Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
Full method →
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q So walk through what was the set of insights that you landed on before you actually built or shipped the first product?
A Yeah. So on the plan sponsor, the small business owner side, you hate wasting money, right? At least, at least I did at TaskRabbit. So if you're going to offer a benefit, you want people using it. So again, that participation rate, why are they not using it? I'm paying 20 grand a year for this. Nobody's using it. Nobody's getting the benefit. Nobody understands the benefit. So that was one. And then the other one was like, people need to understand that small businesses can afford a four or one K if it's done properly, just because you don't have assets doesn't mean they won't build over time. Right? Like that's the whole point. So, and then make it as easy as possible. So for us and ADP and Sequoia, like our payroll and our four one K weren't even integrated and it came from the same company. And that was just like mind blowing to me. Why am I validating Contributions after every pay run. Why, why am I doing this? That should all be handled in the data set in this product. Um, and it wasn't, and that's kind of the way it is even today with some of the larger legacy companies. They still haven't figured out that you need to have this seamless integration. The small business owner doesn't and isn't qualified to administer a for one K. Um, and, and part of our first product was building these. 360 degree integrations with forward thinking payroll companies like Gusto. And that wa…
AI assessment note: “So that was one. And then the other one was”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Then did you have a, uh, AUM style fee as well?
A Yeah. So early on, we didn't have any asset based fees whatsoever. So it was zero. That was really important to get to, but we were losing money, right? I had to pay the custodian. So that was really important to understand. What I didn't understand early on is that custodian, not only were they charging a very small asset-based fee at the time, but they're charging a transaction fee. So when you had certain things happen in a four one K you want to take a loan or a hardship withdrawal or a distribution of some sort. You got charged essentially a distribution fee. They mailed out a check, right? Like that cost them money. They charged us money. We had to charge money for that. The experience that really brought it home for me was actually a, an early participant was in a car crash or had a flat tire or something and needed money and they needed it immediately. And guideline was charging them, I think, a hundred dollars to get a distribution because that's kind of what we were getting charged. And that was really important for me to understand. So somebody is coming to guideline who they trusted to like save for retirement. Now they need help. And we're going to charge them a hundred dollars to get it. Uh, just felt really terrible, quite honestly. So we started charging a small asset-based fee on the entire platform to cover all transactions. So that's what we do today. We char…
AI assessment note: “So we started charging a small asset-based fee on the entire platform”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Did you figure out the integration insight before you started the company and raised money?
A I didn't. That came after, obviously I knew, I had known about this problem with ADP cause I was experiencing it myself at TaskRabbit, but I couldn't figure out the angle to make Gusto care or make my first payroll partner. Care that I was going to go do this. And eventually we figured that out. And that was really important to understand. But one of the things that I didn't realize until after the fact, and Gusto actually told us this. So payroll in the United States is incredibly fragmented, right? They have high churn. It's 25, 35% on the higher end of their annual logo churn. So when you take that into account and you attach a four one K or an integrated four one K solution to the payroll product, it cuts it in half. Right. So their LTV doubles, which is fantastic for them. Right. So now I'm starting to think this is why they're going to care because I'm going to cut their churn in half when they attach a integrated for one K and now I can start paying them as well. Right. Like the long tail of it with that integration, it gives me operational scale. I can actually start giving them money. Now I'm giving them, I'm giving them money for essentially maintaining an API. Right. That's a hundred percent margin business for them. So that makes it really exciting. Doubles the LTV and I pay them. Now I'm starting to understand like, hey, this go to market motion has legs. Now I hav…
AI assessment note: “I didn't. That came after, obviously I knew, I had known about this problem”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q Maybe we'll just start at the beginning. What, what was going on like a year before you started the company?
A Yeah. So that would have been. I was still at TaskRabbit. Uh, really the inspiration behind guideline was some of the earliest employees. They're not using this benefit called for one K. And that was something that's, you know, me as a little bit older, I was in my late twenties at that point had come from previous startups and also larger companies like IBM. I knew what a for one K was. I knew what a pension was. Um, and I saw a ton of mistakes and the biggest mistake you can make in for one case, not participating. And that's exactly what happened at TaskRabbit. So for that, that's kind of where the inspiration came from. It's like, why they kept coming up as a founder, you always think of yourself as wearing, you know, so many different hats. And this was one I just, I wasn't qualified to wear, but people were asking me anyway, as like the older person there, I guess. And kind of, I did, you know, VP of engineering and technology stack, et cetera, but I also, Ran some portion of HR, and they're asking me about this, and I couldn't really help them. I wasn't knowledgeable in it, and I started digging into it, and that was really the inspiration. This is a problem, and I'm a problem solver and a builder, and I figured, you know, I could probably take a, take a hard look at this and see if I can find the right angle for me, and also to develop a product that I would want.
AI assessment note: “I was still at TaskRabbit. Uh, really the inspiration behind guideline was”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q Did you use any existing providers or every single thing was built from scratch?
A Everything that we could at the time we built from scratch. And that what I mean by that is the thing that we were very careful to understand was if we're going to be build record keeping, what we're not going to build is like the trading platform, right? Like where does the money actually clear? Right? So we signed up with state street bank through an intermediary or custodian, and that was really important to understand. So there's a lot of the early questions are where like, Hey, you're San Francisco, Startup and you have 90,000 dollars in AUM, which was like, you know, mine, Cavs and Mike's money at the time. Like, what happens if you guys disappear? Like, where does my money go? And that was really important to understand. So it wasn't just guideline, but it was guideline and intermediary, um, subcustodian, then state street banks. So the assets were all at state street banks. So when you say that, and it's like the oldest financial institution in the world, like your money's over there. In the end. So like that gave people a lot of peace.
AI assessment note: “we signed up with state street bank through an intermediary or custodian”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q Why do you think people problems and building a team and why is that always so hard?
A I think there is this sort of curve to it. You start off incredibly technical and you're setting the vision and you're talking to, you know, your co-founders on what it should look like and et cetera. And like, That is a skill set that you already possess, you knew about it, you built your company around it, and then you get into a hiring phase where you're meeting demand, you have product market fit, and you're trying to scale, and now you're in a hiring process, and I'm a, I'm an introvert, and like, it's very difficult for me to have, you know, large scale interviews when you're bringing on 10, 15 people a month. That is something that's just not natural to me as a person, and I think you're always going to find that. An individual can't be everything to everybody all the time. So you lean into what you're good at. I think over time, when you actually have some success, you can start like picking and putting on like what you do want to work on and what you don't want to work on and make sure that you fill the gap that you understand that you have. My CTO is a great example, and we've been lucky enough to bring on an incredible VP of engineering, but Mike started early coding. He was the only one we had. He was doing all of it. And then, you know, year Three, year four. He's like in this architect role. He's not really pounding out the keyboard, the keys on the keyboard anymo…
AI assessment note: “You start off incredibly technical... then you get into a hiring phase where you're meeting demand”
