Hello everyone, welcome to the first episode of the CNS Podcast.
Our guest today is David Brown.
He is an investor, an author, and founder of the global accelerator Techstars.
Everybody's got advice for you for how to make it as an entrepreneur these days.
David's accelerator Techstars has invested in over 4,000 startup companies, including
unicorns such as Sendgrid, Twilio, and Uber.
What does he think it actually takes to be a successful entrepreneur?
Today we will discuss how David's first company became a success with $100, common pitfalls
of entrepreneurs, why it's better not to have a plan for the future, the difference
between arrogance and self-confidence, and much more.
Thanks for listening.
You've participated in a lot of different ventures over your lifetime, and I'm curious
into how you would say your passion's kind of connected into each different one that
you've done.
I mean, I feel that it's always connected, right?
Because you spend so much of your time at work that if you're not passionate about what
you do, you kind of don't have a great life.
You better find a different line of work.
And so to me, they're all massively interconnected.
So first you had pinpoint technologies, right?
Yeah, that was my first startup.
I started that pretty soon after college, a long, long time ago.
And what was that one that kind of called to you?
It was funny, right, because I actually got a job out of college working for an ambulance
company, and I was basically the IT guy.
They didn't use the CTO title back then.
I don't even remember what it was, but some equivalent.
And so I was working for somebody else, and I had another guy there with me, also named
David.
We were basically both the IT guys, and we created the software to help run this ambulance
company.
And we thought, wouldn't it be cool to just sell the software to a bunch of other ambulance
companies instead of running the service, which is what our boss did?
And we approached him about, hey, could we create a branch, a division that sold the
software?
And he wasn't interested.
And so we said, well, we'd like to go do it on our own.
And miraculously, with his support, we went off and created our own software and launched
our first business that way.
And that was Pinpoint.
That was Pinpoint.
That was called Pinpoint Technologies.
And it was just straight after college?
And it was probably my mid-20s, mid to late 20s, because I graduated college.
I worked for this ambulance service as the IT guy for a couple of years.
I met my co-founder, David.
We plotted a little bit.
And so it was something.
A little bit of plotting, scheming, and the plot stuff.
We had a day job with the boss.
Yeah, you had to do it on your own.
And we wanted to basically take the idea that we were doing for work and go create a company
around it.
I think we were mindful that maybe there was some IP issues.
We wanted to leave on good terms with John or do it with John, our boss.
And so anyway, we worked that out and then started a software company.
We didn't know anything about what we were doing in our 20s, figuring things out as we
went.
How did you know that the co-founder was the right one?
Speaking of relationships and friendships, what was different about it?
So it's an interesting question because the co-founder relationship I now know is the
most important part to get right.
And David and I were best friends.
We're best men at each other's wedding.
We've known each other for, God, that was the early 90s.
So what's that?
That's 34 years.
34 years.
34 years ago.
And we're still great friends.
Go to lunch every week.
And so it worked out.
And so I don't know that we were smart about it.
We got lucky.
We worked together for this guy, John, for a while before branching out.
And we were roommates for a while.
And we didn't really think that John always got things right.
And we had ideas of how to do our own business.
And so I think we became partners in crime, trying to figure that out, scheming and coming
up with ideas.
It brought us closer together.
Yeah, exactly.
So I think in many ways, we were friends before we were business partners.
There might be something to be said about friends where you build towards something
together and how those friendships kind of add more to your life.
Yeah, and deep friends, right?
Because we were roommates.
So we worked together.
We had fun.
We had the same personal circle.
We had the same life.
So there was no issue.
Exactly.
It's like, oh, you want to go do this together?
We can do everything together.
What's the difference?
That's a great friend to have right there.
I mean, I call him my work spouse.
He doesn't like that.
Oh, really?
What does he say back to it?
I don't know.
I don't know what it sounds like to him.
We each have our own spouses.
But it's the closest thing to a permanent relationship other than sort of who you marry.
And so very, very much been my work spouse my whole life.
I'm always curious about the motivation factors that go into why people do things.
And some entrepreneurs have this deep need to prove other people wrong or have this deep
purpose that I knew since I was young.
What was kind of that thing for you when you were in your early 20s and you're sitting
there like, oh, I should do this thing.
So it wasn't money, first of all, for sure.
That was usually not for work.
No, but I think a lot of entrepreneurs sort of have this image that you're going to become
rich.
But when you start off with that notion, you almost never do.
So it certainly wasn't that for us.
And I think it was a desire to create something out of nothing.
It was sort of the creativity of it and the difficulty of like, nothing is there in this
space.
And we think that problem should be solved.
And it's not just as easy as writing some code and creating a product.
You have to get customers and learn sales and incorporate a business and hire employees
and pick a headquarters, get an office.
Pay taxes, whatever.
Pay taxes.
All kinds of crazy things that you got to figure out as you go.
And it was just a whirlwind of figuring that out.
And it was a blast.
The figuring it out was the fun part.
And what did that creation aspect where you have nothing and you create something, what
did that do for you internally in terms of like an emotional connection to it?
It feels great, right?
Like it gives you, it gives your life purpose and meaning.
And it turns out that that business, and we can get to this, but that business and all
my other businesses that succeeded had purpose.
And the ones that didn't have purpose failed.
And so, the software we were creating at Pinpoint was to dispatch ambulance and save lives.
