1
00:00:00,000 --> 00:00:05,080
Hello everyone, welcome to the first episode of the CNS Podcast.

2
00:00:05,080 --> 00:00:07,480
Our guest today is David Brown.

3
00:00:07,480 --> 00:00:12,960
He is an investor, an author, and founder of the global accelerator Techstars.

4
00:00:12,960 --> 00:00:16,800
Everybody's got advice for you for how to make it as an entrepreneur these days.

5
00:00:16,800 --> 00:00:22,760
David's accelerator Techstars has invested in over 4,000 startup companies, including

6
00:00:22,760 --> 00:00:26,680
unicorns such as Sendgrid, Twilio, and Uber.

7
00:00:26,680 --> 00:00:31,160
What does he think it actually takes to be a successful entrepreneur?

8
00:00:31,160 --> 00:00:37,200
Today we will discuss how David's first company became a success with $100, common pitfalls

9
00:00:37,200 --> 00:00:42,000
of entrepreneurs, why it's better not to have a plan for the future, the difference

10
00:00:42,000 --> 00:00:46,400
between arrogance and self-confidence, and much more.

11
00:00:46,400 --> 00:00:58,480
Thanks for listening.

12
00:00:58,480 --> 00:01:03,400
You've participated in a lot of different ventures over your lifetime, and I'm curious

13
00:01:03,400 --> 00:01:07,840
into how you would say your passion's kind of connected into each different one that

14
00:01:07,840 --> 00:01:08,840
you've done.

15
00:01:08,840 --> 00:01:12,180
I mean, I feel that it's always connected, right?

16
00:01:12,180 --> 00:01:18,120
Because you spend so much of your time at work that if you're not passionate about what

17
00:01:18,120 --> 00:01:20,920
you do, you kind of don't have a great life.

18
00:01:20,920 --> 00:01:23,880
You better find a different line of work.

19
00:01:23,880 --> 00:01:27,700
And so to me, they're all massively interconnected.

20
00:01:27,700 --> 00:01:29,800
So first you had pinpoint technologies, right?

21
00:01:29,800 --> 00:01:31,200
Yeah, that was my first startup.

22
00:01:31,200 --> 00:01:37,240
I started that pretty soon after college, a long, long time ago.

23
00:01:37,240 --> 00:01:40,200
And what was that one that kind of called to you?

24
00:01:40,200 --> 00:01:46,120
It was funny, right, because I actually got a job out of college working for an ambulance

25
00:01:46,120 --> 00:01:48,960
company, and I was basically the IT guy.

26
00:01:48,960 --> 00:01:52,880
They didn't use the CTO title back then.

27
00:01:52,880 --> 00:01:56,700
I don't even remember what it was, but some equivalent.

28
00:01:56,700 --> 00:02:02,320
And so I was working for somebody else, and I had another guy there with me, also named

29
00:02:02,320 --> 00:02:04,800
David.

30
00:02:04,800 --> 00:02:13,560
We were basically both the IT guys, and we created the software to help run this ambulance

31
00:02:13,560 --> 00:02:14,920
company.

32
00:02:14,920 --> 00:02:20,440
And we thought, wouldn't it be cool to just sell the software to a bunch of other ambulance

33
00:02:20,440 --> 00:02:25,560
companies instead of running the service, which is what our boss did?

34
00:02:25,560 --> 00:02:31,000
And we approached him about, hey, could we create a branch, a division that sold the

35
00:02:31,000 --> 00:02:32,000
software?

36
00:02:32,000 --> 00:02:34,200
And he wasn't interested.

37
00:02:34,200 --> 00:02:37,520
And so we said, well, we'd like to go do it on our own.

38
00:02:37,520 --> 00:02:43,680
And miraculously, with his support, we went off and created our own software and launched

39
00:02:43,680 --> 00:02:45,760
our first business that way.

40
00:02:45,760 --> 00:02:48,320
And that was Pinpoint.

41
00:02:48,320 --> 00:02:49,320
That was Pinpoint.

42
00:02:49,320 --> 00:02:51,240
That was called Pinpoint Technologies.

43
00:02:51,240 --> 00:02:53,200
And it was just straight after college?

44
00:02:53,200 --> 00:02:58,840
And it was probably my mid-20s, mid to late 20s, because I graduated college.

45
00:02:58,840 --> 00:03:03,520
I worked for this ambulance service as the IT guy for a couple of years.

46
00:03:03,520 --> 00:03:05,560
I met my co-founder, David.

47
00:03:05,560 --> 00:03:07,160
We plotted a little bit.

48
00:03:07,160 --> 00:03:10,160
And so it was something.

49
00:03:10,160 --> 00:03:12,320
A little bit of plotting, scheming, and the plot stuff.

50
00:03:12,320 --> 00:03:13,880
We had a day job with the boss.

51
00:03:13,880 --> 00:03:14,880
Yeah, you had to do it on your own.

52
00:03:14,880 --> 00:03:20,520
And we wanted to basically take the idea that we were doing for work and go create a company

53
00:03:20,520 --> 00:03:21,520
around it.

54
00:03:21,520 --> 00:03:25,480
I think we were mindful that maybe there was some IP issues.

55
00:03:25,480 --> 00:03:32,960
We wanted to leave on good terms with John or do it with John, our boss.

56
00:03:32,960 --> 00:03:38,040
And so anyway, we worked that out and then started a software company.

57
00:03:38,040 --> 00:03:44,760
We didn't know anything about what we were doing in our 20s, figuring things out as we

58
00:03:44,760 --> 00:03:45,760
went.

59
00:03:45,760 --> 00:03:49,320
How did you know that the co-founder was the right one?

60
00:03:49,320 --> 00:03:53,440
Speaking of relationships and friendships, what was different about it?

61
00:03:53,440 --> 00:03:59,520
So it's an interesting question because the co-founder relationship I now know is the

62
00:03:59,520 --> 00:04:02,480
most important part to get right.

63
00:04:02,480 --> 00:04:04,640
And David and I were best friends.

64
00:04:04,640 --> 00:04:06,400
We're best men at each other's wedding.

65
00:04:06,400 --> 00:04:10,240
We've known each other for, God, that was the early 90s.

66
00:04:10,240 --> 00:04:11,240
So what's that?

67
00:04:11,240 --> 00:04:12,240
That's 34 years.

68
00:04:12,240 --> 00:04:13,240
34 years.

69
00:04:13,240 --> 00:04:14,240
34 years ago.

70
00:04:14,240 --> 00:04:16,240
And we're still great friends.

71
00:04:16,240 --> 00:04:22,320
Go to lunch every week.

72
00:04:22,320 --> 00:04:23,680
And so it worked out.

73
00:04:23,680 --> 00:04:26,960
And so I don't know that we were smart about it.

74
00:04:26,960 --> 00:04:28,800
We got lucky.

75
00:04:28,800 --> 00:04:34,440
We worked together for this guy, John, for a while before branching out.

76
00:04:34,440 --> 00:04:37,880
And we were roommates for a while.

77
00:04:37,880 --> 00:04:43,200
And we didn't really think that John always got things right.

78
00:04:43,200 --> 00:04:45,720
And we had ideas of how to do our own business.

79
00:04:45,720 --> 00:04:53,600
And so I think we became partners in crime, trying to figure that out, scheming and coming

80
00:04:53,600 --> 00:04:54,600
up with ideas.

81
00:04:54,600 --> 00:04:56,000
It brought us closer together.

82
00:04:56,000 --> 00:04:57,120
Yeah, exactly.

83
00:04:57,120 --> 00:05:00,840
So I think in many ways, we were friends before we were business partners.

84
00:05:00,840 --> 00:05:05,160
There might be something to be said about friends where you build towards something

85
00:05:05,160 --> 00:05:08,280
together and how those friendships kind of add more to your life.

86
00:05:08,280 --> 00:05:09,840
Yeah, and deep friends, right?

87
00:05:09,840 --> 00:05:10,840
Because we were roommates.

88
00:05:10,840 --> 00:05:13,080
So we worked together.

89
00:05:13,080 --> 00:05:14,080
We had fun.

90
00:05:14,080 --> 00:05:16,680
We had the same personal circle.

91
00:05:16,680 --> 00:05:17,680
We had the same life.

92
00:05:17,680 --> 00:05:18,680
So there was no issue.

93
00:05:18,680 --> 00:05:19,680
Exactly.

94
00:05:19,680 --> 00:05:20,680
It's like, oh, you want to go do this together?

95
00:05:20,680 --> 00:05:21,680
We can do everything together.

96
00:05:21,680 --> 00:05:23,200
What's the difference?

97
00:05:23,200 --> 00:05:24,680
That's a great friend to have right there.

98
00:05:24,680 --> 00:05:27,080
I mean, I call him my work spouse.

99
00:05:27,080 --> 00:05:28,080
He doesn't like that.

100
00:05:28,080 --> 00:05:29,080
Oh, really?

101
00:05:29,080 --> 00:05:32,080
What does he say back to it?

102
00:05:32,080 --> 00:05:33,080
I don't know.

103
00:05:33,080 --> 00:05:34,080
I don't know what it sounds like to him.

104
00:05:34,080 --> 00:05:36,960
We each have our own spouses.

105
00:05:36,960 --> 00:05:44,880
But it's the closest thing to a permanent relationship other than sort of who you marry.

106
00:05:44,880 --> 00:05:49,120
And so very, very much been my work spouse my whole life.

107
00:05:49,120 --> 00:05:54,960
I'm always curious about the motivation factors that go into why people do things.

108
00:05:54,960 --> 00:06:00,720
And some entrepreneurs have this deep need to prove other people wrong or have this deep

109
00:06:00,720 --> 00:06:02,440
purpose that I knew since I was young.

110
00:06:02,440 --> 00:06:05,840
What was kind of that thing for you when you were in your early 20s and you're sitting

111
00:06:05,840 --> 00:06:07,880
there like, oh, I should do this thing.

112
00:06:07,880 --> 00:06:10,920
So it wasn't money, first of all, for sure.

113
00:06:10,920 --> 00:06:12,520
That was usually not for work.

114
00:06:12,520 --> 00:06:16,400
No, but I think a lot of entrepreneurs sort of have this image that you're going to become

115
00:06:16,400 --> 00:06:17,400
rich.

116
00:06:17,400 --> 00:06:20,280
But when you start off with that notion, you almost never do.

117
00:06:20,280 --> 00:06:21,880
So it certainly wasn't that for us.

118
00:06:21,880 --> 00:06:26,200
And I think it was a desire to create something out of nothing.

119
00:06:26,200 --> 00:06:31,480
It was sort of the creativity of it and the difficulty of like, nothing is there in this

120
00:06:31,480 --> 00:06:33,200
space.

121
00:06:33,200 --> 00:06:36,240
And we think that problem should be solved.

122
00:06:36,240 --> 00:06:40,320
And it's not just as easy as writing some code and creating a product.

123
00:06:40,320 --> 00:06:44,760
You have to get customers and learn sales and incorporate a business and hire employees

124
00:06:44,760 --> 00:06:47,320
and pick a headquarters, get an office.

125
00:06:47,320 --> 00:06:48,320
Pay taxes, whatever.

126
00:06:48,320 --> 00:06:49,320
Pay taxes.

127
00:06:49,320 --> 00:06:51,800
All kinds of crazy things that you got to figure out as you go.

128
00:06:51,800 --> 00:06:54,880
And it was just a whirlwind of figuring that out.

129
00:06:54,880 --> 00:06:55,880
And it was a blast.

130
00:06:55,880 --> 00:06:58,160
The figuring it out was the fun part.

131
00:06:58,160 --> 00:07:03,440
And what did that creation aspect where you have nothing and you create something, what

132
00:07:03,440 --> 00:07:08,160
did that do for you internally in terms of like an emotional connection to it?

133
00:07:08,160 --> 00:07:09,160
It feels great, right?

134
00:07:09,160 --> 00:07:12,740
Like it gives you, it gives your life purpose and meaning.

135
00:07:12,740 --> 00:07:17,080
And it turns out that that business, and we can get to this, but that business and all

136
00:07:17,080 --> 00:07:20,160
my other businesses that succeeded had purpose.

137
00:07:20,160 --> 00:07:22,380
And the ones that didn't have purpose failed.

138
00:07:22,380 --> 00:07:29,180
And so, the software we were creating at Pinpoint was to dispatch ambulance and save lives.

139
00:07:29,180 --> 00:07:33,640
And so you felt like you were making the world a better place as a result of what your business

140
00:07:33,640 --> 00:07:34,640
did.

