Staying Sane When Co-Founding

I spent 5-years at Amazon and I enjoyed the experience tremendously. Amazon is known for a bruising, rough culture as summarized in Kristi Coulter's memoir "Exit Interview" so I sometimes wonder if the root cause of my positive perception of Amazon is at least partially my unemotional, analytical personality - very few things bother me and I find it easy to disassociate from "business". So, there were challenges and situations I was less than happy about but generally I left so much better than I arrived.

The above is to give context to this statement: soon after I co-founded symphonie.ai, I discovered that co-founding a start-up is at least an order of magnitude rougher than whatever my worst day at Amazon might have been. I never once doubted my decision to join Amazon from the first day to the last day. In contrast, more than once over the last 18-mo I have looked in the mirror to ask the person staring back: "Remind me again why am I doing this?"

Co-founding a start-up is emotionally draining even for someone with less than average emotions - and for someone who isn't taking outsized financial risks in doing so. I cannot imagine how much more emotionally draining it would be if you were betting everything the way Jeff Bezos did when he founded Amazon.com (and the way many, many other people do when they start this journey). So, this post is about sharing with you why this is a difficult journey and tips for keeping your sanity along the way.

There is a lot of downside in all that upside

The upside of co-founding a start-up include:

1. It can be financially rewarding if you are in the tiny minority of start-ups that succeed - the United States (US) Bureau of Labor Statistics (BLS) estimates 80% of start-ups fail within 1-year
2. You are your own boss with the caveat that "not really" because you still answer to customers and investors (if you have any) and by extension to employees (you might be the boss but no one has to work for you)
3. Your work is presumably more professionally and personally satisfying (if this is not true, you need to reconsider your start-up idea)

Those things sound like great upside. But with all that upside, comes downside:

1. You are very likely to fail and you will have no one to blame but yourself
2. Going from 0️⃣ ➡️ 1️⃣ (i.e., "zero to one") is extremely slow, frustrating, time-consuming, and resource-consuming
3. As the start-up matures, the fun and interesting aspects of "be your own boss" and "do something more rewarding" will erode away so that you're back to "its a business" that requires you to make similar compromises and spend time on similar "not interesting problems" you had when you were working for "The Man" – except now YOU are "The Man"

All this downside causes what I consider real mental health challenges that you will have to learn to overcome or at least manage effectively. To borrow a famous World War II British motivation poster:

No One to Blame but Yourself

This is by far – in my opinion – the most challenging mental health aspect of co-founding a start-up: you are responsible for what happens. When we work for someone else, whether a small or large business, we spend significant time complaining about bad decisions made by our boss, their boss, the VP, the CEO and so on. There is a "protective blanket" we can wrap ourselves in that tells us whatever went wrong was not "our fault" it was someone else.

When you co-found a start-up, you have no such "protective blanket": it is all on you. Intuition tells me this "ego busting" feature of a start-up is one of the primary reasons most people never try it. It is very hard to get up every morning, accept mistakes you made, identify a solution, and execute – knowing that the next day will have a similar Sisyphean feeling. That said, even worse is never acknowledging a mistake – a surefire way to drive your start-up off a cliff extremely fast.

These things help me handle this downside and they might be helpful to you:

1. Remember this is a two-way door decision — you can always change direction up to and including taking another job. The lifetime of skills and experience you’ve built gives you other options. It’s not the end of the world.
2. Listen to a lot of music — whatever genre you like. I got into the habit of listening to Eminem during my most difficult days because a lot of his music is about overcoming adversity.
3. Remind yourself that you are doing something difficult. If it were easy or obvious, someone would have done it by now. The challenges you encounter every day are a normal part of the process of co-founding a start-up. Mistakes too are a normal part of the process: identify them, own them, solve them, and move on.
4. Take long walks and don’t think about your work or what you have to do — I try to take a 45-min walk every day and admire my surroundings in the Pacific Northwest (PNW).
5. Call other people on the phone and catch up with them. Talking with others helps clear the mind and recenter yourself. I often combine this with my walks — either by taking my co-founder on my walk or calling 2-3 people I know to catch up for 15-20 minutes with each.
6. Take the weekends off unless absolutely necessary to catch up on a critical task. Some people advocate working 24/7 non-stop – "hustle culture" – as the only way to succeed. I think that is nonsense because if you are exhausted it is difficult to make good decisions. You will have to work hard, but that is not the same as "killing yourself" without time to recuperate and clear your mind.

