By Jeff Seibert
I’ve been building products and companies my entire career — Increo, Box, Crashlytics, Twitter and now, Digits — and I’ve had the privilege of speaking with some of the sharpest minds in venture and entrepreneurship along the way.
One recent conversation with a legendary investor really crystallized for me a set of truths about startups: what success really is, why some founders thrive while others burn out, and how to navigate the inevitable chaos of building something from nothing.
Here are some of the lessons I’ve internalized from years of building, observing and learning.
Success has no finish line
In the startup world, we talk a lot about IPOs, acquisitions and valuations. But those are milestones, not destinations.
The companies that endure don’t “win” and stop — they keep creating, adapting and pushing forward. They’re playing an infinite game, where the only goal is to remain in the game.
When you’re building something truly generative — driven by a purpose greater than yourself — there’s no point at which you can say “done.” If your company has a natural stopping point, you may be building the wrong thing.
You don’t choose the work — the work chooses you
The best founders I’ve met — and the best moments I’ve had as a founder — come from an almost irrational pull toward solving a specific problem I myself experienced.
You may want to start a company, but if you have to talk yourself into your idea, it probably won’t survive contact with reality. The founders who succeed are often the ones who can’t not work on their thing.
Starting a company shouldn’t be a career move — it should be the last possible option after every other path fails to scratch the itch.
The real killer: founder fatigue
Most companies don’t die because of one bad decision or one tough competitor. They die because the founders run out of energy.
Fatigue erodes vision, motivation and creativity. Protecting your own drive — keeping it clean and focused — may be the single most important survival skill you have.
That means staying close to the product, protecting time for customer work, and avoiding the slow drift into managing around problems instead of solving them.
Customer > competitor
It’s easy to get caught up in competitor moves, investor chatter or market gossip. But the most important question is always: Are we delivering joy to the customer?
If you’re losing focus, sign up for your own product as a brand-new user. Feel the friction. Fix it. Repeat.
At Digits, we run our own signup and core flows every week. It’s uncomfortable — it surfaces flaws we’d rather not see — but it keeps us anchored to the only metric that matters: customer delight.
Boards should ask questions, not give answers
Over the years, I’ve learned the most effective boards aren’t presentation theaters — they’re discussion rooms.
The best structure I’ve seen:
- No slides;
- A narrative pre-read sent in advance; and
- A deep dive into one essential question.
Good directors help you widen your perspective. They don’t hand you a to-do list. Rather, they help you see the problem in a way that makes the answer obvious.
Twitter: lessons from a phenomenon
When I think back to my time at Twitter, the most enduring lesson is that not all companies are built top-down. Some — like Twitter — are shaped more by their users than their executives.
Features like @mentions, hashtags and retweets didn’t come from a product roadmap — they came from the community.
That’s messy, but it’s also powerful. Sometimes your job isn’t to control the phenomenon, rather it’s to keep it healthy without smothering what made it magical in the first place.
Why now is a great time to start
If you’re building today, you have an advantage over the so-called “unicorn zombies” that raised massive rounds pre-AI and are now locked into defending old business models.
Fresh founders can design from scratch for the new reality; there’s no legacy to protect, no sacred cows to defend.
The macro environment? Irrelevant. The only timing that matters is when the problem calls you so strongly that not working on it feels impossible.
If there’s one takeaway from all of this, it’s that success is continuing. The real prize is the ability to keep playing, keep serving and keep creating.
If you’re standing at the edge, wondering if you should start — start. Take one step. See if it grows. And if it does, welcome to the infinite game.
Jeff Seibert is the founder and CEO of Digits, the world’s first AI-native accounting platform. He previously served as Twitter‘s head of consumer product and starred in the Emmy Award-winning Netflix documentary “The Social Dilemma.”
Illustration: Dom Guzman
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