141
00:07:34,640 --> 00:07:38,920
And it's an amazing feeling to have that purpose.

142
00:07:38,920 --> 00:07:45,100
It allows you to sort of get up in the morning and work hard without it feeling like any

143
00:07:45,100 --> 00:07:46,520
effort whatsoever.

144
00:07:46,520 --> 00:07:49,680
Without it feeling like you're working 80 hours a week.

145
00:07:49,680 --> 00:07:50,680
Totally.

146
00:07:50,680 --> 00:07:53,200
You're just working all the time, but it's a blast.

147
00:07:53,200 --> 00:07:55,040
It's a great time.

148
00:07:55,040 --> 00:07:58,600
There's some saying that I heard that, you know, an entrepreneur that's passionate about

149
00:07:58,600 --> 00:08:03,200
what they do because they're so focused on their business, they forget to eat or poop.

150
00:08:03,200 --> 00:08:07,120
They're so focused that that's what you do all day and you get to the end of the day

151
00:08:07,120 --> 00:08:08,120
and you're like, oh.

152
00:08:08,120 --> 00:08:09,120
Good day.

153
00:08:09,120 --> 00:08:11,640
I forgot to eat, but it was still good.

154
00:08:11,640 --> 00:08:14,880
You talk about meaning and purpose, which I think is quite interesting.

155
00:08:14,880 --> 00:08:18,720
I don't know if you've ever read Victor Frankl's Man Search for Meaning.

156
00:08:18,720 --> 00:08:19,720
I haven't.

157
00:08:19,720 --> 00:08:20,720
Great book.

158
00:08:20,720 --> 00:08:21,720
I love it.

159
00:08:21,720 --> 00:08:25,240
So he talks about the concentration camps and one of the differences between people

160
00:08:25,240 --> 00:08:27,160
who made it out and people who didn't.

161
00:08:27,160 --> 00:08:32,600
And one of those things was this idea of a bigger meaning or a bigger purpose, a bigger

162
00:08:32,600 --> 00:08:37,400
life accomplishment that they still had hope for regardless of whether they were going

163
00:08:37,400 --> 00:08:38,400
to make it out or not.

164
00:08:38,400 --> 00:08:40,200
They had no idea.

165
00:08:40,200 --> 00:08:45,000
And the ones that would lose hope were the ones that didn't have that larger thing to

166
00:08:45,000 --> 00:08:46,000
work towards.

167
00:08:46,000 --> 00:08:47,600
So it might be a similar thing in business.

168
00:08:47,600 --> 00:08:48,600
Yeah.

169
00:08:48,600 --> 00:08:52,240
I mean, obviously I can't compare anything to being in a concentration camp, but I do

170
00:08:52,240 --> 00:08:58,560
think it's true that if you give up hope on your startup, it's going to fail.

171
00:08:58,560 --> 00:09:03,400
Once you start getting that feeling that maybe it's not going to work, it's not going to

172
00:09:03,400 --> 00:09:04,400
work.

173
00:09:04,400 --> 00:09:05,400
I agree.

174
00:09:05,400 --> 00:09:11,200
But hope is intricately tied to that other purpose that isn't the money or the success.

175
00:09:11,200 --> 00:09:15,400
It has to be like, oh, I'm actively going out and helping these people with the ambulance

176
00:09:15,400 --> 00:09:18,000
business say or whatever business you're making.

177
00:09:18,000 --> 00:09:19,000
Yeah.

178
00:09:19,000 --> 00:09:24,120
You're saving lives is what the purpose was at that first startup at Pinpoint and at Tech

179
00:09:24,120 --> 00:09:26,840
Stars later on, it was about helping entrepreneurs succeed.

180
00:09:26,840 --> 00:09:32,280
And when you had that purpose, when you could define, articulate that purpose in easy words

181
00:09:32,280 --> 00:09:37,280
and that not only you, but everybody in the company could rally around it, it made it

182
00:09:37,280 --> 00:09:39,320
a lot easier to go to work every day.

183
00:09:39,320 --> 00:09:43,000
I can feel that as well, where it's like you have some bigger purpose to work towards.

184
00:09:43,000 --> 00:09:44,480
It makes work so much easier.

185
00:09:44,480 --> 00:09:50,800
And the company that failed was basically an early social media app, which was probably

186
00:09:50,800 --> 00:09:52,000
ahead of its time.

187
00:09:52,000 --> 00:09:55,800
But we never really felt like we had purpose.

188
00:09:55,800 --> 00:09:58,480
We wanted to do the entrepreneur thing again.

189
00:09:58,480 --> 00:10:00,440
We felt like we were successful.

190
00:10:00,440 --> 00:10:02,440
Like, oh, I know what I'm doing.

191
00:10:02,440 --> 00:10:05,200
I know what I'm doing now.

192
00:10:05,200 --> 00:10:10,800
And it wasn't, you know, I don't know why we picked that idea, but we weren't passionate

193
00:10:10,800 --> 00:10:11,800
about the idea.

194
00:10:11,800 --> 00:10:14,120
The idea didn't give our life meaning and purpose.

195
00:10:14,120 --> 00:10:17,040
And it made it a lot harder when things got tough.

196
00:10:17,040 --> 00:10:21,720
You know, when things get tough in the ambulance business, you push through because you're

197
00:10:21,720 --> 00:10:22,720
saving lives.

198
00:10:22,720 --> 00:10:23,720
Okay.

199
00:10:23,720 --> 00:10:27,120
You know, that was a sucky day, but I'm going to push through and do it.

200
00:10:27,120 --> 00:10:33,640
But if nobody gets to use your social media app that nobody's using, you don't care all

201
00:10:33,640 --> 00:10:34,640
that much.

202
00:10:34,640 --> 00:10:35,640
You don't really care.

203
00:10:35,640 --> 00:10:36,640
Yeah.

204
00:10:36,640 --> 00:10:37,640
What am I offering?

205
00:10:37,640 --> 00:10:38,640
What am I offering?

206
00:10:38,640 --> 00:10:39,640
I might as well give up.

207
00:10:39,640 --> 00:10:40,640
I'm working a lot of hours.

208
00:10:40,640 --> 00:10:41,640
I'm not making any money.

209
00:10:41,640 --> 00:10:42,640
I'm losing hope.

210
00:10:42,640 --> 00:10:43,940
It's too easy to give up.

211
00:10:43,940 --> 00:10:48,840
And that's very important is making it impossible to give up in a startup.

212
00:10:48,840 --> 00:10:53,360
I want to touch on tech stars in a bit, but I also want to dive deeper into those younger

213
00:10:53,360 --> 00:10:55,000
years when you're starting out.

214
00:10:55,000 --> 00:11:00,800
You didn't really get into this relationships until later on in your life, right?

215
00:11:00,800 --> 00:11:06,400
What was kind of dating and having romantic relationships like for you in those younger

216
00:11:06,400 --> 00:11:07,400
years?

217
00:11:07,400 --> 00:11:09,360
It was, you know, it was sparse, right?

218
00:11:09,360 --> 00:11:12,400
I was really, really focused on the business.

219
00:11:12,400 --> 00:11:16,620
I mean, I dated, I had girlfriends going back to before I even moved to the US.

220
00:11:16,620 --> 00:11:23,920
So before this first startup, I was born and raised in Canada and I dated even for a couple

221
00:11:23,920 --> 00:11:27,880
years.

222
00:11:27,880 --> 00:11:37,320
So I think it was a normal life in that regard, but it was few and far between because if

223
00:11:37,320 --> 00:11:41,960
you weren't dating anybody, you're so focused on the business, you're not meeting anybody.

224
00:11:41,960 --> 00:11:42,960
Exactly.

225
00:11:42,960 --> 00:11:43,960
You're not going outside.

226
00:11:43,960 --> 00:11:44,960
Exactly.

227
00:11:44,960 --> 00:11:45,960
You're sitting inside all the time.

228
00:11:45,960 --> 00:11:50,420
Yeah, but I do think like, and some of this I wish I could have applied to my life going

229
00:11:50,420 --> 00:11:56,040
back, but I do think that having that balance and certainly I've been married a long, long

230
00:11:56,040 --> 00:11:58,960
time now since that very first startup.

231
00:11:58,960 --> 00:12:04,560
And I think, you know, having a different life outside of work, having a personal life,

232
00:12:04,560 --> 00:12:11,760
having a significant other kids, whatever your thing is, is really helpful to balance

233
00:12:11,760 --> 00:12:17,680
the, I always described it as work was chaos, ups and downs and craziness and customers

234
00:12:17,680 --> 00:12:22,720
coming and going and highs and lows and you know, and then at home, everything was like

235
00:12:22,720 --> 00:12:23,720
stable, right?

236
00:12:23,720 --> 00:12:26,800
I've lived in the same house for 30 years.

237
00:12:26,800 --> 00:12:31,320
I've had the same wife for 25 years, whatever.

238
00:12:31,320 --> 00:12:36,000
Same house, same, I used to say same house, same wife, same kids, same dog.

239
00:12:36,000 --> 00:12:37,000
Dog died.

240
00:12:37,000 --> 00:12:38,000
Dog died.

241
00:12:38,000 --> 00:12:43,200
But it was very grounding to balance out the chaos of running a startup with having a more

242
00:12:43,200 --> 00:12:45,560
stable personal life at home.

243
00:12:45,560 --> 00:12:46,560
That's interesting.

244
00:12:46,560 --> 00:12:51,040
I think a lot of people push towards a more balanced approach to entrepreneurship, like

245
00:12:51,040 --> 00:12:55,600
you're saying, and then some people go towards the, oh, you don't have really the bandwidth

246
00:12:55,600 --> 00:12:57,000
to deal with a relationship.

247
00:12:57,000 --> 00:12:59,160
Yeah, I don't believe that.

248
00:12:59,160 --> 00:13:01,760
I think that's self-imposed.

249
00:13:01,760 --> 00:13:06,200
There are lots of entrepreneurs that find time to do that and it just took me longer.

250
00:13:06,200 --> 00:13:10,920
I mean, that was me from when I started Pinpoint to when I sold Pinpoint.

251
00:13:10,920 --> 00:13:13,120
So that was about six years.

252
00:13:13,120 --> 00:13:20,360
Just all in giving 100% every day, day and night, roommates with David, working on the

253
00:13:20,360 --> 00:13:22,480
business, trying to grow it.

254
00:13:22,480 --> 00:13:27,400
There was barely time for a social life.

255
00:13:27,400 --> 00:13:29,520
But was that necessary to make the business successful?

256
00:13:29,520 --> 00:13:30,520
I don't believe that.

257
00:13:30,520 --> 00:13:32,720
I think it would have gone big anyways.

258
00:13:32,720 --> 00:13:33,720
Yeah.

259
00:13:33,720 --> 00:13:34,720
Yeah.

260
00:13:34,720 --> 00:13:38,600
Because I think that when you balance your life with a relationship or sleep or whatever

261
00:13:38,600 --> 00:13:42,720
it is, right, that I think you make better business decisions at work.

262
00:13:42,720 --> 00:13:47,680
And so even if you're not spending 16 hours a day at the office and you're only spending

263
00:13:47,680 --> 00:13:54,960
10 or 12, right, that you still can accomplish just as much maybe more because you're well

264
00:13:54,960 --> 00:13:59,840
rested, you're recharging, you're sharper, you're not making as many bad decisions.

265
00:13:59,840 --> 00:14:00,840
Yeah.

266
00:14:00,840 --> 00:14:05,120
And that's why one of the things we're focusing on is creating a more synergistic life because

267
00:14:05,120 --> 00:14:10,880
I don't know if you go online very much often, but a lot of the narrative online with entrepreneurship,

268
00:14:10,880 --> 00:14:13,960
there's a lot of entrepreneurship influencers and stuff.

269
00:14:13,960 --> 00:14:18,920
And they're always pushing this narrative of, oh, you have to be on the grind 24-7 and

270
00:14:18,920 --> 00:14:20,680
you have to give up everything else.

271
00:14:20,680 --> 00:14:21,860
I don't think that's true.

272
00:14:21,860 --> 00:14:24,360
But I think when you're on, you have to be on, right?

273
00:14:24,360 --> 00:14:28,340
So in other words, but give yourself permission to be off.

274
00:14:28,340 --> 00:14:32,420
So I disagree with those that say you have to be on 24-7 because I think when you're

275
00:14:32,420 --> 00:14:34,720
on 24-7, you're not as sharp.

276
00:14:34,720 --> 00:14:35,720
I agree.

277
00:14:35,720 --> 00:14:40,840
It's a true story, but it's the example I always give to prove that point is I have

278
00:14:40,840 --> 00:14:43,960
always slept nine hours a night, right?

