Ask any long-time investor about their worst decision and you will usually hear about a moment when they were completely sure. That is exactly why getting a second opinion on an investment decision matters most when you feel most certain. Today’s story follows a fictional trio of friends in Pune who ran a small investing group, nearly made a big, hard-to-reverse move, and paused just long enough to let an outsider take a fresh look.
Quick disclaimer before we dive in: this is a story about decision habits, not a stock tip or financial advice. Nothing here says what you should buy or sell. Talk to a registered professional about your own situation.
Meet the team
Nikhil, Sana and Rohan met at their first job and started pooling a monthly amount into a shared portfolio. They had a simple routine: a Sunday call, a shared spreadsheet, and a rule that all three had to agree before any trade. For a few years it worked nicely. They held a mix of index funds and a handful of large, familiar companies, and they were proud of how disciplined they had been.
Then Rohan heard about a pre-IPO opportunity. A friend of a friend could get them unlisted shares in a fast-growing consumer brand. The story was exciting, the brand was everywhere on social media, and the shares were supposedly available only for a short time.
The big decision on the table
The proposal was bold. Rohan suggested they redeem most of their index-fund holdings and move that money into the unlisted shares. “This is the one,” he said on the Sunday call. Sana loved the brand. Nikhil was a bit nervous but did not want to be the person who held everyone back.
Here is the thing about this decision that made it different from their usual trades. Unlisted shares can be hard to sell. There may be a lock-in after listing, prices can be difficult to discover, and if the company never lists, getting out can take a long time. In other words, this was not a move they could easily undo next week if they changed their minds. If you want a refresher on how that market works, our earlier primer on investing in shares before they list covers the basics.
The moment someone said “wait”
It was Nikhil who finally spoke up, a day before they planned to place the order. He sent a message to the group chat that read something like: “I’m in if you both are. But we always agree as three people who think alike. Can we ask someone outside the group to look at this first?”
Sana was annoyed for about an hour. Rohan felt it was a waste of time. But their own rule said all three had to agree, and Nikhil was not agreeing yet. So they decided to get a second opinion.
Picking a reviewer with no stake in the answer
The friend of a friend selling the shares was obviously not independent. Neither was Rohan’s cousin, who already owned some of the same stock. They wanted someone who would earn nothing whichever way they decided and who had not been part of the excitement.
They landed on Meenal, a former colleague who now worked as a fee-only financial planner. She agreed to spend an hour on their question as a one-off favour, on the understanding that she was not going to manage their money or sell them anything. That independence was the whole point.
What they brought to the review
Meenal asked them to come prepared. They put together:
- Their current portfolio, with what each holding was and roughly how much of the total it made up.
- The written details they had received about the unlisted shares, including any lock-in or transfer terms.
- What the money was ultimately for: Sana was saving for a home, Nikhil for further study, Rohan for nothing in particular yet.
- How soon each of them might need to access the money.
- One clear question at the top of the page.
The question took them a while to agree on. They finally wrote: “Does it make sense, for the three of us, to move most of our pooled money into this one unlisted holding?”
The conversation that changed the plan
Meenal did not tell them the company was good or bad. She was clear that she could not predict that. What she did was ask questions they had skipped.
“Sana, if you find a flat next year and need your share for the down payment, how would you get it out?” Sana had no answer. “What happens to the group if this takes several years to become sellable?” Silence. “If this one holding fell sharply, would all three of you still be comfortable with the friendship and the portfolio?” Rohan laughed nervously.
Her view was simple: the opportunity itself was not something she could judge, but putting most of a shared pot into a single, hard-to-sell position did not seem to match the very different timelines in the group. She suggested they think about the size of the position, not just whether to buy it.
Handling two opinions that didn’t match
Rohan still believed in the company, and that was fine. Meenal’s view and Rohan’s view were not really in conflict about the brand; they were about how much risk the group could carry in one place. Once the team saw it that way, the disagreement got a lot calmer.
They went back to their own Sunday call with both views on the table and asked themselves three things:
- Where did Rohan and Meenal actually agree? (Both thought the company sounded interesting.)
- Where did they differ? (On how much of the pot belonged in it.)
- What did each of the three of them need from this money, and when?
In the end, they agreed on a much smaller allocation, which Rohan and Sana funded mostly from their own share, while Nikhil stayed out. The index funds stayed put. Our article on classic errors new investors make before committing money lists going too big on one idea as a frequent trap, and the trio realised they had nearly walked straight into it.
A quick idea borrowed from medicine
Meenal told them afterwards that she thinks about these reviews the way patients think about a second opinion before a big operation. In healthcare, people can ask an independent specialist to look again at a diagnosis; health sites such as MyMedicPlus, which offers a medical second-opinion service, show how that kind of request is made. Of course, a finance blog cannot comment on any medical finding, and only qualified doctors can. The overlap is just the habit: before an irreversible choice, let someone with no stake look at it once.
What you can borrow from this team
You do not need a group or a fancy adviser to use the same approach. Here is the friendly short version:
- Notice when a move is hard to reverse. Illiquid assets, big lump-sum switches, long lock-ins and leveraged positions all qualify.
- Pause when you feel most excited. Certainty and urgency together are a good signal to slow down.
- Find someone with nothing to gain. Not the seller, not someone who already owns it, not your most enthusiastic friend.
- Bring your whole picture. Goals, timelines and current holdings matter as much as the opportunity itself.
- Ask one clear question. It keeps the conversation honest.
- Treat a different view as information. Work out where the views agree and differ before deciding.
If position size is the piece you want to think about more, our explainer on weighing potential gain against potential loss is a handy next read.
Where they are now
The trio still runs its Sunday calls. They added one new rule to the spreadsheet: any decision that would be hard to undo gets an outside look before anyone presses buy. Nikhil jokes that he is now the official “wait” person. Sana says the rule has already saved them from one more impulsive idea. And Rohan? He is still hopeful about that brand, just with a much smaller slice of the pot riding on it.