From Fired to $25K Per Speech: Gail Kasper of Gail Kasper LLC Reveals the Real Secrets to Business Success, $600K Contracts, Authentic Leadership, Sales Mastery & Scaling from Solo to a Powerful Team of 5. (Episode 765 - Gail Kasper)

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

According to Gail Kasper of Gail Kasper LLC, the hardest thing in growing a small business is dealing with failure and having the resilience to keep going despite repeated setbacks. She explains that as an entrepreneur you get “hit in the face” many times through failed projects, wrong decisions, or ideas that don’t take off, and the real challenge is not letting those moments stop you. Instead of quitting, she believes the key is to keep pushing forward, learn from mistakes, take action, and stay committed even when things feel uncertain or discouraging.

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

According to Gail Kasper, her favorite business book that has helped her the most is Atomic Habits by James Clear. She values its focus on small, consistent disciplines rather than just chasing big end goals, emphasizing that daily incremental improvements create real momentum. For Gail, the book reinforces that tiny wins build confidence, strengthen habits, and ultimately drive long-term business success.

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

According to Gail Kasper, she recommends podcasts and learning resources that strengthen mindset, sales, and brain-based performance, including Huberman Lab for its science-backed insights on stress and peak performance, and The Ed Mylett Show by Ed Mylett for its focus on growth, vulnerability, and high-level thinking. She values resources that blend psychology, communication, and practical application, believing that understanding how people think—especially in sales and leadership—gives small business owners a strong competitive edge.

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

One highly recommended tool that Gail Kasper often points small business owners toward is HubSpot CRM, because it helps organize leads, track sales activity, automate follow-ups, and manage customer data in one place — all without needing a big tech team. Gail emphasizes that having a system that captures conversations, schedules reminders, and analyzes what’s working versus what’s not can dramatically improve consistency in sales and client relationships, which is essential for growth. If you’re just getting started, HubSpot’s free tier gives you powerful CRM basics, and you can scale into its marketing and automation tools as your business expands.

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

According to Gail Kasper, the advice she would give herself on day one of starting out in business is simple: move and take action. When she was suddenly on her own with no money in the bank, she learned that inaction is the real danger, not mistakes. She would remind herself to stay logical instead of emotional, keep pushing forward even when uncertain, and allow herself to fall and learn along the way, because consistent action is what ultimately creates momentum and success.