The Exchanges

Q So how do you adopt that as an enterprise company? Because although I completely understand your Equinoxes are the, the, uh, brands they're attracted to, and they don't change people, but how, how do you translate that message in that brand?

A Yeah, it's a, it's a good question. I think honestly, all it has to do with is empathy with who your audience is. Um, the, the way that we run things that immediately, for instance, the number one priority, we say, if nothing else happens in your workday, you have to have to talk to at least one user or one customer every single day. And that just creates a really profound sense of connection and empathy with the end user. And then whoever it is that is writing the, the copy for the app store description, or that is coming up With the design for our website, or, or the script for our video, they are so in contact, in touch with how the mind of the target audience works, and what their lifestyle is like, and what they're expecting, what they're passionate about, that they couldn't even write something that is completely tone deaf, as, as most of the marketing that you see in traditional enterprise software is. And so, I think good marketing is all about empathy. And, and building a brand around your product is, is, is the exact same thing. And, and I think that companies have to really embody it and live it. I mean, you, you can't, you, you can try to hire like a LA brand firm that, that worked with Snapchat and Tinder and have them try and kind of craft the brand for you. But I think it will just come off as inauthentic if you're not actually living it inside of the company. I …

AI assessment note: “I think honestly, all it has to do with is empathy with who your audience is.”

Q Is there an enterprise company at the moment who you think has done really well at conveying this brand?

A Um, that's a good question. You know, um, there are certainly companies that, that are doing a really good job Compared to kind of what we're used to. You have, you have the slacks of the world, which, you know, um, the, the famous, we don't sell saddles, and, and is the, is the same, is the same kind of concept where, where Stuart was very clear about their selling a, a better way of lifestyle productivity, better way of living through your work rather than just a software product. Um, there's, there's companies like Greenhouse that, that comes to mind, the HR space that, Just a disaster of a space, um, where, where they came in with really elegant technology and, and messaging really directed at the end user who's going to end up spending time in the product. And so there are companies that are, that are certainly paying attention and doing a great job.

AI assessment note: “You have the slacks of the world... There's companies like Greenhouse that comes to mind”

Q And would you say then, with that in mind, that your attitude having raised the money since, is it a move fast and break things, or is it a slowly adopt new strategies and kind of A-B test them quietly until you find one that's effective?

A I think, I think in today's world, you have to do Both at the same time. Um, the number one value that we have at immediately is thoughtfulness. Um, for instance, um, everybody gets to work from home Monday morning until noon, because then at noon, everybody's expected to come in and have really thought through how they want to invest the most precious resource that we have, which is their time for, for the balance of the week in order to really move the needle for the company. And so we, we tend to be very thoughtful and methodical That said, we, we have done things like completely make one 80 on our business model week over week and, and, and go from, um, go from charging the end user to deciding not to charge the end user and, and, and eliminate the barriers to entry, um, for anybody to get on a product. And, and those are things that, that, you know, are the result of, of intense communication sometimes happen extremely rapidly, but, but there has to be that thoughtfulness that it's all predicated upon.

AI assessment note: “I think in today's world, you have to do Both at the same time.”

Q Now, I want to hit the ground running by, by starting off with you. So, tell me, how did you come to be the founder and CEO of Immediately? What's the story?

A Yeah, um, well, you know, my biggest passion in life is better understanding how we humans work, right? And, and what gets us excited. What makes it such that some days we feel at the top of the world than others, it's, it's like hard to power through the day. Spend a lot of time thinking about what gives people that mythical state of flow. Where time just becomes more fluid, and we're fully immersed in whatever we're doing at the moment. And, and studying cognition in college, I, I kept realizing how easily technology that, that's supposed to help productivity can actually become really destructive. Um, it, it, it's not so long ago that I was in college, and, and the iPhone was already ubiquitous, and so, we were all carrying around a supercomputer in our pocket, constantly buzzing with new information, right? And, and, and, and I kind of realized Wow, it becomes borderline impossible to maintain full focus on a task for more than five minutes, and, and cognitive science tells us that it takes up to 15 minutes to really fully immerse yourself in a task, and so I realized there's a real tension where technology's supposed to help us, but if it doesn't thoughtfully map onto an optimal flow the way that we need it to, it can actually hurt focus and productivity, and that's what originally got me and my co-founder James Excited about building more elegant productivity technology. …

AI assessment note: “that's what originally got me and my co-founder James Excited about building”

Q Fantastic. And then takeaways of the first fundraising experience with immediately, what have been your big learnings?

