you can leave over to bring strategic angels or individuals onto the cap table. And I found that these individual angel investors who are fellow founders or operators have Can be incredibly valuable. It's kind of the best of both worlds. You're getting both their money and To give you their time. By the way, like little hidden secret in the industry, I think we all call these individuals angels, but many individual investors will invest in companies and anything from pre-seed to growth when it's a super hot company. So don't just think of angels as like, oh, I can only bring them in when I'm doing my pre-seed or my seed. If there are operators or founders who are going to be valuable to you at a series A or series B or series C, it's okay to bring them in at later rounds. I've personally written a handful of checks into series A or later companies that I just think are rocket ship opportunities. And then I would recommend thinking about the cap table, kind of the way you think about hiring. They're taking up a seat. So how are they going to add differentiated value to who you…

AI assessment note: “I would recommend thinking about the cap table, kind of the way you think about hiring.”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q of the metrics themselves, I had someone the other day on the show say the first Before meeting post their investment, they set the first item on the agenda to be kind of metric setting for the next round. Is that the right time? When should this metric setting be? And should it be with your investors and board that you set the metrics or is it an independent exercise?

A Yeah, great question. So I think you should set those metrics immediately whenever you raise that round. And then you can use every single moment and resource that you have for the next, you know, whether it's 12, 24 months. To hit those metrics and share them with your board or your close group of advisors immediately and get feedback. And the other thing I would add is, is that even though you might have a sense of what you think those metrics look like right now, continue to ask the market because the market shifts and, you know, something that maybe a direct to consumer investor looked for 24 months ago, it might actually start to look different once you're a little bit further out. So continue to go out to the market and make sure that you're getting the right metrics that you're going to be able to easily raise capital.

AI assessment note: “I think you should set those metrics immediately whenever you raise that round.”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q No, I absolutely love that. I only read the trashy celebrity autobiography. So I mean, if you can get a part of Reading intertwined. Tell me, what's been the biggest surprise about the move to VC?

A Oh gosh, there have been a lot of surprises. So I would say the bulk of kind of like the day-to-day adventure seems super You spend most of your time with founders, whether meeting new ones or spending time with people that you've already invested in, and that is by far the best part of the job, like by far. I think the major difference is the decision-making criteria of investing. So as an angel investor, I could make maybe 10 investments a year, usually based off of spending a few hours with the founder, with maybe a little data and progress if they had actually started shipping something, but mostly based on gut intuition on team product and market. And you're also like really involved the first few years when you're an angel investor, but it usually starts to taper off as they have raised additional capital and bring on more experienced executive teams. I think like compare that to a venture investor and you make far fewer investments and you're committing to potentially spending a decade or more deeply involved in the company. So it definitely has a very different deal in terms of the level of commitment and what you're signing up for.

AI assessment note: “I think the major difference is the decision-making criteria of investing.”

Answered produced feed D 4 · C 5 · P 5 · Cm 4 4.55

Q time, I think there's actually quite a lot of opaqueness and lack of clarity, actually, for what certain founders maybe need at certain stages. And so very hard of me to ask, and it's all kind of thumb in the air, so to speak, slightly. But just as a ballpark, let's start with, say, a D to C Series A brand. What would those metrics be that you'd look for?

A Yeah, you know, I'll start by saying, of course, it depends to some extent. So I'll give some ballpark numbers. So for DTC brand companies that are raising a Series A, I have two partners, Nicole Quinn and Alex Tosig, who have backed quite a few DTC companies, Daily Harvest and Goop, to name a few. And I've spent a bunch of time with them here as I've been new at Lightspeed. To get a sense of what gets them excited about DTC brands. And I think in general, you're starting to look for a company who's having breakout revenue and maybe approaching the 750 K to a million dollars a month rate. And also you want to see strong growth coming from organic or word of mouth. And these moment in time statistics are important, but so is the velocity of the curve at the point in time which you raise money. So we'd much rather back a company who's gone from like zero to 500 K in a few months with strong organic traffic than a company who hit a million dollars a month rate, but the growth has slowed significantly. So the velocity of the curve going into your fundraise matters quite a bit.

