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Deep Sail Capital

1 month

Q2 2024 Investor Letter is now available on our website. The letter includes our long thesis on Kraken Robotics $PNG.V / $KRKNF

Investor Letters | Deep Sail Capital

www.deepsailcapital.com

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Deep Sail Capital

@DeepSailCapital

6 years

Things they should teach in high school: • Financial Literacy: (APRs, Budgeting, Taxes, Investing, and Credit) • Fitness (Not Sports): Eating Right, Exercise • Proper correspondence • Networking • Excel • Coding • Corporate Navigation • Sales / Negotiating • Happiness

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Deep Sail Capital

@DeepSailCapital

2 years

AFFIRM CEO: NOT WORRIED ABOUT $AAPL ENTERING BUY NOW, PAY LATER BC ITS ALREADY A HEAVY SATURATED MARKET WITH TERRIBLE ECONOMICS

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Deep Sail Capital

@DeepSailCapital

5 years

Advice to my 21 yr old self: 1) Take big risks in your 20s with your career and investments, swing for the fences. If you connect on a big swing it could materially change your life trajectory, and if you miss you still will likely learn more than not swinging at all.

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Deep Sail Capital

@DeepSailCapital

5 years

Top Investment Podcasts: 1) Invest Like the Best 2) The Knowledge Project 3) a16z 4) The Jolly Swagman 5) Scuttleblurb 6) The Acquires Podcast 7) Masters of Scale 8) Focused Compounding 9) How I Built This 10) North Star Podcast 11) Investing City Podcast What else?

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Deep Sail Capital

@DeepSailCapital

3 years

What if?

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Deep Sail Capital

@DeepSailCapital

3 years

Remember when you fake sold yourself your own NFT for like $48m. Sooo, the IRS is expecting its cut.

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Deep Sail Capital

@DeepSailCapital

5 years

My SuperMoat List per request.

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Deep Sail Capital

@DeepSailCapital

18 days

@Divergent7651 I didn’t much, 150% regret it. Honestly one of the best gifts a parent or grandparent can give a 20ish year old is travel.

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Deep Sail Capital

@DeepSailCapital

4 years

WSB actually has some really good content.

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Deep Sail Capital

@DeepSailCapital

4 years

Finance / Investing Insights that I have Learned in the last 7 years on Fintwit:

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Deep Sail Capital

@DeepSailCapital

4 years

The CFA is hot garbage, don’t put it CFA in your Twitter handle, no one on Twitter gives a shit, it actually looks bad. Street cred is street cred, earn it, don’t proclaim it.

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Deep Sail Capital

@DeepSailCapital

5 years

Been at Disney the past few days: •Have not seen one person wearing a mask •Obesity is a serious problem •People get really bad tattoos •Star Wars Galaxy Edge is legit awesome •Saw three mid aged British guys drinking in the park at 8am, classy

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Deep Sail Capital

@DeepSailCapital

4 years

My Top Picks for 2021: 5 Longs and 5 Shorts:

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Deep Sail Capital

@DeepSailCapital

2 years

What are some small caps stocks that you think are super cheap here? I’m talking dirt cheap, not just kind of cheap. 2-5x in next few years type of cheap.

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Deep Sail Capital

@DeepSailCapital

3 years

THEY FOUND UFOS THAT DEFY THE KNOWN LAWS OF PHYSICS. WHY ARE WE NOT TALKING ABOUT THIS?

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Deep Sail Capital

@DeepSailCapital

3 years

Coinbase is not worth $100B and if you buy them here you are in for a wake up call with a markdown. A Thread: 👇

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Deep Sail Capital

@DeepSailCapital

9 months

@ChrisJBakke @BluthCapital This is a lesson to everyone, if we can all take one lesson way from this it’s this: “Don’t use excel for risk management while you’re sleeping with your Ponzi scheme hedge fund manager while funding a political party with clients money.” Lesson learned.

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Deep Sail Capital

@DeepSailCapital

3 years

I bet Zuck could turn $TWTR into a $500B company in 3 years.

