ANGELA STRANGE: Hey, good afternoon. All right, show of hands how many founders in the audience?

Oh, wow. All right, how many working at a Series, ABC company? Okay, this topic, Making Tough Decisions, is relevant to the entire room, unsurprisingly. And I think what’s particularly interesting here is there’s a lot of content about how startups are hard. And they’re generally told by very rich founders that have made their money and are now sitting on a beach. It’s pretty rare that you get this kind of candor from founders that are in the middle of going through the journey. I’m Angela Strange, General Partner at Andreessen Horowitz and I’m very lucky that we have two CEOs that have agreed to be very open about some challenges that they most recently went through. So we will start with Yin Wu, CEO of Pulley.

YIN WU: I’m Yin, I’m the founder of Pulley, and we help companies manage their cap table and their equity. So if any of you guys are founders when you’re hiring, when you’re fundraising, when you’re hiring employees, we think equity is one of the lifebloods of the company. It’s what accrues value and could be the most valuable asset that your company has if it really becomes successful.

ANGELA STRANGE: Awesome. So we got the chance to sit and have coffee a few days ago. And prior, I looked you up on LinkedIn and I was looking for the CEO of Pulley and I couldn’t find the CEO of Pulley. I could find Customer Success at Pulley, which is your official title on LinkedIn. Maybe start with the why behind that.

YIN WU: Yeah, I think that’s actually an upgrade because the first title I had on LinkedIn was janitor. Because I feel like, especially if you’re a founder, you do everything at the company that’s not getting done. So it doesn’t matter in many ways what your title was. And the reason I ended up changing it to Customer Success is I wanted it to be a sign for everyone at the company that ultimately what makes Pulley successful is if our customers are successful. I think about why I even started Pulley in the first place was I think that founders need more leverage when it comes to growing and scaling their companies. And for us, if the founders at our platform can do better, then they can do better. Today, Pulley works a lot with startups. So as we continue to scale and work with later stage companies, I think it’s the case that being able to serve them and their customer also continues, I think, to be really critical.

ANGELA STRANGE: All right, so we’re going to start with a topic that came up in the last panel, which is culture which is a notoriously ill-defined, but very important concept. And I think this is particularly important to talk with you because Pulley was your third company and you were very intentional actually when you started by hiring former founders. So maybe start with like, how did you think about culture? What was the culture you had when you started?

YIN WU: Yeah, it’s maybe just like going back to what you’re talking about with the title. It’s funny in the customer success because I think that’s one of those things and the way it ties back into culture is really the intentionality and the condition that you have. The people that have brought up my title the most are investors. When we’re going out to fundraisers saying like, “Hey, you may need to change this because, especially if you are a female founder going out to a fundraiser like saying you’re customer success doesn’t give the right tone.” But the people that really resonate with the title and then come up to me and say, “Hey, you’re customer success? I know what that feels like because I am in the thick of it for my own company.”

We have a very opinionated stance on culture at Pulley. And one of the more controversial things that I had tweeted when Pulley was just getting started was this idea that we are not a family.

We are a high-performance sports team. The reason we want to operate like a sports team instead of a family is I have a family; they’re great. If your partner makes you a meal and it’s not amazing, you’re not giving them 10 pointers on what can you do next time in order to really knock it out of the park. You’re probably just grateful that there’s food on the table. But if you think about as a company, there’s a goal, there’s a championship that you want to go and win. If you’re not honest about what’s working and what’s not working, then you can’t hit those goals. When we initially sent this out, I think there was an error within the valley of you really do want to be something for everyone. But with a startup, you’re not 50,000 people, trying to be something for everyone actually dilutes the culture that you can have.

ANGELA STRANGE: I bet your investors definitely push back on that title. But I think it’s shown that it resonates with customers, which is more important. So talk about, you’re telling me a story about how you hired initially former founders, right? And there’s a large sort of understanding that they can be great employees. What was the culture that you had at the start of Pulley?

YIN WU: Yeah, I think that the culture that you have with Pulley also is something that evolves. So when Pulley was around 10 people, this was the time that I tweeted it. It was 70% of our team was former founders. Great also from a marketing perspective. So 7 out of 10 had started a company in the past and were excited to join Pulley because of our mission of building for founders. While that still is partly true where we do want to bring founders on board, the type of folks we hire to the team I think has also evolved. One of the things that we’ve realized, I think as Pulley has continued to grow is that we also partly along the way, even though we had a really strong stance in what we saw the culture needed to be, I think the lost sight of that. And it was one of those days where my cofounder and I were looking at each other and Stripe, I think in the early days had this thing called the airport test.