A Um, big learnings don't go out until you're ready. Um, I think a lot of founders kind of take whatever, whatever piece of wisdom or truism they get about, you should be raising when you have six months runway left, or when you get your first or third customer, whatever it is, that's not necessarily true. You should be raising when in your mind You are truly, genuinely, in your heart of hearts convinced that the investor would, would be, would be remiss not to make the investment. If you're going out with a feeling of, fuck, this is stressful, but I really hope that it works out, I really hope that I can tell the story well and convince the investor to give me the money so I can make this happen, that comes across and it often doesn't happen. It's better to err on the side of going out a month later once you feel really, really strong in the narrative that you have.

AI assessment note: “big learnings don't go out until you're ready.”

Q And would you say then, with that in mind, that your attitude having raised the money since, is it a move fast and break things, or is it a slowly adopt new strategies and kind of A-B test them quietly until you find one that's effective?

A I think, I think in today's world, you have to do Both at the same time. Um, the number one value that we have at immediately is thoughtfulness. Um, for instance, um, everybody gets to work from home Monday morning until noon, because then at noon, everybody's expected to come in and have really thought through how they want to invest the most precious resource that we have, which is their time for, for the balance of the week in order to really move the needle for the company. And so we, we tend to be very thoughtful and methodical That said, we, we have done things like completely make one 80 on our business model week over week and, and, and go from, um, go from charging the end user to deciding not to charge the end user and, and, and eliminate the barriers to entry, um, for anybody to get on a product. And, and those are things that, that, you know, are the result of, of intense communication sometimes happen extremely rapidly, but, but there has to be that thoughtfulness that it's all predicated upon.

AI assessment note: “you have to do Both at the same time.”

Q the products in terms of just the user's been designed to come first by you guys. And it's very much a mobile first product. So, so why did you choose this approach? Was this in line with the fact that we're all on demand workforce nowadays, and we're moving away from sitting in an HQ in an office all day? What, why did you go for this mobile first approach?

A Yeah, you know, that's a part of it. Um, Um, a key insight that we had early on was that in order to be successful with salespeople, we can't just build and sell a piece of software. What we're bringing to the market is a lifestyle. It's an aspirational lifestyle that is more in keeping with what motivates the millennial salesperson. You know, there's this old perception of the coin operated salesperson is just motivated by money, but, but that couldn't be further from the further away from today's reality. Um, really it's, it's a fun, dynamic, enriching lifestyle that is the draw for somebody to choose sales as their career. And, and with millennials, lifestyle comes first. And so what we hear over and over again are, are things like, you know, what motivated me to become a salesperson was the idea of building relationships with the client, having a dynamic day to day that is not just spent in front of a computer, having my job be more seamlessly integrated into my lifestyle. And, and we realized that if we want to be successful, What we're doing is trying to enable that lifestyle of, you know, closing deals from the baseball game and becoming friends with the customer once the deal is done. And, and so we started out by thinking about that, and then we realized, well, obviously we have to build from home first, because we, we need to build a product that is, that is powerful …

AI assessment note: “mainly that the sales rep can bring with them anywhere that the customer is”

Q So how do you adopt that as an enterprise company? Because although I completely understand your Equinoxes are the, the, uh, brands they're attracted to, and they don't change people, but how, how do you translate that message in that brand?

A Yeah, it's a, it's a good question. I think honestly, all it has to do with is empathy with who your audience is. Um, the, the way that we run things that immediately, for instance, the number one priority, we say, if nothing else happens in your workday, you have to have to talk to at least one user or one customer every single day. And that just creates a really profound sense of connection and empathy with the end user. And then whoever it is that is writing the, the copy for the app store description, or that is coming up With the design for our website, or, or the script for our video, they are so in contact, in touch with how the mind of the target audience works, and what their lifestyle is like, and what they're expecting, what they're passionate about, that they couldn't even write something that is completely tone deaf, as, as most of the marketing that you see in traditional enterprise software is. And so, I think good marketing is all about empathy. And, and building a brand around your product is, is, is the exact same thing. And, and I think that companies have to really embody it and live it. I mean, you, you can't, you, you can try to hire like a LA brand firm that, that worked with Snapchat and Tinder and have them try and kind of craft the brand for you. But I think it will just come off as inauthentic if you're not actually living it inside of the company. I …

AI assessment note: “all it has to do with is empathy with who your audience is”

Q with This user-first approach, uh, to the enterprise, you know, we've seen it potentially with the likes of Slack. Is this the symbolism of a new wave of enterprise technology, do you think, in the past couple of years, where users have become first, and we're not selling to, to particular people in the enterprise, and we're not trying to impress them, you know, we're going for the roots-up approach?

