The PlaybookHow they actually decided
Real decisions from the conversations: the situation, how they thought it through, and what to take from it. Each one links to the moment it happened.
DecisionsEp. 01, Riley Walker
He fired customers worth millions
- The situation
- Ryco was bootstrapped, so the team has always been paid from what the company earns. Some customers would have made Riley millions.
- How Riley thought about it
- He says he has no framework, only years of reps and one thing he will not trade: a customer who beats up his team is not worth keeping. He thinks of the company as the car he is driving. Say yes to the wrong customer and the wheels pop.
The risk in every decision grows with the team, so protect the people who carry it.
DecisionsEp. 01, Riley Walker
Why Ryco sells courses instead of licensing them
- The situation
- Licensing would mean recurring revenue. Ryco sells schools the courses it builds, and they own them outright.
- How Riley thought about it
- The answer was a photo: brand-new textbooks thrown away at the end of the year, still in plastic. Schools sit in ten-year contracts and teachers end up writing their own curriculum on top of teaching.
A business model can come straight out of the problem you watched happen.
OpportunitiesEp. 01, Riley Walker
How many red cars did you see on the way here?
- The situation
- Riley was working at a restaurant in Tampa to get through college when he met a man who turned out to be an educational publisher.
- How Riley thought about it
- He already knew the problem he cared about, a one-size-fits-all curriculum that had not worked for his sister, so he recognised his way in. He spent the next four years writing math books in his dorm room.
The looking has to come first. Luck can only help once you know what you are looking for.
PeopleEp. 01, Riley Walker
Cut from the team, made its manager
- The situation
- At a baseball tryout in Maine, Riley's friend Tom got cut and walked out upset.
- How Riley thought about it
- Riley ran after him, went back in, and asked the coaches whether the team had a manager. It did not, so he told them to make Tom the manager.
Leadership showed up long before the title did: notice the person walking out, then find them a way back in.
MindsetEp. 01, Riley Walker
The more comfortable you are with yourself
- The situation
- Riley used to be a nervous perfectionist who needed to be right. Four years ago, a call with an investor he had never met would have had him shaking.
- How Riley thought about it
- He had one the morning we recorded and was not nervous at all. His explanation was reps, and being around the right people.
What he would tell himself at 20: don't be so insecure, ask questions, and it's okay to be wrong.
DecisionsEp. 02, Daavi Gazelle
The question that made him quit Visa
- The situation
- Daavi had a lingering feeling at Visa that he should be doing something else, and could not bring himself to leave.
- How Daavi thought about it
- A coach asked him two questions. If you quit, would they ever hire you back? Probably. Do you want to be working here in five years? Absolutely not. Then what do we have to lose?
Many decisions that feel like a cliff are reversible. Check that first.
RiskEp. 02, Daavi Gazelle
A pay cut to work for his mom
- The situation
- After Visa he joined his mom's coaching business, then doing $300,000 a year, on a salary well below what he had been making.
- How Daavi thought about it
- He tells it as hostels, sales calls on a tablet after his computer was stolen, and every call that did not close feeling like letting his mother down. Four years later, he says the business does $700,000 a month.
A leap feels like a pay cut, a lot of weight and a lot of fun, all at once.
OpportunitiesEp. 02, Daavi Gazelle
Every viral video is a free lesson
- The situation
- You cannot watch another entrepreneur's best sales calls. You can watch everyone's best content.
- How Daavi thought about it
- He compares it to watching Michelangelo sculpt for hours. Content is just human psychology: whatever would make you stop on a street corner is what makes you stop scrolling.
When the best work in your field is public, study it like a master class.
MindsetEp. 02, Daavi Gazelle
Running from a tiger, or toward a treasure chest?
- The situation
- So much ambition comes from an insecure place. Does it matter where yours comes from?
- How Daavi thought about it
- The person running from a tiger is probably faster, but you cannot run from one every day; eventually your nervous system shuts down. Walking toward a treasure chest, you can rest and stay curious.
His test is to ask what is actually true. Am I going to die if this does not go well? Almost always, no.
RiskEp. 02, Daavi Gazelle
There's no tiger chasing you
- The situation
- Asked what he would tell someone in their early twenties.
- How Daavi thought about it
- Don't be afraid for things to really work. Time is finite, and you will not die from the uncertainty.
There is no tiger chasing you, so give it a shot.
Timestamps open on YouTube once the episode is out.