279
00:14:43,960 --> 00:14:45,560
Ten hours on weekends, right?

280
00:14:45,560 --> 00:14:47,800
I love my sleep.

281
00:14:47,800 --> 00:14:50,280
And a lot of people say, how do you...

282
00:14:50,280 --> 00:14:53,040
People always used to say to me, how do you get so much done?

283
00:14:53,040 --> 00:14:54,040
Right?

284
00:14:54,040 --> 00:14:55,040
I'm good on email.

285
00:14:55,040 --> 00:14:56,040
I go to meetings.

286
00:14:56,040 --> 00:14:57,040
I'm running a business.

287
00:14:57,040 --> 00:15:02,640
I mean, I'm not doing that now, but I was.

288
00:15:02,640 --> 00:15:08,680
And I would say that because I was well rested, my brain was sharper.

289
00:15:08,680 --> 00:15:09,920
I made better decisions.

290
00:15:09,920 --> 00:15:11,680
I made fewer mistakes.

291
00:15:11,680 --> 00:15:14,520
I did less of the, oh, I don't know what to do about that problem.

292
00:15:14,520 --> 00:15:16,880
Let me set it aside and think about it later.

293
00:15:16,880 --> 00:15:19,920
And then you're always coming back to the same thing over and over again.

294
00:15:19,920 --> 00:15:20,920
You're on your back foot.

295
00:15:20,920 --> 00:15:21,920
What's that?

296
00:15:21,920 --> 00:15:22,920
You're running on your back foot, basically.

297
00:15:22,920 --> 00:15:23,920
Yeah, exactly.

298
00:15:23,920 --> 00:15:28,960
Whereas I was very, very good at problem come in, here's what I'm going to do.

299
00:15:28,960 --> 00:15:29,960
Move on.

300
00:15:29,960 --> 00:15:30,960
Next problem, please.

301
00:15:30,960 --> 00:15:31,960
Right?

302
00:15:31,960 --> 00:15:32,960
I was running at 100%.

303
00:15:32,960 --> 00:15:35,440
You're running at 100% when you're doing that.

304
00:15:35,440 --> 00:15:36,440
Same thing with email.

305
00:15:36,440 --> 00:15:39,720
I had hundreds of emails every day and I would just text them one at a time.

306
00:15:39,720 --> 00:15:40,880
What am I going to do with this one?

307
00:15:40,880 --> 00:15:41,880
Do it.

308
00:15:41,880 --> 00:15:42,880
What am I going to do with this one?

309
00:15:42,880 --> 00:15:43,880
Do it.

310
00:15:43,880 --> 00:15:44,880
What am I going to do with this one?

311
00:15:44,880 --> 00:15:45,880
Do it.

312
00:15:45,880 --> 00:15:48,360
Not, ugh, let me leave that in my inbox and then it accumulates and then you have 2000

313
00:15:48,360 --> 00:15:50,680
emails in your inbox that people are waiting for you on.

314
00:15:50,680 --> 00:15:51,680
That was never me.

315
00:15:51,680 --> 00:15:52,680
No, yeah, 100%.

316
00:15:52,680 --> 00:15:57,160
I think one of the most important things you mentioned right there is you were getting

317
00:15:57,160 --> 00:15:59,400
all your sleep and recharging.

318
00:15:59,400 --> 00:16:02,560
But when you were on, you were doing actions all the time.

319
00:16:02,560 --> 00:16:06,760
It wasn't just, oh, I'm working dilly dally or I'm stressing about this thing.

320
00:16:06,760 --> 00:16:08,440
It was, oh, I'm going to do the thing.

321
00:16:08,440 --> 00:16:09,440
Yeah, so that's what I'm saying.

322
00:16:09,440 --> 00:16:12,840
You don't have to be on 24-7, but when you're on, you have to be on.

323
00:16:12,840 --> 00:16:15,920
It's okay if that's 12 hours a day.

324
00:16:15,920 --> 00:16:20,480
I think then the option is you're recovering and you're sleeping and you actually get stuff

325
00:16:20,480 --> 00:16:23,560
done during those hours you're working or you can do it slower.

326
00:16:23,560 --> 00:16:25,240
I'll give you a counter example.

327
00:16:25,240 --> 00:16:29,360
To some extent, I had this when my kids were born and you had more sleepless nights.

328
00:16:29,360 --> 00:16:30,360
Yeah.

329
00:16:30,360 --> 00:16:35,160
And you show up at work the next day and your brain just felt like it's not firing in all

330
00:16:35,160 --> 00:16:36,160
cylinders.

331
00:16:36,160 --> 00:16:40,080
Decisions would come slower and emails would accumulate in the inbox.

332
00:16:40,080 --> 00:16:43,160
You couldn't get stuff done.

333
00:16:43,160 --> 00:16:48,800
And so training the brain to be really good at it, and part of that's getting enough sleep,

334
00:16:48,800 --> 00:16:50,000
but there's more to it than that.

335
00:16:50,000 --> 00:16:53,320
I think it makes it much more- Was there anything in particular you did to

336
00:16:53,320 --> 00:16:57,920
optimize your decision making or action ability other than sleep?

337
00:16:57,920 --> 00:17:00,200
Yeah.

338
00:17:00,200 --> 00:17:05,120
It took me years to learn this, but vacations off the grid was the only one that I would

339
00:17:05,120 --> 00:17:11,680
do where I would take a vacation where I was not constantly checking email.

340
00:17:11,680 --> 00:17:18,000
It's a different version of brain rest than sleep, but go to the beach, hang out with

341
00:17:18,000 --> 00:17:22,800
family, have a fun time, whatever you're doing, be present in the moment.

342
00:17:22,800 --> 00:17:29,000
So what if I come back to 3,000 emails in my inbox and I would go through them and I

343
00:17:29,000 --> 00:17:31,160
would answer every one.

344
00:17:31,160 --> 00:17:33,800
My wife will tell you, we always took our vacations.

345
00:17:33,800 --> 00:17:39,320
We came back on Saturday so that Sunday I could work all day on email before going back

346
00:17:39,320 --> 00:17:42,200
to the office on Monday, plow through them.

347
00:17:42,200 --> 00:17:44,560
So there was something there with fully disconnecting-

348
00:17:44,560 --> 00:17:49,040
There was something there to fully disconnecting and recharging the batteries.

349
00:17:49,040 --> 00:17:53,640
And I guess that's similar to sleep, but it's the same, it's similar in that you're resting

350
00:17:53,640 --> 00:17:55,640
your brain but in a different way.

351
00:17:55,640 --> 00:17:58,560
You're making your life about more than just your business.

352
00:17:58,560 --> 00:18:03,160
You're spending time with your family or your loved ones or in a beautiful place or whatever.

353
00:18:03,160 --> 00:18:04,480
You're actually having a life.

354
00:18:04,480 --> 00:18:05,480
You're having a life.

355
00:18:05,480 --> 00:18:06,480
You're having a good time.

356
00:18:06,480 --> 00:18:11,520
When you built all these businesses and you are the person we are today, what parts of

357
00:18:11,520 --> 00:18:16,960
your childhood do you think kind of influenced what you did throughout your life?

358
00:18:16,960 --> 00:18:21,160
I'm deep here, dude.

359
00:18:21,160 --> 00:18:30,280
I used to describe myself as the odd man, odd person out in my family because my father

360
00:18:30,280 --> 00:18:33,640
worked for the city, a very nine to five job.

361
00:18:33,640 --> 00:18:39,680
He worked there for 30 years or something for all my life until he retired.

362
00:18:39,680 --> 00:18:43,120
My mother was a social worker, same thing.

363
00:18:43,120 --> 00:18:48,400
She worked part time two days a week while she raised the kids and did that all her life,

364
00:18:48,400 --> 00:18:50,040
not all her life, but all my life.

365
00:18:50,040 --> 00:18:53,840
I never knew her to have a different role than that.

366
00:18:53,840 --> 00:19:03,960
My brother became a university professor and a real professor not like me.

367
00:19:03,960 --> 00:19:09,720
So he got his PhD and was in academia all his life.

368
00:19:09,720 --> 00:19:14,640
I was this crazy entrepreneur that went off and started business.

369
00:19:14,640 --> 00:19:20,360
I don't want to say a black sheep in the family in the sense that it's not that they looked

370
00:19:20,360 --> 00:19:24,160
down on me, but nobody understood anything about what I did.

371
00:19:24,160 --> 00:19:25,680
Do they have doubts?

372
00:19:25,680 --> 00:19:27,800
I don't think doubts is the right word.

373
00:19:27,800 --> 00:19:30,160
They didn't understand it at all.

374
00:19:30,160 --> 00:19:32,040
I worked crazy hours.

375
00:19:32,040 --> 00:19:35,120
I moved to the United States.

376
00:19:35,120 --> 00:19:41,960
I disappeared from the family as far as they were concerned, but I seem to be having fun.

377
00:19:41,960 --> 00:19:44,040
Whatever David's doing, he seems to be enjoying it.

378
00:19:44,040 --> 00:19:47,760
So good on him was my family's attitude to it.

379
00:19:47,760 --> 00:19:49,480
So during those years you didn't see them very often?

380
00:19:49,480 --> 00:19:50,480
No, no.

381
00:19:50,480 --> 00:19:51,480
I saw them.

382
00:19:51,480 --> 00:19:55,400
I'm from Canada, from Montreal, so it was a long flight.

383
00:19:55,400 --> 00:19:57,800
I was living in Florida in those early years.

384
00:19:57,800 --> 00:20:01,560
It was a long flight home, but I'd go home every year.

385
00:20:01,560 --> 00:20:04,560
We'd have Christmas together, normal family stuff.

386
00:20:04,560 --> 00:20:08,320
But it's not that I was hanging out with them every week.

387
00:20:08,320 --> 00:20:10,120
You were off in Florida, they were in Canada.

388
00:20:10,120 --> 00:20:11,320
Yeah, they'd come visit me.

389
00:20:11,320 --> 00:20:16,120
What was your relationship like with your brother?

390
00:20:16,120 --> 00:20:23,000
I have a sister too, and they are very close to each other.

391
00:20:23,000 --> 00:20:30,800
While we are civil is too weak a term, but while we communicate regularly, we have Zoom

392
00:20:30,800 --> 00:20:35,400
calls still every other month or something like that to catch up.

393
00:20:35,400 --> 00:20:40,840
I would not say I'm as close to either my brother or my sister as they are to each other.

394
00:20:40,840 --> 00:20:46,160
I've heard some advice where it goes you have two options when dealing with family, and

395
00:20:46,160 --> 00:20:50,400
one of them is you're either really close and you have a lot of conflict, or you're

396
00:20:50,400 --> 00:20:55,620
first of all and you get along and you're not the most close that you could be, but

397
00:20:55,620 --> 00:20:57,760
it's awesome and it's a great time.

398
00:20:57,760 --> 00:21:02,160
Yeah, I would say it's unfortunate.

399
00:21:02,160 --> 00:21:04,480
I don't know that I fit into either of those camps.

400
00:21:04,480 --> 00:21:09,760
It's unfortunate that I'm not closer to my siblings, but I feel like in some ways I don't

401
00:21:09,760 --> 00:21:11,240
have a lot in common with them.

402
00:21:11,240 --> 00:21:15,760
They live a very different life, and they probably view me the same way.

403
00:21:15,760 --> 00:21:19,920
Nothing wrong with that, and we still like each other and talk to each other and visit

404
00:21:19,920 --> 00:21:20,920
each other.

405
00:21:20,920 --> 00:21:22,880
So it's still peaceful.

406
00:21:22,880 --> 00:21:25,960
Yeah, it's always been peaceful.

407
00:21:25,960 --> 00:21:27,160
Very content in my family.

408
00:21:27,160 --> 00:21:31,520
We're very close, but a ton of conflict.

409
00:21:31,520 --> 00:21:34,720
That comes with the territory of having five siblings.

410
00:21:34,720 --> 00:21:37,680
It's a lot of kids to deal with.

411
00:21:37,680 --> 00:21:42,400
Yeah, I certainly hope for my kids.

412
00:21:42,400 --> 00:21:47,000
I'm not excited that my family relationship with my siblings is not stronger.

413
00:21:47,000 --> 00:21:49,320
I wouldn't say that it's something to strive for.

414
00:21:49,320 --> 00:21:53,840
I certainly hope that my relationship with my kids will be much stronger than what I

415
00:21:53,840 --> 00:21:54,840
have.

416
00:21:54,840 --> 00:21:57,440
We're both a little bit closer over time.

