The secret to Apple's sales success | A "Live from Cupertino" book excerpt

The secret to Apple’s sales success [Live from Cupertino book excerpt]


All great presentations begin with a Sharpie and then a Mac. A
All great presentations begin with a Sharpie (and then a Mac).
Photo: Michael Hageloh

Excerpted from Live from Cupertino: How Apple Used Words, Music, and Performance to Build the World’s Best Sales Machine by Michael Hageloh and Tim Vandehey.

Prologue: What were once devices are now habits

When I set out to write this book, one of my goals was to see if I could insult fifty million people in one sentence. Here goes. Years ago, before I was excommunicated from New York City and became a resident of Texas (a state so backward that someone in our town once asked my wife and me if being Jewish was like being Catholic), I lived in Florida, which is so appealing to the unbalanced that when I took the “Florida Challenge” (where you google “Florida man” and your birthday to see what kind of headlines pop up) for April 24, the first result read, “Florida man kisses venomous snake and is immediately bitten on the lips.”

Mission accomplished. Now, let’s move on.

This post contains affiliate links. Cult of Mac may earn a commission when you use our links to buy items.

While living in the Meme State, I went to Orlando to attend a conference, and while there I tried to crash a speech by a guy named Daniel Smith, who had written a book called How to Think Like Steve Jobs. Security was tight, and I couldn’t charm my way in with my stories about a monkey and some mayonnaise. But the room was packed. Who was this guy, and what insights about Jobs might he bring to the table?

Well, I shouldn’t have bothered. I did a little research, and it turned out Mr. Smith had written more than ten books on the “How to think” theme, about icons ranging from Bill Gates to Leonardo da Vinci — people he obviously hadn’t met any more than he’d met Steve. His main qualification seemed to be that he’d been an Apple customer for eight years. Based on that logic, I’m qualified both to practice internal medicine and run a Jewish deli. So come on down to Michael Hageloh’s Primary Care and Pastrami, where you can get medication to lower your cholesterol followed by a meal to raise it!

The Steve Jobs myth and the Apple brand

A backstage picture from a 2008 Apple event, taken with an original iPhone, demonstrates the amount of "performance" these presentations require.
A backstage picture from a 2008 Apple event, taken with an original iPhone, demonstrates the amount of “performance” these presentations require.
Photo: Michael Hageloh

Still, there was that auditorium and its wall-to-wall attendees. That’s the power of the Steve Jobs myth and the Apple brand. Ever since “Think Different,” the world has ached to know how Apple did it. What was the secret sauce? How did Apple create the Cult of Mac and become the world’s first trillion-dollar corporation? Then there’s the question every entrepreneur, designer, and would-be startup CEO wants the answer to:

How can I be more like Steve Jobs?

You can’t. Sorry. There was only one Steve. How do I know? Because I worked for Apple from 1988 to 2010, making my exit not long before Steve made his own exit due to pancreatic cancer. I worked with Steve’s most lauded customer: educators. I wasn’t in the garage when he and Woz cobbled together the Apple I in 1976, so I didn’t see everything, but I saw almost everything:

  • The sad “beige box” days when we forgot who we were and tried to be who everybody else thought we should be;
  • The March of the Generic CEOs;
  • The near-death of the company, when we were nearly sold to archrival Microsoft;
  • Our thrilling turnaround in 1997 after Steve resumed his role as leader;
  • The spectacular rebirth — led by the iPod and iTunes — that would one day make Apple the world’s most valuable corporation.

Am I a designer? An engineer? One of Steve’s right hand men? No. Again, sorry to disappoint you. I’m nowhere near that interesting. For most of my time at Apple, I was part of the company’s Higher Education sales, the line of business that kept the company alive during the dark years. I spent my days calling on colleges and universities all over the country, trying to persuade their departments — from music to physics to athletics to colleges of business — that Apple products would take their students into the twenty-first century. And I guess I did something right, because I closed more than $1 billion in deals before I packed up my dollies to try my luck with Adobe and a handful of startups.

Wait a sec, go back. Apple has enterprise-level salespeople (aka account executives)? Don’t its products, well, sort of … sell themselves?

Yes, it does. But I don’t blame you for thinking that. After all, that’s what CEO Gil Amelio told us at our annual sales meeting in 1997, when the company was weeks from acquisition or bankruptcy. He said, “Get out of the way. These things sell themselves.” You can imagine how dandy that was for our morale. It’s also dead wrong.

