Jesse Craig moved to Fargo, North Dakota in the summer of 1991 to finish his Bioengineering degree at North Dakota State University. To afford the higher rent in Fargo, he applied and was hired as the Resident Manager of a 24 plex apartment building located at 2545 14th Street South, a building he would later own.

While being the Resident Manager, Jesse worked with handicapped individuals at Friendship, Inc in between his classes at NDSU. For extra money, he also did projects for the management company of the property, NCM Properties. During one of these projects Jesse caught the attention of Paul Sather, the President of NCM. Paul offered Jesse a job at NCM as a Property Manager with one exception....that Jesse finish his degree. Part of this offer was that Paul would help Jesse accomplish his goal, to purchase his own rental properties.

Jesse purchased his first duplex, located at 1201-1203 14th Street South, for $38,000, in July 1999 and named it after his oldest daughter. The duplex was worked on for 9 months. Jesse sanded the hardwood floors, raised the double garage and poured a new slab under it, tiled the kitchen counters, painted, added landscaping and rented the units for $775 a side which was a big increase over the prior rents of $495. His daughter was his "best" helper and often on the way home after working would stop into Great Wall for Chinese.

The duplex was sold for $89,000 shortly after the 9 month remodel and those proceeds were exchanged into a 6 plex and Jesse started his own management company. This began a Real Estate career that would involve the ownership of over 1,500 units and $550,000,000 of real estate transactions. By 2025 year end, Jesse is projected to exceed $850,000,000 in projects under Craig Development.

In Summer 2014, Jesse started Craig Development, as he saw a need for housing in downtown Fargo. Through his vision he remodeled the historic Billmeyer, which is 28 units built in 1910. Jesse did the $500,000 remodel himself, from top to bottom. In completing the Billmeyer spurred his development of multiple projects in the Downtown Fargo area.

The next project was Alexandra Marie, a $4.7 million 36 plex new construction project, built on what had originally been The Billmeyer's parking lot, that was moved to a new location.

Since then, Jesse’s unique ability to put create a plan, and build, developments have brought more than 2,600 apartment homes for people to call home and 70 commercial suites for businesses.