The market you choose sets the ceiling on everything you build. Pick a small one and you work twice as hard for half the return. Pick the one about to go to the moon, before the crowd arrives, and the payoff lasts decades. Tom Siebel has done that three times in a row, and he says it is something you can learn.

Siebel was an executive at Oracle through the 1980s, then founded Siebel Systems, which created the customer relationship management market before Oracle bought it for $5.8 billion. In 2009 he founded C3 AI , the enterprise artificial intelligence company he led until 2025 before standing down and returning in May 2026 . Forbes puts Siebel’s net worth at around four billion dollars.

Siebel found each of those markets before the rest of the world saw them coming. People call that vision. He’s not convinced. "We were just students of history. We looked at what happened in the past, and we were able to project it out into the future. And we've gotten lucky now three times." But I'm not convinced it's all luck. Here is how he does it.

Tom Siebel predicts the future: the method behind his billion-dollar bets

Read history and look for the rhyme

It starts with reading. Siebel studied history at university and never stopped learning, treating the past as the best data on the future. "History may not repeat itself, but it sure seems to rhyme." Every market he has entered ran a pattern he had seen before, so he recognised it while others called it brand new.

Build the same habit. Read how earlier industries grew, broke apart, and reformed, then look for the rhyme in your space. The forces that decided the database market or the cellphone market are deciding yours now. See the pattern early and you stop reacting to the news and start getting ahead of it.

Find the prediction the crowd is ignoring

As a student, Siebel found the book, The Coming Post-Industrial Society, by sociologist Daniel Bell, who argued that information technology would remake the global economy on the scale of the Industrial Revolution. He believed it. "And I thought, boy, that's a game I'd like to get involved in." Siebel enrolled in engineering, learned relational database theory, and walked into Oracle already an expert in the technology the world was about to need.

Find the forecast almost nobody is acting on, then act on it. And while forecasting could be a learnable skill, being able to predict how something will unfold requires vision. Siebel believes the prediction is usually found in information anyone can access, a book, a paper, or an overlooked corner of your industry, waiting for someone to take it seriously enough to build on. Be that person before the obvious arrives. Just like he did.

Enter the part of the market no one has touched

Siebel’s next move came from the gap others walked past. At Oracle, accounting, HR, and manufacturing were already being automated, while three huge functions sat wide open. "The fields of sales, marketing, and customer service remained largely untouched by information technology. And I believed there was no chance they were going to remain untouched. So I left Oracle to start Siebel Systems." The result was a category he owned. "And at Siebel, we invented the CRM market."

He ran the same play with artificial intelligence. "We were talking about enterprise AI in 2011, 12, 13, 14, 15, and honestly, we might have been the only people in the world talking about enterprise AI." The rest of the world arrived in late 2022. Look at your market for the function everyone calls too hard, too dull, or too early, and go there first. The open space is where you set the rules. The crowded one only lets you fight for scraps.

Build to win, because only the leader survives

Picking the right market is half of it. Siebel learned the other half working with Larry Ellison at Oracle, where the goal was always to lead. "Larry Ellison always went after a market leadership position, which implied 50% market share." Behind that target sits mathematics. "Only about four companies survive in every segment. One company ends up with about 50% share, and that company continues to generate cash. Number two probably has 15% share, number three has 10%, and the rest have fractional shares."

That math decides who lives through the next crash. When a downturn hits, hundreds of companies fold and the leader is the one left standing.

Even if you're running a small business, shoot for the moon. Why wouldn't you? If you think about solving small problems, you get small solutions that leave you playing a game below your potential. If you think about how you can become the market leader, you make a different set of decisions. No one gingerly broke a world record or tentatively became a billionaire. Extreme people get extreme results. For maximum results, go all in.

Learn or build a high tolerance for pain

None of this works without the capacity to endure. "It might be that I have a very high tolerance for pain. I really do." Siebel has earned the right to say it. "If you look at some of the things I've encountered in my life, like being attacked and mauled by an elephant, and going blind in 2025, I've dealt with a lot of pain physically. I think I'm able to deal with a lot of pain emotionally too. And I suspect great entrepreneurs are able to do that."

Pain looks different to different people, and the founders who outlast everyone keep moving through it. "You're down, you're out, you're done, you've been knocked out, you're prostrate on the ground. And for some reason, every time, I'm able to get up on an elbow, get up on the other elbow, grab a knee, stand up, put one foot in front of the other, and then repeat, and keep going." You can build that capacity before you need it. Choose hard things on purpose, so that when the real test arrives, getting back up is already a habit.

What the Tom Siebel method means for founders now

Siebel keeps finding billion-dollar markets, and says the tools to act on it have never been more available. He calls the current moment a great leveller, where one person holds power that used to belong to institutions. "I have access to computing resources and computational capability that was only available to a national laboratory last year." The skill that unlocks it is simpler than expected. "It is prompt engineering. And that prompt engineering is available to all of us."

Read the history, find the prediction, enter the open market, build to lead, and learn to take the pain, then point the most powerful tools ever built at the biggest market you can find.

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