This study investigates how mainstream German Jews in the first half of the nineteenth century moved from the edges of society into the German economic middle class, as their marginal occupations, especially petty commerce and peddling, inadvertently positioned them to be at the forefront of German industrialization. The narratives of Jewish businessmen, combined with articles in two Jewish newspapers, indicate that Jewish entrepreneurs of that period continued to focus on commerce and were well positioned to take advantage of niche opportunities that the German gentile population overlooked. The study also showed how these Jewish businessmen publicly supported artisanry and the German guild system, as they simultaneously used their master certifications to start their own businesses. It reveals how Jewish businessmen's thinking changed, as they moved from marginal to mainstream and impacted the way they conducted business, as they moved from selling rags to wearing riches.