The Exchanges

Q I do want to ask that, you know, I joined my first board about a year ago. For you as a founder, I'd love to hear your advice. What could I do to be the best board member that I can be? And what advice would you give a newly minted board member on the other side of the table?

A I would give two pieces of advice. So, so the first one is, When the company is facing issue X, do not say, oh, I saw another company that had a similar issue, and they did Y. And the reason is, is that that is not contextualized to your company, your industry, the resources you have, the capabilities, your knowledge, and it's just flat out generally not helpful. What I think really good board members do is they have this big mental bank of all this learning and pattern recognition, but they contextualize it for your company and understanding what is really relevant to you. So that's the first thing. The second is, as a board member, when another board member says something, do not agree nor necessarily disagree, but try to point out either the other side of the probability distribution on what they're suggesting, because no matter what, there's no way that what they're saying is either without risk or without some opportunity cost. So I think if board members between each other can say, hey, I think that's a really interesting point, but what is the opportunity cost of focusing on that? Or if that ends up not being true, why might it not be true? And then you get diversity of thought around issues, and you leave the problem with the management team, but you open up their minds to different possibilities, and I think that makes some of the most productive input from board membe…

AI assessment note: “I would give two pieces of advice. So, so the first one is”

Q I do want to ask that, you know, I joined my first board about a year ago. For you as a founder, I'd love to hear your advice. What could I do to be the best board member that I can be? And what advice would you give a newly minted board member on the other side of the table?

A I would give two pieces of advice. So, so the first one is, When the company is facing issue X, do not say, oh, I saw another company that had a similar issue, and they did Y. And the reason is, is that that is not contextualized to your company, your industry, the resources you have, the capabilities, your knowledge, and it's just flat out generally not helpful. What I think really good board members do is they have this big mental bank of all this learning and pattern recognition, but they contextualize it for your company and understanding what is really relevant to you. So that's the first thing. The second is, as a board member, when another board member says something, do not agree nor necessarily disagree, but try to point out either the other side of the probability distribution on what they're suggesting, because no matter what, there's no way that what they're saying is either without risk or without some opportunity cost. So I think if board members between each other can say, hey, I think that's a really interesting point, but what is the opportunity cost of focusing on that? Or if that ends up not being true, why might it not be true? And then you get diversity of thought around issues, and you leave the problem with the management team, but you open up their minds to different possibilities, and I think that makes some of the most productive input from board membe…

AI assessment note: “I would give two pieces of advice. So, so the first one is”

Q My subsequent question is I agree in terms of the alignment to the mission and vision, but let's face it, when you're a company like And you're a hot company. Every investor will say, Jason, I'm totally aligned to your mission and vision. How do you truly determine whether someone is genuinely aligned? What questions do you ask?

A Well, it's actually the inverse. I watch what questions they ask. So the majority of folks expressed a lot of excitement about our business. So, you know, our retention, we have a 99% monthly retention of our users, our CAC to LTV ratios, all those things, our growth rate, And I noticed that the majority investors really focused the substantiative portion of their questions on those kinds of things. And it was the investors that also spent time trying to understand the benefit to consumers. And, you know, our mission is to make people less stressed and better off financially and really digging into how we're doing that and wanting to get validation on the fact that we were really aligned with our own mission and just not saying it. So it was actually the, the investors who were doing their own diligence to validate that. That I think it showed the difference between, you know, kind of people that were excited about the numbers versus people that were excited about the numbers and the impact we're trying to have in the world.

AI assessment note: “Well, it's actually the inverse. I watch what questions they ask.”

Q Can I ask, is it not important for the culture, for the morale, for the enthusiasm, excitement of the team to just feel like they're really on a moving ship, and having a celebration of that raise is part of it?

A So they're going to know that anyway, right? It's not like the team members aren't sharing the fundraising announcements with their friends. So it's more, you need to put it all in perspective. And it's not to say that, you know, nobody's allowed to celebrate, but we at Tally never have and never will explicitly have a celebration around the fundraise. It's always going to be around product and delivering value to consumers. And I just think it's important to train your team on what matters and what matters is delivering value. And that's where they should have that sense of this ship is moving. It's going somewhere. And I want them to have the connection to that, not to this kind of arbitrary stop at the gas station.