If you saw one of your coworkers at an airport, would you want to go and sit next to them? Even if they were so strong technically, would you want to just go and sit next to a person? And it was a case for us that we realized, man, there’s so many people on the team we don’t know if we would actually want to go and sit next to them. And the specifics of how that happens is you may go and hire executives or managers that aren’t a great fit. And then they build teams that end up not being a great fit for the culture and then it propagates to the rest. And what we ended up doing was actually doing a pretty significant reset of the company and then we needed to figure out how to actually go and operationalize the culture that we wanted.

ANGELA STRANGE: And by reset, you mean...

YIN WU: I mean, we did a layoff of over 30% of the team. I think it was probably one of the hardest days within the company, but we did this at a time where we had actually just fundraised. So going back to the relationship with your investor, we’re fortunate to have had really supportive investors. But there was a bit of “Wait, why are you doing this? You’re not about to run out of money. You guys are actually doing fine. Why are you doing this reset?” Because we didn’t think that we actually had the team that we needed to be able to be successful for that next round.

ANGELA STRANGE: And then I think one of the things that we talked about that would be helpful is “Okay, we know what culture we want, but then how do we actually operationalize that?” And I think adding an interview question that says “Do you want to sit with them at the airport?” is nice, but probably not quite enough.

YIN WU: Yeah, so we sat down and there is 10 cultural values within Pulley. And again, these are our values. They’re not right or wrong but these are the values that we believe are important for the company.

ANGELA STRANGE: And how did you come up with those?

YIN WU: So one of our values is conviction, not consensus. So not be at consensus. Because at the end of the day, I think the founder of the company is the lifeblood of the company. And I think being a founder is also so different than being an executive. If you look at an executive’s career path, you can be a VP of Eng at company A then you’ll be VP of Eng at company B. But if you’re a founder and you’re really successful and you decide to start another company, guess what? You’re starting at the bottom again. You’re choosing to be an intern again.

And I think it’s so rare to have people with a mindset of, “I’m going to risk it all again because there’s this mission that I wanted to bring into this world.”

How many of you guys were at the Jensen Huang talk yesterday? I thought that was one of the best conversations that you have, where you look at Jensen and his bid on how it took 10 years of R&D and billions in investment to build the chip that they have today was mind-blowing because I think that’s not a bet that most executives would go and take.

So when we think about building the culture at Pulley, we came with these values because these are values that me and my cofounders believe were really important. The way that we thought about operationalizing it was, here’s a list of the values, and for each of these values we had a set of questions that we wanted to ask candidates and to see how they would respond. And we were opinionated on what would be a good response and what would also be a bad response. So, as an example, one of the questions that we sometimes ask folks on the HR team is “What do you think is more important: the company goals or the employee experience?”

It’s a question that you may be surprised by what folks say for the response but we know what kind of response we actually do want to hear. We know what is important when you’re a 50-person company fighting to survive, fighting to grow because the default stats is the company is not going to make it. You want to SWAT team of the folks that really believe it actually can be possible.

ANGELA STRANGE: And now, had you come up with these 10 cultural criteria right at the start and you just hadn’t operationalized, or was that something you came up with later and then operationalized it?

YIN WU: So we came up with some of these values but they were also tweaked over time. So like one that we ended up changing was when Pulley was just really early we really liked this idea of speed, just move quickly, go, go, go. Because I think speed is one of the biggest advantages you have as a smaller company versus a larger org where there’s just so much that you need to move in order to push anything forward.

But what we realized like even at the stage that we’re in now, speed wasn’t the core value for us because we don’t want to move quickly in all directions. So now that value has tweaked into momentum over speed. You want to build momentum.

So one of the things that we do on our team is that we often say that instead of using the rocket ship emoji to say like LFG because when a rocket ship runs out of fuel it just crashes back to earth. I think there’s a lot of companies if you look at back in the 2021 era, where you can almost guarantee your next round where funding was nearly free, where interest rates were near zero that you could just always get more fuel. But what you didn’t get was to build a sustainable business on the other end. So the steam engine emoji is that you can build momentum and what happens when you run out of fuel? Well, you can actually keep going. I think that is what we actually want to do within Pulley.

ANGELA STRANGE: Super helpful. Last point on this one, one more question I think that you talked about was “Tell me about a time when the team has not picked your idea.”

