The draw of Times Square has become the sheer volume of advertising. Photo cred: https://www.flickr.com/photos/laurent_photography/

The Misunderstood, Underestimated, and Neglected Genius of Advertising

Evergreen is a Bi-weekly collection of links to the best learning resources in business, collected by a group of managers, founders, and investors. We contribute resources about one topic, which are synthesized and shared in this Bi-weekly Edition. The aim is to learn more efficiently through increased context and focus.

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Remember, these are designed to feel like short books, you’re meant to meander and spend ~3 hours on this topic this week. Save some of these links and read them throughout the week. Immerse yourself in this topic and leave the week smarter than you started it!


When I meet readers they like to ask “What is the topic you learned the most from?” or “What was the most surprisingly helpful topic?”

I have a new answer to both of those questions: Advertising.

For a lifetime of business education both academic and self-guided, I have overlooked and underestimated Advertising. At University, it lived in the Communications college, far from the Business curriculum.

In the startup world, Advertising is viewed as an afterthought. Most startups believe advertising is proof of weakness in the product or distribution strategy.

For years, I have been crippled by a self-inflicted ignorance of Advertising, something I now believe is one of the few crucial pillars of business knowledge. (Along with Strategy, Value Capture, and Distribution). I am eager to fill this gap in my knowledge, now devouring stacks of advertising books in every spare moment.

Here are some of the things I’ve learned already:

Note on this Edition: There are fewer excerpts in this collection. This is because advertisers as a breed write densely and concisely. It would be a disservice to excerpt or attempt to summarize something so well-crafted.

Advertising as Keystone of Business

Advertising is the closest thing to a keystone trait in business. If advertising is done incredibly well, not much else matters.

  • Shitty product and great advertising? Success.
  • Terrible distribution and great advertising? Success.
  • Poor idea, weak strategy and great advertising? Success.

In story after story in these Advertising books, mediocre products with no differentiation from companies with mushy strategies become enormous successes through successful advertising. It is inspiring, infuriating, and ingenious.

The Advertiser’s Context and Mindset

Advertising is way out at the end of the value chain — the last step before a sale. This often leaves advertisers far removed from the earlier processes in product development and delivery.

Additionally, the fact that advertising is often executed by an agency means they’re informed after many decisions have already been made.

This is true in small and large companies, for different reasons. In large companies, specializations are deeper and communication is much harder, so these groups do not intermingle. In smaller companies that employ agencies, it’s much more rare to have employees with an advertiser’s skill and mindset.

Think about this chain of events:

IdeationStrategyBrandingProduct Development → Merchandising → Distribution → Marketing → Advertising.

The last step is advertising. The success of advertising determines sales, which is the ultimate factor of the profitability of the business. Advertising skill is the bottleneck of almost all business — whether or not they realize it.

Yet how many decisions throughout the process of ideation, product development, and distribution are considered through the lens of advertising? How often do you consider the opinions of advertisers?

This idea first struck me as I was watching Art & Copy. This documentary is a great introduction to the power of advertising. It profiles a handful of the most successful living advertisers.

The example that jumped out was Braniff International Airlines. In a commoditized industry, it was the advertising agencies’ (really Mary Wells Lawrence’s) idea to turn Braniff into the ‘most beautiful airline in the world’ which redefined the strategy, product, and marketing in the process of creating great advertising.

These people are Kingmakers. You will see them take Tommy Hilfiger from obscurity into overnight success. They created the Got Milk? campaign and put Reagan in office. In 90 minutes you will be fully convinced of the power of advertising — when executed to excellence.

This documentary is fantastic. I’m going to watch it 5 more times (also available on Netflix). It is full of ideas, inspiration and historical wisdom about advertisers of all different kinds.

The Advertiser’s Skills and Perspective

David Ogilvy is a legend in the advertising world. His book is one of the most impressive I have ever read by one important metric: value-per-word.

There are whole chapters that may not be relevant (How to get a job in advertising), yet the chapters that are relevant are over flowing with lessons. You will be underlining and note-taking constantly.

Halfway through his book, Ogilvy on Advertising, it became clear why this was such a crucial aspect of business. No other role in the business world involves such a variety of disciplines.

Mastering advertising requires all of the following perspectives:

  • Consumer Psychology — Understanding culture and human needs
  • Appeal Development— Crafting appeals and products to match
  • Strategy and Positioning — Establishing a brand amongst competitors
  • Communication — Clearly reach and invoke action from customers
  • Sales — Advertising is salesmanship in print/media
  • Market Validation — Tracking effectiveness of messages and value props
  • Profitability — Advertising must pay for itself over the long term

This blend of talents makes for a unique mind — the kind of person who can influence strategic and product development in helpful ways long before an advertising strategy is typically conceived.

This is a great place to start because it is higher-level than some other resources. The advice is in a sweet spot: specific enough to feel actionable, without being too involved for the non-practitioner. And most importantly, it reveals the complex breadth of the talents that make a great advertiser.

Thanks to Brandon Redlinger for suggesting Ogilvy’s book.

Scientific Advertising

There are various schools of thought in advertising. Creatives take big bold swings at changing culture and perspective. The more calculated and quantified group believes that advertising is a science, not an art.

Every scientific advertiser is a direct descendent of Claude Hopkins, author of Scientific Advertising and My Life in Advertising. Hopkins is now long gone (1866–1932), yet his influence carries on.

His opinions on the purpose and practice of advertising is roughly summed up by this:

The only purpose of advertising is to make sales. It is profitable or unprofitable according to its actual sales. […] Treat it like a salesman. Force it to justify itself. Compare it to other salesman. Figure its cost and result. Accept no excuses which good salesmen do not make. Then will you will not go far wrong.