And so you felt like you were making the world a better place as a result of what your business
did.
And it's an amazing feeling to have that purpose.
It allows you to sort of get up in the morning and work hard without it feeling like any
effort whatsoever.
Without it feeling like you're working 80 hours a week.
Totally.
You're just working all the time, but it's a blast.
It's a great time.
There's some saying that I heard that, you know, an entrepreneur that's passionate about
what they do because they're so focused on their business, they forget to eat or poop.
They're so focused that that's what you do all day and you get to the end of the day
and you're like, oh.
Good day.
I forgot to eat, but it was still good.
You talk about meaning and purpose, which I think is quite interesting.
I don't know if you've ever read Victor Frankl's Man Search for Meaning.
I haven't.
Great book.
I love it.
So he talks about the concentration camps and one of the differences between people
who made it out and people who didn't.
And one of those things was this idea of a bigger meaning or a bigger purpose, a bigger
life accomplishment that they still had hope for regardless of whether they were going
to make it out or not.
They had no idea.
And the ones that would lose hope were the ones that didn't have that larger thing to
work towards.
So it might be a similar thing in business.
Yeah.
I mean, obviously I can't compare anything to being in a concentration camp, but I do
think it's true that if you give up hope on your startup, it's going to fail.
Once you start getting that feeling that maybe it's not going to work, it's not going to
work.
I agree.
But hope is intricately tied to that other purpose that isn't the money or the success.
It has to be like, oh, I'm actively going out and helping these people with the ambulance
business say or whatever business you're making.
Yeah.
You're saving lives is what the purpose was at that first startup at Pinpoint and at Tech
Stars later on, it was about helping entrepreneurs succeed.
And when you had that purpose, when you could define, articulate that purpose in easy words
and that not only you, but everybody in the company could rally around it, it made it
a lot easier to go to work every day.
I can feel that as well, where it's like you have some bigger purpose to work towards.
It makes work so much easier.
And the company that failed was basically an early social media app, which was probably
ahead of its time.
But we never really felt like we had purpose.
We wanted to do the entrepreneur thing again.
We felt like we were successful.
Like, oh, I know what I'm doing.
I know what I'm doing now.
And it wasn't, you know, I don't know why we picked that idea, but we weren't passionate
about the idea.
The idea didn't give our life meaning and purpose.
And it made it a lot harder when things got tough.
You know, when things get tough in the ambulance business, you push through because you're
saving lives.
Okay.
You know, that was a sucky day, but I'm going to push through and do it.
But if nobody gets to use your social media app that nobody's using, you don't care all
that much.
You don't really care.
Yeah.
What am I offering?
I might as well give up.
I'm working a lot of hours.
I'm not making any money.
I'm losing hope.
It's too easy to give up.
And that's very important is making it impossible to give up in a startup.
I want to touch on tech stars in a bit, but I also want to dive deeper into those younger
years when you're starting out.
You didn't really get into this relationships until later on in your life, right?
What was kind of dating and having romantic relationships like for you in those younger
years?
It was, you know, it was sparse, right?
I was really, really focused on the business.
I mean, I dated, I had girlfriends going back to before I even moved to the US.
So before this first startup, I was born and raised in Canada and I dated even for a couple
years.
So I think it was a normal life in that regard, but it was few and far between because if
you weren't dating anybody, you're so focused on the business, you're not meeting anybody.
Exactly.
You're not going outside.
Exactly.
You're sitting inside all the time.
Yeah, but I do think like, and some of this I wish I could have applied to my life going
back, but I do think that having that balance and certainly I've been married a long, long
time now since that very first startup.
And I think, you know, having a different life outside of work, having a personal life,
having a significant other kids, whatever your thing is, is really helpful to balance
the, I always described it as work was chaos, ups and downs and craziness and customers
coming and going and highs and lows and you know, and then at home, everything was like
stable, right?
I've lived in the same house for 30 years.
I've had the same wife for 25 years, whatever.
Same house, same, I used to say same house, same wife, same kids, same dog.
Dog died.
But it was very grounding to balance out the chaos of running a startup with having a more
stable personal life at home.
That's interesting.
I think a lot of people push towards a more balanced approach to entrepreneurship, like
you're saying, and then some people go towards the, oh, you don't have really the bandwidth
to deal with a relationship.
Yeah, I don't believe that.
I think that's self-imposed.
There are lots of entrepreneurs that find time to do that and it just took me longer.
I mean, that was me from when I started Pinpoint to when I sold Pinpoint.
So that was about six years.
Just all in giving 100% every day, day and night, roommates with David, working on the
business, trying to grow it.
There was barely time for a social life.
But was that necessary to make the business successful?
I don't believe that.
I think it would have gone big anyways.
Yeah.
Because I think that when you balance your life with a relationship or sleep or whatever
it is, right, that I think you make better business decisions at work.
And so even if you're not spending 16 hours a day at the office and you're only spending
10 or 12, right, that you still can accomplish just as much maybe more because you're well
rested, you're recharging, you're sharper, you're not making as many bad decisions.
Yeah.
And that's why one of the things we're focusing on is creating a more synergistic life because
I don't know if you go online very much often, but a lot of the narrative online with entrepreneurship,
there's a lot of entrepreneurship influencers and stuff.
And they're always pushing this narrative of, oh, you have to be on the grind 24-7 and
you have to give up everything else.
