Why Startups are Harder than MIT: Stress and the Entrepreneur, part 2 of 2

Published in

The Startup

15 min readJun 22, 2018

This first part of this article, located here, was about why startups are so stressful and how stress accumulates in the body. This part deals with some suggestions and techniques to help deal with the stress of the startup life.

Brad Feld’s First Rule: You aren’t alone.

I was recently interviewing well known entrepreneur-turned VC Brad Feld for my upcoming book, Startup Myths, and I asked him what advice he’d have for entrepreneurs going through stressful times. His first piece of advice was to remember that you are not alone. Many, many people are going through the same thing with their startups, though they may not be out talking about it.

Brad was one of the first in the startup/VC community to talk about depression and the role it’s played in his career. ( (if you haven’t read his blog, it’s atwww.feld.com and worth a read).

I’ve seen that many entrepreneurs may find themselves sliding into “mini-depressions” when they’re trudging along day after day, month after month, and suddenly encounter an intractable problems that they just can’t or don’t want to deal with anymore.

Remembering you are not alone is a great first step.

Talking About Your Problems: How about a CEO peer group

A good second step is to literally not be alone with your problems.

When I was CEO of my very first startup right out of school (in Cambridge, MA), we had a group of CEOs of local startups that met every so often — I think it was once a month or so. I used to joke that this was “my CEO therapy group”.

The group included many entrepreneurs who went on to do great things, including Alex Rigopulos of Harmonix (which years later made the Guitar Hero franchise of games), and Shawn Broderick of Genetic Anomalies, who is now a well known investor.

Being able to talk about things that are going wrong with a group of people who understand and are (or were) going through similar things can be therapeutic in and of itself.

I have to admit, sometimes I would come away feeling much better about my current crisis because someone in the group inevitably would be going through something much worse. For example, I remember once I worried about only having a runway for a few months left, when I realized that one of the other members of the group didn’t have enough money to make payroll this month!

This wasn’t some startup version of schadenfreude– rather it was the first step to putting things in perspective, which can lead to taking your own problems in stride and realizing that rarely is it “the end of the world”, even if it seems like it right now.

If you don’t have a support group like this, informally or formally, it might be worth looking into joining or creating one. I’ve done five full time startups (and many more part-time), so by now you’d think by now I wouldn’t need other entrepreneurs who are going through similar things to commiserate with. You’d be wrong.

One question that comes up here is: Can’t I just talk to my co-founders, investors, or advisors?

Yes and no. I’ve found that even though investors, advisors, and co-founders can be sympathetic, they often don’t understand the stress that a founder/CEO is going through at the moment. Sometimes the thing that you really need to vent or complain about, the thing that’s causing you all this stress, is your investors, your advisor, or even your co-founder!

Please note that most of these suggestions are for relieving regular, on-going startup-related stress. If you feel that you are moving from “stressed out” to the borders of full-on clinical depression, you should think about talking to a licensed mental health professional. There is at least one accelerator I know of that makes each team talk to a therapist as part of the program.

Some Ways to Avoid Stress On a Daily Basis

Part of the problem that makes big stressful situations hard to deal with is that we aren’t “clearing” our samskaras on a daily basis — i.e. we’re accumulating stress and don’t even know it. It’s the little stresses that can add up to something more chronic if you don’t learn to deal with them.

One of my pieces of advice is to have a personal stress mantra that you can have with you every day of your startup journey.

This is not a phrase that you repeat over and over again (like a traditional mantra), but rather a phrase that is available to you to pull out whenever you are getting stressed.

My own personal stress mantra when I am stressed out in a startup is “Watch Star Trek, Walk by the Bay, and Do Yoga”. This stress mantra helps me to have at least 3 different activities I can take on any given day, and by doing them, I find myself demonstrably less stressed out than before doing them. Afterwards, I’m usually ready to jump back in and deal with whatever challenges I might be facing clear-headed.

Everyone’s stress mantra might be different. You might hate Star Trek, not live near the Bay, and find Yoga to be not very interesting, but you can find your own activities. At least one of these should be a physical place you can go that changes your pscho-physical state, at least one should be a physical activity, and the last one can be something more mental (movies, TV shows, books, etc.).

