Multiple business choices may have hindered Sears’ financial success

Former Sears CEO and hedge fund manager Eddie Lampert was a reclusive billionaire who was once kidnapped from his home in Greenwich, Connecticut by criminals looking to get rich.

Sears failed to evolve in a changing economy

At its peak, Sears was the largest retailer in the world, making elite objects accessible to the middle class. But in 2018, the company officially filed for bankruptcy due to massive debt and losses.

Sears filed for Chapter 11 bankruptcy in 2018

Although the retailer may have failed financially speaking, some argue that longevity in itself is a success—the brand operated for over 130 years before that bankruptcy filing, after all.

Inside one of the last Sears stores in the US

Sears was once one of the most successful businesses in the US. Today, there aren’t many Sears stores left in the nation, and the ones that are still around feel more like ghost towns than meccas of retail history.

Explore a Sears historical timeline

Sears has existed for over 130 years, and is remembered for much more than its 2018 bankruptcy, from the Sears and Roebuck’s catalog to Discover Card and Allstate Insurance.

See America's top companies by revenue in 1994 versus 2023—Sears isn't on the 2023 list, while Amazon isn't in the 1994 edition.

Sears once tried to become a tech company

In 1984, Sears arguably created one of the first online retail services, called “Prodigy,” in 1984 alongside IBM and CBS. But it was more of a WeChat than an Amazon, offering a variety of other services to users a few years before the dot com era.

Claire's has filed for bankruptcy multiple times

Between competition from online retailers such as Shein and Temu, and too many physical stores for today's retail climate, Claire's has had a difficult time modernizing.

The Sears catalog sold some weird products before it folded, including drugs

At various times in its existence, the Sears catalog sold everything from heroin to tombstones. But by the 2000s, the catalog was no longer in publication.

Macy’s announced a series of pandemic-era store closures in January 2021

Specifically, as mall foot traffic declined, Macy’s sought to grow elsewhere (as did many other retailers around the same time).

Bezos has frequently cited a 1999 article titled Amazon.bomb to illustrate how dire the early predictions about Amazon got

Over the years, Amazon founder Jeff Bezos often recalls how wrong the predictions in the 1999 Barron’s cover story were. Among other things, that article declared Amazon’s entire business model to be unsustainable and destined to fail, noting its lack of profit and dependence on a massive amount of capital to fund its growth.

A private equity firm led the leveraged buyout of Toys 'R' Us before the company's bankruptcy

After being acquired by two private equity firms and a real estate company for more than $6B in 2005, Toys 'R' Us filed for bankruptcy in 2017. Many point to the $400M a year the company had to pay to service its debt, as well as increased competition from online retailers like Amazon, for draining its profits and ultimately dragging it under.

Scroll through a Sears historical timeline, starting in the year 1886

The Sears story starts with railroad worker Richard Sears purchasing a declined shipment of watches for a discounted price. An interactive historical timeline chronicles the history of Sears from then onwards.

How Sears helped create Discover Card

Sears owned the financial services company Dean Witter, which rolled out the Discover Card in 1986. The Discover Card is just one of many Sears inventions that seems to have outlasted Sears’ peak popularity, including Allstate Insurance and the clothing brand Lands End.

As of 2024, Macy’s wanted to monetize its store closures through real estate deals

In a 2024 earnings call, Macy’s noted that while it’s remodeling and investing in some of its brick-and-mortar locations, it seeks to shutter other stores in lower-performing locations. It’s estimated that Macy's will close 150 locations through 2026.

Some argue the Sears catalog undermined Jim Crow laws in the rural South

When the Sears catalog was popularized, Black Americans didn’t always have an easy time shopping in US stores due to racism and Jim Crow laws. Some say that the Sears catalog was radical at the time for helping Black Americans avoid retail shopping in the South—often a negative experience.

In 2006, Macy's was worth $20B—but as of 2024, its market cap was just under $5B

Macy's went from roughly 800 to 500 stores within the same time period. Macy’s has spent the recent years since the pandemic closing swaths of stores.

Sears used to sell entire DIY houses in its catalog

From 1908 through the 1940s, Sears sold DIY house kits starting at $600. An estimated 100,000 homes were built, but fewer than 5,000 have been identified today.

See which companies folded and which survived the dot-com crash

Companies that primarily used the web as a platform for doing business were more vulnerable than companies that created technology. While hardware and software companies managed to make it to the other side, most e-commerce companies took a brutal beating and share prices plummeted.

