Why Startups Fail: 59+ Postmortems of Failed Companies

Why Startups Fail: 59+ Postmortems of Failed Companies

Remember how this company Birchbox was everywhere 3 years ago? And how today it’s…not?

Turns out after raising $90 million at a peak valuation of $500 million, and after a few years of struggle, in 2018 Birchbox sold a majority stake to a hedge fund for only $15 million. This means after a journey of 8 years, its investors were totally wiped out. Employees who had exercised stock options came out with nothing.

Admittedly, I wasn’t a target customer, and this might have been obvious to their user base for years. But that this wasn’t bigger news (at least in the sources I read) reflects an ever-present survivorship bias in entrepreneurship. The companies that survive soak up the attention; the failed companies fade away with a whimper. We forget how much hype they built up years ago, and we turn our attention to the next hot thing.

But failed companies are where some of the best lessons can be learned. Warren Buffett says, “it’s good to learn from your mistakes. It’s better to learn from other people’s mistakes.”

Studying failed companies helps you better differentiate strategies that work from ones that don’t. Studying failed businesses helps you look past platitudes like “culture is everything” to understand the fundamentals of why many businesses fail and some succeed. Studying failed startups helps you discount today’s breathless press hype, and better try to predict the future.

I’ve done a deep dive into 59+ failed startups. Each has a meaningful story to learn from.

  • Most of these were venture funded by big names: Andreessen Horowitz, Sequoia, Kleiner Perkins.
  • They raised on average 8 figures of funding, some with $100 million+ – these were serious contenders, once strongly believed in by professional investors.
  • Many of them have postmortems written by a founder, complemented by third-party analysis of why they failed.

I hope they’re as useful to you as they were to me.

What is the Strategy of the Haven Healthcare Venture? (Amazon-Berkshire-JPMorgan-Gawande)

Earlier this year, Jeff Bezos (Amazon), Warren Buffett (Berkshire Hathaway), and Jamie Dimon (JP Morgan Chase) announced a joint venture to tackle healthcare costs. Recently, they named famed medical writer and surgeon Atul Gawande to be the venture’s first CEO.

Very few details about what the venture is actually doing have been announced, leading some to speculate. The more obvious low-hanging fruits are cutting out middlemen like pharmacy benefit managers (hence Amazon’s acquisition of PillPack) and getting some returns on scale by self-insuring a million employees across the 3 companies.

But I think a lot of speculators are missing the point. I predict ABC Health’s ultimate vision is to create a nationwide insurer that can service an entire nation’s employers and consumers. Much like how 64% of US households are Amazon Prime members, ABC Health hopes to build a payer system that the majority of US households will subscribe to.

Getting to that point is the challenge. Here I’ll describe what I see as the root problems of US healthcare costs, the central strategy that will get ABC Health to massive scale, and the exciting opportunities available to it.

#1 Book Summary: Good to Great, by Jim Collins

#1 Book Summary: Good to Great, by Jim Collins

In Good to Great, former Stanford business professor Jim Collins offers a primer on turning the average into the exceptional. Through detailed case studies of 11 companies that went from tracking the market to exceeding it by at least 3x, Collins presents the key factors that separate merely good organizations from great ones—from rare leadership to disciplined thinking to the dogged pursuit of a core mission. 

Whether you’re an entrepreneur, a manager, or just an individual looking to improve, the concepts in Good to Great provide food for thought—and spurs to action. You’ll learn what it takes to be a “Level 5” leader, why assembling the right team first is more important than having the right idea, why you should be more like a hedgehog than a fox, and why “stop doing” lists are as important as “to do” lists.   

Best Summary + PDF: Extreme Ownership, by Jocko Willink and Leif Babin

Best Summary + PDF: Extreme Ownership, by Jocko Willink and Leif Babin

Jocko Willink and Leif Babin are two Navy SEALS who, among other accomplishments in their service, led teams in the Iraq War. After their experiences in battle, they began applying their leadership principles to business as consultants.

Despite the superficial differences between warfare and business, there are strong parallels in effective leadership in both arenas. Extreme Ownership combines classic management principles with Jocko and Leif’s vivid stories of warfare. In these highest of stakes, common management refrains like “own your results” and “keep it simple” take on a gravitas that make everyday corporate concerns seem like petty squabbles.

In this Extreme Ownership book summary, learn:

  • How to handle failure.
  • How to get other people to listen to you and disarm their resistance
  • What prioritizing the result above all else really means
  • Why you need to take full ownership of everything that occurs in your life

Best Summary + PDF: Blitzscaling, by Reid Hoffman

Best Summary + PDF: Blitzscaling, by Reid Hoffman

Want to know the growth tactics that Uber, Facebook, and Airbnb used to reach massive valuations in record time?

On the other hand, are you confused by companies that bleed billions of dollars and never seem to care about being profitable? “What in the world are they thinking?”

Blitzscaling gives you answers to both. Written by LinkedIn founder and Reid Hoffman, Blitzscaling describes the counterintuitive business strategy of putting efficiency and confidence aside for pure speed.

While nominally a business strategy book, Blitzscaling is generally relevant for:

  • Entrepreneurs who want to build massive companies
  • VCs and investors who want to discover the next big company
  • Employees who want to know how to work in a hyper-growth company
  • Anyone who looks at companies burning money to grow and wants to understand what the heck they’re doing

In this Blitzscaling summary, learn:

  • Common attributes of today’s most successful tech business models
  • When it’s appropriate to blitzscale, and when it will fail
  • The counterintuitive practices of blitzscaling that violate business common sense

Understanding Michael Porter, by Joan Magretta | PDF + Summary

Understanding Michael Porter, by Joan Magretta | PDF + Summary

Michael Porter is considered the father of modern business strategy. One of Harvard Business School’s most famous professors, he originated the ideas of “five forces” industry analysis, the value chain, and competitive advantage.

