Jason R Weed

Serving People and Building Businesses



  • 2006 – Started a consulting business.
  • 2011 – Started Pint Sized Cabins, a rental real estate business. Slow growth.
  • 2015 – Started Stewardship Digital, a web services company. Growing! Huzzah!
  • 2018 – Started a drop-shipping business. Failed in 6 months. Learned lots.
  • 2021 – Started Gatekeeper Investment Group, a private trading and investment company.


  • multiple nonprofits
  • 3 web service agencies


  • BS in Computer Science
  • Masters in Software Engineering

Credential Collector

  • NN/g – UXMC w/Web Design & UX Management
  • PMI – Project Management Professional
  • US Department of Homeland Security and National Security Agency – Information Assurance Security Professional


CEO, stewardship digital

We help businesses and ministries grow with a fast, friendly & secure website.

Real Estate Investor

1 property, multiple units.

Slow growth, requires patience, future retirement income.


Follow the charts.

Student of WD Gann and Richard Wyckoff.

Must read books: Reminiscences of a Stock Operator, Truth of the Stock Tape, and any of the Market Wizards series.

Family Man

Husband to Cheri.
Father to 3 kiddos.

I get to walk the kids to school, eat lunch with Cheri and be home by 5:03 – every day.

Personality Tests

Working Genius


The Creative Dreamer
A passionate idealist with an endless stream of big questions and ideas to consider.

16 Personalities

The Logistician (INTJ-T) in 2023 and the Architect (ISTJ-T) in 2017.

I’m rational and quick-witted. I often times struggle to find people who can keep up.


DiSC Style–CD

I have an efficient, no-nonsense approach to my work. I value expertise and competence.