The Exchanges

Q Investors are always vocal. I have no fear of that one. But what did you, the second question was, what did you get wrong in the first companies that you aren't repeating with electric today?

A Yeah. Well, you know, if we had three hours to discuss this, I could probably tell you, you know, all 150 things or more that I think we got wrong. But the three biggest things that I constantly think about, and when I give advice to other founders that I constantly harp on is the first is the solution you're delivering has to be a need to have, not a nice to have, full stop. You know, if your business is just clever marketing, or it's just jamming something down a customer's throat with an inside sales You're going to struggle to build a really valuable and during business. And for example, swarm was an awesome tool, but if a retail store didn't have foot traffic analytics, it didn't matter. The show went on. Right. And so that was a lot of the challenges we had in that business was just due to the fact that our customer didn't need the product. The second thing is you really need to play the economics forward and make sure that you actually have a good business managed to get to product market fit and, you know, build something that people like, is there a real business? That ideally becomes a better business over time. So what does the end state look like? Our run and I was first company was an ad network. So no matter how excellent we were at our job, our biggest publishers would outgrow us and churn and due to competition, fixed costs, talent, our margins would actually ge…

AI assessment note: “the three biggest things that I constantly think about”

Q As a VC, I'm totally on your side on that one. Tell me the single best investor meeting you ever had and why?

A Oh man, the first meeting with Bob and Mike from Bessemer, I mean, that'll, that'll probably go down for the rest of my career as like one of the ones that's like hard to top. They were emailing me trying to get in touch and I don't know why, but I just was like not being very responsive. Then when I agreed to meet, I'd Told them that they had to come to my office. So it was, it was the middle of December. And I told them to come to my office at four o'clock on a Friday. And, you know, these guys came down there, you know, bless their hearts at four in the afternoon in the middle of December, it was snowing, but it was the kind of snow, like not like fun snow is like the really wet, like sleet, just gross New York snow. Um, it was just absolutely nasty out. And like, they showed up and it was one of those things where probably the first meeting with a VC that didn't Feel like me pitching some dudes on the other side of the table. Like the two of them, we just hit it off right away and, and just had like a really fun, thoughtful discussion about how we want to, you know, think about building a company. And so by the end, you know, in my head, I was like, I got to work with guys. And Bob shot me an email that night from his iPad. I was like, that was awesome. Like be great to try to do something. That was that.

AI assessment note: “first meeting with a VC that didn't Feel like me pitching”

Q honest, like really, really open and honest about everything. Can I ask, did you have a safe space when the shit hit the fan and things were super tough? Obviously you're honest with the team, but someone in particular, maybe one person who you really go and open up to. And how do you think about like having a safe space for you as a leader, just to unburden yourself?

A Well, yeah, I mean, that's actually probably one of the biggest benefits to having a co-founder or co-founders, right? So for the 10 years that Rud and I worked together, there were some pretty serious ups and downs. And the thing that he and I were always able to do is no matter how gnarly it got, you know, we could always just walk in a conference room, close the door and just sort of look at each other and be like, man, this is sticky. What do you know, what do we do now? Right. And kind of laugh about it. You know, now with electric, I don't having kind of started this one solo, you know, I've really leaned on friends of mine who are founders themselves, you know? And so when things get really tricky, it's always great to just be able to pick up the Phone and call someone who's not affiliated with the company in any formal way. I mean, my very close friend, Josh, who's a multi-time founder now. I remember calling him a while ago when we had some stuff we were dealing with, and I was really bent out of shape and kind of didn't really know what to do. And I called him and yeah, he basically just like made fun of me for like the first part of the call. And I know that, you know, he'd been through some really tough stuff on his end. So it was like in that moment, it just like sort of totally broke the ice. I'm like, all right, well, this guy's basically laughing at me and sort …

AI assessment note: “one of the biggest benefits to having a co-founder or co-founders”

Q So am I, but I would love to kick off today with a little bit on you. So really two questions to set some context. First is how did you make your way into the world of startups? And then the second is what was that aha moment with electric?

