The Entrepreneur Apprenticeship And The Open-And-Shut Side Hustle
Be a number two inside a team of under twelve first, then run 90-day businesses that are designed to end.
- Difficulty
- Easy
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 93%
Priestley's advice to someone starting out is explicitly sequenced and explicitly against going straight to founding. Step one is an entrepreneur apprenticeship: work in a small team of fewer than twelve people where you have direct contact with an entrepreneur, ideally one who has some personal brand — 5,000 to 50,000 followers — and an elegant business model that inspires you. It does not have to be what you want to do; you are there to learn the new rules, specifically how they build a personal brand and how they build a business that scales, communicates and sells to people anywhere in the world. He is blunt that you do not want to become an entrepreneur straight away — it is too big a shift, and you need to be a number two. Step two is side hustles, defined precisely as an open-and-shut business case: within 90 days you start something and finish it. You are not getting into a long-term thing; you start, see how it goes, and it ends. The design constraint is the ending, because it delivers the learning experience without the ongoing obligation, and it creates a clean point to reflect on what worked and decide whether to continue.
Origin
Priestley was a number two himself. He had a mentor and worked for what he calls an amazing guy for two years, during which the business went from zero to £6 million and from zero to 60 people in a single year. His teenage side hustles were nightclub parties — agree the venue, run a promotion phase, run the party, split the money at the end of the night — and selling Valentine's roses door-to-door in a tuxedo, an idea-to-finish cycle of about three weeks.
Core principles
- 01Do not become an entrepreneur straight away; be a number two.
- 02Fewer than twelve people, direct contact with the entrepreneur.
- 03Pick a mentor with a personal brand and an elegant business model.
- 04A side hustle is an open-and-shut case with a defined ending.
- 05You cannot learn to ride a bike from books and videos.
How to run it
- 1
Find a sub-twelve-person team with a visible entrepreneur
The size cap matters because it guarantees direct contact. Priestley's specification for the entrepreneur is someone with roughly 5,000 to 50,000 followers and an elegant, scalable business model that inspires you.
Pro tip It does not need to be the industry you eventually want — you are there for the rules, not the sector.
Watch out A large company removes the direct contact that is the entire point of the apprenticeship.
- 2
Study the two mechanisms specifically
How is this person building their personal brand, and how are they building the business so it can scale? How do they communicate with people anywhere in the world, and how do they sell to them?
Pro tip Naming the two questions in advance turns a job into a curriculum.
Watch out Absorbing the role without watching the brand and business mechanics wastes the placement.
- 3
Fall back to co-founding, then to side hustles
If you cannot get the apprenticeship, become a co-founder with someone more experienced than you. If you cannot do that either, run small side hustles.
Pro tip The ladder is ordered by how much you learn on someone else's dime.
Watch out Skipping straight to the bottom rung means learning everything by paying for it yourself.
- 4
Design each side hustle to end within 90 days
Start something and finish it inside 90 days. It is not an ongoing venture — you start, see how it goes, and it ends. Then reflect on what worked and what did not, and decide whether to continue.
Pro tip Priestley's roses hustle ran about three weeks from idea to supplier to door-to-door sales to finished.
Watch out An open-ended first venture ties up the time and capital you were supposed to be using to learn.
- 5
Publish while you learn
Priestley reframes writing as publishing — making public. Only about 3% of LinkedIn's billion users publish regularly and under 1% publish weekly; only 4% of YouTube's 2.7 billion users have an account and a fraction are active.
Pro tip You are not competing with a billion people; you are competing with the 1% who create.
Watch out Journaling is private and does not produce feedback on whether the idea is any good.
In the wild
He worked for a mentor for two years in a business that went from zero to £6 million in revenue and from zero to 60 people in a single year.
→ He got the entrepreneur apprenticeship first, which is why he tells 21-year-olds to start there rather than founding immediately.
Bartlett committed at 24 to writing a tweet every day, screenshotting it and posting to Instagram — his girlfriend knew he disappeared for an hour at 7pm to think of something to say.
→ Three downstream consequences: two million Instagram followers; learning to communicate ideas concisely and with impact; and a daily forcing function to condense the day's experience into a piece of truth that would otherwise have passed him by.
Common mistakes
Founding straight out of the gate
Priestley calls it too big a shift. The apprenticeship exists because you can learn the new rules on someone else's dime rather than paying for them with your own failure.
Turning a side hustle into an ongoing venture
The defined ending is the design feature. It delivers the learning without the ongoing connection to the business, and creates the reflection point.
Trying to learn entrepreneurship from content
Books and YouTube are great, and Priestley notes he had neither — business books had to be ordered in and audio content came on £1,000 cassette sets. But you cannot learn to ride a bike through books and videos.
Is it for you?
Best for
People in their late teens to thirties deciding whether to start something now or work for someone first.
Not ideal for
Experienced operators who have already run businesses — the apprenticeship rung is behind them.
From the transcript
“you do not want to become an entrepreneur straight away it's too big a shift you need to be a number two”
“a side hustle is an open and shut business case so within 90 days you're going to start something and finish something”
“you can't learn to ride a bike through books and videos you have to get on the bike”
From the episode
The Money Making Expert: The 7,11,4 Hack That Turns $1 Into $10K Per Month! This 90 Day Rule Will 10x Your Income! Daniel Priestley
Daniel Priestley