417
00:21:57,440 --> 00:22:03,440
What would you say it was like for you growing up in school in these different areas?

418
00:22:03,440 --> 00:22:07,480
Well, let's see.

419
00:22:07,480 --> 00:22:10,120
My school life was a bit different.

420
00:22:10,120 --> 00:22:11,800
I grew up in Montreal, Canada.

421
00:22:11,800 --> 00:22:19,200
I was an English kid at a French school at a time when the province of Quebec, where

422
00:22:19,200 --> 00:22:24,760
I lived, was holding a referendum to separate from the rest of Canada and be its own country.

423
00:22:24,760 --> 00:22:27,240
I was a bit of an outcast.

424
00:22:27,240 --> 00:22:28,920
I was the English kid.

425
00:22:28,920 --> 00:22:29,920
The bloke was called.

426
00:22:29,920 --> 00:22:32,920
That's what they called you.

427
00:22:32,920 --> 00:22:37,280
Bloke is a derogatory French-Canadian term for English Canadians.

428
00:22:37,280 --> 00:22:38,280
Oh, really?

429
00:22:38,280 --> 00:22:39,280
I've never heard that before.

430
00:22:39,280 --> 00:22:42,280
No, it's a French thing.

431
00:22:42,280 --> 00:22:44,280
I thought bloke was like your friend.

432
00:22:44,280 --> 00:22:50,840
Yeah, the British term of bloke.

433
00:22:50,840 --> 00:22:54,120
I didn't have a lot of friends, I would say, in high school.

434
00:22:54,120 --> 00:22:56,560
When I went, Quebec has a bit of a different system.

435
00:22:56,560 --> 00:23:01,640
They have a C-GEP, which is sort of junior college, and then only three years of university.

436
00:23:01,640 --> 00:23:04,640
Then I switched to English, and it was like a different world, right?

437
00:23:04,640 --> 00:23:07,440
Because we were all blokes.

438
00:23:07,440 --> 00:23:14,840
I became a lot more social and extroverted and had what I would describe as the typical

439
00:23:14,840 --> 00:23:21,040
US college life, which isn't necessarily the typical Canadian college life, where lots

440
00:23:21,040 --> 00:23:22,880
of going out with friends and partying.

441
00:23:22,880 --> 00:23:26,120
A lot of parties, a lot of beers.

442
00:23:26,120 --> 00:23:31,840
I was sort of half way maybe through college when I joined my first startup.

443
00:23:31,840 --> 00:23:36,640
I just sort of didn't know that concept existed.

444
00:23:36,640 --> 00:23:37,640
Was employee number one.

445
00:23:37,640 --> 00:23:41,640
It was me and Martin, this one other guy.

446
00:23:41,640 --> 00:23:43,440
We were trying to create something out of nothing.

447
00:23:43,440 --> 00:23:44,440
He was a terrible entrepreneur.

448
00:23:44,440 --> 00:23:47,440
I really hope he's not listening.

449
00:23:47,440 --> 00:23:52,520
What about him made him a bad entrepreneur?

450
00:23:52,520 --> 00:23:54,640
He spread himself too thin, I would describe it.

451
00:23:54,640 --> 00:24:02,080
He did software for courier companies like, think FedEx, but same day to help get the

452
00:24:02,080 --> 00:24:08,040
cars to pick up packages in the city from one location to another.

453
00:24:08,040 --> 00:24:09,960
We didn't have anything that worked.

454
00:24:09,960 --> 00:24:10,960
We lived in Montreal.

455
00:24:10,960 --> 00:24:15,120
We had a contract with a company in Montreal.

456
00:24:15,120 --> 00:24:20,920
Instead of getting a second contract, or instead of maybe getting that one to work, we got

457
00:24:20,920 --> 00:24:25,800
a second contract, but not in Montreal, in Toronto, which is a five hour drive away.

458
00:24:25,800 --> 00:24:27,600
The next one after that was in London.

459
00:24:27,600 --> 00:24:29,640
That's a flight away.

460
00:24:29,640 --> 00:24:30,640
Yeah.

461
00:24:30,640 --> 00:24:37,520
We were flying all over the place trying to make things work and things weren't working.

462
00:24:37,520 --> 00:24:38,520
Things didn't work ultimately.

463
00:24:38,520 --> 00:24:41,640
That company ultimately shut down.

464
00:24:41,640 --> 00:24:44,360
It was a great experience.

465
00:24:44,360 --> 00:24:47,640
It was during college and I just sort of fell in love with entrepreneurship.

466
00:24:47,640 --> 00:24:48,640
I didn't know.

467
00:24:48,640 --> 00:24:52,800
Now we're going back to the mid 1980s.

468
00:24:52,800 --> 00:24:55,640
Entrepreneurship wasn't... I didn't even know if it was a word that was why it was

469
00:24:55,640 --> 00:24:56,640
a big thing.

470
00:24:56,640 --> 00:25:00,960
Startup had a hyphen and a... I don't know.

471
00:25:00,960 --> 00:25:02,760
It certainly wasn't a big thing.

472
00:25:02,760 --> 00:25:06,960
None of my friends were entrepreneurs or weren't at startups.

473
00:25:06,960 --> 00:25:07,960
What are you talking about?

474
00:25:07,960 --> 00:25:08,960
Yeah.

475
00:25:08,960 --> 00:25:13,320
The way I described it is my conservative friends wanted to work for IBM and my progressive

476
00:25:13,320 --> 00:25:15,360
friends wanted to work for Microsoft.

477
00:25:15,360 --> 00:25:18,160
That was... I had a computer science degree.

478
00:25:18,160 --> 00:25:22,120
That was the spectrum of what was available back then.

479
00:25:22,120 --> 00:25:23,120
No Google?

480
00:25:23,120 --> 00:25:25,040
I guess Google wouldn't have been around then.

481
00:25:25,040 --> 00:25:30,720
Google was not even incorporated for 10 more years after that.

482
00:25:30,720 --> 00:25:32,280
It was Microsoft was the big one.

483
00:25:32,280 --> 00:25:33,280
Microsoft was new.

484
00:25:33,280 --> 00:25:34,280
That was the startup.

485
00:25:34,280 --> 00:25:35,280
Yeah.

486
00:25:35,280 --> 00:25:40,280
It's like, oh, you want to join this amazing big... It's going everywhere.

487
00:25:40,280 --> 00:25:43,280
It's the next big thing.

488
00:25:43,280 --> 00:25:44,280
Exactly.

489
00:25:44,280 --> 00:25:51,160
Yeah, so I don't know, my school life was not great in high school.

490
00:25:51,160 --> 00:25:55,240
And then by college was started to be focused on entrepreneurship.

491
00:25:55,240 --> 00:25:58,680
Do you think you were an extrovert or an introvert?

492
00:25:58,680 --> 00:26:02,600
I always describe myself as half and half.

493
00:26:02,600 --> 00:26:06,880
But COVID really taught me I'm much more extroverted than I thought.

494
00:26:06,880 --> 00:26:09,880
So it's funny we haven't talked about Techstars yet, but I remember early on in Techstars

495
00:26:09,880 --> 00:26:15,800
we funded a company that was doing group dating where a group of eight guys would sign up

496
00:26:15,800 --> 00:26:19,640
on the platform and a group of eight girls would sign up on the platform and then you'd

497
00:26:19,640 --> 00:26:21,480
facilitate a meeting of both groups.

498
00:26:21,480 --> 00:26:23,360
And so it was less pressure dating.

499
00:26:23,360 --> 00:26:25,240
That's a pretty good strategy.

500
00:26:25,240 --> 00:26:26,240
Yeah.

501
00:26:26,240 --> 00:26:27,240
I like it.

502
00:26:27,240 --> 00:26:33,480
And I remember the CEO was asking me questions about what did I think of the idea?

503
00:26:33,480 --> 00:26:38,120
Well, when I last went on the date, Google didn't exist.

504
00:26:38,120 --> 00:26:39,120
And he's like, what do you mean?

505
00:26:39,120 --> 00:26:40,120
I'm like, it didn't exist.

506
00:26:40,120 --> 00:26:41,120
It was down.

507
00:26:41,120 --> 00:26:42,120
And I'm like, no, it didn't.

508
00:26:42,120 --> 00:26:43,120
It wasn't a company yet.

509
00:26:43,120 --> 00:26:48,560
If you went to www.google.com, we're like, what happened?

510
00:26:48,560 --> 00:26:51,560
I'm like, there's no www.anything that didn't exist.

511
00:26:51,560 --> 00:26:53,240
Yeah, there was nothing there.

512
00:26:53,240 --> 00:26:57,080
So yes, that's the era that I grew up in going to college.

513
00:26:57,080 --> 00:26:58,080
There was no internet.

514
00:26:58,080 --> 00:26:59,080
There was nothing.

515
00:26:59,080 --> 00:27:01,000
There is no cell phone in your pocket.

516
00:27:01,000 --> 00:27:02,880
There was the only newspaper ads for dating.

517
00:27:02,880 --> 00:27:05,160
There were newspaper ads for dating.

518
00:27:05,160 --> 00:27:11,200
But that wasn't considered, it was pretty scary what you would find going out.

519
00:27:11,200 --> 00:27:18,760
It wasn't considered, like my cousin, he's still married to her, but went on a newspaper

520
00:27:18,760 --> 00:27:19,760
ad date.

521
00:27:19,760 --> 00:27:23,640
And we were like, whoa, what are you doing, dude?

522
00:27:23,640 --> 00:27:27,640
You find some scary stuff answering classified ads in the newspaper.

523
00:27:27,640 --> 00:27:29,640
So that was not the way to go dating.

524
00:27:29,640 --> 00:27:32,000
What do you mean by scary stuff?

525
00:27:32,000 --> 00:27:33,000
Was it like scary people?

526
00:27:33,000 --> 00:27:38,200
That's a good question because I never did it.

527
00:27:38,200 --> 00:27:41,120
I don't know that it was so scary what you found.

528
00:27:41,120 --> 00:27:43,840
Maybe I said that wrong.

529
00:27:43,840 --> 00:27:45,760
It just marked you as kind of desperate.

530
00:27:45,760 --> 00:27:51,560
If the only way you could find somebody was buying them off a newspaper ad.

531
00:27:51,560 --> 00:27:53,800
Yeah, that makes sense.

532
00:27:53,800 --> 00:27:57,440
Maybe that's the way it was when dating apps first started as well, where it was like you

533
00:27:57,440 --> 00:27:59,000
were going online to find people.

534
00:27:59,000 --> 00:28:03,160
It was because it's the same version as the classified personal ads they called them.

535
00:28:03,160 --> 00:28:04,160
You're advertising yourself online.

536
00:28:04,160 --> 00:28:05,520
Yeah, and you had to pay money.

537
00:28:05,520 --> 00:28:08,600
You had to pay money to be in the newspaper.

538
00:28:08,600 --> 00:28:13,600
Yeah, and you had to pay money to get an app and do well on it.

539
00:28:13,600 --> 00:28:15,960
When they first started out, they were monetizing it.

540
00:28:15,960 --> 00:28:16,960
Yeah, I guess you have to pay them out.

541
00:28:16,960 --> 00:28:17,960
Now they have all these free tiers.

542
00:28:17,960 --> 00:28:18,960
Do they?

543
00:28:18,960 --> 00:28:19,960
I don't know.

544
00:28:19,960 --> 00:28:24,480
I've been on a date since 1998.

545
00:28:24,480 --> 00:28:29,840
In recent years, people are actually having less relationships and they're having less

546
00:28:29,840 --> 00:28:34,240
sex and fertility rate in the US has gone below the replacement level.

547
00:28:34,240 --> 00:28:35,240
The replacement rate, 2.1.

548
00:28:35,240 --> 00:28:36,240
Yeah.

549
00:28:36,240 --> 00:28:39,240
So what do you think is different about dating now based on what you've seen?

550
00:28:39,240 --> 00:28:40,240
I have no idea.

551
00:28:40,240 --> 00:28:41,240
What are you talking about?

552
00:28:41,240 --> 00:28:42,240
Do you have kids?

553
00:28:42,240 --> 00:28:43,640
That's a good question.

554
00:28:43,640 --> 00:28:44,960
I don't know.

555
00:28:44,960 --> 00:28:46,120
I really don't know.

556
00:28:46,120 --> 00:28:57,200
I do have kids and they do date occasionally, but I can't really speak to how the dating

557
00:28:57,200 --> 00:28:58,740
scene works now.

558
00:28:58,740 --> 00:29:00,740
You want to know how it worked then?