A Yeah, I, I really believe that, that that is the way that things are increasingly going to be in the enterprise. Consumerization of the enterprise is a very real trend. You know, the, the expectations for technology have changed a lot with millennials. We used to be excited to download, like, the coolest new ringtone onto our phone and, and organize all our photos neatly into our Facebook albums with funny titles, and, and now fast forward a couple years, and, and we all have the exact same default ringtone that we never bother to change, and we post our photos onto Snapchat where they disappear in, like, three seconds. We just want for technology to work and get out of the way, And, and you want for it to map onto our authentic natural way of being. And, and, you know, the same thing is starting to be reflected in enterprise technology. It historically has always lagged behind the latest in consumer. And, and that's been especially true of sales software where we operate, but, but it's increasingly becoming a huge point of friction because more and more of today's entry-level workforce generation will often just not put up with clunky software. When you think about how they live, First thing they do after they open their eyes in the morning is check their Instagram, check their Tinder, and, and hit the gym at Equinox. And that's the expectation that they have for user experien…

AI assessment note: “Yeah, I, I really believe that, that that is the way that things are”

Q What the fuck is, uh, Anyway. And then favorite productivity tools. You said distracted on your computer and on your phone. What do you use to keep you productive? Please help me.

A Yeah. Well, um, as silly as it may sound and, and, and you bring the point of being distracted and that being a problem for me, the, the real productivity tool is a Moleskine notebook and pen. I find that the quality of thinking really varies tremendously with the environment and The state that we find ourselves in. And in a startup, you're really trying to beat the odds. And the only way to do that if you have less resources than the incumbent is to have higher quality thinking, to make better decisions, to be smarter. And so I try to carve out time every day to sit somewhere quiet with a nice view and, and think about what the highest leverage things are that I can do for the company to thrive. And I write those down in my notebook. That, that's my productivity hack. Um, but as far as the company, um, Um, like I said, we're obsessed with talking to users every day, and so we've been really in love with Intercom and their suite of tools that enable real-time direct communication with the user, and we actually have it hooked up to our Slack, and so the entire company sees at all times what our users are saying and asking about, and we found that to be really powerful.

AI assessment note: “the real productivity tool is a Moleskine notebook and pen”

Q And then I have to ask one final question before we dive in. With the investors, there is 79, according to AngelList, which, uh, Is, is our bible for today. So, so the 79 investors, that's quite a lot for such an early stage. What do you make of the congested cap table then? Is that a problem for you? Is that something that weighs on your mind?

A You know, it, it doesn't weigh on my mind all that much. Um, many of these investors invested through the AngelList vehicle, and so they're, they're actually a single line item on the cap table. Um, but yeah, we have, we have quite a few And, and every single one of them has, has in some sense been, been instrumental to getting us where we are. And so I am grateful to have them and not burdened by it. And, and, you know, looking ahead, we're now at the point where. We're only going to be, in, in, in every subsequent round, adding one or two or potentially three new line items to, to the cap table, because it's all going to be, um, larger institutional checks, and so don't overdo anything, but, but I am actually extremely glad that, that we ended up inviting all the folks that we did into our rounds, because it really kind of matters, um, especially when you're a To have that big a team of supporters.

AI assessment note: “You know, it, it doesn't weigh on my mind all that much.”

Q Now, I want to hit the ground running by, by starting off with you. So, tell me, how did you come to be the founder and CEO of Immediately? What's the story?

A Yeah, um, well, you know, my biggest passion in life is better understanding how we humans work, right? And, and what gets us excited. What makes it such that some days we feel at the top of the world than others, it's, it's like hard to power through the day. Spend a lot of time thinking about what gives people that mythical state of flow. Where time just becomes more fluid, and we're fully immersed in whatever we're doing at the moment. And, and studying cognition in college, I, I kept realizing how easily technology that, that's supposed to help productivity can actually become really destructive. Um, it, it, it's not so long ago that I was in college, and, and the iPhone was already ubiquitous, and so, we were all carrying around a supercomputer in our pocket, constantly buzzing with new information, right? And, and, and, and I kind of realized Wow, it becomes borderline impossible to maintain full focus on a task for more than five minutes, and, and cognitive science tells us that it takes up to 15 minutes to really fully immerse yourself in a task, and so I realized there's a real tension where technology's supposed to help us, but if it doesn't thoughtfully map onto an optimal flow the way that we need it to, it can actually hurt focus and productivity, and that's what originally got me and my co-founder James Excited about building more elegant productivity technology. …

