On the surface, this is not a chart of someone I would worry about, he has a lucky chart with many gifts - health, charm and masculine energy.
Looking a little closer, there are some indicators that concerns me. Also some details you mention are also concerning.
I have to ask, how well do you know this person in terms of personal ethics, dealings and deeper motivations?
Judging by your username aqua, I surmise you are an Aquarius. Aquarius generally loves their friends, and treat them like family. You seem very well-intentioned to help your friends. Sometimes in their loyalty to their friends, Aquarius can be naive to what's really going on.
I realize this may not be what you are asking for, and my suspicions can be wrong. But I just had to first ask the question where potential character clues and indicators lead me.
On the more practical and useful front, he has a stellium in Gemini so he's going to be restless and try everything. This is just the way he is. But mercury / venus are making poor aspects to his midheaven, so literature, beauty and fashion are absolutely not the way to go, although he will feel a certain obsession to it. Sun is in positive aspect to the midheaven, along with the aggressive driving force of the moon. I interpret this as he will have luck in some type of leadership sales position.
As a gemini with Sun in the first (trining the MC), his sales ability and big personality will be recognized by his superiors. His aries moon will fuel him to want to be numero ono as an internal motivator. Other talents support it, where the only problem I see are power struggles that originates between him and potential superiors or co-workers.
My take is he can succeed in sales, possibly sales leadership leading a team, and it will be a fantastic utilization of his talents, energies and monetary outlook. Also from a practical and non-astrological standpoint, I do not know how things are in his country, but in general, you do not need advanced degrees to get into most types of sales positions, whether corporate, high end or low end. It takes social ability, great people skills, and other types of skillset to succeed, such as being able to think from your customer and audience's perspective, and making deals happen. Advancement will be based on results, if you become a top seller, many places will want to recruit you. Furthermore, it seems he has some type of entreprenuerial zeal in him to take the risks he has and go against convention. And one reason he has failed as an entrepreneur is because he does not know how to sell, either himself, his brand or his products. He was probably using his energies in the wrong area, assuming the world felt exactly as he has, thus he obtained little result. So an experience there and mastering how to sell will be useful to him in the long run, regardless of whether he continues to pursue entrepreneurial ideas, or stay in more conventional jobs.
Also, his chart signature seems like a baby to me - what I mean by the word is that he wants to start aggressive ventures, here and there. Yet he failed to develop or master critical skillsets that are necessary before he starts ventures (Saturn, Capricorn). He wants to go too big, too fast, too unfocused and too impatient. So failure is not only a logical result, but absolutely assured. For example when you build a house that can weather storms (a career, a business), you have to start and master foundations first. Only then will his "house" not tumble down in the wind.
It also seem to me he may be one of those heavily influenced by this new generation's zeal of startups and like. You mentioned he dropped out of conventional studies, and invested all his personal money to beginning a risky venture (a dream) that is not guaranteed. Statistically, most of the risky, startup ventures end in failure (whether its a new business, or something like an actor or fashion designer). Most of the entrepreneurs fail, learn the lessons and start again in a new direction. Typically they learn what they did wrong and do not repeat the mistakes a second time. It's almost part of an inevitable cycle.
I will be more worried if he does not reflect on where he went wrong, and the mistakes he made in his risky ventures. Only by learning from his lessons, can he avoid the invisible traps and pitfalls, in order to succeed in a future venture.
I think where a friend can be of help is helping him analyze where he went wrong, to reflect and understand mistakes, not to blame, but as valuable experience and insight, so one can transform a failure into a future victory.
For example, if he wants to do something (fashion designer), he needs to first research how other people have done it. What did it really take for others to succeed? Was it social connections? Sales ability? Ability to spot what the public wants? Design talent? Usually its a combination of distinctive characteristics behind the scenes, and its never just one thing. Then he needs to realistically assess what he has that can make him stand out, what he lacks, then form a temporary strategy. After the initial foundation is met, then act. But not before. And lastly, don't put all of his eggs in one basket, what will be his backup plan if the gamble does not work out?
So to summarize:
1. He needs to learn how to take calculated risks. Action needs to be backed up with research, assessment, mastering of critical areas. Gambling without being 'calculated' is like traveling without a map. It assures failure.
2. A tenure in sales will benefit him in multiple areas. It will use his gemini talents, aries desire to be number one, taurus monetary concern, Jupiter on the ascendant gift to be liked immediately. And it will be practical knowledge so he can utilize and apply the skills and lessons to all his potential, future endeavors. Master this area and a lot of things will be smoother sailing in the future.
3. Where a friend can be of maximum help is to help him analyze the root cause of failures, respectfully but honestly and positively. Without stroking people's egos or telling them what they want to hear. However, you have to keep a balance. Remember there are things that are not privy to you, and internal mechanisms you may not understand. There are only certain things you can do and a limit to what you should feel responsible for.
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