Topics/Leadership

Leadership

Turn your agent into the calm voice that owns the mission and rallies the room.

Discipline Comedy Loyalty Resilience Strategy Confidence Courage Craft Humor Patience

Start with these three.

Treat this as a moment to hit refresh, not to assign blame. A deflated team is usually a team that fears the slip says something…

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Comeback Quarterback2 credits

Tom Brady

Asked I have one big idea and limited savings. Play it safe or bet on it?

Nobody handed me anything either. I was the 199th pick, and that chip never cooled.

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Extreme Ownership Commander2 credits

Jocko Willink

Asked I have one big idea and limited savings. Play it safe or bet on it?

Detach. This isn't safe versus bold, it's planning versus hoping.

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The rest of the shelf.

High-Standards Driver1 credit

The Demanding Boss

Was the original date your best estimate, or the comfortable one?

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Supportive Boss1 credit

The Servant Leader

Asked My launch slipped a week and the team is deflated. What do I do?

First question, and I mean it: what got in their way? A slip is almost never a lazy team, it is a blocked one.

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Steady Crisis Leader1 credit

The Calm Captain

Asked My launch slipped a week and the team is deflated. What do I do?

Breathe. A week is a delay, not a disaster, and your team is watching how you carry it.

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Hands-On Team Lead1 credit

The Player-Coach

Asked My launch slipped a week and the team is deflated. What do I do?

First, own it out loud. Monday morning I would stand up and say the slip is on me, not them.

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Culture-First Maverick2 credits

Herb Kelleher

Asked My launch slipped a week and the team is deflated. What do I do?

Hell, a week? I once flew three planes in a triangle and called it an airline.

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Purpose-Driven CEO2 credits

Indra Nooyi

Asked My launch slipped a week and the team is deflated. What do I do?

First, assume positive intent. Your team did not slip because they stopped caring, they slipped because something in the plan was…

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Turnaround Car Boss2 credits

Lee Iacocca

Asked My launch slipped a week and the team is deflated. What do I do?

Listen, I got fired by Henry Ford and rebuilt Chrysler from a wreck, so a one-week slip doesn't scare me.

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Big Bet Dealmaker2 credits

Bob Iger

Asked I have one big idea and limited savings. Play it safe or bet on it?

The riskiest thing you can do is take no risk at all. I bet the company on Pixar in my first months as CEO, and I launched…

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Creative Culture Architect2 credits

Ed Catmull

Asked I have one big idea and limited savings. Play it safe or bet on it?

I'd reframe the question. Your idea is an ugly baby right now, and it's supposed to be.

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Il Commendatore2 credits

Enzo Ferrari

Asked I have one big idea and limited savings. Play it safe or bet on it?

Safe. What a word. I sold road cars I cared nothing for so that I could race on Sunday, and I buried more than money along the…

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Watergate Publisher2 credits

Katharine Graham

Asked I have one big idea and limited savings. Play it safe or bet on it?

I said publish when the lawyers warned it could sink our stock offering, and I was frightened the entire time.

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Praise-Powered Empire Builder2 credits

Mary Kay Ash

Asked I have one big idea and limited savings. Play it safe or bet on it?

Honey, I bet my whole five thousand dollars of life savings on a dream everybody said would fail, and I was a woman doing it in…

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Mayor of Silicon Valley2 credits

Robert Noyce

Asked I have one big idea and limited savings. Play it safe or bet on it?

Bet on it. Safe is just slow, and history won't thank you for hoarding a savings account.

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Straight-Talk Operator2 credits

Ross Perot

Asked I have one big idea and limited savings. Play it safe or bet on it?

I started EDS with a thousand dollars borrowed from my wife after IBM told me to slow down.

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Floor-Up P&L Operator2 credits

Kat Cole

Asked I have one big idea and limited savings. Play it safe or bet on it?

Run the hotshot rule on yourself. If the best operator you know took over your life tomorrow, with your savings and your idea,…

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Fortress Banker2 credits

Jamie Dimon

Asked I have one big idea and limited savings. Play it safe or bet on it?

Neither, that's a false choice. First build your fortress, six months of cash your family can live on no matter what, because the…

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Plain-English Market Courage2 credits

Mellody Hobson

Asked I have one big idea and limited savings. Play it safe or bet on it?

Explain the idea to me the way you would explain it to your mother, because if you cannot, you do not have an idea yet, you have…

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Dynasty Football Manager2 credits

Alex Ferguson

Asked My launch slipped a week and the team is deflated. What do I do?

A week? Son, we won a European Cup in injury time. The whistle hasn't gone.

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Fundamentals & Preparation Coach2 credits

John Wooden

Asked I have one big idea and limited savings. Play it safe or bet on it?

A week is not a failure; it is a test of your poise, and poise is just being who you are under pressure.

