Selling a small business is usually the largest single financial event of an owner’s life.
Get it right and it repays debt, funds retirement, assists intergenerational transitions and leaves a legacy.
Get it wrong and years of goodwill creation evaporate into an avoidable tax bill or a deal that unravels under pressure.
Six factors deserve particular attention.
1. Planning well ahead
Advisers typically recommend starting preparation 18 months to three years before a sale, not after a buyer appears. The reasons are practical as much as financial.
Buyers scrutinise how dependent a business is on its owner, how concentrated its customer base is, and how clean are its financial records. All things that may take years, not weeks, to remedy, if remediation is required.
Tax outcomes hinge on it too: small business CGT concessions, including the 15-year exemption and the retirement exemption, have preconditions that reward deliberate early planning rather than last-minute scrambling to ascertain eligibility.
Some practical steps simply take time regardless of intent, such as licence transfers which can take up to 12 months. Sales that begin as reactive decisions, prompted by ill health, burnout or a partnership dispute, are consistently the ones that advisers flag as potentially ending badly.
The businesses that command premium prices are, almost without exception, the ones where the owner started planning the exit long before they needed to.
2. Valuation and deal structure
A headline price means little if the structure, earn-outs, vendor finance and warranties quietly transfer risk back to the seller. Independent valuation, clear-eyed due diligence, and legal review of every clause in the contract of sale matter as much as the number on the front page.
3. The new tax landscape
The 2026-27 Federal Budget shook up the tax regime: tax on capital gains and tax on trusts. From 1 July 2027, the flat 50% CGT discount has been replaced by a cost-base indexation model plus a 30% minimum tax on real gains, but only on gains accruing after that date. Crucially, the four existing small business CGT concessions survive, with a minor uplift to the turnover threshold for the 50% active asset reduction which rises from $2 million to $10 million, potentially bringing more businesses into scope. A new 30% minimum tax on discretionary trusts is proposed from 1 July 2028, though testamentary trusts have been carved out.
None of this is yet legislated in full, so timing a sale around these dates, rather than reacting after the fact, is now a genuine strategic lever, not an afterthought.
4. Where the proceeds go
A lump sum from a business sale is a different animal to income earned over decades, and it deserves a different plan. Ignoring for a moment the vehicle from which the sale proceeds are derived, the choice between superannuation, a trust, a company, an individual or a blend of vehicles will depend primarily upon tax and asset control (which may be different from ownership.
5. Intergenerational considerations
If children or family members are involved in the business, or expected to benefit from its proceeds, the sale needs to be planned as an estate event, not just a transaction. Questions worth resolving early: should family members buy in at a discount, should proceeds be held in trust for future generations, and how will unequal contributions to the business be reflected in unequal inheritances without causing family rupture?
These conversations are best had before a buyer is at the table, not after.
6. Guarding against predators
Owners nearing sale are a known target, for opportunistic buyers who sense fatigue or urgency, for advisrs offering conflicted “one-stop” deals, and for scammers exploiting publicity around a sale. Protective measures include running a genuine competitive process rather than accepting the first offer, using independent legal and tax advice separate from the broker or buyer’s side, and being wary of any deal structure that delays or conditions payment in ways that shift risk back to the seller after settlement.
Advance consideration of the steps that lie ahead can set up you and your family’s wealth for success. First Samuel brings together the necessary experts from our team and yours to assist at all stages of a business sale. Our particular expertise lies with tax, investment and intergenerational considerations.
We invite you to book a consultation with our experts today.
The information in this article is of a general nature and does not take into consideration your personal objectives, financial situation, or needs. Before acting on any of this information, you should consider whether it is appropriate for your personal circumstances and seek personal financial advice.