559
00:29:00,740 --> 00:29:05,800
Even then I was like a lightweight, so I don't know that I could describe it then.

560
00:29:05,800 --> 00:29:07,360
Lots of other areas of expertise.

561
00:29:07,360 --> 00:29:09,920
This isn't one of them.

562
00:29:09,920 --> 00:29:13,000
Some people like to plan out a lot of things when they're young for what they want their

563
00:29:13,000 --> 00:29:14,000
lives to look like.

564
00:29:14,000 --> 00:29:16,000
Did you do a lot of that planning?

565
00:29:16,000 --> 00:29:17,000
None at all.

566
00:29:17,000 --> 00:29:18,000
None at all.

567
00:29:18,000 --> 00:29:23,400
And I always talk about that because I never had a five-year plan.

568
00:29:23,400 --> 00:29:25,400
I never had a one-year plan.

569
00:29:25,400 --> 00:29:28,080
I moved to the United States on three days notice.

570
00:29:28,080 --> 00:29:34,160
I literally got a job offer from a startup in Miami and accepted, flew back home, packed

571
00:29:34,160 --> 00:29:38,360
up all my stuff in my car and drove it down to the US.

572
00:29:38,360 --> 00:29:40,560
That was my plan.

573
00:29:40,560 --> 00:29:47,080
And I think I've always described myself as not having... I think it's really hard to

574
00:29:47,080 --> 00:29:48,080
have a plan.

575
00:29:48,080 --> 00:29:55,240
And I see this now with kids my age, students in college.

576
00:29:55,240 --> 00:29:58,800
There's sort of this desire to know exactly where you're going.

577
00:29:58,800 --> 00:29:59,800
You have a destination.

578
00:29:59,800 --> 00:30:05,040
And that's really hard because can you really decide three years, five years, 10, 20 years

579
00:30:05,040 --> 00:30:07,280
from now where you want to be?

580
00:30:07,280 --> 00:30:08,400
Life is not like that.

581
00:30:08,400 --> 00:30:11,480
Life meanders towards a destination.

582
00:30:11,480 --> 00:30:18,840
And if you have a bit of a sun where I like the brightness over there and this move will

583
00:30:18,840 --> 00:30:23,960
move me in that direction, that's how I've always operated my life.

584
00:30:23,960 --> 00:30:29,320
And so the independence, the startups, the entrepreneurship, the freedom, that was my

585
00:30:29,320 --> 00:30:38,840
son and any opportunity that felt more like... any opportunity that felt like it was moving

586
00:30:38,840 --> 00:30:42,960
me in that direction I took, anything I was doing that felt like I was moving away from

587
00:30:42,960 --> 00:30:45,360
that direction I got out of.

588
00:30:45,360 --> 00:30:46,740
That's all I did.

589
00:30:46,740 --> 00:30:50,880
And so it's a zigzaggy path as opposed to going there in a straight line.

590
00:30:50,880 --> 00:30:55,240
But it's way better than thinking about it and spinning on it for five years and then

591
00:30:55,240 --> 00:31:00,000
trying to zip to the destination, which is impossible to go in that straight line anyway.

592
00:31:00,000 --> 00:31:02,760
So you run your life a little bit like a startup, you would say?

593
00:31:02,760 --> 00:31:03,760
Yeah.

594
00:31:03,760 --> 00:31:04,760
Well, I mean, that's my personality.

595
00:31:04,760 --> 00:31:05,760
Yeah.

596
00:31:05,760 --> 00:31:07,480
You have a vision for something, something leading you.

597
00:31:07,480 --> 00:31:08,480
Yeah.

598
00:31:08,480 --> 00:31:09,480
Yeah.

599
00:31:09,480 --> 00:31:10,480
That's right.

600
00:31:10,480 --> 00:31:11,480
I think that's right.

601
00:31:11,480 --> 00:31:13,840
I know roughly what direction I want to go.

602
00:31:13,840 --> 00:31:21,440
And any move today that moves me a quarter inch in that direction is a move.

603
00:31:21,440 --> 00:31:22,720
Yeah, I'll take it.

604
00:31:22,720 --> 00:31:24,960
Even if it means changing countries or whatever.

605
00:31:24,960 --> 00:31:27,920
I mean, that won't be a big deal if you get to where you want to get.

606
00:31:27,920 --> 00:31:28,920
Right.

607
00:31:28,920 --> 00:31:29,920
Exactly.

608
00:31:29,920 --> 00:31:32,920
It didn't matter to me if I was in Canada, the US or Timbuktu.

609
00:31:32,920 --> 00:31:33,920
Timbuktu?

610
00:31:33,920 --> 00:31:36,440
That is a place, you know.

611
00:31:36,440 --> 00:31:37,440
Is it?

612
00:31:37,440 --> 00:31:38,440
It is.

613
00:31:38,440 --> 00:31:39,440
Where is it?

614
00:31:39,440 --> 00:31:40,440
That is a good question.

615
00:31:40,440 --> 00:31:41,440
Nepal?

616
00:31:41,440 --> 00:31:42,440
Nepal?

617
00:31:42,440 --> 00:31:43,440
Have you been?

618
00:31:43,440 --> 00:31:44,440
No.

619
00:31:44,440 --> 00:31:45,440
Oh.

620
00:31:45,440 --> 00:31:46,440
What do you think made your startup successful?

621
00:31:46,440 --> 00:31:47,440
At least the first one.

622
00:31:47,440 --> 00:31:49,920
Because I've never heard too much about that story.

623
00:31:49,920 --> 00:31:54,800
What made it work?

624
00:31:54,800 --> 00:32:03,400
I think I called the book, I wrote a book on it and I called it No Vision, All Drive.

625
00:32:03,400 --> 00:32:06,080
And it's really the story of starting that business.

626
00:32:06,080 --> 00:32:09,880
I did a second and third edition to include tech stars later on.

627
00:32:09,880 --> 00:32:12,200
Should all the viewers read it?

628
00:32:12,200 --> 00:32:13,200
They should.

629
00:32:13,200 --> 00:32:16,840
I will make a nickel every time you buy one.

630
00:32:16,840 --> 00:32:22,720
I think you can get it on Amazon and I charge as little as it is.

631
00:32:22,720 --> 00:32:25,360
And Amazon will let me.

632
00:32:25,360 --> 00:32:27,960
Because I think it is a good entrepreneurial story.

633
00:32:27,960 --> 00:32:29,400
So I think a few different things.

634
00:32:29,400 --> 00:32:37,480
One is we often talk in entrepreneurship about or people who aren't entrepreneurs often talk

635
00:32:37,480 --> 00:32:40,080
about how entrepreneurs are risk tolerant.

636
00:32:40,080 --> 00:32:44,580
Like they're capable of taking a large amount of risk.

637
00:32:44,580 --> 00:32:47,060
And I always like to say that's not what it felt like.

638
00:32:47,060 --> 00:32:49,480
And that's not how the entrepreneurs that I know are.

639
00:32:49,480 --> 00:32:50,760
They're not risk tolerant.

640
00:32:50,760 --> 00:32:56,200
It's not that they evaluate, oh, the risk is this big and I'm going to take that risk.

641
00:32:56,200 --> 00:32:57,200
They're risk ignorant.

642
00:32:57,200 --> 00:32:59,720
They don't even think about failure.

643
00:32:59,720 --> 00:33:01,960
Failure is not an option.

644
00:33:01,960 --> 00:33:03,560
I'm just going to go for it.

645
00:33:03,560 --> 00:33:08,400
And I think that's what made us successful because we were in our 20s.

646
00:33:08,400 --> 00:33:09,880
We didn't know what we were doing.

647
00:33:09,880 --> 00:33:13,200
We didn't know how to open a bank account much less run a business.

648
00:33:13,200 --> 00:33:15,040
We didn't know how to get customers.

649
00:33:15,040 --> 00:33:16,920
We didn't know how to create software.

650
00:33:16,920 --> 00:33:18,400
We didn't know how to sell.

651
00:33:18,400 --> 00:33:22,640
Go to trade shows, hire employees, get an executive team.

652
00:33:22,640 --> 00:33:25,400
Eventually, we didn't know how to sell the business.

653
00:33:25,400 --> 00:33:28,680
And we did all of those things.

654
00:33:28,680 --> 00:33:34,680
And we just figured it out as we went along because we were too stupid to realize that

655
00:33:34,680 --> 00:33:36,160
we didn't know what we were doing.

656
00:33:36,160 --> 00:33:40,320
And maybe we were lucky enough that we didn't have anyone around us that we cared about

657
00:33:40,320 --> 00:33:42,360
that were telling us we didn't know what we were doing.

658
00:33:42,360 --> 00:33:43,480
And we just figured it out.

659
00:33:43,480 --> 00:33:44,480
We guessed.

660
00:33:44,480 --> 00:33:48,720
We made lots of mistakes along the way.

661
00:33:48,720 --> 00:33:54,120
But in the end, it was a huge success.

662
00:33:54,120 --> 00:33:59,640
And so I can't say any of it was a mistake at all because it was all really great learning.

663
00:33:59,640 --> 00:34:02,560
It was part of the path.

664
00:34:02,560 --> 00:34:05,360
Every step was hard.

665
00:34:05,360 --> 00:34:12,900
Hiring your first employee, creating an employee manual because suddenly you have employees

666
00:34:12,900 --> 00:34:16,880
that are doing weird things and trying to figure out how to keep it within your culture.

667
00:34:16,880 --> 00:34:18,680
So a good story on that.

668
00:34:18,680 --> 00:34:21,120
What kind of weird things?

669
00:34:21,120 --> 00:34:29,080
Well, our very first employee manual had five things that you had to do at work.

670
00:34:29,080 --> 00:34:33,760
And the first one was underwear on the inside.

671
00:34:33,760 --> 00:34:37,120
And there was a reason.

672
00:34:37,120 --> 00:34:42,400
Our first developer always used to come in to work in sweatpants with boxer shorts outside.

673
00:34:42,400 --> 00:34:45,640
That was his fashion statement.

674
00:34:45,640 --> 00:34:51,840
And really, that employee manual was for item number two, whatever it was.

675
00:34:51,840 --> 00:34:56,680
And we had one employee always push the limits on charging on expenses.

676
00:34:56,680 --> 00:34:59,240
I don't remember what the actual policy was.

677
00:34:59,240 --> 00:35:02,600
But when we wrote the manual with the five things, I guess there were four things.

678
00:35:02,600 --> 00:35:05,960
And we're like, we can't make it seem all about this one guy.

679
00:35:05,960 --> 00:35:12,040
So we inserted the underwear on the inside as the first item in the employee manual.

680
00:35:12,040 --> 00:35:13,400
That guy without calling him out.

681
00:35:13,400 --> 00:35:14,400
Yeah, exactly.

682
00:35:14,400 --> 00:35:15,400
It's about the boxers.

683
00:35:15,400 --> 00:35:17,560
But it's a good story, right?

684
00:35:17,560 --> 00:35:19,040
Because it was true.

685
00:35:19,040 --> 00:35:20,040
It's a funny story.

686
00:35:20,040 --> 00:35:22,080
It was true.

687
00:35:22,080 --> 00:35:28,000
The guy was showing up for work with boxers on the outside.

688
00:35:28,000 --> 00:35:34,880
But it was like having that be part of our employee manual was true to our culture of

689
00:35:34,880 --> 00:35:39,180
just being irreverent and having fun at work.

690
00:35:39,180 --> 00:35:41,980
But getting the work done and being serious at the same time.

691
00:35:41,980 --> 00:35:45,800
So whatever those other four policies are that I don't remember, were important.

692
00:35:45,800 --> 00:35:47,440
We created that for a reason.

693
00:35:47,440 --> 00:35:51,560
And then, of course, that grew into a full policy manual over the years.

694
00:35:51,560 --> 00:35:55,760
And I'm sure when we got our first HR director, the first thing she did, we're taking number

695
00:35:55,760 --> 00:35:56,760
one out.

696
00:35:56,760 --> 00:35:57,760
We're like, that doesn't belong there anymore.

697
00:35:57,760 --> 00:35:58,760
That's not staying there.

698
00:35:58,760 --> 00:36:02,040
But then if someone did it again, you'd have to put it back.

699
00:36:02,040 --> 00:36:06,600
But I think the key point there, that's well, yes.

700
00:36:06,600 --> 00:36:10,840
The key point there is that's the beauty of having a startup.

701
00:36:10,840 --> 00:36:11,840
It's yours.

702
00:36:11,840 --> 00:36:12,840
You make of it what you want.

703
00:36:12,840 --> 00:36:14,960
You can be true to your personality and your culture.

