DDeep Dive with Ali Abdaal
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Self-MasteryCliff Weitzman

Master Any Field Playbook

Read 100 books, befriend the top 100 practitioners, then rewrite the playbook

Difficulty
Advanced
Time to result
~months to results
Steps
6
Confidence
85%

Weitzman treats mastering a discipline as a repeatable pipeline he has run for engineering, product, marketing and hiring. First he consumes every serious book on the topic, sometimes a hundred, until he is a genuine subject-matter expert. Because books lag behind the frontier, he then builds a spreadsheet of the hundred people who know the field best and messages every one across every channel, following up until he lands a call and, ideally, an in-person visit. He runs his own experiments, rewrites the standard playbook, then recruits someone more talented than himself to lead that function so he can move on to the next. It is how he served as his own head of engineering, product and marketing before hiring above each seat.

Origin

Extracted from Deep Dive with Ali Abdaal. Weitzman describes it as his core strategy as CEO of Speechify: a founder's first job is to learn each function deeply, then collect people who can run it better than he can.

Core principles

  • 01Books get you to the frontier of what is already known
  • 02Beyond the frontier, knowledge lives in people, not pages
  • 03A founder's number one job is to learn every function well enough to hire above it
  • 04Direct access to practitioners beats what you can Wikipedia
  • 05You earn a field by out-studying and out-experimenting everyone in it

How to run it

  1. 1

    Exhaust the books

    Read every serious book on the topic, up to a hundred, until you can hold your own as a subject-matter expert.

    Pro tip Once business books start repeating, go to primary sources for depth.

  2. 2

    List the top 100 practitioners

    Build a spreadsheet of the hundred people who understand the field most deeply, from famous founders to unknown specialists.

    Pro tip Include people at every fame level; obscure practitioners often reply fastest.

  3. 3

    Message all of them

    Reach out on email, Instagram, LinkedIn and Facebook, then follow up until you get a Zoom call.

    Pro tip Lead with genuine specific praise for their work.

    Watch out Do not treat non-responses as rejection; keep politely following up.

  4. 4

    Meet in person

    On the call, ask to come say hello in person. Sit behind them and watch how they actually operate.

    Pro tip Offer to teach them something in return so the exchange is mutual.

  5. 5

    Experiment and rewrite the playbook

    Run a large number of your own experiments, then rewrite how the thing is done rather than copying blindly.

    Pro tip Document your process so it becomes transferable to a hire.

  6. 6

    Hire above yourself and move on

    Find someone more talented at the function than you, hand it to them, and go master the next department.

    Pro tip A company is a collection of people rowing in one direction; your job is to collect them.

    Watch out Don't cling to a function you've outgrown once someone better exists.

In the wild

Becoming a performance-marketing expert

To learn performance marketing, Weitzman listed the top 100 best-performing consumer subscription companies in the world, then arranged to sit behind the founders of Grammarly, Audible, Goop, Dollar Shave Club and Robinhood to watch exactly how they bought ads. He studied content creators like the Yes Theory team and Logan to learn content, then found the CTOs of top startups to learn hiring, implementing each process he uncovered.

Weitzman became functional head of marketing, product and engineering at Speechify before hiring specialists above each seat.

Common mistakes

Stopping at books

Books only reach the published frontier. Cutting-edge knowledge requires going to the practitioners directly.

Copying playbooks blindly

Watching experts is step one; the value comes from running your own experiments and rewriting the method.

Refusing to hire above yourself

Learning a function is not the same as being the best at it forever. Failing to recruit someone better keeps the founder as a bottleneck.

Is it for you?

Best for

Founders and operators who must get world-class at an unfamiliar function fast, and self-directed learners with no formal path.

Not ideal for

Casual curiosity, or fields where hands-on apprenticeship must legally precede any self-study.

From the transcript

I'll read every single book there is about the topic, like literally 100 books, until I'm a subject matter expert. And then I'll find all…

Cliff Weitzman · (53:30)

I'd make a Google sheet of the 100 people who knew about the topic the most. And then I'd message every single one of them…

Cliff Weitzman · (50:30)

From the episode

You're Not Lazy: How To Learn Anything Faster - Cliff Weitzman Founder of Speechify

Cliff Weitzman