What Poker Taught Me About Business Targets
The founders who worry me most aren't the ones without a plan. They're the ones who spent three days on strategy and came back with a mission statement, a market thesis, and not a single concrete target.
I work with a founder whose company is well past $50 million in revenue. He's brilliant — genuinely visionary. He can describe in vivid detail what the company looks like in ten years. He can see every opportunity, every channel, every product expansion, every possible path forward.
When I asked him recently what the company's goal was for the next twelve months, he said, "We're in the process of re-forecasting. It's a little fuzzy."
When I pressed further, he told me he had a mind map with 47 focus areas on it. Forty-seven. And he couldn't pick three.
This isn't a beginner's problem. It's actually worse the more successful you are, because you can see more possibilities. The vision gets clearer and the commitment gets harder. Another founder I coach — earlier stage, just entered a new partnership — spent three days in another city mapping out strategy with her partner. When I asked what they'd decided, she talked for ten minutes about the opportunity. But when I asked a simpler question: how many deals do you want to close this year? She couldn’t give me a solid answer, "as many as we can."
Her partner had the same answer for everything. How big? As big as possible. How much revenue? We'll see what happens. Here’s two people building a business together, both smart, both energized, and neither one willing to put a number on anything.
These answers sound like ambition. They're not. They're what people say when they're afraid to make a commitment they might miss. But the thing about keeping it vague — it doesn't reduce the anxiety. It just spreads it across everything, so you're never quite sure if things are going well or poorly.
The problem isn't that founders don't know what to aim for. It's how they think about what happens when they miss.
Business Is Poker, Not Chess
Annie Duke — a World Series of Poker champion who went on to study decision-making — has a line I think about often: life is poker, not chess.
In chess, there's no hidden information. Make the right moves and you win. But business doesn't work that way. In business, like in poker, you're making decisions with incomplete information, and the outcome is shaped by things you can't control. Market timing, other people's choices, luck, forces you can't even see. You can make the best possible call and still lose. You can make a terrible call and still win.
The trap most founders fall into is treating business like chess — grading the quality of their decisions based entirely on the outcome. Duke calls this "resulting." You set a revenue target, you miss it, and you conclude the target was wrong — or worse, that you were wrong.
But that's not what happened.
You made a call based on what you knew, and reality included variables you couldn't control. The miss doesn't mean the decision was bad. It means the outcome didn't land. Those are very different things.
That was exactly what was happening with the founder at $50 million. He could see all 47 paths and couldn't commit to one because — what if he picked wrong? What if the sequencing wasn't right? He said it himself: "I don't have much confidence that a right answer exists."
I told him what I tell everyone in that spot: there is no right answer. You just have to make a bet.
When I used to play poker, I could always tell I was going to do well when the person across from me was playing scared — never committing to their hand because they were trying to protect what they had. They were making decisions based on what they were afraid to lose. That's a losing strategy in poker, and it's a losing strategy in business too.
Goals vs. Bets
The earlier-stage founder — the one who said "as many as we can" — eventually told me the real reason. She said, "I think I'm just nervous about feeling bad if I don't hit the goal." There it was. Not confusion about what to aim for. Fear of what missing would mean about her.
Another founder I work with used to describe every outcome as a "consequence" — not a result, a consequence. So every number he hit was a reward and every number he missed was a punishment. It kept him frozen. He couldn't commit to anything because every target felt like a verdict on him personally.
I asked him to stop using the word "goal" entirely and start using the word "bet." Not because it sounds better — because it changes the relationship with the number. A goal you miss is a failure. A bet that doesn't come in is information. When you frame it as a goal and miss, you ask: what's wrong with me? When you frame it as a bet and it doesn't come in, you ask: what data did I have? What did I miss? What would I do differently?
He put it better than I could: "A bet isn't binary. It's a continuum." And that was the unlock — moving from pass/fail to process quality. It's not whether I'm right or wrong. That's not even interesting. What's interesting is whether I'm getting better at making the call.
How to Make a Good Bet
You already know how to do this. You make bets every day — on hires, on deals, on timing, on whether a partnership is worth pursuing. You gather information, weigh the odds, make a call, and adjust when new data comes in.
Here's what it looks like in practice.
Start by finding your vague spots. Where are you using language like "significant growth" or "scale revenue" or "more customers"? Those are the places where you're avoiding commitment. “More customers” isn't a plan. How many? Where? Which ones? Through what? If you can't be proven wrong, it's not a bet — it's a wish.
Then look at what you already know. Most founders think they need perfect information before they can commit to a number, so they wait. But you already have data — you just haven't compiled it. The founder who said "as many as we can" had already closed five deals. I asked her: you know the average deal size, the sales cycle, the conversion rate. You can make an informed bet on what twelve months looks like. Start with what you have — past results, pipeline, market signals, your own gut sense from being in the work every day.
Name the number. This is where most people stall. They'll circle around it, qualify it, add caveats — anything to avoid writing down a specific figure they might not hit. Write it down anyway, even if it feels made up. Especially if it feels made up. You're not writing a prophecy. You're creating something to move toward, push against, and measure yourself by. You're spending too much time dating these targets — commit to one.
Assign a rough likelihood. This is the step that changes everything, and most people skip it. Put a probability on your own target — not a precise percentage, just an honest gut sense. 70%? 50%? The reason this matters is that it breaks the binary. A goal is either hit or missed. A bet with a 60% likelihood is a hypothesis. You made a call, you assigned your confidence, and now the outcome is information about the quality of your thinking rather than a verdict on you. "I think there's about a 65% chance we hit this given what I know right now" is a fundamentally different relationship with a target than "our goal is $3M." The first keeps you curious. The second sets you up to feel like you failed.
Define what would change the bet. At Joany, I hit my year end goal in a month. So I pushed the targets higher — way more aggressive. Then they got too aggressive and I had to dial back. The bet updates as data comes in. You don't stop when you hit the number. You change the bet.
Swap the language with your team — out loud. "Consequences" becomes "results." "Goals" become "bets." And the most important one: "Was that the right or wrong decision?" becomes "How strong was our process?" In practice, that sounds like this: instead of "we missed our goal this quarter," it's "our bet didn't come in — what did we learn about why, and what do we adjust for next quarter?" The emotional charge drops. The quality of the conversation goes up.
Something to Push Against
There's a reason this avoidance runs so deep, and it's not laziness or lack of ambition. A founder I work with put it this way — he'd built his entire sense of self-worth on external results. How much revenue, how much money, what people thought of him. I told him: that's self-esteem built on sticks. It's dependent on everybody else, not on yourself. And when your identity is tied to hitting targets, the safest place to live is having no targets at all. No number means no miss. No miss means no threat to who you think you are.
But real confidence — real grit — doesn't come from avoiding the hard thing. It comes from going through it. From quitting the job you were afraid to quit and realizing you're still here. From getting fired and surviving. From setting a number, missing it, evaluating your process, and making a better bet the next time. Those are the small things that build something solid underneath you — something that doesn't collapse when the outcome doesn't go your way.
The founder who used "consequences" for everything came back the following week with actual numbers. Rough, imperfect, based on what he knew. He'd assigned a likelihood to each one. And for the first time in months, he could look at a missed target and ask "what did I get wrong about my assumptions?" instead of "what's wrong with me?"
That's all a target really is. Not a promise you'll be punished for breaking. Just a stake in the ground — something to move toward, measure against, and then move past.
You don't stop when you hit it. You change the bet.
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