704
00:36:14,960 --> 00:36:17,440
And you can have fun at work.

705
00:36:17,440 --> 00:36:21,920
It was a good laugh that we had that in the policy manual.

706
00:36:21,920 --> 00:36:28,960
And it helped us to not take ourselves too seriously in so many other ways.

707
00:36:28,960 --> 00:36:33,800
And I would say it's an example of one of the best things that we ever did was doing

708
00:36:33,800 --> 00:36:38,560
that because it caused us not to take ourselves too seriously.

709
00:36:38,560 --> 00:36:40,760
Did you ever lose it?

710
00:36:40,760 --> 00:36:41,760
The manual?

711
00:36:41,760 --> 00:36:42,760
No, not the manual.

712
00:36:42,760 --> 00:36:45,440
The air of not taking yourself seriously.

713
00:36:45,440 --> 00:36:46,680
I don't think I did.

714
00:36:46,680 --> 00:36:49,680
I mean, so I don't think it.

715
00:36:49,680 --> 00:36:51,600
I don't think I ever did.

716
00:36:51,600 --> 00:36:59,880
There was an era where after we sold the business and I'd left Pinpoint, some other guy took

717
00:36:59,880 --> 00:37:04,200
over and made it much more serious.

718
00:37:04,200 --> 00:37:07,000
And suddenly we're not in Boulder anymore.

719
00:37:07,000 --> 00:37:08,000
We're in Interlochen.

720
00:37:08,000 --> 00:37:11,560
We're in an office park.

721
00:37:11,560 --> 00:37:15,440
There's a dress code and casual Fridays.

722
00:37:15,440 --> 00:37:21,000
And that was the end of the Pinpoint I knew.

723
00:37:21,000 --> 00:37:22,000
So I think the company's-

724
00:37:22,000 --> 00:37:24,200
It was still called Pinpoint at that time.

725
00:37:24,200 --> 00:37:25,200
It's still there, honestly.

726
00:37:25,200 --> 00:37:26,200
It is?

727
00:37:26,200 --> 00:37:27,200
It's still there.

728
00:37:27,200 --> 00:37:28,800
It's not called Pinpoint anymore because we sold it.

729
00:37:28,800 --> 00:37:30,080
It's still on Interlochen?

730
00:37:30,080 --> 00:37:31,080
It's still down in Interlochen.

731
00:37:31,080 --> 00:37:32,080
I haven't seen it.

732
00:37:32,080 --> 00:37:33,080
I'll have to go pass by.

733
00:37:33,080 --> 00:37:34,960
Yeah, it's called Zoll Data Systems now.

734
00:37:34,960 --> 00:37:35,960
Okay.

735
00:37:35,960 --> 00:37:40,360
I've seen the Zoll when you pass by, sometimes like a fire.

736
00:37:40,360 --> 00:37:43,400
Yeah, so that's the company that bought us.

737
00:37:43,400 --> 00:37:44,400
It's a defibrillator.

738
00:37:44,400 --> 00:37:45,400
It's the thing that we start stuff-

739
00:37:45,400 --> 00:37:49,880
I'll see the defibrillators around places and I'll be like, oh, it's David Brown.

740
00:37:49,880 --> 00:37:52,560
That's the company that we sold Pinpoint to.

741
00:37:52,560 --> 00:37:55,500
So they just took your software and they made the defibrillators?

742
00:37:55,500 --> 00:37:56,500
And they made the defibrillators.

743
00:37:56,500 --> 00:37:57,500
Yeah.

744
00:37:57,500 --> 00:38:01,440
So I didn't want to touch on tech stars.

745
00:38:01,440 --> 00:38:07,520
You've seen so many companies go through and either fail or succeed, and there must be

746
00:38:07,520 --> 00:38:13,000
some common things that entrepreneurs fall into.

747
00:38:13,000 --> 00:38:14,480
What are those things?

748
00:38:14,480 --> 00:38:21,600
Well, the way I always answer that question is obsession.

749
00:38:21,600 --> 00:38:29,120
When you find that entrepreneur that's just obsessed with solving their problem, it really

750
00:38:29,120 --> 00:38:30,840
makes a difference.

751
00:38:30,840 --> 00:38:36,120
And the example I always give there is Isaac Saldana, who went through the Boulder program

752
00:38:36,120 --> 00:38:39,480
early on with his company, SendGrid.

753
00:38:39,480 --> 00:38:42,380
So SendGrid is well known today.

754
00:38:42,380 --> 00:38:48,880
They got bought by Twilio for like two or three billion dollars.

755
00:38:48,880 --> 00:38:55,440
They do a number of things, but the original SendGrid product kept email out of the junk

756
00:38:55,440 --> 00:39:02,680
folder, just handled all of the whatever the email protocols were that caused a normal

757
00:39:02,680 --> 00:39:04,700
email to go to the junk folder.

758
00:39:04,700 --> 00:39:10,120
And so think when you go to Uber and you click on forgot password, you don't want the link

759
00:39:10,120 --> 00:39:13,160
to go to spam.

760
00:39:13,160 --> 00:39:21,520
And Isaac and Jose, his co-founder, had worked as developers in a bunch of different companies,

761
00:39:21,520 --> 00:39:24,600
and they were always re-implementing whatever the protocols were.

762
00:39:24,600 --> 00:39:27,820
You probably know better than I do how this works, right?

763
00:39:27,820 --> 00:39:30,480
But they were always trying to solve this problem everywhere they went.

764
00:39:30,480 --> 00:39:35,660
And they said, well, why don't we create a company that solves it for everybody?

765
00:39:35,660 --> 00:39:39,500
And so they created SendGrid in order to do that.

766
00:39:39,500 --> 00:39:45,000
When I met those guys and we got them into the program, I didn't even understand what

767
00:39:45,000 --> 00:39:46,760
they did.

768
00:39:46,760 --> 00:39:49,640
Their company had a funny name.

769
00:39:49,640 --> 00:39:53,000
SMTP API was the name of the company.

770
00:39:53,000 --> 00:39:54,920
Great name.

771
00:39:54,920 --> 00:39:56,720
And they referred to it as SmitaPy.

772
00:39:56,720 --> 00:39:57,720
Oh, God.

773
00:39:57,720 --> 00:40:01,640
We've got to get on SmitaPy.

774
00:40:01,640 --> 00:40:06,480
Isaac and Jose were incredibly technical, and so they explained what their product did.

775
00:40:06,480 --> 00:40:08,400
And I was like bleeding out of the ears a little bit.

776
00:40:08,400 --> 00:40:10,920
Like I didn't even understand it.

777
00:40:10,920 --> 00:40:15,720
And I was there with my co-founders at Techstars, and one of them was like, we've got to take

778
00:40:15,720 --> 00:40:16,720
this company.

779
00:40:16,720 --> 00:40:17,720
I'm like, what do they do?

780
00:40:17,720 --> 00:40:19,640
And he's like, I'm not sure exactly.

781
00:40:19,640 --> 00:40:25,120
But it's something about email, and they care so much about it.

782
00:40:25,120 --> 00:40:27,160
They're so obsessed with it.

783
00:40:27,160 --> 00:40:32,780
And there's a lot of email out there that this is the team to go solve that problem.

784
00:40:32,780 --> 00:40:39,760
And so it was partly the basis of Techstars selection criteria was team, team, team, market

785
00:40:39,760 --> 00:40:41,080
progress idea.

786
00:40:41,080 --> 00:40:47,020
And so team, team, team, are these people part of the team, team, team, are these people

787
00:40:47,020 --> 00:40:51,240
so obsessed with their idea that they'll work day and night on it?

788
00:40:51,240 --> 00:40:52,240
And they were.

789
00:40:52,240 --> 00:40:53,760
And then is it a big market?

790
00:40:53,760 --> 00:40:55,080
This was the next criteria.

791
00:40:55,080 --> 00:40:56,080
Email.

792
00:40:56,080 --> 00:40:57,080
A lot of email.

793
00:40:57,080 --> 00:40:58,080
Huge market.

794
00:40:58,080 --> 00:41:05,640
Like, they had no revenue, they wanted to charge 0.0001 cents an email or whatever.

795
00:41:05,640 --> 00:41:10,680
And because that's all it really cost them to run the protocols, to figure out how to

796
00:41:10,680 --> 00:41:15,120
keep it out of the, to put the tags on, to keep it out of the spam folder.

797
00:41:15,120 --> 00:41:21,160
And during the course of Techstars, we got to the point that it was becoming so popular

798
00:41:21,160 --> 00:41:26,640
that we just told them, like, just double your price every day until somebody says no.

799
00:41:26,640 --> 00:41:27,640
And that's what they did.

800
00:41:27,640 --> 00:41:29,320
Where did they stop at?

801
00:41:29,320 --> 00:41:31,720
And I don't know what the price is.

802
00:41:31,720 --> 00:41:34,920
I mean, it's still per email, it's a small amount, right?

803
00:41:34,920 --> 00:41:41,120
But they now process like 2 billion emails a day or an hour or some crazy number like

804
00:41:41,120 --> 00:41:43,000
that.

805
00:41:43,000 --> 00:41:46,320
Millions and millions, tens of millions, maybe hundreds of millions in revenue.

806
00:41:46,320 --> 00:41:50,080
Huge, huge, huge business.

807
00:41:50,080 --> 00:41:53,880
They process something like, I don't even remember the numbers anymore, 5% of the world's

808
00:41:53,880 --> 00:41:57,080
non-spam email goes through.

809
00:41:57,080 --> 00:41:59,880
So anytime you click on forgot password, right?

810
00:41:59,880 --> 00:42:01,400
It's basically going through.

811
00:42:01,400 --> 00:42:02,640
SendGrid to send it to you.

812
00:42:02,640 --> 00:42:06,320
To send it to you and keep it out of the spam folder.

813
00:42:06,320 --> 00:42:12,360
And you know, many, many of us may not remember what it was like when most of your emails

814
00:42:12,360 --> 00:42:13,360
went to spam.

815
00:42:13,360 --> 00:42:14,760
It was just a pain in the butt.

816
00:42:14,760 --> 00:42:17,920
Now I get emails not in my spam that I want to go to spam.

817
00:42:17,920 --> 00:42:20,760
Yeah, well, that's not good either.

818
00:42:20,760 --> 00:42:30,200
But so back to the, you know, what made SendGrid succeed wasn't necessarily that they had real

819
00:42:30,200 --> 00:42:31,520
strong business savvy.

820
00:42:31,520 --> 00:42:35,360
As soon as the business got going, they immediately stepped back.

821
00:42:35,360 --> 00:42:39,520
Isaac immediately stepped back from being CEO and handed it over to one of his mentors.

822
00:42:39,520 --> 00:42:44,280
And he said, I don't want anything to do with the business side of things.

823
00:42:44,280 --> 00:42:47,480
So it's not that they had an unbelievable business strategy.

824
00:42:47,480 --> 00:42:49,400
They didn't have a pricing model that worked.

825
00:42:49,400 --> 00:42:53,560
They didn't have any revenue to speak of.

826
00:42:53,560 --> 00:42:58,400
It's not, you know, it wasn't any of the other normal things that you would think of as being

827
00:42:58,400 --> 00:43:02,200
so important to start a business.

828
00:43:02,200 --> 00:43:09,480
But man, they got out every day fired up about solving the world's email problems.

829
00:43:09,480 --> 00:43:16,400
And so that's why I think that obsession with the idea is the number one reason by far that

830
00:43:16,400 --> 00:43:18,960
makes a company successful.

831
00:43:18,960 --> 00:43:20,240
It gets you through the lows.

832
00:43:20,240 --> 00:43:22,040
Yeah, because you care so much.

833
00:43:22,040 --> 00:43:24,160
You care so much.

834
00:43:24,160 --> 00:43:25,720
And it doesn't have to be climate change, right?

835
00:43:25,720 --> 00:43:27,760
You don't have to be solving.

836
00:43:27,760 --> 00:43:28,760
You just have to care.

837
00:43:28,760 --> 00:43:32,160
So I don't have to care.

838
00:43:32,160 --> 00:43:33,160
But you care.

839
00:43:33,160 --> 00:43:34,160
Exactly.

840
00:43:34,160 --> 00:43:35,160
You're the one doing it.

841
00:43:35,160 --> 00:43:36,760
So if you don't care.

842
00:43:36,760 --> 00:43:37,760
Exactly.

843
00:43:37,760 --> 00:43:40,440
It's what's going to make you work the 14, 16 hour days.