A Yeah. Well, when I was a teenager, I just didn't really see why I couldn't start my own company. People said, yeah, you can't start your own company. You're only 16. And I was like, why not? And so the light bulb went off for me. I think one night early on in high school, I realized, Hey, I can do whatever I want. And the next day I started my first company producing mountain biking videos. But yeah. And then it's sort of fast forward to the aha moment with electric. I was actually running my last company in San Francisco. This was maybe 2012. We were using Software for benefits and payroll. And it was a lot easier than doing it the old fashioned way. And so then when we had a whole bunch of it stuff that had to get handled, I just thought to myself, well, Hey, if you can automate HR stuff with software, why can't you automate it stuff with software? Every company needs this. Right. But I had another company to run at the time swarm. Right. So I just kind of put the idea on the shelf for a couple of years. And then fortunately we had a, we had a great exit to group on two years later, and I was able to revisit the idea for electric.

AI assessment note: “if you can automate HR stuff with software, why can't you automate it”

Q Investors are always vocal. I have no fear of that one. But what did you, the second question was, what did you get wrong in the first companies that you aren't repeating with electric today?

A Yeah. Well, you know, if we had three hours to discuss this, I could probably tell you, you know, all 150 things or more that I think we got wrong. But the three biggest things that I constantly think about, and when I give advice to other founders that I constantly harp on is the first is the solution you're delivering has to be a need to have, not a nice to have, full stop. You know, if your business is just clever marketing, or it's just jamming something down a customer's throat with an inside sales You're going to struggle to build a really valuable and during business. And for example, swarm was an awesome tool, but if a retail store didn't have foot traffic analytics, it didn't matter. The show went on. Right. And so that was a lot of the challenges we had in that business was just due to the fact that our customer didn't need the product. The second thing is you really need to play the economics forward and make sure that you actually have a good business managed to get to product market fit and, you know, build something that people like, is there a real business? That ideally becomes a better business over time. So what does the end state look like? Our run and I was first company was an ad network. So no matter how excellent we were at our job, our biggest publishers would outgrow us and churn and due to competition, fixed costs, talent, our margins would actually ge…

AI assessment note: “the three biggest things that I constantly think about... first is the solution”

Q I love that. No, I've had it suggested by one other guest before, and I wanted to read it back when they said it, but I still haven't because I'm shit at reading to be quite frank, but that's on the list. And you've got some incredible investors behind you. Question from Bob Bessemer. How did you decide which investors to work with?

A Uh, well, there's, there's two things. So at the seed stage, VCs always say they add value beyond cash, but If you actually do the best way, and at the seed stage, you need all the help you can get. So you really want a VC that's going to, that's going to be able to step up and support you. Well, the best way to kind of call bullshit on people is just look at the size of the portfolio support team, right? You know, when I, when I met Brad at primary, I saw the size of the fund they were running. I did some math on the management fees they were collecting. And then I saw the size of the, of the team that they had supporting their founders. And I said, geez, these guys aren't taking fat salaries. They're actually redeploying the money into hiring Staff who can help companies like mine. So they're the real deal. I think that's at the seed stage, just, you know, look, look for the, for the real seed stage VCs that are putting their money where their mouth is and building out, you know, really great portfolio support teams. I think as you get to later, later stages, you know, your A or B and beyond, it's really important that some of the big money earlier on is coming from investors who were at one point entrepreneurs in their own right that had real companies, you know, Bob at Bessemer, you know, he had two exits before. Before he became a VC, and he's got a lot of war stories of w…

AI assessment note: “at the seed stage... look at the size of the portfolio support team”

Q So am I, but I would love to kick off today with a little bit on you. So really two questions to set some context. First is how did you make your way into the world of startups? And then the second is what was that aha moment with electric?

A Yeah. Well, when I was a teenager, I just didn't really see why I couldn't start my own company. People said, yeah, you can't start your own company. You're only 16. And I was like, why not? And so the light bulb went off for me. I think one night early on in high school, I realized, Hey, I can do whatever I want. And the next day I started my first company producing mountain biking videos. But yeah. And then it's sort of fast forward to the aha moment with electric. I was actually running my last company in San Francisco. This was maybe 2012. We were using Software for benefits and payroll. And it was a lot easier than doing it the old fashioned way. And so then when we had a whole bunch of it stuff that had to get handled, I just thought to myself, well, Hey, if you can automate HR stuff with software, why can't you automate it stuff with software? Every company needs this. Right. But I had another company to run at the time swarm. Right. So I just kind of put the idea on the shelf for a couple of years. And then fortunately we had a, we had a great exit to group on two years later, and I was able to revisit the idea for electric.

