It was easy to be a founder. The adrenalin, the romance of the journey, the lure of stardom and success – it was was too hard to resist. All that was needed was a grand vision to save the world, some technical chops and about $50 to incorporate your company. An aura of heightened credibility would soon follow if you dropped out of an Ivy League school. An accelerator / incubator could get you ready for the world post demo-day, ideally in 12 weeks.

But we live in challenging times! Raising capital, attracting talent and above all – achieving successful outcomes is becoming harder, even elusive. First round financings have fallen by almost 50% since 2014. In 2018, less than ~2000 companies are projected to raise first round of VC financings. Your VP of Engineering has a better offer from the infamous FANG (Facebook, Amazon, Netflix or Google). Or from a company that just raised a mega-funding round of $100m.

To win at the startup game, most books and accelerators will teach you the art of building minimalistic slide decks. Financial projections with arrows aiming for the top right corner. You might even be able to raise your first round and get a few POC (Proof of Concept) conversations off the ground.

Welcome to the war zone

In the recent years, startups are often compared to war. The war for global dominance, the war for talent, the war for raising bigger, larger rounds…. Sun-Tzu has become a fixture on bookshelves. And for the soldiers in this war, PTSD often takes various forms. Stress, burnout, depression and suicide are a part of the unfortunate package. One founder pointed out that Steve Jobs quote encouraging to “make a dent in the universe” was all very good. “But no one warned me that the universe might make a dent in me.”

Hello darkness, my old friend…

How should founders deal with the dark side of startups? Failure, Stress, Depression. How do founders endure the lonely journey? How do they ask for help? Can we identify and engage with respect and empathy?

A number of founders who got mauled by beasts in the startup jungle have generously agreed to share anonymized experiences. One of the founders, battling depression writes, “We are operating in a high-failure environment. We have so many existential threats. Worse, everyone thinks we are on a rocket ship and asks questions like ‘are you crushing it?’” He wrapped up the survey saying “I wanted to be the next Steve Jobs. I am out of luck and am winding this startup down.”

Many founders expressed discomfort in sharing their internal challenges. They fight this battle alone. Their team members, investors or board members remain oblivious to their pain. Founders fear they might appear diminished. Others feel that “having depression will make me look weak, flawed.” Some say “I feel ashamed” and think its a “deal killer. Investors will pass / not invest if they knew.” The social stigma is significant. One of the saddest responses was from a founder who merely said “I feel broken”.

Towards a new construct

All of us are broken in different ways. As my favorite Leonard Cohen song goes, 

“There is a crack in everything – That’s how the light gets in…” 

If we all are broken, how can we make it easier to share the pain? If we pretend like we are all crushing it at all times, are we fooling ourselves? How do we support the ones who struggle? How should investors engage with founders during the dark nights?

Jerry Colonna, a former VC and now executive coach told me that our society needs a new language – a new terminology for discussing these challenges. My research on this topic has just begun. If you know a founder or a CEO who has struggled with the dark angel (also known as depression) please ask them to share their experiences via this anonymized survey link

I hope we can gather and publish anecdotes and insights from founders and journeymen alike. There are no quick fixes to these challenges, but knowing we are not alone is a start. For now, let’s start with Rumi, and welcome darkness with open arms. 

This being human is a guest house.
Every morning a new arrival.
A joy, a depression, a meanness,
some momentary awareness comes
as an unexpected visitor.
Welcome and entertain them all!
Even if they are a crowd of sorrows,
who violently sweep your house
empty of its furniture,
still, treat each guest honorably.
He may be clearing you out
for some new delight.
The dark thought, the shame, the malice.
meet them at the door laughing and invite them in.
Be grateful for whatever comes.
because each has been sent
as a guide from beyond 

— Jellaludin Rumi (translation by Coleman Barks)


  • Mahendra Ramsinghani is the author of “The Business of Venture Capital” (Wiley Finance, 2021) and “Startup Boards” (Wiley, 2014) co-authored with noted VC Brad Feld. His articles have been published in TechCrunch, Forbes, MIT Technology Review and Huffington Post. His educational background includes B. Engg. (Electronics) and MBA (Finance & Marketing). He is based in San Francisco, California.