By Yakov Filippenko

No founder plans for the day they get fired from their own company.

You plan for funding rounds, product launches and exits, but not for the boardroom moment when everyone raises their hand, and you realize your journey inside the company is over.

It happened to me. I called that board meeting. I set the vote. We had to choose who would stay, me or my co-founder. The vote didn’t go my way.

In movies, this is where the music swells and the credits roll. Steve Jobs after John Sculley. Travis Kalanick after Bill Gurley. In real life, there’s no cinematic pause. No final scene. Just the quiet realization that everything you built now belongs to someone else.

What follows isn’t drama, either. It’s disorientation. And like most founders, I had no idea how to handle it.

Don’t fill the silence too fast

When it ended, I filled my calendar with aimless meetings. Five or six a day. Not because they had any real purpose, but because it felt strange not to be doing business. For more than 10 years, I’d never had a day when I didn’t have to think about work. A startup teaches you to fix things fast.

When you’re out, though, there’s nothing left to fix. Only yourself. Getting pushed out isn’t like missing a quarterly target. It’s like losing the story you’ve been telling yourself for years.

The hardest part is that you don’t know who to blame.

Investors? They were doing their job. Yourself? Every decision made sense in context. So the frustration lands on the person closest to you. Your co-founder. It’s not about logic. I would say it is more of a defense mechanism. It’s how the mind tries to make sense of loss.

Learn to see the pattern

For months, I kept asking: What did we do wrong? It took me a couple of years to see the pattern.

Later, working inside a venture fund helped me see the truth. I saw the same story play out again and again. Founders repeating the same emotional arc, as follows:

• Expectation of an M&A deal;
• Long wait for the deal;
• The deal collapses;
• The startup stalls;
• Expectations diverge; and then
• Resentment between co-founders

Every time, the same sequence. And when the dream fades, blame fills the gap.

The pattern itself is that the anger toward a co-founder is often a projection of disappointment from a failed deal. If that energy isn’t processed consciously, it finds its own way out, usually as anger. You can’t really be mad at yourself; you did everything right. The other side acted in their own interest. So it lands on the person next to you, your co-founder and your team, and for them, it’s you.

And that’s where I have a bit of a claim toward investors because they often see this dynamic coming and could at least warn founders about it.

Once I recognized the pattern, I stopped seeing my story as a failure. It was part of a cycle almost every founder goes through, only most don’t talk about it.

Trade strategy for emotional tools

Traditional business tools didn’t help. OKRs, planning sessions, strategy off-sites, none of it worked on the inner collapse that comes when your identity and your company split apart.

This led me to begin studying Gestalt therapy. It gave me the language to understand how situations like this actually work, their cycles, causes and effects, and how to think about them with the right awareness and perspective. One part of building startups isn’t about pivots or fundraising. It’s realizing how much of yourself you’ve tied to the story you’re telling the world.

The point is to first get conscious of your anger, and then let it out.

Acceptance comes in stages

Acceptance doesn’t show up all at once. It arrives in pieces.

For me, the first piece came when I watched another founder go through the same breakdown and recognized every stage.

The second came when my first startup was acquired. Not at the valuation I’d dreamed of, but enough to accept that it continued without me. The third came with my current company, Intch, which is built from calm, not from fear.

I no longer measure success by control, but by clarity.

What I’d tell a founder in that room

Here’s what I’d share now with another entrepreneur who finds themselves in the same situation.

• You’re losing a story, not your worth. Give yourself space to grieve it.
• Don’t let anger choose a target. Name the pattern instead.
• Find mirrors. Other founders are walking through the same steps.
• Business tools have limits. Emotional tools matter here.
• Acceptance comes in stages. You’ll recognize them when they arrive.

Founders are trained to manage everything except their own psychology. But startups are way more than capital and code. They run on the emotional architecture of the people who build them. And when that structure breaks, rebuilding it is the most important startup you’ll ever work on.

