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The GTM bets that shouldn't have worked, and did
One grew revenue 50x after half his team quit over the strategy. One brought in 50K signups in a single day with no paid budget. One generated 100M+ views from a stunt that took 50 hours to conceive. One asked every prospect to demo the product themselves instead of demoing it for them.
None of them followed the safe playbook. They treated GTM like an experiment, moved before they had proof, and made bets most founders would never get approved.
HubSpot for Startups documented all 6 stories in the free Bold Bets Playbook. The risks they took, why it was risky, and what it returned.
THE WEEK THAT WAS
Last week the show turned a corner. After three weeks of looking at how things come apart, this week was the first one about putting them back, starting with the smallest unit of rebuilding there is: a single broken pattern.
Monday, in The First Pattern I Broke, I told you about a half-written email, a client call I wanted to push, and the first time I caught my pattern while it was still moving and did not feed it. The big takeaway: breaking a pattern does not feel like winning. It feels like standing in a doorway not knowing what to do with your hands.
Wednesday, in The Interruption, I took that moment apart and showed the machinery. There is a gap between your trigger and your pattern. You find it through three tells, the body signature, the reasonable script, the false urgency, and you fill it with three things, a name, a question, and the willingness to do the right thing badly.
Friday, in The Text I Didn't Send, I gave you a single scene. Eleven at night, a paragraph that felt completely justified, a thumb on the send button. And the quiet realization that the patterns you break with no witness and no credit might be the most important ones you break.
THE QUESTION BEHIND THE EPISODES
SIT WITH THIS ONE
Where is the gap in your own pattern, and what would it take for you to feel it before the action instead of after? You have a half second you have never used. The whole week was about finding it. So: when does yours open, and what is the very first tell that it is about to?
THREE THINGS WORTH HOLDING
The pattern calls itself the smart move. It never announces itself as the pattern. It shows up sounding like wisdom, like the professional play, like the reasonable thing any competent person would do. If a course of action feels obviously smart and also weirdly familiar, that pairing is the tell. Smart plus familiar is often just the pattern in a good suit.
You break it in the gap, not the action. By the time you are in the action, it is too late, the pattern already has the wheel. The whole leverage point is the small space between the trigger and the move. Learn your three tells so you can feel that space opening, because a gap you cannot feel is a gap you cannot use.
The invisible reps count the most. The pattern you interrupt with nobody watching, the text deleted at midnight, the spiral set down before anyone knew it started, earns you no credit and no applause. It is also where the realest work happens, because there is no audience to perform for. Just you, choosing not to make a new mess.
THE RESET
Here is the reset. Last week asked a lot of you. It asked you to start doing something, not just understand something. And the doing is harder than the understanding, and it is also less satisfying at first.
So I want to reset your expectations, the same way I had to reset mine. You are going to miss the gap. A lot. You will be three steps into the pattern before you remember the gap exists. That is not failure. That is the normal opening condition of a skill you have had for days going up against a pattern you have had for years.
The measure is not whether you catch it every time. The measure is whether you catch it more times this month than last month. That is it. That is the whole scoreboard. Slow, unglamorous, real.
And when you do catch it, do not expect a feeling of triumph. Expect the doorway. Expect to stand there a little stuck, a little uncomfortable, holding a pattern you very much want to put down. Standing there is the win. The win just does not feel like one yet.
ONE THING TO TRY
Run the three-step gap drill on one real moment. This week, pick one moment where you feel the pull of your pattern, and run the sequence from Wednesday's episode. One: name it, silently, this is the pattern. Two: ask the question, where does this actually lead, based on every other time. Three: if you can, do the opposite thing badly, clumsily, without confidence. You do not need all three to land perfectly. Even getting to step one changes the moment. Just run the drill once, for real, and see what happens.
The Sunday Reset is the free companion to Grace Over Guilt. If a friend forwarded this to you, you can subscribe so it lands in your own inbox every Sunday morning. New episodes drop Monday, Wednesday, and Friday.
Dan
Orlando, Florida
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