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.
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Answered produced feed
D 5 · C 4 · P 4 · Cm 3 4.15
Q Wait, how did you know that, Mike? How did you know you were de-risking?
A Well, I mean, more and more people were signing up every day. They seem to love what we're doing. You know, they're screaming about how great it is versus, you know, the incumbents. Uh, so, so, you know, for, for all those reasons and more and, and growth, like sustained high growth, right? So it's like, huh, it doesn't seem like, you know, the, the, the, like things are, are stopping. So, um, so, so for, for all those reasons, but the real thing I'll get at, which, which changed my mind was, um, Um, so you're de-risking those things, but there was still one major problem we had. We got to about a hundred people and I had, you know, tried to surround myself with the best folks I could. And until I hired like what I would call it was my first sort of real executive. Um, what I realized is I just didn't know what I was looking for before that. And, you know, it's just a learning curve. Sometimes it's an entrepreneur. And so, you know, then I hired that first executive and then I was like, okay, I'm addicted. I just need a bunch more of these. And, and by the way, now once you have that, the only thing really holding us back was capital. Uh, and so I had learned enough. We had been operating with a board, uh, you know, felt like, okay, the conditions are right for a few things. We've de-risked the opportunity. I feel like I, you know, have enough water under my keel to understand …
AI assessment note: “more and more people were signing up every day. They seem to love what we're doing.”
Partly produced feed
D 3 · C 5 · P 4 · Cm 4 4.00
Q getting very close with the Rackspace crew. Uh, Pat Matthews and Pat Condon and some of these guys were early investors in my first company. I remember them just casually mentioning how impressed they were with you, and I think some of them invested in FreshBooks as well, so I'm excited to chat with you. Give us, kind of tell us what FreshBooks does, and how do you make money?
A Yeah, so, uh, FreshBooks is, uh, Ridiculously easy to use invoicing and accounting software. So we, we help folks create and send professional looking invoices, uh, track expenses, ultimately just capture all those transactions that make it, you know, really filing your taxes and accounting at the end of the year, uh, easy. As I like to say, if you, if you invoice, you need fresh books. Um, what makes us a little different is that we're not built for everybody. Uh, so we're focused on folks who, uh, Um, you know, get paid for their time and expertise when serving other people. So we don't serve restaurants. We don't serve retail. Uh, we don't serve manufacturing. Um, really, really around client service based businesses, people who, uh, who, who serve others. And that lets us keep the product simple, available on all your devices, all that good stuff. So that, that's a bit about FreshBooks.
AI assessment note: “FreshBooks is, uh, Ridiculously easy to use invoicing and accounting software.”
Partly produced feed
D 3 · C 4 · P 3 · Cm 3 3.30
Q You, you earned a little bit of a, of a reputation of kind of the, kind of the anti VC, right? I think you bootstrapped for over a decade. Uh, tell us kind of how you think about raising capital, how much you've raised to date and what kind of quote broke your, your thinking, why decide to raise eventually. Yeah.
A Uh, as I like to say, uh, I was the poster boy for the anti VC movement for, for a long time. Uh, and, you know, I think as I'll walk you through my thought process, like, you know, there's some good reasons for that, and, and, uh, you know, decided to change my mind, which is the prerogative, uh, that I'm afforded. So, um, I guess when we got started out, um, well, there were a couple factors at play. Um, I knew that, uh, that venture folks knew I did not know. So it was not an even playing field with regards to, um, you know, building these businesses. And so I felt like I was, I was behind the learning curve there at the outset. So that was, that was something, but the core reason I didn't want to raise capital was because we really believed in customer service. And, uh, I was always afraid I would somehow show up at a board meeting one day. If we raise venture capital, people would tell me like, oh, you know, we're, we're outsourcing our service function. Now service is a cost center. And I don't see it that way at all, especially serving SMB. And, and so, by the way, great to follow the folks at Iraq space and, you know, big believers in service as well. And so, so that was the reason like, it was basically like fear. Uh, and as I started to tease through the fear and that the knowledge that I knew that I didn't know stuff I started to de-risk things in our business, so we…
AI assessment note: “the core reason I didn't want to raise capital was because we really believed”
Partly produced feed
D 3 · C 3 · P 3 · Cm 3 3.00
Q one question I was going to ask you, right, is, I mean, there's a lot of founders today that shared your same concerns about VC, right? So what they've done instead is they've just worked with some of these venture debt firms, and they're having some success doing it. I'm curious why you didn't go more down that road, route, or maybe you didn't, I just don't know about it.
A Um, I, I guess, um, Here's how I think about raising, uh, capital and equity is, is, um, like, if you're going to give up, say, 20% of your company, right, you're going to raise around, um, you know, if you can drive 20% More value. If you can grow the business by one, you're, you're neutral to good, right? Now you gotta be able to return the capital. So you actually need to increase the value more than say, 20% and that kind of thing. But, but, um, uh, I, you know, I think there's a great alignment. Actually, I'll say this. I got to a place where I felt like the board I had was wonderful, but you know, I kind of left board meetings like, geez, I didn't get what I wanted out of that. Um, I was ready for professional institutional money. I had some great operators like, you know, one, you know, the Both still on the board, you know, uh, and, uh, one of them runs an 80,000 person company, but, but couldn't tell me market data, like how much should we pay, you know, executive who does this or like those kinds of things with professional investors. Like, you know, they just give you those answers tickety boo because they're hiring those people all the time.
AI assessment note: “I was ready for professional institutional money.”