YIN WU: Oh, yeah.

ANGELA STRANGE: You want to talk about that?

YIN WU: One of the questions that we ask is “Tell me about a time when the team didn’t pick your idea and why that was good.” It’s always surprising to me. First of all, a lot of candidates think it’s a trick question. It was like, why are you telling me that? It’s asking me about when I was wrong during an interview. But we promise it’s not actually a trick question because there’s no chance that myself, anyone on the leadership team or anyone within the company is always 100% correct. If you’re 100% correct, you’re not taking enough shots.

So we want to see what people are saying for like, are you self-aware of when you were wrong? And so many times, candidates actually come back and say, “They didn’t go with my idea but then don’t worry, a month later, I was still correct.” Or “They didn’t go with my idea but you know what, if we just kept trying, it was it.” And so this is what I think about when it comes to aligning the questions that you want to ask to be able to probe for like hey, based on this background is this person actually a great fit for you and your team? And I think really sticking to it.

ANGELA STRANGE: Yeah, I love... I think you just have such a simple yet powerful framework for culture which is: decide on your values, what are the questions that test for that? And it’s a great way to scale and have that conversation in a much more specific way.

YIN WU: I think the hard part is hiring is really tough. I think because what you’re asking someone to do is “Hey, do you want to come and join my startup where there’s no guarantee of success and you’re going to make a lot less money than what you’re making today?” And you want them to say yes. So then the hard part is many times I think the team is often pushed for like “This person is so great technically. This person is such an amazing salesperson, just look at their numbers.” But then for us, we stick to it. If they don’t pass the culture interview, it’s still a no. And I think that’s part of maybe momentum versus speed.

ANGELA STRANGE: Yep, and so then you teed this up a little bit. You started in 2019 and then lived through the... what I love to call the sort of Number Go Up Era of ’21. And now we’re back at a different time. So let’s talk a little bit first about like how did you choose your investors along the way and what was your framework?

YIN WU: So I think that I actually, I’m quite opinionated on this especially for the seed stage I think that some of the most helpful investors that you can have, if you have that option, are former founders because I think that they have actually been in the thick of it. They know what it’s like to be in your shoes. And specifically if you can get folks that are two stages or so ahead of where you are because they can give you really tactical advice. Like, “Hey, I’m going in to hiring someone with an X profile. What are the good networks I should look at? What are the companies you should source at?” I think that type of tactical advice is really helpful. When we were thinking about who we wanted to invest when at our Series B or so we were fortunate in position because the climate was so frosty—this was back 2021, 2022—that we had a lot of optionality.

And what I was looking for was an investor I think that had worked with a number of companies. So Pulley now works with Founders Fund and Keith Rabois worked with a number of companies. So for them, a lot of it is pattern recognition. One thing I’ll say that may be counter to common advice is I think that ultimately whether the company is successful or not is dependent on you and the executive team. Even if you have an amazing investor, even if you have board meetings and so like board meetings are quarterly, if you’re only making decisions on a quarterly basis, you’re falling behind. There’s no way that the context that an investor has can be enough compared to the context that you have when you’re thinking about the company 24/7. So you kind of just want to see, do you click with this person? Do you not? Do they have past experience? And based on the pattern recognition can they help you in those moments?

ANGELA STRANGE: So you’ve brought a lot of great and with great comes a lot of opinionated people around the table. You’ve got a good story around how you had a differing opinion with your seed investors in terms of growth, do you want to talk through?

YIN WU: Yeah, I mean, I think back in that era, 2021, it’s funny because Jason and I were just talking about this down there where he was mentioning back in 2017, you guys raised like $200 million. Like if you could go back and do it again, what that would look like? I think the same thing. We raised 40. If I could go back and think about how I would operate, it would be actually quite different. But one of the pieces of pressure that we got from our investors was like “You need to go higher, higher, higher. You need to spend, spend, spend.” Because that environment at the time was, again like you could go raise the next round of funding, the interest rate is really low. Then the problem that I had in the back of my mind was I wasn’t clear whether any of this growth was really sustainable. Sure, you could go and spend a lot to acquire each customer but if the cost of acquiring this customer was so much higher than what the payback of the customer was, what happens actually on the other side?

