
How do you know it’s time to move on from a product that’s growing?
In this episode, Rob Walling chats with Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), about a rare founder journey: bootstrapping, catching lightning in a bottle, and choosing to go big with venture capital. They dive into the emotional and strategic weight of shutting down a $1.5M ARR product, what shifts when you scale past 40 people, and why Braden prioritized long-term vision over short-term revenue.
Topics we cover:
- (2:30) – From FinChat to Fiscal.ai: rebranding and repositioning
- (6:50) – Why they raised a $10M Series A
- (13:09) – From bootstrapped to venture-backed: what changes?
- (19:56) – Becoming a real CEO at 25 employees
- (26:44) – Why they shut down a $1.5M product
- (30:30) – Lessons from having four co-founders
- (33:13) – The benefits of joining TinySeed
Links from the Show:
- MicroConf Connect
- The Great CEO Within
- TinySeed: SaaS Institute
- Fiscal.ai (formerly FinChat)
- Braden Dennis (@BradoCapital) | X
- Braden Dennis | LinkedIn
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
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You’re listening to Startups. For the Rest Of Us, I’m Rob Walling. In this episode, I have a conversation with Braden Dennis. He’s come back on the show. He’s the co-founder of Fin Chat and they have recently rebranded to fiscal.ai after raising a $10 million series A. I don’t cover a lot of venture raises on this podcast because we focus on bootstrapped and mostly bootstrap companies. But now and again in our ecosystem, we are seeing bootstrappers who catch lightning in a bottle and they realize that the opportunity that they’ve stumbled upon as much more potential than they originally thought. And some of those folks decide to sell early. Some folks continue to bootstrap and others decide to go that venture route. And today, Braden and I discussed that decision about why he and his co-founders decided to shoot for the moon. As you can tell by the title, we also talk about how they shut down a $1.5 million a RR product.
And we do a quick recap of what got them here. You can hear more of that in his prior episode, which I mentioned during the interview. Before we dive into that conversation, I want to let you know about our MicroConf local chapters. Building a Business can be isolating, but it doesn’t have to be. So inside MicroConf Connect, which is our online membership community, we are launching local chapters to help you meet each other in person. Our first local chapters will be taking place in Barcelona, Toronto, Sydney, Austin, and London, giving you the chance to share challenges, exchange ideas, and build relationships with other founders in your area. Alongside these local chapters, we’re also opening up the MicroConf Ambassador program. If you want to help bring founders together in your city, you can apply to become an ambassador. We’ll provide everything you need, a comprehensive playbook, promotional support, and swag to make your events successful because no event can be successful without swag.
Am I right? If you’re looking for accountability, collaboration or just good conversations over coffee apply to join MicroConf Connect and become a part of the community. To learn more about local chapters and the ambassador program, head to MicroConf connect.com. And with that, let’s dive into my enlightening conversation with Braden. Dennis Braden. Dennis, welcome back to the show, Mr. Walling. It’s always good to see you. So good to have you, man. So you are on episode 705 of this very show. It was March 19th of last year, so just over about 15 months ago. And we talked about how your SaaS app called Stratosphere, how you went from bootstrapped to taking money from Tiny Seeds. So we said mostly bootstrapped to then going venture backed. And I believe you had raised what pre-seed round, what was it? 2 million, 3 million? It was one and a half. One and a half.
And we covered a bunch of topics. You rebranded to Fin Chat and have more of an AI bent where you could chat with what public market data really is the thing that you have, how you had launched a second product and you and I talked through, I was like, my advice is usually not to, and when is an exception. Right? We talked through in that episode and then you, I mean, I guess catch us up. You raised that venture round and now you’ve just raised another. You’ve raised a $10 million series A, which is a load of money for a bootstrapper. And I still think of you, I mean you guys are moving fast. It’s a big ambitious space and you’re now a venture back company, but when you and I first met you, were a podcaster with a little B2C personal finance app. So catch us up on the last year or year and a half.
Braden Dennis:
Yeah, I mean total funding to date is now 13 million us. And it sounds insane to say because it’s not so long ago. I met you for the first time in Austin, Texas after TinySeed, and yeah, it was like, okay, we’re just going to take this little bit of money. Me and my co-founders we’re going to try to get this to a few million in a RR. I mean, at that point, your only goal is like a million in a RR, a million in a RR, a million in a, I will be happy when I hit 1 million forever.
