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It's probably like a year or so ago, I met you at startup camp, we were just talking,

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and the prospect of sort of starting up an open source business, I think to a lot of developers

3
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or whoever, is a little scary because you're kind of like, "Well, I've got to eat, right?

4
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I want to be hungry."

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Right.

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And so, I mean, how...

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You do live longer, but it's just going to hurt.

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That's right.

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How did you figure out, like, bootstrapping up a business?

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I mean, are you still, like, are you still biting your nails all the time?

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Like, am I going to be able to pay the bills?

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I like the implication.

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I have figured it out.

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Well, at least, how do you let yourself work on your own?

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I mean, how have you not switched over to, like, you know, a bigger teat to, like, get

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the money off of?

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For me, it's not much of a choice.

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I was a very successful sysadmin in that I very much did the job.

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Right.

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I was very not successful in that I never cared about the companies I worked for.

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I found a way to be interested in the technical problems of solving other people's technical

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problems.

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Right.

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I never cared whether it, whether they liked me or whether it worked, you know.

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It worked for them technically, but I wasn't really worried about much else.

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So, I can't go back and be a sysadmin for a company again.

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I know I can't do that.

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I'm too fond of the freedom I get from running my own stuff.

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Right, right, right.

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I wasn't a very good consultant.

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I'm not that concerned about, like, it's just, I found it hard to go into companies and sell

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something that didn't mean anything to me.

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It's just a repetition of a problem.

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It was easy to make money, but it's not easy to do something that you care about all the

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time.

36
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So, for me, it was find a way to make the tools in this space not suck.

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Right.

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Because two years ago, the tools in this space did suck.

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And I think Puppet, I think it sucks less than any of the software out there.

40
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But I'm not going to say it doesn't suck.

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I'm not going to say that you can download it and, man, it'll be awesome.

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It probably will be compared to SSH and the For loop, like most people are doing right

43
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now.

44
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Sure.

45
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And I go, God, that Luke guy.

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He just, so, but I want it to suck less.

47
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And so either it has to suck less or I was going to change fields.

48
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And I looked into, you know, going to law school or, you know, is there another field

49
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that I can be interested in?

50
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And eventually I said, there's too much opportunity.

51
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There's too much money being wasted, being thrown away to not be able to make money in

52
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this space.

53
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There's too many good ideas floating around.

54
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There are too many ways to think about the problem differently that we can come up with

55
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a good solution.

56
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And I've got a lot of those ideas and no one is implementing them.

57
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I've been trying to get these ideas away for years.

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I've been trying to say, you should do this.

59
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People should do this.

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People should.

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And everyone goes, you're crazy.

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So either I'm crazy or they don't know what they're talking about.

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And I figure I'll make the dice throw and we'll see what happens.

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Either I'm wrong and I am crazy and no one's going to pay me or I'm right and I'm going

65
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to make a stink little money or something or not.

66
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Well, you already have several customers who rush.

67
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I assume that the checks of cash and everything.

68
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Right, exactly.

69
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So I've got six or seven customers.

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Some of whom are pretty, some of whom are, I mean, most of my customers, I think at this

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point I've got two customers most people wouldn't have heard of.

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Right.

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But of the six or seven customers, almost everyone else would have heard of almost all of them.

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So, and one of them, you know, some of them are very prominent in the community.

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Stanford University is a big customer but also a big member of the community.

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They, one of their guys maintains the style guide.

77
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One of their guys is on the docs team.

78
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So, you know, they, they are big and they're very happy users.

79
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I'm not really concerned about the business because I can always go back and be a consultant

80
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for a little while and be a developer.

81
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Or I can always go back to school.

82
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I mean, what's, what's the worst that's going to happen, right?

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Right, right.

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I expend a couple months unhappy.

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I borrow a little more money from somebody and then I go, well, that didn't work.

86
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I guess I'm going to law school or something, you know?

87
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Right, right.

88
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So, but I'm not a frightened person.

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I'm, I'm, I'm, I'm relatively risk friendly.

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I don't have children.

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I don't have significant medical problems.

92
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I don't have, um, something that keeps me from, from being able to embrace risk.

93
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Um, in five years, I may feel differently.

94
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In five years, I'm going to be a little less risk friendly probably.

95
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Yeah.