AI assessment note: “if you can automate HR stuff with software, why can't you automate it”

Q get concerned about technical debt accruing in the early days? If the MVP is successful and you get traction, it's easy to kind of pour fuel on the fire of that initial traction and then look back a couple of months later and go, shit, we've got a ton of off-the-shelf components that actually isn't stable enough, isn't secure enough. Is the technical debt question ever a worry for you?

A Always. And it is for every company, right? I think most good engineering teams sort of look at technical debt like a credit card, right? You know, a balance of zero means you're probably not leveraging it enough. And if you owe Amex a 150,000 dollars, that's probably not good either. So there's your stage of business. There's a sort of technical debt balance that you can determine is reasonable to carry, but it's certainly a challenge, even with the best of intentions and even proactively addressing technical debt, you're always probably going to wind up a little bit More than you want, but you've just got to be thoughtful about where you decide to maybe skip some steps for now, as long as you're intentional about revisiting those things later.

AI assessment note: “Always. And it is for every company, right?”

Q at the other end, and you're just ultimately on the back foot when you've raised 30 pre-launch. But I do want to move to the element of leadership, and it's another real passion point of mine. I think it's easy to be a great leader when times are great. It's very difficult and different when times are not so good. How do you feel and think about wartime leadership, Ryan?

A Um, yeah, I've thought a lot about this, particularly, you know, our last two companies were, uh, at times days away from running out of money, and I think in the most extreme case at Swarm, Rudd's wedding was on a Saturday, and we were gonna have to lay everybody off on Monday, and so two days before the wedding, we got a wire for 300 grand, and, and obviously didn't have to lay anyone off, but, um, so definitely had a lot of experiences that have formed my perspective on this. So, you know, the first major takeaway is you just have to be honest. If you're, if you're running out of money or your product sucks or your team hates you, you just kind of acknowledge that. I see a lot of founders that lie to themselves until the very end or, you know, blame other people, but fundamentally you're the CEO, so it really is all your fault. You know, don't get it twisted, right? So that being said, until the last dollar is spent, it's not over. What I've always found is that whatever shit hits the fan, the best thing you can do is take a step back, divorce yourself from the current moment, take out a clean sheet of paper, And just say, okay, where do we need to get to? Like, what does sort of quantitatively and qualitatively success look like? Separate from what you think you can and can't do, or what's possible or not possible, but like, what in a perfect world would that next phase loo…

AI assessment note: “the first major takeaway is you just have to be honest.”

Q prison warden. Now, um, I mean, there's a, I guess, no more blank reference in terms of your ability to achieve what you set out to. In terms of hearing that, Can I ask, how do you balance between the ruthless speed and quality of execution that you inhibit, but also kind of while maintaining the softer side of people management, culture, morale management, how do you balance the two?

A That's the classic Brad comment. So ruthless execution sounds a lot more hardcore than it is. At Electric, when we think about execution, it has a lot more to do with upholding high standards, having excellent focus, delivering in a consistent way. And so that execution really, you can kind of think about it more just Sort of like how a sports team might train for something. And so in terms of how you balance that with culture, I kind of like to think of our office sort of like the Seattle Seahawks locker room when Pete Carroll became a coach, right? So Pete got to the Seahawks and the first thing he said was, Hey, there's, there's not going to be any yelling in this locker room. No name calling, no foul language, no insults. You know, he got all the players doing yoga and like talking to psychiatrists and stuff. And it was like pretty out there for NFL standards, but they went to the Superbowl, right? They didn't win, but they got a lot closer than they had. Before you join. And yeah, I think it's kind of a similar thing here, right? Like we laugh a lot in crack jokes. We play music all over the office. The teams go out and party together. We care about each other's wellbeing and mental health and all that good stuff. But when push comes to shove, we have extremely clear goals, extremely high standards, and everyone's expected to deliver. And so it's so much easier to walk int…

AI assessment note: “so much easier to walk into a situation where you're upholding really high standards”

Q Totally. And I love the analogy to a credit card there, but if you think back to your prior companies, do you have an example of the MVP journey there? And what did you learn?