Rob Walling:
You’re going to be happy forever,
Braden Dennis:
Forever, forever. I’ll be fully content. There’ll be nothing wrong with the world. And so that was our goal. And then yeah, we launched this kind of second project because almost more out of curiosity, what can we do with an L-L-M-A-P-I? It took off. So then we kind of merged the products and then more and more has happened since then. We’ve had more ambitions to actually just go after these big players, go after the data infrastructure, what we can do with AI behind the scenes. And so we figured we pivot a little bit away from the chat name. People were kind of pigeonholing us to that name, doing it with the series A makes sense. And the prize that we were then now set on, we realized that we were going to need a significantly more amount of capital somewhere between five and 10. And every venture investors take more and go try to get this thing. And you know what? I don’t think that’s venture investors trying to be evil. They’re actually right. They’ve seen pattern recognition. You’re going to need more capital. This is AI and you’re up against people who are raising hundreds of millions of dollars in some cases.
Rob Walling:
And so let’s talk about that rebrand. So you’re now@fiscal.ai and your H one is the modern financial data terminal, go from idea to confidence with clean global financial data, trusted by the world’s leading public market investors. And your site looks gorgeous, by the way. It’s a really nice rebrand. So moving from fin chat to, well, fiscal is a great name, especially fiscal ai. So the part of that was to not be pigeonholed as just like a chat app. Is that the idea?
Braden Dennis:
Yeah. We’re like, okay, we’ve become finance plus AI and FinTech kind of resembled that. But we would talk to these big bank investors, these public market investors. We had two problems. One, they thought it was just a financial chat. They thought we were maybe like a Bloomberg chat competitor, which was not really true. It was a full actual data terminal product. So they were pleasantly surprised when they came to the demo. But still we were underselling a bit what we were doing. And two, a lot of big bureaucratic financial buyers. They had almost all AI chat domains blocked on the server. They didn’t want anyone putting in customer sensitive information, proprietary trading data, stuff like that. And so we were just always blocked. So those first demos, no one had ever seen the product before and that was really hurting our go-to market.
Rob Walling:
That makes sense. And as you said, timing it with the series A makes a lot of sense because you have the money to acquire the domain and to do the redesign. You touched on it briefly, but I want to double click on this thing you said of we had raised the 1.5 million and we had fin chat and it was working, and then we decided to be more ambitious. We decided to take on the, I forget the terminals of the world or something like that. And that’s why you raised the series A, right? You just need a bunch of money to do something. But tell me what that is. Why do you need a bunch of money? Is it just because the others raised it and who are you competing? Maybe talk us through fin chat. What is it? What was it in 30 seconds? And then what is fiscal and how is it so different that you needed to raise eight figures of funding in order to go after that opportunity?
Braden Dennis:
Yeah, it’s a fantastic question. So the landscape of our industry today is dominated by primarily three or four massive tens of billions if not hundreds of billions. Each player of market cap on the public market, some of their stocks are worth over 100 billion, many of them in tens of billions of dollars. And so if you think about what they do, they are essentially aggregating financial data with people at scale, tens of thousands of people manually aggregating financial data at scale. And our vision was how can we do this better, faster, cheaper with technology? And so as our ambitions started to grow in terms of going after that big prize, it became clear that one, we were going to need a larger team, we’re going to need a lot more engineering, especially on the data side, and we’re going to need a pretty thought out B2B go to market plan that is not going to fly with a million or two in the bank.
I think it’s a little bit tricky to understand, but one of my investors said with salespeople and the most talented go-to market folks, they’re either going be the newest people on your team because there’s a lot of churn, or the highest paid four or five times more than the CEO O at a successful startup. And I was like, that really broke my frame of reference because it’s like, oh wow, they’re actually going to make way more money than me if they’re closing deals the way that we actually need to go from zero to five to 10 to 20 to a hundred million in a RR. If you just reverse engineer how much these people should be making, it’s significant. So you kind of need a little bit more capital if that’s what you want to do. It’s not the only route. Capital is just a method to live in the future, as you would say. And I totally agree with that. The people that I wish I could one day afford or or work with, I can work with them now. And that’s awesome. To me,
Rob Walling:
It’s a big deal. I like what you touched on with what your investor said because most founders, especially bootstrap founders, don’t realize that a salesperson, a GTM person at a startup like yours, if they make, let’s say a salesperson makes a million dollars in it’s obviously salary plus commission, they should be generating, I think that it’s a loose 10 to one. I think they should be generating 10 million in a RR for you, so therefore it’s a really good deal for you. Even though it sounds a million, what are you insane? We can’t afford that. And it’s like I think what you’re touching on is
Braden Dennis:
Most folks would be like, oh, I’ll never pay someone that much. But then if you say, Hey, do you want 10 million in a RR? They’d be like, of course I pay a million for that. No problem. Exactly. Yeah, yeah, exactly. And so that has taken me a little bit of time to come to terms with a little bit, and once you come to terms with it, then you can really actually build the right team and grow and make the right capital allocation decisions. And sometimes it’s not always the cheap scrappy way. You can still be frugal in other ways and I’m recording this from my very cheap office.