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I mean, I, I ask people this sort of question, like how did you get your business bootstrapped

97
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a lot?

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And, and it's interesting that those two things that you, that you mentioned there, I mean,

99
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are the things that kind of dance around in the back as far as if you have a family

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to support or if, or if you for some reason need really good health insurance and your spouse.

101
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And you live in the U S right.

102
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Cause if you're in Canada and you're like, right, right.

103
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Health insurance doesn't come.

104
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And then, I mean, I got it.

105
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I mean, I, and it drives me crazy cause I'm kind of in this boat as well.

106
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Like working for a small firm.

107
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It's just like, just if you're not lucky enough to have a spouse who has fantastic insurance,

108
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it's like very difficult to, uh, it's kind of scary to jump off into that.

109
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Like I'm going to pay for my own crazy insurance or not have insurance.

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And you start having these weird discussions with the doctors you do talk to because you don't

111
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want to write anything down because then it's like, it's like your credit score.

112
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Right, right.

113
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Well, it says here, you're defaulted on your knee.

114
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What's up with that?

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That kind of stuff affects how friendly you are to risk.

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Right.

117
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But as long as, you know, you really just assess it and say, well, what happens?

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What's the worst that's going to happen?

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And to me, that's the best, the best question you can ask yourself when looking at starting

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a company.

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And if you're a developer today, if you're a successful developer in an open source project,

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you're doing good work.

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Right.

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You've got a lot of ideas that you think can do well.

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What is the absolute worst that's going to happen?

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You try it for a while and you go into debt a car.

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Right.

128
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I mean, come on, right?

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Sure.

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You're willing to debt a BMW.

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Right.

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Are you willing to buy a BMW?

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Are you willing to consider taking a loan out to buy a car like this?

134
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If you are, then why not at the same time consider that you, again, this is the worst case scenario.

135
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Right.

136
00:05:08,860 --> 00:05:10,860
You bought a BMW without getting the BMW.

137
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You just owe sort of 50, 60, 70,000 over five years or something.

138
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Right.

139
00:05:14,860 --> 00:05:15,860
I mean, do you think you can handle that?

140
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Right, right.

141
00:05:16,860 --> 00:05:18,860
Can you find somebody who can help you mitigate the cost of that debt?

142
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So, probably, maybe not an angel investor, but a father-in-law or an uncle or something.

143
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A friend or family investor, right?

144
00:05:24,860 --> 00:05:25,860
Right.

145
00:05:25,860 --> 00:05:28,860
And a lot of times you just say, you know, look, you know I'm good for the debt.

146
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You know I'm going to pay it off eventually.

147
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You know if this doesn't work out, I can get a good job as a developer again.

148
00:05:32,860 --> 00:05:33,860
Right.

149
00:05:33,860 --> 00:05:39,860
And I'll pay you 500 bucks or 700 bucks a month once they go back to my six figure a year job as a developer if it doesn't work out.

150
00:05:39,860 --> 00:05:42,860
And if it does work out, eh, slip a little something your way.

151
00:05:42,860 --> 00:05:47,860
So, it's a pretty easy risk scenario for your friends who do have plenty of money or even some money.

152
00:05:47,860 --> 00:05:49,860
And plenty of money doesn't have to be a lot.

153
00:05:49,860 --> 00:05:53,860
You know, I borrowed some money from family who are not at all rich, but it was one client money.

154
00:05:53,860 --> 00:05:54,860
Right.

155
00:05:54,860 --> 00:05:56,860
If I get one client, then I can pay you back.

156
00:05:56,860 --> 00:05:57,860
Right.

157
00:05:57,860 --> 00:06:00,860
And if I don't get one client, I'm going to go get a job.

158
00:06:00,860 --> 00:06:05,860
So, I'm lucky in that my project, I picked a relatively small project that I knew very well.

159
00:06:05,860 --> 00:06:09,860
And it wasn't a question of two years of development or three years of development.

160
00:06:09,860 --> 00:06:15,860
But really, if you're just one, if it's just you and you're thinking of picking a project that's going to take three years to figure out,

161
00:06:15,860 --> 00:06:18,860
I would question whether that's a good idea at this point.

162
00:06:18,860 --> 00:06:27,860
And frankly, at this point, any project that takes three years to get started is such a big project at this point that it probably should be broken into multiple pieces.

