Jeff Bezos: The Lessons For Entrepreneurs

In late 1993, Jeff Bezos left his lucrative job at D. E. Shaw to create a digital bookstore. He drove with his wife from New York City to Seattle and wrote the business plan in transit. 

At first, he wanted to name the company Cadabra. But fortunately he dropped this idea and instead decided on Amazon. 

Along his journey in building the company, there were many doubters about the viability of the operation. Year after year, the losses just got bigger and bigger. Yet Bezos had a long-term vision and kept moving forward. Of course, now the company is one of the most valuable in the world and continues to grow like a startup.

So given that he has decided to step down as CEO, this seems like a good time to reflect on his insights and wisdom.

Jason Tan, the Founder and Executive Chairman at Sift:

Jeff Bezos has taught a generation of founders to always think like it is day one–never stop inventing. Looking at Amazon as the behemoth that it is today, it’s easy to forget that the company has become “The Everything Store” only because Bezos made crazy bets, including successful ones like AWS, and failures like the Fire Phone.

Additionally, he taught us that working backwards from a customer need is core to being a great entrepreneur. Obsessing over earning and keeping customer trust ensures your company doesn’t sacrifice long-term value for short-term results.

Sean Foy, the COO at Shift:

He redefined attention to detail. You never hear the phrase “estimated delivery date” in Amazon. Jeff talks about customer promise, and he means it.

Jason Kingdon, the CEO and Chairman of Blue Prism:

One of the biggest lessons learnt from Bezos is that continual reinvestment of any and all incremental gains makes for an extremely successful playbook in how innovation should run—a driving force behind Amazon’s dominance in the market.

Matt Calkins, the Founder and CEO of Appian:

When I see something Jeff decided or wrote I think “yes that’s very smart.” It’s his input I respect, even more than the output and the results. He’s authored the habits and practices of his company as few CEOs ever do.

Candace Nelson, The Founder of Sprinkles:

Jeff Bezos once said, “Our brand is what other people say about you when you are not in the room,” which has always stuck with me. You can pour an enormous amount of resources into your brand identity, but you can’t control how it will be received by consumers. In my experience, people loved the Sprinkles brand but it was the trust we intentionally built on a daily basis with our customers that ultimately determined long-lasting brand loyalty.

Jedidiah Yueh, the CEO of Delphix:

Bezos transformed the world using a Russian nesting doll strategy. Mom and pop bookstores used to hold around 20,000 books, but were displaced by megastores like Barnes & Noble that held 200,000 books. Bezos built an even bigger nesting doll, with the biggest selection of all—over two million books online.

He actually replicated that strategy with the cloud. Big tech vendors used to sell computer hardware and services. Then VMware made it popular to make mini virtual machines or smaller nesting dolls. Bezos, of course, took the opposite approach and shipped the biggest doll of all—Amazon Web Services.

Michael Whitmire, the Cofounder and CEO at FloQast:

The biggest lesson I’ve learned in watching Jeff Bezos grow Amazon is the relentless focus on innovating to own a category before expanding adjacently. Some might not even remember that Amazon started by selling just books in 1994. Fast forward 27 years and not only do they sell everything, they also run much of our world through their e-commerce platform and AWS. This is because they’ve never stopped innovating and have steadily expanded their reach over time.

Ambuj Kumar, the CEO and Cofounder of Fortanix:

For me, Jeff Bezos represents the best of entrepreneurs who dream about doing something big but never lose conviction in their original first-principal thinking. He had difficulty raising the first $1 million to fund Amazon in 1994 and had to get $50,000 each from 20 outside investors (those investments would each translate to $10 billion of equity today!) but had a strong set of values. Ideas like optimizing long-term profitability and incredible customer service might look common today, but that’s only because Jeff used them to build a company worth more than $1.7 trillion.

Dave Jakubowski, the cofounder of Ureeka:

I had the privilege of interviewing with Jeff Bezos and one of the most interesting questions he asked me was “how many windows are there in the city of Seattle?” I did an elaborate breakdown on the whiteboard–looking at the population of the city, average household, windows per household, the number of towers in downtown–and when I asked him what my margin of error needed to be, he responded, “I don’t know, I just wanted to see how you think.” It was a great question and a lesson that many entrepreneurs and corporations can learn in how to assess talent in a more equitable way.

Rotem Iram, the founder and CEO of At-Bay:

What made the biggest impact on my own business thinking stems from a combination of two principles Amazon put into practice under Jeff Bezos: 1) Own the entire value chain and 2) despite serving as a retail company, ultimately be a technology company. Without those two principles, Amazon would never have built AWS or Alexa–those are two ends of the stack that a typical retailer wouldn’t imagine developing, owning and would not have the capacity to execute on even if they did.

Ev Kontsevoy, the Cofounder and CEO of Teleport:

Jeff wasn’t into resting on laurels. Even when Amazon established itself as a big successful brand in the retail industry, he understood that winning the trust of computer programmers, specifically for his web services, was going to be a battle and he was ready to meet that challenge head on. I remember him getting on stage at various developer conferences and events to deliver his “computing as utility” pitch and take questions from a skeptical audience. The bet paid off, and the era of cloud computing began, creating numerous opportunities for other entrepreneurs.

Tom (@ttaulli) is an advisor/board member to startups and the author of Artificial Intelligence Basics: A Non-Technical Introduction, The Robotic Process Automation Handbook: A Guide to Implementing RPA Systems and Implementing AI Systems: Transform Your Business in 6 Steps. He also has developed various online courses, such as for the COBOL and Python programming languages.


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