Let’s look more at my stress mantra and decode what’s in it and why:

Taking walks in Nature. There’s a little park in Mountain View, just down the road from where I live and work, and only yards away from Google, that always helps me to deal with stressful situations. It’s called Shoreline and there are paths that are near the San Francisco Bay. When I’m walking there, I can see the mountains mountains to the west (green, tree covered), the water of the bay, and the mountains to the east (which look more like the desert). There is also a nice constant breeze coming in from the bay (OK it’s not always nice- sometimes it stinks lol). The thing is, there’s something about gazing at mountains and feeling a breeze going through your body and energy field that has the effect of “loosening up” the things that you are holding — mentally, emotionally, and physically. What I’ve noticed is that even if I’m holding a lot of stuff in at the beginning of the walk, by the end my body is more relaxed and I’ve let go of some of the things that are bothering me. You can find a place like this in your neighborhood.
Watching Star Trek. This usually gets a laugh when I tell people about it. The truth is that we all have certain types of fiction that not only “take us away” from where we are, but somehow feed our soul. For me it’s usually certain kinds of science fiction or fantasy. For you it may be Sex and the City or Reality TV! Well maybe not Reality TV, but you get the general idea. Find something that you can watch that “feeds your soul”. For me, watching Star Trek brings back memories of childhood and anticipation of great things in the future, and somehow links to something deep in my soul — maybe because I’m an explorer at heart. Whatever it is, take an hour every day to watch an episode of a TV show that does it for you or read something that takes you into this kind of feeling.
Doing Yoga. I’ve already mentioned that the original point of Yoga was to start to dissolve some of the samskaras that we are holding. Too often, in the west, Yoga is considered exercise. I had one Yoga teacher tell me that I’d probably be sore the next day. She was right. I was not only sore the whole next day, which might work for some people, but this kind of Yoga didn’t work for me, but other Yoga made me feel like I was more present and not “holding” onto stress. The Asanas are meant to help you release stress, which as we’ve said, accumulates in the body unbeknownst to us.

While those are the three elements in my stress mantra, you might want to include other related techniques in yours.

Exercise and Physical activity. If you aren’t getting regular physical exercise of some type, then you should. This could be as simple as riding a bike or walking to work. Exercise has chemical and physical effects — while the purpose is different from Yoga, you don’t have to go far to find
Martial Arts. Eastern martial arts are in fact, mediations for the body. If you’re not into Yoga and want something more physical, try a martial art. It doesn’t matter which one, though they all have their different strengths and weaknesses. Whether it’s T’ai Chi or Kung Fu or Aikido, find something that works for you.
Meditation. There are many studies showing that regular meditation has health benefits and leads to stress relief. There are many different techniques of meditation, but at the heart you are trying to calm the mind and the tumultuous thoughts that we are all caught in the middle of. I think of us as one of those snow-globes that has been shaken up, thoughts are flying every which way and it’s difficult to see. A short meditation can do wonders for letting the snow settle down and get a clear view of what’s happening.
Mindfulness: Use Your Work As Meditation. Being mindful at work can have wonders for not only your concentration but on your level of stress. Rather than worrying about “making payroll next month” (which may be a real problem that you have to deal with), when you are writing some code or doing a spreadsheet or having a meeting, focus your mind and attention on the task at hand. I call this “using your work as meditation”. Your mind will inevitably wander. You bring it back. This is just like meditating but it is more about keeping your mind on what you are doing. If you do this right, you won’t be thinking about the million things that “could go wrong” if your startup runs out of money next month. You’ll be thinking about whatever task you are focused on.
Breathing exercises. There are many breathing exercises that can help you to release that which we are holding — i.e. that which is causing us stress. If you are finding yourself unable to sleep, doing a slow breathing exercise is a great way to get back to sleep — almost any rhythmical breathing exercise can work. Here’s a simple one I learned recently: breath in fully (even to places that you don’t normally breath into) expanding your lungs as much as you can, then breathe out fully, much longer than you normally would. Repeat 10 times. After 10 times, hold your breath for 20 seconds. Then start the 10 breath cycle again. If you’re like me, somewhere in the 10 breaths, you’ll lose count of which breath you are on and end up asleep. There are of course many different types of breathing exercises — breath of fire (not recommended for falling asleep), alternate nostril breathing, etc.
Get a Massage. Since stress is being held in the body, it’s amazing how great you can feel after having some body work done. This doesn’t make your stress go away, but it does let you realize that there’s something beyond the stress, so that when you start to feel it again, it ends up being a little less “all-encompassing”.