844
00:43:40,440 --> 00:43:43,680
It's what's going to allow you to keep going when you don't have any money left in the

845
00:43:43,680 --> 00:43:47,480
bank account, when everything seems hopeless.

846
00:43:47,480 --> 00:43:52,440
You know, it's going to make you work harder, hire better people, do all the things that

847
00:43:52,440 --> 00:43:54,760
you have to do to make a business successful.

848
00:43:54,760 --> 00:43:58,640
Have you ever seen anyone not be obsessed and be successful?

849
00:43:58,640 --> 00:43:59,640
Yeah.

850
00:43:59,640 --> 00:44:07,960
I mean, sometimes people get lucky and stumble into a trend.

851
00:44:07,960 --> 00:44:09,960
But I don't think you can count on that luck.

852
00:44:09,960 --> 00:44:11,940
So I think it's the exception.

853
00:44:11,940 --> 00:44:17,080
And then what are common pitfalls for these other companies that don't really make it?

854
00:44:17,080 --> 00:44:20,000
Well, there are many.

855
00:44:20,000 --> 00:44:23,080
I think usually having a co-founder helps.

856
00:44:23,080 --> 00:44:25,600
Solo founders have a hard time.

857
00:44:25,600 --> 00:44:30,540
Partially for the same reason, there's ups and downs in any startup and there's ups and

858
00:44:30,540 --> 00:44:33,520
downs in your personal life.

859
00:44:33,520 --> 00:44:37,360
And when you have a co-founder, they can help you get through.

860
00:44:37,360 --> 00:44:43,560
Usually one's more emotionally volatile and one's more steady eddy.

861
00:44:43,560 --> 00:44:49,520
And the steady eddy person helps the emotionally volatile person get through the downs.

862
00:44:49,520 --> 00:44:54,280
And the emotionally volatile person is usually the one that comes up with the best ideas

863
00:44:54,280 --> 00:44:58,160
during the ups and takes the company in exciting new directions.

864
00:44:58,160 --> 00:45:02,920
And that yin and yang of that two different founder type is really helpful.

865
00:45:02,920 --> 00:45:08,840
Personally, right, when somebody has a down, the other founder can be there to help keep

866
00:45:08,840 --> 00:45:10,680
the company going.

867
00:45:10,680 --> 00:45:16,120
And I also think being CEO of a startup is a very lonely job.

868
00:45:16,120 --> 00:45:21,700
And having a co-founder allows you to have a peer, in a sense.

869
00:45:21,700 --> 00:45:25,320
As a CEO, you never really have a peer because you're at the top of the pyramid.

870
00:45:25,320 --> 00:45:30,900
But your co-founder is the closest thing you have to a peer so that you put on a brave

871
00:45:30,900 --> 00:45:32,200
face for everybody else.

872
00:45:32,200 --> 00:45:36,940
But for your co-founder, you can let the guard down a bit and let them know that you're really

873
00:45:36,940 --> 00:45:41,600
worried about the business failing or your marriage failing or whatever is going on in

874
00:45:41,600 --> 00:45:43,200
your life.

875
00:45:43,200 --> 00:45:46,240
And it's really helpful to have that outlet.

876
00:45:46,240 --> 00:45:51,160
And so I think companies or founders that don't have that are more likely to fail.

877
00:45:51,160 --> 00:45:58,880
What was your darkest days in the startup when you didn't need that co-founder to rely on?

878
00:45:58,880 --> 00:46:05,800
I always think of our darkest days at any startup being at pinpoint.

879
00:46:05,800 --> 00:46:12,960
We had created a prototype of the product.

880
00:46:12,960 --> 00:46:16,000
We were running out of cash.

881
00:46:16,000 --> 00:46:21,400
We had raised $100,000 pre-selling a product to our first customer.

882
00:46:21,400 --> 00:46:22,840
We were almost out of money.

883
00:46:22,840 --> 00:46:29,580
We needed to sell something.

884
00:46:29,580 --> 00:46:32,040
We signed up to go to a trade show somewhere.

885
00:46:32,040 --> 00:46:34,920
I don't even remember where that trade show was.

886
00:46:34,920 --> 00:46:40,320
We thought if we could only get one customer from that trade show, it would sustain us

887
00:46:40,320 --> 00:46:44,160
to the next thing.

888
00:46:44,160 --> 00:46:49,200
I remember we wanted to get a printer or something for $300 and we couldn't afford it.

889
00:46:49,200 --> 00:46:51,680
We were down to nothing.

890
00:46:51,680 --> 00:46:59,880
And we somehow had enough money to rent out a booth and get a spot.

891
00:46:59,880 --> 00:47:04,240
But we knew that if we didn't sign up a customer at the trade show, we wouldn't be able to

892
00:47:04,240 --> 00:47:06,160
pay for it, pay the bills.

893
00:47:06,160 --> 00:47:07,760
That's risky right there.

894
00:47:07,760 --> 00:47:09,160
That was it.

895
00:47:09,160 --> 00:47:17,160
What we didn't know was that this particular trade show, it's usually about customer discovery.

896
00:47:17,160 --> 00:47:18,960
You learn about the different products that are out there.

897
00:47:18,960 --> 00:47:23,080
Nobody buys at a trade show.

898
00:47:23,080 --> 00:47:29,400
In the lifetime of pinpoint, we only ever sold something to at a trade show twice.

899
00:47:29,400 --> 00:47:31,240
This was one of them.

900
00:47:31,240 --> 00:47:37,000
So thankfully, that customer, Bowers Ambulance, they were called somewhere in California,

901
00:47:37,000 --> 00:47:41,520
I was always grateful to them because they believed in us.

902
00:47:41,520 --> 00:47:44,440
And we sold them at that trade show and they wrote us a check.

903
00:47:44,440 --> 00:47:48,880
And if it hadn't been for that, we never would have, we would have folded.

904
00:47:48,880 --> 00:47:49,880
Yeah, it would have been over.

905
00:47:49,880 --> 00:47:50,880
It would have been over.

906
00:47:50,880 --> 00:47:54,760
So what were you planning on doing if you had it kind of hit that?

907
00:47:54,760 --> 00:47:56,760
Failure is not an option.

908
00:47:56,760 --> 00:47:58,600
Risk wasn't a thing.

909
00:47:58,600 --> 00:47:59,600
I was risk ignorant.

910
00:47:59,600 --> 00:48:03,240
We'll just sell something at the trade show.

911
00:48:03,240 --> 00:48:04,240
It'll work.

912
00:48:04,240 --> 00:48:05,240
It'll work.

913
00:48:05,240 --> 00:48:06,240
And it did.

914
00:48:06,240 --> 00:48:07,240
And it did.

915
00:48:07,240 --> 00:48:08,240
And that's a crazy story.

916
00:48:08,240 --> 00:48:09,240
Yeah.

917
00:48:09,240 --> 00:48:10,240
Yeah.

918
00:48:10,240 --> 00:48:14,200
I mean, and there were probably half a dozen stories just as crazy as that.

919
00:48:14,200 --> 00:48:16,360
Where you cut it off by a tiny edge.

920
00:48:16,360 --> 00:48:17,360
Yeah.

921
00:48:17,360 --> 00:48:20,440
And it was only the obsession that made you be willing to take those risks.

922
00:48:20,440 --> 00:48:21,440
And maybe the risk of ignorance.

923
00:48:21,440 --> 00:48:23,440
Yeah, the risk of ignorance and the obsession.

924
00:48:23,440 --> 00:48:26,640
We're like, oh, yeah, we'll cut it as close as possible.

925
00:48:26,640 --> 00:48:27,640
Yeah.

926
00:48:27,640 --> 00:48:37,360
And then there, I mean, another example was we got funding from our first customer, $100,000

927
00:48:37,360 --> 00:48:39,120
that we had to personally guarantee.

928
00:48:39,120 --> 00:48:46,800
Meaning David, my co-founder and I had to pay back the $100,000 jointly and severally,

929
00:48:46,800 --> 00:48:47,800
it's called.

930
00:48:47,800 --> 00:48:52,960
Which means if he couldn't pay out his half, like we were both in the hook for a hundred.

931
00:48:52,960 --> 00:48:53,960
Somebody had to pay.

932
00:48:53,960 --> 00:48:54,960
It didn't matter who.

933
00:48:54,960 --> 00:48:56,400
And we could work it out between us.

934
00:48:56,400 --> 00:48:57,400
Right?

935
00:48:57,400 --> 00:48:58,400
Yeah.

936
00:48:58,400 --> 00:49:04,560
I mean, we were basically college students and they would have owned our future house,

937
00:49:04,560 --> 00:49:06,040
our future anything.

938
00:49:06,040 --> 00:49:07,040
Right?

939
00:49:07,040 --> 00:49:10,840
And we're like, eh, okay, we'll sign up.

940
00:49:10,840 --> 00:49:12,200
We didn't have anything to lose.

941
00:49:12,200 --> 00:49:14,520
Yeah, I guess you had nothing.

942
00:49:14,520 --> 00:49:15,520
We had nothing.

943
00:49:15,520 --> 00:49:16,520
We're like, take it.

944
00:49:16,520 --> 00:49:22,640
Take my $100,000 worth of my $50 or whatever I have in my bank account.

945
00:49:22,640 --> 00:49:24,680
You can have the rest of my bank account.

946
00:49:24,680 --> 00:49:25,680
Oh.

947
00:49:25,680 --> 00:49:28,760
And then we utilized the business on $100.

948
00:49:28,760 --> 00:49:33,200
So that was the money that we put into the business to get it started at the very beginning

949
00:49:33,200 --> 00:49:34,200
pinpoint.

950
00:49:34,200 --> 00:49:36,840
David put in 50 and I put in 50.

951
00:49:36,840 --> 00:49:42,720
And the way we came up with that number was it was half of the highest of the two of our

952
00:49:42,720 --> 00:49:43,720
savings.

953
00:49:43,720 --> 00:49:47,440
Yeah, you had nothing.

954
00:49:47,440 --> 00:49:48,440
We had nothing.

955
00:49:48,440 --> 00:49:52,200
I mean, that's a great story because you can come from nothing and make a startup.

956
00:49:52,200 --> 00:49:53,200
Yeah.

957
00:49:53,200 --> 00:49:54,200
You don't have to have funding.

958
00:49:54,200 --> 00:49:55,200
You don't have to have all of these things.

959
00:49:55,200 --> 00:49:56,200
You don't have to have all of these other things.

960
00:49:56,200 --> 00:49:58,240
Or a good business plan.

961
00:49:58,240 --> 00:49:59,240
Nothing.

962
00:49:59,240 --> 00:50:04,240
And it was funny because we sold the company to Zold, you know, six years later for millions

963
00:50:04,240 --> 00:50:05,320
of dollars.

964
00:50:05,320 --> 00:50:10,760
And in the balance sheet, there's an entry called paid in capital, which shows how much

965
00:50:10,760 --> 00:50:12,520
money you put into the business.

966
00:50:12,520 --> 00:50:13,520
And it was like $100.

967
00:50:13,520 --> 00:50:15,960
Like it was, it was still there at the $100, right?

968
00:50:15,960 --> 00:50:20,160
It was, I didn't know anything about accounting and I didn't know that that like story would

969
00:50:20,160 --> 00:50:23,000
live on on the balance sheet every time we printed it.

970
00:50:23,000 --> 00:50:24,000
Yeah.

971
00:50:24,000 --> 00:50:25,000
Every time someone looks at it.

972
00:50:25,000 --> 00:50:26,000
$100?

973
00:50:26,000 --> 00:50:27,000
Seed funding.

974
00:50:27,000 --> 00:50:28,000
Seed, yeah, exactly.

975
00:50:28,000 --> 00:50:34,400
A lot of people struggle with entrepreneurship because there might be a lot of beliefs or

976
00:50:34,400 --> 00:50:37,960
insecurities about themselves where when it comes to making a startup, like, oh, people

977
00:50:37,960 --> 00:50:42,080
won't buy my stuff or, oh, I don't want to show up to someone's business and ask them

978
00:50:42,080 --> 00:50:43,080
for stuff.

979
00:50:43,080 --> 00:50:44,640
What was, did you have any of those?

980
00:50:44,640 --> 00:50:50,040
So I didn't really have imposter syndrome, which is what you're talking about.

981
00:50:50,040 --> 00:50:53,240
And it's not just what you described, but it's also this feeling that I don't know that

982
00:50:53,240 --> 00:50:55,440
I should be the CEO.

983
00:50:55,440 --> 00:50:58,760
I'm clearly not qualified.

984
00:50:58,760 --> 00:51:04,000
Somehow I always lacked the, it's not that I had self confidence.

