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 marketing 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 folks grow with a website, local listings and social media ads.

Real Estate Investor

1 property, multiple units.

Future retirement income.

Chief Risk Officer, Trader

Follow the charts. Student of Gann & Wyckoff.

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.


Type–5 or 6

I have in-depth knowledge on specific subjects of interest (see above) and I have clear boundaries between family, friends and work.

I’m also good at managing finances and I’m an excellent team player.

The Big Five


Those who are high in conscientiousness are organized and determined, and are able to forego immediate gratification for the sake of long-term achievement.