A Sure. Swarm is a great example. We knew we wanted to measure foot traffic in brick and mortar retail stores and surface the data in a dashboard. So that store owners could see when they were busy or slow, and if their marketing was driving foot traffic, and all those sorts of things. We knew that every cell phone had a Wi-Fi antenna, and so we thought that that was probably the best way to measure the foot traffic. You know, use cell phones as a proxy for people. We could have made that problem as expensive as we wanted from an MVP standpoint. A number of other companies in the space turned it into a very expensive problem. We just didn't have the money to make it an expensive problem. So we postulated, and Rud and I not being RF engineers, so our non-technical brains, sort of figured, like, hey, we could order an open-source Wi-Fi router for a hundred bucks, and our head of engineering could probably rewrite some of the code in the firmware, and then we could probably write a basic integration to pull the data out. With that, you know, we could basically just re-flash the, the, the software and the router to listen for Wi-Fi antennas rather than broadcasting a connection. And, you know, at the time we thought like, this is so freaking simple. Like there's no way it could be this easy to build an analytics foot traffic analytics sensor, just using a hundred dollar wifi router a…

AI assessment note: “Swarm is a great example. We knew we wanted to measure foot traffic”

Q the lean startup and the MVP process hailed for many years, and now the likes of Superhuman and Figma have gone through very heavy development cycles. Figma, in the years case before Before it actually was released. It seems we're going the other way with these amazing success stories. How do you feel and think about this reversion of the lean startup, the MVP? How do you think about that?

A Well, capital markets have become very founder friendly, as you know, therefore giving teams a lot more time to operate on their own schedule. The cost of running a software business is the lowest it's ever been. So it doesn't necessarily cost you a lot to run a pre-revenue business or a low revenue business. For years at a time, even if you want, but at the end of the day, you have to build a business, not a university research project. So there's a point at which you need to get the show on the road and engage in meaningful commercial activity. And so some of these companies that have effectively been in beta and I'm using air quotes, you know, for years, they might be successful to the extent that they have an elegant product that many people like to use, but as businesses, they're probably not all that compelling yet. They may be showing a lot of promise, But ultimately, look at the scoreboard. Is there revenue there? A lot of revenue, then great. But if not, then it's hard to argue that they're a real business yet.

AI assessment note: “as businesses, they're probably not all that compelling yet.”

Q That's absolutely hilarious. Nothing like someone laughing when you're looking for the sympathy. In terms of like the open and direct communication with the team, is it possible, do you think, to be vulnerable, but also a strong leader? It's one kind of dichotomy and balance that I'm always thinking about. Is it possible to have both vulnerability and strength?

A Absolutely. The two actually really, I think, are self-reinforcing. Like, you as a leader have to exhibit a lot of strength in order to sort of have the courage to just own up to things, whether you're stressed or just being honest about things not going well. So a lot of that vulnerability comes from actually a position of strength, not weakness, is something I believe. But then separately, humans categorically aren't stupid, and if all you're ever doing is talking about things in a super positive light, Most people know that that's not the case, and as a result, are going to say, hey, I'm, like, not getting the full story from this guy. So I think that what we've all seen is that some of the strongest leaders are also quite vulnerable and quite transparent about how they're feeling. So again, I think that, I think those two things are self-reinforcing if approached from the right angle.

AI assessment note: “Absolutely. The two actually really, I think, are self-reinforcing.”

Q But I do want to ask one final element on your style of leadership. Because it's ever changing with the scale of the company. So how have you seen your style of CEOship change over the scaling journey? And how does it change from seed to gross?

A That's probably one of the areas where a lot of first time founders, even in my case, you know, third time founder, those transitions can be abrupt. So David Politis from BetterCloud actually wrote a phenomenal blog post on this the other week. So I'm actually going to borrow heavily from that because I think he just absolutely nailed it. The early days, like the sort of one to 30 or 40 years Employees and the, you know, zero to one to two million as a CEO, you're a player coach. So you're doing a lot of jobs as an IC, but you're also managing maybe some frontline folks and you have CEO stuff to do. And it's brutal. Like the context switching is just nightmarish and you're doing a lot of stuff that you're not ever going to be good at in the first place. So I just, having done it now three times, did Because there's absolutely no consistency with what you're doing and everything's a fire that needs to be put out. You know, the next stage company gets a little bigger. You've got some product market fit. There's some repeatability around the revenue as a CEO. That's when you start managing managers, but you're still involved in a lot of the day to day. So this is, I think from a context switching and just a sort of hair on fire standpoint, like this is less hard, but it still involves a ton of decision-making every single day. So like, At this stage, that's really where the decisi…

AI assessment note: “The early days... you're a player coach... The next stage... you start managing managers”

Q Speaking of kind of being fully up and running and doing their job in terms of really getting kind of maximum efficiency from them in that role. I heard from Brad that you're very passionate about leveling up managers internally. How do you think today about leveling up internally and what really works in your experience?

