BRAD FELD – Awareness, Talk to Someone, and Boredom

Ok, since there’s no way anyone’s going to sit through 42 minutes straight here’s clip notes and a full transcript.

6:39 What did you do during the depressive period of the last six months?

12:20 Quarterly “off the grid vacation”

12:46 Digital Sabbath

16:39 Root Cause of Depression – Boredom

20:36 You are not alone – Don’t miss this one!

28:53 Stigma

39:00 Significant Other

Full Transcription


Jonathan: Welcome to My name is Jonathan
Malkin and today, we’re talking with Brad Feld, Managing Director of the
Foundry Group. Co-founder of TechStars and author of several books
including “Startup Life.” Our focus today is on the emotional issues Brad
and his clients face. And most importantly, how to be successful. Brad,
thanks for joining us today.

Brad: My pleasure.

Jonathan: So, to kick things off, I’m wondering. Have you ever run in a

Brad: 23 of them.

Jonathan: And you’re shooting for all 50 states, right?

Brad: That sounded like a setup question. I have a desire to run one
in every state.

Periods of Depression

Jonathan: That’s awesome. So, exercise is definitely something that I
find important, too. I’m in the gym six days a week. All right,
so, let’s get into some of the emotional issues. What things are
you dealing with? What conditions?

Brad: Well, the last six months or so, I had a pretty significant
depressive episode. I’ve had three as an adult. One in my mid
20′s, one in my mid 30′s. I’m 47 now, so, one just recently. And
they were all different, but had similar characteristics in
terms of how I felt. In each of the cases, I had to dig pretty
hard to understand the root cause. The one in my 20′s took about
two years to really understand and process. The one in my 30′s
was probably three months. This was about six months.

Jonathan: So, in each of those cases, was there some kind of trigger or
were you trying to figure out something in life and that brought
you back?

Brad: Each one had pretty significant triggers. The most recent one,
and the triggers typically were physical and emotional of some
sort. The most recent one, I put a beginning around September. I
came out of the summer, I had spent the whole summer in one
place with my wife, Amy. I had written a book called “Startup
Communities” and we started working on “Startup Life.” I had a
really, really great summer. I was probably in as good as shape
as I’ve ever been. I went on a vacation for a week. It was a
bike trip. And I’m not a cyclist. But I ended up having a bike
accident on the fourth day.

And it was a pretty bad one. It could’ve been inches, the other
direction, I would’ve gone over a bridge and a 15-foot drop to
rocks. And who knows what would’ve happened? As it was, I busted
up my chin and broke a tooth and hurt my ribs. But that was kin
of the beginning point. So, I came back and I flew straight back
to New York instead of Boulder. And Amy met me in New York. And
we ended up having about three weeks in New York. Her birthday
was in the middle. So, we had to plan around her birthday, I had
a bunch of work scheduled. And we were working on “Startup
Life,” so we figured we’d just be in this same place while I was
dealing with all of this other stuff.

So, I really hit the ground running hard in September after the
summer where I was away from everybody in the mountains and
working, but kind of chill. And I really didn’t sleep well,
because I had really hurt my ribs a lot worse than I realized.
And if I play it forward, in terms of the dynamics. I got very
tired in September, worked really hard, didn’t feel good, didn’t
sleep well, but just continued to power through.

I ran a marathon in the middle of October. One of my partners, Jason,
ran his first marathon and so, I ran it with him. And I really
hadn’t been running at all, so, I wasn’t trained for it. I can
kind of run a marathon any time I want, but I was really
physically under-trained. And still somewhat hurt from the rib
thing in the bike accident.

I continued to press through October. I had a lot of travel. A lot of
stuff around startup communities, which was the book that had
come out. So, there’s a lot of meetings with random people all
over the country which was on one side, stimulating and fun and
on another side, completely draining. And woven in the middle of
all that was all the normal work that I do as a venture
capitalist with the different companies I’m an investor in. I
made a couple of investments, I had a lot of activity in a
number of different companies.

By the end of November, I had a moment on the road where I was at a
restaurant one night and I went to the bathroom. And my pee was
bright red. I thought I had just eaten something funny, but in
the back of my head, somewhere, I knew something was wrong. I
ignored it, I came back, I continued to sort of grind through
stuff. I was on another trip the next week and our 12-year-old
dog died. Suddenly, two minutes heart attack, painless, but,
sort of all of this stuff mashed together on top of this
incredible amount of intensity. And then it turned out I still
wasn’t feeling good. I went to the doctor, had a CT scan and it
ended up being a kidney stone. So, fortunately, it wasn’t
something more serious than that. But it was a big kidney stone,
it was about 8 millimeters.

