A few weeks ago I spent two weeks evaluating a startup. It didn’t convert into something substantial.
Company was good. Founders were sharp. It ended because when it came to the numbers, the company put its interests first. And I put mine first too. Those two things didn’t overlap.
What happened in between is worth writing about.
The anchor problem.
The founder who reached out had worked with me years ago. Different company, different time, different version of me.
He remembered me at a certain career stage. A certain salary band. A certain level of seniority. That’s the anchor he built the conversation around, even if he never said it out loud.
By the time we got to compensation, he made an offer that was generous relative to who I was when he last knew me. It wasn’t generous relative to who I am now.
The gap wasn’t bad faith. It was outdated information. And here’s the part I have to own: I let that outdated picture sit uncorrected for two weeks. I answered his questions, explored the role, went deep on the product and the market, had multiple conversations. I did everything except establish, early and clearly, where I actually stand today.
When you reconnect with someone from your professional past, they are meeting a memory of you. Not you. If you don’t update that picture in the first conversation, you will negotiate against a ghost of yourself for the rest of the process.
That’s not on them. That’s on you.
The gap between what founders describe and what the product does.
The founder explained the vision clearly. Accessible, logical, almost simple.
I came off the first call thinking I understood the product.
Then I used it.
What he described was the product at its destination. What existed was the product at its current address. Those are two different places, and the distance between them is not a flaw. It is the job. It is exactly what an operator joining at this stage is supposed to close.
But here’s the problem: if you don’t use the product yourself, you will spend weeks evaluating a company based on a version of it that doesn’t exist yet. You’ll fall in love with a pitch. And pitches don’t have rough edges.
The product had rough edges. The onboarding assumed you already knew what you were doing. The most natural question a new user would ask, the one any normal person would type first, the product couldn’t answer. The placeholder query returned zero results.
None of this was a dealbreaker. All of it was visible only because I used the product instead of just listening to someone describe it.
Use the product. Always. Before the second call. Before you start getting excited. The gap between the vision and the current reality is the most honest thing a company will ever show you.
How India misprices people who’ve worked across functions.
There is a category of operator that Indian startups consistently underprice. Not because they’re unaware of the value, but because there’s no clean title for it.
These are people who’ve run GTM and also fixed the hiring process. Who’ve built the product roadmap and also managed the investor update. Who’ve done things that belong to four different job descriptions because the company needed it and they were the person who could see the whole board.
When a startup tries to hire this person, they reach for the nearest available label. Growth. Generalist. Bizops. Each of those labels comes with a salary band. Each of those bands was built for someone doing one of those things, not all of them.
The result: the person with the broadest capability gets offered the narrowest compensation. Because the market doesn’t have a price for “someone who can hold the whole non-engineering surface of a 7-person company together while the founders build.”
The offer I received was not unreasonable for the label they used. It was significantly below what the actual scope required.
And here’s the thing I keep coming back to: the company was right to put its interests first. They have a runway, a burn rate, a team to pay. They offered what they could sustain. That’s not wrong. That’s how companies survive.
The mistake would have been accepting it anyway because the opportunity felt exciting and I didn’t want to lose it.
Companies optimise for their survival. You have to optimise for yours.
What I’m taking away from this.
I understand a space I didn’t understand before. I have a sharper view of how AI is being layered into Indian financial products, what the competitive landscape looks like, where the real moats are versus where founders think they are.
I know my floor more clearly than I did two weeks ago. Not as a number I say in negotiations, but as a number I’ve actually calculated from first principles. What a city move costs. What career risk is worth. What I’ve built since the last time someone in my professional past knew my salary.
And I know that no matter how genuinely good an opportunity feels, the company will put itself first when the stakes are real. It should. That’s how companies work.
So should you.