No, Apple products don’t sell themselves

Michael Hageloh wrote <em>Live from Cupertino</em> based on his years working as an Apple salesman.
Michael Hageloh wrote Live from Cupertino based on his years working as an Apple salesman.
Photo courtesy Michael Hageloh

If you’re in sales or know anything about sales, you know that no product, no matter how wonderful, sells itself. Second, even products as brilliant and world-changing as the iPhone face headwinds. There are entrenched systems, concerns about things like price points and sales channels, and the fact that truly new and different products scare the bejesus out of some people. Products don’t sell themselves. Salespeople do that.

Still, the first part of my tenure at Apple was tough. Our creative mojo left with Steve, and Macs were a tough sell. “No one ever gets fired for buying IBM,” went the conventional wisdom. We were on life support through most of the ’90s. I went home many Fridays wondering if I would have a job on Monday. But I was the only one in my territory who was never laid off, and it was because I didn’t push boxes. I sold myself first, Apple second, and the product third. I practiced the truest version of selling: building relationships based on trust and finding the creative moments that led to one record-breaking deal after another.

But you’ve heard all that before. You’ve read sales books about relationship-building and customer relationship management (CRM). You’ve trained on all the systems at seminars that bored you into a coma. Good thing I’m not here to talk about that stuff. I’m here to share the sales story that no one’s ever shared publicly — to walk you behind the scenes of the most iconic, obsessed-over brand in the history of consumer products and answer the question every sales professional wants to know: “How did Apple do it?”

The secret to Apple’s sales success

In a word, it was music. Musicality was in the DNA of nearly everyone who worked at One Infinite Loop in Cupertino, California, in those days. In the ’80s and again in the late ’90s and 2000s, music suffused Apple’s culture. You thought it was a coincidence that it was the iPod and iTunes that brought the company back from the brink? Our employees were musicians, performers, composers, producers, creative rebels, and entertainers. That’s one reason journalist Umair Haque, blogging for the Harvard Business Review, wrote, “Apple is less like a company. It’s more like a band. It makes stuff it loves. It doesn’t care what you think. Not you, critic, nor you, competitor, nor me, analyst, nor you, loyal Apple fan. Not a single one of us. It cares whether what it makes is good by its own standards — good enough to love.”

That’s right, and that same love and passion for music didn’t stop at design and engineering. It carried over to us in sales. Because selling is more like performing live than any other part of business. It’s just you and the audience in real time, with you trying to make a connection and inspire them to join you on a journey. You’re reading the room, improvising and working without a net, and when you can bring real fire and joy to the performance, you’re at your best. That’s when you love selling, and the customer loves you right back.

Steve Jobs was part poet, part lead singer; part dictatorial producer screaming orders from the booth. We were at our best when he was at the front of the room like an orchestral conductor, and when he left the company, he took the music with him. From 1985-1997, Apple was elevator music, Auto-Tune, easy listening — bland and inoffensive. That nearly killed the company.

When Steve came back, he instantly revived our dormant musicality and the company with it. That made “Think Different,” the iMac, iPod, iPhone, and iPad not only possible, but made them products that changed the world — products everyone had to have. To put it another way (and to borrow from the title of a great Doobie Brothers record), what were once devices were now habits.

But in some ways, those amazing products were a harder sell than the old desktop computers because the unfamiliar requires persuasion. Our job was to make Steve’s vision tangible for people who’d never met him or heard him make his presentations. Turnkey sales techniques — the IBM method, the Xerox method, the Herman Miller method — weren’t going to get it done.

Technology wasn’t much help, either. can give you the facts and figures, but it can’t sense hidden opportunities. It can’t demonstrate emotional intelligence. It can’t dazzle. Apple didn’t even have a corporate Customer Relationship Management (CRM) system until 2006, and when we finally got one, we wrote it in-house. I know, because I was one of many test humans. Today, Apple Retail has turned that CRM into a competitive advantage.

So how the hell did we do it?

The methodology was that there was no methodology. I suppose it would be more accurate to say that our methodology was about who we were, not what we did. If you’re looking for a successful sales methodology, start by asking your top people. They already know what it is because they’re using it. Importing a methodology from outside will just waste time and money and alienate those same stars.

That doesn’t mean Apple didn’t try to buy sales success. We did. We bought a number of external methodologies from vendors. One was called “Hope is Not a Strategy,” and it lasted a few months. Others fizzled even faster. The engine that not only made Apple sales rattle and hum (apologies to U2) but shaped our legendary culture was our passion for music and our penchant for weaving its elements — rhythm, harmony, storytelling, and so on — into every department and everything we did. That’s why Apple was such a great fit for me.

Copyright © 2019 by Michael Hageloh with Tim Vandehey. All rights reserved. Published by Post Hill Press. Used with permission.

Get Live from Cupertino

Live from Cupertino: How Apple Used Words, Music, and Performance to Build the World’s Best Sales Machine is available today from Amazon and other top booksellers.

Buy from: Amazon