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Deep Sail Capital

@DeepSailCapital

4 years

Anyone got any new ideas in 10-100 Bagger land? As a reminder they generally need to be: •Small Enough (below $5B) •Ability to reinvest capital at high rates •Have a large addressable / potential market •Has a good management team

Deep Sail Capital

@DeepSailCapital

5 years

Anyone got any new ideas in 10-100 Bagger land? As a reminder they generally need to be: •Small Enough (below $5B) •Ability to reinvest capital at high rates •Have a large addressable / potential market •Has a good management team

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Deep Sail Capital

@DeepSailCapital

3 years

$AMC is unraveling overnight •CEO selling 75% shares •CFO selling 100% shares •CEO shooting down Illegal NFT squeeze idea •Tara dumps on Marc on Spaces •Community getting salty I hope you got some puts on the board.

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Deep Sail Capital

@DeepSailCapital

4 years

Paid my taxes and they were way less than I thought, so I went to Gibson and got the Tomahawk to celebrate.

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Deep Sail Capital

@DeepSailCapital

3 years

$SQ spending $30B to buy Afterpay (at 42 x Forward P/S) of while $PYPL built their own BNPL for prob less than $50m. 😳😳😳 Afterpay doing about $4.4B per quarter in GSV and PayPal doing $1.5B in GSV per quarter.

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Deep Sail Capital

@DeepSailCapital

4 years

This is how I am thinking about evaluating COVID-19 business impacts. Where am I off?

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Deep Sail Capital

@DeepSailCapital

3 months

$NVDA and the AI ecosystem.

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Deep Sail Capital

@DeepSailCapital

4 years

SPAC Stratgey 101: 1: Find the most ridiculously valued public company 2: Find it’s nearest private competitor to buy 3: Issue a ton of warrants 4: Compare SPAC to overvalued public company 5: Limit share float 6: Create Warrant arb & short squeeze 7: Yacht Party 🎉

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Deep Sail Capital

@DeepSailCapital

3 years

Maybe the entire bubble is just one guy with a huge undisclosed offshore swap.

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Deep Sail Capital

@DeepSailCapital

5 years

👑 Emerging Moat Kings 👑 $ROKU - OTT Op System $TTD - Digital Ad Platform $SHOP - Ecommerce Platform (the anti AMZN) $MTCH - All things Dating $AYX - Process Automation (the anti Excel) $LYV - Live Performance Everything $ETSY - Alt E-commerce

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Deep Sail Capital

@DeepSailCapital

3 years

I mean I’m a payments guy and all, but you guys are all sniffing glue if you think these BNPL companies are worth what everyone is paying for them. There no moat and anyone with a POS or online checkout can do it. It’s like 4 lines of code and a bank routing #.

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Deep Sail Capital

@DeepSailCapital

2 years

Sir, this is a Wendy’s

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Deep Sail Capital

@DeepSailCapital

4 years

Remember when $NKLA was worth $35B ? Also This exact tweet but for $QS, $LAZR, $FUBO, $CIIC, $PLUG, and $BLNK in a few months.

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Deep Sail Capital

@DeepSailCapital

3 years

Anyone have any new ideas in 10-100 Bagger land? As a reminder they generally need to be: •Small Enough (below $5B) •Ability to reinvest capital at high rates •Have a large addressable / potential market •Has a good management team

Deep Sail Capital

@DeepSailCapital

4 years

Anyone got any new ideas in 10-100 Bagger land? As a reminder they generally need to be: •Small Enough (below $5B) •Ability to reinvest capital at high rates •Have a large addressable / potential market •Has a good management team

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Deep Sail Capital

@DeepSailCapital

3 years

How can you still own Chinese stocks at this point?

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Deep Sail Capital

@DeepSailCapital

4 years

What if there is 4-5% inflation but we just keep telling people it’s 2%, how long will that work? I mean we are at like year 7 and so far no one seems to have caught on.

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Deep Sail Capital

@DeepSailCapital

5 years

My Top Picks for 2020: 5 Longs and 5 Shorts: Longs: $AYX, $ESTC, $SDI, $SEAC, $EVI Shorts: $CVNA, $BYND, $CDZI, $TRUP, $PCG

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Deep Sail Capital

@DeepSailCapital

3 years

Stop it. Stop quoting Square’s revenue including Bitcoin exchange sales which is counted as revenue at the full transaction amount not a fee like a real exchange. This is a hill I will die on.