Rob Walling:
Yeah, totally. Well, and that’s the thing, right? It’s like could you bootstrap or mostly bootstrap this idea? Maybe you would just have to approach it really differently and you would’ve to grow it slower and you could still maybe build a smaller business that’s super profitable, maybe I don’t know all the intricacies of it with the AI and the costs and stuff, but there’s usually multiple ways to build these businesses. Super bootstrapped, mostly bootstrapped, and then raising a bit of money and then raising a load of money, which you’re teetering to me, you’re teetering right on that shit load mark. But if you want to go after something that is really crowded, where it is winner take most and where it’s a land grab, that’s what it feels like to me is that what is happening in your mind
Braden Dennis:
Across just the three players. And this is not including Bloomberg because Bloomberg is privately held, so it’s hard to say what they’re doing. Most people think they’re doing over 10 billion in a R, but just the major public companies in terms of what we’re doing and the segments that we’re competing, 13 billion in a R across that kind of oligopoly. And so it’s worth going after this prize in my mind. And I think the more that I’ve built, the more that this has remained true is when we were working on something with a smaller goal and really just focused on that 1 million a RR, which by the way is a great goal for everyone who’s starting the business. It’s not like I was spending less time thinking about this, losing less sleep than I am now about what I want to do with the business or the amount of work required or the weekends or the evenings. I’m all in regardless. So let’s go for something really big, especially if I’m going to take on investor capital. I mean, I’m running an investor financial data business. I came from this as an investor first, so I taking someone’s capital seriously because I was on the other side of that transaction for 10 years prior. So yeah, I mean I’ve been an investor in public markets since the day I turned 18. I could open up my non-registered account. So this has been something that I’ve thought about for a long, long time.
Rob Walling:
Do you feel like taking this much money, obviously it implies that you have to get a lot bigger. I’m assuming you want nine figures meaning a hundred million plus of a RR and maybe 10 figure you’re talking 13 billion of a RR. You want to took that. I mean I don’t think it hurt your feelings to get to a billion a RR, so obviously it means your goals, your aspirations, they’re just bigger. They have to be. Do you feel like simultaneously that increases your chance of failure?
Braden Dennis:
Yes, it does without a doubt. And I think that this is the one thing that me and my co-founders hummed and hawed on the most as I sat them down because I deal with all the fundraising and talking with investors as the CEO and I told them guys, this changes our floor of success has to be so much higher. Our ceiling can be a lot higher, but the floor is now on level 12 in the elevator and we’re only on level three right now, so we have to go a lot higher for this to be a success now if we go down this route. So we had to come to terms with that. But like I said, we’re still hungry. We still wanted to work for it. We’re like, we’re probably going to get there anyways. It’s just going to take us longer if we have to scrap this all together with a million in the bank versus 10.
Rob Walling:
Yeah, it makes sense. Something I’m really happy with is that when Einar and I sat down to figure out the TinySeed investment terms, and this was seven years ago, it was 20 18, 19, we were just trying to figure out all these terms. There was indie VC had kind of this thing where you could pay back and buy back equity and it was like phantom equity and it was like maybe that’s interesting, but also it’s a little complicated. And then other competitors came on the scene with similar things, but they had accidentally or intentionally exploding terms where if you raised and you didn’t pay it back, suddenly they own three times more of your company than they originally. Just bizarre stuff. We are like equity is equity. Equity has existed for a thousand years, 800 a very long time. And so let’s keep it pretty simple. We do have a side letter of course, because there’s salary and participation caps and stuff.
