I know many people love business and investing podcasts. I am not one of them. I tried a bunch, especially during COVID, but none held my attention for more than a week or two. If you told me two years ago that I would be hooked on a podcast that features the complete history of a single company with episodes that typically run 3-4 hours, I would not have believed you. As it turns out, I find the stories so captivating that I often replay an episode three or four times!
I began listening to the Acquired Podcast in May 11, 2024, the day after it was featured in the Wall Street Journal. The WSJ article began as follows:
“It’s a wonky podcast about business history and strategy with four-hour episodes that drop once a month. And people from Silicon Valley to Wall Street are completely obsessed with it.
Acquired is the unlikely hit show hosted by Ben Gilbert and David Rosenthal, whose ability to understand companies deeply enough to describe them simply makes listeners want to spend time with them. Lots and lots of time.
By turning case studies into cinematic spectacles, they have built the business world’s favorite podcast.”
Obviously, I was not an early adopter. The show had already been building steam for eight years before I learned of its existence. The WSJ article made me feel like I was missing out on something important. Still, what inspired me to give it a listen was that I read the article in Logan Airport just as I was facing a three-hour drive to my mom’s house in Vermont. I queued up the most recent episode on Spotify, which was Season 14, Episode 3: The Complete History and Strategy of Renaissance Technologies… The best performing investment firm of all time. I was so enthralled that I kept driving beyond my mom’s house so I could finish the episode. I have since replayed the Ren-Tech Episode three more times.
Over the past two years, I have logged hundreds of hours listening to dozens of other similarly riveting Acquired podcasts. The purpose of this essay is to offer up some of the insights and common themes I have gleaned from listening to Ben and David tell the origin stories of great companies and the people who created them in a way that is every bit as captivating as epic movie. Links to many of the episodes are included.
Insight #1: The Role of serendipity in the creation of great companies cannot be understated.
It is remarkable how many of today’s most iconic businesses owe their very existence to at least one major stroke of luck. For instance, in the Novo Nordisk episode, we learn how the GLP-1 hormone was largely abandoned as a treatment for diabetes and would have been relegated to the research scrap heap were it not for a single researcher, Lotte Knudsen, who saw a glimmer of hope. After years of research with little to show for it, her project was on the verge of being terminated at the time of the breakthrough that led to Ozempic and Wegovy.
Starbucks founder Howard Schultz owes his legendary career at Starbucks to a chance encounter at a pick-up basketball game. After the game, Howard was sharing his profound distress with a teammate over learning that one of the investors he recruited to help him attain his dream of buying Starbucks had betrayed him and was preparing to buy the business for himself. The player was a young lawyer who introduced Howard the next day to the name parter at his law firm, Bill Gates Sr. (father of Microsoft founder, Bill Gates, Jr.). Gates Sr. was a highly respected corporate lawyer in Seattle. He listened to Howard’s story and stepped in to block the rogue investor and provide Howard with the remaining funding he needed to buy Starbucks from its original founder.
Larry Page and Sergey Brin tried in vain to sell their PageRank algorithm to dominant dotcom era search engine AltaVista for $1 million in 1998 so they could resume their studies at Stanford. In 2002, Yahoo! offered $3 billion for Google, but walked away when Page and Brin countered with $5 billion. How different would the world be if either of those transactions came to fruition?
Insight #2 Many of the greatest companies today faced at least one existential threat in their history.
Many have nearly been exterminated more than once. Amazon came perilously close bankruptcy in the early 2000s and survived because of a $1.25 billion convertible bond offering the company issued in 1999 not because they needed the money but because credit was irresistibly cheap. The dotcom bubble burst about a month after the offering and the funds allowed Amazon to continue to expand and invest in fulfillment centers while companies around them perished.
Nvidia faced the possibility of failure and/or obsolescence four times in its history. As CEO Jensen Huang notes in his 2023 Acquired interview, there are many companies that did everything right and still failed and there are many companies that made many mistakes and succeeded because they got a few lucky breaks along the way.
Insight #3 Investors should not beat themselves up over not spotting the opportunities in great companies early.
Often the founders of the companies featured in Acquired did not recognize the profit potential of their businesses either! The poster child for this is Google. After investing $100,000,000 in Google’s Series A funding round, John Doerr of Kleiner Perkins purportedly told Michael Moritz of Sequioa Capital, “We’ve never paid so much for so little.” At the time, google had 25 employees, an incredibly popular search tool, but no revenue or even a business model. For their part, founders Larry Page and Sergey Brin proposed a number of quirky business models that floundered miserably. In fact, in the early years, the only monetization strategy that they adamantly opposed and resisted was paid search! [Google: The Origin of Search]
Similarly, NVIDIA’s market share in the gaming chip space plateaued in the 2000s. The company faced an uncertain future, when CEO Jensen Huang hypothesized that there might be a future market for accelerated computing in scientific and medical testing applications. At the time, many, including Jensen himself, were skeptical of the revenue potential from that niche space, and for a few years demand for these machine learning chips (GPUs) was negligible. In 2012, a viral article published by three academic researchers who had used NVDIA chips to win an image recognition competition raised awareness of the limitless potential of machine learning and large language models. The “AlexNet” paper provided the tinder that sparked a seemingly limitless demand for NVIDIA’s GPUs and stands out a remarkable example of pluck and luck. [NVIDIA: The Machine Learning Company]
Insight #4 No moat is infinitely wide.
