I'm looking for advice.

I'm looking for advice. In my current role at a small startup, there are aspects that I like, things I'm hoping that might pan out if I stay, but I'm seriously considering if it's time for me to move on. Problem is that if so, I want to keep a good or at least cordial relationship with the people here, particularly my boss.

Sorry, there's quite a bit of context to provide but I tried to give it fully and succinctly.

It's a small bootstrapped startup, which I joined two years ago when my boss, the co-founder and director of strategy, posted to his socials that he was looking for an apprentice, someone to help him with the many tasks within email and social media marketing, strategy, and operations that fell under his hat. It would also be a learning opportunity, like a paid internship/being a paid junior employee. I applied and was selected, and stayed in that role for about 9-10 months – then left for a full-time job, then came back after six months because that full-time job was an awful fit. The startup has been entirely remote for the decade it's existed, for context, so I never went into an office.

What I really like about the startup: my boss has no corporate veneer to him. He's a very real person, all about trying tests, learning, iterating, and being a good human being. The culture is genuine, and the people are quality people. It's not micromanaged; I can work on my own schedule, with minimal weekly meetings. I love that, but this actually bleeds into something that might be a downside, that I'm wondering if I've relaxed into/hidden behind for too long. Which is this: Because the startup is small and not very structured or rich with resources, plus there aren't many people who are more on the non-research side of things, I don't get training.

I joined just a few months after college, where I was pre-med and didn't do internships for real-world experience, so I think the lack of training kind of matters since I never explored what I'd want to do if it wasn't being a doctor. Since I joined the startup, I've taken ownership of a few recurring tasks like social media, but the big possibilities come in the freedom to strategize or ideate, implement, and drive things forward or create systems. I haven't built momentum on projects though. There's so much that could POSSIBLY be done to grow the startup that I feel like there are always 10 different things I could work on.

The startup has existed for a decade and is undergoing a phase 2 relaunch of the website and product in a few months. Admittedly it hasn't been an extremely successful startup so far in the grand scheme of things, but the hope people have is that this overhaul of the website and organization will be a launchpad for faster growth. Another thing is despite the fact that this startup makes < $3.5M revenue per year, my boss is well-connected and knows or is friends with some big entrepreneurs, such as Mark Manson or Ramit Sethi.

The combination of him being a well-meaning person, being connected to successful people, him having given me my first working opportunity, me respecting the team, and me not knowing whether or how fast the impending product overhaul is going to affect the startup's trajectory all feel like the things that are holding me back from quitting.

I graduated from college 2 years ago, so I'm still young. This is a nice place to be, but I'm paid very little (<$40k full time) and there's not much training, resources, or guided learning opps. I have ambitions – I want to become really good at a few skills, establish myself to others as an expert in whatever I do, and earn a lot of money.

I keep hoping that the startup will grow huge soon and I will earn and learn more, but recently I've been looking into other things such as learning software engineering or starting dropshipping. I've found some more structured programs in those avenues (bootcamp/apprenticeship for SWE, dropshipping mentorship) and if I had full time, I could commit to those and see how much I can learn, but I don't have full time since I still work at this startup.

Should I quit? What do you think? I seriously would welcome any thoughts. I think because I'm looking at other learning and growth opportunities that seem to have more guidance and teaching, I've kind of lost my motivation to continue working at this startup, but I don't want to make a rash decision, and also I want to stay on good terms with them because they're good people.

Thanks so much!