James Ashford sold GoProposal for 8 figures. Learn his strategies for selling, post-sale challenges, and advice for entrepreneurs.
Weekly Pilot Briefing
I loved this week's episode, but not because of the business growth story, the company's valuation, or the actual structure of the deal. Instead, I loved this week’s episode because it dealt with the human and emotional elements of selling your business. Too many business owners are focused only on the financial aspects of their exit, failing to consider all the personal planning that needs to be done in advance of the sale.
One statistic tells us that 75% of business owners who have sold their business reported experiencing “profound regret” one year after selling. Usually, this is not because an owner did not get “their number” but rather because they did not fully and appropriately plan for “their second act.” This type of personal planning is lacking in too many owners’ exit planning process.
In his discussion with John, James details what makes a good entrepreneur and how there is a tremendous mindset shift once your business is actually sold. He states that you go from “playing to win” to “playing not to lose” and that letting go of the business, losing your purpose, and achieving a long-term goal can all cause a tremendous amount of stress and discomfort.
Late in the episode, James says he thought he was “pursuing money,” but he was really “pursuing safety.” Many of my clients state that they are really “pursuing freedom.” It all depends on how you view your life and your personal relationship with money. James mentions that “money solves some problems but creates other problems” and recommends that folks read Morgan Housel’s “The Psychology of Money.”
Knowing these things, I encourage each of you to spend some time evaluating what your personal goals are after exiting your business. What motivates you? What excites you about the future? How will you fill your time? What will your focus be? You may consider reading a book like “Strength to Strength” by Arthur C. Brooks, or working through a structured discovery like our Exit Map Express program.
You can find details about the program in the Work With Us section of our website, or you can take the free ExitMap Assessment found at the following link: https://exitmap.com/flightplanstrategies/. Please let us know how we can help you plan for your “Second Act.”
About this Episode
James Ashford built GoProposal with a clear goal: to sell. From designing the logo with potential acquirers in mind to rallying his team around the vision, James executed his plan with precision. The result? An eight-figure sale to Sage, a FTSE 100 company. But what happened after the deal?
In this week’s Built to Sell Radio, part of our After the Deal series, James opens up about life post-exit. Selling a company can bring financial freedom, but as James reveals, it also comes with unexpected challenges.
You’ll discover how to:
Prepare your business for acquisition by aligning your team with a common goal.
Navigate the transition from entrepreneur to employee in a large organization.
Identify the psychological impact of “playing not to lose” after a big payday.
Avoid losing your entrepreneurial spirit in a corporate environment.
Recognize the signs of burnout and take action before it’s too late.
Reconnect with your purpose after the sale of your business.
James’ story is one of grit, growth, and reinvention. Whether you’re preparing to sell or have already made your exit, this conversation is packed with insights to help you find your next chapter.
About Our Guest
James Ashford
Most accountants over-service and undercharge their clients. This creates a lose-lose situation, where clients don’t value what you do, and you don’t charge enough to be able to provide the level of service they actually want to pay for.
James helps accountants and bookkeepers to price more profitably, sell more confidently, and to give significantly more value to their clients.
He has achieved this in his own firm – MAP. – where along with Founder Paul Barnes, they first developed GoProposal and implemented a sales culture to ensure they were maximizing the value of their clients.
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