How to choose a great business name without the common pitfalls

Executive overview

Choosing the wrong name for a business is not fatal, but it creates unnecessary friction — harder word-of-mouth, weaker trust, and poor discoverability. Rob Walling walks through the key mistakes founders make and offers a practical elimination-based process for landing on a name that is memorable, searchable, and legally protectable. The process starts with the brand name first, then reverse-engineers a workable domain rather than the other way around. Even large successful companies (Google, eBay, Lyft) carry naming handicaps that hurt them at the margins.

A bad name won't kill your business, but it forces you to compete on hard mode from day one.

Why naming matters more than founders think

• A name is part of your brand and directly affects trust — the author distrusted eBay on first use because the name felt illegitimate.
• Word-of-mouth depends on people being able to hear, remember, and correctly spell your name.
• A bad name is a persistent headwind, not a one-time cost; every customer interaction carries a small tax.
• Even highly successful companies (Google, Microsoft, Lyft, Tumblr) have names their founders would likely change in hindsight.
• Process of elimination works better than trying to find a perfect name upfront — brainstorm 20–50 candidates with ChatGPT, then narrow down and seek external feedback.

Mistake 1: names that fail the crowded bar test

• The crowded bar test: can someone hear your name in a noisy room, understand it, and remember it?
• "Startups For The Rest Of Us" (the author's own podcast) fails this test — too long, a tongue-twister, hard to type.
• Matt Paulson rebranded from "Analyst Ratings Network" to MarketBeat after microconf feedback; the clearer name helped him scale to eight-figure ARR.
• Getting too clever — puns, wordplay — usually backfires because people get confused rather than charmed.

Mistake 2: names that are too generic or too close to a competitor

• Generic names ("Website SEO dot com") describe what you do but are not brands — you cannot own the search results.
• Being unique enough to rank for your own name from day one is a meaningful competitive advantage.
• TinySeed and MicroConf both give a feel for what they are while being distinctive enough to dominate search.
• Compound or invented words (Paperbell, Castos) let founders own their search box immediately without venture-scale SEO budgets.
• Slack and Stripe are great names but required VC money to overcome the generic search noise early on.

Mistake 3: misspellings

• Every misspelling must be explained verbally every time — this is a permanent tax on word-of-mouth.
• Examples with real costs: Lyft (Y), Flickr (no E), Tumblr (no E), Fiverr (extra R).
• Google auto-correct is a practical test: if typing your name triggers a correction, every customer searching faces that same friction.
• A compound name like TinySeed never needs a spelling disclaimer; a clever misspelling like "URLy" requires constant explanation.

Mistake 4: names that are hard to pronounce

• If five to ten people pronounce the name differently, word-of-mouth breaks down — nobody wants to say a name they are unsure about.
• Moleskine is cited as a real-world example where the E creates ambiguity ("mole-skeen" vs "mole-skine").
• Non-English brands entering English markets (Huawei, Reuters) suffer the same problem even at massive scale.
• Simple rule: show the name to a small group and check whether pronunciation is consistent.

Mistake 5: pigeonholing yourself with an overly specific name

• Names like "Linemen Jobs" or "Remote Only Jobs" lock you into a niche that may not survive a pivot or expansion.
• Brandable, slightly abstract names give room to grow without requiring a costly rebrand.
• SEO benefit of exact-match names is real but often outweighed by long-term flexibility costs.

Practical domain strategy when your ideal dot-com is taken

• Start with the best brand name, then reverse-engineer the domain — not the other way around.
• A single prefix (get, hey, use, let) or a single suffix (app, CRM, fund) is acceptable when starting out.
• The author used GetDrip.com for Drip; it worked but caused confusion and the product was often called "Get Drip."
• Alternative TLDs (.co, .ai, .io) are credible; customer.io and Clothes.io built large businesses without a dot-com.
• Avoid stacking workarounds — "GetBumpCRM.co" is too many compromises at once.
• Register a cheap fallback domain (e.g., TinySeedFund.com) early to preserve negotiating leverage when pursuing the clean version.

A real-world naming process that worked

• Derek Reimer (SavvyCal) set a domain budget, brainstormed words associated with scheduling, and fed "cal" into a lean domain generator.
• He produced a shortlist, filtered it against the criteria above, then sought feedback from a trusted network including the author.
• SavvyCal emerged as the clear winner — memorable, pronounceable, searchable, and available at a reasonable price.
• Recommended resources: the book Hello, My Name Is Awesome by Alexandra Watkins, and Laura Roeder's article on securing a dot-com without spending a million dollars.