I don't think that's true.
But I think when you're on, you have to be on, right?
So in other words, but give yourself permission to be off.
So I disagree with those that say you have to be on 24-7 because I think when you're
on 24-7, you're not as sharp.
I agree.
It's a true story, but it's the example I always give to prove that point is I have
always slept nine hours a night, right?
Ten hours on weekends, right?
I love my sleep.
And a lot of people say, how do you...
People always used to say to me, how do you get so much done?
Right?
I'm good on email.
I go to meetings.
I'm running a business.
I mean, I'm not doing that now, but I was.
And I would say that because I was well rested, my brain was sharper.
I made better decisions.
I made fewer mistakes.
I did less of the, oh, I don't know what to do about that problem.
Let me set it aside and think about it later.
And then you're always coming back to the same thing over and over again.
You're on your back foot.
What's that?
You're running on your back foot, basically.
Yeah, exactly.
Whereas I was very, very good at problem come in, here's what I'm going to do.
Move on.
Next problem, please.
Right?
I was running at 100%.
You're running at 100% when you're doing that.
Same thing with email.
I had hundreds of emails every day and I would just text them one at a time.
What am I going to do with this one?
Do it.
What am I going to do with this one?
Do it.
What am I going to do with this one?
Do it.
Not, ugh, let me leave that in my inbox and then it accumulates and then you have 2000
emails in your inbox that people are waiting for you on.
That was never me.
No, yeah, 100%.
I think one of the most important things you mentioned right there is you were getting
all your sleep and recharging.
But when you were on, you were doing actions all the time.
It wasn't just, oh, I'm working dilly dally or I'm stressing about this thing.
It was, oh, I'm going to do the thing.
Yeah, so that's what I'm saying.
You don't have to be on 24-7, but when you're on, you have to be on.
It's okay if that's 12 hours a day.
I think then the option is you're recovering and you're sleeping and you actually get stuff
done during those hours you're working or you can do it slower.
I'll give you a counter example.
To some extent, I had this when my kids were born and you had more sleepless nights.
Yeah.
And you show up at work the next day and your brain just felt like it's not firing in all
cylinders.
Decisions would come slower and emails would accumulate in the inbox.
You couldn't get stuff done.
And so training the brain to be really good at it, and part of that's getting enough sleep,
but there's more to it than that.
I think it makes it much more- Was there anything in particular you did to
optimize your decision making or action ability other than sleep?
Yeah.
It took me years to learn this, but vacations off the grid was the only one that I would
do where I would take a vacation where I was not constantly checking email.
It's a different version of brain rest than sleep, but go to the beach, hang out with
family, have a fun time, whatever you're doing, be present in the moment.
So what if I come back to 3,000 emails in my inbox and I would go through them and I
would answer every one.
My wife will tell you, we always took our vacations.
We came back on Saturday so that Sunday I could work all day on email before going back
to the office on Monday, plow through them.
So there was something there with fully disconnecting-
There was something there to fully disconnecting and recharging the batteries.
And I guess that's similar to sleep, but it's the same, it's similar in that you're resting
your brain but in a different way.
You're making your life about more than just your business.
You're spending time with your family or your loved ones or in a beautiful place or whatever.
You're actually having a life.
You're having a life.
You're having a good time.
When you built all these businesses and you are the person we are today, what parts of
your childhood do you think kind of influenced what you did throughout your life?
I'm deep here, dude.
I used to describe myself as the odd man, odd person out in my family because my father
worked for the city, a very nine to five job.
He worked there for 30 years or something for all my life until he retired.
My mother was a social worker, same thing.
She worked part time two days a week while she raised the kids and did that all her life,
not all her life, but all my life.
I never knew her to have a different role than that.
My brother became a university professor and a real professor not like me.
So he got his PhD and was in academia all his life.
I was this crazy entrepreneur that went off and started business.
I don't want to say a black sheep in the family in the sense that it's not that they looked
down on me, but nobody understood anything about what I did.
Do they have doubts?
I don't think doubts is the right word.
They didn't understand it at all.
I worked crazy hours.
I moved to the United States.
I disappeared from the family as far as they were concerned, but I seem to be having fun.
Whatever David's doing, he seems to be enjoying it.
So good on him was my family's attitude to it.
So during those years you didn't see them very often?
No, no.
I saw them.
I'm from Canada, from Montreal, so it was a long flight.
I was living in Florida in those early years.
It was a long flight home, but I'd go home every year.
We'd have Christmas together, normal family stuff.
But it's not that I was hanging out with them every week.
You were off in Florida, they were in Canada.
Yeah, they'd come visit me.
What was your relationship like with your brother?
I have a sister too, and they are very close to each other.
While we are civil is too weak a term, but while we communicate regularly, we have Zoom
calls still every other month or something like that to catch up.
I would not say I'm as close to either my brother or my sister as they are to each other.
I've heard some advice where it goes you have two options when dealing with family, and
one of them is you're either really close and you have a lot of conflict, or you're
first of all and you get along and you're not the most close that you could be, but
it's awesome and it's a great time.
Yeah, I would say it's unfortunate.
I don't know that I fit into either of those camps.
It's unfortunate that I'm not closer to my siblings, but I feel like in some ways I don't
have a lot in common with them.
They live a very different life, and they probably view me the same way.
