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How a small startup climbed a huge Sequoia
Translation of my classical post from a year ago. A story how we were raising from Sequoia for Suggestr—my first startup based in Singapore doing AI Personalization for Shopify stores.
Disclaimer: None of this is confidential, but to avoid tricky questions, consider it a figment of my imagination, and any coincidence with real people accidental
It all began six months ago, before we even got an investment from EF (our alma mater), and had no product, no money, and no company. A Sequoia analyst somehow stumbled upon us (Singapore is a small country), and we even pitched the principal, but it was too early and they decided to "stay in touch." Next, there were four long months of development, growth, us sending monthly updates, and my co-founder Adi impatiently waiting for any response for weeks.
In the meantime, we began to gather forces from the front of our angels. Adi's ex-co-founder introduced him to a friendly analyst at a local fund, who introduced us to someone named Pupa. Pupa, not being a fool, decided to invest in us, and brought along his friends—Pipa, Pepa, and Lipa (a guy well-known in the e-commerce ecosystem). The first three were co-founders of a startup that went through Sequoia’s accelerator, and the best intros, as you know, come from portfolio founders. For this single purpose, we brought all three on board, while Lipa we wanted to bring anyway.
Around the same time, another angel, let’s call him, Kiki, who knows one of the partners at Sequoia, joins us. He’s going to play an important role later.
Meanwhile, through another acquaintance, we got in touch with Bobo from Shopify (we were building on Shopify, so it was a big deal and potentially a strong signal), who had previously lived in Singapore and worked with Lipa in a local unicorn. When friends invest, you don't question the deal too much. So, shortly after, Bobo gets approval from the head of the department in Shopify and joins team Suggestr.
Now we have two former top managers from a local unicorn, so it's time to approach their CEO. Meet Tinky Winky—aka the CEO of the local unicorn. Tinky Winky agrees to invest and casually mentions that he’s the only scout in the region for Sequoia’s pre-seed fund and they follow all his investments. To say that we were open to the idea of them coming alongside would be a huge understatement, we were super excited!
Now, enlisting the support of these beasts, prepared intros, and a pre-seed fund on board, we were ready to raise.
Next, events unfold rapidly:
Tinky Winky makes a referral to the Sequoia accelerator.
Angel Kiki makes an intro to a partner from Sequoia.
Tinky Winky also makes an intro to the same partner. The partner works with Tinky Winky’s company in the fund, so his intro is particularly strong.
Both intros come in the partner's inbox on the same day 🤦♂️🤦♂️🤦♂️ (Are you f-ing kidding me)
The mentioned partner connects us with a new analyst, Adi takes the call (1 out of 3).
Our old friend Pupa randomly decides to tell another partner from Sequoia about us.
This new partner says that they already have a meeting scheduled with us for the next week. We hear about this meeting for the first time (!)
In the end, the analyst whom we had been waiting for a response from for weeks writes to us himself and offers to meet.
Meanwhile, the ex-Sequoia partner who had been focusing specifically on Shopify apps gives us feedback on our deck and our pitch, particularly on how they would want to see it. We revise it. (We know him through a friendly Shopify dude from a random LinkedIn connection).
Adi takes the call with the principal (2 out of 3).
Sequoia wants to conduct due diligence. We gather contacts of 6 (!) clients for them, including 2 who have already churned (!) They call them all.
Meanwhile, we get an invitation to a YC interview, and while preparing casually mention it to our friends.
On the day of the YC interview, I also have to go through the technical due diligence with Sequoia, and describe deeply our architecture and system design.
We get the results of the YC interview (accepted 🎉), and immediately decide to take less money and increase the valuation.
Due diligence is complete, we are in YC, that's it, well played, next week is the final meeting.
Unexpected negotiations begin. They call on Saturday, they call on Sunday. "Can you raise more, can you lower the valuation, look at YC's valuation, let's follow that." In short, we suddenly got pushed into an uncomfortable position, all because of the amount that means nothing for a fund of such size.
We take the last call without much enthusiasm. After, I tell Adi "you looked kinda tired," to which he replies, "yeah, not my best performance."
The result you know, we went sideways.
The wheel of Samsara made another cycle…
The life of a startup is long, and this was just the beginning. We eventually closed the round but had no more energy or time left for games alike. We did our best, and regret nothing.
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