You couldn’t just pay yourself a million dollar salary and not pay TinySeed anything, blah, blah, blah. But one of the things we wanted to be really careful about was that we want TinySeed companies after they take our money to have optionality. If you never want to raise money again and you want to basically be mostly bootstrapped great, if you want to raise a bit of money, if you want to raise a lot of money, we didn’t want that to negatively impact your ability. And you are one of several founders who have raised a lot of money, seven or eight figures and had, at least from my perspective, I just signed the docs, I don’t actually, lawyer tells me to read, doesn’t seem like our terms or being affiliated with TinySeed had any negative impact on your raise. Is that true?
Braden Dennis:
No, and I think that you guys have been easy to work with because what I’ll say is the newest investor in always wants to be the biggest swing in what? So they basically, as the lead will take those terms and previous investors, of course there’s dilution, there’s no way around this kind of inevitable feat. You get your markup, there’s a little bit of dilution. That’s the world of raising additional capital. Same with my holdings too. We’re all losing a little bit on new money in, but the terms that are coming in with the largest investor is kind of like they want it their way. And you guys have been very easy to work with on hey, they want this way, but you’re still going to get this. You’re still going to get that. You’re still a major investor. You don’t lose any of this or that. And I think that that’s a good way to do it, right? Because you’re giving us optionality to keep growing. If we to didn’t want to take any money, that’s also fine too. So I think that’s the right way to do it because businesses change over time. A startup doesn’t. When we first met, my business was a lot different. It was two names ago, Rob, $10 a month if I remember. It was
Rob Walling:
Crazy.
Braden Dennis:
It’s night and day. So you have to be flexible, you have to be pivoting and you need investors that are open to that as well because really good investors know that you’re betting on that. I’m going to figure it out.
Rob Walling:
And that’s something, I’ll tell you what, early on with TinySeed, I did a MicroConf talk and I remember saying something like if we start funding, I don’t even think TinySeed existed, but I was like if I was going to invest in Bootstrappers, it would be one round and then they’d never raise again. They’d never have to raise again. And I remember coming off stage and a R was like, don’t say that because you don’t know and it was a real good wake up. You don’t know if they’re going to want to raise some businesses. We might invest $150,000, $200,000 and it was a very small amount of money in the scheme of things. And if they catch lightning by the tail, they might want to raise 3, 5, 10, 20 million. And it’s a small subset of Chinese companies, but there are decent chunk of folks who’ve done it.
And so a, I’m glad that our terms, that was the intent was to allow that optionality. That was a big thing with TinySeed is hey, you can sell for 10, 20 million but you can also go after the big one. But it is a reminder or maybe to a listener. There are a lot of listeners who are just diehard, bootstrap, bootstrap, bootstrap. I just want a lifestyle. That’s what Drip originally was. I was trying to build a little lifestyle business that was going to generate a bunch of profit and then guess what? I found a bigger opportunity and I just took it in a different direction and that changed my life. I was open to that possibility of changing my mind. Did you think when you bootstrapped stratosphere, I had to, since it’s two names ago, I almost said fin yet, when you bootstrap stratosphere in your mind, were you early on will never take money. I would take money on the right terms, definitely want to raise money. Where were you on that bootstrapping continuum?
Braden Dennis:
I mean I think I’d be giving myself a lot of credit if I think I had any sort of clue what was going to do at that point. But generally I wanted to build something that would, me and my co-founders could pay ourselves a little bit of money, maybe hire a couple people. My dream was to have this kind of bootstrap can do whatever I want cashflow business so I could live in Bali and surf every day. That was kind of my goal. But things change the business change, your personal life changes and you just want different things, especially when we started this business. I’m 29 now, so I was 26. I didn’t know what I wanted to do beyond what I was going to eat for lunch that day. So I don’t think I had a grand vision other than I knew I wanted to be an entrepreneur. That’s pretty much it. And I knew I wanted to help solve the problems that I saw in finance
Rob Walling:
And you were open to being open to what comes and it’s like, hey, maybe we’ll go bigger. Maybe we’ll rebrand, maybe we’ll raise some funding. I’m curious as, I mean you’re a 29-year-old CEO of a company that now has 34 people on your team and you have six more starting shortly, you’re about to be the CEO of a four person company. I mean that’s bigger than any company I’ve ever run. Drip was 10 when I sold it. I guess I was running a team within the acquisition or the acquirer of maybe 21 at the end. But even TinySeed, MicroConf all combined today is still like 10 people. So 40 is significantly more than I would even enjoy. I just don’t enjoy managing a lot of people. There has to have been some maybe learnings, growing, pains, just all of that stuff. Again, you’re obviously highly competent, very intelligent, but you’re a young dude. I don’t think you’ve managed 40 people before. So what is this feeling like for you these days?
