Luck favours the brave: how Shayan Mahmud built three companies

Three companies, one operator

The episode opens with Muzamil introducing a guest he has been trying to get on the show for years — Shayan Mahmud, a friend of nearly five years and one of the few people in Islamabad simultaneously running a creative agency, a B2B export business, and a publishing house. The titles stack up quickly. CEO of Icon Seven. CEO of TradeMore. Chief brand officer and managing partner at ProPakistani. Muzamil reads them out almost as a joke, then asks Shayan to explain what each of them actually does.

Shayan walks through it patiently. Icon Seven is a full-service advertising agency with offices in Islamabad, Bucharest, and Dubai — production, web, app development, and design across the three. TradeMore is the channel partner for Alibaba’s B2B business in Pakistan, helping local manufacturers list and trade globally. ProPakistani is the third — “Pakistan’s largest online independent publisher,” he calls it, with roughly seventeen million in monthly traffic, over a hundred employees, and coverage that has now expanded from tech and telecom into food, auto, business, and entertainment. The pieces look unconnected on a slide. The thread underneath is how Shayan thinks about luck, timing, and team — and that thread is what the rest of the conversation follows.

The Nanjing year

Before the businesses, there was a detour through China. Shayan grew up in Islamabad — Froebel’s from the start, “born and bred” — went to the UK for university, failed out of his first bachelor’s, and was told by his father that if he wanted to continue, Mandarin had to be part of the package. He landed at the European Business School and spent one year of his degree in China.

He did not pick Beijing. His friends were heading to Hangzhou. Shayan applied to Nanjing — a city of seven million that, by Chinese standards, was small. He showed up two months early because the acceptance letter was in Chinese and nobody translated the dates. For those two months he saw exactly one other foreigner — chased him down in a supermarket asking for his phone number. He watched TV shows, played football with locals, and tried to teach a Chinese girl Hindi while she tried to teach him Mandarin.

What he took from the year was less language than perspective. “In 2012, everything was cash on delivery,” he tells Muzamil. “Just like Pakistan.” He was carrying RMB in his pocket; eight years later, the entire country runs on WeChat payments. When Pakistani founders argue fintech can’t take off here, that timeline is the data point he keeps returning to. The Chinese, he says, are masters of propaganda — not pejoratively, just descriptively — and “the Chinese love it,” which is why it works. The infrastructure, the transportation, the ability to move that many people through that many cities — to him it reads as “an art.”

The Munna Bhai launch

Shayan came back to Pakistan in December 2014. The original plan had been film. He had interned in Bucharest on a B-list Hallmark-style production at a place called Castov Studios, where he was waiting for Azaan Sami and Jami to arrive for the post-production of Operation O21. That is where he met Gabi — a Romanian fifty-something who became his business partner through a mutual friend and a shared World Cup.

When O21 needed a marketing agency, Shayan brought Gabi in. The film underperformed. The next film he was supposed to work on collapsed. So he picked up the phone in his last semester at university and pitched a different idea — open an agency in Pakistan together. Gabi said yes.

The launch itself, Shayan tells Muzamil, was pure Munna Bhai. He hired Talha — now his partner at TradeMore — and Hassan, who still runs digital. He revamped his grandparents’ downstairs apartment as a fake office, brought in random friends as fake staff, and was halfway to the team meeting in a panic when he realised Gabi hadn’t even woken up from his late-night airport arrival. Eight or nine bodies were in the room when the Romanians walked in. They liked what they saw. Bad Cat in Romania was shut down. Icon Seven Bucharest opened in its place.

What worked, he insists, was not strategy. It was the first six hires. “I was very lucky,” he says. “We got a really good team early. Talha runs TradeMore. Daniyish runs production. Maria runs creative. Hassan runs digital. They were all really good, and fresh out of college, and they enjoyed building something together. That sort of survival just kind of snowballed from there.”

