Vaibhav Gupta
About Vaibhav Gupta
Vaibhav Gupta, who also goes by Vai Gupta, is based in San Francisco, California. Crunchbase lists him as CTO of Key AI, a role it dates from October 2023. Key AI is a seed-stage company that describes itself as helping communities reach their full potential, with its CEO and co-founder Kushagra Shrivastava.
Before Key AI, he was CTO at Octillion. His public profiles say Octillion was later acquired by Tegna/Premion in January 2024. He is also listed as a co-founder of Bonfire (from August 2021) and in a product role at Veraset (from August 2019). Crunchbase credits him with 3 founded companies, and says he has been a mentor at Singularity University since August 2018.
Earlier in his career he was founder and CEO of Voix AI, which a public profile describes as acquired. He was also CEO of Bidstalk, which was acquired by AppLift, and CIO and CPO at AppLift. NFX Signal lists these dates: CEO of Voix 2018 to 2019, CIO/CPO at AppLift 2015 to 2018, CEO of Bidstalk 2013 to 2018, and CTO (India) at Airpush 2008 to 2013. His LinkedIn headline also lists AOL (Verizon) as an earlier employer.
His education includes electronics engineering at Visvesvaraya Technological University and a strategic innovation program at the Indian Institute of Management Bangalore. He also took a product management program at Stanford Center for Professional Development.
Crunchbase records 5 investments across 5 portfolio companies for Vaibhav Gupta. It shows no lead investments and 2 exits, neither by IPO. The exits it names are TurboAppeal and Bidstalk. Crunchbase lists his latest investment as a seed round in Wishberry, and it does not make the date public.
Crunchbase lists him as an angel investor at CradleX from January 2016. NFX Signal shows the same position. Most individual round details, including dates and amounts for the other investments, are not public, so this page does not list them.
He is an operator first. His investing sits alongside full-time company roles, and most of the sectors he backs match companies he has built or run.
Public sources do not list specific AI companies in his angel portfolio with dates. Third-party investor directories tag his thematic focus as AI, cloud infrastructure, developer tools and data services.
His operating work is closer to AI. He is CTO of Key AI. He founded Voix AI. His LinkedIn headline says he works in data and AI, and he has worked in ad tech. His LinkedIn also shows he spoke at the AI Engineer conference, which suggests he follows applied AI engineering closely.
Stage: NFX Signal and Evalyze describe his activity as concentrated in pre-seed and seed.
Sectors: NFX Signal lists Future of Work, FinTech, Enterprise, GovTech, Fashion and Future of Education and Work among his areas. Evalyze adds AI, cloud infrastructure, data services, developer tools and marketing tech.
Geography: He is based in the San Francisco Bay Area. His known investments include a company based in India, and the sources do not state a geographic limit.
Check size: NFX Signal lists an investment range of $10K to $25K, with a sweet spot of $10K. This comes from a third-party directory. He has not stated it publicly in a source we found, so confirm it with him directly. We found no public statement from him about what he looks for in founders.
- Wishberry: Crunchbase lists a seed round in this company as his most recent investment. The date is not public.
- Bidstalk: Ad tech company that trades mobile ads algorithmically in real time. He was its CEO. NFX Signal records a $1M seed round in January 2014, and AppLift later acquired the company. Crunchbase lists it as an exit.
- TurboAppeal: Property tax appeal service. Crunchbase lists it as an exit.
Investing activity
Vaibhav Gupta has made 5 investments according to Crunchbase across 5 portfolio companies, and has seen 2 exits and founded 3 companies.
Deals
Frequently asked questions about Vaibhav Gupta
Who is Vaibhav Gupta?
Vaibhav (Vai) Gupta is a San Francisco based technologist and angel investor. He is CTO of Key AI and was previously CTO at Octillion. He has also founded or run Voix AI and Bidstalk.
Does Vaibhav Gupta invest in pre-seed and seed AI startups?
Third-party profiles describe his angel activity as pre-seed and seed, with AI, cloud infrastructure and developer tools among his focus areas. Public records do not list specific AI investments with dates.
What is Vaibhav Gupta's check size?
NFX Signal lists a range of $10K to $25K with a sweet spot of $10K. This comes from a directory, not a statement by him, so check it before you pitch.
What has Vaibhav Gupta built or run?
He is CTO of Key AI and a co-founder of Bonfire. He was CTO at Octillion and founder and CEO of Voix AI. He was also CEO of Bidstalk, which AppLift acquired, and held earlier roles at AppLift, Airpush and AOL.
How many investments has Vaibhav Gupta made?
Crunchbase lists 5 investments in 5 portfolio companies, with no lead investments and 2 exits. The latest listed is a seed round in Wishberry.
How can founders reach Vaibhav Gupta?
His public LinkedIn profile is linked on this page. We found no personal website or X account.
Is Vaibhav Gupta an angel investor?
Yes. Vaibhav Gupta invests personally as an angel and is CTO at Key AI. Crunchbase counts 5 investments and 2 exits.
Where is Vaibhav Gupta based?
Vaibhav Gupta is based in San Francisco, California, United States.