Ashby attended Park Hill High School in Kansas City, Missouri, and graduated in 2016.

[3] He made his professional debut with the Rookie-level Helena Brewers, and also played for the Single-A Wisconsin Timber Rattlers, posting a cumulative 2–3 record and 3.59 ERA in 13 games.

In 2019, Ashby split the season between Wisconsin and the High-A Carolina Mudcats, logging a 5–10 record and 3.50 ERA in 24 appearances between the two teams.

At the end of his 1st season, he played in 13 games, 4 in which he started, and he put up a record of 3–2, with an ERA of 4.55 and 39 strikeouts in 31.2 innings.

[11] On April 5, manager Craig Counsell announced that Ashby would require arthroscopic surgery on his left shoulder, and would likely miss the entire 2023 season.