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Selling a business usually isn’t easy
- and it’s never simple.

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Even the smoothest deals based on the best exit planning are complex.

Selling a small business is complicated, and unpredictable events and powerful emotions are almost always part of the equation. The Emotional Side of Selling a Small Business is an entrepreneurial fable that shines a light on these lesser-known aspects of selling - helping owners steel themselves for the challenge.

Alex is the worn-out founder of a small, successful managed IT services provider who decides it’s time to sell after being approached with a serious offer. But just as a deal seems on track - and he’s excited by dollar signs and the allure of freedom - a series of unforeseen challenges send him on a rollercoaster of emotion, ultimately threatening the sale.

The story may be fiction, but it's entirely "true". This fable is rooted in the experiences of the author and multiple colleagues and clients he's worked with during his entrepreneurial and business coaching careers. From experiencing the sudden motivation to sell and the guilt and worry over telling employees to the fear and indecision when due diligence uncovers surprises, you’ll read what can happen (and often does) during the sales process.

Many books and guides explain the mechanics of a sale, including how to value a business, prep it for buyers, and structure agreements. But few resources highlight the dramatic emotions that can kill a deal and the surprises that happen along the way. The Emotional Side of Selling a Small Business fills this gap.

The book also features
six non-fiction case studies showing the challenges faced by other entrepreneurs who sold their businesses. Crucial topics include valuation processes, differing contract structures, the search to find and choose quality buyers, and the unforeseen hazards of succession planning. Then, there is the aftermath of a sale and how different individuals have coped with letting go of the businesses that dominated their lives.

Everyone who owns a business must exit it at some point, and they should steel themselves for the hidden challenges beyond contracts, valuation, and ROI. The Emotional Side of Selling a Small Business is a
guide to expecting the unexpected - and not falling prey to powerful feelings that can derail a sale.

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Jamison has been a serial entrepreneur for 25 years. He built Arterian (formerly JWCS), an MSP that he grew from a 1 man shop to 40 staff through both organic growth and the acquisition of 4 other IT Services companies.


He went on to Co-Found 3 SaaS companies including Teamatics, SmileBack, and TimeZest and currently serves as a fractional CEO for SmileBack and Chairman of TimeZest. He enjoys his role as a Strategic Coach and Consultant for several clients in the US.

His background includes:

  • Founding and operating companies in the SaaS and IT Services space;

  • Participating in and moderating professional peer groups;

  • Coaching and Consulting for organizations in the SaaS and IT Services verticals

  • Speaking on a range of topics from Cloud to M&A to People.

Jamison currently lives in Las Vegas, Nevada and travels constantly.


Jamison West masterfully draws us into the life of Alex, a longtime MSP owner, who grapples with the real world considerations of whether or not to sell his business. What West makes so clear is that if you don't take control of the emotional rollercoaster of selling, the rollercoaster will take control of you. Designed as a gripping fable, The Emotional Side of Selling a Small Business, acts as both a guide and a caution for owners that prepare to ask themselves, "Do I want to sell my business now?".

Russell Benaroya, author of One Life to Lead and co-founder, Stride Services

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