AI assessment note: “we at Tally never have and never will explicitly have a celebration around the fundraise”

Q I do want to kick off though, and, uh, it's really a question that I think about quite a lot, because I had Joe Fernandez on the show from Joy Mode, and he said that serial entrepreneurship is overrated. Now, I'm interested, as you said, you started numerous companies before Tally. Would you agree with him on this as a starting point? Let's start with that.

A So I, I respectfully disagree and disagree strongly. If that were true, then that also means that the, uh, 10,000 hour rule is a farce. This idea that when you focus on doing something really well for a long time, you get better at it. And I believe that when it comes to being a successful founder, success comes down to these brief moments of high leverage. And what I mean by that is that there's about a half a million minutes a year. And most of those minutes are either the monotony of going through work or you're sleeping. But in a given year, there's a couple brief moments that really, really matter. And these are the moments where you're sitting in front of a Potential candidate for some executive role and they're way outside your league, but you're able to connect with them on a certain level and inspire them to quit their ridiculously overpaid job to take all this risk and a lower salary to work for you. Or, you know, you bump into that investor in an elevator and you have the instincts to capitalize on that and turn that into a meeting. So what I believe first time founders really struggle with is sifting between, let's say that the half a million minutes that don't matter and the 10 that do in the year, and that 10,000 hours or 20,000 hours of practice of doing it over and over really gives you that intuition on identifying what moments matter, and then making sure that…

AI assessment note: “So I, I respectfully disagree and disagree strongly.”

Q And in terms of kind of companies before that, I've been informed very wisely by, by Nikhil at Shasta and Sean at Shasta that this wasn't your first company with your co-founder Jasper. So a question from them, and it's, what's changed this time around with Tally that you maybe were not doing last time that you are doing this time and vice versa?

A Well, there's, there's probably a lot. I feel like you, you learned so much, but If I were to zero in on the, on the biggest thing, it's actually around recruiting. You know, assuming that you have a good market and a great idea, I believe that the number one lever you have to succeed is recruiting, meaning the quality of the people that you have on the team, how passionate they are about what you're doing, and their willingness to stay with you through thick and thin. And the main areas that I've done differently, I've kind of broken down into three Three parts. So the first is to never settle at my last company. I hired some really good people, but there were many times where I felt like this is a good person, but there's probably a better person out there, but we've got to move fast and get stuff done. So let's just hire him now. Now a tally, I pledge to myself to never, ever settle. So in order to keep myself honest on that, what I define as the bar of somebody I want to hire is somebody that I fall in love with. So obviously not romantic way, but When I think about the candidate and if I think about them saying no to me and I get really sad and feel like I might need to go home and drink a couple extra beers or something, I know I've got a good candidate and that that's somebody I should hire. If I don't have that kind of feeling of remorse, if they were to say no, then I …

AI assessment note: “If I were to zero in on the, on the biggest thing, it's actually around recruiting.”

Q Can I ask, when you look back at the kind of incredible experiences you've had fundraising with the likes of Cowboy, Shasta, Kleiner, some of the top funds of the day, so talk to me, what advice would you have for startups in the fundraising process that you've kind of garnered from your success in the raises?

A Yeah. So, so I think it depends on which stage they are in raising. Okay. And in the seed round, not to say it's easy to raise a seed round, but folks are willing to take a lot more, but just, they're just willing to take more risk, right? So if you have a good story and it seems like you're, you have a good idea in a good market, it's possible to get funded. I think series A gets, it gets a little more difficult because you now are putting some serious dollars to work And you haven't really proven that much more compared to, to the seed round to raise a series a, I think it all comes down to having a perfectly curated story where, you know, exactly what are the underlying assumptions that will make or break this and being really transparent about it. When we raised our series a for my last company and client air funded us, the entire pitch was I walked in, I put it on a whiteboard, five assumptions. I said, These are the five assumptions you have to a hundred percent believe in in order for this to be an interesting deal. Are there any items on this list that no matter how much we talk about, you're not going to, you're not going to be able to get on board. Okay, cool. Which ones do you already believe in? Okay. Let's cross those off the list. All right. Now let's spend the next hour on these three assumptions and figure out if you can get comfortable with those. And so I thin…

AI assessment note: “being more open and transparent and less defensive about it”

Q And in terms of kind of companies before that, I've been informed very wisely by, by Nikhil at Shasta and Sean at Shasta that this wasn't your first company with your co-founder Jasper. So a question from them, and it's, what's changed this time around with Tally that you maybe were not doing last time that you are doing this time and vice versa?

