10 Lessons I Learned From 10 Books About Iconic Visionaries

I have a 2 hour commute everyday on the bus. It's not exactly a Gronk Party Bus, but the great part is that I get to spend this time reading a lot of both fiction and non-fiction books. Interestingly, I noticed that over the last 5 years I'd read a collection of biographies of business visionaries. I didn't set out to read each of these biographies; many of these books were gifts, and some were randomly recommended by a friend or blog. But I read them all, and here's the list in no particular order:

#1: The Everything Store: Jeff Bezos and the Age of Amazon

#2: Onward: How Starbucks Fought for Its Life without Losing Its Soul

#3: Shoe Dog: A Memoir by the Creator of Nike

#4: Creativity Inc: Overcoming the Unseen Forces That Stand in the Way of True Inspiration

#5: Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future

#6: Walt Disney: The Triumph of the American Imagination

#7: Steve Jobs

#8: Alibaba: The House that Jack Ma Built

#9: The Wright Brothers

#10: The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley are Changing the World

Holy cow! That's a murderers' row of some of the biggest, baddest entrepreneurs from the last 100 years (one noticeable thing about this list is that it's limited primarily to white American men, and I'd love to hear any other suggestions people have). I started to think about how I could share this list and my insights from these books with my students, and I decided that this article would be the best avenue. And even if you're not one of the students I serve, you still might get something out of my takeaways from these books. So having said that, here's one nugget from each:

#1: The Everything Store: Jeff Bezos and the Age of Amazon by Brad Stone

Key Takeaway: Even geniuses fail, so you can fail, too.

When I worked at Amazon, it was easy to think of Jeff Bezos as an omniscient deity. Here's an example: Leading up to the one Bezos meeting I attended eight years ago, senior leaders and I had discussed internally for weeks on a crucial question on a project he'd assigned. Not having a clear answer, we decided to give a recommendation but ask for his thoughts in the meeting. He read the question in the document, and he immediately said, "I've been thinking about this and it should be [this number]." I nearly fell out of my chair because we were meeting with him for the first time since he'd assigned the project out a couple of months ago. I couldn't believe that he'd contemplated this question when he'd probably had hundreds of other projects to review in the interim. In hindsight, I think he could have just pulled any number and I would have been impressed. But, my main point is that from the encounter I thought Bezos was a genius who could pull answers out of his ass.

Reading this book made me understand that maybe he is a genius, but even geniuses fail and learn from their mistakes. As an example, the book shows that Amazon tried to copy eBay in an auction model at one point and failed. It also brings up how in the go-go years of the dotcom boom Amazon went on a buying spree and bought companies that haven't done much since. During my time there I also witnessed several projects such as the Fire Phone and Amazon Local come and go, and it's recently been announced that the Dash buttons and the Pop-up stores are being discontinued. In fact, Bezos himself says that he's made billions of dollars worth of failure, but it's helpful to actually read about the accounts of the failures rather than just hearing him say that. My hope is that when students encounter their failures in job searches or interviews, they'll recount that even Bezos takes his lumps now and then, and the trick is to learn from those experiences and keep moving.

#2: Onward: How Starbucks Fought for Its Life without Losing Its Soul by Howard Schultz and Joanne Gordon

Key takeaway: No one has buyer's remorse from paying the price for quality.

In this memoir, Howard Schultz describes the years of 2008-2010 when the company began to falter, and he returned as CEO to turn it back around. But the story that stood out for me was the making of Starbucks VIA, its instant coffee product. Schultz was first introduced to a potential version of it in 1989, and he began working with the cell biologist who'd proposed it to achieve a high-quality taste that was worthy of the Starbucks brand. After years of setting up an R&D lab and testing countless variations, VIA finally launched in 2009--20 years after Schultz's introduction to the initial proposal and 2 years after the cell biologist Don Valencia passed away. Yet, Schultz doesn't regret the amount of time and effort it took, and I get the feeling that Valencia didn't either.

