To date, a little is understood about the experiences of mentors of at-risk youths. The present study sought to enrich this understanding by connecting with mentors from Flamman, a youths-prevention organization in Malmö, Sweden, inquiring about benefits and negative consequences they experienced as mentors, and what aspects contributed to the development of those outcomes. The study adopted mixed methods design but only one part of data collection was successful, resulting in four in-depth interviews with mentors from Flamman. The results showed numerous benefits deriving from a role of a mentor in terms of positive changes in personality and attitudes, development of skills, and practical gains. Some negative consequences were revealed as well, specifically negative changes in personality and attitudes, and practical risks, although those were perceived as less important than the reported benefits. The nature of the experienced outcomes resulted from the interaction of the three actors of mentoring: the mentors, the mentee, and the organization. The positive experience was generally characterized by the ability to make a difference, experience success, and nurture positive relationships with mentees and colleagues, while negative experience tended to result from lack of success, difficult relationships, and barriers placed by outer influences. Overall, the mentors perceived the experience of mentoring in Flamman as positive and beneficial.