Braden Dennis:
When we hit 25 people at the end of last year, I had a major wake up call. It slapped me in the face once we hit 25 and I hadn’t built the right infrastructure for a company to exist at 25 people. We were just flying by the seat of our chair. It was just me and my three co-founders and then I woke up and there’s 25 people and it’s like, whoa, okay, we got to see. I have to actually become a CEO. And so I started trying to learn and trying to focus and just take the realization that this is not just me and my co-founders hacking away trying to make money on the internet anymore. This is people are making real money, real salaries, real lives working for us and we need to build a really sustainable scalable company as we can go. And so that’s the wall I would say is 25. And I was like, okay. I say I’ve been the CEO of this company for two years, but I haven’t been now I need to be. And I think I’ve gotten a lot better honestly.
Rob Walling:
What were some examples of things that maybe weren’t working that you had to then add structure in order to fix
Braden Dennis:
A book? I’d recommend to everyone is called the great CEO within. It’s the tactical guide to company building. It’s short, it’s like 200 pages. It’s just step-by-step advice. There’s lots of amazing CEOs who have chimed in certain sections, whether it’s Brian Armstrong of Coinbase or the guy who did Clearbit. A lot of people came together to build this book and it’s a book that every Sequoia founder is given when they invest in them. And so I read that book that really helped me frame around this idea of if I have to do it twice, it needs to be an actual process or written down somewhere. A company, Wikipedia, it can be as simple as just utilizing a Google drive better and file systems, just little things like that. If I have to do it twice, it needs to be a system. A lot of stuff you’re going to start having to repeat all the time, whether it’s hiring, whether it’s operational stuff, whether it’s sales.
I was wasting so much time starting from scratch every time I was doing something. So that really, really helped. And then secondly around how to properly encourage my employees to succeed and tell them that they’re doing a good fricking job because a lot of them are doing an amazing job. And I think that before I was just, I assumed that they knew that I thought they were doing a great job. It is amazing what happens when you tell just some simple recognition of how good of a job they’re doing. Some people who are killing it at our company, crushing it, working so hard and they’re so happy here. But it is amazing what some recognition or some recognition on a team call could do some structure. Every Friday, every single person in the company talks at our meeting now. Before it would just be me telling them what we’re going to do next week. Now it’s every single person telling me what they’re going to do and asking me how I can help them. So that has massively changed the way that the business has operated, I would say. But it’s not hard, Rob. We’re doing stuff that’s way harder than these things that I’ve had to figure out. This is easy, easy stuff, but it goes a long way.
Rob Walling:
Yeah, that’s a great book recommendation by the way. I don’t know that I’ve actually read it, but I have heard, I’ve seen it and I know folks recommend it.
Braden Dennis:
No fluff in that book. It’s very straight to the point. Yeah, it’s tight.
Rob Walling:
Yeah, it’s real tight. Yeah, 200 pages. Do you enjoy being the CEO of a 40 person company specifically?
Braden Dennis:
Sometimes no.
Rob Walling:
Yeah, yeah. I was going to say, because there’s got to be some hard days. There’s got to be some complicated days with it.
Braden Dennis:
There’s some complicated days, but there are some days that are so freaking good as well that the highs and the lows are certainly there. And if I don’t manage myself with the highs and the lows, my employees know it and feel it. So I have to be pretty even keel. So there are certainly days that are not as fun. There are certainly days that are a ton of fun, but at the end of the day, I don’t want to do anything else differently right now. So it would be a problem for me when there was hard days if I was just like, ah, there’s something that I really want to do that’s not this, but I don’t have that. I want to see this thing work really well. So that kind of keeps me going. Yeah, I
Rob Walling:
Think growth also always used to keep, I know your growth curve obviously because I’m an investor in AC and it’s like you’re growing very fast and for me, M-R-R-A-R-R going up into the right, it made a lot of ills go away for me. I was just like, you know what? It’s working. This is hard. It’s not supposed to be easy, but if you’re doing all this grind and it’s flat, it’s terrible. It’s the worst. You’re just like, none of this is worthwhile. I’m wasting my time. Why am I doing this? So it growth cures most ills. I think
Braden Dennis:
A r growth solves a lot of problems, including my ability to sleep well at night.