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Deep Sail Capital

@DeepSailCapital

3 years

My wife’s office opened on Monday, Dude teats positive for COVID Tuesday night, office closed Wednesday. Thanks for playing.

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Deep Sail Capital

@DeepSailCapital

3 years

What is a small but exciting market or industry that could be 100 times larger than it currently is in 10-15 years? Examples: Crypto in 2013, Cannabis in 2015

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Deep Sail Capital

@DeepSailCapital

6 months

@marketplunger1 These is basically cannon of sci-fi- Hyperion - It’s two books long. Foundation Series Dune Series Enders Game (original is amazing, Series kind of gets weird later on) I liked: A Fire Upon the Deep Rendezvous with Rama

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Deep Sail Capital

@DeepSailCapital

2 years

$ROKU a wildly misunderstood company. It’s a TV OS with 60m user (ROKU Stick/ ROKU TVs) It’s a AVOD Channel (The Roku Channel) It’s a DSP (OneView) It’s a TV wall garden, the only one. It’s a beast, it’s position in streaming TV is unmatched.

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Deep Sail Capital

@DeepSailCapital

3 years

Top Picks for 2022: 5 Long / 5ish Shorts

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Deep Sail Capital

@DeepSailCapital

4 years

Your welcome guys.

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Deep Sail Capital

@DeepSailCapital

3 years

I went through this entire list of ideas and let me say this is probably the best list I have received back so far from this poll. My fav ideas are: $TOI.V $BDSX $CLPT $ORGS $ID $MXCT $POSAF $CFLT $BFI $DRIO

Deep Sail Capital

@DeepSailCapital

3 years

Anyone have any new ideas in 10-100 Bagger land? As a reminder they generally need to be: •Small Enough (below $5B) •Ability to reinvest capital at high rates •Have a large addressable / potential market •Has a good management team

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Deep Sail Capital

@DeepSailCapital

6 years

Anyone got any new ideas in 10-100 Bagger land? As a reminder they generally need to be: •Small Enough (below $5B) •Ability to reinvest capital at high rates •Have a large addressable / potential market •Has a good management team

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Deep Sail Capital

@DeepSailCapital

4 years

What are your best new small cap ideas less than $1B? My backlog of ideas seems to be drying up. Send me some ideas.

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Deep Sail Capital

@DeepSailCapital

4 years

$TSLA owns Bitcoin $TSLA is in the S&P 500 Index You own an Index Fund You own Bitcoin We all do

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Deep Sail Capital

@DeepSailCapital

3 years

12x since this tweet. $ROKU

Deep Sail Capital

@DeepSailCapital

6 years

The people buying $NFLX right now are the exact same people that are going to be buying $ROKU in 2-4 years. The real alpha is not buying a company with a clearly established moat, it's buying a company before everyone agrees it has a moat and being right.

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Deep Sail Capital

@DeepSailCapital

3 years

What if, and I’m just spitballing here, Elon Musk is a fucking moron grifter that just jumps on to the last thought in his head that helps his near term psyche.

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Deep Sail Capital

@DeepSailCapital

4 years

Seriously if you want to pay off a loan pay more than the minimum amount, stop with the “I paid $35,000 and I still owe $35,000 in loans”. It just shows that you’re a moron that doesn’t understand basic math or what your getting yourself into, not that the system is broken.

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Deep Sail Capital

@DeepSailCapital

4 years

What are your best long ideas that could 2-4x over the next 12-18 months? Here are mine: $PLAY $BXC $PAR $SHSP $ANGI Basically any E&P company that can survive but I have no idea which ones will.

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Deep Sail Capital

@DeepSailCapital

9 months

If the economy is doing fine, inflation has come down, and unemployment is historically low, why exactly does the Fed need to cut rates?

