James Ashford always wanted to be an entrepreneur, but the journey wasn’t a straight line.

After trying different businesses, taking on different jobs and learning from other entrepreneurs, James eventually found his way into the accounting industry. He built a piece of software, bootstrapped the business with no investment, and within five years sold it for an eight-figure sum.

In this episode of Success or Excuses, James Fleming sits down with James Ashford to explore entrepreneurship, mindset and what it really takes to scale a business. James Ashford shares how his early belief around business and freedom shaped his journey, why software became the route he took, and how solving sales problems became the foundation of his business.

He also speaks about belief systems, coachability, setting goals beyond your current capability, and why business owners often need to look deeper than strategy when they hit a sticking point. Alongside that, James Ashford reflects on health, relationships, self-awareness and the importance of building success across every area of life.

James Fleming brings his own perspective into the conversation, sharing his thoughts on mindset, goal setting, coaching, relationships, health and what it takes to stay at the top of your game.

Key moments include: ✔️ James Ashford’s early desire to become an entrepreneur ✔️ Trying different businesses before finding the right path ✔️ Building software for the accounting industry ✔️ Bootstrapping the business with no investment ✔️ Selling the software business for an eight-figure sum ✔️ Why sales problems sit at the heart of many business challenges ✔️ Mindset, belief systems and business foundations ✔️ The question business owners should ask when they hit a sticking point ✔️ What makes someone coachable ✔️ Committing fully to a goal ✔️ Why health and fitness matter in business and life ✔️ James Ashford’s top advice on accountability, learning and self-awareness ✔️ His book, Scale Strong Exit Big

Follow James Fleming LinkedIn → https://www.linkedin.com/in/jamesflemingtpwtd/ Instagram → https://www.instagram.com/successorexcusespodcast YouTube → https://www.youtube.com/@SuccessorExcusesPodcast Website → https://thepowerwithintraining.com/

Follow James Ashford LinkedIn → https://www.linkedin.com/in/jamesashford/ Website → https://jamesashford.com/

Timestamps [00:00] Introduction to James Ashford [00:00:54] James Ashford’s early desire to become an entrepreneur [00:01:30] Trying different businesses and learning from others [00:01:50] Building software in the accounting industry [00:02:00] Bootstrapping the business and selling it for an eight-figure sum [00:02:31] Why James Ashford moved into software [00:03:10] Solving sales problems inside businesses [00:05:30] James Fleming on entrepreneurial mindset and vision [00:06:06] Belief systems as the foundation of business growth [00:10:16] Hitting sticking points in business [00:11:20] Asking “who do I now need to be?” [00:13:16] Coachability and being open to difficult conversations [00:17:28] James Ashford’s entrepreneurial mindset and early commitment [00:19:50] Burning the safety net and going all in [00:20:30] Setting goals beyond current capability [00:23:18] James Fleming on dominant thoughts, goals and action [00:25:10] Achieving the goal and realising it’s about the climb [00:27:45] Building a complete game across life and business [00:28:00] James Fleming on relationships, health and feeding your mind [00:29:57] Why health comes first [00:32:52] James Ashford’s top three pieces of advice [00:38:05] James Ashford’s book, Scale Strong Exit Big [00:42:02] Where to connect with James Ashford [00:42:56] Closing thoughts