As a product manager in the tech industry, I adhered to the industry practice of shipping early and often. Since reading this anecdote, I've been trying to reconcile the two seemingly contradictory concepts of "ship early and often" vs "let germinate awhile". I guess the lesson isn't so much about spending decades on every project but rather upholding a high degree of quality within the appropriate schedule for each task; some projects should take a shorter amount of time, but it doesn't mean that the preparation and effort should be haphazard or minimal. As an example, many of my projects could take just weeks to develop, but my proposal docs for them often went through many pain-staking iterations. Having said that, I also acknowledge that for some of my projects that there could have been more "germination" of testing and feedback than the time that I and my colleagues allotted them. Looking back, I never regretted going through one more iteration for a document, but I do regret the projects in which I didn't get enough testing and feedback in.

In relating this to the students that I work with, I think some students might get lucky and be able to apply for a job and get an offer right away. But usually this is pretty rare, especially for the good jobs you want, and there's a process and dedicated effort involved to crafting a good resume, networking, applying for jobs, and practicing for mock interviews. Becoming good at each of these tasks might vary in terms of actual time allotment for each student, but the effort and preparation required to do a good job will be high for all students. However, the good news is that I don't think a single student will regret spending the time to develop these skills.

#3: Shoe Dog: A Memoir by the Creator of Nike by Phil Knight

Key takeaway: Sell shoes instead of encyclopedias--unless you love encyclopedias.

As someone who grew up obsessed with the latest Nike shoes, reading Phil Knight's personal account of starting and running Nike in its pre-IPO days was fun to read (By the way, this is one of three autobiographies on the list, and my one recommendation to famous entrepreneurs would be to write your own story before someone else does: You come across as heroic and daring, and for some reason there are no stories of you being a jerk to anyone!).

What stood out in this book for me is that Knight starts off his career by trying to sell encyclopedias and absolutely hates it and sucks at it. He then does a little better selling financial securities, but his heart's not in it. Finally, when he moves on to selling shoes, he finds his calling. As a former collegiate runner, he knows that his shoes are awesome because they were constructed by his former track coach and co-founder Bill Bowerman, who obsessed over creating the perfect shoe for his runners. Since Knight believes in the quality of these shoes so much, trying to sell them isn't the painful task that selling encyclopedias were.

I often try to encourage students to find companies and roles that they believe in when possible rather than automatically seeking just the brand name companies right off the bat. One of my favorite exercises I like to do with students is to discuss the hobbies they have, the types of apps they have on their phones, and the articles they read on the internet to discover the types of companies and industries that might excite them. I don't believe that every student has to find a job or company that they're absolutely passionate about, and there are renowned thinkers such as Cal Newport who believe that honing valuable skills is more important--especially in the beginning of a career. But by having a general gauge of their own interests, students can sometimes come up with a role or company they hadn't thought of before. If you don't have a good sense yet of what interests you, read on to #4.

#4 Creativity Inc: Overcoming the Unseen Forces That Stand in the Way of True Inspiration by Ed Catmull and Amy Wallace

Key Takeaway: Not all those who wander are lost.

Steve Jobs and John Lasseter often get the credit for Pixar's success, but this book is told from the perspective of Ed Catmull, the co-founder and president of Pixar who was there from beginning in 1979 when it started as The Graphics Group. Between then and 1995 when Pixar's first movie Toy Story comes out, Catmull's company ping pongs through all kinds of obstacles and adventures to survive. I kept wondering when the Pixarish "fun" stuff would start to happen; for awhile they're doing graphics effects for Lucasfilms, and then they later create a super expensive image computer that they try to sell in the healthcare and government sectors in order to survive. But then Steve Jobs provides financial backing, they finally make Toy Story, and the rest is history.

