Switzerland has a great apprenticeship system in which you do three years of apprenticeship with 3 days of work and 2 days of school per week, after high school (and instead of college). This exists for a variety of jobs, and includes the option to do a degree that allows you to study afterwards, either during your apprenticeship (more complex school studies in the same time frame) or afterwards, as a one year, purely scholarly extensions of your degree.

If you do this study-ability option, you can go on to an applied university that offers a BA for a lot of degrees, although not all that 'proper' universities offer. Afterwards you can go on to an MA still.

In the entrepreneurship world, three years may be too much. But I can see a solution in figuring out a system where each company keeps each apprentice for one year, so each apprenticeship includes work at three different companies. This would allow the apprentice to get to know the world of start-ups and big companies alike, allowing him to make a differentiated decision when it comes to search for an employer afterwards.

While many companies in Switzerland will prefer a university graduate over an apprentice, I do think especially Silicon Valley would be open to look at (at that point) experienced programmers with a wide variety of start-up and enterprise experience under their belt, as well as a decent basic level of general knowledge due to the two days of school each week.

What I'm coming at is that I doubt you would have to reinvent the wheel. Look at well-organized examples of apprenticeship-systems around the world, adopt and adapt the best-fitting one, and make it work for your ecosystem. It's a great way to make more practically oriented people more valuable for society.