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Strategy

Crawl-Walk-Run Market Entry

Enter unfamiliar industries through progressively larger validated bets

Difficulty
Moderate
Time to result
~months to results
Steps
7
Confidence
90%

Crawl-Walk-Run Market Entry replaces a large speculative launch with a sequence of increasingly ambitious commitments. The entrant begins with a bounded project that can reveal industry mechanics, talent quality, workflow bottlenecks, audience response, and distribution realities. Success is judged against explicit criteria rather than enthusiasm alone. Evidence and capabilities gained during the crawl stage support a larger walk-stage portfolio; only repeated validation justifies a run-stage commitment. The approach is especially useful when an established operator becomes an underdog in a new domain. It preserves learning speed while limiting downside and creates opportunities to adopt newer technology and more flexible talent before legacy practices become embedded. Each stage must produce a usable asset or market test, not merely internal research, and the organization should retain the option to pause after any stage.

Origin

O'Shaughnessy described this as the mantra for entering film. His venture began with documentaries, achieved festival and distribution validation, and then expanded into commissioning more projects with younger talent.

Core principles

  • 01Start where failure is survivable
  • 02Use each stage to earn evidence and capability
  • 03Increase commitment only after real-world validation
  • 04Work with adaptable talent unconstrained by legacy habits
  • 05Use technology to compete through speed and efficiency

How to run it

  1. 1

    Define the crawl

    Choose a small, bounded project that exposes the real production and market process without threatening the wider organization.

    Pro tip Select a project capable of producing both learning and a distributable asset.

    Watch out A pilot that never reaches users cannot validate market assumptions.

  2. 2

    Set progression gates

    Specify the quality, audience, distribution, financial, and capability signals required before increasing commitment.

    Pro tip Agree on the gates before results create emotional pressure.

    Watch out Do not redefine success after a weak outcome.

  3. 3

    Recruit practical expertise

    Pair internal resources with people who understand the new field and can operate flexibly.

    Pro tip Look for talent willing to question established workflows.

    Watch out Avoid assuming success in one industry automatically transfers to another.

  4. 4

    Ship to the real market

    Complete and expose the initial project to customers, audiences, festivals, distributors, or another relevant external evaluator.

    Pro tip Seek several independent signals rather than one friendly opinion.

    Watch out Internal praise is not external validation.

  5. 5

    Extract capability lessons

    Document workflow bottlenecks, technology opportunities, talent gaps, and unexpected sources of value revealed by the project.

    Pro tip Convert each lesson into a change for the next project.

    Watch out Repeating the same process without adaptation wastes the crawl stage.

  6. 6

    Walk with a larger portfolio

    Commission additional or more ambitious work only after the first project meets its gates.

    Pro tip Increase one dimension of risk at a time, such as budget, format, or distribution reach.

    Watch out Scaling several unproven variables simultaneously obscures what caused failure.

  7. 7

    Run after repeated proof

    Commit substantial resources when multiple projects demonstrate repeatable production quality and market access.

    Pro tip Retain stage gates even after gaining confidence.

    Watch out Early success can create overconfidence and premature scale.

In the wild

Documentaries as the film-industry crawl

O'Shaughnessy Ventures entered film through documentaries rather than attempting a large studio slate. Flip Side premiered at the Toronto Film Festival, received strong reviews, and was acquired by a distributor. The venture then moved toward commissioning additional documentaries with younger talent.

→ A bounded first project generated credibility and external validation before the venture expanded its film ambitions.

Common mistakes

Starting at run speed

A large initial commitment multiplies unknowns before the organization has learned how the new industry operates.

Treating visibility as repeatability

One celebrated project is encouraging but does not prove that quality and commercial outcomes can be reproduced.

Importing legacy workflows unchanged

Copying incumbent methods can eliminate the speed and technology advantages available to a new entrant.

Is it for you?

Best for

It is best for experienced operators moving into a new field where small commercial projects can test assumptions.

Not ideal for

It is not ideal for opportunities that require immediate scale or irreversible capital commitments before any pilot is possible.

From the transcript

“So cinematically we started our little mantra is Crawl Walk Run,”

Jim O'Shaughnessy · 56:26

“So on the film side, we started with documentaries.”

Jim O'Shaughnessy · 56:52

“Much more nimble, much faster, much more responsive.”

Jim O'Shaughnessy · 57:23

From the episode

A Timeless Collection of Infinite Wisdom with Jim O'Shaughnessy

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