Learn Entrepreneurial Lessons from Barack Obama’s A Promised Land

Obama on the Phone

When we vote for a President of the United States we are actually electing the CEO of one of the largest employers in the world. When Reading A Promised Land by Barack Obama, he reveals how he led and the lessons that he learned.

Read Time:10 Minute, 13 Second

Photo by History in HD on Unsplash

When we vote for a President of the United States, the voters are presented with a series of policy positions, i.e., lower taxes or universal healthcare, for example, that they will implement. However, there is a reason that this position is called the Executive Branch. The President doesn’t pass laws or negotiate them. He doesn’t do the fine-tuning of broad policies to make them work; instead, he hires the people to do it and then manages him. In the first volume of Barack Obama’s memoirs, A Promised Land, he talked less about his executive actions and more about the personalities and people he was responsible for leading

The author of this article may realize revenue from any affiliate links.

Looking back through my notes, I realized that his leadership philosophy was embedded in his telling stories.

I have included several quotes that show how he approached his managerial responsibilities, his leadership philosophies, and how he approached his job in a way that any entrepreneur would recognize.


Photo by Mathieu Stern on Unsplash

“We became more sensitive to the possibility that someone else was getting something we weren’t and more receptive to the notion that the government couldn’t be trusted to be fair. “

— RENEGADE Page 276

Presidential Context: President Obama was focused on passing several social programs during his first term. The media’s (and in turn, the voters’) focus was on the quantitative inequalities and the fact that different cohorts of our society were receiving different levels of support. President Obama found it hard to explain that each of these cohorts needed different levels of support for the good of the overall society.

The Entrepreneurial lesson: Success is not a finite good. Often, what is given to one will help the larger group in the long term. When evaluating resource expenditures, how does the whole organization benefit? If stakeholders might perceive how they are “missing out,” discuss short term costs vs. long term benefits.

“We were confronting similar issues at agencies charged with regulating the financial system, where overstretched and underpaid regulators could barely keep up with the sophisticated, constantly evolving operations of massive international financial institutions.”

— IN THE BARREL Page 568

Presidential Context: The MMS (Minerals Management Service), a subagency within the Interior Department, was responsible for leases, royalties, etc., concerning offshore drilling. During the Deepwater Horizon debacle, Obama was forced to explain how the regulators at the MMS, as well as other agencies, hadn’t prevented the disasters in his first term. His argument, throughout the book, is that reducing spending in regulation enforcement results in a smaller and less efficient regulatory agency, with predictable results.

The Entereupernial lesson: There are consequences for each staffing decision that you make. When you hire junior employees, you will have to pay for their mistakes and the opportunities they will miss. When you hire senior employees, you will have to pay more upfront, but you are able to leverage their experience and skill to do more for your business, ensuring that you keep your company competitive.

Regardless of their level of experience, you have to make sure that someone keeps up with the market and what is new. You want to continuously encourage your team to upskill and keep learning about their field. Without doing so, you will have your own Off-Shore Oil Spill.


Photo by Clay Banks on Unsplash

“I’d failed to tell the American people a story they could believe in; and whether, having ceded the political narrative to my critics, I was going to be able to wrest it back”

— IN THE BARELL Page 525

“Such arguments had nothing to do with facts. They were impervious to analysis. They went deeper, into the realm of myth, redefining what was fair, reassigning victimhood, conferring on people like those traders in Chicago that most precious of gifts: the conviction of innocence, as well as the righteous indignation that comes with it”

— RENEGADE Page 274

Presidential Context: These two quotes discuss the Democrats’ failure to combat the Tea Party’s message during the first half of his term. Leading up to the disastrous midterms of 2010, President Obama’s administration lost control of its message. By not being able to control the narrative, the administration faced significant opposition to their decisions, never having a chance to really explain their successes.

The Entrepreneurial lesson: You have to control the narrative about your product or service. Explaining that your product reduces your client’s costs by 25% doesn’t matter if they already feel that your product is buggy or inefficient. Remember that narratives are harder to move with facts after they have been established, you have to set the story in your customer and potential customer’s minds early and continue to support it.

Spend time monitoring your client base so that you can help shape the narrative around your product: conduct market surveys, do client outreach, and publish content regularly. Don’t let a great product be killed by bad press.

People Management

“Our history has always been the sum total of the choices made and the actions taken by each individual man and women […] It has always been up to us”


Presidential Context: This quote is from a speech that President Obama gave at Normandy Beach on the 65th anniversary of the Allied landing at Normandy. He explains that he reflected on how those young soldiers that landed on the beaches helped create the future that we are in today.

The Entrepreneurial lesson: As an entrepreneur, you are going to make decisions every day. Some are small, and some are large. Some will work out, and some will blow up in your face. Remember to hold periodic retrospectives and find lessons in the failures. Celebrate your successes, but make sure to thank those that helped you get there. Your story will be the sum of your success, failures, and all of the people you met along the way.