And as a result, two days later, I was having surgery to have the
kidney stone removed because there was no way I was going to be
able to pass that kidney stone. So, I had a two-hour surgery
where they put you under general anesthesia. Then I took two
weeks ago. Finally, after three months of this, I just shut down
for two weeks and tried to recover.

And I came back, end of the year, last two weeks of the year in
December. Sort of hung out. Worked a little but mostly just hung
out. And I felt like in January, I was recharged, I was feeling
like I was ready to go again. And I came back and one week after
I came back, I was just done. I just wanted to hide under the
desk and do nothing. I didn’t realize the depths of my emotional
exhaustion as well as my physical exhaustion. And that really,
then, became this depression that really lasted, I thought it
had lifted by mid-February, but it didn’t. And I sort of came
back hard at the beginning of March.

And it really wasn’t until the end of April, third or fourth week of
April that I finally started to feel it easing. It’s been about
a month and every week has been better, now. So, I feel like
it’s finally lifted. I’m giving myself, I have no emotional
attachment to when it goes away. I’m just happy that I’m feeling
better. So, that was the arc of this most recent one.

Jonathan: So, then, what did you do during this last depressive period,

Brad: Say it again?

Relief from Depression

Jonathan: So, what did you do in this last period, here? In the last six
months or so, in this particular depressive period. What did you
spend your time doing?

Brad: Well, I would say for the first three months, in the fall, from
September, I really acknowledged that I was feeling depressed at
about the end of October. So, October and November, I just
worked normally at this incredibly intense pace, which also
included a ton of travel. December, I shut down the travel. I
did very little travel. And I tried to relax a little bit more.
I had a little more time and space to myself. Sleep more,
especially around the holidays.

January started off with just this incredible travel pace, again. And
the same thing with February. So, I really didn’t ratchet back
what I was doing. And if anything, I sort of have this
commitment for the rest of 2013 to significantly travel.

By the end of February, middle of March, I was really feeling like I
just needed to change some stuff. So, I cancelled a bunch of the
travel that I had for 2013. And, actually, in April, I decided I
wasn’t going to travel anymore in 2013. So, I had some travel
that finally finished up about a week and a half ago. So, I had
some commitments that I had to finish up. But from today,
forward, through the end of the year, I have no travel planned,
except for two vacations. So, that’s really significant because
for the last 20 years, I’ve probably spent 50 percent to 75
percent of my time on the road.

Jonathan: Okay.

Brad: I changed a bunch of tactical things in the last 60 days. So, I
have consistently gotten up from Monday to Friday at 5:000 a.m.
No matter where I am, no matter what time zone it is. I have a
routine that’s a morning routine from 5:00 to 9:00-ish or so.
And then, I have these very full days from 9:00 to the end of
the day, 5:00 or 6:00. And then, typically, there’s something in
the evening that’s work-related, as well.

And what I decided to do was wake up when I woke up. So, I changed
the morning cadence. And I found that even after a month of
sleeping, instead of the six, seven hours a night that I
typically slept, I’m still sleeping eight, nine hours a night,
so I’m still very physically tired.

I did some other tactical things. I stopped drinking coffee, I
stopped drinking booze. I realized that I hadn’t been running
nearly as much as I had before because I was still beat up from
the bike accident. And that I hadn’t really felt like running in
the wintertime. Just for whatever reason, the combination of the
winter, plus being depressed. Just struggling through it.

So, I started running with more consistency and focusing. Just
getting outside more. And then I’ve always been pretty good at
blocking out the distractions and compartmentalizing, but I was
feeling overwhelmed. I get 500 e-mails a day and I had this ego
attachment to responding to all my e-mails. And I really just
decided to figure out how to cut that back. And so, I got off a
bunch of lists that I was on. I decided that I wasn’t going to
respond to stuff that I just didn’t feel compelled to respond
to. And just try to get myself a little more space in this. So,
this was on the front end of it.

And as part of that, I also started thinking really hard. Not just
tactically, right, the tactical stuff is easy. But what are some
broader arc things that both causes a depressive episode as well
as cause me to sort of regroup.

