This is what happens when you start a company on a whim, and then forget your raison d’être. Investors and early employees with stock options wanted to cash out, but Chesky had dreams and resisted the disclosures that going public would bring:
Reuters interviews with more than a dozen Airbnb executives, advisers, investors and employees show that Chesky put IPO plans on the backburner as he sought to turn the company into a full-fledged travel agency, adding “experiences” so guests could participate in vacation activities such as book-guided tours of local attractions. By increasing spending on these ventures, he sacrificed Airbnb’s profitability, the IPO prospectus shows.
It took years of pressure from investors and employees, as well as a deterioration in Airbnb’s finances during the pandemic, for Chesky to give up on his expansion plans and commit to a listing. Airbnb is poised to seek a valuation of around $30 billion, less than the $50 billion that investment bankers told Chesky the company could have been valued in a listing two years ago.