Mistake #3: I Was Writing for the Wrong Room
This is the third post in a series about the mistakes I made starting up, and what I’d tell myself if I could go back.
For the first few years of building, I had a mental editor sitting on my shoulder every time I opened LinkedIn.
Not a real person. A composite. A blur of faces from my Microsoft years: colleagues, managers, peers from across the org. Smart people. People whose opinions I respected. People who had nothing to do with what I was building.
And I was writing for them.
The Setup
I spent over 11 years at Microsoft. Nearly all of my post-college friendships were formed there. When I came back to Hyderabad in 2017 to do my MBA and start building, I didn’t leave that world cleanly. It came with me: in my contact list, in my LinkedIn network, in my head.
So when I sat down to write a post about something I was learning, or a take I had on the market, or something unconventional I wanted to try, the question that surfaced first was: what would X think of this? What would Y say?
X and Y were not my potential customers. They were not founders figuring out similar problems. They were engineers and product managers at one of the largest software companies in the world, looking at a former colleague who had gone off to “start something in India.”
I was optimizing my message for people who were never going to buy what I was selling.
What Optimization for the Wrong Audience Actually Looks Like
It is subtle. That is what makes it hard to catch.
It does not mean you write badly. It means you write safely. You pick angles that feel respectable rather than angles that feel true. You avoid takes that might read as desperate, or naive, or too salesy, or too raw.
You stay legible to people who already know you, instead of becoming findable to people who need to find you.
Every time I tried something different, a more direct take, a more vulnerable post, something that felt genuinely useful to an early-stage founder or a business owner exploring AI, the DMs would come. Old friends from Microsoft. Sometimes encouraging. Sometimes curious. Occasionally skeptical.
And my brain would register that as signal. People noticed. People responded. Keep doing this.
But those people were not the signal I needed. They were comfortable noise.
The posts that reached actual potential customers, that got shared in circles I had no visibility into, that led to someone reaching out about a real business problem. Those looked different. They felt different to write. More exposed. Less polished. More direct about the specific pain I was trying to solve.
I wrote fewer of those, for longer than I should have, because they made me uncomfortable in front of the wrong audience.
The Deeper Problem
When you come from a large company, especially one with a strong culture like Microsoft, you internalize a certain standard of how a professional presents themselves.
Measured. Credible. Not too promotional. Thoughtful about optics.
Those instincts are not wrong inside that context. Inside a large organization, managing perception across a complex stakeholder map is a real skill that has real value.
Outside it, as a founder trying to find your first hundred customers, those same instincts become a handicap.
Your potential customers do not care about your optics. They care about whether you understand their problem. The fastest way to demonstrate that is to talk about it directly, specifically, and without the careful hedging that reads as professional in a corporate context and reads as vague in a founder context.
I knew this intellectually. I had read enough about founder-led content to understand the theory. But theory does not override the discomfort of posting something raw and knowing that your former skip-level manager might read it over their morning coffee.
What Actually Changed
It took a long time. And it was not a single realization. It was a gradual loosening.
Part of it was simply time. The further I got from Microsoft, the less that mental editor had authority. New connections started to outnumber old ones. The feedback I was getting from posts started to come from people who were actually in my world: founders, business owners, operators. Rather than people who were curious about what I was up to from a previous life.
Part of it was watching what actually worked. The posts that performed, not just in likes but in conversations that led somewhere real, were consistently the ones that ignored the composite editor on my shoulder.
Part of it was accepting that the discomfort was not a warning signal. It was a calibration signal. If a post felt uncomfortable to publish, it usually meant it was saying something true and specific, which is exactly what it needed to say.
You are not writing for the audience you have. You are writing for the audience you need.
Those are different people. And until you accept that, every post is a compromise between the two.
What I’d Tell Myself Now
Your LinkedIn network at the start is a historical artifact, not your target market. The connections you have reflect where you have been. The connections you need reflect where you are going. Optimize for the second group, even when the first group is louder.
DMs from old colleagues are not product validation. Engagement from people who already know and like you is warm and real, but it tells you nothing about whether strangers will find you relevant. Track the responses from people you do not recognize. Those are the ones that matter.
The posts that feel most exposed are usually the most useful. The instinct to soften, qualify, and hedge comes from a corporate context where those things protect you. In a founder context, they obscure you. Say the thing directly.
Write as if your best potential customer is reading, not your former manager. This sounds simple. It is not. But it is the right frame. Every post is an audition for the customer you want, not a performance review for the career you left.
Eight Years Later
I still occasionally feel that old pull. A thought before hitting publish: what would someone from my Microsoft days think of this?
It comes up less now. The network has shifted. The context has shifted. And I have enough evidence from posts that worked, that found the right people and started the right conversations, to trust the discomfort more than the caution.
But I wasted real time getting here. Years of posts that were competent and forgettable. Years of playing to a room that was never going to become my business.
The room you are writing for shapes everything you write. Make sure you know which room that is.
The bottom line: Early-stage founders who come from large companies often carry an invisible audience in their heads: former colleagues whose approval they are still, unconsciously, seeking. That audience is the wrong one. You need to write for the people who do not know you yet, which means being specific, direct, and comfortable with being uncomfortable.
Who are you actually writing for when you post? I would genuinely like to hear how others have navigated this.
I’m Gopi Krishna, founder of Hyperleap AI, where we build enterprise-grade conversational AI but for Small and Medium Businesses. This is part of an ongoing series on the mistakes I made in my first years as a founder, written for anyone thinking about starting something of their own. Subscribe to Second Order AI on Substack to follow along.