Morning Routine

Jonathan: So, one thing I definitely pulled out of that is the running.
So, we know the exercise definitely helps with the depressive
side. So far, it’s the one thing that science has said
consistently helps with depression. I think they’ve said over an
eight-month period they’ve done studies, it’s the one thing that
consistently has outcomes over that period. So, I’m sure that
that certainly has helped with things.

But I’m curious about the morning routine. I have a similar routine.
It takes me three hours to get up in the morning. So, I get up
at 6:00 and I go to work at 9:00. What kind of morning routine
were you doing?

Brad: Well, historically, it’s been very consistent. So, I get up at
5:00. I work at my computer until about 6:30 when my wife Amy
wakes up. When she wakes up, we do this thing called “Four
minutes in the morning” which I talk about in the book “Startup
Life” where I stop whatever I’m doing when I hear her getting up
and go spend four minutes with her. Just make a cup of coffee
together, make a cup of tea, whatever.

So, the first thing she sees in the morning is not me huddled over
the computer, but it’s actually the two of us just interacting
and waking up. Then, I’ll typically go for a run. And then
eventually, take a shower and go to work. So, that was the
pretty consistent cadence of the morning.

What I’ve done now is I’m not scheduling anything until 11:00. And
so, I have a lot more time in the morning to do more stuff. To
do more catch-up, to do more of the writing that I’m doing. I’m
trying less to cram it all in. Or to have some more space to
work on some of this stuff.

Digital Sabbath

Brad: Another example of a thing that I’ve done that’s tactical in terms of
trying to give myself some space is a change of routine. I’ve
pretty consistently worked seven days a week and then once a
quarter for a week, I go off the grid. So, I do what Amy and I
call a “Cue expectation.” So, each quarter, we go away for a
week. On Saturday, I give her my iPhone, she gives it back to me
the following Saturday and we go somewhere. And I’m just
disconnected. And we’ve done that for a dozen years, not. It’s
been really awesome. And we miss once a year, sometimes, we miss
a twice a year, but oftentimes, we do all four times a year.

What I started doing in March was doing a digital Sabbath. So, Friday
night, I’m not religious, but sort of using this concept of a
Sabbath. Friday night sundown, I turn off my phone and I turn
off my computer. And I don’t touch anything electronic other
than the TV or whatever. But I don’t do e-mail, I don’t check my
phone, I don’t text until Sunday morning. So, I give myself a
very significant 36-hour break from it all. And the first thing
I noticed was that on Sunday, all the e-mails that came on
Saturday were still there on Sunday.

Jonathan: Right.

Brad: All the shit is still there. So, that’s fairly obvious. But
there’s something about it. I told my partners that I was doing
this. I sort of broadcast to the entrepreneurs I work with that
I was doing this. And the first couple of weeks of doing that
were really a hard shift. Partly because I was so depressed and
still struggling with all this stuff.

About the third or the fourth week, I was really enjoying having
nothing planned on Saturdays. And not feeling any attachment to
the computer or to responding to things or to schedules and just
kind of doing whatever. And I’ve now done that for maybe three
months. And I think this is a new lifelong habit. I think this
had a really significant impact. Because I find myself on
Wednesday or Thursday, looking forward to Friday night.

Jonathan: Let me ask you this. One of the things that a lot of people
have, whether they’re depressed or not, pretty much everybody
nowadays, is that obsession to checking your e-mail, your
Google, Facebook, all of your social networks. So, with taking
that day off, you find that through the rest of the week, you’re
a little bit less compulsive with all that checking of things?

Brad: Yeah, much less compulsive. And it’s not just compulsion, but
it’s focus. One of the things that I’ve always been pretty good
at is carving out time when I need to focus on something else.
So, you can’t write a book while you’re answering your e-mail.
That’s impossible. So, if I’m going to write, I’ve learned that
I can’t write productively for more than four hours a day. And
so, if I’m going to write, I get up at 5:00 in the morning and I
write for the first four hours of the day.

When I’m working on a book, that’s what I’m doing. When I write a
blog post, I’m not trying to do a blog post in-between meetings.
I just write a blog post first thing in the morning when it’s
quiet and I’m still in that sort of waking-up phase.