163
00:06:27,860 --> 00:06:35,860
And even now, I can look back and say, I should have written a smaller project to start with and released that sooner and iterated more often.

164
00:06:35,860 --> 00:06:37,860
And ten months was my Skunk Works time.

165
00:06:37,860 --> 00:06:44,860
It would take me ten months to go from a simplistic prototype that was maybe a couple of other lines of code to a functional system that I was willing to talk about.

166
00:06:44,860 --> 00:06:45,860
Right.

167
00:06:45,860 --> 00:06:47,860
And I feel like that was too long of a Skunk Works.

168
00:06:47,860 --> 00:06:49,860
And that's nothing, right?

169
00:06:49,860 --> 00:06:50,860
Yeah, yeah.

170
00:06:50,860 --> 00:06:51,860
Absolutely.

171
00:06:51,860 --> 00:06:55,860
You know, if you can't get something that people can see, and everyone's used to this in the web space, right?

172
00:06:55,860 --> 00:06:59,860
Everyone says, you know, we're used to talking about Web 2.0 and fast deployments and iterating.

173
00:06:59,860 --> 00:07:00,860
But why not everything else?

174
00:07:00,860 --> 00:07:06,860
It's true that you want to, both like you were saying, as far as the money flow you have and also the code flow is to have small stepping stones.

175
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Right.

176
00:07:07,860 --> 00:07:09,860
Rather than have to make these giant leaps.

177
00:07:09,860 --> 00:07:15,860
Because it's a lot easier to recover from error or redirect yourself as needed if you have these small iterative things.

178
00:07:15,860 --> 00:07:21,860
Rather than the three-year plan, which when you're done with it may be irrelevant at that point, right?

179
00:07:21,860 --> 00:07:22,860
And I've come up with a bunch of these.

180
00:07:22,860 --> 00:07:25,860
I've periodically said, you know, the website doesn't have any developer documentation.

181
00:07:25,860 --> 00:07:27,860
It doesn't have any timelines.

182
00:07:27,860 --> 00:07:29,860
It doesn't have, you know, blah.

183
00:07:29,860 --> 00:07:31,860
And so I'll go, all right, all right.

184
00:07:31,860 --> 00:07:33,860
I'll wait until enough complaints about this happen.

185
00:07:33,860 --> 00:07:35,860
And I go and I'll spend a week working at all of this.

186
00:07:35,860 --> 00:07:37,860
And make a roadmap or something?

187
00:07:37,860 --> 00:07:38,860
Yeah.

188
00:07:38,860 --> 00:07:43,860
And I can go and I can look at the view logs and it's like, four people have looked at that document in the last two years.

189
00:07:43,860 --> 00:07:45,860
Okay, well, clearly.

190
00:07:45,860 --> 00:07:46,860
Right, right.

191
00:07:46,860 --> 00:07:47,860
People complain about it.

192
00:07:47,860 --> 00:07:48,860
You produce it and they don't use it anyway.

193
00:07:48,860 --> 00:07:49,860
Yeah.

194
00:07:49,860 --> 00:07:54,860
So at this point, I've got to the point where for a lot of these things, I roughly know what I'm going to do in the next six months.

195
00:07:54,860 --> 00:07:55,860
I know exactly what I'm going to do in the next six months.

196
00:07:55,860 --> 00:07:57,860
I roughly know what I'm going to do in the next year or two.

197
00:07:57,860 --> 00:08:01,860
And I will answer your questions and I will produce simple documentation.

198
00:08:01,860 --> 00:08:05,860
But otherwise, I'm going to play it by ear because I'm going to lie to you.

199
00:08:05,860 --> 00:08:08,860
If I'm going to tell you I know where I'm going to be in a year, I'm not telling the truth.

200
00:08:08,860 --> 00:08:09,860
Right, right.

201
00:08:09,860 --> 00:08:12,860
Not because I don't think that's the truth, but because it's not the truth.

202
00:08:12,860 --> 00:08:14,860
You just can't predict or control that far into the future, right?

203
00:08:14,860 --> 00:08:15,860
Well, great.

204
00:08:15,860 --> 00:08:16,860
Well, thanks for spending all this time.

205
00:08:16,860 --> 00:08:17,860
It was great.

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00:08:17,860 --> 00:08:17,860
Thank you.