Patrick O'Donnell
About Patrick O'Donnell
Patrick O'Donnell is based in Seattle, Washington. He is CTO and co-founder of Gumshoe AI, which Crunchbase lists as his role since November 2024. Gumshoe's own site says it was founded in 2025 at Pioneer Square Labs in Seattle with CEO Todd Sawicki.
Crunchbase lists four companies he founded. They are Urbanspoon (co-founder, 2007 to 2013), Mighty AI (co-founder, 2014 to 2017), Fresh Chalk (co-founder, 2018 to 2023) and Gumshoe. GeekWire describes Urbanspoon as a restaurant review company, Mighty AI as an AI training startup and Fresh Chalk as a local professional platform. Crunchbase also lists one exit, Smore. Earlier developer roles include Code.org, Jobster and Openwave, and most recently Outgo (May 2023 to April 2024).
Crunchbase shows a bachelor's degree in mathematics and computer science from the University of California, Santa Cruz (1986 to 1990).
Crunchbase lists 2 investments and 2 portfolio companies, with 0 lead investments. The latest is an angel round in SparkToro. Crunchbase hides the date and the other company on its public page, and no press release or portfolio announcement was found for either. He does not appear to publish a track record of his own.
No public source lists AI-specific angel investments by Patrick. His AI work is as an operator. He co-founded Mighty AI and now builds Gumshoe, which tracks how AI search tools such as ChatGPT, Gemini and Perplexity mention brands. Gumshoe raised a $2M pre-seed round led by Pioneer Square Labs, with Hawke Ventures and angel investor Ari Paparo. That is money Gumshoe raised, not an investment Patrick made.
Patrick has not publicly described a thesis, preferred stage, sector or geography. He has not published a check size. Crunchbase labels his SparkToro investment as an angel round. His operating background is in consumer web, AI data and AI search software, but that is background, not a stated focus. Founders should treat his investing criteria as unknown until he says otherwise.
- SparkToro: audience research software company. Crunchbase lists an angel round with Patrick as investor, date not public. SparkToro's blog calls him a longtime friend and credits him as a partner on 2025 research about AI brand recommendations.
- crunchbase.com/person/patrick-odonnell
- crunchbase.com/organization/gumshoe-ai
- gumshoe.ai/about
- geekwire.com/2025/marketers-are-freaking-out-about-ai-search-this-seat
- finance.yahoo.com/news/marketers-panicking-chatgpts-impact-seo-1345063
- sparktoro.com/blog/new-research-ais-are-highly-inconsistent-when-recom
- psl.com/companies/gumshoe
Investing activity
Patrick O'Donnell has made 2 investments according to Crunchbase across 2 portfolio companies, and has seen 1 exit and founded 4 companies.
Deals
Frequently asked questions about Patrick O'Donnell
Is Patrick O'Donnell an angel investor?
Crunchbase lists two personal investments, including an angel round in SparkToro. His main role is CTO and co-founder of Gumshoe AI, not full-time investing.
What is Patrick O'Donnell's angel check size?
It is not public. No source found states a check size or range.
What stage and sectors does Patrick O'Donnell invest in?
He has not stated a stage or sector focus. His one named investment, SparkToro, is listed as an angel round.
Has Patrick O'Donnell led any funding rounds?
Crunchbase shows 0 lead investments. Its listed rounds for him are as a participating investor.
What companies has Patrick O'Donnell founded?
Crunchbase lists four: Urbanspoon, Mighty AI, Fresh Chalk and Gumshoe AI. He is currently CTO and co-founder of Gumshoe AI in Seattle.
Should AI founders pitch Patrick O'Donnell?
He has not published how he evaluates pitches or whether he is actively investing. Founders in AI search or marketing software may find his Gumshoe experience relevant, but they should check fit first.
Where is Patrick O'Donnell based?
Patrick O'Donnell is based in Seattle, Washington, United States.
How can founders reach Patrick O'Donnell?
Founders on Lounge can see Patrick O'Donnell's contact details in AI Investor Contacts (paid plans), check for a warm introduction through members who worked with them under Warm Paths, and add Patrick O'Donnell to their Investor Pipeline to track the conversation.