A I'll tell you what doesn't work. The worst thing you can do is have a talented person in the wrong job. And so typically that happens by promoting someone Too fast. And that's going to be for two reasons. One, you're challenged to actually hire someone from the outside and you say, Hey, you know, so-and-so did a great job. Let's promote her into the role. But you've got to be really honest about whether or not that's actually the right call. And so what we do is with every role, we just make a checklist of the non-negotiables, you know, the four or five things that have to happen for someone to be successful in that role. And so when it comes to the decision of, or are we really going to try to push someone up to that role? We can do a pretty quick assessment as to whether or not we think that person can be coached in a reasonable timeframe to hit most or all the marks on that checklist. And based on how the business is scaling, whether or not, you know, they'll, they'll really be able to stay in that role long enough for it to be a good use of everyone's time. And if not, you know, no worries at all, right? A company like ours that goes from four customers and five employees to 300 customers and 150 employees in less than three years. The surface area of the job expands so much that you can't reasonably expect most people to keep up. I mean, even if you didn't promote someone,…

AI assessment note: “we just make a checklist of the non-negotiables, you know, the four or five things”

Q get concerned about technical debt accruing in the early days? If the MVP is successful and you get traction, it's easy to kind of pour fuel on the fire of that initial traction and then look back a couple of months later and go, shit, we've got a ton of off-the-shelf components that actually isn't stable enough, isn't secure enough. Is the technical debt question ever a worry for you?

A Always. And it is for every company, right? I think most good engineering teams sort of look at technical debt like a credit card, right? You know, a balance of zero means you're probably not leveraging it enough. And if you owe Amex a 150,000 dollars, that's probably not good either. So there's your stage of business. There's a sort of technical debt balance that you can determine is reasonable to carry, but it's certainly a challenge, even with the best of intentions and even proactively addressing technical debt, you're always probably going to wind up a little bit More than you want, but you've just got to be thoughtful about where you decide to maybe skip some steps for now, as long as you're intentional about revisiting those things later.

AI assessment note: “Always. And it is for every company, right?”

Q at the other end, and you're just ultimately on the back foot when you've raised 30 pre-launch. But I do want to move to the element of leadership, and it's another real passion point of mine. I think it's easy to be a great leader when times are great. It's very difficult and different when times are not so good. How do you feel and think about wartime leadership, Ryan?

A Um, yeah, I've thought a lot about this, particularly, you know, our last two companies were, uh, at times days away from running out of money, and I think in the most extreme case at Swarm, Rudd's wedding was on a Saturday, and we were gonna have to lay everybody off on Monday, and so two days before the wedding, we got a wire for 300 grand, and, and obviously didn't have to lay anyone off, but, um, so definitely had a lot of experiences that have formed my perspective on this. So, you know, the first major takeaway is you just have to be honest. If you're, if you're running out of money or your product sucks or your team hates you, you just kind of acknowledge that. I see a lot of founders that lie to themselves until the very end or, you know, blame other people, but fundamentally you're the CEO, so it really is all your fault. You know, don't get it twisted, right? So that being said, until the last dollar is spent, it's not over. What I've always found is that whatever shit hits the fan, the best thing you can do is take a step back, divorce yourself from the current moment, take out a clean sheet of paper, And just say, okay, where do we need to get to? Like, what does sort of quantitatively and qualitatively success look like? Separate from what you think you can and can't do, or what's possible or not possible, but like, what in a perfect world would that next phase loo…

AI assessment note: “the first major takeaway is you just have to be honest.”

Q But I do want to ask one final element on your style of leadership. Because it's ever changing with the scale of the company. So how have you seen your style of CEOship change over the scaling journey? And how does it change from seed to gross?

