LookSmart is an American search advertising, content management,[2] online media, and technology company.

It provides search, machine learning and chatbot technologies[3] as well as pay-per-click and contextual advertising services.

[8] The name "LookSmart" is a double entendre, referring to both its selective, editorially compiled directory and as a compliment to users whom the company thinks "look smart".

[9] LookSmart was founded as Homebase in 1995 in Melbourne, Australia by husband and wife Evan Thornley and Tracy Ellery, executives of McKinsey & Company.

[2] The original concept of Homebase was to build a female and family-friendly web portal to supplement the Reader's Digest magazine.

[2] The founders and former McKinsey's employee Martin Hosking instead proposed a cheaper leveraged buyout of Homebase.

[10] In June 1997, the search engine underwent a major redesign, dropping its original Java-based browsing system.

[11] LookSmart was sold back to the founders as well as Martin Hosking through a leveraged buyout in 1998, with Reader's Digest providing a $1.5 million loan and retaining about a 10% equity stake.

[14] By 1999, the company had 500 employees and LookSmart was the twelfth most visited website worldwide with 10 million users, behind AltaVista and ahead of Snap.

[2][16] In May 1999, LookSmart formed a strategic partnership with direct-response marketing company Guthy-Renker and acquired some of their assets from their e-commerce division for $3 million.

[22][23] In December 1999, LookSmart purchased FutureCorp and its free email service Start for more than $5 million from its co-founders Michael Mak and Bardia Housman.

[36][37] As a result of the dot-com bubble bursting in late 2000, the company fired 172 employees or 31% of its staff in January 2001 to cut costs.

[39] Also after the dot-com bubble burst, LookSmart paid $90,000 to transfer 52.8% of its ownership of FutureCorp back to its founders.

[42][43] In July 2002, BT LookSmart acquired UK Plus from Associated New Media (ANM) for an undisclosed amount.

[49] On 9 July 2003, LookSmart announced that they had reached an agreement to provide listing services in the United States for web portal Terra Lycos.

[55] In April 2004, LookSmart acquired Net Nanny from BioNet Systems, LLC for $5.3 million in stock and cash.

[84] LookSmart, Ltd., the company's former entity, completed a merger with Maritime Technologies Corp., a subsidiary of Pyxis Tankers Inc., on 28 October.

[86] On 13 April 2017, LookSmart Group announced partnerships with the Clickable Institute of Technology, Entrepreneurship and Digital marketing and Richie Bello West to help veterans, minorities and immigrants at Silicon Canyon.