AI assessment note: “that's what originally got me and my co-founder James Excited about building”

Q with This user-first approach, uh, to the enterprise, you know, we've seen it potentially with the likes of Slack. Is this the symbolism of a new wave of enterprise technology, do you think, in the past couple of years, where users have become first, and we're not selling to, to particular people in the enterprise, and we're not trying to impress them, you know, we're going for the roots-up approach?

A Yeah, I, I really believe that, that that is the way that things are increasingly going to be in the enterprise. Consumerization of the enterprise is a very real trend. You know, the, the expectations for technology have changed a lot with millennials. We used to be excited to download, like, the coolest new ringtone onto our phone and, and organize all our photos neatly into our Facebook albums with funny titles, and, and now fast forward a couple years, and, and we all have the exact same default ringtone that we never bother to change, and we post our photos onto Snapchat where they disappear in, like, three seconds. We just want for technology to work and get out of the way, And, and you want for it to map onto our authentic natural way of being. And, and, you know, the same thing is starting to be reflected in enterprise technology. It historically has always lagged behind the latest in consumer. And, and that's been especially true of sales software where we operate, but, but it's increasingly becoming a huge point of friction because more and more of today's entry-level workforce generation will often just not put up with clunky software. When you think about how they live, First thing they do after they open their eyes in the morning is check their Instagram, check their Tinder, and, and hit the gym at Equinox. And that's the expectation that they have for user experien…

AI assessment note: “I really believe that, that that is the way that things are increasingly going to be”

Q Fantastic. And then takeaways of the first fundraising experience with immediately, what have been your big learnings?

A Um, big learnings don't go out until you're ready. Um, I think a lot of founders kind of take whatever, whatever piece of wisdom or truism they get about, you should be raising when you have six months runway left, or when you get your first or third customer, whatever it is, that's not necessarily true. You should be raising when in your mind You are truly, genuinely, in your heart of hearts convinced that the investor would, would be, would be remiss not to make the investment. If you're going out with a feeling of, fuck, this is stressful, but I really hope that it works out, I really hope that I can tell the story well and convince the investor to give me the money so I can make this happen, that comes across and it often doesn't happen. It's better to err on the side of going out a month later once you feel really, really strong in the narrative that you have.

AI assessment note: “big learnings don't go out until you're ready”

Q the products in terms of just the user's been designed to come first by you guys. And it's very much a mobile first product. So, so why did you choose this approach? Was this in line with the fact that we're all on demand workforce nowadays, and we're moving away from sitting in an HQ in an office all day? What, why did you go for this mobile first approach?

A Yeah, you know, that's a part of it. Um, Um, a key insight that we had early on was that in order to be successful with salespeople, we can't just build and sell a piece of software. What we're bringing to the market is a lifestyle. It's an aspirational lifestyle that is more in keeping with what motivates the millennial salesperson. You know, there's this old perception of the coin operated salesperson is just motivated by money, but, but that couldn't be further from the further away from today's reality. Um, really it's, it's a fun, dynamic, enriching lifestyle that is the draw for somebody to choose sales as their career. And, and with millennials, lifestyle comes first. And so what we hear over and over again are, are things like, you know, what motivated me to become a salesperson was the idea of building relationships with the client, having a dynamic day to day that is not just spent in front of a computer, having my job be more seamlessly integrated into my lifestyle. And, and we realized that if we want to be successful, What we're doing is trying to enable that lifestyle of, you know, closing deals from the baseball game and becoming friends with the customer once the deal is done. And, and so we started out by thinking about that, and then we realized, well, obviously we have to build from home first, because we, we need to build a product that is, that is powerful …

AI assessment note: “trying to enable that lifestyle of, you know, closing deals from the baseball game”

Q Is there an enterprise company at the moment who you think has done really well at conveying this brand?