Rob Walling:
Exactly. Alright, so I want to ask you, we were talking offline and you threw some bullets into a doc for me to help guide this conversation and one of the things that you said was something we could talk about was why I shut down a B2B product that went from zero to one and a half million a RR in 12 months and then I shut it down. Talk us through what was that product and why?
Braden Dennis:
We started licensing our AI copilot product, which is basically you could converse with all the financial data, get it to build you graphs, get you to summarize transcripts, slide decks. Everything was preloaded into there. We exposed that product while we were trying to build a ton of other product. So it was just a lot was going on. It was a bit of a distraction, but the money was flowing in. It went from zero to a million and a half of a RR growing 20% a month consistently. Even when I shut it down, it would probably be like two and a half, three today, maybe more. The problem with it was we were signing big customers, one of them was $250,000 a year. Several were in the hundreds of thousands of dollars. Someone that just tens of thousands of dollars and a lot of customers were coming offline pretty quick and telling us quickly that they were not going to renew.
And the reason for that was we solved a key problem at one point that chat, BT couldn’t handle any of these queries very well. That problem went away and the foundational model started to kick our asses at our own game. And so we started to see the writing on the wall. We’re like, okay, this is not actually what we’re good at us doing rag for them and solving this quick problem for these customers. It’s probably a quick solve because they want AI on their platform. Yesterday the CEO’s begging the product team, why is there an AI not on our product? We were a quick solution, a quick fix for them, but it wasn’t the right solution for them. Then they would say to us, how do I connect my customer service bot to this as well? Or how do I connect my customer? Clients are asking how they do their own account openings and it’s getting confusing.
This was a very narrow product and we said, oh, sorry, I can’t help you with that. You’re going to have to build it from scratch with our data. And then they started doing that and that had product-market fit, and so we shut down this out of the box solution that so many people loved right away because the actual slower longer implementation we’re customers that I think will be with us forever. And that is a materially different type of anxiety. When you see 30 customers sign up and 15 of them turn before three months in, that’s brutal. Terrible, terrible. So we just said, screw it. We are going to shut it down with the financing. And that’s what it is. It is what it is.
Rob Walling:
Wow. Yeah. These are hard decisions. Did you feel it’s hard decisions we in complete information, did you have much doubt when you did that? Because that’s a one way door ish type of thing that’s really hard to undo. Were you convicted and you were like, no, this is the right way? Or were you like, oh, he and Han trying it on for weeks and months?
Braden Dennis:
I knew it was the right decision when I was, how much it was causing issues with our development team for building the long-term product that we actually envisioned because there was a lot of bugs. It was a lot of customer service requests that we just were not getting for our core foundational product. People were way more happy there. So a combination of churn and distraction from the dev team was enough for me to go, look, this is not what’s going to make this business a success, so reverse engineering that. Yeah, it’s tough to say no to that much revenue when you’re at our size, but I think it was the right call. It’s still really early to say, right, it sucks when customers ask us today if they can come buy it. And I’m like, no, you can’t. I got
Rob Walling:
To say no. Turning down revenue is the worst. Yeah, the worst is saying yes to revenue and having it churn, but the second worst is turning down revenue. I want to switch topics a little bit. I just have maybe two more questions for you, but one is about, you have three co-founders, so there’s four of you total. And I’m curious, we talked about this last time we recorded, so I won’t go too far into it, but I’m curious now that you’re here where you are with a 40 person team and you’ve raised all this money, what’s maybe the biggest positive to having that many co-founders and the biggest negative that you’ve seen?
Braden Dennis:
The biggest positive is that there are four of us across the different parts of our business that have an amazing leader on day one. That’s the biggest positive. So me as a CEO, my chief product officer, one of my co-founders, my CTO, one of my co-founders, so they run tech and product and they are outstanding at what they do. And then my CO Adrian runs all of our data operations and just operations in general, and he is the dream hire. So I had kind of the dream hire on day one from day one, building the business, and to me that is super, super valuable without a doubt. Plus I love these guys, so it’s nice. It’s great hanging out with them every day. So it’s just a good team. We get along great. The biggest downside I guess would be I could see the potential for clashing when it comes to decision-making, hiring product decisions, long-term vision.