Nothing wrong with that, and we still like each other and talk to each other and visit
each other.
So it's still peaceful.
Yeah, it's always been peaceful.
Very content in my family.
We're very close, but a ton of conflict.
That comes with the territory of having five siblings.
It's a lot of kids to deal with.
Yeah, I certainly hope for my kids.
I'm not excited that my family relationship with my siblings is not stronger.
I wouldn't say that it's something to strive for.
I certainly hope that my relationship with my kids will be much stronger than what I
have.
We're both a little bit closer over time.
What would you say it was like for you growing up in school in these different areas?
Well, let's see.
My school life was a bit different.
I grew up in Montreal, Canada.
I was an English kid at a French school at a time when the province of Quebec, where
I lived, was holding a referendum to separate from the rest of Canada and be its own country.
I was a bit of an outcast.
I was the English kid.
The bloke was called.
That's what they called you.
Bloke is a derogatory French-Canadian term for English Canadians.
Oh, really?
I've never heard that before.
No, it's a French thing.
I thought bloke was like your friend.
Yeah, the British term of bloke.
I didn't have a lot of friends, I would say, in high school.
When I went, Quebec has a bit of a different system.
They have a C-GEP, which is sort of junior college, and then only three years of university.
Then I switched to English, and it was like a different world, right?
Because we were all blokes.
I became a lot more social and extroverted and had what I would describe as the typical
US college life, which isn't necessarily the typical Canadian college life, where lots
of going out with friends and partying.
A lot of parties, a lot of beers.
I was sort of half way maybe through college when I joined my first startup.
I just sort of didn't know that concept existed.
Was employee number one.
It was me and Martin, this one other guy.
We were trying to create something out of nothing.
He was a terrible entrepreneur.
I really hope he's not listening.
What about him made him a bad entrepreneur?
He spread himself too thin, I would describe it.
He did software for courier companies like, think FedEx, but same day to help get the
cars to pick up packages in the city from one location to another.
We didn't have anything that worked.
We lived in Montreal.
We had a contract with a company in Montreal.
Instead of getting a second contract, or instead of maybe getting that one to work, we got
a second contract, but not in Montreal, in Toronto, which is a five hour drive away.
The next one after that was in London.
That's a flight away.
Yeah.
We were flying all over the place trying to make things work and things weren't working.
Things didn't work ultimately.
That company ultimately shut down.
It was a great experience.
It was during college and I just sort of fell in love with entrepreneurship.
I didn't know.
Now we're going back to the mid 1980s.
Entrepreneurship wasn't... I didn't even know if it was a word that was why it was
a big thing.
Startup had a hyphen and a... I don't know.
It certainly wasn't a big thing.
None of my friends were entrepreneurs or weren't at startups.
What are you talking about?
Yeah.
The way I described it is my conservative friends wanted to work for IBM and my progressive
friends wanted to work for Microsoft.
That was... I had a computer science degree.
That was the spectrum of what was available back then.
No Google?
I guess Google wouldn't have been around then.
Google was not even incorporated for 10 more years after that.
It was Microsoft was the big one.
Microsoft was new.
That was the startup.
Yeah.
It's like, oh, you want to join this amazing big... It's going everywhere.
It's the next big thing.
Exactly.
Yeah, so I don't know, my school life was not great in high school.
And then by college was started to be focused on entrepreneurship.
Do you think you were an extrovert or an introvert?
I always describe myself as half and half.
But COVID really taught me I'm much more extroverted than I thought.
So it's funny we haven't talked about Techstars yet, but I remember early on in Techstars
we funded a company that was doing group dating where a group of eight guys would sign up
on the platform and a group of eight girls would sign up on the platform and then you'd
facilitate a meeting of both groups.
And so it was less pressure dating.
That's a pretty good strategy.
Yeah.
I like it.
And I remember the CEO was asking me questions about what did I think of the idea?
Well, when I last went on the date, Google didn't exist.
And he's like, what do you mean?
I'm like, it didn't exist.
It was down.
And I'm like, no, it didn't.
It wasn't a company yet.
If you went to www.google.com, we're like, what happened?
I'm like, there's no www.anything that didn't exist.
Yeah, there was nothing there.
So yes, that's the era that I grew up in going to college.
There was no internet.
There was nothing.
There is no cell phone in your pocket.
There was the only newspaper ads for dating.
There were newspaper ads for dating.
But that wasn't considered, it was pretty scary what you would find going out.
It wasn't considered, like my cousin, he's still married to her, but went on a newspaper
ad date.
And we were like, whoa, what are you doing, dude?
You find some scary stuff answering classified ads in the newspaper.
So that was not the way to go dating.
What do you mean by scary stuff?
Was it like scary people?
That's a good question because I never did it.
I don't know that it was so scary what you found.
Maybe I said that wrong.
It just marked you as kind of desperate.
If the only way you could find somebody was buying them off a newspaper ad.
Yeah, that makes sense.
Maybe that's the way it was when dating apps first started as well, where it was like you
were going online to find people.
It was because it's the same version as the classified personal ads they called them.
You're advertising yourself online.
Yeah, and you had to pay money.
You had to pay money to be in the newspaper.
Yeah, and you had to pay money to get an app and do well on it.
When they first started out, they were monetizing it.
Yeah, I guess you have to pay them out.
Now they have all these free tiers.
Do they?
I don't know.
