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Angel Investor (Individual)
wlessin.com

Investments

17

Portfolio Exits

6

About Sam Lessin

Sam Lessin is a New York-based angel investor who typically investsupto $100K in young companies. Lessin prefers to invest in very early stage New York and San Francisco-based companies with a technical founder. He aims to add value to portfolio companies with product input and introductions. Lessin is also the co-founder of Drop.io in August 2007. He invest in very early stage companies with technical founders primarily in New York and San Francisco. He does not invest in social media or advertising plays. He aims to provide value to his portfolio companies through relationships/network and product input.

Headquarters Location

New York, New York,

United States

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Latest Sam Lessin News

Creators raising venture capital: unsettling or genius?

Oct 12, 2023

When Slow Ventures announced that it would set aside $20 million to invest in individual creators, GP Sam Lessin responded to onlookers’ confusion with a memorable quip: “it’s def not indentured servitude.” Though Lessin’s remarks weren’t very reassuring, these sorts of venture deals – investments in people, as opposed to companies – have started to seem a little less bizarre. Companies like Spotter and Jellysmack underwrite YouTubers’ back catalog in exchange for upfront cash, while Creative Juice will fund a creator in exchange for a cut of revenue over a set term. Mythical, the entertainment studio owned by YouTube stars Rhett and Link, launched a $5 million venture capital fund for creators in 2021. That same year, Slow Ventures made a deal with Marina Mogilko , a language learning YouTuber and co-founder of the platform LinguaTrip. In exchange for $1.7 million in capital, she will give the venture firm 5% of her earnings for 30 years – plus, they keep that 5% stake in any IP she develops within those three decades. As she explained to VICE , “If I wrote a book in 2030, and it’s still selling in 100 years or whatever, they’re still getting 5 percent of that revenue.” According to Slow Ventures principal Megan Lightcap, the firm has inked six or seven deals with creators thus far, and hopes to close a few more before the end of the year. Two years ago, when the firm wrote a check to Mogilko, this practice seemed intimidating at best, and predatory at worst. “Honestly, with any seed stage investment, it’s risky,” Lightcap told TechCrunch. But investing in human beings as opposed to companies creates extra barriers, legal concerns and moral considerations. “A portion of our creators may wake up in five years and be like, ‘No, I want to go to law school.’” And if a Slow-backed creator did decide to go to law school, they wouldn’t pay any penalty to the venture firm. These deals don’t require that creators remain on their YouTube grind forever, but Lightcap explains that this flexibility is why the firm structured deals to persist over decades. “The way we keep the cost of capital low is to be deeply aligned with the creator over the long term,” Lightcap said. “We want to be able to say that in year seven or whatever, if they launch a really interesting company and it takes off and that’s where the value is, we need to be able to participate in that upside to keep the cost of capital inexpensive.” Both Slow and Mythical are particularly interested in creators with an entrepreneurial bent. Lightcap says she’s looking for the next Steve Rinella – the multi-hyphenate creator behind the MeatEater series – as opposed to the next iconic lifestyle vlogger. “We want to back creators that have multiple ideas and want to be a little more risk-on, and to have more at bats, versus, say, just making a couple of hires and generally investing in content,” Lightcap told TechCrunch. From a venture standpoint, creator businesses might even be more appealing than an early stage startup, since creator businesses will almost always be profitable by the time they’re big enough to catch a firm’s eye. Creators generally work toward profitability from day one, whereas it’s normal for even a late-stage startup to be losing money. Slow isn’t public about most of the creators it’s investing in, nor the terms of their deals. But Mythical is publicly backing Jarvis Johnson , Daniel Trasher and The Sorry Girls . Mythical also wouldn’t share how much capital these creators got, but their total fund is $5 million and hasn’t been fully spent yet, so we can make a guess. These creators are likely getting about $1 million in capital, whereas last year, YouTube sensation MrBeast was rumored to be shopping for a $150 million check at a $1.5 billion valuation . That doesn’t mean Mythical’s creators are small potatoes, though. Each of these three YouTube channels have more than 2 million subscribers – such popular channels can sometimes make more than $50,000 per month off of ad revenue alone. Mythical is a wholly independent studio owned by Rhett and Link , which has raised no outside capital or debt. “It’s independently financed, which gives us a lot of freedom and flexibility in our investment style,” said Neel Yalamarthy, Mythical’s SVP of strategy. “We don’t have rigid timelines or targets, though we want all of our investees to grow and build companies that one day could become the size of Mythical, or even greater.” Though the entertainment industry as a whole has suffered from decreased ad revenue, Mythical looks toward these investments as a way to embrace the changing media landscape. “A great example is the Sorry Girls, and how they’re working to create content that’s akin to HGTV, but for digital audiences, or Daniel Thrasher, who is very much in the Bo Burnham lane, or Jarvis Johnson, who we think is comparable to Jon Stewart and The Daily Show,” Yalamarthy told TechCrunch. Mythical is thinking more about how they can invest in a creator to build something akin to a TV channel, while Slow is looking toward e-commerce and apps. Lightcap believes creators are more well-positioned than traditional brands to sell a variety of products while remaining authentic. “Think about Lola, or any of these next-gen tampon companies,” Lightcap told TechCrunch. “If they were to launch supplements, it’d maybe feel a little weird and disingenuous to customers, whereas if you have a creator broadly in the women’s health space, they can launch a whole bunch of different products.” Slow and Mythical seem to be doing well thus far, though it’s still early for their creator investments. But the question remains: Is it ethical to treat a human being like a company and make a deal encompassing all of their potential IP? And is it beneficial for venture funds to underwrite people anyway? If a startup founder is caught doing something awful, they can usually leave and the business may eventually recover. But people are different. Amid allegations of a sexual assault that occurred on his filming set, YouTube star David Dobrik stepped down from Dispo, the photo app that he co-founded. Three venture firms that invested in Dispo – Spark Capital, Seven Seven Six and Unshackled Ventures – severed ties with the app, some promising to donate any possible profits from their investment to organizations helping survivors of sexual assault. Then again, even “canceled” creators can still maintain an audience. Despite an additional controversy about a near-fatal accident on Dobrik’s set, the 27-year-old remains on the map. He runs a pizza shop in Los Angeles, and he’s one of the top creators on Snapchat. At the end of the day, if something were to go horribly wrong, these firms are only out a few million dollars. In the world of venture, that’s a drop in the bucket. “Maybe we’ll see a person IPO one day,” Lightcap said.