AI assessment note: “approaching the 750 K to a million dollars a month rate”

Answered produced feed D 5 · C 4 · P 4 · Cm 4 4.30

Q Totally. And so let's, let's say we did hit them and we've got our lead. If we think about the wider cap table, what do you think? And this is really interesting considering, well, A, the 50 angel deals you've done, but also the hashtag angels experience. What do you think are the biggest consideration points for founders when it comes to constructing that cap table?

A I'm so glad you asked. This is one of my favorite things to talk about is, uh, cap tables. So I think in general, depending on the stage of the raise, you're going to either want to have a lead or a co-lead of institutional investors. You want to avoid party rounds, but there's usually some allocation that you can leave over to bring strategic angels or individuals onto the cap table. And I found that these individual angel investors who are fellow founders or operators have Can be incredibly valuable. It's kind of the best of both worlds. You're getting both their money and To give you their time. By the way, like little hidden secret in the industry, I think we all call these individuals angels, but many individual investors will invest in companies and anything from pre-seed to growth when it's a super hot company. So don't just think of angels as like, oh, I can only bring them in when I'm doing my pre-seed or my seed. If there are operators or founders who are going to be valuable to you at a series A or series B or series C, it's okay to bring them in at later rounds. I've personally written a handful of checks into series A or later companies that I just think are rocket ship opportunities. And then I would recommend thinking about the cap table, kind of the way you think about hiring. They're taking up a seat. So how are they going to add differentiated value to who you…

AI assessment note: “recommend thinking about the cap table, kind of the way you think about hiring.”

Answered produced feed D 5 · C 4 · P 3 · Cm 4 4.05

Q Can I ask, and this is really unfair of me, what if the numbers aren't there? Is there a way to gain leverage without blowing out the water numbers that are incredible?

A That's a really good question. I think that For founders who their metrics aren't quite there, I think you have to really be able to tell a story around what changes you're going to make to get them there as quickly as possible. And that might be, you know, what is your unique skill set as a founder, as a team, that you're going to be able to have some explosive growth curve. It also might be that you've just iterated on some of the wrong experiments that just didn't get you to the metrics that you wanted. But I think the best way to be in a great position for a fundraise is that whatever metrics you kind of knew you had to hit, you're hitting them and hopefully you're blowing by them.

AI assessment note: “tell a story around what changes you're going to make to get them there”

Partly produced feed D 3 · C 4 · P 5 · Cm 4 3.95

Q a winner. I do have one final one though, before my favorite being the quickfire. And it's the element of ensuring that we really optimize the The cap table and the work with hashtag angels is incredible value and proof of this, but how do you think we can increase female representation, underrepresented minorities on cap tables? What do you think we can do to actively move the needle here?

A So I think the first thing that you have to do is to actually measure the diversity on your cap table. And so I'll give you a little bit of history in terms of how we started focusing on this. So after we had been angel investing for a few years, we had I've never seen enough cap tables to form a point of view and hypothesize that women's representation as employees in tech probably looked vastly different than women's representations as owners in tech. And so we put out this blog post called The Gap Table, and it really was a call to action to the industry that they should start to measure their cap tables, not just measure the representation of their employee bases. And we did this without really having much data. I mean, we had our small sample set of our portfolio companies, and we really were hoping that people would start doing this in earnest. And one of the phenomenal things was that Henry Ward, he's the CEO of Carta, which is both a hashtag angels and Lightspeed portfolio company. He reached out and he said, I've got your data. And so we went into this deep data science project with him and his team, and we analyzed more than Across more than a 180,000 employees to understand how equity is allocated. So we ended up, we use inferred gender amongst founders and employees. And unfortunately we didn't have the right data to look at nine non-binary gender or ethnicity as we…

AI assessment note: “first thing that you have to do is to actually measure the diversity”

Answered produced feed D 4 · C 4 · P 4 · Cm 3 3.85

Q No, I absolutely love that. I only read the trashy celebrity autobiography. So I mean, if you can get a part of Reading intertwined. Tell me, what's been the biggest surprise about the move to VC?

A Oh gosh, there have been a lot of surprises. So I would say the bulk of kind of like the day-to-day adventure seems super You spend most of your time with founders, whether meeting new ones or spending time with people that you've already invested in, and that is by far the best part of the job, like by far. I think the major difference is the decision-making criteria of investing. So as an angel investor, I could make maybe 10 investments a year, usually based off of spending a few hours with the founder, with maybe a little data and progress if they had actually started shipping something, but mostly based on gut intuition on team product and market. And you're also like really involved the first few years when you're an angel investor, but it usually starts to taper off as they have raised additional capital and bring on more experienced executive teams. I think like compare that to a venture investor and you make far fewer investments and you're committing to potentially spending a decade or more deeply involved in the company. So it definitely has a very different deal in terms of the level of commitment and what you're signing up for.

