The first card is the reversed Four of Wands. This indicates that your old colleague has had some difficulties in the past. He may have had financial problems or not put enough effort into something in the past. This could affect your old co-worker's ability to successfully manage his new business.
The second card is the reversed Four of Swords. This indicates that your old colleague is under pressure at the moment. She may have underestimated the impact his new business will have on her finances, time and energy. This could negatively impact your old co-worker's ability to successfully manage his new business.
The last card is the reversed Page of Cups. This indicates that your old colleague may face problems in the future. He may not be able to handle problems that may arise while running his business. Also, he may not be able to handle the responsibilities that come with the effort he's putting into his new business.
In conclusion, considering all aspects of tarot reading, it seems rather unlikely that your old colleague will be successful in opening his own business. The uncertainty of the past and the pressure of the present together with the uncertainty of the future seem to signal that it will not be easy for him to carry on this enterprise successfully. So, from what I've read, the most likely answer to the question is "No".