As I read Catmull and Pixar's journey, a J.R.R. Tolkien line came to mind: "Not all those who wander are lost." Pixar always stayed true in being a cutting-edge computer graphics company, but it went through many multiple iterations before becoming the animation studio today. Their story encourages the experimentation and openness that might help people in their lives and careers. 13 years ago when I graduated from college, it would have never occurred to me to become a career coach, and along the way of finding this out for myself, my roles in customer service, product/program management, instock/vendor management, and other roles helped me in my journey to understand more about myself. And while I don't have plans to change careers again anytime soon, I recognize that my life and career are constantly fluid while my north star guides of making a difference, providing for my family, and enjoying my work are firmly in place. Likewise, while keeping long-term goals and dreams in mind, I'd encourage students to not be afraid of trying different roles and ideas to find out what works for them for the long haul.

#5 Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future by Ashlee Vance

Key Takeaway: To be human is to be vulnerable.

I'll be honest: Before I read this book, I always thought of Elon Musk as an arrogant and eccentric technophile whose obsession with going to Mars seemed a little weird and out of touch. And while the book doesn't completely refute that image, it does create a fuller picture of Musk that humanizes him and makes his ambitions more relatable. He comes across as sincere in his belief that a mission to Mars or a reduction in our carbon footprint through electric cars will save humanity before it's too late. His own humanity is revealed throughout the book, as he's shown to be someone who falls in love on a whim, or frets that his kids play stupid video games rather than games that develop their brains. No doubt that some of these human elements appear because the author conducted meticulous research with others around him, but I also think that they wouldn't have been revealed without Musk's own willingness to open up. Since reading the book, I've paid more attention to his interviews and witnessed his vulnerability shared at other times. In this Rolling Stone article, Musk shares that he's broken up with his girlfriend and speaks about how that's been on his mind despite his company's success, and in this Recode interview with Kara Swisher he opens up on how 2018 was an excruciating year for him.

Vulnerability, especially in the workplace, is a tricky balancing act, but I think increasingly companies and leaders are understanding the value of opening up (Brené Brown is a professor who's a leader in this field, and I've read Daring Greatly, which I recommend). For students, I don't think vulnerability means at a job interview you talk about how your girlfriend broke up with you and you had to go to therapy for months, but it does mean that you can share your passions and ultimate goals that you're striving for, and interviewers will appreciate them, because they're people like you. It also means that if you have a career coaching appointment with me, it's okay and even encouraged to share the stress and doubts that you might feel in your job search.

#6: Walt Disney: The Triumph of the American Imagination by Neal Gabler

Key takeaway: Bet on yourself as if you were a drunk gambler in Vegas.

Let me tell you right off the bat that this book is 912 pages long, but man is it good! The author Neal Gabler must have locked himself in a library and researched for years on end, because the amount of details that he shares about Walt's life is phenomenal. What stands out for me in this book is that Walt was so sure of himself and his company that any time Disney made any bit of money in the early days, Walt plowed the profits back to re-invest in the company, so much so that Gabler writes that Walt lived a fairly modest lifestyle even as a movie studio mogul. At times, his continual re-investments into Disney the company seemed reckless to me, but I guess that's why I never created an animation studio AND Disneyland in a single lifetime.

It takes real guts to bet on yourself, and in this department, I'm inspired by some of the students that I've worked with this year. As an example, a couple of students have backgrounds that would make them good fits for a data or business analyst role, but they're interested in product management, and despite some early feedback from employers that they don't have enough experience to become a PM, they've remained undaunted and have continued the PM search because they believe they can make great PMs. I'm cheering for these students, and they serve as great reminders that we could all benefit from the kind of nerve that Walt Disney had.

#7: Steve Jobs by Walter Isaacson

Key takeaway: Avoid a legacy with an asterisk

While I don't consider myself an Apple fanboy, I admire Apple products. Even as far as back in the early 1990s, I remember when my dad first bought a Macintosh, and even as an 8-year old I could comprehend that the GUI on the Mac was a step function up from the black-and-green text typing I'd seen my dad do on MS-DOS. As a result, despite having read over the years about what a jerk Steve Jobs was, I'd hoped that the biography would dispel some of those rumors and paint him in a more human light. To my shock, he comes across even worse than I'd imagined, a man who berates and manipulates people consistently throughout the course of his career. Jobs never got to defend his side of the story, but the book was an authorized biography in which he provided generous access to the author before passing away.

