The Realities of Selling a Business for Eight Figures: James Ashford’s Story
Selling a business for a huge amount of money sounds like a dream come true. But for James Ashford, the founder of GoProposal, it brought unexpected challenges. After selling his company to Sage, he faced emotional struggles, cultural changes, and a new understanding of success. His journey offers important lessons for business owners thinking about selling.
The Unexpected Challenges of Wealth
After the sale, James discovered that having money didn’t automatically bring happiness. He realized that chasing goals often isn’t about the goal itself but the feeling we hope it will bring.
"We aim for these goals, but it’s not the goal we want. It’s the feeling we think comes with it." – James Ashford
Wealth brought new pressures, like making decisions about things he never had to think about before. This made him question what he really wanted and what success meant for him.
Planning for Life After the Sale
Even though the sale gave him financial freedom, life after selling his business wasn’t what James expected. He had to think carefully about how to manage his money and find a new purpose. While he enjoyed the financial benefits, he also felt the weight of maintaining business standards and dealing with the long-term effects of his decisions.
"Life after the deal wasn’t exactly what I expected," James admitted.
Adjusting to Corporate Life
Moving from running a small, flexible business to working in a large corporation like Sage was a big change. At GoProposal, James and his small team could make quick decisions and take risks. But in a corporate setting, decisions were slower and more cautious.
"You can’t just say, ‘I love doing this,’ and keep going as before," James explained.
The way the company operated also changed. The close-knit team at GoProposal became divided into different groups, which weakened the original spirit of the business. Even their famous customer support system wasn’t the same anymore.
Emotional Struggles and Mental Health
James faced emotional challenges after selling his business. He went from being busy every day to suddenly having no clear direction. This led to feelings of loss and confusion, which he compared to quitting an addiction.
"It’s like a crash waiting to happen, and there’s no safety net," he said.
With the support of his wife and therapy, James began to address his feelings and rebuild himself. He used this time to reconnect with his values and think about what he really wanted from life.
Building Confidence and Finding Purpose
To regain confidence, James focused on daily habits like breath work and mentoring others. He found joy in helping people and redefining his role outside of GoProposal.
"There are parts of us where we can truly shine, but we often hide them away," he shared.
He also worked on strengthening his relationships, especially with his wife, as they adjusted to their new life after the sale.
Lessons for Business Owners
James Ashford’s experience is a reminder that selling a business isn’t just about money—it’s about what comes next. His story teaches us:
- Success Is More Than Wealth – Money alone doesn’t bring happiness.
- Be Ready for Change – Selling your business can bring big cultural and operational shifts.
- Take Care of Your Mental Health – Selling a business can be emotionally tough, so support is key.
- Know What You Want – Make sure your goals align with what truly matters to you.
Finding Meaning Beyond Business
James Ashford’s story shows that the real journey begins after selling your business. It’s not just about the financial success—it’s about finding purpose, personal growth, and staying true to yourself. His experience is a valuable guide for anyone preparing to sell their company.
The Realities of Selling a Business for Eight Figures: James Ashford’s Story
Selling a business for a huge amount of money sounds like a dream come true. But for James Ashford, the founder of GoProposal, it brought unexpected challenges. After selling his company to Sage, he faced emotional struggles, cultural changes, and a new understanding of success. His journey offers important lessons for business owners thinking about selling.
The Unexpected Challenges of Wealth
After the sale, James discovered that having money didn’t automatically bring happiness. He realized that chasing goals often isn’t about the goal itself but the feeling we hope it will bring.
"We aim for these goals, but it’s not the goal we want. It’s the feeling we think comes with it." – James Ashford
Wealth brought new pressures, like making decisions about things he never had to think about before. This made him question what he really wanted and what success meant for him.
Planning for Life After the Sale
Even though the sale gave him financial freedom, life after selling his business wasn’t what James expected. He had to think carefully about how to manage his money and find a new purpose. While he enjoyed the financial benefits, he also felt the weight of maintaining business standards and dealing with the long-term effects of his decisions.
"Life after the deal wasn’t exactly what I expected," James admitted.
Adjusting to Corporate Life
Moving from running a small, flexible business to working in a large corporation like Sage was a big change. At GoProposal, James and his small team could make quick decisions and take risks. But in a corporate setting, decisions were slower and more cautious.
"You can’t just say, ‘I love doing this,’ and keep going as before," James explained.
The way the company operated also changed. The close-knit team at GoProposal became divided into different groups, which weakened the original spirit of the business. Even their famous customer support system wasn’t the same anymore.
Emotional Struggles and Mental Health
James faced emotional challenges after selling his business. He went from being busy every day to suddenly having no clear direction. This led to feelings of loss and confusion, which he compared to quitting an addiction.
"It’s like a crash waiting to happen, and there’s no safety net," he said.
With the support of his wife and therapy, James began to address his feelings and rebuild himself. He used this time to reconnect with his values and think about what he really wanted from life.
Building Confidence and Finding Purpose
To regain confidence, James focused on daily habits like breath work and mentoring others. He found joy in helping people and redefining his role outside of GoProposal.
"There are parts of us where we can truly shine, but we often hide them away," he shared.
He also worked on strengthening his relationships, especially with his wife, as they adjusted to their new life after the sale.
Lessons for Business Owners
James Ashford’s experience is a reminder that selling a business isn’t just about money—it’s about what comes next. His story teaches us:
- Success Is More Than Wealth – Money alone doesn’t bring happiness.
- Be Ready for Change – Selling your business can bring big cultural and operational shifts.
- Take Care of Your Mental Health – Selling a business can be emotionally tough, so support is key.
- Know What You Want – Make sure your goals align with what truly matters to you.
Finding Meaning Beyond Business
James Ashford’s story shows that the real journey begins after selling your business. It’s not just about the financial success—it’s about finding purpose, personal growth, and staying true to yourself. His experience is a valuable guide for anyone preparing to sell their company.
Are you thinking about selling your business? At Breaking the Mould Consulting Ltd, we specialize in helping entrepreneurs like you navigate the complexities of selling a business. From planning your exit strategy to managing post-sale transitions, we’re here to support you every step of the way.
Contact us today to start building a plan that ensures your next chapter is as successful as the last. Let’s break the mould together!