Zero to One

Before I co-founded a start-up, every place I worked at – no matter how small – already had a working email system, benefits, office space, business software, bank accounts, et cetera. You kind of take it for granted that someone else has set-up the basic things you need to do your work. Although it has gotten much easier, you would be surprised how long it takes to set up basic things even with modern technology tools and services. When I set up our email system with our @symphonie.ai domain, I had to debug why our emails were getting caught up in spam filters. The answer, by the way, was I had to set up SPF, DKIM and DMARC correctly – especially DMARC, which strongly influences what happens to your emails depending on how restrictive you configure it.

And do not get me started on the paperwork you have to figure out and file. Going from "zero to one" is time- and resource-consuming. Fortunately, once you learn it the first time, you can do it over and over again. I do recommend you document everything you do because you won't remember every detail weeks, months or years later. We use Confluence, which has a free tier you can use, in the office and at home I use MediaWiki to accomplish the same. Writing things down takes 5 - 10 minutes but you will come to appreciate it tremendously if you make this a habit.

These things have helped me in my journey from "zero to one":

1. Remember that "a journey of a thousand miles begins with one step". It can feel overwhelming if you focus on the tall mountain you have to climb – enough that it discourages many people. So, do not focus on the tall mountain. Instead, focus on what is directly in front of you. Work the next 5 steps.
2. Ask for help. In my case, this included having a co-founder to share the load, and speaking with people in my personal and professional network who could provide advice, hands-on help, or access to people in their network.
3. Shift your perspective to "what will I learn today?". Through my life this has done wonders for me – realizing that every thing I do is a chance to learn something new makes climbing a mountain less of a chore and more of an adventure.
4. Accept that things will take longer than you planned. It is a normal part of the process. This does not imply complacency – it implies understanding that setbacks will happen so do not be surprised. Work each one as they appear, step by step.
5. Set goals for yourself every day to avoid randomization. With so many things to do, it is easy to randomly work on things and never complete them. When we launched symphonie, my co-founder and I focused on the basic things we needed and did not move onto anything else until they were complete. We worked these things one by one and each had a single threaded leader responsible for getting it done: 1) incorporation; 2) banking and accounting; 3) email; 4) business software (e.g., Google Workspace); and 5) physical office space.

It is a Business

Every person has an entire encyclopedia of stupid or bad decisions made by "The Man" they work for. When you co-found a start-up, you become "The Man". All the things you said about someone else, people will say about you. As time goes on, the "excitement" and "wonder" of growing a start-up will fade (or at least moderate) because you will have to make all the types of decisions that are "not fun" or "not popular". In other words, you realize that your start-up is "just a business" and to be successful you have to run it like a business – not a social club.

I tremendously enjoy the building part of my role at symphonie. I find the fundraising component less aligned with what I enjoy. But it has to be done because it is a business – not a hobby. So, I do it and I am well aware with time more and more difficult "not so fun" responsibilities or decisions will come my way. An example "not fun" decision: my co-founder and I had to make decisions about healthcare benefits that had no great options.

These things have helped me to remember this is a business:

1. Keep a healthy perspective that de-personalizes business decisions; make decisions working backwards from "what is the best path for the business?" – with emphasis on "best" not "right" or "perfect".
2. Talk to others about "not so fun" decisions to get outside perspectives especially from people who "have been there and done that".
3. Remind yourself that your role is not to "please everybody all the time" – as the saying goes "you can please some people some of the time" and accept that reality.

Personal Note

I struggled a bit with this post so I would appreciate feedback from you.

My struggle was simple: I felt this is an important topic that founders rarely talk about, and I felt the things that help me are so "obvious" that I wondered if writing this post was worthwhile. I also felt it was a bit longer than I preferred at 2,000 words. If you got some valuable nugget out of it, please hit the up thumb button or send me a DM via LinkedIn. If you didn't find it useful, hit the down thumb button. All feedback is welcome all the time.

For next time, I am working on a post about the things I did well and not so well when fundraising – what did I learn and how did I learn it. For anyone thinking of pursuing their own start-up or simply wanting to read a little about my experience, I think you will find something there for you.

Until then.