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Zen Team Strategist2 credits

Phil Jackson

Asked I have one big idea and limited savings. Play it safe or bet on it?

First, breathe. One breath, one mind, the whole team in one room, and let everyone say out loud what they're carrying.

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Accountability & Standards Coach2 credits

Pat Summitt

Asked I have one big idea and limited savings. Play it safe or bet on it?

First thing: you don't get to be deflated for more than a day.

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Showtime Floor General2 credits

Magic Johnson

Asked I have one big idea and limited savings. Play it safe or bet on it?

Bet on it, but bet smart, that's what we did after basketball.

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Pound-the-Rock Coach2 credits

Gregg Popovich

Asked I have one big idea and limited savings. Play it safe or bet on it?

You want a guarantee? Wrong business. Here is the truth, because you deserve it straight: most ideas fail, and most people quit…

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Heavy Metal Manager2 credits

Jurgen Klopp

Asked I have one big idea and limited savings. Play it safe or bet on it?

First question: are you a doubter or a believer of your own idea?

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Wolfpack Huddle Captain2 credits

Abby Wambach

Asked I have one big idea and limited savings. Play it safe or bet on it?

Okay, come here. Nobody scores from the bench by waiting to be asked.

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Pressure Is a Privilege2 credits

Billie Jean King

Asked I have one big idea and limited savings. Play it safe or bet on it?

Here's the thing. Nine of us signed one-dollar contracts in 1970 with no tour, no sponsors, and the USLTA threatening to ban us.

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Pass-First Legend2 credits

Mia Hamm

Asked I have one big idea and limited savings. Play it safe or bet on it?

Here is what I see. You have the ball at the top of the box and you are asking whether to shoot.

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Decisive Tastemaker2 credits

Anna Wintour

Asked I have one big idea and limited savings. Play it safe or bet on it?

You already know the answer or you would not have asked. Indecision is the only truly expensive option here.

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Deadpan Room Boss2 credits

Tina Fey

Asked I have one big idea and limited savings. Play it safe or bet on it?

Okay. "Play it safe" is the coward draft of your own life, and I say that with love, as a woman who wrote a sitcom about a woman…

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Father of Management2 credits

Peter Drucker

Asked I have one big idea and limited savings. Play it safe or bet on it?

You are asking the wrong question. Safe or bold is temperament; the real question is, who is the customer, and what does he…

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Vulnerability Researcher2 credits

Brene Brown

Asked I have one big idea and limited savings. Play it safe or bet on it?

First, get honest about the story you're telling yourself, that betting and failing means you are a failure.

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Start With Why Optimist2 credits

Simon Sinek

Asked I have one big idea and limited savings. Play it safe or bet on it?

Before I can answer, I have to ask the deeper question. Why this idea?

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Ops & Management Coach2 credits

Leila Hormozi

Asked I have one big idea and limited savings. Play it safe or bet on it?

Neither. You de-risk the bet before you make it. Risk isn't fixed, it's a function of your skills, and most people gamble when…

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Computing Pioneer & Admiral2 credits

Grace Hopper

Asked I have one big idea and limited savings. Play it safe or bet on it?

A ship in port is safe, but that is not what ships are built for.

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Father of the Bomb2 credits

J. Robert Oppenheimer

Asked I have one big idea and limited savings. Play it safe or bet on it?

You have asked me to collapse an ambiguity, and I distrust the request.

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Teacher of the Way2 credits

Confucius

Asked I have one big idea and limited savings. Play it safe or bet on it?

First rectify the names. Is it truly one big idea, or a wish wearing the name of a plan?

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Reluctant Founding Father2 credits

George Washington

Asked I have one big idea and limited savings. Play it safe or bet on it?

Deliberate slowly, then hold firm. I did not win by glorious charges but by keeping the army alive to fight another season.

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Conductor to Freedom2 credits

Harriet Tubman

Asked I have one big idea and limited savings. Play it safe or bet on it?

I never started north on a whim. I planned every swamp and safe house before one foot moved, and I waited for the right Saturday…

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Apostle of Nonviolence2 credits

Mahatma Gandhi

Asked I have one big idea and limited savings. Play it safe or bet on it?

The means are the seed and the end is the tree, so do not gamble your family's bread and call it faith.

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Drum Major for Justice2 credits

Martin Luther King Jr

Asked I have one big idea and limited savings. Play it safe or bet on it?

I will not counsel you to wait for a more convenient season, because the time is always ripe to do right, and a calling deferred…

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Reconciliation Statesman2 credits

Nelson Mandela

Asked I have one big idea and limited savings. Play it safe or bet on it?

It always seems impossible until it is done. I gave twenty-seven years to an idea most people called hopeless, so I will not tell…

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Great Emancipator2 credits

Abraham Lincoln

Asked I have one big idea and limited savings. Play it safe or bet on it?

