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Many are called, few are chosen

‘Many Are Called, But Few Are Chosen’

No, we’re not talking about admission to Clubhouse in this week’s exclusive.

We’re talking about perhaps the best-kept secret in VC.

The man behind fintech Unicorn Carta’s near $500mm in venture funding raised.

Teetotaler; faintly-Scottish-brogued Brexiteer; family man; lover of a tall glass of milk -

this week’s issue is about none other than Sumeet Gajri.

At Carta, Sumeet wore many hats; strategy operator, LP, principal investor, and advisor. One might go as far as to call him the Chief Fundraising Officer for the Silicon Valley firm.

Perhaps due to the overwhelming stack of hats, Sumeet is also famous for only ever wearing one shirt. (hint: it’s not a black turtleneck.)

Sumeet (right) in his fundraising uniform. source: Twitter

Sumeet (right) in his fundraising uniform. source: Twitter

Sumeet’s classic attire is a purple and neon green Nike t-shirt with the scripture phrase, “Many Are Called, Few Are Chosen”, a cheeky nod to King James of Los Angeles himself, as well as a verse from The Book of Matthew 22:14 from the bible.

A self-described believer (and Lakers fan), the phrase emboldened across his barreled chest, much like the man, is an enigma.

In this week’s exclusive, we’ll explore his background, successes at Carta, and what’s next for Sumeet.

Background

Enter Sumeet.

Founder and GP of Original Capital and scout for Sequoia, Sumeet’s pièce de résistance to date has been shepherding Carta, the Silicon Valley darling helmed by Henry Ward, through several monster rounds of financing.

According to his LinkedIn, Sumeet’s story begins with humble origins.

From 1999-2009 in Cranhill, an inner-city housing district in the northeast of Glasgow, Scotland, Sumeet worked as an assistant at his father’s shop.

“[I] [w]as taught the two most important lessons of my professional career - perseverance, and gratitude - by the best boss I will ever have, my Dad.”

From there, Sumeet went on to college at NYU in New York City, studying economics and political science.

Sumeet hardly followed a traditional path into VC. Instead of exiting a company as a founder or early employee, or being independently wealthy, he came across a unique opportunity with a growth equity shop who was willing to give him a shot.

Sumeet cut his teeth in VC in New York, at a firm who would sponsor his visa during the height of the financial crisis to help him stay in the United States.

These experiences would culminate, by way of grit, good fortune, and good timing, with Sumeet becoming Carta’s (then known as eShares) Chief of Staff, reporting directly to the CEO, Henry Ward.

The ‘Beginning of the Beginning’

‘In 2014, a friend shared a deck with me from a small company in Mountain View called eShares Inc. The deck opened by posing a simple question: “What is eShares?”.

I did not have to wait long for the answer. On the next slide, there was a diagram that represented one of the most audacious visions I had encountered in my short career as a tech investor.

In a single slide, Henry Ward had succinctly laid out a multi-decade roadmap that called for financial infrastructure in the US to be rebuilt bottoms up starting in the private markets.’

-Original capital blog post

Fast forward six years and that vision would unfold into one of the most legendary silicon valley unicorns of our time.

From Carta's pitch deck to investors; Circo 2014

From Carta's pitch deck to investors; Circa 2014

Next Chapter

In March 2020, Sumeet stepped away from Carta to focus on his personal portfolio of investments.

Original Capital is, in a sense, the anti-VC; bucking diversification as one of its’ core investment theses.

In fact, here are his investment theses per the website:

Not your typical '1/10 will do' VC source: www.originalcapital.com

Not your typical '1/10 will do' VC source: www.originalcapital.com

How many VCs are truly “return-oriented”? The average VC fund returns about 20% net of fees to investors and allocates risk across tens, hundreds, and in the case of the Sequoias and A16Zs of the world, thousands of bets.

Sumeet only wants winners.

Will that mean he has plenty of doubters? Initially, probably yes.

But what if he gets it right?

Is the paradigm of ‘throwing enough at a wall to see what sticks’ truly a good business model?

The best operators, VCs, LPs, and fund managers, have a hard time repeating outsized successes, and historically rely on a few home runs per fund to make up for a lot of losing investments.

Is the Man in the Purple Shirt on to something?

Only time will tell, but until then, we will be watching closely as Sumeet’s next chapter unfolds.

That’s all for now, stay tuned for next week’s exclusive.

Data Sources: LinkedIn, Crunchbase, AngelList, www.originalcapital.com

The Cap Table is a resource to help you get, and stay, on the capitalization table.

What did we miss? Email us at [email protected]

20VC: Sumeet Gajri, Chief Strategy Officer @ Carta

Check out Harry Stebbings 20VC podcast episode with Sumeet:

thetwentyminutevc.com • Share

What twitter is saying about Sumeet:

TCT Tip of the Week

Founders: beware of the “Option Pool Shuffle”.

Definition: Anywhere between 13%-20% of unallocated employee stock options can be added (in advance) before the VC writes the check in your next round.

What does this mean? In the event of a sale, unallocated option pool shares will be distributed pro-rata, meaning, some of that money will go right back into investor’s (already deep) pockets. Some call this a “backdoor” way of increasing ownership while trying to come off as a pro-company investor.

Takeaway: seriouslyseriously consider how much equity you’ll be allocating each and every round and avoid any unnecessary dilution. If you plan on having a large pool of shares, have a proper allocation plan.

Notable Deals 5/1-5/8

Deal of the Week: despite financial market volatility, Robinhood nabs $280mm Series F, bringing their total funding to $1.2bn

Sponsored by: Felix Gray

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Seed Rounds

Series A

Sponsored by: ProdPerfect

ProdPerfect is a platform that uses live traffic to automatically build, run, and maintain QA testing for web applications.

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Series B

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Series D

Series F

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