5 Helpful Entrepreneurial Lessons I Have Learned From Steve Jobs

Steve Jobs has passed away and it is a very sad day here in Silicon Valley and the country. There has been a tremendous outpouring of emotion and great articles since the news broke several hours ago. I’m not going to write the 10,000th article about Jobs and his legacy, but rather take a moment to point out some distinct things I’ve learned over the years from being a fan of Apple and him (not a cult member, but someone who just intensely loves and respects Jobs and Apple).

If Things Don’t Work Out, Stay True To Your Passion

I think the thing that I most respect about Jobs is that he could have washed away in some type of mid life crisis. He was fired from Apple, the company he founded. Insanely rich and with plenty of options, there were many ways the rest of his life could have unfolded. Instead he stayed true to his passion. This is my favorite Jobs quote although “Do you want to sell sugar water for the rest of your life, or do you want to come with me and change the world?” is also pretty good (in recruiting a Pepsi exec to become Apple CEO).

“But it turned out that getting fired from Apple was the best thing that could have ever happened to me. The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.”

What many people don’t realize is how great of a company Pixar ended up being. There are 12 Pixar movies. 8 of them are in the IMDB top 250. The LOWEST grossing film they’ve ever had was Toy Story with a whopping $362 million.

It’s not hard to imagine different avenues Jobs could have gone after being let go at Apple. He could have taken a paycheck somewhere else, taken some time off, been a consultant/board member type, etc.

Instead he kept with his passion by founding NeXT and turning around Pixar, a company that is truly amazing. Eventually it led him to wealth, success, and back to Apple where he ultimately had what many consider the greatest CEO tenure of all time.

I take this to heart because in 2009, my dream job was a casualty of the recession. I had a lot of options. Staying with the company I was at but in a new role and a lot of people offered me roles at a variety of different companies. I was close to taking some. Very very close.

In the end I bought myself some time doing some consulting that was more up my alley and subsequently digging into launch Bloguin. In the end, I couldn’t walk away from what I was passionate about regardless of the hand I was dealt and the ominous economy.

Good Execution Can Trump A Bad Economy  

Many cannot remember the days when Apple was on the ropes. Desperately looking at selling themselves (nobody wanted to buy) and without a hit product in quite some time, things were very bleak towards the end of the millennium.

In the weeks after 9/11 which occurred in an economy already beaten down by the dot com implosion, Apple unleashed the Ipod and a couple of years after the Itunes store. This really started Apple’s comeback and oddly it occurred in a very turbulent economic time.

If you look at this last recession or whatever the economists want to call it, again it was Apple trudging along stoic in their execution and not rattled by the chaos around them. 

I bring this up because, at the worst possible time (beginning of 2009), I started my own company, Bloguin, when the prudent thing to be would be to put it off for awhile. While I can’t say we’ve had Apple like success, we’ve shrewdly gone about growing without too much concern about the overall economy knowing that we just needed to stay true to a good strategy and execute as best we could. 

The funny thing is that it probably wouldn’t have been possible without Apple and Steve Jobs. 

In very early 2008, I went to see my financial advisor and told him I wanted to take half of whatever money I had out of the market. I felt that over the next year it would be tough to make money in the market.

My financial planner gave me the spiel about you got to keep your money in because going in and out is often what makes it where you can’t make money and that if you’re always trusting them and the market, you really can’t lose money over time.

Hogwash. I didn’t want the money I did have to leak value over the next year so I told him I was firm in the decision and my belief that it was good to be on the sidelines.

I had no idea the economy would tank the way it did.  In November of 2008 as Apple’s stock reached $90 a share, I called my financial planner somewhat to do a “I told you do”, but also to tell him I wanted to take that money off the sidelines and invest in Apple. Then I got a whole spiel about not being diversified, eggs in baskets, blah blah blah. Screen_shot_2011-10-05_at_10.16.23_PM

A year later the stock had doubled, Bloguin was off the ground but needed me full time although it wouldn’t pay my bills. I sold my Apple stock and the proceeds of which gave me a lot more time to try to build the business without being subjected to intense financial pressure.

While I’ve built a solid and growing business in a bad economy, the opportunity to do so may have never materialized if Apple did not absolutely continue to dominate their space in an economy you think would hurt their core high end consumer electronic business. 