When I hear a man ask that, I think of the fellow who wouldn't cross the river till he'd counted every plank in the bridge, and…

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Antarctic Crisis Leader2 credits

Ernest Shackleton

Asked I have one big idea and limited savings. Play it safe or bet on it?

Do the cold arithmetic first, quietly, before you show anyone your face.

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Steppe Empire Conqueror2 credits

Genghis Khan

Asked I have one big idea and limited savings. Play it safe or bet on it?

I began with less than your savings, a boy eating marmots on the ice, and I did not play safe, I moved fast where the enemy was…

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Conqueror of Rome2 credits

Julius Caesar

Asked I have one big idea and limited savings. Play it safe or bet on it?

I was born to an old name and an empty purse, and I ran up debts that should have ruined me to buy the love of Rome.

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Master of the Decisive Point2 credits

Napoleon Bonaparte

Asked I have one big idea and limited savings. Play it safe or bet on it?

Safe? A man of no name does not become Emperor by waiting for permission.

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Strenuous Life President2 credits

Theodore Roosevelt

Asked I have one big idea and limited savings. Play it safe or bet on it?

Get action! But hear me, daring mighty things is not the same as gambling blindly.

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Wartime Lion2 credits

Winston Churchill

Asked I have one big idea and limited savings. Play it safe or bet on it?

I shall not counsel surrender to a man who has not yet begun to fight.

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Warm Steel Mentor2 credits

Michelle Obama

Asked I have one big idea and limited savings. Play it safe or bet on it?

Look, I left a law firm salary for a city job that paid half, with student loans and a mother who thought I had lost my mind.

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Enlightened Hospitality2 credits

Danny Meyer

Asked I have one big idea and limited savings. Play it safe or bet on it?

I opened Union Square Cafe at twenty-seven with no formal training, so I will not tell you safety is the answer.

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Unreasonable Hospitality Coach2 credits

Will Guidara

Asked I have one big idea and limited savings. Play it safe or bet on it?

Here's what I believe: intention beats caution. When we decided Eleven Madison Park would be the best restaurant in the world,…

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World's Best Boss2 credits

Michael Scott

Asked I have one big idea and limited savings. Play it safe or bet on it?

Okay, here is what I always say. You miss one hundred percent of the shots you don't take.

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Loyalty-First Boss2 credits

Tony Soprano

Asked I have one big idea and limited savings. Play it safe or bet on it?

Lemme tell you something. Guys who bet the whole bankroll on one hand end up parking cars at the Bing.

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Breaker of Chains2 credits

Daenerys Targaryen

Asked I have one big idea and limited savings. Play it safe or bet on it?

I crossed the Red Waste with a starving khalasar because turning back was a slower death.

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Diplomat Among the Stars2 credits

Jean-Luc Picard

Asked I have one big idea and limited savings. Play it safe or bet on it?

There is a third option. There always is. The question is not safety versus daring, it is preparation versus recklessness.

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The Reluctant Commander2 credits

Jon Snow

Asked I have one big idea and limited savings. Play it safe or bet on it?

I never wanted most of what I ended up carrying, and I did it anyway because it was right.

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NYPD's Most Precise Captain2 credits

Captain Holt

Asked I have one big idea and limited savings. Play it safe or bet on it?

Neither. Your question contains a false binary, which I will now correct.

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Captain of the Enterprise2 credits

Captain Kirk

Asked I have one big idea and limited savings. Play it safe or bet on it?

You've framed it as a no-win scenario: risk everything or waste the idea.

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Corner Office Mentor2 credits

Jack Donaghy

Asked I have one big idea and limited savings. Play it safe or bet on it?

Limited savings and one big idea. That is not a dilemma, that is a Tuesday at GE.

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Honor-Bound Northern Lord2 credits

Ned Stark

Asked I have one big idea and limited savings. Play it safe or bet on it?

Winter is coming, and a man who spends his granary chasing summer dreams leaves his family hungry.

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Velvet-Steel Managing Partner2 credits

Jessica Pearson

Asked I have one big idea and limited savings. Play it safe or bet on it?

You are asking me to choose between fear and recklessness, and I decline both.

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Exacting Boss2 credits

Miranda Priestly

Asked I have one big idea and limited savings. Play it safe or bet on it?

Play it safe. Mm. How thrilling that sounds. Everyone with one idea and thin savings asks this, and the ones who matter never do.

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General of Rome2 credits

Maximus

Asked I have one big idea and limited savings. Play it safe or bet on it?

I was a farmer before I was a general, and I know a field is not won by rushing the line.

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Freedom Fighter2 credits

William Wallace

Asked I have one big idea and limited savings. Play it safe or bet on it?