I think the other piece of advice that we also got was hire a lot of executives. And I think it’s one where, again, this is generic advice coming from someone but like there’s cases where it really works and there’s cases where it doesn’t. If you hire an executive and they’re not a great leverage for your team, I think the split is that it’s either really detrimental or this person can be really influential. And the stats are for like VP of sales, one year is considered good. CMO, one year is considered good. So I think being really picky about who’s the right person for your company at that stage.

ANGELA STRANGE: So flashing back, I think what you said is “I want to bring people on the table who can pattern match, that have very strong opinions based on their pattern matching.” What’s your framework now around what to listen to, what to push back, how to better have those conversations?

YIN WU: I think it’s like oftentimes the way that I use our investors today is I come to them with my opinions on: here is the three options we’re considering and want to get their feedback on, out of these three options, what do they think? One, I think mistake that we made early on was using our investors to generate ideas for us. They just don’t have enough context to be like “Hey, what do you think we should do about this problem?” They don’t know, you don’t know. But if you frame that up in a way and saying “Hey, we’re considering option A, B, and C. If we hire, this is how it’ll impact our runway but this is what we can get if we really go and hit the milestone. B is that we don’t do this and this is a growth path that we’re curling on. Does this actually set us up for the next round?” I think being able to talk through that with them has actually been quite helpful.

ANGELA STRANGE: Structuring the problem.

YIN WU: Structuring the problem which is almost like 101. And I think that one of the tougher parts though when you are working with an investor and it’s something that I’m working on as well is that there is a bit of concern on how much do you share especially with investors at the seed stage. I think if it’s a member of the board, you should really share as much because you want to get as many people helping you think through the challenges as you can. If they’re on your board they’ve also committed to really being with you throughout the lifetime of the company. You know that you’re going to raise the next round. So how much do you share about how well or how not well the company is actually doing? And that’s where I found that having founders that are in your network, that you can rely upon can also help because they’re the ones that don’t really have that conflict of interest there.

ANGELA STRANGE: Fantastic, it’s been super helpful. Maybe sort of last question. You’re now CEO of your third company. How do you keep learning as a CEO and developing your skills?

YIN WU: I think there’s a few bits there. I say like at a high level there’s... you really, you can’t stop because if you choose to go on a founder route, you need to reinvent yourself at every single stage of that company’s growth. This is why executives oftentimes have a shorter lifespan because the same executive, the same person that takes the company from zero to one is not the person that’s going to take it from one to 10, is not the person that’s going to take it from 10 to 100. When Pulley first started, it was just, “How do we build a product?” So great, I was an engineer, I was a PM. And then it was like “Oh, we actually do have a product that people will pay for.” Then how do you now build out the team that can then build the product and how do you think about building out these other orgs of sales and customer success?

When I think about learning for me, one is enjoy generally reading and getting information and I try to be really intentional on reading information from very opposite ends of the perspective to form your own opinion. The second is at Pulley, we try to have a written culture so that we write down decisions we write down why we’re doing what we’re doing so that we’re going to make mistakes but that we try not to make many of these same mistakes twice.

ANGELA STRANGE: Fantastic. If anybody needs cap table software your customer success head is sitting right here.

YIN WU: We have a booth in the expo and we have sock options instead of stock options. So you can stop by and grab some swag as well.

ANGELA STRANGE: Fantastic, thank you.

YIN WU: Thank you.

ANGELA STRANGE: All right. Next, I would like to welcome Jason, CEO of Tally.

JASON BROWN: Does the microphone work? It does.

ANGELA STRANGE: All right.

JASON BROWN: It’s magic.

ANGELA STRANGE: I have known Jason more than five years. I don’t think I’ve ever seen him without a green Tally hat. So today is not going to be the day.

JASON BROWN: Gotta represent. All right.

ANGELA STRANGE: Why don’t you start introducing yourself and what is Tally?

JASON BROWN: So, hi, I’m Jason. Growing up, I had this incredible mom. She’s still alive and she’s amazing. She’s my hero. And she worked her tail off to make sure my brother and I had a good life. But I always saw that she really struggled with managing her finances. Tally’s my fourth company. And when I was between company three and four I was spending a lot of time thinking about how can automation actually extend to doing the work, not just the thinking? And so I got this idea. I want to build basically this really smart robot accountant that can do all of the thinking and the work for helping Americans manage their credit cards responsibly. So the idea was you could just give it all to the software and it would make sure they get paid at the right times. It would actually do the work of figuring out with your cash flow how much to pay, protect your credit score, and so that was what we built.

