“Is it a good time to sell?” That’s the most common question from owners of private insurance broking businesses. What the question really means: Are prices likely to be higher or lower in the foreseeable future? And will waiting be rewarded or penalized? It’s an entirely reasonable question. But it’s also one that often rests on the false premise that trends in valuation are predictable. In reality, markets are only easy to analyse in hindsight.
Take Marsh, the bellwether for the insurance broking sector. During the depths of the financial crisis, its shares traded at around $20. Over the following fifteen years, the share price increased many times over. With the benefit of hindsight, holding rather than selling was clearly the right decision. Equally, with hindsight, a shareholder who sold at the stock’s most recent peak ($242 on 28 March 2025) would have done even better than one who held on through the subsequent correction. Still, even those who did nothing would have generated exceptional long‑term returns (the current share price is around $170). The lesson is not that there was a “right” moment to sell, but that it is almost impossible to consistently call turning points in markets.
The added challenge of calling markets in private M&A
In private mergers and acquisitions (M&A) there’s another complication: Most transactions are funded largely by debt. The availability and cost of that debt exerts a major influence on what buyers can pay, and that introduces an added layer of uncertainty entirely outside of a seller’s control.
Importantly, for owners of private broking businesses, this dynamic has tended to dampen extremes. In recent memory, as public broker valuations rose dramatically, private company multiples also tended to increase — but by less than the public valuation. As public market valuations have since fallen back, the impact on private company pricing has also generally been more muted. The private market may move slower and with less volatility, but it’s still unpredictable.
There’s also a practical difference that’s often overlooked. A shareholder in a quoted company can decide to sell and execute that decision in minutes. An owner of a broker or Managing General Agent (MGA) would be doing well to turn a decision into a completed transaction in under six months, and it most often takes longer. A lot can change in the interim. By the time a business reaches the market, negotiates terms and completes the agreement, market conditions may have altered. Trying to “time” the market in private M&A is, to put it bluntly, basically impossible.
We all recognise the behaviour of homeowners during falling property markets: Sellers are reluctant to adjust price expectations, even though selling cheaply also means buying cheaply. Relative value often matters more than absolute value. The same logic applies — less obviously — to the sale of a private company. An owner who sold their brokerage five years ago (or longer) may still regret achieving approximately half the multiple of what they could have achieved last year. Yet those proceeds, if invested in the stock market, are likely to have produced a similar or greater uplift. Again, relative value is more important than absolute value.
Is it the right time to sell?
Based on everything presented above, the correct answer to the question is quite consistent and, for some, counter‑intuitive: The right time to sell is determined far more by personal considerations than by the state of the market. Is it the right time to exchange future, uncertain value for certainty today? None of us are getting younger. Are the demands of the business — including management depth, investment requirements, or regulatory burden — starting to feel burdensome? Is the market itself changing in ways that introduce new risks to the business model? These are the questions that matter much more than transient market values.
So, when anyone asks, “Is it a good time to sell?”, the honest answer is: If someone genuinely knew the answer, they wouldn’t be advising on M&A — they’d be a billionaire hedge fund manager.
But is it the right time for you to sell? That is a very different question. And one where experience, perspective, and a clear understanding of the tradeoffs can make all the difference.