AI assessment note: “I think the major difference is the decision-making criteria of investing.”

Redirected produced feed D 2 · C 5 · P 5 · Cm 3 3.80

Q Well, that is very, very kind, and I promise to pay you later for that, but I would love to kick off with a little bit on you. So tell me, from engineering to business, from Netflix to Twitter to hashtag angels, what was the moment that you realized venture was And how did that translate to being a partner today at Lightspeed?

A Yeah, you know, I'll start at the beginning. So I grew up in a really small rural town in the Midwest. It's called Manitow, Illinois. Don't worry if you haven't heard of it. It's population, 1621 people. And most people in my town were either farmers or they've worked nearby in Peoria, Illinois at Caterpillar. And so I started getting interested in technology when I was in junior high, Thanksgiving. Based on the influence of my dad, who could definitely just be described as a gadget guy. So we would go to Circa City and Best Buy on the weekends and drool over all of the new electronics. And in high school, I finally was able to upgrade like my decade plus old Apple IIe to this beautiful HP desktop computer with a 166 megahertz processor and a way to connect to the internet. And I was hooked immediately. So when I was trying to figure out what I wanted to major in, my guiding principle that kind of got me to becoming an engineer was, I just really wanted to know, how does this computer work? And so I decided to major in computer engineering, and I didn't know a single engineer in my life. I had definitely never heard of venture capital, despite graduating from high school in 97, which was during the first tech boom. But I just took a leap and wanted to learn about something that I was interested in. And I think that's a trend that's continued. Which is find something that's real…

AI assessment note: “I'll start at the beginning. So I grew up in a really small rural town”

Partly produced feed D 3 · C 4 · P 5 · Cm 3 3.80

Q Well, that is very, very kind, and I promise to pay you later for that, but I would love to kick off with a little bit on you. So tell me, from engineering to business, from Netflix to Twitter to hashtag angels, what was the moment that you realized venture was And how did that translate to being a partner today at Lightspeed?

A Yeah, you know, I'll start at the beginning. So I grew up in a really small rural town in the Midwest. It's called Manitow, Illinois. Don't worry if you haven't heard of it. It's population, 1621 people. And most people in my town were either farmers or they've worked nearby in Peoria, Illinois at Caterpillar. And so I started getting interested in technology when I was in junior high, Thanksgiving. Based on the influence of my dad, who could definitely just be described as a gadget guy. So we would go to Circa City and Best Buy on the weekends and drool over all of the new electronics. And in high school, I finally was able to upgrade like my decade plus old Apple IIe to this beautiful HP desktop computer with a 166 megahertz processor and a way to connect to the internet. And I was hooked immediately. So when I was trying to figure out what I wanted to major in, my guiding principle that kind of got me to becoming an engineer was, I just really wanted to know, how does this computer work? And so I decided to major in computer engineering, and I didn't know a single engineer in my life. I had definitely never heard of venture capital, despite graduating from high school in 97, which was during the first tech boom. But I just took a leap and wanted to learn about something that I was interested in. And I think that's a trend that's continued. Which is find something that's real…

AI assessment note: “it wasn't until about five years ago that I'd ever considered making”

Answered produced feed D 4 · C 4 · P 3 · Cm 3 3.60

Q Can I ask, and this is really unfair of me, what if the numbers aren't there? Is there a way to gain leverage without blowing out the water numbers that are incredible?

A That's a really good question. I think that For founders who their metrics aren't quite there, I think you have to really be able to tell a story around what changes you're going to make to get them there as quickly as possible. And that might be, you know, what is your unique skill set as a founder, as a team, that you're going to be able to have some explosive growth curve. It also might be that you've just iterated on some of the wrong experiments that just didn't get you to the metrics that you wanted. But I think the best way to be in a great position for a fundraise is that whatever metrics you kind of knew you had to hit, you're hitting them and hopefully you're blowing by them.

AI assessment note: “tell a story around what changes you're going to make to get them there”

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