A Well, there's, there's probably a lot. I feel like you, you learned so much, but If I were to zero in on the, on the biggest thing, it's actually around recruiting. You know, assuming that you have a good market and a great idea, I believe that the number one lever you have to succeed is recruiting, meaning the quality of the people that you have on the team, how passionate they are about what you're doing, and their willingness to stay with you through thick and thin. And the main areas that I've done differently, I've kind of broken down into three Three parts. So the first is to never settle at my last company. I hired some really good people, but there were many times where I felt like this is a good person, but there's probably a better person out there, but we've got to move fast and get stuff done. So let's just hire him now. Now a tally, I pledge to myself to never, ever settle. So in order to keep myself honest on that, what I define as the bar of somebody I want to hire is somebody that I fall in love with. So obviously not romantic way, but When I think about the candidate and if I think about them saying no to me and I get really sad and feel like I might need to go home and drink a couple extra beers or something, I know I've got a good candidate and that that's somebody I should hire. If I don't have that kind of feeling of remorse, if they were to say no, then I …

AI assessment note: “If I were to zero in on the, on the biggest thing, it's actually around recruiting.”

Q Can I ask, when you look back at the kind of incredible experiences you've had fundraising with the likes of Cowboy, Shasta, Kleiner, some of the top funds of the day, so talk to me, what advice would you have for startups in the fundraising process that you've kind of garnered from your success in the raises?

A Yeah. So, so I think it depends on which stage they are in raising. Okay. And in the seed round, not to say it's easy to raise a seed round, but folks are willing to take a lot more, but just, they're just willing to take more risk, right? So if you have a good story and it seems like you're, you have a good idea in a good market, it's possible to get funded. I think series A gets, it gets a little more difficult because you now are putting some serious dollars to work And you haven't really proven that much more compared to, to the seed round to raise a series a, I think it all comes down to having a perfectly curated story where, you know, exactly what are the underlying assumptions that will make or break this and being really transparent about it. When we raised our series a for my last company and client air funded us, the entire pitch was I walked in, I put it on a whiteboard, five assumptions. I said, These are the five assumptions you have to a hundred percent believe in in order for this to be an interesting deal. Are there any items on this list that no matter how much we talk about, you're not going to, you're not going to be able to get on board. Okay, cool. Which ones do you already believe in? Okay. Let's cross those off the list. All right. Now let's spend the next hour on these three assumptions and figure out if you can get comfortable with those. And so I thin…

AI assessment note: “I think it all comes down to having a perfectly curated story”

Q Can I ask, is it not important for the culture, for the morale, for the enthusiasm, excitement of the team to just feel like they're really on a moving ship, and having a celebration of that raise is part of it?

A So they're going to know that anyway, right? It's not like the team members aren't sharing the fundraising announcements with their friends. So it's more, you need to put it all in perspective. And it's not to say that, you know, nobody's allowed to celebrate, but we at Tally never have and never will explicitly have a celebration around the fundraise. It's always going to be around product and delivering value to consumers. And I just think it's important to train your team on what matters and what matters is delivering value. And that's where they should have that sense of this ship is moving. It's going somewhere. And I want them to have the connection to that, not to this kind of arbitrary stop at the gas station.

AI assessment note: “we at Tally never have and never will explicitly have a celebration around the fundraise”

Q Final question for the quickfire, though, and it's like, I totally agree with you in terms of the need to create that safe space and the benefits of doing so, but what can one actually tangibly do to create the safe space itself?

