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.

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 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

By Vykintas Maknickas

The old cliché says startups are born in garages and dorm rooms. That’s still true, but there’s a newer path: founding a startup inside a scale-up.

When you do that, you get the speed of a seed-stage team with the leverage of an established company. Executives and investors should care because this model can unlock new product lines, revenue and talent retention without recreating the wheel.

That’s how we built Saily, a travel eSIM service launched from inside Nord Security (the company behind NordVPN). In 19 weeks, a seven-person team went from a blank page to a live product. A little over a year later, we had scaled to millions of users with plans offered in more than 200 destinations. We did not invent everything from scratch. We reused what worked and validated everything else fast.

Incubation lowers two risks most founders underestimate

Every new product faces two existential risks: market and execution.

Inside Nord, I’d helped launch at least half a dozen new products before Saily. The pattern was consistent: Great ideas die when they target the wrong market or underestimate execution. With Saily, timing and infrastructure lined up: eSIM demand was accelerating, pain points were clear, and we could tap Nord’s backend, payments, app teams and distribution.

That allowed us to move at startup speed without startup fragility.

‘Product organization fit’ beats a great idea

Founders obsess over product-market fit. Inside a scale-up, you also need what I call “product organization fit” or the overlap between a new product and what your company already does well.

When that overlap is high, you ship faster, hire smarter and avoid costly relearning. For Saily, the overlap was obvious: Security tech we knew (virtual location, web protection and ad-blocking), and app development know-how we could bring to travel connectivity.

Competition helped more than it hurt. “No competition” usually means “no demand.” We treated competitors as free market research, reading hiring signals, product moves and funding announcements to understand where the market was headed.

And we made security the product, not a feature. Travelers don’t want another app — they want reliable connectivity that isn’t risky on unknown networks. Building privacy and protection at the network layer means safety works phone-wide with no tinkering.

Autonomy inside structure

The hard part is not technical, but cultural. Large companies run on process. Startups run on autonomy. We set up Saily as a company within the company: A dedicated product and marketing team with decision speed, plus shared services (legal, finance and design) when needed. Think of it as an internal accelerator, where the platform handles overheads so the team can focus on products.

We kept one rhythm: ship, learn, repeat. Those 19 weeks weren’t about perfection, but about getting a usable product into the world and compounding feedback.

Experimentation only works if you measure what matters: speed, unit economics and retention. For example, independent third-party testing confirmed Saily’s network-level ad-blocking reduces data usage by 28.6% — real money saved for travelers. That is a signal you double down on. If a feature or tool adds complexity without value, cut it quickly.

What founders (and operators) can steal

• Derisk in two tracks: Validate market pull and execution feasibility before you scale spend. If the market isn’t growing and your organization doesn’t have overlap, think twice.
• Reuse before you reinvent: Borrow talent, systems and channels where you can. Every overlap removes weeks of risk.
• Measure what matters: Do a simple before/after on ship speed, customer acquisition cost and retention. If the needle doesn’t move, remove it.
• Build momentum in full sight: Share milestones and learning. It sharpens the team and attracts partners.

Saily is still early, and the market is just getting started, but the model matters as much as the product. Many future founders already work inside growth companies. Give them startup autonomy and scale-up leverage and remarkable things can happen — in months, not years.

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 Vykintas Maknickas is CEO of Saily, a global eSIM app from Nord Security. A former head of product strategy at NordVPN, where he helped launch a series of new product lines, Maknickas has turned Saily into a globally successful brand with millions of users and serving more than 200 destinations. An entrepreneur since age 15, Maknickas brings a hands-on, execution-driven approach to building secure, scalable consumer tech.

Illustration: Dom Guzman