A That's probably one of the areas where a lot of first time founders, even in my case, you know, third time founder, those transitions can be abrupt. So David Politis from BetterCloud actually wrote a phenomenal blog post on this the other week. So I'm actually going to borrow heavily from that because I think he just absolutely nailed it. The early days, like the sort of one to 30 or 40 years Employees and the, you know, zero to one to two million as a CEO, you're a player coach. So you're doing a lot of jobs as an IC, but you're also managing maybe some frontline folks and you have CEO stuff to do. And it's brutal. Like the context switching is just nightmarish and you're doing a lot of stuff that you're not ever going to be good at in the first place. So I just, having done it now three times, did Because there's absolutely no consistency with what you're doing and everything's a fire that needs to be put out. You know, the next stage company gets a little bigger. You've got some product market fit. There's some repeatability around the revenue as a CEO. That's when you start managing managers, but you're still involved in a lot of the day to day. So this is, I think from a context switching and just a sort of hair on fire standpoint, like this is less hard, but it still involves a ton of decision-making every single day. So like, At this stage, that's really where the decisi…

AI assessment note: “The early days... as a CEO, you're a player coach.”

Q the max, and actually, you kind of haven't got the most out of them so far. How do you think about that aligning it to fundraising? Should you start the recruitment process Pre-fundraise. And then what do you do if it goes successfully and you have to hire them quicker? And then there's the cashflow question. How do you think about hiring around fundraisers and how founders could navigate that?

A Yeah. And again, kind of going back to, you know, even the stakes that I made in the early days of this company, you know, of electric is you've got to start ahead of the fundraise and ahead of that next inflection point, because you're going to find yourself having been caught flat footed and needing to execute on a plan that you just simply don't have the People and leadership to do. And so keep in, and keep in mind all this advice is for, you know, companies that are, call it like series A, you know, seed moving on a series A or series B. But if you start hiring six to nine months out, by the time the person actually starts, they're going to need anywhere from one to three months to put all the pieces in place, right? Get their, get their key hires made, get, you know, processes rolled out and clear data that they need to actually start executing on the plan. So before you know it, the thing that they signed up to do is right in front of them, Right. And the right hires, the right, the right executive level hires are going to understand exactly what they're walking into. And they're going to see really clearly if the plan that you're asking them to sign up for is ridiculous and untenable, or you're being a thoughtful leader and you're saying, Hey, you know, it's 2018. Here's my 2019 sales plan. Here's where we are today. And here's what I'm expecting you to do when you come …

AI assessment note: “you've got to start ahead of the fundraise and ahead of that next inflection point”

Q the lean startup and the MVP process hailed for many years, and now the likes of Superhuman and Figma have gone through very heavy development cycles. Figma, in the years case before Before it actually was released. It seems we're going the other way with these amazing success stories. How do you feel and think about this reversion of the lean startup, the MVP? How do you think about that?

A Well, capital markets have become very founder friendly, as you know, therefore giving teams a lot more time to operate on their own schedule. The cost of running a software business is the lowest it's ever been. So it doesn't necessarily cost you a lot to run a pre-revenue business or a low revenue business. For years at a time, even if you want, but at the end of the day, you have to build a business, not a university research project. So there's a point at which you need to get the show on the road and engage in meaningful commercial activity. And so some of these companies that have effectively been in beta and I'm using air quotes, you know, for years, they might be successful to the extent that they have an elegant product that many people like to use, but as businesses, they're probably not all that compelling yet. They may be showing a lot of promise, But ultimately, look at the scoreboard. Is there revenue there? A lot of revenue, then great. But if not, then it's hard to argue that they're a real business yet.

AI assessment note: “at the end of the day, you have to build a business, not a university research project.”

Q That's absolutely hilarious. Nothing like someone laughing when you're looking for the sympathy. In terms of like the open and direct communication with the team, is it possible, do you think, to be vulnerable, but also a strong leader? It's one kind of dichotomy and balance that I'm always thinking about. Is it possible to have both vulnerability and strength?

A Absolutely. The two actually really, I think, are self-reinforcing. Like, you as a leader have to exhibit a lot of strength in order to sort of have the courage to just own up to things, whether you're stressed or just being honest about things not going well. So a lot of that vulnerability comes from actually a position of strength, not weakness, is something I believe. But then separately, humans categorically aren't stupid, and if all you're ever doing is talking about things in a super positive light, Most people know that that's not the case, and as a result, are going to say, hey, I'm, like, not getting the full story from this guy. So I think that what we've all seen is that some of the strongest leaders are also quite vulnerable and quite transparent about how they're feeling. So again, I think that, I think those two things are self-reinforcing if approached from the right angle.

AI assessment note: “Absolutely. The two actually really, I think, are self-reinforcing.”

