MMarketing Against The Grain
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StrategyEverette Taylor

Entrenchment-versus-Intent Targeting Rule

Prioritize motivated newcomers when converting entrenched incumbents costs more.

Difficulty
Easy
Time to result
~weeks to results
Steps
5
Confidence
97%

This decision rule compares two superficially attractive audiences: established category users who have not adopted the product and interested newcomers who want the outcome but lack a usable route. Existing users may appear safer because they already spend money, yet ingrained habits, relationships, and workflows can make them costly to convert. Newcomers can represent a larger and more receptive market when their intent is real and the company removes uncertainty. Teams compare segment size, motivation, switching friction, acquisition effort, and strategic fit before allocating resources. The rule favors the opportunity-adjusted audience rather than automatically chasing incumbents or indiscriminately expanding awareness.

Origin

Taylor contrasted experienced art collectors who were set in their ways with a much larger group interested in buying art but unsure how or where to begin.

Core principles

  • 01Existing category participation does not guarantee convertibility.
  • 02Entrenched habits create expensive switching costs.
  • 03Unserved intent can be lower-hanging fruit than incumbent share.
  • 04Audience priority should reflect motivation and conversion effort.

How to run it

  1. 1

    Define the Two Audiences

    Separate entrenched category users from interested people who have not yet established a purchasing habit.

    Pro tip Require evidence of interest from the newcomer segment.

    Watch out Do not group completely uninterested nonusers with motivated newcomers.

  2. 2

    Measure Entrenchment

    List the habits, relationships, trust structures, and workflows an existing user must abandon to switch.

    Pro tip Interview nonadopting incumbents about their current process.

    Watch out Past category spending can hide severe resistance to change.

  3. 3

    Measure Blocked Intent

    Determine what prevents newcomers from acting, such as intimidation, missing guidance, or an unwelcoming experience.

    Pro tip Look for barriers the company can realistically remove.

    Watch out Do not mistake vague admiration for purchasing intent.

  4. 4

    Compare Opportunity-Adjusted Cost

    Evaluate audience size and lifetime value against acquisition effort, conversion time, and product changes required.

    Pro tip Use scenarios rather than a single optimistic forecast.

    Watch out A larger segment can still be unattractive if support costs are excessive.

  5. 5

    Allocate and Revisit

    Concentrate resources on the stronger segment while monitoring whether market conditions alter the comparison.

    Pro tip Preserve a limited test budget for the secondary audience.

    Watch out Do not turn a current priority into a permanent doctrine.

In the wild

Choosing Aspiring Collectors

Artsy could spend heavily persuading experienced collectors to abandon familiar buying methods or welcome people already interested in art who did not know how to collect it. Taylor identified the latter as the lower-hanging fruit.

Resources could target a larger, more receptive audience with fewer entrenched behaviors.

Cloud Accounting Entry Strategy

A new accounting platform compares migrating firms tied to legacy systems with newly formed firms seeking their first professional workflow. It prioritizes new firms when migration resistance outweighs incumbent revenue.

Acquisition focuses on customers with strong intent and low switching friction.

Common mistakes

Confusing Spend with Receptivity

Established buyers may spend more today while remaining significantly harder to convert.

Ignoring Intent Quality

Newcomers are attractive only when evidence shows they genuinely want the outcome.

Making a Permanent Choice

Switching costs and audience economics change, so the comparison should be repeated.

Is it for you?

Best for

It is best for challengers and marketplaces entering categories dominated by longstanding habits or offline relationships.

Not ideal for

It is not ideal when newcomers have weak intent or when established customers can switch through an exceptionally simple migration.

From the transcript

Or we can really target this next generation of collectors that are actually interested in art.

Everette Taylor · 13:30

That bucket is way larger.

Everette Taylor · 14:00

The low-hanging fruit is really all of these people that want to buy art are interested in collecting art and just don't know how and…

Everette Taylor · 14:00

From the episode

Rethinking your Market with Everette Taylor (CMO of Artsy)

Everette Taylor