A So how about I'll tell you concretely with Tally. So we have three core values and I'll talk about the one that's closest to my heart. So the wording is change shoes often. And the underlying idea behind that is empathy. And we were really inspired by the walk a mile in somebody else's shoes. So it's valuing that just the act of taking the time to imagine what it's like to be another person, both emotionally and intellectually, and really approaching them with curiosity and Such that you're actually interested in understanding that perspective, not making judgments about what they have to share. And I think that's one very concrete way that you can create inclusion is through the behaviors that create closeness and kind of status, if you will, within your company.

AI assessment note: “wording is change shoes often. And the underlying idea behind that is empathy”

Q we sign the term sheet and we're in business. Now, many people celebrate this big moment for the milestone of the company. In terms of celebrating fundraising, you said before, raising money is not something to be celebrated, especially if your round is overinflated. So interesting. I think I'd probably have a different viewpoint. So let's break the sentence in two. Why is it wrong to celebrate raising money, Jason?

A Well, so every round that we've raised, I've done a talk with a team. I use a metaphor and it's, it's the, uh, the road trip metaphor. So imagine you're on a road trip, maybe with some friends or family going from San Francisco to New York. And you know, there's going to be some fun, there's going to be some monotony, but like in general, it's about this journey. But in order to get from one coast to the next, you definitely need gas to put in your car. And so that to me is what fundraising is, is you're on this journey and you need to refuel and clearly you need capital to do that. But in and of itself, putting gas in the car is not this big thing to celebrate. It's something to be appreciative of, but what we should celebrate as founders and as teams is Is shipping product, delivering customer value, and especially if, let's say, you've raised a big round that's maybe ahead of where your business results are, all the more you should not celebrate because you should understand the gravity of what you've signed up for, which is, is you signed up to deliver even more value than maybe you are thinking you needed to provide in order to give good returns to shareholders. So I just prefer to have all my team grounded and understanding that with that fundraising connection, It becomes a big mountain to climb, and quite honestly, a duty to deliver on the promises that were made when f…

AI assessment note: “putting gas in the car is not this big thing to celebrate.”

Q I do want to kick off though, and, uh, it's really a question that I think about quite a lot, because I had Joe Fernandez on the show from Joy Mode, and he said that serial entrepreneurship is overrated. Now, I'm interested, as you said, you started numerous companies before Tally. Would you agree with him on this as a starting point? Let's start with that.

A So I, I respectfully disagree and disagree strongly. If that were true, then that also means that the, uh, 10,000 hour rule is a farce. This idea that when you focus on doing something really well for a long time, you get better at it. And I believe that when it comes to being a successful founder, success comes down to these brief moments of high leverage. And what I mean by that is that there's about a half a million minutes a year. And most of those minutes are either the monotony of going through work or you're sleeping. But in a given year, there's a couple brief moments that really, really matter. And these are the moments where you're sitting in front of a Potential candidate for some executive role and they're way outside your league, but you're able to connect with them on a certain level and inspire them to quit their ridiculously overpaid job to take all this risk and a lower salary to work for you. Or, you know, you bump into that investor in an elevator and you have the instincts to capitalize on that and turn that into a meeting. So what I believe first time founders really struggle with is sifting between, let's say that the half a million minutes that don't matter and the 10 that do in the year, and that 10,000 hours or 20,000 hours of practice of doing it over and over really gives you that intuition on identifying what moments matter, and then making sure that…

AI assessment note: “So I, I respectfully disagree and disagree strongly.”

Q You mentioned the word value there, and it's interesting because, you know, now we have the investors on board. A lot of investors claim to add a ton of value to the company as part of their check. I'm interested, having done four hours of funding with Tally and prior companies, what value have you found that VCs bring first?

A You know, I'm a little pessimistic on this one. My starting point is you have to have the mindset that VCs are going to provide no value. They will all go on and on about the value they'll provide, but What you're shooting for as a base starting point is zero value. And what you're trying to avoid is negative value. And negative value comes in distractions and potentially bad advice and steering you the wrong way. So really the battle is to make sure that they're not going to actually hurt the company. But once you're at a point of, okay, I'm confident that we're at least at a place of neutral, then it's really up to the CEO to say, okay, investor A, I'm going to give you a specific job and a specific mission. And this is what I need you to focus on. And here are the X Expectations and the timelines, almost like you would an employee where there's a clearly defined task that they can own and own entirely. So maybe you've heard the term DRI or just directly responsible individuals. Make sure that there's nothing that is held by the group. There has to be one individual who owns every item, and that way, investors who are busy can say, okay, cool, I've got this one task, and I know that other investors are handling other tasks, and you can really hold them accountable for working on those projects, and then you're in a position to move from neutral to value-add.

