I once talked a widow out of selling me a great deal. It's still one of the best pieces of advice I've ever given, and it earned me nothing.
He was one of the first clients I ever worked with. A legend — larger than life, outspoken, direct, but hugely popular and likeable. I cold-called him randomly as a student. I was doing a tenant-find service, I had students looking to rent, and I asked if he was interested. He said yes on the spot. Wanted to meet, wanted to see what I could do. I brought the students along, and it grew from there.
Over the years he built a good portfolio — a couple of million across ten-plus assets, a mix of newer residential houses and HMOs, and critically, all of it mortgage-free. He'd done a proper job.
Then he died, relatively suddenly, and his family took it all on.
Managing that many properties and a full tenant portfolio isn't straightforward if you've never done it before. A few months in, they were finding it hard. By then I'd moved direction and wasn't handling their letting and management anymore — so there was nothing in this for me. But they came to me anyway, which told me something about the trust that was there. His widow said she was looking to sell a couple of the key assets. The stress of one or two stickier units that were harder to let had tipped her toward getting rid.
It didn't make sense to me. It would have been a great deal for whoever came in and bought it. But it was a poor decision for her — and someone had to actually walk her through why.
So I did. One property he'd bought around fifteen years earlier for £65,000. By the time of this conversation she reckoned it was worth at least £150,000, and it brought in strong income — around £30,000 a year at the time. No mortgage against it.
I laid it out plainly. This has gone from £65,000 to £150,000 in the years he held it, and it's been paying strong income all along. That £150,000 could double again to £300,000 over the next ten years. So what are you going to buy now, with the money from selling it, that doubles in value like that AND keeps paying you that income at the same time? What does both?
She didn't have an answer.
And here's the part I made sure she understood: even if she genuinely could make a similar return elsewhere, selling still didn't make sense. She'd be taking on all the risk and hassle of finding and running something new, to replace an asset that was already doing the job, mortgage-free, with no effort required beyond holding it. The bar to beat wasn't "can I make money elsewhere" — it was "can I beat a paid-off asset that already doubles and pays me." That's a very high bar.
I said don't sell.
She kept it.
And here's how it played out. She held it for years on the back of that conversation, took the strong income the whole way through — and this year she sold it for around £350,000. Ten years on from me telling her that £150,000 could double, it had done exactly that and then some — £350,000. The prediction wasn't a guess dressed up to sound clever; it played out almost to the letter. When we spoke, she told me, without me fishing for it, that not selling back then was the right decision. She'd had the income all along, the value kept climbing, and now — with her grandchildren grown and everyone older — she's sold on her own terms. The plan is to buy a holiday home and actually enjoy it. £65,000 to £150,000 to £350,000, with years of strong income in between, and a sale made from strength rather than stress.
That's the part people miss about selling. The question is never just "what's this worth?" It's "what would replace it?" And even if something could replace it, would it be worth the risk and effort of swapping out an asset that's already paid off and already doing the job? A good, mortgage-free asset throwing off income and growing in value is extraordinarily hard to beat — and the moment to sell one, if ever, is from strength, not from stress.
I could have bought that asset. It would have been a good deal for me. But it would have been the wrong deal for her — she'd likely have spent the proceeds and never seen that £350,000, or the years of income, or the holiday home. Turning it down cost me nothing I'd want to keep.
If you're thinking of selling a good asset, can you actually answer the only question that matters — what are you going to replace it with?
