Down the Rabbit Hole with Ben Gilbert from Acquired

Some people just see the game. Others see the entire system behind it: the patterns, the hidden forces, the subtle decisions that shape outcomes long before they happen.

Down the Rabbit Hole is a monthly series that explores the thinkers, builders, and creators who see what others miss. These are the people who break things down to their core, uncovering the choices and moments that quietly shape success.

This month, we're going Down the Rabbit Hole with Ben Gilbert to explore how great businesses are really built, the underrated moments that make all the difference, and what we can learn from the best operators in the world.

Ben loves a good story—especially one that reveals how companies grow from simple ideas into something extraordinary. Together with his co-host David Rosenthal, he's built Acquired into a podcast with millions of listeners by taking complex business histories and making them feel like conversations with really smart friends. From his early days as a Microsoft product manager to co-founding Pioneer Square Labs, Ben has always believed that success comes from asking the right questions and digging deep to find meaningful answers.

His work with Acquired shows that behind every great company are countless small, thoughtful decisions that add up over time. Ben has a gift for spotting patterns that others miss and sharing insights that make complex ideas feel somehow achievable. His own journey proves what he's learned from studying hundreds of companies: patient, purposeful exploration leads to lasting results.

Ben Gilbert: Down the Rabbit Hole

Q1: Looking back at all the companies you've studied, what's a seemingly small decision or moment that had surprisingly big consequences?
Ben Gilbert:
This one will probably be obvious to many of your readers, but there's a big one with Microsoft and IBM! In the original deal for DOS, IBM allowed Microsoft to use the OS with other PC makers. There weren't many (yet), but that seemingly small deal term allowed Microsoft to build the entire PC industry around THEM as the standardized platform layer vs. just being a vendor to IBM.

Q2: What's something about successful companies that you never noticed until you started telling their stories?
Ben Gilbert:
The most successful companies took decades of compounding. There is a lot of excitement around new companies with big valuations. And often they are doing something very new and innovative—so rightly so!

However, if a company grows at even 10% in its 20th year, it is often much more meaningful than a company growing at 200% in its 3rd year. In studying companies like Mars, Microsoft, and Starbucks, most of their value typically comes from taking a core insight from the early days and scaling it globally in the far-later years.

Q3: How has studying these companies changed how you approach your own work?
Ben Gilbert:
I have become very aware of just how rare these outlier companies are. As David and I build Acquired, we've been very aware of just how unlikely it is that we become a company like NVIDIA or Hermès, so we're careful about our investments in the business and what you need to believe will be true in order to make them successful.

Q4: What subtle characteristic have you noticed that often signals a founder or company will be particularly interesting to study?
Ben Gilbert:
They are an extreme outlier at something. Most of the founders we study on Acquired are very different—Buffett, Howard Schultz, Bernard Arnault, etc. However, they are all extreme in one way or another.

Q5: Outside of your regular research for Acquired, what's a fascinating rabbit hole you've gone down lately that's captured your attention?
Ben Gilbert:
I bring most of my rabbit holes into Acquired! I became fascinated with the way mechanical watches work (see Rolex episode). And the way that cell phone RF antennas work (see Qualcomm). Or airplanes (see Lockheed Martin). Nice thing about running a two-person business is that you can chase your passions and call it work. :)

Closing Thoughts

The best businesses aren't built overnight; they compound over decades. That's one of the biggest lessons from Acquired and from Ben Gilbert's work: the companies that truly endure take a core insight from their early days and scale it with relentless focus over time.

But success isn't just about having a great idea; it's about execution, timing, and being an extreme outlier at something. Whether it's Microsoft securing a tiny deal clause that changed the PC industry or a founder with an obsessive edge in one area, the small details often determine who rises above the rest.

Ben's approach to breaking down these stories is a reminder that the most valuable insights come from looking deeper at the overlooked moments, the long-term plays, and the decisions that don't seem big until you see their impact years later.

To stay connected with Ben Gilbert's insights on business strategy and company building, tune into the Acquired podcast where he and co-host David Rosenthal break down the playbooks of history's greatest companies. Follow Ben on Twitter @gilbert for his latest thoughts on startups and venture capital, or visit acquired.fm for a complete archive of episodes, detailed research notes, and limited partner content that goes even deeper into the stories behind the world's most impactful businesses.

If you enjoyed this edition, share it with a friend who loves business strategy, great storytelling, or just a good rabbit hole. See you next time.

And as always, thanks for reading,
— Derek
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