Alex Wilhelm

Wilhelm grew up in Oregon and later studied in Chicago. In a 2014 interview, he recalled joining The Next Web during his second year at university, dating the start to approximately 2009.⁠[1]

He studied philosophy at the University of Chicago. After graduating in 2012, he moved to San Francisco and became The Next Web’s deputy managing editor. He had previously served as its MicrosoftMicrosoftMicrosoft is a technology company founded by Bill Gates and Paul Allen in 1975 and headquartered in Redmond, Washington, with businesses spanning Windows, Microsoft 365, Azure, enterprise software, artificial intelligence, gaming and devices.Open the full entry editor.⁠[1][2]

Wilhelm joined TechCrunch in July 2013. In an interview the following year, he described keeping up with technology companies and new products as central to his work, and said he worked primarily from home.⁠[1]

After joining Mattermark as editor-in-chief, he outlined plans to expand coverage of startups, venture capital and financial trends. He said editorial decisions would be independent of the company’s commercial interests and invited outside contributors.⁠[3]

He began writing a morning column, initially called Editor’s Morning Note. It later became Morning Markets at Crunchbase News and The Exchange at TechCrunch and TechCrunch+. In 2024, he described these columns as a continuing thread in his work interpreting technology and capital markets.⁠[4]

Crunchbase News launched in March 2017 with Wilhelm as editor-in-chief. Its team combined startup funding news, data graphics and regional investment analysis, and worked with TechCrunch that year to launch the weekly Equity podcast.⁠[5][6]

In his year-end review, he reported that Crunchbase News had grown from two full-time staff at the end of 2017 to five, publishing over 1,000 articles in 2018. The team also continued its Startups of the Week collaboration with the San Francisco Chronicle in written and podcast formats.⁠[7]

He returned to TechCrunch in late 2019 to help develop Extra Crunch.⁠[8]

In an Indie Hackers interview, appearing as a TechCrunch senior editor, he reflected on building the editorial operations at Mattermark and Crunchbase News. Topics included experimenting with coverage, building an audience and developing evergreen explanations of startup financing.⁠[9]

He renamed his existing Alex Writes blog and newsletter Cautious Optimism, planning to resume weekday writing about earnings, public markets, late-stage startups and IPOs. His stated approach allowed room for experimentation at young companies while holding large technology businesses to higher expectations.⁠[4]

Episode 1953 of This Week in Startups introduced Wilhelm as a new co-host alongside Jason Calacanis, discussing technology and startup news. He also interviews founders on the program.⁠[10][11]

Wilhelm announced that Cautious Optimism had moved from Substack to a WordPress site developed by Insight Media Group. He explained that the change would support more frequent articles and interviews while retaining newsletter distribution.⁠[12]

His reporting spans technology, finance, startups and venture capital. His The New Stack author page identifies him as a former TechCrunch+ editor-in-chief and lists his reporting. Cautious Optimism is owned by his company LunchHacks and belongs to the Insight Media Group network.⁠[13][11]

His publication is at https://www.cautiousoptimism.news/ (opens in a new window) . His X account is https://x.com/alex (opens in a new window) and his LinkedInLinkedInLinkedIn is a social networking platform for professionals. It was founded in 2002 by Reid Hoffman and others, launched in 2003, and listed on the New York Stock Exchange in 2011; after Microsoft acquired it for approximately $26.2 billion in 2016, it became a wholly owned Microsoft subsidiary. Its revenue comes from membership subscriptions, advertising, and recruitment solutions.Open the full entry profile is https://www.linkedin.com/in/alexwilhelm (opens in a new window) . His public professional profile lists Providence, Rhode Island, United States, as his location.⁠[11][14][15]