I've been on a date since 1998.
In recent years, people are actually having less relationships and they're having less
sex and fertility rate in the US has gone below the replacement level.
The replacement rate, 2.1.
Yeah.
So what do you think is different about dating now based on what you've seen?
I have no idea.
What are you talking about?
Do you have kids?
That's a good question.
I don't know.
I really don't know.
I do have kids and they do date occasionally, but I can't really speak to how the dating
scene works now.
You want to know how it worked then?
Even then I was like a lightweight, so I don't know that I could describe it then.
Lots of other areas of expertise.
This isn't one of them.
Some people like to plan out a lot of things when they're young for what they want their
lives to look like.
Did you do a lot of that planning?
None at all.
And I always talk about that because I never had a five-year plan.
I never had a one-year plan.
I moved to the United States on three days notice.
I literally got a job offer from a startup in Miami and accepted, flew back home, packed
up all my stuff in my car and drove it down to the US.
That was my plan.
And I think I've always described myself as not having... I think it's really hard to
have a plan.
And I see this now with kids my age, students in college.
There's sort of this desire to know exactly where you're going.
You have a destination.
And that's really hard because can you really decide three years, five years, 10, 20 years
from now where you want to be?
Life is not like that.
Life meanders towards a destination.
And if you have a bit of a sun where I like the brightness over there and this move will
move me in that direction, that's how I've always operated my life.
And so the independence, the startups, the entrepreneurship, the freedom, that was my
son and any opportunity that felt more like... any opportunity that felt like it was moving
me in that direction I took, anything I was doing that felt like I was moving away from
that direction I got out of.
That's all I did.
And so it's a zigzaggy path as opposed to going there in a straight line.
But it's way better than thinking about it and spinning on it for five years and then
trying to zip to the destination, which is impossible to go in that straight line anyway.
So you run your life a little bit like a startup, you would say?
Yeah.
Well, I mean, that's my personality.
Yeah.
You have a vision for something, something leading you.
Yeah.
That's right.
I think that's right.
I know roughly what direction I want to go.
And any move today that moves me a quarter inch in that direction is a move.
Yeah, I'll take it.
Even if it means changing countries or whatever.
I mean, that won't be a big deal if you get to where you want to get.
Right.
Exactly.
It didn't matter to me if I was in Canada, the US or Timbuktu.
Timbuktu?
That is a place, you know.
Is it?
It is.
Where is it?
That is a good question.
Nepal?
Have you been?
No.
Oh.
What do you think made your startup successful?
At least the first one.
Because I've never heard too much about that story.
What made it work?
I think I called the book, I wrote a book on it and I called it No Vision, All Drive.
And it's really the story of starting that business.
I did a second and third edition to include tech stars later on.
Should all the viewers read it?
They should.
I will make a nickel every time you buy one.
I think you can get it on Amazon and I charge as little as it is.
And Amazon will let me.
Because I think it is a good entrepreneurial story.
So I think a few different things.
One is we often talk in entrepreneurship about or people who aren't entrepreneurs often talk
about how entrepreneurs are risk tolerant.
Like they're capable of taking a large amount of risk.
And I always like to say that's not what it felt like.
And that's not how the entrepreneurs that I know are.
They're not risk tolerant.
It's not that they evaluate, oh, the risk is this big and I'm going to take that risk.
They're risk ignorant.
They don't even think about failure.
Failure is not an option.
I'm just going to go for it.
And I think that's what made us successful because we were in our 20s.
We didn't know what we were doing.
We didn't know how to open a bank account much less run a business.
We didn't know how to get customers.
We didn't know how to create software.
We didn't know how to sell.
Go to trade shows, hire employees, get an executive team.
Eventually, we didn't know how to sell the business.
And we did all of those things.
And we just figured it out as we went along because we were too stupid to realize that
we didn't know what we were doing.
And maybe we were lucky enough that we didn't have anyone around us that we cared about
that were telling us we didn't know what we were doing.
And we just figured it out.
We guessed.
We made lots of mistakes along the way.
But in the end, it was a huge success.
And so I can't say any of it was a mistake at all because it was all really great learning.
It was part of the path.
Every step was hard.
Hiring your first employee, creating an employee manual because suddenly you have employees
that are doing weird things and trying to figure out how to keep it within your culture.
So a good story on that.
What kind of weird things?
Well, our very first employee manual had five things that you had to do at work.
And the first one was underwear on the inside.
And there was a reason.
Our first developer always used to come in to work in sweatpants with boxer shorts outside.
That was his fashion statement.
And really, that employee manual was for item number two, whatever it was.
And we had one employee always push the limits on charging on expenses.
I don't remember what the actual policy was.
But when we wrote the manual with the five things, I guess there were four things.
And we're like, we can't make it seem all about this one guy.
So we inserted the underwear on the inside as the first item in the employee manual.
That guy without calling him out.
Yeah, exactly.
It's about the boxers.
But it's a good story, right?
Because it was true.
It's a funny story.
It was true.
The guy was showing up for work with boxers on the outside.
But it was like having that be part of our employee manual was true to our culture of
just being irreverent and having fun at work.
But getting the work done and being serious at the same time.
So whatever those other four policies are that I don't remember, were important.
We created that for a reason.
And then, of course, that grew into a full policy manual over the years.
And I'm sure when we got our first HR director, the first thing she did, we're taking number
one out.