What the agency business actually costs you

Muzamil pushes on the agency market itself. Islamabad in 2014 was not Lahore or Karachi — there was no obvious creative-services pipeline to plug into. Shayan remembers the first pitch with unusual clarity. An insurance company, now defunct. “The biggest budget I could think of was, like, three or three-and-a-half lakh rupees.” Most of what bought Icon Seven its footing was serendipity — early contracts with Pakistan Tobacco and a handful of similar clients.

But the honesty in this stretch of the conversation lands harder than the romance. Asked whether he would start an agency again, Shayan is unequivocal: “Of all the businesses I’m involved in, advertising is the most difficult. It’s very, very hard to run an agency, and I would never want to do it again.” The reason is the clock. Digital has made the work real-time. A trend is happening now. Tomorrow it might still be happening. The day after, it is gone. Clients aren’t to blame — the medium is the message — but the operating tempo is brutal.

Muzamil reinforces the point with a memory from his own small business: most of the online buying came in between midnight and seven in the morning, instinctive purchases made from bed, not from any retail funnel a 1990s agency would recognise.

TradeMore, four-time team resets, and Pakistan as the world’s number-two

The TradeMore origin story has a similar texture. An acquaintance at the embassy in China told Shayan that Alibaba was looking for Pakistan partners. He, Talha, and Hassan put together a bid in a couple of nights. Three months later, the call came back. They passed the tests and signed on.

The first two years, Shayan tells Muzamil bluntly, were a disaster. “We changed teams four times. We ended the whole team completely four times.” On Alibaba’s model, you don’t earn commission on a sale until specific milestones are hit; the gap between effort and reward is wide enough to kill morale. “You work harder when things aren’t working,” he says. “You stress more, you think more, you sit with the team more, you stare at the numbers more. And then when the transition came — when we became their number-one partner in the world for the last two quarters — I can’t tell you what we were doing differently. I think we were just doing more of it on time.”

The reframe inside TradeMore was geographic. The early team had been selling Alibaba to TradeMore prospects the way they sold Icon Seven — pitching from Islamabad. That stopped working until they accepted that TradeMore’s customer was in Sialkot, Faisalabad, Wazirabad, Gujranwala, Multan. “Their grandfathers used to make swords and guns,” Shayan says. “Obviously that market isn’t what it was, so they pivoted into cutlery. Pakistani cutlery from Wazirabad is really good. Pakistan is a goldmine of unique things like this.”

The number he drops in passing is the one most listeners will remember. According to Alibaba’s regional head, who was in Pakistan that week meeting government officials, “Pakistan is the number-one supplier-side market in the world after China — more than India, more than Bangladesh.” He attributes it to three things: price competitiveness, quality (leather, salt, manufactured goods), and timing.

The blockage, Shayan admits, is data. Alibaba doesn’t have enough. TDAP doesn’t have enough. And the manufacturers who do know — the ones selling motorcycle gear on Etsy at fat margins through DHL — refuse to share what they’ve found. “It’s an old-school mentality,” he says. “And it has to change. We grow when the industry grows.”

Joining ProPakistani — and what publishing actually pays for

The ProPakistani chapter starts with Shayan wanting to make videos about people. He had stumbled into a content gap in his own life — when he was starting out, there was nowhere to learn what other founders had figured out. He pitched a small video project. The publisher’s founder, Aamir bhai, made him a different offer: come in as a partner. Take more of the shareholding. Bring investors. Shayan called his TradeMore partner Gabi, framed the opportunity, and got the cheque. “Sometimes if you keep going after one thing, doors open on their own.”

Muzamil challenges him head-on with the bear case. Publishing is hard. AI is coming for copy. The space is fragmented. Huffington Post bled cash for years. New-age digital publishers around the world either pivoted into subscriptions or died. How does ProPakistani avoid the same fate?

