Read 100, Meet Experts, Rewrite the Playbook
- Difficulty
- Expert
- Time to result
- ~months to results
- Steps
- 6
- Confidence
- —
Cliff’s learning system treats acquiring a skill as a founder’s operational responsibility rather than a passive educational exercise. He begins with a real business bottleneck, immerses himself in the available books and courses, and identifies the people or companies already producing exceptional results. He then speaks with or observes those experts, reproduces successful work himself, and uses the resulting evidence to rewrite the prevailing playbook. The process ends by teaching the capability to someone on the team so he can move to the next constraint. Its mechanism is unusually high input volume combined with direct observation, implementation, feedback, and delegation—not merely consuming information.
Origin
Extracted from Deep Dive with Ali Abdaal
How to run it
- 1
Choose the Current Bottleneck
Identify the skill presently limiting the product or company, such as coding, advertising, recruiting, design, or user acquisition.
Pro tip Tie the learning target to a live problem so every lesson can be implemented immediately.
- 2
Immerse Yourself in the Literature
Read the books and take the courses available on the topic until you understand its established models, vocabulary, and practices.
Pro tip Cliff describes reading literally 100 books when pursuing an important subject.
Watch out Consuming courses without implementing them may still leave you short of the required result.
- 3
Map the Best Practitioners
Create a ranked list of the companies and individuals already demonstrating the result you want.
Pro tip Use several sources rather than relying on one ranking.
- 4
Learn Directly From Experts
Contact practitioners, ask focused questions, and, when possible, observe exactly how they perform the work.
Pro tip Cliff sometimes sat behind experts in their offices to see how they bought ads.
Watch out Do not expect access without showing genuine preparation and respect for the expert’s time.
- 5
Reproduce and Test the Work
Rebuild successful examples, run them in the real environment, and compare which versions perform well or badly.
Pro tip Volume creates more feedback; Cliff remade a list of historically successful ads rather than studying them abstractly.
- 6
Rewrite and Transfer the Playbook
Turn the observed results into your own operating playbook, teach it to a teammate, and move to the next learning constraint.
Watch out Keeping the capability entirely with the founder prevents the organization from compounding it.
In the wild
To learn ads, Cliff studied the available books, ranked 100 high-performing consumer subscription companies, and contacted founders and marketing leaders around the world. In some cases, he visited their offices and watched them buy ads. He then recreated 100 historically successful advertisements himself, discovering that some worked and others failed.
→ He developed Speechify’s user-acquisition capability and converted the lessons into an internal operating skill.
When TikTok was not working well for Speechify, Cliff contacted leaders of companies already succeeding there. He established a weekly call with one entrepreneur in which Cliff taught Facebook advertising while the other founder taught TikTok.
→ The exchange created a recurring, practical learning loop around an unsolved acquisition channel.
Common mistakes
Stopping after taking courses
Cliff continued to seek practitioners and run experiments when courses alone did not produce the progress he wanted.
Studying without reproducing the work
His system depends on implementing examples and observing results, not merely collecting information.
Failing to transfer the skill
Once Cliff learns a function, he teaches it to someone on the team so he can address the next bottleneck.
From the transcript
“my system for learning is I read literally 100 books on the topic and then I talk to every expert there is and then I…”
“if I get to learn there's nothing that's in my way that stops me from learning”
“once I learn how to do it really well I teach someone else on the team how to do that and then I move on…”
From the episode
'Tell People Your Goals!': The Secret To Accomplishing Anything - Cliff Weitzman
Cliff Weitzman