Answer
Paul was raised with a familiarity with both Jewish and Gentile culture. On the one hand, he was a devout and zealous Jew who studied under the famous rabbi Gamaliel in Jerusalem (Acts 22:3; Gal. 1:14). On the other hand, he was born in the Gentile city of Tarsus (Acts 22:3), and evidently spent some of his adult life there as well (Acts 11:25). He knew Gentile culture well enough to live among Gentiles without giving offense to them, but also without compromising his commitment to the law of Christ (1 Cor. 9:21). His familiarity with these different groups gave him an ability to communicate well with both of them. He was also a natural-born Roman citizen (22:27-28), and his citizenship gave him great protection and freedom to approach many different groups in many different areas.
Initially, Paul was able to spread his message to both Jew and Gentile by preaching in the Jewish synagogues (e.g. Acts 13:5,14,42; 14:1; 17:1-2,10,17; 18:4,19). He was able to reach both groups in this way because the synagogues contained not only Jews, but also God-fearing Gentiles (Gentiles who worshiped the God of the Bible, but who had not been circumcised and who apparently did not observe the dietary laws, e.g. Cornelius [Acts 10]). A good example of both groups being simultaneously present in the synagogue can be seen in Acts 13:16,26.
Another way Paul was able to reach different groups was by speaking in the public arena, and sometimes by doing miracles to call attention to his message. For example, in Lystra (Acts 14:8ff.) Paul healed a lame man, and attracted the attention of many worshipers of the Greek gods (clearly these were neither Jews not God-fearing Gentiles). Although this event ended rather badly for Paul (he was stoned and left for dead), it did evidentially result in a church being planted in that city (Acts 14:21-22). Similarly, in Athens he argued with the philosophers in the Areopagus (Acts 17).
Answer by Ra McLaughlin
Ra McLaughlin is Vice President of Finance and Administration at Third Millennium Ministries.