What I found during the week was, by not feeling like I had to check
stuff all the time. Or by even giving myself this day off of
checking stuff, I’m even checking stuff less frequently
throughout the day. So, if I have periods where I have lots of
meetings going on, you know, in-between the meetings or in-
between phone calls, I’ll check my e-mail and do a quick
response to whatever’s there. But it’s a very different dynamic
than when you feel like everything’s stacked up all day long and
you’ve got no freedom around it.

And so, until 11:00 in the morning, I’m not really checking my e-mail
very much until 11:00 in the morning. I’m doing things I’ve got
to do. But maybe I’ll check it once an hour just to see if
there’s anything I’ve got to respond to. But then I’ll feel a
compulsion to respond to it.

I also did disconnect, not electronically disconnect, but I stopped
engaging with a lot of the social network activity that I was
engaged with. During this period, just to try and give myself a
break from it. I’ve never been a very heavy Twitter user and my
tweets go through to Facebook. But I don’t spend a ton of time
on Facebook. But I do spend a lot of time checking out our
FourSquare and I’ve generally spent a lot of time on LinkedIn
responding to requests and things like that.

But I gave myself some space from that and what I found was by giving
myself some space from that, I’m actually somewhat interested in
dealing with it again. Rather than where I was before where it
just felt like this endless grind of information. And I knew
that the endless grind of information was not actually feel more
interested in what I was doing. It was leading to something that
was, in essence of this latest depressive episode, just now
getting to some root cause, which was real boredom. Let’s talk
about that for a minute.


When I thought about the other two periods in my life when I had
depressive episodes in my 20′s and my 30′s, boredom was part of
it. The interest of what I was doing had flipped from 80/20.
Where 80 percent was really stimulating and 20 percent was
routine and boring. To the other direction where there was 20
percent that was stimulating but the vast majority of it was
boring. It was routine. It was challenging but it wasn’t
challenging in the way it was compelling.

And then what happened this period of time, I had a huge amount of
work. But 80 percent of the work felt routine. I was spending my
time on stuff that wasn’t really challenging me, wasn’t
stimulating, wasn’t that interesting. And I was able to, in very
short order, once I recognized that, change a lot of my own
patterns that I was spending much more of my time on the stuff
that was interesting.

And you don’t flip back to 80/20 right away, but you can at least
look at it and get back to 50/50 just by saying “no” to a bunch
of stuff that’s boredom.

Jonathan: That’s excellent. Boredom as a factor in there. I can see where
that has applied in my life, as well. I kind of went through
somewhat of a period with that recently. I took off, took a
sabbatical, traveled for a while. And I actually found on my
travels that I got bored at some point. And the only things that
were really important were coming back and building a community.
Friends and family and the people around me. And I figured out
that I could move somewhere, live somewhere, anywhere, and do

So, I figured out I didn’t really need to travel anymore to do that.
And workwise, I came back and said “Well, I’ve been traveling
with no work. I really want to go back to work.”

Brad: Right. For me, it’s part of the fascinating dynamic. For 20
years, I’ve traveled a lot. And me and my wife Amy were talking
about it at lunch today. That the way I’ve approached work has
been with a lot of travel. And I happen to live in Boulder,
Colorado which I absolutely love and I love being here. And I
don’t really understand why I felt so compelled to travel as
much as I’ve traveled. I can rationalize it in terms of the way
I’ve approached the investing that I’ve done and the work that
I’ve done.

But it’s not really internally consistent. Like, I have control over
where I choose to travel and how I choose to travel. And so, I
really have it let it be the default. Rather than “I need to go
do this trip because I want to this trip.” It’s “I’m doing this
trip because somebody asked me to or I felt like I was obligated
to it or well, I’ll just do it or I scheduled it, so I may as
well follow through on it.”

When you relax that constraint and you get rid of all of the energy
associated with travel, let alone the time, all of a sudden, you
start to look at how you’re spending your time and there’s a lot
of really interesting things that you can and should be doing as
an entrepreneur, as an investor, that get, sort of, muddled up
with all the running around, travel stuff.

Jonathan: Sure. So, let me ask you now. With the folks that you work
with, so you work with lots of entrepreneurs. You’re on boards,
an investor and so forth. Do you see similar, and, is that your

Brad: That’s Rex, yeah.

Jonathan: He sort of wandered through. That will make the video viral at
this point now that an animal has jumped through.

Brad: Hey, Rex. What’s up, man?


