Matt Brezina
About Matt Brezina
Matt Brezina studied electrical engineering at Penn State and graduated in 2003. In 2006 he co-founded Xobni, an email and contacts software company that went through Y Combinator (Summer 2006) and was later acquired by Yahoo.
He then co-founded Sincerely, a mobile gifting and cards startup founded in 2011, and served as its CEO. Sincerely was acquired by Provide Commerce. He is based in San Francisco.
He now invests through Ford Street Ventures, where Crunchbase lists him as an angel investor since March 2020. He also works on street safety and city issues, including through People Protected and KidSafeSF. His X bio lists both.
On the Angel podcast with Jason Calacanis, Brezina described Dropbox as his first angel investment. The episode title describes him as an investor in 65+ startups, including Dropbox, Cruise and Ring.
Other investments he or third-party profiles name include Mailbox (acquired by Dropbox), Wanelo, Voxer, Gametime, Rescale, 15Five and Teachable. Crunchbase lists Zoba, Unsubscribe.com and Teachable as notable exits. PitchBook counts 36 investments and 26 exits, and Crunchbase counts 23 investments. The counts differ by source.
He has also been an advisor to companies including Weebly, Qualaroo, SwoopMe (from 2015), Sitter and EarnUp.
His X bio says he invests in health, AI, atoms and bits at Ford Street. The sources I found do not name specific AI portfolio companies or give investment dates for them, so none are listed here. Founders should check his current portfolio on his site or in conversation.
In the Angel podcast, he talks about backing resourceful founder-builders and about the value of a technical co-founder. He also discusses when he likes to get involved with a company and the stage at which an angel can no longer add much value.
His recent deals in PitchBook span consumer products, healthcare, fintech and climate, for example Stickerbox, Carry, Trek Health, Enara Health and Living Carbon. One third-party profile describes him as investing from pre-seed to Series A. He has not published a check size in the sources I found, so none is given here. PitchBook lists him as an active investor seeking new investments.
- Dropbox: file storage and sync company, described on the Angel podcast as his first angel investment
- Cruise: self-driving car company, named in the Angel podcast episode and on his Wellfound profile
- Ring: smart doorbell company, named in the Angel podcast episode
- Mailbox: email app acquired by Dropbox
- Teachable: online course platform, listed by Crunchbase as a notable exit
- Stickerbox: seed round on 26 September 2025 per PitchBook
- Carry: investment dated 17 July 2024 per PitchBook
- Created by Humans: investment dated 25 June 2024 per PitchBook
- Trek Health: investment dated 9 September 2022 per PitchBook
- Enara Health: healthcare technology, investment dated 7 April 2022 per PitchBook
- Living Carbon: environmental services, investment dated 23 February 2022 per PitchBook
Investing activity
Matt Brezina is listed on Lounge as an angel investor. The deals desk records Series A and later AI rounds and seeds over $10M, so smaller checks may not show here yet.
Deals
Frequently asked questions about Matt Brezina
Who is Matt Brezina?
Matt Brezina is a San Francisco angel investor at Ford Street Ventures. He co-founded Xobni, which was acquired by Yahoo, and Sincerely, which was acquired by Provide Commerce.
What stage does Matt Brezina invest in?
He invests in early-stage startups. One third-party profile says pre-seed to Series A, and PitchBook shows a seed round in Stickerbox in September 2025.
Does Matt Brezina invest in AI startups?
His X bio says he invests in health, AI, atoms and bits. The sources I found do not name specific AI portfolio companies.
What is Matt Brezina's check size?
He has not published a check size in the sources I found. Ask him directly rather than relying on third-party estimates.
What does Matt Brezina look for in founders?
On the Angel podcast he talks about backing resourceful founder-builders and about the importance of a technical co-founder.
How can founders contact Matt Brezina?
His personal site is mattbrezina.com, and he is on X as @brezina and on LinkedIn. A warm introduction from a mutual contact is the safer route, since he has not published a pitch process.
Is Matt Brezina an angel investor?
Yes. Matt Brezina invests personally as an angel.
How can founders reach Matt Brezina?
Founders on Lounge can see Matt Brezina'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 Matt Brezina to their Investor Pipeline to track the conversation.