How do I move ahead in my career?

Thanks for sharing all this! There's a lot to go over, so I'm going to split my response into multiple sections.

Transitioning Into Product Management

• First, I recommend going through this discussion about SWE -> PM transition and the value it has for career path.
• In general, the best course of action is transition from SWE to PM internally within your own company vs. doing a separate degree and trying to get a formal PM position via a job switch. This maximizes your chances of success as a PM since you retain all the business context. After you succeed as a PM after an internal transfer, you can switch to another company.
• There's also a middle ground: Hybridizing as a PM while still being an engineer. There's a good chance this is doable for you since you work at what seems to be a smaller startup (2 back-end developers isn't a lot). Try to have a bigger impact on product direction by assisting with brainstorming/roadmapping, analyzing data, and participating in UXR.

Getting An MBA

• There are many clear reasons why most engineers don't pursue an MBA:
  • Most SWEs want to stay in SWE. SWEs and PMs are generally paid around the same, but there are far more engineering executive roles compared to product executive ones. There's not too much incentive to switch into PM unless you genuinely like it and/or you don't like SWE.
  • MBAs take a lot of time, costing you years. Time is the most valuable resource in tech, as tech workers have such high leverage.
  • MBAs are hard to complete, especially from reputable universities.
  • MBAs are expensive.
• That being said, MBAs are a proven, straightforward way to make yourself far more employable as a PM. Traditionally, PM roles have required an MBA, but that's changing with the rise of APM programs and allowing employees to transition internally to PM.
• However, I generally don't recommend pursuing an MBA due to the reasons mentioned before. I feel like transitioning internally/hybridizing is a far smoother (and easier) path, and most engineers I've talked to who are considering an MBA are mainly doing it due to a lack of career direction and vaguely knowing that an MBA carries some prestige to it. In fact, one of these engineers ended up switching into PM, but they did it through the tactics I mentioned before (i.e. they transferred internally).

Which Company Should You Work For?

• I recommend checking out this Taro Premium Session about how to achieve hyper-growth at an early stage startup. It will serve as a nice anchor for my thoughts here and what you can achieve at your company.
• When it comes to startups, career growth comes when the startup grows. However, it doesn't seem like your company is growing rapidly if it only has 2 back-end developers after 3 years. I feel like you should only stay if your goal is to have a good paycheck, enjoy your work, and have time outside of work to spend with friends and family. That's a perfectly fine goal to have - People will generally prioritize that over career growth once they hit their 30s.
• In general, working for FAANG/Big Tech if you haven't worked there before has a lot of career value through learning how to scale products, building up soft skills, and growing your network. I hate interview prep just as much as you do, but sometimes you have to make sacrifices. To put this into perspective, I recommend this video talking about how data structures & algorithms studying is one of the highest ROI activities you can do.
• I recommend our masterclass on choosing the best team/company for you if you haven't watched it already.

What I Think You Should Do

• If you're 100% sure that you want to try a startup again, then I think you should do that ASAP. It only gets harder as you age, and I know this as a founder who is also 30. Talk to your wife about it as creating a startup will almost certainly strain your finances.
• Here's my advice on how to best set yourself up to create a successful startup.
• If it turns out that a startup isn't feasible, then I recommend looking deeply inwards to understand what's best for you and your family:
  • If your goal is career growth: You should probably aim to go to FAANG/Big Tech, especially as you haven't worked there before. Another option is to go to startup that has a hot growth trajectory (e.g. Notion).
  • If your goal is stability: Staying at your current company seems great! I know that Taro is a platform dedicated to career growth, but I think this is a very noble and respectable option. My goal is to have empower everyone to achieve what works best for their lives - There's nothing wrong with having a goal that isn't professional growth-oriented. There are other ways to grow as a person outside of work.