Marketing And Presenting The Apple/Steve Jobs Way

My first two years out of college, I worked at a software company a stone’s throw from Apple HQ in Cupertino. The marketing department was dynamic and staffed with some amazing people. The CEO of the company was not the biggest fan of Apple (although he would later convert to an Apple guy) but he was steadfast in the idea that our marketing needed to mimic Apple’s style as much as possible. 

This is kind of broad but many of you know what I’m talking about. Steve Jobs is the greatest product marketer, presenter, and demo guy of all time. His presentations are carefully orchestrated. Apple’s website, Itunes, and the UI of all the products are all eloquently designed. The copy Apple has to describe their products is uncanny and the retail stores and customer service operations via the Apple Geniuses are two of the most underrated aspects of the company.

At my job, I was basically told to watch and study all things Steve Jobs and Apple. We would pick apart certain things they were doing and try to emulate as much we could. I would spend a lot of my time building out the keynote presentations with my boss for the CEO as well as all of the various sales, media, and analyst presentations.

If you’ve worked with me you know that I use a lot of presentations and PDF’s that we/me spend an awful amount of time on. You also probably know that Bloguin blogs are strongly branded almost to a fault where a lot of good above the real estate is taken up by the high impact banners.

While I don’t think I personally emulate Job and how he presents and speaks, I will say that when given an opportunity to present or speak, I generally build out my presentation with a lot of the meticulous attention to detail, cohesive flow, and diverse usage of media and props that Jobs is known for. 

That Apple type of marketing style and attention to detail, stays with you and I am extremely lucky to have worked at an organization who strongly identified and embraced Apple’s unique marketing style.

Trust Your Sense Of Taste If You Are A Consumer Facing Business

One of the more telling quotes I heard while watching coverage of Jobs death, was an Apple employee saying “The worst thing he could say to you is that you had bad taste”.

Many times over, Apple took a leap of faith in terms of guessing what consumers would want. A phone with literally no buttons? A tablet for the masses? A push for smaller devices like the Nano and Macbook Air? All were very big assumptions and couldn’t really be backed up by research or focus groups. 

Media is a consumer facing business. If there is no appetite for what you’re doing or it is not unique enough, then nobody will consume your content. It takes a lot of confidence to trust your personal sense of taste as it relates to business and I’ll give you a little story that actually involves Apple. 

My senior year at Ohio State, the business school started this monthly business magazine and I was one of the initial five editors. After a handful of issues, I resigned because all of my story ideas were being rejected. They included:

– IAC: The Massive Web Company You’ve Never Heard Of

– Will the PS3 and New Xbox Really Replace Computers?

– Video Is Becoming Mobile

The last article was inspired by the fact that literally a week after Ohio State beat Notre Dame in the Fiesta bowl, the game was available on Itunes and was able to be put on Ipods. Back in 2006, that was kind of incredible and it hooked in nicely as it was relevant to students.

The other four editors were female and the publication was doing a lot of stuff on fashion, pastries, and what to wear to interviews. 

In the end, I just lost confidence in my personal taste for content and quit. I never really spoke up and told them the magazine sucked and was mocked most of the time when read before class. 

Yes, a little a bit of sour grapes, but in media you have to feel confident that you know where the consumer appetite is and what people will enjoy.

Over the years writing at Bucknuts and to a lesser degree this site, I began to develop a better sense of the type of content niches and concepts that were being under-served. At Yardbarker I got the opportunity to help build a media company based on what voices were unique and prolific like Spencer Hall and The Basketball Jones crew. At times I had to advocate doing some risky partnerships based on the fact that the site and writer in question would emerge as star in the sports blogosphere and luckily I was right more than I was wrong.

Running Bloguin has really put my personal taste in aesthetics and content to the test. In particular the founding team and I were a bit torn on whether to acquire Awful Announcing. Unlike five years ago where I didn’t fight for my personal taste, I was persistent campaigning for the acquisition and it’s been probably the brightest success within Bloguin thus far and something we’re highlighting a lot right now.

If you have bad taste, you probably shouldn’t be in the room making decisions at a consumer facing company. If you do, trust your instincts and don’t compromise. 

Rivalries and A Chip On Your Shoulder Can Be Harnessed To Take You To New Heights

Business is one of the few arenas where having a chip on your shoulder can serve you well. I think one of the more interesting things I’ve learned about Jobs over the years is his various clashes and rivalries with other hitters in the business world. In particular three stand out:

– Steve Jobs and Disney CEO Michael Eisner did NOT get along. Disney was trying to put the screws to Pixar and negotiations broke down for a distribution extension of Pixar films and Jobs didn’t give in and in fact announced they’d look for a new distribution partner once the Disney contract expired. What ended up shaking out? Wikipedia does a good job summarizing.