Q hair on fire, I am super interested before we dive into the team around it, which I do want to touch on. How do you deal with those hair on fire moments? We chatted before about me being slightly manic, sometimes struggling in terms of things getting on top of me. What would you advise me and how do you just get over things getting too on top of you?

A I mean, the most important thing is you got to just trust the process. So if you have a big deal that doesn't go as Through or big customer churns or employee that leaves or, you know, whatever. The most important thing is to really just stick to the things that, you know, work and be really honest about the things that aren't working and make sure that you're being responsible in the way that you're tackling the things that aren't working. And just trust that if you sort of look at your situation and say, okay, we know what's on fire, but we do have a plan and we are chipping away at it. We know what's working and that stuff's Continuing to work. You know, then when things do blow up in your face, you can be a little bit more level-headed about the whole thing because you can put it in context of what's working or what's not and just have a little bit of faith in the processes that you set up.

AI assessment note: “most important thing is you got to just trust the process.”

Q Now, and this sounds very nerdy, but inflection points are actually one of my passion points of mine. How did you determine what the next inflection point was and who's involved in that brainstorming and thought process of what is the next inflection point?

A Well, with a venture-backed company, particularly a B to B SaaS business, there are a lot of commonly accepted metrics of what you need in order to be considered to have gone to the next step, right? So, you know, at the seed stage, you really need to prove that you've got product market fit, or at least sort of the early markings of product market fit and a revenue model that's beginning to come together from C to A, then, you know, you really need to see that there's some, you know, repeatability in the go-to-market and that there's pretty strong product market fit, right? So if You know, I think just depending on the type of business you're running and stage that you're at, particularly if you're venture backed, those inflection points can often be relatively easily defined. Nothing's perfect. Revenue as a marker for product market fit on its own is probably a lazy way to look at it. But most investors are pretty vocal about what they want to see in the next round.

AI assessment note: “most investors are pretty vocal about what they want to see in the next round.”

Q the max, and actually, you kind of haven't got the most out of them so far. How do you think about that aligning it to fundraising? Should you start the recruitment process Pre-fundraise. And then what do you do if it goes successfully and you have to hire them quicker? And then there's the cashflow question. How do you think about hiring around fundraisers and how founders could navigate that?

A Yeah. And again, kind of going back to, you know, even the stakes that I made in the early days of this company, you know, of electric is you've got to start ahead of the fundraise and ahead of that next inflection point, because you're going to find yourself having been caught flat footed and needing to execute on a plan that you just simply don't have the People and leadership to do. And so keep in, and keep in mind all this advice is for, you know, companies that are, call it like series A, you know, seed moving on a series A or series B. But if you start hiring six to nine months out, by the time the person actually starts, they're going to need anywhere from one to three months to put all the pieces in place, right? Get their, get their key hires made, get, you know, processes rolled out and clear data that they need to actually start executing on the plan. So before you know it, the thing that they signed up to do is right in front of them, Right. And the right hires, the right, the right executive level hires are going to understand exactly what they're walking into. And they're going to see really clearly if the plan that you're asking them to sign up for is ridiculous and untenable, or you're being a thoughtful leader and you're saying, Hey, you know, it's 2018. Here's my 2019 sales plan. Here's where we are today. And here's what I'm expecting you to do when you come …

AI assessment note: “you've got to start ahead of the fundraise and ahead of that next inflection point”

Q Now, and this sounds very nerdy, but inflection points are actually one of my passion points of mine. How did you determine what the next inflection point was and who's involved in that brainstorming and thought process of what is the next inflection point?

A Well, with a venture-backed company, particularly a B to B SaaS business, there are a lot of commonly accepted metrics of what you need in order to be considered to have gone to the next step, right? So, you know, at the seed stage, you really need to prove that you've got product market fit, or at least sort of the early markings of product market fit and a revenue model that's beginning to come together from C to A, then, you know, you really need to see that there's some, you know, repeatability in the go-to-market and that there's pretty strong product market fit, right? So if You know, I think just depending on the type of business you're running and stage that you're at, particularly if you're venture backed, those inflection points can often be relatively easily defined. Nothing's perfect. Revenue as a marker for product market fit on its own is probably a lazy way to look at it. But most investors are pretty vocal about what they want to see in the next round.

AI assessment note: “most investors are pretty vocal about what they want to see in the next round.”