ANGELA STRANGE: Fantastic. All right, so we’re going to talk about the process of a pretty major business model change. So in transparency, we led Jason’s Series C and when we led the rounds, Tally was a consumer company. It would go directly advertising to you. There was a wonderful picture of someone with their feet up on a coffee table and financing magically flowing.

JASON BROWN: With socks.

ANGELA STRANGE: With socks, yes. And now Tally’s a B2B company. And so we’re going to walk through, if you look at just the gravitas of that decision that you had to make, which was cash cow of B2C moving over to, by definition, B2B is zero until you actually get a partner live. So maybe talk us through to the point. You’re there, you’re realizing that you need to move this business model. What’s going on?

JASON BROWN: Cool, well I wanted you all because it sounds like there’s a lot of founders to leave with a couple key takeaways. So the first takeaway I want you to have is I think in order to make it through tough times you need to really, really believe in what you’re doing. And Angela may or may not remember, but it was a couple of years ago I called her and I was crying, I was in tears. How many people here, founders have cried because of founder stress? All right.

ANGELA STRANGE: Probably the whole room.

JASON BROWN: Yeah, I just want to normalize crying and being a founder. It’s okay. It’s a hard journey, right? And so I think I was inspired to be on this... I guess, fireside because a lot of people don’t talk about just how hard it is. You’re carrying this emotional burden of hoping this dream that you believe in comes to life. You’ve promised all these amazing people that you’re going to give them 10x and they’re going to get this great carry in their funds and your employees and your own hopes and dreams. It’s like a lot to have. So I think the tears indicate you care. So if you find yourself crying, I would take that as indication that you’re really, really into what you’re doing and you care a whole lot, so. Good job.

So the place where I think I have both excelled and totally fucked up is this like unbelievable belief that this thing that you want to build should exist. And having that conviction, we heard this thing about Jensen of like 10 years. You know what? There is an alternate version of the universe where like he was 10 years too early and that was a bad bet, right? So just because somebody has conviction doesn’t mean that you should have endless conviction on the thing that you’re doing. So balancing what I would say, this is lesson number two is conviction around your mission and your idea and your dream but being much more flexible about the way that you get there. And if I were to look back, the big place where I could say there was data that said we are onto something was around our retention. I mean, our retention is incredible.

Engagement, five-year retention now is in the 80s like really build this incredible product. But the place where the data was saying the way you’re going about this is not so good is in our customer acquisition costs. Are there any folks here that are trying to build a business direct to consumer like where they’re trying to get customers? Some people? Look really, really hard at that. I think there is this balance between your pushing to try to get your velocity of customer acquisition and your cost of customer acquisition to a good spot. And there were moves that we made that would cut CAC by 30%. And we’re like, “Oh, this is good. We’ll just keep going, keep going.” But there was this point of diminishing returns.

And if I had to do it over again, probably two years before when we actually did pivot to B2B I would have said, “This isn’t going to get us in the hands of every single American.” Because that’s what I wanted. I want every single American who has credit cards to have our software helping them manage their cards. And looking back, that conviction of this needs to exist bled over into “This is the way we should do it.” So I hope you can make the distinction between caring so much about what you’re building that you’re crying, which is okay but being much more flexible about how you’re going to get there and your general approach.

ANGELA STRANGE: Great framework. Okay, so you wish you did it two years sooner but you did come to the realization that the approach maybe wasn’t the right one. But you had just raised a very large Series D based on the approach that you realized just then that you thought wasn’t working.

JASON BROWN: Yeah. There might’ve been some tears after that, too. That was hard. So I’ve been building Tally now for nine years and I think one of the things after that point that I got more comfortable with was I don’t know if I’m allowed to curse here but not giving an F anymore. I’m just like, I just want this thing to work. And like, I would put a mini lesson in there is like your ego giveth and taketh away. Like it giveth in the sense that you like, you’re willing to like run through walls because you don’t want to be a failure and you don’t want your mom to think less of you and all of that. So that’s like good. That’s the fear energy but it taketh away in that you promised all these people this picture when you’re coming to the realization that actually the better picture is over here. And I just got to the point of I care a lot more about this succeeding than I do what people think of me.