“In October 2005, Bob Iger replaced Eisner at Disney, and Iger quickly worked to patch up relations with Jobs and Pixar. On January 24, 2006, Jobs and Iger announced that Disney had agreed to purchase Pixar in an all-stock transaction worth $7.4 billion. Once the deal closed, Jobs became The Walt Disney Company‘s largest single shareholder with approximately 7% of the company’s stock.[19] Jobs’s holdings in Disney far exceed those of Eisner, who holds 1.7%, and of Disney family member Roy E. Disney, who until his 2009 death held about 1% of the company’s stock and whose criticisms of Eisner – especially that he soured Disney’s relationship with Pixar – accelerated Eisner’s ousting. Jobs joined the company’s board of directors upon completion of the merger. Jobs also helped oversee Disney and Pixar’s combined animation businesses with a seat on a special six person steering committee.”

Although not a rivalry, this excerpt from the ESPN book is a great example of a chip on the shoulder. While not diplomatic, it’s a great story. 

“The story goes that ESPN president George Bodenheimer attended the first Disney board meeting in Orlando, Florida, just after the company had bought Pixar, the innovative animation factory, and spotted Apple CEO Steve Jobs in a hallway. It seemed like a good time to introduce himself. “I am George Bodenheimer,” he said to Jobs. “I run ESPN.” Jobs just looked at him and said nothing other than “Your phone is the dumbest fucking idea I have ever heard,” then turned and walked away.”

The ESPN phone flopped and lost tens of millions. The Iphone came out shortly after.

– Jobs also butted heads over the year with Michael Dell. It was something that obviously weighed on his mind as you can see below also from Wikipedia.

“Jobs had a public war of words with Dell Computer CEO Michael Dell, starting when Jobs first criticized Dell for making “un-innovative beige boxes”.[108] On October 6, 1997, in a Gartner Symposium, when Michael Dell was asked what he would do if he owned then-troubled Apple Computer, he said “I’d shut it down and give the money back to the shareholders.”[109] In 2006, Steve Jobs sent an email to all employees when Apple’s market capitalization rose above Dell’s. The email read:[110]

Team, it turned out that Michael Dell wasn’t perfect at predicting the future. Based on today’s stock market close, Apple is worth more than Dell. Stocks go up and down, and things may be different tomorrow, but I thought it was worth a moment of reflection today. Steve.

Given Dell’s comments were from 1997 and Jobs sent that email in 2006, it’s pretty clear that the comments drove Jobs for years and was part of his motivation to redefine Apple. 

– Finally there is Jobs vs. Steve Ballmer, a rivalry that was very one sided. Ballmer over the years would often speak negatively about Apple products and ideas. He was almost never right and Jobs does a good job below attributing that to Microsoft’s poor taste. Ballmer infamously decried apps and in particular the Iphone as well. 


Just like Dell, Apple has surpassed Microsoft as well.

Similar to college sports, rivalries often inspire your best performance. Being disrespected or told you’re wrong can often be the extra motivation you need to succeed. Looking back, Jobs didn’t take too kindly to these huge titans of the business world talking down to him. In the end he had the last laugh.

There is still some people skeptical about myself and Bloguin and rightfully so. Time will tell what the end result is but it’s definitely something I am very cognizant of on a daily basis and keeps me motivated in our mission.

I’ll Miss You Steve

I have maybe a handful of personal heroes. Only Jobs makes the list from the business world.

The list of accolades is insane. In addition to the products and advancing so many areas of technology, there is also the jobs and wealth he created not only at Apple and Pixar, but companies that worked with them (suppliers, Disney, app makers, etc)

It’s only been a handful of years since I got my first Apple computer since elementary school and while my computers and other Apple devices are all really nifty, I think the personal wisdom’s Jobs lived by are more valuable than the great products I have purchased. 

Below is one of my favorite clips of Jobs who was always great when unveiling a new product. Jobs shows the Ipad’s video playback, showing a great scene from UP, a Pixar movie. He cracks a smile and goes “Isn’t that wonderful?”. Yes it is, and everything you did was too. 


About Ben Koo

Owner and editor of @AwfulAnnouncing. Recovering Silicon Valley startup guy. Fan of Buckeyes, A's, dogs, naps, tacos. and the old AOL dialup sounds