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Deep Sail Capital

@DeepSailCapital

2 years

@marketplunger1 When you wife asks “Which XXX do you like better?” just randomly pick one and say “that one I can’t stand the other one” even though you don’t care and have no preference whatso ever. Your logic doesn’t matter, your conviction is an acknowledgment that this decision is important

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Deep Sail Capital

@DeepSailCapital

2 years

Guys if you exclude the house flipping losses and the operating expenses, $OPEN is a cash cow. A lot people can’t see it.

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Deep Sail Capital

@DeepSailCapital

3 years

Guys I am releaseing a short report on a meme stock with a valuation of $31B and has a legacy business model that is in terminal decline and an investor bases that is batshit crazy. Keep and eye out to find out which one. 🔥🚀💩

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Deep Sail Capital

@DeepSailCapital

4 months

Anyone have any new ideas in 10-100 Bagger land? As a reminder they generally need to: •Be small enough (below $5B Market cap) •Have the ability to reinvest capital at high rates •Have a large addressable / potential market •Have a good management team

Deep Sail Capital

@DeepSailCapital

1 year

Anyone have any new ideas in 10-100 Bagger land? As a reminder they generally need to: •Be small enough (below $5B) •Have the ability to reinvest capital at high rates •Have a large addressable / potential market •Have a good management team

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Deep Sail Capital

@DeepSailCapital

1 year

Anyone have any new ideas in 10-100 Bagger land? As a reminder they generally need to: •Be small enough (below $5B) •Have the ability to reinvest capital at high rates •Have a large addressable / potential market •Have a good management team

Deep Sail Capital

@DeepSailCapital

2 years

Anyone have any new ideas in 10-100 Bagger land? As a reminder they generally need to: •Be small enough (below $5B) •Have the ability to reinvest capital at high rates •Have a large addressable / potential market •Have a good management team

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Deep Sail Capital

@DeepSailCapital

2 years

Action plan •Buy Twitter •Charge $1500/month for a Corporate account •Charge $50/month for a Blue Check Mark •Charge $10/month for Twitter Blue add Edit Function to Blue accounts only •Fire 2/3 of the R&D Team (doesn’t even matter which 2/3)

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Deep Sail Capital

@DeepSailCapital

4 years

So he was a parody account after all.

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Deep Sail Capital

@DeepSailCapital

4 years

@GerberKawasaki Shouldn’t you have gone through their financials before you became a bond holder, it is your responsibility to know what your buying as a fiduciary

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Deep Sail Capital

@DeepSailCapital

3 years

Big Idea: Excel but it doesn't freeze all the fucking time.

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Deep Sail Capital

@DeepSailCapital

5 years

Advice to my 21 yr old self: 2) No one knows anything. No one has it all figured out, no one is well trained or infallible. Most people are just faking it until they make it. Don’t think too highly of people just bc they are older, have more experience, or claim to be an expert

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Deep Sail Capital

@DeepSailCapital

4 years

Remember in the Spring/Summer of 2008 when it was pretty clear that Housing was fucked and major bubble was bursting yet the market held in there for like 6 months. Oh, no, no reason I’m bringing this up, none at all. 😉

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Deep Sail Capital

@DeepSailCapital

4 years

Nothing changes sentiment like price.

Phil Bak

@philbak1

4 years

BTC $385 BTC $23,440

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Deep Sail Capital

@DeepSailCapital

5 years

Anyone got any new ideas in 10-100 Bagger land? As a reminder they generally need to be: •Small Enough (below $5B) •Ability to reinvest capital at high rates •Have a large addressable / potential market •Has a good management team

Deep Sail Capital

@DeepSailCapital

6 years

Anyone got any new ideas in 10-100 Bagger land? As a reminder they generally need to be: •Small Enough (below $5B) •Ability to reinvest capital at high rates •Have a large addressable / potential market •Has a good management team

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Deep Sail Capital

@DeepSailCapital

3 years

What’s your “load the boat” value on favorite long term investment ideas where you would go max long at the valuation? $U below $75 $ADYEN below $14 $ROKU below $120

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Deep Sail Capital

@DeepSailCapital

3 years

Right now is actually the best time I can remember in recent history to be hunting for 10 baggers in SMID cap stocks. A lot of heros are gonna be made from here.