You Are Not Alone

Jonathan: So, with some of the folks that you work with. I was talking
with Cameron Harold earlier this morning. And he mentioned, he
really likes to quote that “Bipolar is the CEO’s disease,”
right? And it’s just a different way of approaching things that
really works for entrepreneurs and executives. So, have you seen
that? In the folks that you work with, have you seen some of
these issues in the entrepreneurs that you work with?

Brad: I think a lot of entrepreneurs struggle with depression or
different types of anxiety disorders. And I think they don’t
feel comfortable talking about them and our society tells you
that this is bad. And if you’re a CEO, you have to be strong.

If you're an entrepreneur, you have to always be doing great. It's just bullshit.

It’s not how people are actually doing. And so,
you put this other layer on top of what your real emotions are
and you suppress your emotions even more.

And my relationship with the people I work with, the entrepreneurs
I’ve invested in, my partners. I try to have it be very open and
recognize that any entrepreneurial art has lots of ups and
downs. And the ups and downs aren’t just about success or
failure of a company. They’re also about how you feel and how
you’re dealing with stuff at any particular point and time and
how you’re processing the stress, pressure and anxiety.

And the notion that those things are something that you can
compartmentalize and ignore. That’s not really true over a long
period of time. You might be able to compartmentalize and ignore
it for a period of time. You’re in the midst of something that’s
incredibly stressful and incredibly high-anxiety, you’ve got to
focus on it. And then you get through it. Then, whatever
suppressed emotions you have are going to surface anyway.

And so, I think typecasting it as a thing like “Entrepreneurs are
bipolar. Entrepreneurs have OCD. Entrepreneurs have ADHD.” I
don’t buy any of that.

I think everybody has their own complicated emotional makeup and their own brain chemistry and their own things that work and don't work.

And I think putting a label on it is an error. I think the more important thing, as a
person, as an entrepreneur, is to try to start to understand
yourself and how you respond to these things. And what you need
to do to be able to be both high-performing and happy. You can
be very high-performing and very unhappy.

When I was depressed in my 20′s, I was CEO of a company that ended up
being up very successful and during that period of time that I
was struggling through this two-year period, the company was
very successful. We were very profitable and we grew. It was a
good business. If you talked to any of the people around us,
they might say “Eh, it seems like Brad’s having a bad day.” They
wouldn’t have identified how I was doing because I hid it. I
suppressed it. And that, I’m sure, elongated how long it took.
And, really, subsumed a lot of my energy.

I’d get up in the morning and I’d use all of my energy just getting
through the day and being an effective entrepreneur and an
effective CEO. And then I’d come home and I’d have nothing left.
I’d sit in the bathtub, I’d lay in bed and do nothing. And
that’s not a way to live. I shouldn’t say that. It’s a way to
live. It’s not a particularly satisfying one and it’s not one
that I think actually gets you as a human to a place where you
enjoy this experience called life to its fullest.


Stigma – Talk About Your Depression

Jonathan: Yeah. Well, that’s the one of the things I hope with these
interviews is that entrepreneurs will see this and understand
that other people are going through it. It’s not that big a
deal. It’s something for them to deal with, but it’s not
stigmatic or a problem, necessarily. It’s something that they
just have to deal with. I’ll tell you in my own experience, when
I started telling people about my bipolar and depression and
being suicidal in 2001, people are actually very responsive.

Usually, the response is one of two things. It’s either they just
don’t care, they’ve got their own lives. It’s like “Okay,
whatever.” Or the other one is they open up and tell me
something private about themselves. Whether it’s depression or
something else that they typically don’t tell people. So, I’ve
been very surprised. I thought there was a stigma around it. But
once I started telling people about it, like I said, it was
either no big deal. They could care less because they’ve got
their own lives. Or, they opened up and told me something
they’ve been dying to tell people forever, anyway.

Brad: I share that experience. I think stigma is a good word for the
label or the view that so many people have about this stuff that
causes one to not be open about how they’re actually doing. I’ve
been open about this. I’ve written about it on my blog a fair
amount. I haven’t tried to hide my own struggles. I tend to be
very open in terms of what I write about and how I talk about my
own journey. To not include this in my own journey would be
basically undermining, Steve Colbert might say “The truthiness
of it all.”

I’ve been pleasantly surprised by the number of people who have
reached out to me. Both people I know and people I don’t know.
Not just said this was helpful. My being open was helpful. But
actually articulated what they were struggling with. And the
mere fact that a person would articulate it to another person
often is incredibly helpful.

