Published: August 29, 2025
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In 1980, Steve Ballmer started as Bill Gates' assistant with a $50k salary. Today, he's worth ~$150B — more than Gates himself. Here's his incredible story (and what we can learn from the richest employee who ever lived) 🧵

Image in tweet by Brett Trembly

In 1980, Ballmer left Stanford Business School to join Microsoft as employee #30. Gates offered him $50,000 plus 10% of profit growth. But within a year, that deal became too expensive for Microsoft. So Ballmer made arguably one of the smartest trades in business history.

He swapped his profit-share for ~8% equity. Gates actually reduced his own stake to make room for Ballmer's shares - he needed someone he trusted to handle the business side while he focused on code. So while Gates built the tech, Ballmer built the machine:

He led sales teams, operations, and played a huge role in shaping Microsoft's rise from a scrappy startup into a business empire. By 1992, he was Executive Vice President of Sales & Support. By 1998, he was President. And in 2000, Gates stepped down as CEO...

And Ballmer stepped in. He ran Microsoft for 14 years as CEO. During his tenure: • Launched Xbox gaming console • Acquired Skype for $8.5 billion • Launched Bing search engine Ballmer stepped down in 2014 and his Microsoft stake was worth $12-15 billion.

He famously stated: "I'd like to own Microsoft shares until I either give something to charity or I die." Turned out to be a smart decision. Under CEO Satya Nadella, Microsoft's value exploded with cloud computing and AI.

Today, Ballmer's net worth is ~$150 billion. Which, thanks to Bill Gates’ recent net worth re-evaluation after his philanthropic donations, is now higher than his former boss’s. Pretty wild. He's the only centibillionaire who made his fortune as an employee, not a founder.

What I find interesting about this story: We often think of delegation as just "offloading tasks," and of our assistants as "admin people." But being someone's assistant can actually put them in the right room + give them skills they can't get anywhere else.

Ballmer got a front-row seat to every major decision at Microsoft for decades. He learned how Gates thought, how he made decisions, etc. And that lived experience was worth *way* more than the MBA he was initially pursuing.

Image in tweet by Brett Trembly

I love delegation because it works both ways. You get your time back - the most valuable resource you have as an entrepreneur. They get real experience + a chance to grow. Plus, you never know - the people you invest in now might just invest in you later.

PS: I run an offshore staffing company for U.S. law firms. After growing @getstaffedup1 to $25M, I'm launching a beta program for entrepreneurs who wants to get into staffing. DM me if you're interested in testing it.

This is the part where I'm cheeky and ask you to follow me... @btrembly - I share legal thoughts, breakdowns, and lessons I've learned growing my law firm & staffing company. Like/Repost the quote below to share with a friend:

@btrembly He is the most successful total douchbag in the history of the world.

@btrembly It's crazy how going from Gates' assistant on a $50k salary turned into billions; timing and hustle matter

@btrembly has he ever sold shares? or just lived off salary and dividends?

@btrembly Gates worth way more really

Image in tweet by Brett Trembly
Image in tweet by Brett Trembly

Thinking of reactivating last year’s BFCM campaigns? @triplewhale analyzed 10,000+ ad accounts, and the data from the first half of 2025 makes one thing clear: the old BFCM playbook is dead. Ad spend is up 27.24%, while CPA climbed 11.70% and CPM rose 14.84%. The percent of

Image in tweet by Brett Trembly

In 1985, Costco's founder nearly killed his partner over a hot dog. That fight turned a struggling retailer into a $250B empire and turned shoppers into fanatics. The entire food industry was stunned. Here's the untold story of the $1.50 hot dog that almost broke Costco:

Image in tweet by Brett Trembly

Most people overthink— Successful people just start: If you keep waiting for the “perfect idea,” you’ll still be waiting next year. Because the perfect idea doesn’t show up when you sit still. It shows up when you take action. You don’t need 100 ideas. You need 1 that’s

Image in tweet by Brett Trembly

Cars have almost completely changed since they were invented in 1886. We went from hand cranks to electric engines, from no safety features to 10 airbags. But there's one thing that hasn't changed and probably never will... Here's the feature that's stumping engineers:

Image in tweet by Brett Trembly
Image in tweet by Brett Trembly

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