Tactical insights for first-time founders to outsmart the burn, the churn & the breakdown.

Hey Founder,

2026 is staring you down, and there it is again, that restless fire in your chest: part fear, part adrenaline, part the weight of everything 2025 asked of you (and everything it didn’t deliver).

At the center of it all is one question you can’t ignore:

“Am I the founder I want to be?”

Not just “Did we grow?,” but “Who did I have to become to get here?”

Because that’s the real difference: building outside-in, chasing noise and numbers, or building inside-out, where purpose and honesty shape what comes next.

So before the new goals rush in, here’s your mirror — five sharp questions to help you enter 2026 clearer, calmer, and in control.

Let’s dive in.

Ben Horowitz once said the darkest founder moments aren’t when you don’t know what to do, they’re when you do know, and don’t want to face it. That gap between clarity and action? That’s where companies quietly fall apart.

“Am I the founder I want to be?” isn’t just introspection.

It’s a test of whether your decisions match your story.

A few well-known founders have stood in that tension:

Tobi Lütke (Shopify) admitted he was a terrible manager - stuck in meetings, structure, and politics, when his real value was in product. So he rewrote his role entirely: stripped middle layers, delegated operations, and focused on architecture. Shopify’s GMV jumped from $17B to $30B - their fastest growth ever.

Yvon Chouinard (Patagonia) hit a wall when the company’s success started clashing with its message. Preaching sustainability while selling more stuff? Instead of spinning the narrative, he gave up ownership and redirected all profits to climate causes. He aligned the business to his truth.

Brian Chesky (Airbnb) realized the platform had drifted - too many fees, bad listings, lost trust. After analyzing millions of complaints, he publicly acknowledged the missteps and rebuilt the core product. Cancellations fell 36%, revenue rose 17%, and trust came back.

Different stories, same pattern:
Founders who are brutally honest with themselves build companies that are far more resilient and far more real.

Your business is an expensive mirror of your inner world, and when something feels off in the company, it usually starts with something unaddressed in you.

One honest question - asked without flinching - can surface a pattern you’ve been ducking for years. The hard part isn’t seeing it. It’s saying it out loud.

So if a question makes you uncomfortable, that’s the one to stay with.

Who are you without the logo, the pitch, or the story of being a founder?

Q1: If the business ended tomorrow, what part of me would feel like it ended too?

If the answer is "almost all of me," that’s likely where your overwork, fear, and hard-to-break habits are coming from.

You can fool a pitch deck or a LinkedIn post, but not your team.

Q2: What’s the one thing I hope my team never says about me when I’m not around?

That answer reveals the gap between how you lead and how you're experienced. That’s where your growth lives.

Once you see the gap, the question becomes: are you building something that still feels true?

Q3: What does success on my terms look like, and am I building toward it?

If not, you’ve just outlined what needs to change (in you and in the business)

It’s rarely everything that’s stressing you. It’s what you’ve avoided.

Q4: What decision have I delayed for six months that would solve most of my stress if I faced it?

Whatever comes up here is not a reflection prompt. It’s your first must-make decision of 2026.

When you zoom out far enough, most urgency fades.

Q5: Looking back from 2036, what will I regret staying loyal to this year, and what choice will I be proud I made?

If those answers aren’t shaping your weeks already, it’s time they start.

Pick the one question that hits hardest. Block 45 minutes and write what 2025 looked like through that lens - what you avoided, overcompensated for, or kept quiet. Then ask: what would have to shift in 2026 for that answer to feel different, not just look different on paper?

Find the sentence that makes your stomach drop. Share just that line with someone who’s seen you under pressure and won’t sugarcoat it. Ask: “Is this true?” Don’t justify. Just listen. That’s your blind spot.

On one page, define how you make decisions, how you lead, and how you handle conflict. Keep it simple. Share it with someone you trust and revisit it monthly. This becomes your personal compass.

List the hard things you’ve been avoiding: the hire, the co-founder tension, the outdated strategy. Pick the one that would ease your mind the most. Book the conversation or set a decision date within 7 days.

Ask of every big initiative:

If it fails two, cut or pause it. Then zoom out: write one line for where you want to be in 1, 3, and 5 years across life, business, and finances. If your plan doesn’t move you toward all three, it’s time to rethink the plan.

This week's “you need to see this”:

Before you go…

Ever heard Drive by Incubus?

It’s about realising fear or habit has been steering your life, while you pretend you’re at the wheel.

Founder life just amplifies that.

These five questions? They’re a chance to take the wheel back. Not just to keep going, but to lead as someone you trust.

That version of you is the real moat.

See you next Thursday,

— Mariya

Hit reply and let me know. I read every single one (for real).

Hey, I’m Mariya, a startup CFO and founder of FounderFirst. After 10 years working alongside founders at early and growth-stage startups, I know how tough it is to make the right calls when resources are tight and the stakes are high. I started this newsletter to share the practical playbook I wish every founder had from day one, packed with lessons I’ve learned (and mistakes I’ve made) helping teams scale.

Mariya Valeva

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