Losing My Virginity: How I Survived, Had Fun, and Made a Fortune Doing Business My Way

Overview

Richard Branson’s 1998 autobiography charts the arc from a dyslexic, headstrong schoolboy to a swashbuckling entrepreneur who made Virgin into a global brand. Told in a brisk, anecdotal voice, it interweaves close calls, audacious gambles, and hard lessons with an almost evangelical belief that business can be exhilarating, humane, and irreverent. The narrative doubles as a chronicle of late 20th‑century business disruption, showing how a challenger mentality can unsettle complacent incumbents across music, aviation, retail, and beyond.

Early Sparks

Branson frames his childhood as training in self-reliance and optimism. Struggling with traditional schooling and dyslexia, he discovers energy and purpose in making things happen. Leaving Stowe School at sixteen, he launches Student, a youth culture and politics magazine, hustling ads and interviews with famous names to keep it afloat. The magazine’s mailroom becomes a crucible for the next venture: a discounted mail-order record business that taps into the countercultural mood and a generation’s hunger for access and value.

Building Virgin

Virgin evolves from a mail-order outlet to a record shop, then to a recording studio in the English countryside and a label willing to back unlikely talent. Branson stakes the company on Mike Oldfield’s “Tubular Bells, ” which becomes a phenomenon and funds further bets. The label embraces artists other companies fear, punks, misfits, and unconventional voices, most famously the Sex Pistols, whose notoriety fuels Virgin’s outsider mystique. Cash-flow crises and bank pressures recur, and Branson’s approach is to improvise boldly, renegotiate relentlessly, and keep the brand playful and public-facing. As Virgin expands into retail megastores and other categories, Branson articulates a simple rule: enter markets where customer experience is stale, strip away nonsense, and delight people.

Taking on the Skies

The book’s centerpiece is the birth of Virgin Atlantic. Frustrated by poor service, Branson leases a single secondhand plane and promises a friendlier, more glamorous transatlantic experience. He courts press with stunts, but obsesses over details, seatback entertainment, attentive crews, and unexpected touches, turning service into story. The ensuing rivalry with British Airways becomes a corporate morality play. Branson recounts BA’s alleged “dirty tricks” campaign, the bruising legal battle that follows, and Virgin’s vindication, with damages shared among staff. To keep the airline alive during a recession, he makes the wrenching decision to sell Virgin Records, a tearful moment that underscores his readiness to sacrifice what he loves to protect the larger mission.

Risk, Resilience, and Reinvention

The memoir pulses with near-disasters. Branson’s speedboat bids for the Atlantic record end in a sinking and then a triumph; balloon crossings push the edge of survivability and publicity alike. These adventures mirror his business ethos: take calculated risks, prepare obsessively, learn fast when things go wrong, and keep morale high. The Virgin portfolio sprawls, trains, mobile, cola, financial services, and while not every bet lands, the brand’s cheeky challenger spirit and customer empathy become durable assets. Setbacks, from cash crunches to regulatory battles, are framed as fuel for ingenuity rather than reasons to retreat.

People, Principles, and Private Life

Branson credits momentum to a culture of trust and delegation. He hires for spark and attitude, hands people responsibility early, and treats mistakes as tuition. He emphasizes fairness, fun, and a bias to action, “Screw it, let’s do it”, arguing that reputation compounds like capital. Away from boardrooms, he writes about love and family, buying and restoring Necker Island, marrying Joan Templeman, and raising Holly and Sam. The personal and professional blur; hospitality on the island becomes a sandbox for ideas and a refuge after bruising fights.

What Endures

By the end, the story reads as a manifesto for entrepreneurial audacity: challenge orthodoxy, obsess over customers, market with mischief, and rally people around a shared adventure. The candor about fear, failure, and luck keeps the triumphs grounded, while the title winks at a deeper point, Virgin’s value was never naivety, but the nerve to keep starting again.