Because the starting point is just acknowledging that you're struggling with something.

Like, it’s easy to have it echoing around in your brain. But until you put
it out there, even just to one other person. You’re not really
doing anything that’s active about trying to address it. And I
think that’s been powerful.

When I started talking about it openly, I had no expectation of
positive or negative benefit from it. In other words, I wasn’t
worried about a negative issue around being open. I kind of
don’t care. From the standpoint of, if somebody wants to try to
use it against me, okay, whatever. But I didn’t have any
expectation of a positive benefit for me. And it’s been powerful
and fascinating in that it hasn’t really been a positive

In other words, by being open and sharing for myself, it’s been a
positive benefit to others, but it hasn’t really impacted how I
felt that much. What has happened, though, is that by being open
about it, it’s caused me to talk about it more. To get actually
bored of talking about certain aspects of it. Which I think got
me more quickly to this notion of boredom was at the root of it.
Yes, I was exhausted physically, I was exhausted emotionally,
but I was also spending my time on a bunch of stuff I was that
interested in anymore.

And I needed to get to that point. And I did get it to that point in
a pretty quick manner. Because I think the 19th time you have
the same conversation, you realize that the tape that you’re
playing is not that interesting. It’s like “All right. What’s
actually going on here”?

Jonathan: Right, right. Yeah, trying going to a foreign country with a
new language. You’ll have the same conversation a lot more than
19 times. You learn one conversation that you can say at a party
and then, you run your 200 words and then you’re done. It’s how
you get started. I spent some time in Brazil learning
Portuguese. I was okay in some situations and others, not so
much. But let’s get on a pretty serious topic with some of the
recent suicides that occurred.

So, Aaron Swartz, Jodie Sherman and some others have actually
committed suicide in the last few months. And so, one of the
things that is important to me is figuring out how can we keep
folks alive? Whatever the issues are, if it’s anxiety or
depression or anything else, we can help you if you’re alive,
right? There’s one thing we can’t do is if you’re not alive
anymore. We can’t do anything for you. So, anything you think we
could do to reach out to these folks in their darkest times to
help keep them alive?

Brad: I think the most important thing that entrepreneurs and leaders
 in and around entrepreneurial circles can do is essentially destigmatize depression.

Make it okay to talk about. Make it a topic that’s important to understand. A lot of people
who have anxiety or struggle with stuff or have real pressure
don’t have depression but others do.

And depression is a mental health issue. It's no different than any other disease that one
 would have. Breaking an arm or breaking a leg. My wife just got her appendix out.

These are all things that our physiology, our body, both physically
and otherwise, have to cope with. And I think that the notion
that, as a CEO or as an entrepreneur or leader, you have to be
tough and you have to be strong. And you can’t show weakness. I
think for somebody who really is depressed, makes it even harder
to cope. And I like to describe to people, there’s phases of a
depression that I experience. One phase is one that’s
excruciatingly painful. Everything is painful. And there’s a
phase where everything is joyless. There’s just no joy in
anything. And they’re different.

And in each of those two cases, depending on what you’re trying to
do, the pain that you’re struggling with, or that I’m struggling
with, becomes excruciating. To the point where it’s emotionally
excruciating and almost becomes physically excruciating. Like
you just really can’t, it takes so much energy just to cope.
When things are joyless, it’s in the absence of recognizing that
that phase will end, it feels interminable.

You’re in this joyless phase and it feels like if the rest of my life
is like this, it’s not worth it. So, those two constructs, this
notion of extraordinary emotional pain that borders on physical.
And this notion that if this is what it’s like for however long
this time stretches out in front of me, I can’t deal. Those are
the things that, if you know it will pass. In other words,
having gone through this in my 20′s and having gone through this
in my 30′s and having spent time with it, I know it will pass. I
don’t know when it will pass or why it will pass, but I can cope
with that.

But for somebody that really hasn’t had the ability to run through
the whole cycle. They’re in their 20′s, dealing with it for the
first time like I was. I was really fortunate that I had a good
support system there. Between my business partner. Amy had a
good psychiatrist, sort of all of these things. My brother, who
was incredibly close to me at that time, he was just supportive.
A couple of other friends who put up with me and listened to me
and were supportive. That allowed me, even though I didn’t want
to share very broadly when I was in my 20′s, at least I had some
people to talk to.