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Deep Sail Capital

@DeepSailCapital

3 years

I use the reverse DCF calculator on Gurufocus a lot, it’s a quick and easy way to see what growth assumptions are underpinned in a stock assuming mature margins. $RICK priced at 10% growth $PYPL priced at 18% growth $TPB priced at 4.5% growth

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Deep Sail Capital

@DeepSailCapital

5 years

Advice to my 21 yr old self: 11) Buy $AMZN and $MNST Calls.

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Deep Sail Capital

@DeepSailCapital

4 years

Not gonna lie I am getting used to this self isolation thing. Drinking every night, wearing sweatpants to work, watching a lot of Netflix, no weekday commute, no kids activities, and did I mention the drinking every night .......

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Deep Sail Capital

@DeepSailCapital

5 years

Updating my Potential 10 Bagger List: $SHSP $INSG $EVI $TPB $POLA New Additions: $AYX (yes it would be a $50B comp) $PAR $BLFS Feel free to add.

Deep Sail Capital

@DeepSailCapital

6 years

My top Potential 10 Baggers List: $SHSP $INSG $EVI $SPAR $TLRA $TPB $POLA $RMBL $CATS Feel free to add.

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Deep Sail Capital

@DeepSailCapital

10 months

Here is my "Sell List - Crap" These are the crapiest companies that I follow and I believe mid term will all be down. Note, all these have varying short dynamics, including high short float, low float, manipulative insiders, etc, so Do your own Due Diligence.

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Deep Sail Capital

@DeepSailCapital

4 years

He will go down in history as the worst president ever. Goodbye Trump you won’t be missed.

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Deep Sail Capital

@DeepSailCapital

5 months

Is there anything left that you can say with high certainty is “cheap” right now? I can’t think of one thing equity or otherwise I view as cheap.

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Deep Sail Capital

@DeepSailCapital

3 years

I’m extremely bullish on the pick and shovels of the coming Cell/Gene Therapy avalanche. IMO the general investing public doesn’t get how different the Cell/Gene Therapy model will be compared to the current centralized molecule model. Many additional service layers emerge.

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Deep Sail Capital

@DeepSailCapital

5 years

“Believe in something, even if it means sacrificing everything [except profits]” - Nike

New York Post

@nypost

5 years

Houston Rockets merchandise disappears from Chinese Nike stores

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Deep Sail Capital

@DeepSailCapital

4 years

The EV bubble is just another industry fad. You can make a direct line from 3D printing to Crypto to Cannabis to EVs. As the bubbles before it, it will end in tears for investors.

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Deep Sail Capital

@DeepSailCapital

9 months

What is your favorite special situation right now? Looking for: ▪️Spinoff ▪️Asset Sale ▪️Special buyback/dividend ▪️Potential M&A ▪️Rights offering ▪️Distressed asset ▪️Merger Arb

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Deep Sail Capital

@DeepSailCapital

4 years

Post Covid-19 changes I expect: 1) Companies will be more conservative with balance sheets, especially cash positions where they know they may need months of cash just to survive. 2) Returns on Capital will fall in certain industries because of #1

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Deep Sail Capital

@DeepSailCapital

3 years

You know who is gonna make all the EV s? The same guys that made the ICE vehicles You know why? BC it’s not about technology, it’s about supply chain, manufacturing, marketing, and sales channel How much are they gonna make on EVs? About they same they make on ICEs

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Deep Sail Capital

@DeepSailCapital

4 years

@TheStalwart @crowdturtle Get out your best non stick pan, coat it with a heaping amount of butter, bring steaks to room temperature, heat the pan up really hot (400 degrees), and then most importantly before cooking is to move out of New York City and buy a regular house, then put the steaks on and enjoy

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Deep Sail Capital

@DeepSailCapital

6 years

My top Potential 10 Baggers List: $SHSP $INSG $EVI $SPAR $TLRA $TPB $POLA $RMBL $CATS Feel free to add.

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Deep Sail Capital

@DeepSailCapital

4 years

What’s the most ridiculous stock price right now that you are like holy crap how is that even possible? List ticker and price.

