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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.
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—— ON THIS DAY ——
MAY 28, 1588
Lisbon, Kingdom of Portugal (under Spanish control)
437 years ago
The Spanish Armada — a contemporary painting depicting Philip II's fleet, the largest naval force assembled in Europe since antiquity, which set sail in May 1588 to invade Protestant England.
On May 28, 1588, the Spanish Armada — 130 ships carrying approximately 30,000 men, the largest fleet assembled in European history — departed Lisbon under the command of the Duke of Medina Sidonia. Philip II of Spain had spent years and an estimated ten million ducats on the enterprise. Its objective was to escort an army of 17,000 soldiers under the Duke of Parma from the Spanish Netherlands to England, overthrow the Protestant Queen Elizabeth I, and restore Catholic rule to the island.
The plan failed on multiple levels, in multiple places, for multiple reasons. The Armada's coordination with Parma's army was never achieved — they could not communicate reliably, and the shallow waters of the Dutch coast prevented the large Spanish galleons from approaching closely enough to embark the troops. The English fleet, under Lord Howard of Effingham and Francis Drake, harassed the Armada relentlessly up the Channel without engaging in a decisive battle. Then, on August 7, the English launched fireships into the anchored Spanish fleet at Calais, scattering it in panic. And then the weather did the rest.
—— MARQUEE EVENT ——
Sir Francis Drake — English privateer and naval commander, whose aggressive harassment of the Armada in the English Channel contributed to its failure to land troops in England.
The famous phrase 'God blew, and they were scattered' — inscribed on the commemorative medal that Elizabeth I struck to mark the victory — captured the Protestant interpretation of the defeat: it was a divine judgment. The storms that drove the scattered Armada around the north of Scotland and down the west coast of Ireland were catastrophic. Ships that had survived the Channel fighting were wrecked on Irish rocks. Of the 130 ships that had sailed from Lisbon, approximately 67 returned to Spain. Of the 30,000 men, approximately 10,000 survived.
Elizabeth I's response to the crisis demonstrated the political skill that defined her reign. When it was uncertain whether the Armada would break through and Parma's army would land, she traveled to Tilbury in Essex to address the assembled English forces in person. The speech she gave there — 'I know I have the body of a weak and feeble woman, but I have the heart and stomach of a king, and of a king of England too' — became one of the most celebrated in English history, whether or not the exact words are correctly attributed.
The Armada's defeat did not end the Anglo-Spanish war, which continued until 1604. Nor did it end Spanish sea power — Spain remained a dominant naval power for decades after 1588. What it did do was demonstrate that the Spanish monarchy was not invincible, encourage Dutch resistance to Spanish rule, and establish England as a naval power that could project force beyond its own waters. The defeat of the Armada is the founding myth of English sea power — and, by extension, of the British Empire.
—— WHY THIS MATTERS ——
The Armada's failure preserved Protestant England and enabled the development of English imperial power. A Catholic victory in 1588 would have ended the Elizabethan era and potentially the English Reformation. The course of colonization, commerce, and cultural development would have been entirely different. The United States, as an English-speaking Protestant nation, is a remote but real consequence of the Armada's defeat.
The defeat demonstrated the limits of the 'irresistible force' theory of military power. The Armada was the largest fleet ever assembled; it was defeated by a combination of defensive harassment, tactical innovation (the fireships), and weather. The lesson — that size alone does not determine military outcomes — has been learned and forgotten by commanders in every subsequent century.
The Irish dimension of the Armada story is often forgotten. Approximately 5,000 Spanish sailors and soldiers were wrecked on Irish coasts. Their treatment varied dramatically: some were helped by the Irish population and survived; others were massacred by English forces or local lords. The Armada wrecks on the Irish coast are some of the best-preserved maritime archaeological sites in Europe.
—— THE TAKEAWAY ——
On May 28, 1588, the most powerful navy in the world set sail to overthrow the most famous woman in Europe. It was defeated by English tactics, Dutch geography, Irish weather, and a fire set in darkness at Calais. The empire that might have followed a Spanish victory was instead built by England.
—— QUOTE OF THE DAY ——
"I know I have the body of a weak and feeble woman, but I have the heart and stomach of a king, and of a king of England too."
— Queen Elizabeth I, speech to the troops at Tilbury, August 1588, as the Armada threatened
—— OUR QUIZ OF THE DAY ——
How much do you know about the Spanish Armada, Philip II's ambitions, the English tactics that scattered the fleet, and the storms that finished what English cannons had begun?
