Founder of Leave Law Behind — shares how he transformed his own career shift from law into a thriving online business helping unhappy attorneys pivot, scaling to $500K a year through coaching, courses, and smart automation. (Episode 746 - Casey Berman)

1. What do you think is the hardest thing in growing a small business?

According to Casey Berman, the hardest thing in growing a small business is feeling worthy of success. He explains that as the business starts making good money, many entrepreneurs struggle internally with questions about whether they deserve it or how success might change them. Casey admits he once worried about becoming greedy or losing his values but learned that money itself isn’t the issue—it’s the love of money that causes problems. Over time, he realized that maintaining generosity, reinvesting in the business, and focusing on helping others allowed him to embrace success without guilt.

2. What's your favorite business book that has helped you the most?

Casey Berman’s favorite business book that has helped him the most is The Million-Dollar, One-Person Business by Elaine Pofeldt. He found it inspiring because it showed that it’s possible to build a lean, highly profitable business without a large team — something that aligns closely with how he runs Leave Law Behind. He also mentioned Rich Dad Poor Dad by Robert Kiyosaki as another influential read, especially early in his career, because it opened his eyes to the difference between being an employee and becoming an entrepreneur.

3. Are there any great podcasts or online learning resources you'd recommend to help grow a small business?

Casey Berman recommends several great podcasts and online resources for small business growth, including the Work From The Inside Out podcast episode “Discover Your Unique Genius to Build Meaningful Work,” where he shares how to align your strengths with meaningful entrepreneurship, and the Digital Marketing Success Stories episode with West Kraemer, where he discusses strategies for building a niche audience and online following. He also shares practical business insights on his own website, www.caseyberman.com, focusing on growth, purpose, mindset, and transitioning from employee to entrepreneur. These resources emphasize discovering your unique value, mastering marketing in your niche, and developing the mindset needed to confidently grow and sustain a successful small business.

4. What tool or resource would you recommend to grow a small business?

Casey Berman shared that the most crucial tool for growing a small business is a robust CRM platform, which he credits as the central nervous system for managing all customer interactions and streamlining operations. He specifically highlighted the value of a CRM with integrated texting capabilities, like Salesmate.io, for enabling effective and personalized outreach to clients. This system allows a business to consolidate contacts, automate key processes, and handle payments seamlessly from one unified hub. By implementing such a foundational tool, companies can achieve greater efficiency and scalability without needing a large team. Ultimately, he champions a powerful CRM as the key to systematizing sales and marketing for sustainable growth.

5. What advice would you give yourself on day one of starting out in business?

Casey Berman would advise his day-one self that the entrepreneurial journey is an ongoing process of personal growth, not a destination to be reached. He would emphasize the critical importance of learning to enjoy the entire slog, with all its inherent ups and downs, rather than just chasing a future moment of "success." He'd stress that true happiness is found in the process of becoming your ideal self through the challenges of building a business. Finally, he would encourage himself to see and appreciate his own development, recognizing that the person behind the business is the most important project of all