Since reading the book a few years ago, I've tried to find some positive spin to his character. Ed Catmull in the Creativity Inc book talks about how Jobs had softened and matured over the years. Steve Jobs was also the commencement speaker at my school's graduation in 2005 (yes, it's that famous speech), and I remember thinking in that moment that he seemed like a wizened Yoda sharing lessons on love, life, and death rather than a brash entrepreneur telling impressionable graduates to go kick down doors. But as much as I wanted to envision a narrative arc in which he learns his lessons and becomes more human, I'd find articles like this one in which Jobs is raging even just three years before his death, or this account from his daughter in which he says she smells like a toilet on his deathbed. In the end, saying that this biography was a coming-of-age story seemed too pat for a complex man.

Instead, my takeaway is that sometimes you're going to have brilliant people who accomplish a lot in the world but lack compassion and empathy to those around them. I know that many of the students I work with will go on to do amazing things, but I hope they also remember to be kind and caring people along the way because you don't want your legacy to be, "He/she was brilliant*.

*He/she was also a giant @$$#0!&"

#8: Alibaba: The House that Jack Ma Built by Duncan Clark

Key Takeaway: We're all cave men and women who want to hear stories.

I didn't know much about Jack Ma, but I read this book because several of my students are from China. Besides connecting with the students, I wanted to learn more about the Chinese tech sector and specifically about its most famous business leader. I'm glad that I did, because it helped me to shift a bit away from my American lens and see that there's great entrepreneurs everywhere. A hundred years from now, I wouldn't be surprised if Ma is lauded as the greatest business leader that ever lived. What's funny is that he didn't do so well in academics and even failed the math portion of his entrance exams twice. He also didn't have a background in engineering or tech; he was an English teacher.

But Jack Ma's superpower skill is that he's an exceptional storyteller. As someone who grew up loving Chinese martial arts stories, he's very familiar with the Hero's Journey (otherwise known as Joseph Campbell's monomyth), and he uses that same narrative to inspire his employees to fend off deeper-pocketed competitors such as eBay. In this clip, Alibaba is just starting as a company in his dingy apartment, and Jack is rallying his co-founder friends by stating that they're going to take on Silicon Valley and win. It's audacious and must have sounded ridiculous to his friends, but I know that if I were in that apartment hearing that speech, I would have run through a brick wall for him.

The need for stories is ingrained in human beings. I imagine that thousands of years ago when the first cave men and women were finished hunting and cooking woolly mammoths for the day, they'd sit around the fire and say, "Well, our lives can't just be about killing and eating woolly mammoths. Tony, why don't you make up a story that explains what the point of all of this is?" In applying story-telling in the present day, I encourage students to provide their answers as mini-stories in job interviews to explain why they tackled a problem or task. For the tried-and-true question, "Tell me about yourself," it's easy to start off by saying that you're a UW student and rattle off your prior work experience, but it's better to craft your career journey as a story and explain why you made your choices along the way.

#9: The Wright Brothers by David McCullough

Key Takeaway: Put on blinders and ear plugs.

Some might raise their eyebrows at the Wright Brothers being on this list because they seem old-timey compared to the others and don't have an existing company. My reply is that Walt Disney was born only 30 years later after Orville Wright was born in 1871, and yes, there isn't a Wright Brothers company today, but all they did was spawn an entire industry (and their original company, the Wright Company, merged or sold over the years and still exists in some form as part of the Curtiss-Wright corporation).

It's pretty impressive for a pair of bike-making brothers in Ohio who decided that they were interested in making an airplane. What blows my mind is that they'd never went to college and never received any formal engineering training, but in 1899 they'd starting kicking around the tires on the plane concept, and by 1903 they made their first flight at Kitty Hawk. Think about that for a moment. In just a span of 4 years, they went from deciding to build a plane to flying a plane when for hundreds of years so many others had failed at this attempt. They were successful because they had a relentless focus and confidence on what they wanted to achieve. Wilbur Wright in particular comes across as a relentless Terminator in his mission to build a plane; there's never a point when the brothers say to each other, "Jeez Wilbur, we're just two dudes with a bike shop, and they've got guys at the Smithsonian Institution trying and failing at attempts at flying. Do you think we're crazy stupid?"