Amazon didn't have a profitable quarter until 2001, more than 6 years into its existence

Jeff Bezos, however, took pride in Amazon's early unprofitability, reinvesting the money Amazon made back into its business, prioritizing investment into long-term growth and customer acquisition over short-term gains.

Amazon expanded its business and diversified its offerings by acquiring companies

Amazon’s retail and cloud businesses have been key drivers of the company’s growth over the years, but they haven’t done all the work by themselves. Companies Amazon has acquired include the video doorbell maker Ring, the grocer Whole Foods, the streaming service Twitch, the shoe retailer Zappos, and the film studio MGM.

In 1994, Amazon was founded as an online bookseller

Books were just the start, as founder Jeff Bezos' ultimate goal was to create an "everything store," using the internet to transcend the physical limitations of brick-and-mortar retail. The Seattle-based Amazon gradually added CDs and consumer electronics, becoming a dominant e-commerce player in the late 1990s, and one of the few dot-com companies to make it through the bust.

Amazon's success is attributable, in large part, to founder Jeff Bezos’ vision

Bezos parlayed a career on Wall Street into founding an online bookstore that would evolve into the largest online retailer in the world. Bezos’ story is characterized by his relentless focus on innovation and on the customer experience at Amazon.

Red Lobster lost $11M on endless shrimp promotions—but its real estate holdings were what dragged it to bankruptcy

Golden Gate Capital, a PE firm, bought Red Lobster in 2014 for $2.1B. Golden Gate then sold Red Lobster's real estate, more than 500 storefronts, which generated $1.5B in revenue and helped finance the PE firm's acquisition of the company. Analysts say increased debt, high rent costs, and low equity put Red Lobster in an impossible position, leading to its 2024 bankruptcy filing—although the shrimp bill probably didn't help.

Just because a big name company is going public doesn’t guarantee a successful stock

A reporter dove into how highly anticipated IPOs can still be risky, and why retail investors should be wary of investing right away.

Why private credit has faced challenges in recent years

The factors that some experts say are driving what could be private credit's most challenging era since the 2008 financial crisis include global economic uncertainty around trade and tariffs, investor fears about the amount of money being spent on artificial intelligence, and more.

A deep dive into Enron, one of the largest accounting scandals in history

Investing comes with great opportunities for reward, but it also carries great risk. Investors learned that the hard way when Enron collapsed. Everyone lost money—from the largest institutions on Wall Street to mom-and-pop investors who bought S&P 500 index funds. This series from American Scandal starts with a close-up into an investment manager at Enron who started to unravel the accounting scandal happening behind the scenes. Listen here.

There's a group of people hunting down the remaining Sears and Roebuck homes, the DIY houses built from kits Sears once sold in its famous catalog.

IPOs that failed

Plenty of private companies fail once they try to go public. Failing can mean shares sell for less than their initial asking price on its IPO date, or it can look like a company pulling out of the IPO process at the last minute. Some companies with failed IPOs include Pets.com, Etsy, and Robinhood. Learn more about these companies and others here.

North American department store retail groups report sales declined from 2018 to 2023

That's according to a recent report from Bain & Company that dives into consumer sentiment around department store shopping and explores a potential reset for the industry.

Hear how the Piggly Wiggly grocery store founder attempted to squeeze short sellers by cornering the grocery store's stock

Founded in 1916 in Memphis, TN by Clarence Saunders, Piggly Wiggly was the first modern grocery store with aisles for customers to shop for themselves. In 1922, investors placed short positions, sensing that the stock may be overvalued after several Piggly Wiggly franchises in the Northeast went bankrupt. Saunders attempted to squeeze short sellers by taking out $10M and buying up nearly 99% of all available Piggly Wiggly stock. Ultimately, the fiasco ended with Piggly Wiggly's stock being permanently banned from the New York Stock Exchange and Saunders leaving Piggly Wiggly and filing for bankruptcy.

Venture capitalists were once bullish on DTC brands

While a physical store can only hold so many objects, online retailers without the limits of four walls that could sell their products direct-to-consumer could theoretically be great investments. But they didn’t always provide investors with expected returns.

Retail investors are getting burned by long/short strategies

In the US, many retail investors lack the SEC-mandated status (a high enough net worth, income, and other factors) to directly invest in hedge funds. The regulator considers hedge funds too risky for the masses. Hedge fund-like strategies have emerged as a workaround, despite potential pitfalls.

There's a group of people hunting down remaining Sears and Roebuck homes

This podcast episode dives into the history of Sears and Roebuck houses, including the people searching for these real estate relics today. Many of them were destroyed or renovated beyond recognition, so they're not easy to find or identify.