“A breadth of experience, familiarity with the vagaries of life, the combination of brains and heart — that, I thought, was where wisdom came from […] It was precisely the ability of a judge to understand the context of his or her decisions, to know what life was like for a pregnant teen as well as for a Catholic priest, a self-made tycoon as well as an assembly-line worker, the minority as well as the majority, that was the wellspring of objectivity.”

— THE GOOD FIGHT Pages 389–390

Presidential Context: This section is President Obama talking about the nomination and confirmation of Justice Sotomayor to the Supreme Court. President Obama is cautioned not to ask too many legal questions at the risk of appearing to have a litmus test. Instead, he got to know the nominees primarily by talking to them about their experience and temperament.

The Entrepreneurial lesson: Look outside the box for your employees. Ask yourself, what does this person need to be able to do? What life experiences might the ideal candidate have to fit within your organization?

You may even want to go further by re-evaluating your hiring process:

  • Can you make Blind Hiring work for your organization?
  • Are your teams balanced enough, or do you need to screen for more soft skills or hard skills?
  • Have you involved your junior team members to interview so you can determine what experiences can help your team grow?


“I reminded myself that it was part and parcel of the presidency for nothing to ever work exactly as planned. Even successful initiatives — well executed and with the purest of intentions usually harbored some hidden flaw or un-anticipated consequence. Getting things done meant subjecting your self to criticism, and the alternative — playing it safe, avoiding controversy, following the polls — was not only a recipe for mediocrity but a betrayal of the hopes of those citizens who’d put you in office.”


Presidential Context: This section talks about the Recovery Act and some of his administration’s risks in providing loans to alternative energy companies, namely Solyndra. Solyndra was given a sizeable loan to build solar panels. After several issues: manufacturing delays, Chinese manufacturers undercutting Solyndra’s prices, problems of supply and demand, the company had to fold. It was a popular talking point and undercut a lot of the positive impact of the bill.

The Entrepreneurial lesson: %^& happens is the short version of this lesson. The longer version is that every successful endeavor incurs some risk. Playing it safe will kill you while taking calculated risks can lead to great success (or failure). But, you will never succeed in being meek and consistently playing it safe.

“It wasn’t simply that each decision I made was essentially a high-stakes wager; it was the fact that unlike in poker, where a player expects and can afford to lose a few big hands even on the way to a winning night, a single mishap could cost a life, and overwhelm — both in the political press and in my own heart — whatever broader objective I might have achieved.”

— ON THE HIGH WIRE Pages 666–667

Presidential Context: Before his first Central and South America tour, President Obama had decided to use military options in Libya to protect civilians. While at dinner with the Chilean President, President Obama is alerted that a jet had gone down, and search and rescue was trying to find the second member of the crew.

The Entereupernial lesson: The US President’s job can be scary and has many life-altering decisions every day. While you may have to make some life-altering decisions, but you are not the President of the United States.

You are the poker player. You will lose a few hands, and so you should plan for it. Make sure you have operating capital to support if your plan misses the mark. Make sure that you have backups in place. But don’t forget to bet.

You can’t do it all

Photo by Esteban Lopez on Unsplash

“As society grew more complex, corporations grew more powerful, and citizens demanded more from the government, elected officials simply did not have time to regulate so many diverse industries. Nor did they have the specialized knowledge required to set rules for fair dealings across financial markets, evaluate the safety of the latest medical device, make sense of new pollution data, or anticipate all the ways employers might discriminate against their employees on account of race or gender”

— THE WORLD AS IT IS Page 495–496

Presidential Context: This section is concerning the passage of new regulations, mostly Green in nature, and the push back that his administration received. The issue he found was that the world had simply gotten too complex and interdependent to survive without experts monitoring our economy and industries.

The Enterpernial lesson: Be aware of complexity. You will make:

  • Technical decisions that will impact how you go to market
  • Marketing decisions that will affect your pricing
  • Personnel decisions that will affect your technical capabilities

It will not always be clear how each of these decisions will affect your business or how intricate the interdependencies are. During your decision-making process, you should look for the possible dependencies and factor them into your decisions.

Finally, don’t be afraid to ask experts for advice. They will be able to help you cut through the complexity and bring value to your decision-making process.

As you read through A Promised Land, there are entertaining, frustrating, and insightful stories. Some decisions you will not agree with, and some President Obama will not agree with in hindsight.

A US President might not be the apparent source of business leadership advice. However, at the core, the modern President’s portfolio is the same as any large CEO you have:

  1. Make strategic decisions
  2. Build a team that can turn the strategic decisions into tactical tasks
  3. Implement the technical tasks
  4. Handle the results in the company and the press

Go forth … Lead your team … and remember, Yes We Can!

Automation Components Previous post A story of Ambient Lights, Automation, and a Happy Partner
Tasker, Home Assistant and Podcast Next post Automate your Podcast Downloads with Tasker and Home Assistant