We're like, that doesn't belong there anymore.
That's not staying there.
But then if someone did it again, you'd have to put it back.
But I think the key point there, that's well, yes.
The key point there is that's the beauty of having a startup.
It's yours.
You make of it what you want.
You can be true to your personality and your culture.
And you can have fun at work.
It was a good laugh that we had that in the policy manual.
And it helped us to not take ourselves too seriously in so many other ways.
And I would say it's an example of one of the best things that we ever did was doing
that because it caused us not to take ourselves too seriously.
Did you ever lose it?
The manual?
No, not the manual.
The air of not taking yourself seriously.
I don't think I did.
I mean, so I don't think it.
I don't think I ever did.
There was an era where after we sold the business and I'd left Pinpoint, some other guy took
over and made it much more serious.
And suddenly we're not in Boulder anymore.
We're in Interlochen.
We're in an office park.
There's a dress code and casual Fridays.
And that was the end of the Pinpoint I knew.
So I think the company's-
It was still called Pinpoint at that time.
It's still there, honestly.
It is?
It's still there.
It's not called Pinpoint anymore because we sold it.
It's still on Interlochen?
It's still down in Interlochen.
I haven't seen it.
I'll have to go pass by.
Yeah, it's called Zoll Data Systems now.
Okay.
I've seen the Zoll when you pass by, sometimes like a fire.
Yeah, so that's the company that bought us.
It's a defibrillator.
It's the thing that we start stuff-
I'll see the defibrillators around places and I'll be like, oh, it's David Brown.
That's the company that we sold Pinpoint to.
So they just took your software and they made the defibrillators?
And they made the defibrillators.
Yeah.
So I didn't want to touch on tech stars.
You've seen so many companies go through and either fail or succeed, and there must be
some common things that entrepreneurs fall into.
What are those things?
Well, the way I always answer that question is obsession.
When you find that entrepreneur that's just obsessed with solving their problem, it really
makes a difference.
And the example I always give there is Isaac Saldana, who went through the Boulder program
early on with his company, SendGrid.
So SendGrid is well known today.
They got bought by Twilio for like two or three billion dollars.
They do a number of things, but the original SendGrid product kept email out of the junk
folder, just handled all of the whatever the email protocols were that caused a normal
email to go to the junk folder.
And so think when you go to Uber and you click on forgot password, you don't want the link
to go to spam.
And Isaac and Jose, his co-founder, had worked as developers in a bunch of different companies,
and they were always re-implementing whatever the protocols were.
You probably know better than I do how this works, right?
But they were always trying to solve this problem everywhere they went.
And they said, well, why don't we create a company that solves it for everybody?
And so they created SendGrid in order to do that.
When I met those guys and we got them into the program, I didn't even understand what
they did.
Their company had a funny name.
SMTP API was the name of the company.
Great name.
And they referred to it as SmitaPy.
Oh, God.
We've got to get on SmitaPy.
Isaac and Jose were incredibly technical, and so they explained what their product did.
And I was like bleeding out of the ears a little bit.
Like I didn't even understand it.
And I was there with my co-founders at Techstars, and one of them was like, we've got to take
this company.
I'm like, what do they do?
And he's like, I'm not sure exactly.
But it's something about email, and they care so much about it.
They're so obsessed with it.
And there's a lot of email out there that this is the team to go solve that problem.
And so it was partly the basis of Techstars selection criteria was team, team, team, market
progress idea.
And so team, team, team, are these people part of the team, team, team, are these people
so obsessed with their idea that they'll work day and night on it?
And they were.
And then is it a big market?
This was the next criteria.
Email.
A lot of email.
Huge market.
Like, they had no revenue, they wanted to charge 0.0001 cents an email or whatever.
And because that's all it really cost them to run the protocols, to figure out how to
keep it out of the, to put the tags on, to keep it out of the spam folder.
And during the course of Techstars, we got to the point that it was becoming so popular
that we just told them, like, just double your price every day until somebody says no.
And that's what they did.
Where did they stop at?
And I don't know what the price is.
I mean, it's still per email, it's a small amount, right?
But they now process like 2 billion emails a day or an hour or some crazy number like
that.
Millions and millions, tens of millions, maybe hundreds of millions in revenue.
Huge, huge, huge business.
They process something like, I don't even remember the numbers anymore, 5% of the world's
non-spam email goes through.
So anytime you click on forgot password, right?
It's basically going through.
SendGrid to send it to you.
To send it to you and keep it out of the spam folder.
And you know, many, many of us may not remember what it was like when most of your emails
went to spam.
It was just a pain in the butt.
Now I get emails not in my spam that I want to go to spam.
Yeah, well, that's not good either.
But so back to the, you know, what made SendGrid succeed wasn't necessarily that they had real
strong business savvy.
As soon as the business got going, they immediately stepped back.
Isaac immediately stepped back from being CEO and handed it over to one of his mentors.
And he said, I don't want anything to do with the business side of things.
So it's not that they had an unbelievable business strategy.
They didn't have a pricing model that worked.
They didn't have any revenue to speak of.
It's not, you know, it wasn't any of the other normal things that you would think of as being
so important to start a business.
But man, they got out every day fired up about solving the world's email problems.
And so that's why I think that obsession with the idea is the number one reason by far that
makes a company successful.
It gets you through the lows.