Warren Buffett and Charlie Munger were fond of companies with wide moats and unassailable brands. However, an important observation I gleaned from Acquired is that no company is immune from competition forever. Microsoft entered into a years-long battle with the Department of Justice over its operating system monopoly. By the time the lawsuit was settled, Microsoft was fighting for relevance as Internet search and mobile replaced the Windows desktop as the center of consumers’ digital experiences. Similarly, Alphabet’s unrivaled position in search through its Chrome browser has been the target of anti-trust litigation by the DOJ for several years. In 2025, the DOJ prevailed in its claim that Google has a monopoly in search but scaled back its legal remedies in part out of recognition that Google’s search is suddenly facing an existential threat from AI search. How quickly things change. [Google The AI Company]
Insight #5 The “Adult supervision” paradigm seems like a success killer.
The venture capital playbook calls for the original founders to ride off into the sunset so that the older, more experienced corporate executives can step in to manage the company’s growth as a public company. Yet virtually all of the most successful companies today are the ones with visionary founders who resisted or rejected the VC-led board’s attempts to push them aside.
Would Apple have become the Apple we know today, if Steve Jobs cashed out at the IPO? In Apple’s case we have a partial answer. Apple’s Board wanted “adult supervision” as Apple scaled. In 1985, the Board brought in Pepsi marketing executive John Scully to serve as Co-CEO with the 28 year-old Jobs. Scully forced Jobs out within a few years. Scully, in turn, was fired the Board in 1993. Jobs was brought back to lead the Apple again in 1997 via the acquisition of Jobs’ subsequent company NExT Software. It is difficult to imagine that the success trajectory would have been the same at Facebook/Meta without Mark Zuckerberg, Amazon without Jeff Bezos, Google/Alphabet without Larry and Sergey, or Tesla without Elon.
That said, Acquired has also chronicled companies in which leadership change was necessary to save the company. Uber’s Board stepping in to remove founder Travis Kalanik and replacing him with Dara Khosrowshahi is a sterling example.
#6 Build It and They Will Come is a Terrible Model for Creating a Business…Except When It Works!
A guiding principle in the VC start-up space is, “If you cannot demonstrate product market fit, you should quit.” Yet the afore-referenced list of the most successful tech startups today is comprised of several companies that created a new business or industry out of thin air. Tesla stands out as an obvious example. Today Tesla’s market capitalization is greater than the rest of the world’s auto industry combined. As mentioned earlier, NVIDIA created its GPUs years before the market for them was recognized. People did not know they needed the iPhone until Apple invented it and showed consumers they can barely survive without one. The Taiwanese government apparently did not get the VC memo either when it tasked Morris Chang with creating the world’s first dedicated semi-conductor foundry from scratch in 1987 when there was absolutely no demand for that service. [The Complete History and Strategy of TSMC]
#7 It is Difficult to Capture Lighting in a Bottle Twice.
Most world-changing companies find it difficult to reinvent themselves or to replicate the success of their original business. For example, Microsoft dominated the PC market, but completely whiffed on search, mobile, and social media, even though the company recognized the importance of the trends as they emerged. Ironically, Microsoft found its way into its second era of dominance as a software company when it focused on collaboration and integration in the cloud and enterprise space. Current CEO Satya Nadella was driver of that push. [Microsoft Volume II]
Amazon’s creation of AWS as an entirely separate business is another example. Although Amazon is opaque in reporting the amount of earnings generated from AWS, it s believed to generate as much as 75% of Amazon’s operating income.
However, the company that will likely go down in history as the greatest business creator of all time is Alphabet. As Ben and David pointed out the third episode their Google/Alphabet Trilogy – Google the AI Company Fall 2025 Episode 1 (4:06:37), search is recognized as the crown jewel of the company, but Alphabet has a cadre of other businesses that, if spun off on their own, would each potentially command market caps of $500 billion or more as well. Those businesses include YouTube, Google Cloud, Waymo, Deep Mind, Android, and Gemini.
Other Acquired Takeaways
One universal observation from Acquired is that the raw intellect of the founders of most of the companies that are featured is off the charts. To get a sense of this I recommend the interviews with Jensen Huang and Jamie Dimon. It is also clear from the conversation that Ben and David are on the same intellectual level. Listening in on these conversations is extremely humbling.
Another near universal quality of the founders of these great companies is that they are not just brilliant minds, they are charismatic and unafraid of taking massive risks. Listening to the Tesla and Space X podcasts, I was blown away by how Elon repeatedly bet more than everything he had to will Tesla and Space X into existence. As Jensen said in his interview, betting it all isn’t risky if you know you are right.
The best way to summarize the value of Acquired is that it helps you to understand the way the world around you works. I can attest that it has made me more knowledgeable, it has made be a better financial planner, and it has influenced how I plan for Financial Planning Hawaii’s present and future. It may surprise readers to learn that the most directly impactful episodes for my business were Costco and Hermes. I almost did not listen to the Hermes episode because I had zero interest in luxury handbags, but the principles for how this company built and scaled a family business that has lasted nearly 250 years are directly applicable to the “high-touch,”multi-generational business I am trying to build.
Below are some of my favorite episodes that were not included in this essay. LVMH, Visa, Bitcoin, Ethereum, Alphabet, Steve Ballmer, Meta, Mark Zuckerberg, Microsoft Volume 1, Lockheed Martin, Qualcomm, Benchmark, AWS, Nvidia – The GPU Company 1993-2006, Taylor Swift, Sequoia.