985
00:51:04,000 --> 00:51:05,000
I was delusional.

986
00:51:05,000 --> 00:51:06,160
That's exactly right.

987
00:51:06,160 --> 00:51:12,000
I was delusional into thinking that my 25 year old self knew everything it needed to

988
00:51:12,000 --> 00:51:18,280
know to build a successful multimillion dollar business.

989
00:51:18,280 --> 00:51:25,400
And it's not that there weren't days where I had some self doubt, but they were few and

990
00:51:25,400 --> 00:51:26,400
far between.

991
00:51:26,400 --> 00:51:29,160
As delusional is the right word.

992
00:51:29,160 --> 00:51:30,160
Delusional self confidence.

993
00:51:30,160 --> 00:51:34,440
I have had delusional self confidence my whole career.

994
00:51:34,440 --> 00:51:36,000
Great skill to have right there.

995
00:51:36,000 --> 00:51:37,280
It is.

996
00:51:37,280 --> 00:51:38,280
It is.

997
00:51:38,280 --> 00:51:44,080
And I've talked a lot at different trade shows or talks I've given about the difference between

998
00:51:44,080 --> 00:51:50,120
arrogance and self confidence because I do think it's important to distinguish between

999
00:51:50,120 --> 00:51:51,120
the two.

1000
00:51:51,120 --> 00:51:52,440
I've always had self confidence.

1001
00:51:52,440 --> 00:51:54,120
I did have some arrogance.

1002
00:51:54,120 --> 00:51:59,840
I would say that got knocked out of me when I had a failed startup.

1003
00:51:59,840 --> 00:52:03,400
Because I don't think arrogance is helpful.

1004
00:52:03,400 --> 00:52:04,960
Self confidence is.

1005
00:52:04,960 --> 00:52:06,600
And they're like kissing cousins, right?

1006
00:52:06,600 --> 00:52:08,000
They're almost the same thing.

1007
00:52:08,000 --> 00:52:09,000
Yeah.

1008
00:52:09,000 --> 00:52:12,400
It's very hard to differentiate someone who is arrogant and very self confident.

1009
00:52:12,400 --> 00:52:17,360
And the difference is humility and maybe the willingness to make fun of yourself a little

1010
00:52:17,360 --> 00:52:18,360
bit.

1011
00:52:18,360 --> 00:52:26,000
And so the underwear on the inside, right, helps keeping it in the self confidence without

1012
00:52:26,000 --> 00:52:27,000
it being arrogance.

1013
00:52:27,000 --> 00:52:28,000
Yeah.

1014
00:52:28,000 --> 00:52:33,000
Like I'm, I might know stuff, but at the end of the day, it's all fun and games.

1015
00:52:33,000 --> 00:52:36,080
At the end of the day, we're all just trying to figure stuff out here.

1016
00:52:36,080 --> 00:52:40,280
Do you struggle with anything anymore internally?

1017
00:52:40,280 --> 00:52:44,400
You know, I do have that self confidence, I would say.

1018
00:52:44,400 --> 00:52:50,520
I mean, I'm sure I do, but in the grand grand scheme of things, no, I feel like I had a

1019
00:52:50,520 --> 00:52:54,400
period in my late twenties, maybe early thirties.

1020
00:52:54,400 --> 00:52:58,000
It was actually right when I moved to Boulder.

1021
00:52:58,000 --> 00:53:00,200
I sort of was rebuilt.

1022
00:53:00,200 --> 00:53:02,320
We moved our pinpoint to Boulder.

1023
00:53:02,320 --> 00:53:05,520
David, my co founder, was married.

1024
00:53:05,520 --> 00:53:08,240
We were still great friends, but we weren't roommates anymore.

1025
00:53:08,240 --> 00:53:09,640
I wasn't married at that time.

1026
00:53:09,640 --> 00:53:12,160
I wasn't dating.

1027
00:53:12,160 --> 00:53:18,280
And it was sort of, I don't want to say lonely, but I had more, I had more alone time.

1028
00:53:18,280 --> 00:53:24,600
And I went through this period of what we wound up calling radical self inquiry, like

1029
00:53:24,600 --> 00:53:26,840
where you're just introspecting all day long.

1030
00:53:26,840 --> 00:53:28,120
I don't know why I did it.

1031
00:53:28,120 --> 00:53:30,600
I didn't read a book or something.

1032
00:53:30,600 --> 00:53:32,880
I think I was just bored and I had nothing.

1033
00:53:32,880 --> 00:53:35,920
I had no one to be with except my own thoughts.

1034
00:53:35,920 --> 00:53:41,000
And I figured out who I was and what I was good at and what I wasn't good at and what

1035
00:53:41,000 --> 00:53:44,080
I liked about myself and what I didn't like about myself.

1036
00:53:44,080 --> 00:53:47,280
And then I remember going through this process of thinking about all the things I didn't

1037
00:53:47,280 --> 00:53:53,160
like about myself and putting them in categories of I want to fix this or I don't care.

1038
00:53:53,160 --> 00:53:54,160
Right?

1039
00:53:54,160 --> 00:53:55,160
Like that's who I am.

1040
00:53:55,160 --> 00:53:56,160
Right?

1041
00:53:56,160 --> 00:53:58,240
And then put it into the, I'm okay with it.

1042
00:53:58,240 --> 00:54:01,080
It's a character flaw, but nobody's perfect.

1043
00:54:01,080 --> 00:54:05,400
And that process that I went through in my late twenties, early thirties, I think changed

1044
00:54:05,400 --> 00:54:14,480
me for the rest of my life because it sort of put into my past this need to worry about

1045
00:54:14,480 --> 00:54:15,480
have I done the right thing?

1046
00:54:15,480 --> 00:54:16,480
Am I good?

1047
00:54:16,480 --> 00:54:17,480
Am I not good?

1048
00:54:17,480 --> 00:54:23,880
And because ever since then, I've, I've, I've felt like I know who I am.

1049
00:54:23,880 --> 00:54:24,880
I know what I'm good at.

1050
00:54:24,880 --> 00:54:26,880
I know what I'm not good at.

1051
00:54:26,880 --> 00:54:28,600
And I'll stick to the things that I'm good at.

1052
00:54:28,600 --> 00:54:30,080
Thank you very much.

1053
00:54:30,080 --> 00:54:35,080
And, and construct a life around the things that give me joy and happiness.

1054
00:54:35,080 --> 00:54:38,000
So you took away a lot of those shoulds in your life.

1055
00:54:38,000 --> 00:54:39,000
Yeah.

1056
00:54:39,000 --> 00:54:40,000
I should do this.

1057
00:54:40,000 --> 00:54:41,000
I should do that.

1058
00:54:41,000 --> 00:54:44,480
Somebody told me I should do this or I don't have any, I don't feel like I have any of

1059
00:54:44,480 --> 00:54:47,720
those and I don't feel like I had any of those for 30 years.

1060
00:54:47,720 --> 00:54:48,720
That's amazing.

1061
00:54:48,720 --> 00:54:49,720
Yeah.

1062
00:54:49,720 --> 00:54:51,720
I've had those in my life, but not recently.

1063
00:54:51,720 --> 00:54:52,720
Yeah.

1064
00:54:52,720 --> 00:54:53,720
That's amazing.

1065
00:54:53,720 --> 00:54:59,920
One of the traditions we like to have to close out the podcast is we, we get the, the guests

1066
00:54:59,920 --> 00:55:02,000
to make a little challenge for themselves.

1067
00:55:02,000 --> 00:55:06,120
Something that would maybe make your, your life a little bit, a tiny bit better, maybe

1068
00:55:06,120 --> 00:55:10,320
a little bit more peaceful that you could do in like a week or two weeks that would

1069
00:55:10,320 --> 00:55:14,200
make a small little impact on your life in a positive direction.

1070
00:55:14,200 --> 00:55:15,200
And say it out loud.

1071
00:55:15,200 --> 00:55:16,200
Yeah.

1072
00:55:16,200 --> 00:55:18,200
You say it out loud and put a deadline on it.

1073
00:55:18,200 --> 00:55:23,200
Well, so first of all, I'm not that kind of, I don't need that kind of motivation.

1074
00:55:23,200 --> 00:55:27,080
And I have one of those things and I'm not going to get it done in a week or two, but

1075
00:55:27,080 --> 00:55:28,680
I'm going to get it done this year.

1076
00:55:28,680 --> 00:55:30,160
I can't share it.

1077
00:55:30,160 --> 00:55:32,680
And it's on my mind is the biggest life changing thing.

1078
00:55:32,680 --> 00:55:38,160
It's basically, it's cutting out one of the biggest time sucks in my life that isn't giving

1079
00:55:38,160 --> 00:55:40,640
me pure joy.

1080
00:55:40,640 --> 00:55:43,840
It's a side project that I have.

1081
00:55:43,840 --> 00:55:46,560
And it's not that it's not enjoyable.

1082
00:55:46,560 --> 00:55:49,080
I work with other people who are nice.

1083
00:55:49,080 --> 00:55:52,400
It actually generates income, which is nice.

1084
00:55:52,400 --> 00:55:59,560
I don't have, there's nothing wrong with it, but it's not in the camp of, I really

1085
00:55:59,560 --> 00:56:00,560
love it.

1086
00:56:00,560 --> 00:56:05,480
And, and I've made promises to people that I need to keep.

1087
00:56:05,480 --> 00:56:11,320
And so I'm going to spend this year, 2024, extracting myself from that.

1088
00:56:11,320 --> 00:56:13,400
I'm not going to get it done in two weeks.

1089
00:56:13,400 --> 00:56:15,960
No, I mean, that fits the spirit of it.

1090
00:56:15,960 --> 00:56:16,960
Yeah.

1091
00:56:16,960 --> 00:56:19,560
And I think it's really good to do those things.

1092
00:56:19,560 --> 00:56:21,560
I mean, if it were, it could be done in two weeks.

1093
00:56:21,560 --> 00:56:23,040
I'd have done it yesterday.

1094
00:56:23,040 --> 00:56:24,120
It's just a longer one.

1095
00:56:24,120 --> 00:56:25,160
It's just a longer one.

1096
00:56:25,160 --> 00:56:30,440
And it's going to free up time for me to do more things that really do give me joy.

1097
00:56:30,440 --> 00:56:31,440
Awesome.

1098
00:56:31,440 --> 00:56:32,680
Well, thank you for coming on David.

1099
00:56:32,680 --> 00:56:33,680
Well, thanks for having me.

1100
00:56:33,680 --> 00:56:35,880
Where can people find you?

1101
00:56:35,880 --> 00:56:38,400
You can, where can people find me?

1102
00:56:38,400 --> 00:56:43,240
If you want people to find you.

1103
00:56:43,240 --> 00:56:47,680
I am, I don't have much of a social profile anymore, but if people want to reach out to

1104
00:56:47,680 --> 00:56:54,200
me at dbrown at Colorado EDU, that's my CU email address.

1105
00:56:54,200 --> 00:56:55,200
Cool.

1106
00:56:55,200 --> 00:56:56,200
Very responsive on email.

1107
00:56:56,200 --> 00:56:57,640
And you have your book out.

1108
00:56:57,640 --> 00:56:59,440
You should read the book.

1109
00:56:59,440 --> 00:57:00,440
Yes.

1110
00:57:00,440 --> 00:57:02,960
No vision, all drive available on Amazon.

1111
00:57:02,960 --> 00:57:03,960
Cool.

1112
00:57:03,960 --> 00:57:09,400
But buy it because you're interested in a personal story of an entrepreneur and how

1113
00:57:09,400 --> 00:57:12,120
it all worked.

1114
00:57:12,120 --> 00:57:13,120
It's not a commercial.

1115
00:57:13,120 --> 00:57:15,640
I'm not doing it for commercial reasons.

1116
00:57:15,640 --> 00:57:16,640
No.

1117
00:57:16,640 --> 00:57:17,640
I'm doing it because-

1118
00:57:17,640 --> 00:57:18,640
To get something good out of it.

1119
00:57:18,640 --> 00:57:19,640
Yeah.

1120
00:57:19,640 --> 00:57:23,280
If people are interested in my story and want to hear more, you can hear about it there.

1121
00:57:23,280 --> 00:57:24,280
I think it's a great story.

1122
00:57:24,280 --> 00:57:25,280
Yeah.

1123
00:57:25,280 --> 00:57:26,280
Fantastic.

1124
00:57:26,280 --> 00:57:27,280
Awesome.

1125
00:57:27,280 --> 00:57:28,280
Thank you.

1126
00:57:28,280 --> 00:57:57,060
Are you in?