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 Yakov Filippenko is a seasoned entrepreneur with more than 10 years of experience in IT and technologies, as well as scaling businesses internationally. As a product manager at Yandex, he led a team that grew the product’s user base from 500,000 to 1.2 million and secured its entry into the international market. Subsequently, he co-founded SailPlay, which he scaled to 45 countries and eventually exited, after it was acquired by Retail Rocket in 2018. In 2021, Filippenko launched Intch, an AI-powered platform connecting part-time professionals with flexible roles.

Illustration: Dom Guzman

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

By Alexander Lis

AI startups are raising capital at record speed. According to Crunchbase data, AI-related companies have already raised $118 billion globally in 2025. And, so far, traction looks impressive. AI startups are posting stellar revenue growth, and even the $100 million ARR milestone is often achieved.

While this growth is breathtaking, some analysts are beginning to question its sustainability. They warn that AI spending may soon reach a peak and that unprofitable tech companies could be hit hardest when the cycle turns. If that happens, many investors in AI will find themselves in a difficult position.

Predicting a bubble is rarely productive, but preparing for volatility is. It would be wise for both founders and investors to ensure that portfolio companies have enough resilience to withstand a potential market shock.

The key lies in assessing the durability of ARR. In a major downturn, the “growth game” quickly becomes a survival game. History suggests that while a few companies may continue to grow more slowly, the majority will struggle or disappear.

The question, then, is how to tell the difference between sustainable and hype-driven ARR.

What distinguishes durable ARR from hype?

Several factors set true, sustainable revenue growth apart from hype.

The first is customer commitment. Sustainable revenue comes from multiyear contracts, repeat renewal cycles and budgeted spend within core IT or operating lines. When revenue depends on pilots, proofs of concept or amorphous “innovation” budgets, it can vanish when corporate priorities shift. A company that touts these short trials as ARR is really reporting momentum, not recurring income.

This is what investor Jamin Ball has called experimental recurring revenue.

Traditional software firms can thrive with monthly churn in the low single digits — think 5% to 7%. But many AI companies are seeing double that. This means they have to sprint just to stand still, constantly replacing users who move on to the next shiny tool.

Another differentiator? Integration and workflow depth. Durable ARR is embedded into the customer’s core workflows, data pipelines or multiple teams. Ripping it out would be costly and disruptive. Hype ARR, by contrast, lives on the surface — lightweight integrations, fast deployments and limited stakeholders. Without unique intellectual property or deep workflow integration, such products can be replaced with minimal friction.

And finally, real growth is defined by clear value-add. True ARR is backed by measurable ROI, well-defined outcomes and long-term customer roadmaps.

In contrast, hype ARR is driven by urgency (we need to show our shareholders our AI deployment ASAP), or undefined ROI. In those cases, customers don’t even know how to define success. They are testing, not committing.

Beyond ARR

It is important to put ARR traction in context. Investors and founders should focus on a broader set of indicators — conversion from pilots to long-term contracts, contract length and expansion, net revenue retention, and gross margin trajectory. These metrics reveal if growth is sustainable.

It would also be helpful to assess the product’s real impact: efficiency uplift (more code, content, or customer conversations per employee-hour), accuracy improvement (e.g. for detecting bad actors), and higher conversion rates, among others. These metrics should exceed client expectations and outperform alternative tools. That’s what signals genuine value creation and a higher chance for experimental revenue to turn into durable ARR.

After all, AI may be changing how fast companies can form and grow, but it hasn’t suspended the basic laws of business.

For founders, the message is simple: Celebrate ARR if you so wish, but pair it with proof of retention, profitability and defensibility. For investors, resist the urge to chase every eye-popping run rate. The real competitive edge in this next phase of AI is stability, not spectacle.

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Alexander Lis is the chief investment officer at Social Discovery Ventures. With 10-plus years of experience across public markets, VC, PE and real estate, he has managed a public markets portfolio that outperformed benchmarks, led early investments in Sumsub, Teachmint and Byrd, and achieved 20%-plus IRR by investing in distressed real estate across the U.S.

Illustration: Dom Guzman