Every founder eventually faces a moment of truth with their domain name. It's usually somewhere between wireframing the product and pitching the first investor. You've got the idea, the branding is starting to take shape, and then the realization hits: the exact domain you want isn't available.
Some founders shrug and move on. Others panic. A few go down the rabbit hole of alternative extensions, hand-registration sprees, or awkward compromises. After nearly two decades watching companies rise and fall on the strength of their naming decisions, I can tell you this: your domain name will either quietly help your momentum or it'll slowly drain it.
Here's the advice I give to every founder who asks, sometimes privately, sometimes on stage, sometimes at 1 a.m. after they've burned through a week trying to negotiate with a domain owner who doesn't even check his email.
Start with clarity, not cleverness
Founders often overestimate how memorable a "creative" domain will be. Your customers won't. The simplest test is this: if you said the name once over a phone call, could someone type it correctly on the first try?
If the answer is no, keep looking.
You don't need something poetic. You need something that won't confuse a sleep-deprived customer holding a credit card at 11:57 p.m. I've watched startups with domains like Flickr succeed despite the spelling, but that was 2004 and you're not Flickr. The bar for tolerance on creative spelling has dropped significantly.
Quick note: I am launching my newsletter in January. Sign up now to get access to members-only information, draft copies of every chapter of my updated books, tools, insights and more! Sign up here!
Own the name you plan to scale
You don't need the perfect domain on day one. But you do need the right domain for the stage you're in.
Idea Stage: A clean, affordable, on-brand .com or strong alt-extension is fine.
Product/Market Fit: Upgrade to something that won't break your funnel or your investors' trust.
Growth Stage: Secure the exact-match .com or a strategically dominant alternative.
Investors care more than they admit. They may not ask you about your DNS setup, but they notice when a competitor owns the better version of your name. And they definitely notice when your company is stuck explaining its domain in every pitch.
I've sat in pitch meetings where a founder had to clarify "no, we're the .io, not the .com" and you could see the tiny hesitation from investors. It doesn't kill the deal, but it adds friction you don't need.
Study the competitive namespace
Founders research markets thoroughly but rarely research naming landscapes. Before you choose a domain, map out:
- Who owns the exact-match .com
- What companies operate on variations of your brand
- Whether your future "upgrades" are attainable or owned by end users
- Which extensions are already associated with products in your space
This isn't about avoiding risk. It's about understanding what you're walking into. If you're building a fintech product and the premium .com is sitting parked with a domainer, that's solvable. You can negotiate. If it's owned by a global bank, that's a permanent ceiling.
I once talked to a founder who built an entire company on a .io only to discover the .com was owned by a direct competitor in the same city. That's the kind of thing you want to know before you print business cards.
Don't negotiate like a founder. Negotiate like a portfolio manager
Founders tend to negotiate domains emotionally. Domain investors negotiate mathematically. That mismatch is where deals die.
A founder thinks: I need this. It's personal. A domainer thinks: I have 3,000 other assets. This is data.
If you want to unlock a domain at a fair price, detach your emotions from the conversation. Make polite, concise offers. Present clean terms. Show you're serious without showing you're desperate.
And don't send a paragraph explaining your startup's mission. You're unintentionally raising the price. I've seen founders write these heartfelt emails about how the domain is perfect for their vision and the seller just sees dollar signs.
Keep it simple: "I'm interested in acquiring [domain]. My budget is [amount]. Let me know if that works." You can negotiate from there, but don't give away leverage in the opening email.
Budget for domains the same way you budget for infrastructure
A domain is not a branding "nice to have." It's core infrastructure—like your database, your payment gateway, your legal structure.
Plan for:
- Initial purchase
- Future upgrades
- Defensive registrations
- Variants that protect your naming territory
If you leave this to chance, you end up paying multiples later because you waited until it hurt. I've watched companies raise a seed round at a $5M valuation and then pay $50K for a domain they could have bought for $8K two years earlier. The domain didn't get more valuable—their desperation did.
The right domain removes friction
A strong domain doesn't create momentum by itself. But a weak one will slow you down in dozens of subtle ways: lower trust, higher churn, misdirected traffic, weaker fundraising optics, endless clarification.
Think of your domain as infrastructure that should be invisible when it's working. If it's doing its job well, you won't even notice, because everything else you're building will move a little easier.
The worst domains are the ones you have to explain. If you're constantly saying "it's spelled like this" or "no, we're the .co, not the .com" or "yeah, it's weird, we know," that's a tax on every conversation. It adds up.
What this actually looks like in practice
Here's a framework I've seen work:
Pre-funding: Get something clean enough that it doesn't embarrass you. Could be a .io, could be a longer .com, could be a two-word combo. Just make sure it's not actively confusing.
Seed stage: If you're raising money, evaluate whether your domain is creating friction with investors or customers. If it is, allocate $5K-$15K to upgrade. If it's not, wait.
Series A and beyond: This is when you should seriously consider locking down the premium .com if you don't already own it. You have the budget, you have proof the business works, and the cost becomes negligible relative to everything else you're spending on growth.
I'm not saying every startup needs a $100K domain. I'm saying think about domains as a staged investment that scales with your company. Don't overspend early, but don't ignore it until it's a crisis.
The thing nobody tells you
The domain you obsess over for months will feel completely normal six months after you buy it. The perfect name you thought would change everything becomes just your domain. The compromise you settled for becomes your brand.
So yes, get a decent domain. Think it through. Budget appropriately. But don't let domain paralysis stop you from building.
The work matters more than the name. But a good name makes the work a little bit easier.