Rent the Runway recently lost over 90% of its value

The COVID-19 pandemic and increased competition post-2020 are just two factors plaguing the designer clothing rental company.

Theranos and Pets.com are among some of the biggest startup failures ever

You might have heard of Theranos, Elizabeth Holmes’s one-time blood testing company that landed the founder in prison for more than a decade after she was charged with fraud. The rest of the startups on a list of five of the biggest startup failures ever might not be as famous as Theranos, but they were met with similarly disastrous fates.

11,000 new US dollar stores opened between 2007 and 2017

Dollar store retailers experienced significant fiscal gains during the 2010s, which were then accelerated by the COVID-19 pandemic. But in recent years, dollar stores have been closing in large numbers and suffering financial hardship. Experts point to Walmart's strategy of decreasing prices to cater to inflation-fatigued customers, and point out that when Walmart does well financially, dollar stores typically suffer.

Explore Bessemer's anti-portfolio of missed opportunities

From Pinterest to Yelp, Bessemer Venture Partners—one of the most well-known VC firms—has invested in many successful companies over the years. But the firm has also kicked itself for passing on a few great opportunities, like Apple and Google. Check out the other companies in Bessemer's "anti-portfolio" here.

Explore Sears’ holiday Wish Book catalogs dating back to 1930

The Sears Wish Book was a holiday-themed version of its catalogs that helped people make Christmas gift wish lists and more from the 1930s until the early 2000s. See what they looked like with editions in this archive.

A star investment banker was fired, launching a decade-long court fight

Star bankers are the core of an investment banking firm's business, so when Perella Weinberg let their restructuring guru Mike Kramer go in 2015, he sued, launching a ten-year legal fight.

Amazon operates a 'flywheel' business model

Central to any understanding of the multifaceted nature of Amazon's business today is the concept of the "flywheel" at the heart of the company. Put simply, it's an idea that refers to a self-reinforcing cycle that drives the continuous growth of Amazon's various businesses, including its retail arm, its Prime subscription service, and more.

Warren Buffett has said not investing in Google or Amazon early enough was a mistake on his part

After avoiding investing in tech stocks during the dot-com boom, Buffett's stance on investing in tech was widely criticized. Buffett later shared his thoughts on why he regrets not investing early enough.

Many of the 2010s girlboss-era founders experienced a public fall from grace in 2020

In the 2010s, dozens of female founders were celebrated on the covers of business magazines like Inc. for their recent startup success, from Emily Weiss’s Glossier makeup brand to Steph Korey’s Away luggage company. But many of these companies were also the subject of large takedown articles around the year 2020.

Even iconic companies can get dropped from the Dow

The Dow’s lineup evolves as the economy changes. General Electric, part of the original 1896 index, was removed in 2018, after 122 years. ExxonMobil, once the world’s largest company, was replaced by Salesforce in 2020.

Amazon founder and billionaire Jeff Bezos' wealth primarily stems from his Amazon ownership stake.

American Express briefly owned Lehman Brothers

In 1984, Shearson, a retail banking company and American Express subsidiary, bought the investment banking company Lehman Brothers—best known for its historic 2008 collapse—for $360M. The businesses were then called Shearson Lehman/American Express. American Express spun off Lehman Brothers with an IPO in 1994 that attracted nearly $3B in new capital.

Watch a video that details the full history of Macy's

From the first Macy's Thanksgiving Day Parade to opening its flagship store in Herald Square, Macy's has a long and successful history despite its recent financial troubles.

Walmart has historically been one of Amazon's largest competitors

While Walmart has been America's largest retailer by revenue for over three decades, Amazon is now fighting for the title, seeking retail supremacy. In this podcast episode from the Wall Street Journal, Sarah Nassauer explores the efforts Walmart has taken to keep its crown.

Amazon accounts for roughly 40% of all US online retail sales—a much larger piece of the pie than its competitor Walmart

Although Walmart is roughly 30 years older than Amazon, the e-commerce giant has a significant lead in online US retail sales: Walmart's share is roughly 7%. Season 33 of the podcast "Business Wars," hosted by David Brown, is all about one of the most intense rivalries in all of retail.

The 2008 financial system unraveled in a wave of speculation

Michael Lewis—author of the bestselling "The Big Short"—explains how a wave of speculation (among other factors) drove the 2008 collapse, from lenders issuing risky mortgages to Wall Street turning them into fragile securities. He also highlights the few outsiders who recognized the bubble and bet against it before the crash.