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Deep Sail Capital

@DeepSailCapital

3 years

Kind of hoping Software stocks overshot to the downside and they become pariahs for like 6 months so I can load the boat and retire to start my life as a professional craft beer taster.

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Deep Sail Capital

@DeepSailCapital

4 years

$GME PUTS, IM NOT FUCKING SELLING. 💎🙌

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Deep Sail Capital

@DeepSailCapital

1 year

Cell & Gene Therapy is on the cusp of multiple years of +50% growth. Seems like the biggest growth trend that is not reflected in the stocks that will benefit the most from it.

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Deep Sail Capital

@DeepSailCapital

4 years

Seriously she should be let go for even suggesting this.

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Deep Sail Capital

@DeepSailCapital

11 months

GLP-1 impacts. From @rochonpapi a locked account.

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Deep Sail Capital

@DeepSailCapital

3 years

Annual Inquiry: Who are the best small cap (<$5B) management team’s right now? Traits to consider: •Executed on what they said •Adapted to adversity •Strong capital allocation •Good communication / IR •Skin in the game

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Deep Sail Capital

@DeepSailCapital

3 years

$BROS on VIC. Make sure to check your share count on all new listings folks.

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Deep Sail Capital

@DeepSailCapital

3 years

So all $FSLY had to do for everyone to realize how critical they are to the internet was shut down the system for a few hours.

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Deep Sail Capital

@DeepSailCapital

5 years

Top Drawdowns over the last week from any of my High Moat Lists: $AYX -15.4% $LYV -15.3% $SHOP -13.3% $CLB -12.2% $WDAY -11.9% $WIX -11.9% $MA -11.3% $TTD 11.3% $TDG -10.8% $V -10.8% $AXTA -10.3% $PYPL -10.3% $ILMN -10% $FLT -10%

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Deep Sail Capital

@DeepSailCapital

3 years

The real money is made by investing for 10 years while everyone else is investing for 3 years.

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Deep Sail Capital

@DeepSailCapital

9 months

What are the best small $POOL, $WSC, $CSU type rollups / serial acquirers that have a long runway, a well defined M&A strategy, and an excellent management team?

Deep Sail Capital

@DeepSailCapital

2 years

What are the best small $POOL, $WSC, $CSU type rollups that have a long runway, a well defined M&A strategy, and an excellent management team?

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Deep Sail Capital

@DeepSailCapital

3 years

Seriously $IAC do it. Buy the entire thing.

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Deep Sail Capital

@DeepSailCapital

5 years

Advice to my 21 yr old self: 3) Keep learning, don’t slow down, actually speed up. At 21 even the smartest, best educated person can be outpaced by someone willing to keep learning. Learning doesn’t stop at school. With a smartphone literally everything is available to learn.

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Deep Sail Capital

@DeepSailCapital

6 years

The people buying $NFLX right now are the exact same people that are going to be buying $ROKU in 2-4 years. The real alpha is not buying a company with a clearly established moat, it's buying a company before everyone agrees it has a moat and being right.

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Deep Sail Capital

@DeepSailCapital

9 months

He might not be the hero we want, but he’s the hero we have.

Ron Filipkowski

@RonFilipkowski

9 months

George Santos gives a specific example of how he says GOP Rep. Nicole Malliotakis is using info from classified briefings to make money on stock trades.

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Deep Sail Capital

@DeepSailCapital

1 year

Twitter and Podcasts have really taken away the mystique of VCs being the smartest guys in the room.

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Deep Sail Capital

@DeepSailCapital

2 years

What are the best small $POOL, $WSC, $CSU type rollups that have a long runway, a well defined M&A strategy, and an excellent management team?

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Deep Sail Capital

@DeepSailCapital

3 years

Realized at 11pm last night that somehow one of our kids turned our fridge on to showroom mode where it doesn’t cool and lost an entire fridge worth of food including $400 of beef tenderloin. Happy Thanksgiving Everyone!

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Deep Sail Capital

@DeepSailCapital

8 months

Gonna be hilarious when $SAVE goes into bankruptcy and $JBLU takes all their business for near zero dollars instead of $3.8B.

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