AI assessment note: “you have to have the mindset that VCs are going to provide no value.”

Q your investors before the show. As I said, huge fan of all of them. I absolutely love the camp table that you have in place. In terms of the relationship build with them, given the fact that, you know, you do want to be heads down on the company, how do you think about the relationship build process with the investors and just really building that human non-transactional caring relationship?

A So I think it starts early. So half of my investors, I've raised four rounds of funding, and the leads, two of them I knew beforehand, and those relationships were years old, and then two of them were new. And so I think focusing on the new relationships in the early times when you're trying to figure out, hey, do you want to take money from this person and work with them? I actually really enjoy walks. I think it's a great opportunity just to get out, spend a couple hours walking around. And what I'm looking for Is I'm trying to get to the bottom of their motivations. What really makes them happy? What's their, what's their view of self-actualization? Is it status? Is it wealth? Or is it more making an impact and leaving something meaningful behind them? And it's the folks that are more intrinsically motivated by those things outside of superficiality that I'm drawn to. Cause I believe that when you're in, let's just say a spot of bother in the company at some point, those that are worried about their reputation or how much money they're going to make, Are going to potentially be drawn to suboptimal decisions as it relates to the company and the mission, and those that are more grounded in their identity and what motivates them are going to be more likely to, you know, really align with what we're trying to do.

AI assessment note: “trying to get to the bottom of their motivations”

Q your investors before the show. As I said, huge fan of all of them. I absolutely love the camp table that you have in place. In terms of the relationship build with them, given the fact that, you know, you do want to be heads down on the company, how do you think about the relationship build process with the investors and just really building that human non-transactional caring relationship?

A So I think it starts early. So half of my investors, I've raised four rounds of funding, and the leads, two of them I knew beforehand, and those relationships were years old, and then two of them were new. And so I think focusing on the new relationships in the early times when you're trying to figure out, hey, do you want to take money from this person and work with them? I actually really enjoy walks. I think it's a great opportunity just to get out, spend a couple hours walking around. And what I'm looking for Is I'm trying to get to the bottom of their motivations. What really makes them happy? What's their, what's their view of self-actualization? Is it status? Is it wealth? Or is it more making an impact and leaving something meaningful behind them? And it's the folks that are more intrinsically motivated by those things outside of superficiality that I'm drawn to. Cause I believe that when you're in, let's just say a spot of bother in the company at some point, those that are worried about their reputation or how much money they're going to make, Are going to potentially be drawn to suboptimal decisions as it relates to the company and the mission, and those that are more grounded in their identity and what motivates them are going to be more likely to, you know, really align with what we're trying to do.

AI assessment note: “I actually really enjoy walks. I think it's a great opportunity just to get out”

Q say that VCs are today's brilliant marketers, so absolutely. I do want to ask you, because we spoke about some of your investors before, and you have an amazing board in place with Mamoon, with Eileen, with Angela, obviously my favorite, Nikhil, sorry to everyone else, and I spoke to all of them before the show, and Mamoon asked, how do you run your board meetings first? Let's start there.

