The Path to a Yes is 99 No's

Before the first yes, we had to battle a sea of no’s. But every rejection between then and now taught me how the world actually works.

The first local investor I ever pitched looked like a shark.

I do not mean that metaphorically. I mean the man had small, flat eyes set too wide apart, a mouth that turned down at the corners even when he was being polite, and he sat behind his desk in a Rampura office that smelled of cigarettes and stale air-conditioning the way some Dhaka offices have smelled since the 1990s. I had been introduced through a chain of relatives. Aunt’s husband knew his cousin. The cousin had said this uncle “did investments.” I had imagined an office with a glass partition and a coffee machine. What I got was a man in a half-sleeve shirt who started the meeting by asking me how much money my father made, and ended the meeting by offering me five lakh taka for forty-nine percent of the company.

He was not even shy about it. He smiled while he said the number. I remember walking down the stairs of that building afterward and standing on the footpath outside, the heat coming up through my shoes, a rickshaw bell ringing somewhere behind me, and feeling the specific kind of humiliation that comes from realizing the person who just tried to rob you also thought he was doing you a favor.

That was investor number one. There were many after him.

Every Door In Dhaka, Then Every Door On The Internet

I wrote the same email a thousand times in 2015 and 2016. Two paragraphs, a link to a deck, a line at the bottom asking for fifteen minutes. I sent it to every plausible name in Bangladesh I could find. The wealthy families who occasionally wrote checks into businesses. Bank executives who would take a meeting out of politeness. The textile money. The real estate money. The cousin of the cousin who “did investments.”

Most did not reply. Some did. A handful turned into meetings, and the meetings were worse than the silence. An hour in a conference room with a man twice my age who would nod through the pitch, ask one or two questions to be courteous, then explain to me, gently, with sugar in his tea, that money in Bangladesh worked through land and factories and contracts with the government, and not through whatever I had just described One of them took me to lunch at a Gulshan club, fed me biryani, and ended the meal by advising me to find a real job. He was not being cruel. He was being honest about the world he had lived in for thirty years. The world he had lived in for thirty years did not have a slot for the company I was trying to build.

When Bangladesh ran out, I went to the internet. Y Combinator. Rejected. 500 Startups. Rejected. Techstars. Rejected. Seedstars made me a finalist and then cut me on the final round. I applied to every program on every continent with an open form and a half-credible website. Every single international accelerator said no. The rejections came in at three in the morning because of the time zones, and there is a specific loneliness in reading a Y Combinator rejection at four AM on a mattress on the floor of a one-room apartment in Bashundhara, with the dawn azan starting up somewhere outside the window and the sound of the chacha at the tong setting up his stove on the street below.

Airbnb went through the same thing in 2008. Brian Chesky kept the emails. Seven Silicon Valley investors, every one of them credible, all of them passing on what is now a company worth more than the largest hotel chains combined. The investors were not stupid. They were pattern-matching against companies that had worked before, and Airbnb did not match. Neither did we.

The Pitch Is Not A Static Object

Here is what I did not understand for the first year: the pitch is not a thing you write once and read out in every room. The pitch is a living document, and every no is information you are supposed to fold back into the next version.

I started writing down the questions I could not answer. The first month I had ten of them. The second month I had twenty. By the sixth month I had a list of forty questions investors had asked me that had stopped me cold, and I had answers for every single one, because every time a question caught me out I went home and worked on it until it would not catch me out again. My pitch in month twelve had almost no words in common with my pitch in month one. The company had not changed. The pitch had been rebuilt forty times by the people who said no.

The other tactical thing I learned, the one I wish someone had told me on day one, is this: do not start your pitch with the investor you most want to win. Burn it on the investors you do not. Go to the small fish first. The regional accelerators with bad reputations. The angel groups that meet in coffee shops. That rich uncle. Pitch to them. Take the rejection. Take the questions. Take the friction. Use them as sounding boards, because the polished version of your pitch only exists on the other side of fifty bad ones, and you cannot reach the polished version any other way. By the time you walk into the room with the investor you actually want, you will have answered every question in that room a hundred times in rooms that did not matter.

The Grind Does Not End When You Get Big

By 2019, Pathao was the largest tech company in Bangladesh. Two million users, fifty thousand drivers, profitability on a contribution-margin basis, national coverage, household name. By every metric the 2015 investors had said was impossible, we had become the company they had told me to stop trying to build.

And in 2019, when we needed the next round, they said no again.

The pitch was different now. US lawyer. Audited financials. A deck designed by someone who understood typography. Warm intros to every partner at every relevant fund in Asia. None of it mattered. The post-Uber-IPO freeze had killed the appetite for ride-sharing exposure across the region. We pitched Naspers, the South African giant that owned a piece of Tencent. Passed. Tiger Global. Passed. SoftBank when the Vision Fund still had a pulse. Passed. Sequoia India, Lightspeed, funds in Hong Kong and Bangkok and Dubai whose names I have honestly forgotten.

Spotify went through the same thing in slow motion. Daniel Ek spent thirty months between 2007 and 2009 pitching record labels on streaming. Every meeting ended the same way, polite interest, no license. He kept going because outlasting the industry’s resistance was the only move available to him. When Sony finally signed, the others followed within months. The thirty months were not a failure of the pitch. They were the work.

Pipeline, Not Prayer

The mistake many first-time founder makes is treating one investor like the whole company depends on them. You meet someone, you put your whole life into that conversation, you wait two weeks for the email, the email is a no, you collapse. At that pace you run out of money before the first row of your list is finished.

The fix is a pipeline. Hundred names at the top. Thirty take a meeting. Twelve become real conversations. Five go into diligence. Two send a term sheet. One closes. What a pipeline gives you is parallelism. Investor A is in diligence, Investor B is in second meeting, Investor C just took the warm intro, Investor D got prospected this morning. When Investor A drops out, which Investor A will, Investor B has already moved up. No single conversation can kill you.

This is exactly how a good sales team runs against enterprise customers. Same stages, same conversion math, same arithmetic. Founders who came up through sales raise capital faster than founders who came up through engineering, because they have been running pipelines their whole career and the rest of us have to learn it from scratch.

The Only Skill That Matters

Everything I have told you about fundraising is also true about the rest of your life.

It is true of hiring. The best person you ever hired turned you down twice before they said yes, and the next best person you ever hired was someone you almost rejected because they failed the first interview. It is true of sales. The customer who became your biggest account ignored your first nine emails. It is true of dating. The relationship that became your marriage almost did not happen because one of you was about to give up the night before the second date. It is true of friendship. Every close friend you have was, at some point in the early conversation, someone you had to keep showing up for past the moment they could have stayed a stranger.

Every form of success on earth runs on the same engine, which is the willingness to be rejected and to keep going anyway. The people who succeed are not the people with more talent or more luck or richer parents. They are the people who can sit across from a shark in Rampura, walk out humiliated, and email the next investor on the list that same evening. They are the people who can read a Y Combinator rejection at four AM and apply to 500 Startups before they sleep. They are the people who can pitch the same numbers in the seventy-third room with the same energy they brought to the first.

If you cannot do this, the world will sort you into the version of your life that did not require it. Most people accept that sorting. There is no shame in it. There is also no escape from it, because the version of your life that does not require rejection is also the version that does not require courage, and the things that change anything for anyone, your company, your love, your friendships, your sense of who you are, all sit on the far side of someone telling you no.

The yes is the receipt. The work is the grind. And the grind, if you let it, is the only thing that has ever separated the people who get the life they want from the people who get the life that is left.