And maybe that’s not your thing. Maybe I’m the only one, but I was just like, I don’t care. We just need to do the right thing. And I don’t know if enough people talk about how the identity that they have of themselves and what they’re doing plays in decision-making but it really can screw with good decision-making even when you think you’re being rational. And finally, along with my team, I was like we need to do hard pivot to B2B and keep in mind we’re like $40 million of revenue on a consumer business. Like the consumer approach has taken us nowhere. We need to turn into a B2B business. And along with hard things, we laid off half the company. It was in January. I said, we are going to spend every waking hour turning this into a successful B2B company. I don’t think that we could have accomplished that had we been trying to also be a consumer company.

ANGELA STRANGE: So talk a little bit more about that because I think the temptation could have been “Hey, I have a gut that B2B is going to work but I have no partners yet and nothing’s live.” So you could keep one foot in both, try to get a little bit more data. And I think you just decided, “Listen, I’m the founder, I know this. I’m just going to go with it.”

JASON BROWN: Correct. And I think what I realized is that the cost, both the attention required to keep our consumer business growing and succeeding and the actual dollar cost of payroll like the math didn’t work out. We would run out of money before we got to successfully make the pivot. So part of it was math. And then the other part of it was even though this $40 million of revenue is really exciting that’s not why I showed up. I didn’t show up to do this to have a $40 million revenue company. I showed up because I wanted every single American to have this like awesome accountant that was managing all their cards, and this just isn’t going to get us there.

And so it was one of those conviction moments where we have to bet everything on this. There was obviously a lot of discussion at the board level and a lot of discomfort but I thought that, I mean, you were there. So we really leaned into wrestling with it and ultimately coming out aligned that this is what we had to do. So I thought the board was really good in providing challenge but also engaging and collectively us agreeing that that was the way to go.

ANGELA STRANGE: We’re going to talk about board, which is where we finished off with Yin. I think it’s actually something that you do exceptionally well. You now have seed, you’ve got a lot of investors around the table. So I have some specific questions, you’re welcome to pick on this investor but maybe what’s your framework for getting the most out of the people around the table and what have you found that’s the most helpful?

JASON BROWN: Think about a toolbox. Each tool in your toolbox is a person on your board or your investors. How can you put together a toolbox that has different attributes that do different things? And the one thing I can say is that I’ve... similar to Yin, been really particular about the people that I picked to be on the board. The main thing I was testing for is, are you really excited about the idea of every single American having their cards managed in a super smart way? All my board members are maybe not as passionate as me but are like on the train for that kind of journey. But from there, they’re very, very different. We have Mamoon Hamid who runs Kleiner. He’s like this scalpel, very shrewd, doesn’t speak a whole lot, but when he does it’s like, pay attention, like really detailed. If you need help, it’s more this really point of high leverage, like, I need you to help me close this one key person, can you take this call? So there’s on one side.

And then there’s Angela, who’s like a product person, a much more generalist, like how do we build the company? So I don’t call Mamoon to say, “We’re thinking about this product thing.” That’s not his bag. But I will call Angela and be like “What do you think about this? How should we approach it?” So my view is you should get this group of individuals that are relatively complementary and it’s pretty clear who you go to for what kind of challenge you’re facing.

ANGELA STRANGE: Yeah, and I think one of the things we’ve talked about is as a board member, it’s actually hard to know sometimes how much to push versus how much not to push. For two reasons. One, you back a company because you believe in the founding team, the CEO, and you’re not running the company. You want them to run the company. And then two, there is just a strong information asymmetry. You know a lot more about Tally than I’m ever going to know. And so do you want to...? I think you’ve had instances of board members pushing too much, not enough, maybe just...

JASON BROWN: I don’t know about ever too much. The one thing I would love to change mainly because it was a big screw up that I did was there’s this sense in Silicon Valley that like board members should be pro founder. And by pro founder, it means they could try to support your shitty decisions. It’s like a pro parent who’s like “Oh, I love my son so much or my daughter so much like I’ll just let them eat like pizza and cotton candy all day.” That’s to the extreme how at least I think it was.

So I think board members show that they love you by staying out of the weeds but there is the lay down on the track moments where it’s like, “Look, I’m willing to put it all on the line and challenge you really, really hard on this decision because I think it matters that much.” And if it takes us three weeks of intellectually sparring and digging in that their intuition says it’s that important even if they don’t know exactly why. So my preference would be that Silicon Valley investors actually engage less on the things that don’t matter and more on those key moments when it is this critical make-or-break decision.

ANGELA STRANGE: Do you think you’ve got probably three or four examples over the course of Tally?