A Well, it actually begins way before the board meeting, so I do an orientation for new board members, and this is a structured onboarding where I make sure that they understand the tally strategy and our values and the norms that are expected in a board meeting. And I really try to bring a lot of intensity and intention to the board meeting. And the way that I encourage that is I'm pretty hardcore about making sure that nobody's on any devices or distracted during the meeting. And inevitably that will come up. And I have a conversation with a, with a board member afterwards and just really make sure that they know that when we're together, focusing on tally for that two or three hours, that we're at Attentive and more focused. And one thing to do is maybe provide a couple more breaks throughout the meeting so that people can step out and do their emails. Another thing that I find is that every single board meeting, I'm learning something and it's new and it's hard and actually formally ending the board meeting. And that's actually important because you don't want to leave the board room as the CEO without formally ending the board meeting. Cause in a really adverse scenario, if the board meeting is still running, things could happen that you wouldn't want. So you formally end the board meeting, but then give the invest There's an opportunity to talk amongst themselves and then c…

AI assessment note: “nobody's on any devices or distracted during the meeting”

Q Final question for the quickfire, though, and it's like, I totally agree with you in terms of the need to create that safe space and the benefits of doing so, but what can one actually tangibly do to create the safe space itself?

A So how about I'll tell you concretely with Tally. So we have three core values and I'll talk about the one that's closest to my heart. So the wording is change shoes often. And the underlying idea behind that is empathy. And we were really inspired by the walk a mile in somebody else's shoes. So it's valuing that just the act of taking the time to imagine what it's like to be another person, both emotionally and intellectually, and really approaching them with curiosity and Such that you're actually interested in understanding that perspective, not making judgments about what they have to share. And I think that's one very concrete way that you can create inclusion is through the behaviors that create closeness and kind of status, if you will, within your company.

AI assessment note: “wording is change shoes often. And the underlying idea behind that is empathy.”

Q we sign the term sheet and we're in business. Now, many people celebrate this big moment for the milestone of the company. In terms of celebrating fundraising, you said before, raising money is not something to be celebrated, especially if your round is overinflated. So interesting. I think I'd probably have a different viewpoint. So let's break the sentence in two. Why is it wrong to celebrate raising money, Jason?

A Well, so every round that we've raised, I've done a talk with a team. I use a metaphor and it's, it's the, uh, the road trip metaphor. So imagine you're on a road trip, maybe with some friends or family going from San Francisco to New York. And you know, there's going to be some fun, there's going to be some monotony, but like in general, it's about this journey. But in order to get from one coast to the next, you definitely need gas to put in your car. And so that to me is what fundraising is, is you're on this journey and you need to refuel and clearly you need capital to do that. But in and of itself, putting gas in the car is not this big thing to celebrate. It's something to be appreciative of, but what we should celebrate as founders and as teams is Is shipping product, delivering customer value, and especially if, let's say, you've raised a big round that's maybe ahead of where your business results are, all the more you should not celebrate because you should understand the gravity of what you've signed up for, which is, is you signed up to deliver even more value than maybe you are thinking you needed to provide in order to give good returns to shareholders. So I just prefer to have all my team grounded and understanding that with that fundraising connection, It becomes a big mountain to climb, and quite honestly, a duty to deliver on the promises that were made when f…

AI assessment note: “putting gas in the car is not this big thing to celebrate”

Q And then what would you most like to see change in the world of fintech?

A So I'm going to be selfish on this. The OCC is contemplating issuing something called a special purpose fintech charter. And it's kind of like the unbundling of the bank, right? If you think about a bank is it takes deposits and moves money and it lends money. Let's just say those three things. So what they're contemplating is doing a banking charter that would let you just do one out of those three, and then not have to comply with the regulation for the other things you're not doing. So you'd still have to comply a hundred percent with the regulations related to what you're doing, but if you do want to take deposits, which is the most onerous, then you could have a bank charter light and not have to worry about that. And that would be huge for us, and it would also be big for a lot of other startups.

AI assessment note: “The OCC is contemplating issuing something called a special purpose fintech charter.”

Q You said there about, um, leaning into the regulators, uh, and it takes me back, I, I told you, I'm, I do my diligence, because you've also said that a brilliant management concept from 2016 is radical candor. So kind of with that How do you approach radical candor and its implementation within startups more broadly?