From an Eastern point of view, as we saw, stress isn’t purely a chemical thing, it is the result of our thoughts, emotions, and our “reactions” to the things that happen to us.

The items in my stress mantra are physical activities I can do on almost any day. They don’t require buying a plane ticket to Hawaii or the Carribean. That’s why it’s powerful to have this kind of stress mantra: You choose one of the things in the moment.

What’s important is that the things you include in your stress mantra have to actually result in a change of state simply by doing them — either physical, emotional or spiritual.

It’s important as entrepreneurs to prioritize these activities and make it as important as your management meeting or product meetings at work. Just as your product might suffer if you don’t do product updates, so will your company suffer if you don’t take time for these things.

Deal with the Underlying Reality of the Situation

When we have a big stressful situation, if we’ve been releasing stress (hopefully by practicing something from our stress mantra every day), we are in a better situation to deal with whatever comes up.

Realizing that we are not alone (Brad’s first rule) is a good first step. But, as Brad told me, the second step is to deal with the underlying reality of the situation.

In short, we still have to deal with what is causing our stress. If it’s that we will be running out of money soon, the business model is not working, or your co founder or team members are not productive, or the market is changing, or the technology isn’t working. No matter how many stress release techniques I teach you, you’ll still have to deal with this underlying reality and find a way to fix it, or to remove the stressful situation, or remove yourself from the stressful situation (we’ll talk about this more in a moment).

Seeing Clearly Is A Problem

The first difficulty here is that while we may see the outer causes of our stress (not enough customers, not enough money) we may be unable to see clearly our own role in causing this outer situation;on the other hand, perhaps we can’t see clearly that in fact the cause of the situation is external to us, and we shouldn’t be taking it as such a personal failure.

Both difficulties are usually caused by our habitual thoughts, which create a conduit of perception that blinds us to the reality of the situation. Entrepreneurs are optimistic people (we have to be, or we would never start a company!) and we see things that other people may not. But sometimes we get tunnel blindness and don’t see things which are obvious to others.

First, our samskaras blind us to our own role in the world of cause and effect. Our perception is warped. I’ve found that if I watch entrepreneurs, many of them often make the same mistakes again and again, sometimes in the same company, sometimes in different companies, and sometimes related to entrepreneurs.

I call these our “patterns”, and they aren’t always obvious to us. Freud once said that the danger of self-analysis is that we are too quickly satisfied with an incomplete answer.

This is true of our patterns. I like to give the example of an entrepreneur who would get a new (advisor, investor, employee) and place his complete trust in that person, ignoring the advice of other (advisors, investors, employees). Inevitably, after a few months of this, something would go wrong, and he would then put the blame completely on the new (advisor, investor, employee) and be adamant that it wasn’t his (the entrepreneur’s fault). Then the pattern would repeat again, with another (advisor, investor, employee). The entrepreneur would always blame others with no awareness of his own role in this repeating drama. That’s an extreme example of a pattern, but we all have them.

Mindfulness, Breathing, Karma Yoga

One of the most effective ways to release stress is mindfulness and breathing. One of the things that mindfulness let’s us do is to focus in on the moment. Two underlying aspects of Yoga and meditation, both of which have been clinically proven to reduce stress, are:

It is impossible to be stressed out in the present moment.
It is impossible to be stressed out if you are breathing fully.

Mindfulness can help you to enter a stress free zone

These are pretty lengthy topics to explore, but as someone explained point #1 to me, “if you are stressed out because you are going bankrupt in a month”, it’s impossible to be stressed out if you aren’t somehow thinking about this future result. It’s only when you pay attention to that future that the stress sets in.

