IPOs That Launched Like Rockets — and Those That Flew Straight Into a Wall

If you hear the faint hiss of champagne corks this summer, that’s the sound of bankers limbering up for two long-anticipated debuts: Chime and Klarna. The FinTech duo is expected to test whether the initial public offering (IPO) window is really wide open or merely cracked. While we wait for their roadshows (and the requisite promotional hoodies), let’s lighten things up with a tour of the last quarter-century’s IPO high-flyers — and the offerings that belly-flopped so hard they left a crater in the term sheet. Think of it as the Wall Street version of “Hot Ones”: some scorch, some whimper, all entertain.

IPO Hall of Fame

(Listed in chronological order)

Alphabet (née Google), 2004: Priced at $85, adjusted to pocket-change after two splits, a single $1 invested in the auction would be worth roughly $55 today — good for a 5,400% ride. Not bad for a company that started in a garage and now seems intent on indexing Mars. (fool.com)

Visa, 2008: The payments network raised a then-record $17.9 billion and never looked back. A $10,000 stake at the IPO now flirts with $200,000, nearly a 20-bagger that also throws off dividends — credit where credit’s due. (nasdaq.com)

Tesla, 2010: Floated at $17 a share, scoffed at by Detroit, and now up 3,000 %-plus even after recent speed bumps. Investors who held through the 5-for-1 and 3-for-1 splits earned bragging rights — and maybe a Roadster. (businessinsider.com)

Salesforce, 2004: The SaaS pioneer went public at $11. Today, that $11 is about $272, meaning a $1,000 IPO ticket is worth north of $60,000, proof that recurring revenue ages like a fine cabernet. (macrotrends.net)

Shopify, 2015: From “Ottawa upstart” to eCommerce operating system, the stock has notched a mind-bending 3,600% total return in a decade, sprinkling some maple syrup on Silicon Valley’s lunch. (nasdaq.com)

(Honorable mention: Snowflake’s 2020 debut doubled on day one and is still trading ~75% above its $120 issue price, the software world’s version of a cannonball splash.) (nasdaq.com)

IPO House of Shame

(Proof that not every bell-ringing deserves a souvenir photo)

Pets.com, 2000: Raised $82.5 million in February, spent lavishly on a sock-puppet Super Bowl ad, and filed Chapter 11 nine months later. The dot-com era’s cautionary tail — or is that tale? (investopedia.com)

Groupon, 2011: Opened at $28, but slipped below its $20 offer price within three weeks as daily-deal fatigue set in. Corporate slogan could have been “Buy one pop, get one plunge free.” (techcrunch.com)

Blue Apron, 2017: A $1.9 billion market cap on day one shrank 99% before the meal-kit maker sold itself for just $103 million in 2023. Turns out investors didn’t crave a subscription to negative gross margins. (techcrunch.com)

SmileDirectClub, 2019: Debuted at $23, delisted four years later after tumbling to eight cents and filing Chapter 11. Sometimes the smile really is upside-down. (us.dental-tribune.com)

WeWork, 2021 (SPAC edition): Finally reached public markets at a $9 billion valuation—already a shadow of its $47 billion peak—only to sink more than 99% and land in bankruptcy court. SoftBank’s vision, indeed. (markets.businessinsider.com)

So, What’s the Moral of the Cap Table?

Size ≠ Success. Visa and Snowflake both staged jumbo offerings, but Saudi Aramco-scale fund-raises don’t guarantee performance — ask Facebook’s rocky first year or, well, WeWork.

Business Model Beats Buzz. Google’s auction was quirky; Pets.com’s mascot was adorable. Only one, however, could fund itself without burning through cash like kindling.

Time in Market Trumps Timing the Market. A dominant network effect (Visa), high-gross-margin software (Salesforce, Shopify) or a cult-CEO product flywheel (Tesla) can overcome almost any macro-cycle — eventually.

As Chime polishes its checking-with-spot-me story and Klarna pitches buy now, pay later (BNPL) to buy-side analysts, remember: IPO day is just the opening scene. Twenty-five years of hits and misses show the real drama starts after the confetti is swept off the NYSE floor.

Happy weekending — and may your own investments land in the Hall of Fame, not the House of Shame.