A Yeah, so maybe for those listeners who don't know about radical candor, it's this framework developed by Kim Scott. She was at Google running AdWords, and the idea, it's very simple, is that you should both care personally about the people on your team and challenge them directly, and the heart of radical candor is actually trying to get your team to And everybody who works from you, any level below you to feel comfortable being radically candid with you as the CEO. So that's the biggest challenge. It's obviously easy for a CEO to be radically candid with a janitor or something like that, but for it to go the other way around is a big challenge. So we worked actually with him and she helped us do a bunch of exercises internally with our team to get them comfortable being very direct and challenging directly up to Japs Jasper and myself, Jasper is my co-founder. And anytime that happens, you have to, as the CEO, you have to praise that person. So I've received some pretty harsh feedback from different people on my team. And there was a specific instance where this is a little silly, but I got up on my high horse and I told everybody after we raised the series a, how we weren't going to buy a bunch of snacks, like all the other startups, how we're going to be really tight with our Don't start asking for snacks.

AI assessment note: “she helped us do a bunch of exercises internally with our team”

Q say that VCs are today's brilliant marketers, so absolutely. I do want to ask you, because we spoke about some of your investors before, and you have an amazing board in place with Mamoon, with Eileen, with Angela, obviously my favorite, Nikhil, sorry to everyone else, and I spoke to all of them before the show, and Mamoon asked, how do you run your board meetings first? Let's start there.

A Well, it actually begins way before the board meeting, so I do an orientation for new board members, and this is a structured onboarding where I make sure that they understand the tally strategy and our values and the norms that are expected in a board meeting. And I really try to bring a lot of intensity and intention to the board meeting. And the way that I encourage that is I'm pretty hardcore about making sure that nobody's on any devices or distracted during the meeting. And inevitably that will come up. And I have a conversation with a, with a board member afterwards and just really make sure that they know that when we're together, focusing on tally for that two or three hours, that we're at Attentive and more focused. And one thing to do is maybe provide a couple more breaks throughout the meeting so that people can step out and do their emails. Another thing that I find is that every single board meeting, I'm learning something and it's new and it's hard and actually formally ending the board meeting. And that's actually important because you don't want to leave the board room as the CEO without formally ending the board meeting. Cause in a really adverse scenario, if the board meeting is still running, things could happen that you wouldn't want. So you formally end the board meeting, but then give the invest There's an opportunity to talk amongst themselves and then c…

AI assessment note: “it actually begins way before the board meeting, so I do an orientation”

Q the walk, and it kind of goes back to that human centricity, but the big concern for me right now is with the proliferation of capital in the ecosystem, we're seeing such compression on fundraising timelines, meaning that you maybe just don't get to know this In this period of shortened time, how do you think about the compression of fundraising timelines? And are you as concerned as I am?

A I mean, I think maybe one of the implications there is around valuation. So even with short timelines, you can still get walks. So our rounds went very, very fast, but walks were still had. So I think, I think there's still, still time for a couple hours, uh, stolen through the Presidio. But I think maybe your, your implied question is, am I worried about, about venture valuations? And I actually think this is more structural. To the world economy at this point, because more and more wealth is being concentrated in the top five, one percent, and those individuals tend to save and invest most of their money. So what that means is there's a growing glut of capital looking for returns, but with overall GDP of most nations being pretty low, that means that there's a relatively low supply of yielding investments. And what that translates to is that Founders that have identified great markets and great opportunities and are executing are a very scarce resource. And so that the overall supply is much lower than the demand and therefore the price rises. So I would actually argue that given those constraints, venture funded companies aren't as overpriced as you might think.

AI assessment note: “even with short timelines, you can still get walks. So our rounds went very, very fast”

Q You said there about, um, leaning into the regulators, uh, and it takes me back, I, I told you, I'm, I do my diligence, because you've also said that a brilliant management concept from 2016 is radical candor. So kind of with that How do you approach radical candor and its implementation within startups more broadly?

A Yeah, so maybe for those listeners who don't know about radical candor, it's this framework developed by Kim Scott. She was at Google running AdWords, and the idea, it's very simple, is that you should both care personally about the people on your team and challenge them directly, and the heart of radical candor is actually trying to get your team to And everybody who works from you, any level below you to feel comfortable being radically candid with you as the CEO. So that's the biggest challenge. It's obviously easy for a CEO to be radically candid with a janitor or something like that, but for it to go the other way around is a big challenge. So we worked actually with him and she helped us do a bunch of exercises internally with our team to get them comfortable being very direct and challenging directly up to Japs Jasper and myself, Jasper is my co-founder. And anytime that happens, you have to, as the CEO, you have to praise that person. So I've received some pretty harsh feedback from different people on my team. And there was a specific instance where this is a little silly, but I got up on my high horse and I told everybody after we raised the series a, how we weren't going to buy a bunch of snacks, like all the other startups, how we're going to be really tight with our Don't start asking for snacks.