A Um, that's a good question. You know, um, there are certainly companies that, that are doing a really good job Compared to kind of what we're used to. You have, you have the slacks of the world, which, you know, um, the, the famous, we don't sell saddles, and, and is the, is the same, is the same kind of concept where, where Stuart was very clear about their selling a, a better way of lifestyle productivity, better way of living through your work rather than just a software product. Um, there's, there's companies like Greenhouse that, that comes to mind, the HR space that, Just a disaster of a space, um, where, where they came in with really elegant technology and, and messaging really directed at the end user who's going to end up spending time in the product. And so there are companies that are, that are certainly paying attention and doing a great job.

AI assessment note: “You have the slacks of the world... There's companies like Greenhouse that comes to mind”

Q And then finally, the next five years for you and immediately, what's in the product roadmap? What have we got ahead of us?

A Yeah, I, I would have a hard time answering the next five weeks question. Um, but, but no, to be, um, to be completely honest with you, you know, we, we think about the user, and so to us, the ultimate aim is if we can be the environment, um, through the preferred environment through which, uh, a business transaction happens. If, if we can create a, a suite of, of really intelligent tools that, that combine into ecosystem, um, Where a salesperson, and potentially even the customer, um, benefit from the technology really facilitating as good a transaction as possible, um, eliminate the information problem, and, and, and just bring sales and business transactions back to their fundamentals, which is really just a conversation where, where, you know, it's a craft of relationship making, and, and, and ultimately it should result in a mutually beneficial transaction. If we can really elegantly enable that with technology and, and bring it closer to its human fundament, um, then, then I think we will have succeeded.

AI assessment note: “I would have a hard time answering the next five weeks question.”

Q that you've got now. And so, I mean, A, you've got also quite a few people that we've had on the show. It seems we've had Dustin Dolganow, we've had, uh, Sami Akaji, um, Kate Shillow, but then we've also got Naval Ravikant, Ryan Holmes at Hootsuite, Jonathan Abrahams at Nuzzle. So, so how did you come to meet these kind of stellar investors? What was the story behind that?

A Yeah, you know, um, it's really a treat having, having all these guys on board. Silicon Valley is a, is a really small place, and, and to me, the rule of thumb of who I want on my cap table and, and how I think about meeting investors and bringing them on board is, do I, in my gut, feel like I can trust this person? Like, I can be vulnerable with them and, and admit making a mistake, and then I will be a better, stronger founder in person for having had that conversation with them. And, and I think that, um, for, for many of the investors anyway, that, that I, through kind of the evolution of immediately became introduced to, and who became excited enough to put in money and their time, um, that, that's very much also how they operate. Um, I, I can't generalize probably Silicon Valley, but, um, at least in my experience, what I've found is investment at the seed stage is an extremely personal process. It's a process of, is, is there that je ne sais quoi that makes me I want to spend more time with this person. Do I, do I feel more excited, more stimulated, more enriched? And do I feel like I can really trust this person at a profound level? And I think the smartest seed investors are investing in, in the founder's ability to use the seed capital to really figure out the answers to some really hard questions that have never previously been answered and make a lot of mistakes alo…

AI assessment note: “Silicon Valley is a, is a really small place, and, and to me”

Q that you've got now. And so, I mean, A, you've got also quite a few people that we've had on the show. It seems we've had Dustin Dolganow, we've had, uh, Sami Akaji, um, Kate Shillow, but then we've also got Naval Ravikant, Ryan Holmes at Hootsuite, Jonathan Abrahams at Nuzzle. So, so how did you come to meet these kind of stellar investors? What was the story behind that?

A Yeah, you know, um, it's really a treat having, having all these guys on board. Silicon Valley is a, is a really small place, and, and to me, the rule of thumb of who I want on my cap table and, and how I think about meeting investors and bringing them on board is, do I, in my gut, feel like I can trust this person? Like, I can be vulnerable with them and, and admit making a mistake, and then I will be a better, stronger founder in person for having had that conversation with them. And, and I think that, um, for, for many of the investors anyway, that, that I, through kind of the evolution of immediately became introduced to, and who became excited enough to put in money and their time, um, that, that's very much also how they operate. Um, I, I can't generalize probably Silicon Valley, but, um, at least in my experience, what I've found is investment at the seed stage is an extremely personal process. It's a process of, is, is there that je ne sais quoi that makes me I want to spend more time with this person. Do I, do I feel more excited, more stimulated, more enriched? And do I feel like I can really trust this person at a profound level? And I think the smartest seed investors are investing in, in the founder's ability to use the seed capital to really figure out the answers to some really hard questions that have never previously been answered and make a lot of mistakes alo…

AI assessment note: “Silicon Valley is a, is a really small place, and, and to me”