Selling a struggling business can be an emotional journey for business owners. The challenge is not the sale itself, but the psychological and financial fog that surrounds it. Imran Hussain brings more than two decades working inside cash-constrained companies to help owners see that an exit can be a rational, even responsible, decision when handled correctly. “A lot of people get to the point where they just don’t want to be in their business anymore,” Hussain says. “They want an exit, but they don’t know how to get that exit.” As a fractional CFO and advisor at Loyal VC, a diversified evergreen fund offering accredited investors quarterly liquidity, Hussain’s work focuses on helping owner-managed businesses stabilize, reposition, and when necessary, sell without shame or unnecessary stress.
When a Business Becomes an Identity
Many of the owners Hussain advises have been running their companies for ten or twenty years. Over time, the business stops being an asset and starts becoming a proxy for personal worth. That makes the idea of selling feel like walking away from oneself rather than making a strategic choice. “They remember the days when things were thriving,” Hussain says. “Now they’re in a business they don’t like turning up to, but they don’t know what else they could do.” This identity trap is especially acute for founders nearing retirement age. Unlike younger operators who may pivot into consulting or new ventures, older owners often struggle to imagine a next chapter and businesses that should be prepared for sale are instead left to deteriorate, eroding value. There’s a real cost in waiting too long. In many cases, the alternative to a sale is often insolvency or administration, outcomes that rarely benefit anyone involved.
Detachment as a Financial Strategy
The first step in selling a struggling business, according to Hussain, starts with emotional detachment. Owners must step back from day-to-day decision-making and allow their teams to operate independently. “Let the employees be self-sufficient,” he says. “That helps you emotionally detach, but it also makes the business more attractive to buyers.” Investors are wary of owner-dependent operations. A business that cannot function without its founder signals risk.
By contrast, a company with delegated authority and operational resilience appeals to buyers seeking portfolio investments rather than full-time management roles. This detachment often improves the seller’s wellbeing as well. Removing constant operational pressure creates space for clearer thinking and better decision-making at a critical moment.
The Discipline of a 13-Week Cash Flow
Once emotional distance is established, Hussain turns to financial clarity. His starting point is a 13-week cash flow forecast, a tool he describes as non-negotiable for any business considering a sale. The exercise forces owners to confront reality. Every inflow and outflow is mapped, revealing inefficiencies that often go unnoticed for years. Hussain recalls one client who discovered they had been paying for a photocopier returned five years earlier. Beyond internal benefits, the forecast sends a powerful signal to buyers. “When an investor sees you’ve mapped out your 13-week cash flow,” Hussain says, “they think this is organized. There’s a process here, even if the business is struggling.” In distressed situations, process matters. Buyers are not expecting perfection, but they are looking for evidence of control.
Reducing Risk Where It Counts
Customer concentration is another silent value killer, with Hussain advising that no single client should account for more than 20% of total revenue. Anything above that introduces fragility that buyers will price aggressively. “If one customer makes up 90% of your revenue, you’re very unattractive to an investor,” he says. “You’re not going to get the best multiples.” Diversification takes time, and it may come late in the lifecycle of a struggling business. Even modest progress, however, can materially change how risk is perceived during negotiations.
Why Selling Is Not the Same as Failing
Hussain’s work in mergers and acquisitions has given him a front-row view of current market dynamics. Loss-making businesses are increasing, yet many sellers remain selective, hesitant to engage with buyers even in distressed conditions. There’s a disconnect that often stems from emotion rather than economics. Technology may help close that gap. Hussain expects AI-driven analysis to reduce the cost and burden of due diligence, making transactions faster and less punitive. Lower friction could encourage earlier, more rational exit decisions.
Still, the core issue remains human. Selling a business requires separating identity from outcome. Hussain believes that shift is overdue. “Sometimes these businesses need fresh eyes,” he says. “That can be good for everyone involved.”
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