Now, I get through that cycle and I’m in my 40′s and it happens
again, I’m like “All right. I’ve got it. This is going to suck
for a while. I don’t really know what that means, I don’t really
know what a while is. I don’t really know what parts of this are
going to suck.” But I do know that it has lifted before and that
I’ll get back to a happy place and a place that feels like my
normal self.

I think that the more successful people who can be open about their own struggles, especially with the next generation of entrepreneurs, the easier it is for entrepreneurs to recognize that this is okay.

It’s on the border of the same thing. If you’re an artist or a
musician, you have so many examples of people who have this
creative drive that’s mixed with this emotional torment. I think
that many entrepreneurs, many incredibly innovative thinkers,
struggle with the same thing. It’s a different manifestation,
it’s a different socialization, now. But instead of allowing it
to be okay within the entrepreneurial lands, the entrepreneurial
society, it’s not okay. That’s for musicians, that’s for
artists. That’s not for us. And that doesn’t really work,
either. Because it’s the same kind of dynamic where you’re
pushing ahead into a future that people can’t envision, don’t
understand, don’t see.

You’re doing things all day long that don’t work or people tell you
that you’re crazy or you struggle with them. Impossible odds if
you try to do things that make no sense to most people. You take
that risks that are uncomfortable for even the sturdiest of
people. And yet, you have to be tough and strong through it all?
Come on. Give me a break.

Jonathan: Maybe some of that will be changing a little bit. Certainly
some business is becoming much more personalized. You can
certainly see that in what you’re doing. A lot more wrapped
around your personality and your life story. Your business
becomes a lot more about your story than ever before, really.
So, maybe in that situation, folks will be able to open up a lot
more because it’s actually beneficial to their business that
they show these things in some sense.

And I think listening to, I always like to come around in these
interviews and think about what solutions I’ve heard. So, one of
the big ones is with stigma and awareness that I heard from you.
So, definitely, the more that you and I and everybody else
publishes about how they live and how they do things. And not
just necessarily problems, but how they solve them or how they
go through them or how it’s not necessarily even a problem. It’s
just “Here’s what I do day to day.”

And that will help a lot of folks just by being able to see that and
tune in to the fact that, here’s some examples. Other folks that
are doing the same thing that you are. Going through the same


Social Support

Jonathan: Another one I heard is definitely that social support. So, there’s a
certain aspect of awareness where people know that this is an
issue that they’re going to have or it’s okay to have it. Then
there’s also, that’s not always enough. If you’re in a deep
depression, just knowing somebody else has been there doesn’t
necessarily help you. You really need somebody else that you can
go communicate with.

And I don’t know if there’s necessarily anything out there where it
makes it okay for an entrepreneur to reach out to another
entrepreneur and say “I’ve got $17 million on the line and I’ve
got 50 people counting on me to keep them employed and I’m going
through a severe episode here with all that’s going on. And I
don’t know how I’m going to get up tomorrow morning and do all
of this.”

I don’t know that there’s really an outlet for them to go reach out
to somebody and do that. Do you know of any way or mechanism

Brad: I don’t think there’s a specific outlet. But I think that
there’s receptivity from people who are open about. Myself, you,
others, to try to be helpful. I think there are a lot of an
increasing number of CEO and entrepreneurial coaches who have
been successful entrepreneurs. These are different from mentors.
So, an example of a person I would give is Jerry Colonna. He was
a very successful venture capitalist. He struggled very openly
with depression. He eventually decided to stop being a venture
capitalist. Took a couple of years off and went on his own
exploration and reinvented himself as a coach and a CEO coach.
And he may be the best CEO coach I’ve encountered. He’s a dear

But just remarkable in terms of being able to go between all the
different issues that somebody who is a CEO or an entrepreneur
is struggling with in the context of this. And the end result of
it, for the entrepreneurs. Somebody like Jerry is at capacity
all the time, but he has a broad network of other people who are
very sensitive to the issues that entrepreneurs face and can be
very helpful in those contexts.

So, I would put it in a couple of levels. One is, your peers are
always going to be a phenomenal source of help and support. And
being open with your peers, some of your peers, you’re going to
get a spectrum. You’re going to have some peers, as you’ve said
who don’t care. They’ve got their own shit. And then others who
say “Yeah, I’m struggling with that, too.” Or “I struggled with
that and here’s how I got through it or here’s how I dealt with
it or you should go talk to this person.”

