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Cover image for Don't Die of Heart Disease
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Oct 4

Don't Die of Heart Disease

During my "hiatus" I've been doing research in a variety of different areas that interest me. After a personal experience with basal c...

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Blog iconRide It to the Sky
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The Deal

Founders have little to no diversification. They are all in on one idea, company, and mission. It's an insanely high-risk, high-reward endeavor. As founders become increasingly wary of this level of risk concentration, they begin to think about ways to mitigate it. One idea I've heard repeatedly is the notion that a group of founders can self-assemble and contribute a percentage of their equity in their company to a shared pool. That way, if they fail and one of the other founders in the grou...

Cover image for Sequoia Wants It Hard
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Sequoia Wants It Hard

I have seen a lot of young first-time founders play it fast and loose in their fundraising processes the past several years. It’s been frothy times, so I think it brings out a lot of strange behavior. It got me thinking of when I was a young founder and the things I’d do, particularly one specific story that I tell people when I get asked “what not to do” when fundraising. Back in 2010 Steve and I launched GroupMe to much fanfare. It got a lot of attention out the gate because we built it at ...

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Search...Ctrl+K

Ride It to the Sky

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More from Ride It to the Sky

Cover image for Don't Die of Heart Disease
Blog iconRide It to the Sky
Oct 4

Don't Die of Heart Disease

During my "hiatus" I've been doing research in a variety of different areas that interest me. After a personal experience with basal c...

T
Blog iconRide It to the Sky
Nov 22

The Deal

Founders have little to no diversification. They are all in on one idea, company, and mission. It's an insanely high-risk, high-reward endeavor. As founders become increasingly wary of this level of risk concentration, they begin to think about ways to mitigate it. One idea I've heard repeatedly is the notion that a group of founders can self-assemble and contribute a percentage of their equity in their company to a shared pool. That way, if they fail and one of the other founders in the grou...

Cover image for Sequoia Wants It Hard
Blog iconRide It to the Sky
Jul 15

Sequoia Wants It Hard

I have seen a lot of young first-time founders play it fast and loose in their fundraising processes the past several years. It’s been frothy times, so I think it brings out a lot of strange behavior. It got me thinking of when I was a young founder and the things I’d do, particularly one specific story that I tell people when I get asked “what not to do” when fundraising. Back in 2010 Steve and I launched GroupMe to much fanfare. It got a lot of attention out the gate because we built it at ...

View more

2025 Paragraph Technologies Inc

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Ride It to the Sky

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