Yeah, because you care so much.
You care so much.
And it doesn't have to be climate change, right?
You don't have to be solving.
You just have to care.
So I don't have to care.
But you care.
Exactly.
You're the one doing it.
So if you don't care.
Exactly.
It's what's going to make you work the 14, 16 hour days.
It's what's going to allow you to keep going when you don't have any money left in the
bank account, when everything seems hopeless.
You know, it's going to make you work harder, hire better people, do all the things that
you have to do to make a business successful.
Have you ever seen anyone not be obsessed and be successful?
Yeah.
I mean, sometimes people get lucky and stumble into a trend.
But I don't think you can count on that luck.
So I think it's the exception.
And then what are common pitfalls for these other companies that don't really make it?
Well, there are many.
I think usually having a co-founder helps.
Solo founders have a hard time.
Partially for the same reason, there's ups and downs in any startup and there's ups and
downs in your personal life.
And when you have a co-founder, they can help you get through.
Usually one's more emotionally volatile and one's more steady eddy.
And the steady eddy person helps the emotionally volatile person get through the downs.
And the emotionally volatile person is usually the one that comes up with the best ideas
during the ups and takes the company in exciting new directions.
And that yin and yang of that two different founder type is really helpful.
Personally, right, when somebody has a down, the other founder can be there to help keep
the company going.
And I also think being CEO of a startup is a very lonely job.
And having a co-founder allows you to have a peer, in a sense.
As a CEO, you never really have a peer because you're at the top of the pyramid.
But your co-founder is the closest thing you have to a peer so that you put on a brave
face for everybody else.
But for your co-founder, you can let the guard down a bit and let them know that you're really
worried about the business failing or your marriage failing or whatever is going on in
your life.
And it's really helpful to have that outlet.
And so I think companies or founders that don't have that are more likely to fail.
What was your darkest days in the startup when you didn't need that co-founder to rely on?
I always think of our darkest days at any startup being at pinpoint.
We had created a prototype of the product.
We were running out of cash.
We had raised $100,000 pre-selling a product to our first customer.
We were almost out of money.
We needed to sell something.
We signed up to go to a trade show somewhere.
I don't even remember where that trade show was.
We thought if we could only get one customer from that trade show, it would sustain us
to the next thing.
I remember we wanted to get a printer or something for $300 and we couldn't afford it.
We were down to nothing.
And we somehow had enough money to rent out a booth and get a spot.
But we knew that if we didn't sign up a customer at the trade show, we wouldn't be able to
pay for it, pay the bills.
That's risky right there.
That was it.
What we didn't know was that this particular trade show, it's usually about customer discovery.
You learn about the different products that are out there.
Nobody buys at a trade show.
In the lifetime of pinpoint, we only ever sold something to at a trade show twice.
This was one of them.
So thankfully, that customer, Bowers Ambulance, they were called somewhere in California,
I was always grateful to them because they believed in us.
And we sold them at that trade show and they wrote us a check.
And if it hadn't been for that, we never would have, we would have folded.
Yeah, it would have been over.
It would have been over.
So what were you planning on doing if you had it kind of hit that?
Failure is not an option.
Risk wasn't a thing.
I was risk ignorant.
We'll just sell something at the trade show.
It'll work.
And it did.
And that's a crazy story.
Yeah.
I mean, and there were probably half a dozen stories just as crazy as that.
Where you cut it off by a tiny edge.
Yeah.
And it was only the obsession that made you be willing to take those risks.
And maybe the risk of ignorance.
Yeah, the risk of ignorance and the obsession.
We're like, oh, yeah, we'll cut it as close as possible.
Yeah.
And then there, I mean, another example was we got funding from our first customer, $100,000
that we had to personally guarantee.
Meaning David, my co-founder and I had to pay back the $100,000 jointly and severally,
it's called.
Which means if he couldn't pay out his half, like we were both in the hook for a hundred.
Somebody had to pay.
It didn't matter who.
And we could work it out between us.
Right?
Yeah.
I mean, we were basically college students and they would have owned our future house,
our future anything.
Right?
And we're like, eh, okay, we'll sign up.
We didn't have anything to lose.
Yeah, I guess you had nothing.
We had nothing.
We're like, take it.
Take my $100,000 worth of my $50 or whatever I have in my bank account.
You can have the rest of my bank account.
Oh.
And then we utilized the business on $100.
So that was the money that we put into the business to get it started at the very beginning
pinpoint.
David put in 50 and I put in 50.
And the way we came up with that number was it was half of the highest of the two of our
savings.
Yeah, you had nothing.
We had nothing.
I mean, that's a great story because you can come from nothing and make a startup.
Yeah.
You don't have to have funding.
You don't have to have all of these things.
You don't have to have all of these other things.
Or a good business plan.
Nothing.
And it was funny because we sold the company to Zold, you know, six years later for millions
of dollars.
And in the balance sheet, there's an entry called paid in capital, which shows how much
money you put into the business.
And it was like $100.
Like it was, it was still there at the $100, right?
It was, I didn't know anything about accounting and I didn't know that that like story would
live on on the balance sheet every time we printed it.
Yeah.
Every time someone looks at it.
$100?
Seed funding.
Seed, yeah, exactly.
A lot of people struggle with entrepreneurship because there might be a lot of beliefs or
insecurities about themselves where when it comes to making a startup, like, oh, people
won't buy my stuff or, oh, I don't want to show up to someone's business and ask them
for stuff.