AI assessment note: “she helped us do a bunch of exercises internally with our team”

Q On the converse, then, if that's kind of where investors potentially add neutral or slight positive value, on the converse, where do you think there's common conceptions that VCs add value by probably first-time founders who haven't raised and haven't worked with VCs before, where they think there's a ton of value coming, where maybe there isn't, actually?

A So I think the challenge of being in venture capital is that outside of the actual partner who's doing the investing, money is a complete commodity, and so the drive is to try to differentiate An undifferentiatable commodity through the quote unquote value add. So I think it's more of marketing and what venture investors have to do to try to get entrepreneurs to see them as somehow a more valuable source of capital. And clearly there's, there's a big difference between one investor and the next, but oftentimes that is represented in the partner and their expertise and who they are as a human. And it ends up really being differentiated on the person and less so on the overall firm.

AI assessment note: “it's more of marketing and what venture investors have to do”

Q On the converse, then, if that's kind of where investors potentially add neutral or slight positive value, on the converse, where do you think there's common conceptions that VCs add value by probably first-time founders who haven't raised and haven't worked with VCs before, where they think there's a ton of value coming, where maybe there isn't, actually?

A So I think the challenge of being in venture capital is that outside of the actual partner who's doing the investing, money is a complete commodity, and so the drive is to try to differentiate An undifferentiatable commodity through the quote unquote value add. So I think it's more of marketing and what venture investors have to do to try to get entrepreneurs to see them as somehow a more valuable source of capital. And clearly there's, there's a big difference between one investor and the next, but oftentimes that is represented in the partner and their expertise and who they are as a human. And it ends up really being differentiated on the person and less so on the overall firm.

AI assessment note: “the drive is to try to differentiate An undifferentiatable commodity through the quote unquote value add”

Q the walk, and it kind of goes back to that human centricity, but the big concern for me right now is with the proliferation of capital in the ecosystem, we're seeing such compression on fundraising timelines, meaning that you maybe just don't get to know this In this period of shortened time, how do you think about the compression of fundraising timelines? And are you as concerned as I am?

A I mean, I think maybe one of the implications there is around valuation. So even with short timelines, you can still get walks. So our rounds went very, very fast, but walks were still had. So I think, I think there's still, still time for a couple hours, uh, stolen through the Presidio. But I think maybe your, your implied question is, am I worried about, about venture valuations? And I actually think this is more structural. To the world economy at this point, because more and more wealth is being concentrated in the top five, one percent, and those individuals tend to save and invest most of their money. So what that means is there's a growing glut of capital looking for returns, but with overall GDP of most nations being pretty low, that means that there's a relatively low supply of yielding investments. And what that translates to is that Founders that have identified great markets and great opportunities and are executing are a very scarce resource. And so that the overall supply is much lower than the demand and therefore the price rises. So I would actually argue that given those constraints, venture funded companies aren't as overpriced as you might think.

AI assessment note: “I think maybe your, your implied question is, am I worried about, about venture valuations?”

Q And then talk to me, Jason. Next five years for you and for Tally, what's the roadmap ahead?

A Roadmap ahead. So ultimately what we're building is something to automate your financial life. Five years from now, I really hope that I can pile into a car and have it drive me and my family up to Tahoe, and I don't have to do anything. One way or another, computers are going to be doing a lot of things for us, and the other thing that they're going to be doing is they're going to be like a personal accountant who takes work off of your plate and actually does things for you. In the past, finance apps give you charts and data, and you have to do all the work. In the future, Tally is actually going to be doing those things for you, so you don't even have to worry about it. So we're working very hard to find lots of ways to automate your financial life, so you don't even have to think about it.

AI assessment note: “In the future, Tally is actually going to be doing those things for you”