But I think if you were to ask my co-founders, they would say that I’ve earned their trust to unequivocally make almost all of those decisions and ask them if it’s okay and they give me the green light, but we don’t pose strategic questions and say, what do we think? I pose the strategic question, say, this is what I’m doing, this is where we’re going to go. Does anyone have major issues with this? If so, then speak up, then we will reroute, but if not, and I’ve gained your trust and your leash to be able to make these decisions, then let’s go. So everyone focuses on what they’re good at, and so I think the pros majorly outweigh any cons in my view.
Rob Walling:
Yeah. Well, it seems to be working for you too with the growth and the success. Obviously raising funding is a tool and it’s a milestone. It’s not the finish line. You and I both know this, so I don’t want to, that’s not worth saying on the
Braden Dennis:
Finish line. Got a lot further away when you do this money,
Rob Walling:
It just extended the finish line. So last question for me today is regarding TinySeed, when this episode goes live, TinySeed applications will open like a week or two later for our next batch or 16th batch or something like that, September one. And I’m curious, I don’t know quite how to ask this question and maybe it’s like what are the top three or four things you and your team, your founding team got out of TinySeed, or maybe if someone’s on the fence they’re listening to this, what would be the benefits for them joining? And maybe you could even say, what if you want to do X, don’t join TinySeed. You know what I mean? The pros and cons. We don’t have to go full person cons, but it’s kind of like what did you get out of tiny C that would lead someone to apply it and want to do it?
Braden Dennis:
Yeah, there’s three things. So if you’re comfortable with saying, I think it was 200 K that we raised from you guys, and so at that time nowadays I’m like, what do I do with that? Right?
Rob Walling:
Yeah.
Braden Dennis:
But at that time, when you have 10,000 in the bank, it’s everything, right? So it’s that frame of reference. So that did materially actually help us. I’m not going to lie, especially with our vision, which it was in a sweet spot for us at the time. Of course, the vision changed, the ambition changes, but at the time it was the right amount. The second thing that I think was super helpful was just, yeah, just early on we were using you and a NRA lot around pricing, which customers are working, what do you think about this strategic is freemium versus not. Some of the basic questions that you talk about on this podcast a lot are super helpful for anyone listening, but it’s even more helpful if we can talk specifically about my business. I can learn from Joe’s other business, but when we’re talking specifically about my business, it’s obviously a lot more tangible. So that would be the second thing. And then the third thing is I don’t actively participate in the Slack community, but if I have a question, I know it’s going to get answered really well by 30 people in the matter of hours. So I would say I am more of a receiver of information more than a giver on there. So it’s probably more of a one-way street for me. It should probably be a little bit more reciprocal, but that’s just kind of what I get out of it. It’s amazing me, to be honest,
Rob Walling:
I’m glad. And it’s funny with the first batch or two, the Slack group was obviously tiny. There were 10 founders and then 20 founders or whatever, and Einar and I used to have to answer a lot of the questions and it was just like, well, no one else knows. And so I am going to give my best answer, and there’d be others stuff trickle in. Now by the time we have an advice needed channel, for those who don’t know, by the time I get to any question, there’s already five responses and I tend to look through and be like, Ooh, that’s smarter than what I would’ve said. Oh, he’s done it more recently than I have. Oh, she has better insight. And it’s usually like what they said with an arrow up, or maybe I have a little bit to add, but it’s like I’m no longer the expert. I don’t have to be the me Rob Walling doesn’t have to be the expert on everything, and I shouldn’t have to be because there are 300 something, there’s 204 companies and I think it’s 310 founders. I don’t know the exact number, but it’s very knowledgeable. People like yourself that are really knee deep. If someone’s like, Hey, I want to know how ML stuff and data and financial whatever me, I don’t really know, but you or your co-founder Kevin or one of your other founders is going to really know it.
Braden Dennis:
Even stuff like this, we’re a Toronto, Canada based startup and there’s a Canada channel, and we have specific questions around our tax situation, our HR situation that we’re a little underserved because most of those questions on the internet or in these types of Slack communities are specifically about US tax or US regulations. So for us to have our little corner where we know we’re dealing with the same context is pretty helpful.
Rob Walling:
That’s great. Well, Braden, thanks so much for coming back on the show, man. Folks want to keep up with you on the internet. Of course you’re brado capital on X Twitter, and if they want to see what you’re building, it’s fiscal.ai. Thanks again for joining me. Thank you. Thanks again to Braden for coming back on the show. And thanks to you for listening this week and every week. This is Rob Walling signing off from episode 787.
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