Sean O’Brien

@Gatsby

Inc. 5000 & Shark Tank CEO. Raised $50M w/ 2 exits. VC/PE/RE investor. Featured in Entrepreneur, Inc., TechCrunch, & on TV. @Columbia_Biz @Stanford

Phoenix & Los Angeles

Joined February 2012

84Following

365Followers

Pinned

Sean O’Brien@Gatsby · Mar 31

The golf company i run w/ my 2 partners was just featured on NUCLR Golf after being in Golf magazine last week.

NNUCLR GOLF@NUCLRGOLF · Mar 31

🚨#GOLFERS — Are you looking to cure your slice & prevent topping? ⛳️ Introducing, Swingzy.🏌🏽‍♂️ This patented training aid provides instant feedback on every swing, teaching you how to improve contact & make better strikes. It works w/ irons & woods and won’t damage your clubs.

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Sean O’Brien@Gatsby · Nov 30, 2022

We’ve come a long way.

AAutioApp@AutioApp · Nov 30, 2022

App of the Day (again!) Thanks to our fans for getting us here and helping us make this app what it is. 🙌 We're looking forward to sharing even more stories next year! 🎉

Sean O’Brien@Gatsby · 8 h

If you’re well off, never fly @Delta bc now they charge you more for a ticket based on your success via signals like your job title on LinkedIn.

Sean O’Brien@Gatsby · Jul 10

B & C players need intros. Cold email works for A players.

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Sean O’Brien@Gatsby · Apr 23

Looks like @GeoffLewisOrg will be right again.

SSheel Mohnot@pitdesi · Apr 23

OpenAI now projects $125B in revenue in 2029, with $25B of that from new products not yet announced. If they hit it, the current valuation ($300B) will be a steal; Google does ~$400B in revenue and is worth $2T

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Sean O’Brien@Gatsby · Apr 10

Need more founders like this. @jordihays @johncoogan gotta put this guy on @tbpn

BBrian Riley@thebrianriley · Apr 10

Today, we announced a $19M financing with JPMorganChase to launch the first high-volume bicycle frame manufacturing plant in the U.S. But this isn’t just about bikes—or even just about manufacturing. It’s about a new model for how physical products are built and delivered in…

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Sean O’Brien@Gatsby · Nov 26

The next big scandal will be semaglutide once all the research settles.

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Sean O’Brien@Gatsby · Apr 23, 2024

Very few people still doing real journalism, esp in sports. @JoePompliano is one of those few. Great read here on @Timberwolves saga.

JJoe Pompliano@JoePompliano · Apr 23, 2024

EXCLUSIVE: I've spent the last few weeks investigating the fight for ownership of the Minnesota Timberwolves. Sources provided specific examples of Glen Taylor sabotaging the deal, upsetting limited partners, and positioning himself for a fight. READ: shorturl.at/iFKW4

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Sean O’Brien@Gatsby · Feb 16, 2024

Everyone is trading american equities at peak & i’m going heavy into india & china equivalents of the s&p. Will be interesting to see how these buys look in 30 years.

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Sean O’Brien@Gatsby · Aug 16, 2023

i’m in the process of setting up a fund & i think @rrhoover deserves a gold medal for the content that @signatureblock_ provides. The best resource i’ve found by a mile.

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Sean O’Brien@Gatsby · Jul 19, 2023

This is a fantastic post about QSBS tax savings for startup employees. I recently did a post about QSBS stacking & packing strategies, as well as how GPs can get their 2% mgt fees taxed as capital gains. Your co-founder Alejandro follows me, love what you guys are doing!

AAnkur Nagpal@ankurnagpal · Jul 19, 2023

Everyone talks about the QSBS tax exemption for startup founders and investors But it's also for startup employees! QSBS allows you to pay no federal (and sometimes state) taxes on up to $10M when the company sells Here's how startup employees should be approaching this:

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Sean O’Brien@Gatsby · Jul 3, 2023

Estonia is an interesting combination of the old world yet has a booming tech scene that created tens of billions in value from a small population.

Gatsby's tweet image. Estonia is an interesting combination of the old world yet has a booming tech scene that created tens of billions in value from a small population.

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Sean O’Brien@Gatsby · Jun 19, 2023

How to get your 2% mgt fees as a General Partner taxed at the capital gains rate. nytimes.com/2021/06/12/bus…

Gatsby's tweet card. The I.R.S. almost never audits private equity firms, even as whistle-blowers have filed claims alleging illegal tax avoidance.

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Sean O’Brien@Gatsby · Jun 18, 2023

Founders & VCs… learn how stacking & packing QSBS works for shares. Crazy how much $ is being made tax free. nytimes.com/2021/12/28/bus…

Gatsby's tweet card. Once aimed at small businesses, a 1990s-era tax break has become a popular way for Silicon Valley founders and investors to avoid taxes on their investment profits.

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Sean O’Brien Retweeted

Brianne Kimmel@briannekimmel · Mar 14, 2023

Don't sleep on Arizona, 634 companies have either relocated or expanded their footprints in the state since 2015.

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Sean O’Brien Retweeted

AutioApp@AutioApp · Mar 13, 2023

Do we sound excited? We’re pretty excited. Tune in next Friday to catch all of the on-air action on ABC, or watch on-demand after it airs with Hulu. #AutioOnSharkTank

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Sean O’Brien Retweeted

AutioApp@AutioApp · Feb 8, 2023

We’re excited to announce that our stories are headed to new heights! 🛫 Listen to hundreds of Autio stories 🎧 right on @JetBlue seatback screens. travelandleisure.com/kevin-costner-…

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Sean O’Brien@Gatsby · Sep 29, 2022

The upcoming housing market crash will be nearly as bad as 2007. These numbers are scary. Companies will start laying folks off to boost stock prices, & the supply of housing will skyrocket.

Gatsby's tweet image. The upcoming housing market crash will be nearly as bad as 2007. These numbers are scary. Companies will start laying folks off to boost stock prices, &amp; the supply of housing will skyrocket.

Sean O’Brien Retweeted

App Store@AppStore · Jun 12, 2022

Heading out on a road trip? 🚙 Flip on @AutioApp, an audio app that tells the stories, secrets, and histories about the people and places you pass. Best of all, it's all read by a cast of narrators including Kevin Costner and @JohnLithgow! 📲: apple.co/HearHereAOTD

Sean O’Brien Retweeted

AutioApp@AutioApp · Jun 1, 2022

HearHere is now Autio. It’s a big world out there and while many of our users listen to our stories on road trips, many more use our app on planes, while walking, and even traveling virtually from home. While our product will always include location-based storytelling, we want