Bob Carilli
About Bob Carilli
Bob Carilli is an entrepreneur and business strategist in Austin, Texas, with more than 30 years of experience in technology, retail and consumer brands. His Crunchbase profile says he led the production team that built John Hancock's first website and launched shopIBM eCommerce. It also lists World Wrestling Federation streaming productions, Travelocity and SABRE advertising work, Alamo Car Rental location kiosks and Kelley Blue Book site sections.
From 2011 he was CTO and Partner at Behavioral Essentials, which applied behavioral science and AI to business and was later acquired. RocketReach lists that role as running to 2023. He also owned and operated Jeremiah's Italian Ice franchise locations in the Austin area. Local press reported that he and Terra Carilli opened a Cedar Park location in 2021 and planned a second in Leander. Other roles listed by RocketReach include co-founder and CMO of Reverse Mortgage Advisors from 2006 to 2021.
He is now Founder and CEO of Systemores, which describes itself as a boutique software venture studio and research lab. It builds behavioral software, games and developer tools. He has written about behavioral systems, including the March 2026 publication Behavioral Capital, and hosts the Behavior OS podcast. He has also mentored through SCORE (Austin), SDSU career mentoring and StarterStudio.
Crunchbase records 1 investment, 1 portfolio company and 1 lead investment, with 0 exits and 6 companies founded. The round, date and company are not named in the sources found. A third-party profile lists him as an investor and advisor at LoanMonkey from 2020 to 2022, but that is not confirmed as the Crunchbase investment. He does not appear to run a fund or syndicate, and no fund size is published.
No stage, sector or check size is published. His own description says he focuses on opportunities he finds exciting, such as Systemores. He also says he mentors and advises entrepreneurs and business owners on thinking strategically and growing sustainably. His public writing centers on behavioral science, decision-making and AI in organizations. Founders in those areas, or those who value a practical operator's input, may find the closest fit. This is an inference from his work, not a stated investment thesis.
- LoanMonkey: listed by RocketReach with him as investor and advisor, 2020 to 2022. Not confirmed as his Crunchbase-recorded investment.
- crunchbase.com/person/bob-carilli
- linkedin.com/in/carilli
- systemores.com
- rocketreach.co/bob-carilli-email_1093094
- score.org/austin/profile/bob-carilli
- communityimpact.com/austin/cedar-park-leander/impacts/2021/09/23/jerem
- behavioralessentials.com/resources/the-importance-of-listening-as-a-le
- prlog.org/13163162-systemores-expands-behavioral-architecture-into-adv
Investing activity
Bob Carilli has made 1 investment according to Crunchbase across 1 portfolio company, and has led 1 round and founded 6 companies.
Deals
Frequently asked questions about Bob Carilli
Does Bob Carilli invest in AI startups?
No AI-specific investments are publicly documented. His own work sits at the intersection of behavioral science and AI, through Behavioral Essentials and Systemores.
What is Bob Carilli's check size?
He has not published a check size, and none appears in the sources reviewed. Ask him directly.
What stage does Bob Carilli invest in?
No stage preference is stated publicly. Crunchbase shows one investment, recorded as a lead investment.
How many investments has Bob Carilli made?
Crunchbase lists 1 investment, 1 portfolio company and 0 exits. Private angel investments may not be reflected there.
What companies has Bob Carilli founded or run?
He is Founder and CEO of Systemores and was CTO and Partner at Behavioral Essentials, which was acquired. He also owned Jeremiah's Italian Ice franchise locations in the Austin area. Crunchbase counts 6 companies founded.
How can founders reach Bob Carilli?
His LinkedIn profile and the Systemores website are the public channels. He also mentors founders through SCORE, though his Austin SCORE profile currently shows him as unavailable.
Is Bob Carilli an angel investor?
Yes. Bob Carilli invests personally as an angel. Crunchbase counts 1 investment.
Where is Bob Carilli based?
Bob Carilli is based in Austin, Texas, United States.