I commonly see students compare themselves to other students. Other students seem as if they're finding jobs, but the students who come in for appointments feel that they lack the experience and skills that others have. My advice is to put on the blinders and ear plugs and ignore what other students are up to, but rather than just saying this, what better way to relay the point than to tell the story of Wilbur and Orville Wright?

#10: The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley are Changing the World by Brad Stone

Key takeaway: Knock on customers' doors.

For me, the over-arching story of Airbnb and Uber is that these two companies were able to upend powerful, entrenched opponents in the hospitality and transportation industries because they created features and services that were so customer-pleasing that their customers fought on their behalf. So how do you create these mind-bending features and services?

A good answer might be "have customer-obsession", but I'll give a slightly different reply and say, "knock on customers' doors". A fun anecdote in the book is that when Airbnb was starting off, the founders weren't sure why it wasn't taking off, and so they went to New York and interviewed a bunch of the Airbnb hosts in-person. Listening to their stories and seeing their postings, the founders realized that the listings often didn't look pretty enough to attract visitors. So they emailed the hosts to see if they'd be okay with professional shots of their places, and once hosts agreed, they would bring a camera and tripod to photograph the homes themselves. Talk about rolling up your sleeves! When I read this story, I realized that in all my time as a PM I'd believed that I was being customer-centric, but I'd never gone to such lengths as those Airbnb guys. Sure, as a product manager I'd been involved in user studies and read countless of customer feedback and reviewed data, but how many times had I received direct, in-person or phone feedback from customers? I could recount just a handful of times. Recently, I've tried to make a more concentrated effort to ask students when there's time left over in our sessions as to what they think of the coaching and programs that's offered, and it's been a very useful exercise to improve what I offer to my students, who are essentially my customers.

For students, you might not think of yourself as having customers yet, but I'd approach informational interviews with the mindset that the industry professionals you're interviewing are your potential customers for your services. Just as the Airbnb founders went out of their way to reach out directly and listen to the hosts' complaints and needs, treating informational interviews as a chance to listen to professionals of what kind of employees they want at their company might help change the feeling of these interviews from intimidating and pointless to insightful and inspiring.

If you've made it this far into the article, you probably realize a couple of things:

1. If you're a Foster student who's come see me before, you'll realize that this article was a diabolical trick to share some of the concepts that I talk about in appointments with longer examples and stories. Mwa ha ha ha! If you have more thoughts or questions or need help in your career search, you know where to find me.
2. For everyone else, you'll see that my key takeaways aren't exactly epiphanies and are just souped-up versions of common platitudes (e.g. "Sell shoes instead of encyclopedias--unless you love encyclopedias" equates to "Follow your calling."). But hopefully the examples sparked some interest in these books, and you'll choose to pick up a few of them and check them out. If you've read some of these books and have your own insights, I'd love to hear them. Or, if there are other books you'd recommend, I have a lot of time on my bus ride.
3. Finally, some might ask which 1-2 books to read if you don't have a commute like I do. I'd recommend picking a person or company that align the most with your interests, but you also probably realize that each of the key takeaways I had from one of these visionaries applied to all or many of the others. Reading all these biographies, often times I had déjà vu moments when I wondered if the authors had simply copied and pasted from each other. For example, I attributed the story-telling takeaway to Jack Ma, but in the Disney biography Walt self-describes his best skill as story-telling, and NYU business school professor Scott Galloway describes Amazon's core competence as story-telling as well. And speaking of Disney, Airbnb co-founder Brian Chesky has spoken about how the Disney biography has inspired him in his career. No wonder that they storyboard new Airbnb concepts the way animators do, and their projects are commonly code-named after Disney characters. As you can see, there all kinds of connections and commonalities among these great visionaries, and the more of them you read, the more some of their recurring traits and patterns will sink in.

Well, that's it, and hopefully you'll check out some of these books!

Best,

Jack