What was, did you have any of those?
So I didn't really have imposter syndrome, which is what you're talking about.
And it's not just what you described, but it's also this feeling that I don't know that
I should be the CEO.
I'm clearly not qualified.
Somehow I always lacked the, it's not that I had self confidence.
I was delusional.
That's exactly right.
I was delusional into thinking that my 25 year old self knew everything it needed to
know to build a successful multimillion dollar business.
And it's not that there weren't days where I had some self doubt, but they were few and
far between.
As delusional is the right word.
Delusional self confidence.
I have had delusional self confidence my whole career.
Great skill to have right there.
It is.
And I've talked a lot at different trade shows or talks I've given about the difference between
arrogance and self confidence because I do think it's important to distinguish between
the two.
I've always had self confidence.
I did have some arrogance.
I would say that got knocked out of me when I had a failed startup.
Because I don't think arrogance is helpful.
Self confidence is.
And they're like kissing cousins, right?
They're almost the same thing.
Yeah.
It's very hard to differentiate someone who is arrogant and very self confident.
And the difference is humility and maybe the willingness to make fun of yourself a little
bit.
And so the underwear on the inside, right, helps keeping it in the self confidence without
it being arrogance.
Yeah.
Like I'm, I might know stuff, but at the end of the day, it's all fun and games.
At the end of the day, we're all just trying to figure stuff out here.
Do you struggle with anything anymore internally?
You know, I do have that self confidence, I would say.
I mean, I'm sure I do, but in the grand grand scheme of things, no, I feel like I had a
period in my late twenties, maybe early thirties.
It was actually right when I moved to Boulder.
I sort of was rebuilt.
We moved our pinpoint to Boulder.
David, my co founder, was married.
We were still great friends, but we weren't roommates anymore.
I wasn't married at that time.
I wasn't dating.
And it was sort of, I don't want to say lonely, but I had more, I had more alone time.
And I went through this period of what we wound up calling radical self inquiry, like
where you're just introspecting all day long.
I don't know why I did it.
I didn't read a book or something.
I think I was just bored and I had nothing.
I had no one to be with except my own thoughts.
And I figured out who I was and what I was good at and what I wasn't good at and what
I liked about myself and what I didn't like about myself.
And then I remember going through this process of thinking about all the things I didn't
like about myself and putting them in categories of I want to fix this or I don't care.
Right?
Like that's who I am.
Right?
And then put it into the, I'm okay with it.
It's a character flaw, but nobody's perfect.
And that process that I went through in my late twenties, early thirties, I think changed
me for the rest of my life because it sort of put into my past this need to worry about
have I done the right thing?
Am I good?
Am I not good?
And because ever since then, I've, I've, I've felt like I know who I am.
I know what I'm good at.
I know what I'm not good at.
And I'll stick to the things that I'm good at.
Thank you very much.
And, and construct a life around the things that give me joy and happiness.
So you took away a lot of those shoulds in your life.
Yeah.
I should do this.
I should do that.
Somebody told me I should do this or I don't have any, I don't feel like I have any of
those and I don't feel like I had any of those for 30 years.
That's amazing.
Yeah.
I've had those in my life, but not recently.
Yeah.
That's amazing.
One of the traditions we like to have to close out the podcast is we, we get the, the guests
to make a little challenge for themselves.
Something that would maybe make your, your life a little bit, a tiny bit better, maybe
a little bit more peaceful that you could do in like a week or two weeks that would
make a small little impact on your life in a positive direction.
And say it out loud.
Yeah.
You say it out loud and put a deadline on it.
Well, so first of all, I'm not that kind of, I don't need that kind of motivation.
And I have one of those things and I'm not going to get it done in a week or two, but
I'm going to get it done this year.
I can't share it.
And it's on my mind is the biggest life changing thing.
It's basically, it's cutting out one of the biggest time sucks in my life that isn't giving
me pure joy.
It's a side project that I have.
And it's not that it's not enjoyable.
I work with other people who are nice.
It actually generates income, which is nice.
I don't have, there's nothing wrong with it, but it's not in the camp of, I really
love it.
And, and I've made promises to people that I need to keep.
And so I'm going to spend this year, 2024, extracting myself from that.
I'm not going to get it done in two weeks.
No, I mean, that fits the spirit of it.
Yeah.
And I think it's really good to do those things.
I mean, if it were, it could be done in two weeks.
I'd have done it yesterday.
It's just a longer one.
And it's going to free up time for me to do more things that really do give me joy.
Awesome.
Well, thank you for coming on David.
Well, thanks for having me.
Where can people find you?
You can, where can people find me?
If you want people to find you.
I am, I don't have much of a social profile anymore, but if people want to reach out to
me at dbrown at Colorado EDU, that's my CU email address.
Cool.
Very responsive on email.
And you have your book out.
You should read the book.
Yes.
No vision, all drive available on Amazon.
Cool.
But buy it because you're interested in a personal story of an entrepreneur and how
it all worked.
It's not a commercial.
I'm not doing it for commercial reasons.
No.
I'm doing it because-
To get something good out of it.
Yeah.
If people are interested in my story and want to hear more, you can hear about it there.
I think it's a great story.
Yeah.
Fantastic.
Awesome.
Thank you.
Are you in?