The next layer up is mentors and being open with your mentors, the
people that you really view as mentors. Some of them may be not
helpful at all. “Hey come on, Brad. Just get over it. You’ve
just got to power through it.” All right. Check. That person is
not going to be helpful. But same kind of thing. And even the
mentor who isn’t helpful has your best interest in mind if
they’re a true mentor. So, they’re trying to be thoughtful to

And then, getting a coach that has experience with entrepreneurs that
have struggled with this. Different than a therapist, but in a
lot of ways, the same kind of characteristics that you would get
from a psychologist. Not a psychiatrist, but a psychologist. And
then, of course, if you’re really in a difficult place. If
you’re contemplating suicide, if you’re thinking about hurting
yourself, you have to do something active in those moments with
real psychiatric help. Your business colleagues and your friends
and your mentors can’t help you.

We have in the “Startup Life” book. Under the section, we talk about
depression. If you’re at that state, get real help. Because
that’s the only place that you’re going to be able to have
somebody help you navigate out of that. You might be able to
navigate it out of yourself, that’s very dangerous.


Your Significant Other

The person I left out of all of that, of course, is your significant
other. Amy has been incredibly helpful to me in each of these
periods. And I think that most partners, most significant
others. If you try to hide this from them, you’re doing both of
you a disservice. Because it negatively impacts your
relationship as well as you.

It’s important, though, to recognize that it can wear out your
partner. Amy and I have very clear sets of rules around things.
For example, we have a set of rules around any sort of suicidal
ideation that I’d ever have. Because that’s not something she
feels equipped to deal with. And the rules are very well-
defined. If I have any sort of suicidal thought, I have to stop
what I’m doing, I have to share it with her immediately. And
then, we decide what to do from there.

The other thing is, she’s allowed to tell me that she’s getting
tired. I’m wearing her out. She needs a break. She needs some
space just to sort of regroup because she’s putting a lot of
energy into me during this period of time. And I try to be very
understanding of that. I’m super appreciative of it. But when
she’s getting grumpy or she’s getting tired, she needs some
attention for herself. It can’t always be about me, even if I’m
in this joyless state. Where I have to then pay some attention,
I have to put some of the energy back into her and into the

Figuring out with your partner when you’re struggling with depression
or anxiety is important and also recognizing your partner may
struggle with the same thing. So, if you’re both struggling with
depression at the same time, it’s very hard to help each other.
At one level, at some other level, there’s some reason why
you’re both there. And actually talking openly about it versus
trying to spare the other person from what you’re struggling
with can, in a lot of ways, be very helpful in terms of it

Jonathan: Yeah. That’s great that you have that support there. I’ve
definitely heard from other entrepreneurs. I know some folks
here, locally, particularly in St. Pete, some of the people I
interact with. They definitely said where having that other
person there helps them tremendously. And I know there’s lot of
folks like myself that say “We’d love to have that.”

But thank you so much. I think we’re out of time here. There’s a
thousand other thing I could ask you. I could spend another hour
asking you about things, but that’s our time for the day. Thanks
so much. My viewers and I appreciate it very much. Thanks so
much to you for coming out.

Brad: My pleasure.

Jonathan: Brad Feld. Managing Director of the Foundry Group, co-founder
of TechStars. And author of several books including “Startup
Life” which we talked about. Thank you very much.

Brad: Thanks for doing this. I think it’s great.

Jonathan: Take care.

Brad: All right. See you.


  • Awareness – Just knowing other entrepreneurs have similar experiences.
  • Talk to Someone – Three types: Peers, Mentors, and Coaches
  • Boredom – sometimes depression is due to boredom.  Find your passion!


About Brad Feld

Brad Feld

Brad is managing director of the Foundry Group, co-founder of TechStars, and author of several books including StartUp Life.

Shouts Outs

Jerry Colonna 

Jonathan Malkin (98 Posts)

I am a journalist specializing in helping entrepreneurs overcome depression. I overcame depression by figuring out what works in traditional and alternative treatments and by implementing over 100 techniques to improve mood, energy, and focus. Successful entrepreneurs are crushing it at work and suffering at home. shares the specific techniques entrepreneurs use to turn personal struggles into public triumphs. For twelve years I thought I'd spend my life miserable and alone. I want to make sure no one else ever has to go through twelve years of pain like I did. I am known for inspiring entrepreneurs when they need it the most. Entrepreneurs leave feeling optimistic.

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