Point #2 is worth exploring on your own. Try it. Holding fear and anxiety are synonymous with not breathing fully and naturally. There are two types of breathing that are impossible to be stressed out with: natural diaphragmatic breathing (watch babies and you will see their bellies going fully in and out with each breath). Most of us don’t breath this way, and it’s because of our holdings in our body that our breath isn’t natural.

There’s also full Yogic breathing, which is a way to fill up the lungs completely, one section at a time.

Of course, even if you do these things, you will find that afterwards, you will feel less stressed, but may settle back into your pattern of breathing and of thinking and holding stress.

This is where the practice of Karma Yoga comes in. Karma Yoga is a practice where you are not so attached to the outcomes of your actions. This doesn’t mean that you don’t try to perform well in every action. Rather, the holding of the samskaras often comes from a set of expectations we have about:

How much money we’re supposed to make
How long it will take to ship a product
How many customers we should have
How many employees we should have, etc.
What others will think of us if X

What would happen if you let go of these expectations? What if your business didn’t have to grow at 100% per year or support 20 employees with VC money?

This process of “letting go of expectations” seems antithical to how we think about startups: we have to have big ,hairy audacious goals, grow big fast, conquer the market, and make lots of money!

What if the start up was an experience rather than a set of achievements? It’s not that you don’t want your startup to succeed — rather what if you could simply look at the results of your actions and the results of the market in a detached way, such that you could navigate the company in a different direction if the results weren’t the right ones without feeling stress by it?

This can only happen if we see clearly, by getting rid of our expectations of what has to happen when, and being present in the reality of the situation.

Removing Yourself from the Startup: “Never Give Up” Is Cliched Advice

If it gets really bad and you can’t find a way to remove the stressful situation, you might have to remove yourself from the situation. The decision to leave a startup can be tough, especially if you have been working on it for years and it is your baby. Sometimes this means resigning as CEO, or it might mean shutting the startup down.

Startups can take a toll on us, emotionally, physically, and unless you are super well funded, financially. I remember one startup that was never well funded which we ran for years but could never pay market salaries. On our key employees (who had a family to support) remarked that it was like “working at an interns salary for five years”!.

And most startups do fail.

While the cliched advice to super-man founders is “never give up!”, the reality is that sometimes it’s better to give up if a startup is wrecking your health or your family’s sanity because of financial reasons.

Sometimes you don’t have a choice. In my first startup, my investors/board of directors decided to bring in an outside CEO and I found myself without a role. The company had gotten too big for me to handle and lead to the next level, they said. While I was upset at first, it turned out to one of the best things that happened to me. I spent the next six months taking time off, living on the west coast and recovered from what had become a greulling stressful experience.

While investors hate to lose money if a startup doesn’t succeed, there is a reason why only “accredited investors” are allowed to invest in startups — they can lose that investment and it won’t affect their overall financial health.

While the startup may fail, it’s only a true failure if you didn’t learn from it.

Entrepreneurs who have run startups are in demand in industry, because you’ll know a heck of a lot more about responsibility, marshaling resources, inspiring people, than someone who’s just had a job. Moreover, you may save your health and family’s sanity, especially if you are struggling financially personally.

Stress and the Entrepreneur

Sometimes I like to think of being an entrepreneur as karma+ plan — i.e. we are accelerating our reactions and building up karmic traces with every stressful situation and our reactions to it. Every new stress creates a new karmic trace, and this is why we can’t sleep or when we do, we so often end up dreaming about our business problems.

This is why I believe entrepreneurs need techniques like Yoga and meditation even more than most people, because the stress that builds up can make our lives hell and being off your game can have much more immediate consequences for an entrepreneur who’s running a startup.

So, the next time you find yourself stressed out, take a deep breath. Remember you are not alone, and there are other startup CEOs going through what you’re going through. You might want to setup a CEO group if you don’t have one. Eventually, you will have to deal with the Underlying Reality that’s causing you stress.

But before the “big stress” hits, have your own version of a stress mantra: Take a Walk by the Bay, Watch Star Trek, or do Yoga!