Don’t Be a “Woe is Me” Founder. That’s Always a Recipe for Failure. Especially Now, In The Age of AI
Don’t Be a “Woe is Me” Founder. That’s Always a Recipe for Failure. Especially Now, In The Age of AI
by | Blog Posts, Early
There’s always some truth in all of it. Especially how hard it is. Every founder who’s been successful knows how hard it is. Heck, Jensen Huang, the CEO of $4 Trillion+ Nvidia, said recently he wouldn’t be a founder if he had to do it all over again. Marc Benioff has said the early Salesforce days were the hardest of his life. Aaron Levie at Box has been candid about how brutal the journey was.
They all say the same thing: yes, it’s hard. Harder than anyone tells you.
It’s just — the founders who feel sorry for themselves? Those ones never make it.
Not in my experience at least. And I’ve been doing this almost 15 years on the SaaStr side, and another decade before that as a founder myself.
The pattern is consistent enough that I can almost predict who’s going to make it through a tough stretch and who isn’t, just from one conversation. The ones who get out alive aren’t always the smartest, or the best-funded, or the ones with the prettiest metrics. They’re the ones who refused to feel sorry for themselves longer than a week or two.
So if that’s you right now, here’s what I’d do.
Nvidia founder: I wouldn’t do it again. https://t.co/YIx8zfX50L
— Jane Adams (@iLoveJaneAdams) October 19, 2023
First. Keep It To Yourself. Mostly.
Being vulnerable has its place. But not if it demotivates the team.
I’ve been there myself. With both my startups, there were stretches where it felt almost hopeless. Cash low, customers leaving, the product not landing, a competitor raising a giant round. I shared those feelings, but with two people. My cofounder. And one very old friend who’d been a founder himself and understood. That was it.
I had a Year of Hell. Many of you will, too.
I didn’t share the weight with the team. I didn’t share it with the board (much). I didn’t share it on Twitter. I didn’t share it in all-hands.
When you tell your team you’re scared, they don’t process it the way you intend. You think you’re being authentic and human. They hear: we’re going to die, I should update my LinkedIn. And the best ones, the ones you most need to keep, they’re the ones who’ll start interviewing first. Top performers always have options. They leave first when things start to feel shaky.
There’s a version of vulnerability that works. “This quarter is going to be tough, here’s the plan, here’s how we win.” That’s leadership.
There’s a version that doesn’t. “I don’t know if we’re going to make it, I’m not sleeping, I think we may have built the wrong thing.” That’s a resignation letter the team is going to write for you.
Save the second version for your cofounder, your spouse, your therapist, and one trusted friend. Not the team. Not the all-hands. Not LinkedIn.
Second. Get Off The Floor. Stop Feeling Sorry For Yourself.
It’s OK for a week. Maybe two. After that, it doesn’t help. It actively hurts.
Even if you have to act a bit, and CEOs always have to act a bit, act more confident. Show everyone the way. If you do, you might just be surprised that not only do they follow. They find a way to make it happen.
This is one of the parts of being a CEO that almost no one talks about. You set the emotional tone of the entire company. Not your culture deck. Not your values poster in the break room. You. Your face in the Monday meeting. Your tone in Slack. Whether you walk into the office (or open the laptop) looking like a winner or a victim.
I’ve watched founders sink whole companies just by being visibly defeated for a quarter. The product was fine. The market was fine. The team was good. But the CEO had the look of someone who’d already lost, and the team picked up on it within weeks. Within 90 days, the A-players had rolled off, the B-players were going through the motions, and the C-players were the only ones who didn’t have anywhere else to go. The company never recovered.
I’ve also watched founders save companies that should’ve died, just by refusing to act like it was over. They didn’t have a magic strategy. They had a plan, even if it was a bad plan, and they ran at it like they believed it.
The team takes its cues from the CEO. Always. Pick the cue you want to give.
Third. Stretch Your Cash. Find A Way.
You can’t make radical changes in just a few months. You always need 14-18 months to fully execute a plan in B2B. Always.
Sales cycles are long. Hiring takes a quarter. Ramping a new rep takes two more. A pricing change takes 6 months to show up in net new ARR meaningfully. A repositioning takes a year to show up in pipeline. A new product line takes 18 months to be a real revenue line.
If you’ve got 6 months of runway, you don’t have a turnaround plan. You have a fundraising plan or a layoff plan. Figure out which one and commit.
Some things that work:
Cut your own salary first, but only if you really have to. I went a year without salary after we were venture funded. It was hard. We had a baby. It wasn’t fun. But it bought us 6 extra months and we used every day of it. The team noticed. The board noticed. And honestly, my own sense of urgency went up about 10x when I wasn’t paying myself.
Cut deep, once. If you have to do a layoff, do it once and do it hard enough that you don’t have to do it again in 6 months. Two layoffs in a year and you’ve broken the team. The survivors stop trusting you. Everyone good starts looking. Cut once, deep, and then commit to the team that’s left.
Renegotiate every fixed cost. Every. Single. One. Your rent. Your AWS bill. Your software stack. Your contractors. Most vendors will give you 20-30% off rather than lose you. Almost no founder actually does this. Most just stare at the burn report.
Pull forward annual deals at a discount. A 15% discount on an annual prepay is not a bad deal when the alternative is running out of money. Cash now beats margin later when you’re trying to survive.
Get to default-alive math. Paul Graham wrote about this years ago and it’s still right. Either you can get to profitability on current cash, or you can’t. If you can’t, you need a fundraise plan, and that plan needs to start now, not when you have 4 months left. Nobody funds desperation.
And One More. The Ones Who Make It Have A Different Relationship With “Hard.”
The founders who make it through don’t argue with reality.
The ones who don’t make it spend their energy on “this isn’t fair.” The market changed. The competitor cheated. The investor flaked. The customer was unreasonable. The hire didn’t work out. All of it might even be true. None of it matters.
The ones who make it accept the situation as it actually is, within about 48 hours, not 4 months, and then ask one question: given this, what do I do now? They don’t ask “why me.” They ask “what’s the move.”
That’s the whole thing. That’s the difference. It’s not strategy. It’s not pedigree. It’s not fundraising network. It’s the speed at which a founder moves from “this is unfair” to “here’s the plan.”
Being a founder is hard. It’s the hardest thing most people will ever do. Most companies fail. Most founders quit. Most VCs lose money on most checks.
But the ones who make it? They stop feeling sorry for themselves. They get up. They stretch the cash. They find a way.
I had to go a year without salary to make it work. It was hard.
It was worth it.
It always is.
Hustle. pic.twitter.com/s3d54K3AJx
— martin_casado (@martin_casado) December 13, 2023