We ended last week's newsletter with the founder who decided to go all in again.

He and his wife decided they were ready to "go for another championship".

He told me they had so many unpulled levers between Amazon, international expansion, and a bigger wholesale push that he's ready to start pulling some of them.

I loved the clarity of the decision, but making the decision is only step one.

"We're going all in" sounds like a plan, but it doesn't become one until you put guardrails around it.

For one founder, going all in means taking EBITDA down to negative 10% and investing in five things at once.

For another it means "I was at 15% EBITDA and I'm willing to go down to 5."

Both versions can be "all in" but lead to completely different businesses for the next two years.

Think about poker. When you push all your chips to the table, there's a finite, known payoff. One person calls, you double up. Two people call, you triple up.

You know exactly what you are willing to lose and what you can win.

Business gives you none of that. The stake, the payoff, and the timeline don't exist until you define them.

Going all in is a mindset before it's a set of actions.

It's rarely "my net worth is $20 million, so I'm putting $20 million into the business."

It's the guardrails you put around your time, your calendar, and your capacity. If I've decided to go all in, that means I'm saying no to other things. The conference invite. The angel investment. The rental property. Maybe a couple of family vacations.

“All in” is mostly a list of things you're not going to do.

When I asked this founder what it meant for him he said, "I'm fine with going break even for a year, but I don't want to go negative."

That guardrail is what turns the decision into a plan.

It sets the floor and defines his risk tolerance. It tells finance exactly what to model: what does the year look like if we run this to break even, versus holding 5% EBITDA, versus 10%?

Now every decision, from the size of the marketing bet to the timing of the next hire, has something to be measured against.

The “all in” instinct is to tackle everything immediately. Identifying which SKUs to put on Amazon, making new hires, rebranding, doing wholesale, testing new marketing initiatives.

But doing everything at once = nothing gets done.

So the real questions become: over what time period, and in what order?

My answer on order is almost always the same: solve the team first, because the team executes everything else. Every lever on the list is only as good as the people pulling it.

We started with new marketing hires. His instinct was "I need to hire a CMO." But what he actually needs is a VP of marketing to own the day to day.

The CMO-level strategy can come from a mentor he already has. He gets the executive thinking without the executive salary, and the hire he makes is the one who does the work.

Then come the levers.

Could he do wholesale, Amazon, and international all at the same time? Sure.

But each one makes its own demand on the bank account. The better wholesale goes, the worse his cash flow looks, because big retail partners pay on terms. The more he leans into Amazon, the more inventory he has to carry, because now he's stocking multiple locations.

Stack all three on top of new salaries and even a good year can leave you short on cash.

That's why the guardrail from earlier does the sequencing for him. Break even is the floor, so the order of initiatives becomes whatever the floor allows.

Maybe Amazon goes first, and if it unlocks another $30K a month of contribution margin, the next hire is paid for.

It's about earning the next step. Each lever has to pay for the one that comes after it.

This founder's version of winning is directional: get to $30 million. The number matters less than having one, because you have to set the win condition yourself or you'll never know whether the all in worked.

Commitments that stick have a definition of winning. Ones that dissolve after a few quarters never did.

Then write it down and communicate it to the stakeholders involved.

Your team, because they're executing it.

Your suppliers, because your plan may be bigger than their capacity, and you want to know that now.

Your fractional partners, because if your CFO or your agency comes back and says great plan, I can't give you additional bandwidth, better to hear it on day one than in month six.

And your spouse and your friends, so they know what to expect from you.

Saying it out loud — even if the only person holding you to it is you — makes it far more likely to stick.

So before you tell anyone you're going all in, answer four questions:

The floor does the sequencing. The win tells you when to stop. That's what makes it a plan.

Save this for your next planning session — or for the day you catch yourself saying "we're going all in."

One last thing before you picture a year of joyless discipline to hit your goals: going all in doesn't mean the fun stops. 

There's a line item I make room for in these budgets that does the opposite. That's next week's issue.

— Sam

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