JASON BROWN: Yeah, so my worst decision, let’s do that one. So we had built this awesome credit card management software and we’re like, “Do you know what we need to do? We need to also add on this whole capability so people can have that intelligence for managing their savings and their checking accounts.” Really bad idea. I mean, I don’t have time to tell you why, but just take my advice.

ANGELA STRANGE: You had a very good speech about why it was a good idea.

JASON BROWN: Oh, I did. I had like, I’m really good at selling. That’s the problem. You give me the shittiest idea and I will make you think it’s great. So yeah, it sounded awesome, right?

ANGELA STRANGE: It works well with the new B2B pivot.

JASON BROWN: It does, it’s a great idea. It actually is. So yeah, we had this whole story about how this was going to help us basically acquire lots more customers at a lower cost. It ended up being 18 months of engineer... a massive amount of engineering, lack of focus. And then we just shut it down. If I were to give Angela her hope for the future that’s why I told her this, because she, in her mind she pressed hard back on me but I was like, you needed to hit me in the head with a two-by-four to get through to me in that moment. I was like, you need to bring a two-by-four to that conversation if you have a founder in the future. I thought that was a key moment for our relationship where you like really changed the... I guess the temperature at which you brought which I don’t know, if you’re a really determined founder, you need to be matched one for one with people who will do that because I was so convicted and I needed somebody to literally hit me in the head with a two-by-four.

ANGELA STRANGE: I have apparently moved from being the level to the hammer over the last couple of years. All right. I’m Canadian, you know, I’m direct. So I think maybe many of you have investors angels, various forms, how would you advise going about building the kind of relationship that you want with your investors?

JASON BROWN: With your investors? I like one-on-one time. I think that is a really great way to get to know each other but I don’t want to belabor it. I think, are they a believer in your mission and your vision? There’s a lot of investors that will invest money but will they invest their heart? And if they’ll invest your heart.

ANGELA STRANGE: How do you test for that? Because any investor that wants to invest in your company is going to say they’re a big believer in your mission.

JASON BROWN: I think I’m going to have to... I’ll have to come back. I don’t know if I have the one, two, three on that. I mean, it’s one of those things you feel. It’s like, how do you know you’re in love? No, it is, you feel it, right?

Yeah, you spend time with them. You ask them what they care about in life, why they’re motivated. One concrete example is Mamoon, when he was evaluating, he’s like “What could we do to lower people’s APRs even more?” And I was like, “You saw our financial model, right? You realize if we do it too much, we make less money.” He’s like, “Yeah, I know.” So it’s like things like that where it’s like they’re thinking about the customer and the benefit. I mean, you were constantly digging into how can we make the onboarding experience faster, better? How could we make it better for the customer? So there was this care about the experience that went beyond just “This could be a 10x return.”

ANGELA STRANGE: But you’re overall, it’s like one-on-one which I think you spend a lot of time.

JASON BROWN: Yeah.

ANGELA STRANGE: Fantastic. Okay, maybe last question and I think you had a great framework around when to pivot business models, but any other just advice, frameworks you’d want to sort of leave with the audience that you’ve learned over your last time at Tally or companies before?

JASON BROWN: Well, I have a minute and 41 seconds, so I’ll tell you this. A place where, because I’m actually going to riff off the question you asked Yin of how do you develop yourself. I think as a founder, you should go to two extremes. So one is, and I’ll make this concrete obviously there’s all this buzz around AI and everything, and we’re not an AI company but as a founder and when I’m talking to other founders and even I was talking to a founder at a Kleiner event who has an AI company, and I was asking him to explain his transformer model that was used for the implementation. They had, and he wasn’t able to tell me how they tokenized the pieces of data. I was like, but what is a token? How do you choose a token, and how do you set temperature? And he didn’t know, and he was the CEO of an AI company.

So I think one extreme is get really deep into the fundamentals. Like how does a transformer model work? How do the layers feed back and forth? And like, what are the... You don’t have to be able to code it yourself but get into the level below the hype and really understand so that you have this intuition on how these things work, and you can explain how tokens get input, and how a token gets predicted and effectively how ChatGPT works. On the other extreme, how humans behave. So I’ve spent the last couple of years studying conscious leadership which is really understanding how our minds operate relative to our primitive brains and how that feeds into all of our decision-making in our relationships. So I think that like barbell strategy of thinking about the underpinnings of technology and the underpinnings of the human brain is ultimately how you become a well-rounded CEO.

ANGELA STRANGE: Fantastic. Jason, thank you, much appreciated. Thank you everybody for joining us.