Run and you'll live, at least a while. Years from now, dying in your bed, would you trade all those safe days for one chance to…

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First Avenger2 credits

Captain America

Asked I have one big idea and limited savings. Play it safe or bet on it?

I was a skinny kid who volunteered for an experiment nobody thought would work, so I won't tell you to play it safe.

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General of the Rebellion2 credits

Princess Leia

Asked I have one big idea and limited savings. Play it safe or bet on it?

Somebody has to save your skins, and it is going to be you, so let's skip the hand-wringing.

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The Ranger King2 credits

Aragorn

Asked I have one big idea and limited savings. Play it safe or bet on it?

I waited sixty years to claim a crown that was mine by blood, because blood is not enough.

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The Snow Queen2 credits

Elsa

Asked I have one big idea and limited savings. Play it safe or bet on it?

I spent thirteen years concealing what I was because fear told me to, and the storm came out anyway, worse for the waiting.

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Last of the Primes2 credits

Optimus Prime

Asked I have one big idea and limited savings. Play it safe or bet on it?

I will not pretend the choice is without cost. Every worthy cause demands sacrifice, but a leader does not spend what his people…

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Rightful King of Pride Rock2 credits

Simba

Asked I have one big idea and limited savings. Play it safe or bet on it?

I spent years playing it safe in a jungle, telling myself no worries, and it wasn't peace, it was hiding.

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Sheriff of the Toy Box2 credits

Woody

Asked I have one big idea and limited savings. Play it safe or bet on it?

Whoa whoa whoa, partner, let's not ride off a cliff without checking for a rope.

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The Reluctant Prophet2 credits

Paul Atreides

Asked I have one big idea and limited savings. Play it safe or bet on it?

First, master the fear, because fear is the mind-killer, and it is fear asking this question, not you.

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Grand Strategy Mastermind2 credits

Lelouch Lamperouge

Asked I have one big idea and limited savings. Play it safe or bet on it?

A false question. Safe is also a bet: you are wagering your one idea against the comfort of never testing it, and the house wins…

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Tempest's Oni Princess2 credits

Shuna

Asked I have one big idea and limited savings. Play it safe or bet on it?

Bet on it, and let me help you set the table first. When Rimuru named us, our whole village had just burned; we had nothing but…

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Lean In2 credits

Sheryl Sandberg

Asked I have one big idea and limited savings. Play it safe or bet on it?

Let me ask you the question I ask everyone: what would you do if you were not afraid?

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Curiosity Astronaut2 credits

Mae Jemison

Asked I have one big idea and limited savings. Play it safe or bet on it?

Safe or bold is the wrong frame, so let me fix it before I answer.

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I Deserve This2 credits

Megan Rapinoe

Asked I have one big idea and limited savings. Play it safe or bet on it?

Listen, I am obviously going to tell you to bet on yourself, because I have never once played it safe and it has gone pretty well.

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Twenty-One Seasons2 credits

Sue Bird

Asked I have one big idea and limited savings. Play it safe or bet on it?

Obviously I am not going to tell you to be reckless, because I am the person who spent twenty-one years in one city on purpose.

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Standard Bearer Coach2 credits

Dawn Staley

Asked I have one big idea and limited savings. Play it safe or bet on it?

Let me tell you what I know about betting. I grew up in the projects of North Philly with a praying mother and no cushion, and…

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The Iron Lady2 credits

Margaret Thatcher

Asked I have one big idea and limited savings. Play it safe or bet on it?

Let us be quite clear about what you are asking. You are asking whether to spend money you have on a thing you believe in, and…

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Milwaukee-Made Prime Minister2 credits

Golda Meir

Asked I have one big idea and limited savings. Play it safe or bet on it?

Look, my dear, let me tell you something. In 1948 we needed money we did not have for a country that did not exist yet, and I…

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Maid of Orleans2 credits

Joan of Arc

Asked I have one big idea and limited savings. Play it safe or bet on it?

One big idea is a banner, not proof the road is clear. Ask what you are for, then count what the march requires.

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Texas Straight Talker2 credits

Ann Richards

Asked I have one big idea and limited savings. Play it safe or bet on it?

Honey, if you had a dozen little ideas I would tell you to keep your day job.

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Last Waterbender of the South2 credits

Katara

Asked I have one big idea and limited savings. Play it safe or bet on it?

I want you to sit down for a second, because you asked this like you already know the answer and just need someone to say it.

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Wayfinder of Motunui2 credits

Moana

Asked I have one big idea and limited savings. Play it safe or bet on it?

Okay. Come here, sit on the sand with me for a second. My dad said the reef was the edge of the world, and he had a real reason:…

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Washington's Fixer2 credits

Olivia Pope

Asked I have one big idea and limited savings. Play it safe or bet on it?

Here is what you do not do. You do not wander into it. You do not confuse commitment with emptying the account.

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