Like fashion trends, most business ideas come and go. Frameworks are shown to be poorly predictive of success, or apply only to a narrow set of situations. That Porter’s ideas are still widely used in management consulting and taught in MBA programs today, 40 years after introduction, are testament to their enduring utility.

Porter’s seminal works are two tomes, Competitive Strategy and Competitive Advantage, covering 1,000 pages of business strategy. This book, Understanding Michael Porter, is an accessible distillation of the core principles by Joan Magretta (Porter collaborator and former Bain partner).

When I started my first business, Understanding Michael Porter revolutionized my conception of what successful businesses do and what strategy is. It’s not an understatement to say that it gave me an entirely new lens to look at leading businesses and understand how they operate.

In this Understanding Michael Porter summary, learn:

  • Why “aiming to the best” is a stupid business strategy
  • The five forces that tell you how profitable an industry is
  • Why choosing what not to do is as important as what to do
  • How IKEA and Southwest Airlines built master strategies that have endured for decades

Best Summary + PDF: The Smartest Guys in the Room (Enron Book), by Bethany McLean

Best Summary + PDF: The Smartest Guys in the Room (Enron Book), by Bethany McLean

The failure of Enron in the early 2000’s is one of the largest bankruptcies in US history (with Lehman Brothers in 2008 as the largest). Its accounting scandal led to Enron’s bankruptcy as well as the dissolution of Arthur Andersen, one of the big five accounting firms. Shareholders were wiped out, and tens of thousands of employees left with worthless retirement accounts.

Today the name “Enron” still evokes a reflexive repulsion, a feeling that these were simply bad people doing illegal things. But, we think, that’s in the past. Surely we’ve evolved as a society, and by thinking hard enough, you or I can avoid these problems.

In reality, when you dig into the details, Enron’s downfall is the predictable mixture of human greed, poorly structured incentives, and lack of sanity checks when everyone has their fingers in the pie. You might be surprised to learn that most of Enron’s accounting tactics were not technically illegal at the time – they were actually publicly celebrated for being financial innovations. Shareholders, employees, investment bankers, and accountants all benefited from the situation and enabled Enron for years. They only stopped when it became untenable.

The Smartest Guys in the Room, by former Fortune reporter Bethany McLean, is a fantastic recounting of the rise and fall of Enron. It shows how, layer by layer, the fragile house was constructed until it became impossible to sustain.

In smaller ways, we too are subject to the same pulls as Enron managers and employees. The warning – if we were put into the same situation, we might not have behaved any differently.

In this Smartest Guys in the Room summary, learn:

  • The key conditions that enabled Enron’s corruption and allowed stakeholders to look the other way
  • The financial maneuvers that allowed Enron to disguise its fundamental financials
  • Practices to avoid in your own life

Best Summary + PDF: How to Win Friends and Influence People, by Dale Carnegie

Best Summary + PDF: How to Win Friends and Influence People, by Dale Carnegie

How to Win Friends and Influence People by Dale Carnegie is a classic that needs little introduction. It’s one of the best-selling books of all time and a major developer of the “self-help” book genre. Many principles written in How to Win Friends and Influence People have been repackaged and articulated in different forms.

Published 80 years ago, it contains universal principles of interacting with other people that ring true even today. Since its publishing, much has changed about the way we access information, work, and communicate – but little has changed about human nature and what we crave from other people.

In this How to Win Friends and Influence People book summary, learn:

  • How to be a great conversationalist while saying barely anything
  • What people crave from others as much as food or water
  • Why you fish with worms, not cheesecake, and what this means for people interaction
  • How to influence people to see your way of thinking, without arousing their anger

Porter’s Five Forces, Explained w/ Examples

Porter’s Five Forces, Explained w/ Examples

Michael Porter’s Five Forces Model explains the always important question: Why are some industries consistently more profitable than others? When examining industries, it’s tempting to focus on the competition between rivals. But rivals are also engaged in a struggle for profits with all the other players in the ecosystem – like customers, who would always like to pay less and get more.

Best Summary + PDF: Originals, by Adam Grant

Best Summary + PDF: Originals, by Adam Grant

In our modern economy, innovation is prized socially and rewarded financially. But how do you generate good new ideas? How do you tell which ideas are good? And how do you execute to make them real?

Wharton professor Adam Grant addresses these questions in Originals: How Non-Conformists Move the World. A bestseller like his first book Give and Take, Originals studies the habits of highly original professionals and dispels myths related to originality.

If you’re trying to be innovative, noted originals like Elon Musk and Steve Jobs may be intimidating. They seem like unique forces of nature, born with incredible intellect, creativity, and willpower, while we mere mortals are doomed to follow.

If there’s one message Adam Grant wants to convey in Originals, it’s to dispel this apparent misconception – you too can be original.

In this Originals book summary, learn:

  • The primary factor in generating more good ideas
  • Why “first mover advantage” is a myth
  • How procrastination can actually help you come up with better ideas
  • Why first-born children are generally less creative than last-born children, and how to encourage originality in your children
  • Which levels of an organization’s totem pole to target with your new idea