Billionaire Memo
Losing My Virginity Richard Branson Read in full · 10 memos drawn

The Library · A calibre in the collection

Losing My Virginity

By Richard Branson.

Author
Richard Branson, in their own name
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10 memos to date

Losing My Virginity is the book people quote when they want Branson to have said something bold about risk. It is also the book that least supports the way he is usually quoted — a problem this archive contributed to, having attributed several invented “just do it” passages to it before checking.

What the book actually contains is longer, messier and more interesting: a record of decisions taken against the advice of people who had every reason to be right.

What the book actually argues

Branson’s position on risk is not that fear should be ignored. It is that the regret of not trying is a real cost that most people decline to price:

“I never think that I am going to die by accident, but if I were to die then all I can say is that I was wrong, and the hardened realists who kept their feet on the ground were right. But at least I tried.”

— Richard Branson, Losing My Virginity That sentence is doing something subtler than the bravado it is usually flattened into. He concedes in advance that the cautious people may be correct, and takes the bet anyway on grounds that are explicitly personal rather than commercial.

The appetite is constitutional, not strategic:

“But another part of me is driven to try new adventures, and I still find that I want to push myself to my limits.”

— Richard Branson, Losing My Virginity

The passage that makes the book worth reading

Founder memoirs usually erase the people who disagreed. Branson prints his:

“Simon wasn’t interested in the other projects I talked about and had only ever seen Virgin Atlantic as a huge liability to the rest of the Virgin Group: a business that could be driven to the wall by British Airways or by something out of the blue — something like a war in the Gulf.”

— Richard Branson, Losing My Virginity Simon Draper built Virgin Music with him and had his entire net worth inside it. His objection was not timidity; it was a correct assessment of concentration risk, made by the person carrying it. Branson’s airline nearly did sink the group, and the Gulf War nearly was the thing out of the blue.

Keeping that in the book is the most credible thing in it.

Where to be sceptical

This is the survivor’s account, and it is unusually adventurous. The balloon crossings and the record attempts read as character; they were also, deliberately, marketing that produced enormous free coverage for an airline that could not outspend British Airways. Both things are true, and Branson is more candid about the second than most readers notice.

The philosophy is thinner than the story. Branson’s actual advice, stripped of the anecdotes, amounts to: back yourself, cap the downside, keep moving. The version of it he states most precisely is not in this book at all — it is in Screw It, Let’s Do It: “I take risks, but they are calculated risks. I weigh up the odds in everything I do.”

If you want the philosophy, read that one. If you want to understand how Virgin actually happened — including the parts where it nearly didn’t — read this.

Read it if

  • You want the full arc, including the ventures that failed and the partners who disagreed
  • You are interested in how one brand was stretched across unrelated industries
  • You want Branson at length rather than in aphorisms

Skip it if

  • You want the short version — Screw It, Let's Do It is the same philosophy in a fifth of the pages
  • You want operating detail. Branson narrates deals and adventures, not systems

Read it yourself

Everything above is quoted from the book. If you want the rest of it:

One of these is an affiliate link: if you buy through it we earn a small commission, at no extra cost to you. It does not influence which books are covered here or what is said about them.

Drawn from this calibre

All memos →
Ref. 157 · deep dives

How 4 Billionaires Make Decisions When Nobody Knows What Happens Next

Onward, Grinding It Out, Losing My Virginity, How to Win at the Sport of Business

Power reserve 13 min
Ref. 121 · versus

Phil Knight vs. Richard Branson: Short-Term Drift vs. Taking the First Leap

Shoe Dog: A Memoir by the Creator of Nike, Losing My Virginity

Power reserve 4 min
Ref. 137 · versus

Richard Branson vs. Jeff Bezos: Jump First vs. Regret Nothing

Losing My Virginity, Invent and Wander

Power reserve 4 min
Ref. 235 · versus

Richard Branson vs. Sam Zell: Leap First vs. Look Hard

Losing My Virginity, Am I Being Too Subtle

Power reserve 5 min
Ref. 262 · Single Quotes

Richard Branson’s Simple Rule for a Life Worth Living

Losing My Virginity

Power reserve 2 min
Ref. 84 · deep dives

What Billionaires Really Mean When They Talk About Customer Obsession

Losing My Virginity, What It Takes, Measure What Matters, Principles: Life and Work

Power reserve 11 min
Ref. 25 · deep dives

How 4 Billionaires Make Decisions When Nobody Knows What’s Coming Next

Losing My Virginity, Bloomberg by Bloomberg, Zero to One, What It Takes

Power reserve 12 min
Ref. 22 · versus

Richard Branson vs. Michael Dell: Gut Instinct vs. Data-Driven Decisions

Losing My Virginity, Direct from Dell

Power reserve 5 min
Ref. 55 · Founder Stories

Richard Branson’s Razor-Thin Line Between Empire and Ruin

Losing My Virginity

Power reserve 2 min
Ref. 4 · Contrarian Takes

Richard Branson on Why Business Plans Are Overrated

Losing My Virginity

Power reserve 1 min

The hand behind the calibre

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