Sam Lessin Investments

17 Investments

Sam Lessin has made 17 investments. Their latest investment was in Glean AI as part of their Seed VC - IV on September 9, 2023.

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Sam Lessin Investments Activity

investments chart

Date

Round

Company

Amount

New?

Co-Investors

Sources

9/5/2023

Seed VC - IV

Glean AI

$4.9M

Yes

6th Man Ventures, Slow Ventures, South Park Commons, Spartan Group, Undisclosed Angel Investors, and Undisclosed Venture Investors

2

8/30/2021

Seed VC

Clay

$8M

Yes

1

1/9/2021

Pre-Seed

Every

Yes

2

6/25/2019

Series A

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$99M

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10

1/5/2018

Seed VC

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$99M

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10

Date

9/5/2023

8/30/2021

1/9/2021

6/25/2019

1/5/2018

Round

Seed VC - IV

Seed VC

Pre-Seed

Series A

Seed VC

Company

Glean AI

Clay

Every

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Amount

$4.9M

$8M

$99M

$99M

New?

Yes

Yes

Yes

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Co-Investors

6th Man Ventures, Slow Ventures, South Park Commons, Spartan Group, Undisclosed Angel Investors, and Undisclosed Venture Investors

Sources

2

1

2

10

10

Sam Lessin Portfolio Exits

6 Portfolio Exits

Sam Lessin has 6 portfolio exits. Their latest portfolio exit was Anomalie on May 17, 2022.

Date

Exit

Companies

Valuation
Valuations are submitted by companies, mined from state filings or news, provided by VentureSource, or based on a comparables valuation model.

Acquirer

Sources

5/17/2022

Acquired

$99M

2

1/26/2022

Acquired

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$99M

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10

12/12/2018

Acquired

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$99M

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10

5/1/2018

Acq - Fin

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$99M

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10

5/29/2015

Acquired

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$99M

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10

Date

5/17/2022

1/26/2022

12/12/2018

5/1/2018

5/29/2015

Exit

Acquired

Acquired

Acquired

Acq - Fin

Acquired

Companies

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Valuation

$99M

$99M

$99M

$99M

$99M

Acquirer

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Sources

2

10

10

10

10

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