Shayan’s answer is the most operationally interesting part of the conversation, and worth quoting at length. ProPakistani, he says, took the opposite route to most of its peers. “They went the funding route. They weren’t cash-positive. They were trying to displace the larger players. We’re not doing that.” ProPakistani is significantly profitable. Profits roughly doubled in the last year. COVID was the worst year and it still grew. The reason, in his telling, has very little to do with content and a lot to do with money discipline. “The difference between us and the publishers in our space who didn’t make it is the ability to monetise and the ability to stay frugal. Most of our clients are retainer clients. We sign annual contracts. First of the month, we get our cheque. That’s how it works.”

The retainer model removes the cash-flow problem that buries content businesses. It also serves the client better — a single PR push doesn’t shape public opinion; sustained, multi-format presence does. Aamir bhai, he says, was unusually clear about that science from the first day they met.

Ali, eye-tracking, and why Pakistani advertising is stuck in the seventies

Later in the discussion, Muzamil flags that Ali Elias — a past guest of the podcast — has joined Icon Seven. Shayan confirms it and uses the hire to make a broader point about where Pakistani advertising is still underdeveloped.

Ali is bringing in disciplines that Pakistani agencies rarely use — menu reengineering (on the second-most-expensive item, the one people actually buy), focus groups, eye-tracking glasses that record what the eyeball is doing as opposed to what the customer thinks they noticed. Shayan shares one example. An NGO had used the same poster image for years. Everyone on the team loved it. The focus group came back and said they would not donate after seeing the picture, because it made them feel bad about themselves. The single piece of creative the organisation had been most attached to was the thing actively repelling donors.

Muzamil’s contribution to this section is a memory of a restaurant with an undifferentiated washroom — same flush, same urinal, same door, no signage — that confused a woman into walking out and choosing the other one. “Such a basic design failure,” he says. “Design theory and consumer psychology are things we just aren’t integrating into our lives in Pakistan.”

Shayan finishes the thread bluntly. “Most people in Pakistan are still advertising like it’s the seventies. Make one campaign. Push it for six months. See what happens. And when you ask them what the result was, the answer is nothing.” The fix is process — A/B tests, multi-channel orchestration, treating customer data as the asset it is — and the holdout is mindset, not capability.

Timing, failure, and the only honest answer about luck

Toward the end, Muzamil and Shayan converge on the question underneath everything they have been discussing: how much of this is skill, and how much of it is luck?

Shayan doesn’t dodge it. “When someone is mildly successful, people look at it and say, what is this guy doing, things just keep working out for him. You don’t see how many things I’ve tried that didn’t work.” The mentality he keeps coming back to is the one about missing a hundred shots and continuing to shoot. “If you have that in you, life is generally easier.”

He layers a second observation on top. Most businesses, he says, are either too early or too late. “Very few people make the perfect thing at the perfect time. Aamir bhai started ProPakistani in college. Tech blogs weren’t a thing yet. One-man show for four or five years. Then he started hiring. Look at it now.” Muzamil’s contribution is the local example everyone in Islamabad knows — Burning Brownie, which started as a tiny stall at a Shell petrol pump and grew into Beverly, F-11, DHA, the ice cream place, an empire.

The closing exchange leans optimistic. Shayan, asked how he sees Pakistan in thirty years — when he will be sixty and “at the prime of your power, as per the current system” — says he is genuinely hopeful. “I have a British passport. When I told my friends in 2014 that I was moving back, they thought I was crazy. I told them I think in ten years Pakistan will have a big wave, and I’ll be riding that wave.” He doesn’t claim to be able to predict the future — “people much more intelligent than me can’t predict the future, what am I going to do?” — but his emotional belief is firm: if twenty crore people try their best and stay, the country gets where it needs to go.

Muzamil signs off with the line he keeps coming back to with founders. “Optimism, hope — it’s the most powerful weapon in the world.” Three companies, three hundred employees between them, and the thing he wants to register on tape about Shayan is not the scale. It is the humility.