What pushed your search over the hump?

I have about 4 years of experience in tech as an implementation specialist and project manager. I am applying to entry-level jobs that are lower in pay, title, and responsibility than what I was last doing in tech. I'm college-educated, worked in hospitality for 7 years, am personable, am building a startup as a side project, and enjoy making a difference in people's lives. It's been since October of last year and I don't know what to do differently. I've been mass-applying, reaching out to hiring managers, connecting with my network, and have different resumes for different types of jobs.

I know this sounds like a rant but I feel like I'm missing out on something that other people are doing and I have no idea what it is. If anybody has any tips that could help fill in some gaps, I'd love to hear what has worked for you. Thanks in advance to anyone who chimes in!