He is the mind who turned Bissell Vacuums and Palmolive into household names over 100 years ago. By popularizing Pepsodent, he is credited with making tooth brushing a cultural norm.

It is incredible to read his frank accounts of turning products into movements, and to absorb his uncompromising beliefs about the power of scientific advertising:

I have helped a good many men to wealth and position. In many cases — in most cases — they started practically without money. The advertising had to earn its way. It was the chief factor in the business, often the only reason for success.

Reading these books feels like hearing a story from a grandfather. A very intense, very wealthy, very accomplished grandfather. Hopkins spent his entire life in advertising, and his track record is incredible.

There is a huge amount to learn from Hopkins, not in spite of his age but because of it. His lessons are timeless and his ideas inspire fresh new lines of thought for anyone in any business. My Life in Advertising is now in my top 10 business books ever read.

Scientific Advertising is expanded on and broadened by Tested Advertising Methods, which is much more of a practitioner’s guide. The two main topics are crafting appeals and copywriting — the most important skills in advertising. This book is also now in my top 10 best business books.

When you sit down to write an ad, a sales email, or to tell your companies’ story, your work will be 10x better if you have this book on the desk next to you. It’s an incredible resource, with chapters devoted to collecting the explaining successful ads, headlines, appeals, and stories.

Thanks also to Brandon Redlinger for suggesting these books.

How Advertising Creates Perceived Value

Beyond the scientific, quantified approach to advertising as a medium for sales is the belief that Advertising can create value — perceived value.

No one explains that better than Rory Sutherland of Ogilvy & Mather in his notorious TED talk suggested by Natala Constantine, Life Lessons from an Ad Man:

As George Lois said in the documentary Art & Copy:

“Great advertising makes food taste better, makes cars run better… it changes the perception of everything”

Good advertising is a form of competitive advantage — related to brand, the ability to create value through perception is something that is impossible for competitors to duplicate (at least in an identical way.)

Famous Advertising Campaigns

Part of the reason advertising is such a fun topic to learn about is to see the brilliance that has been created. Taking a look at some of the most famous campaigns in history is a great way to find inspiration and see the importance of good advertising.

Volkswagen Ads — Treasure trove of counterintuitive genius. (Suggested by Shahzad Ahsan)

Almost All Apple Ads — So interesting to see new ideas but continuity of the core brand feel.

Coca-Cola’s Long Game — No one builds a brand on slim product differentiation better than Coke.

To dig into successful campaigns in the scientific advertising world, simply find the oldest direct response ads you can in newspapers, magazines, and online. They will be the most refined, most perfected, and most profitable. They will almost certainly not be the most beautiful.

Further Reading

Each amazing book seems to lead me to another, so I still have a stack of books to get through on this topic that I will be reading immediately. Here is what I plan to get to next, if you are interested:

Robert Collier Letterbook (Recc’d by Ramit Sethi & Brandon Redlinger)

Copy Logic!

22 Immutable Laws of Branding (Suggested by Bob Hacker)

Age of Propaganda

Hey Whipple, Squeeze This (suggested by Shahzad Ahsan and Michael Bilderbach)

There is a lot more to read and a lot more to learn for me yet in the advertising world. It is exciting and invigorating to have this new perspective. I can’t wait to put it to work and see what happens!


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Thank you

Massive appreciation for those who suggested pieces of content (or wrote something new) for this Edition of Evergreen: Brandon Redlinger, Natala Constantine, Bob Hacker, Travis Dailey, Paul Chiou, Shahzad Ahsan, Shane Mac, Sarah Denby-Jones, Michael Bilderbach, Pui Kit Choi.

Many thanks for being a part of this project! Not every suggestion is able to make it to the final edit, but every single suggestion is read and appreciated.

Never Enough

As my Father always says: “There’s always room for the best.” There’s always a better resource out there. These collections can always get better, and I hope that they do. If you can think of anything that was missed, I welcome you to share it.

To share your thoughts, improvements or additions: Email or Twitter.

If you liked this, check out other Editions of Evergreen:
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How to Find and Recruit the Team you Need
How Not to Hire like a Clownshow
Compensation Rules Everything Around Me
Why Employee Onboarding is holding you back
How to Boost Employee Retention
How Performance Reviews are being Reinvented
Secrets to Perfecting Organizational Communication
How to Manage Scale, and Operate in Scaling Organizations
How to Fire an Employee
What you actually need to know about Company Culture
Strategy and Competitive Advantage:
How to Master the Craft of Strategy
Competitive Advantage: How to Build a Winning Business
The Power of Network Effects
How Cost Leadership Builds Powerful Businesses
Why the Best Brands Stand Out
Scale as Competitive Advantage
Building the Business:
How to get good business Ideas: Mental Alchemy of Ideation
Product/Market Fit: What it really means & How to Measure it
How to Failure-proof your business with Customer Development
How Strategy and Psychology Work Together to Perfect Pricing
The Most Important Equations in Business - CAC (Part 1)
The Simple Math Behind Every Profitable Business - CLV (Part 2)
How Psychology behind Word-of-Mouth Works
The Secret Core of Every Successful Business--Distribution
The Most Important Lessons in Sales
Why Value Creation is the Foundation of Business
Why Value Capture is the most important idea you haven't read about
How to be a Great Employee:
How to Start a New Job: Handling Career Transitions like a Boss
How to Master the Discipline of Product Management
I've also written about How & Why we started Evergreen:
How a prototype's failure created the next iteration
Mission & Method of Evergreen
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