staysaasy @staysaasy Twitter profile

Pinned Tweet

staysaasy

10 days

If you’re in a sustained conflict with your manager, you’re probably not going to “win” If you’re fighting with your manager for over a year - if you can afford to, find something else. Life is just too short.

Fighting With Your Boss

Fights between a manager and report can be some of the most stressful experiences in life.

staysaasy.com

1

7

Last Seen Profiles

@marques_eder

@buttercuplvusd

@VRMurta

@5o5NB

@Pallet_Exchange

@CubNg62350

@LA48_OFICIAL

@hijabjilbab1

@PoseysFingers

@yefanatics

@joshtho48488708

@CoachChim

@digital_bathtub

@aya_xuan703

@s7edgesilver2

@Jabbermikkey

@CityPolice

@boyzinxx1

@247SecurityZA

@FoundFathersTBT

@B9007298

@Sali_du_binks

@Sho26063

@rinon_hase

@cukienaknikmati

@LGrima89

@IntersectMBO

@ammawhiney

@weikengchen

@taroemir

@meruhen_neko

@lastlight098

@MollyESPN730

@thisisjorge

@muglare

@soopy_zzZ

staysaasy

@staysaasy

16 days

@JoshuaOgundu There's a beautiful thing happening in your comments where she called out VC/PE for being mansplainers, and they're now in your replies mansplaining. (they have good points but it's still funny)

6

20

1K

staysaasy

@staysaasy

3 months

@Rainmaker1973 Then why am I such a shitty swimmer Then why do dolphins suck so bad at Mariokart

5

14

513

staysaasy

@staysaasy

9 months

95% of why big company people and startup people can't get along is that the optimal move at a startup is to play to win and the optimal move at a big company is to play not to lose. This is a much more important factor than speed, bureaucracy, size, politics, stability, etc

9

57

464

staysaasy

@staysaasy

3 months

@Rainmaker1973 Ah I thought that was for when two pens want to make a baby pen.

1

4

248

staysaasy

@staysaasy

2 years

@devahaz It's mainly said by VCs. Like yes people respond faster to people who can make or break their company. I know that I personally respond faster to VCs because I want them to like me in case I need $ one day. I also respond fast to my mom bc I care if she likes me too

2

0

214

staysaasy

@staysaasy

28 days

@Austen Psycho DEI stuff is cringe. Anti-DEI stuff is cringe. Anti-anti-DEI stuff is cringe. None of it is funny or has a sense of human.

7

0

211

staysaasy

@staysaasy

4 months

@paulg It’s that Rick Steves life baby

2

1

186

staysaasy

@staysaasy

20 days

@Carnage4Life I think a very under-reported cause here is the rise of remote work letting tech employees tax optimize within the US. IMO that's the majority of what's going on here.

8

2

132

staysaasy

@staysaasy

7 months

@buccocapital More like Wayunfair

5

0

125

staysaasy

@staysaasy

3 years

@NateSilver538 So cool you started practicing medicine bro!

1

2

91

staysaasy

@staysaasy

14 days

@Jason Imagine being Howard Dean who got bounced out of a primary for an enthusiastic shout.

7

3

78

staysaasy

@staysaasy

2 months

If a high performer suddenly starts being upset about lots of little things, it’s usually one big thing. In order of probability, it’s usually one of the following: * they’re faced with a challenge they’re struggling with and don’t like doing a bad job * personal life issues *

2

6

67

staysaasy

@staysaasy

1 year

@eladgil What happens when ChatGPT kills all the knowledge stores it needs for training?

5

3

63

staysaasy

@staysaasy

1 year

The ratio of "times I've regretted acting too slowly" to "times I've regretted acting too fast" is probably 99:1 in my work life, and 1:99 in my personal life.

2

6

58

staysaasy

@staysaasy

5 months

Some people are salivating at the idea of software engineers being replaced by robots. Y’all forget like half of SWEs are just hardcore smart people that went to where the money is. If robots come for our jobs, we’re coming for yours. Also, AI could only replace good developers

6

9

56

staysaasy

@staysaasy

3 years

@Suhail Noise cancellation is the future. An increasingly urban world need quiet apartments.

2

0

56

staysaasy

@staysaasy

6 months

At over 1k people in any org, even if you do everything perfectly, you’ll have at least one person that thinks you’re a scumbag just for being an executive, and will assume nearly everything you do is nefarious. The sooner you become at peace with this reality the better.

2

51

staysaasy

@staysaasy

8 months

One of the more nuanced errors you can make as a manager/leader is advocating people do something they probably were going to do. You miss the opportunity to know if they were going to do it, and some subset of people are going to react poorly to it seeming like now it was you

3

4

53

staysaasy

@staysaasy

8 months

Junior Engineer: what’s the problem? Mid-level Engineer: this is the problem. Senior Engineer: there is better tech for this problem. Staff Engineer: there is better tech for this problem, but it’s not worth the migration. Principal Engineer: there is better tech and we’ll

3

10

50

staysaasy

@staysaasy

2 months

Do I really miss working at a startup, or do I miss being 25 and working with my friends all day?

4

2

49

staysaasy

@staysaasy

1 month

Some non-startup engineers are like. I need a mentor to guide my architecture I need AI to write my code I need a QA team to make sure it doesn’t have bugs I need a DevOps team to deploy my code I need a PM to resolve any ambiguity in requirements I need a NOC to do

2

49

staysaasy

@staysaasy

20 days

@EricRWeinstein Spoken like a real 1+1=2 kind of guy.

5

0

46

staysaasy

@staysaasy

8 months

After watching the board of a $100B company attempt to completely self-immolate in a matter of hours, no one has any excuse to ever feel imposter syndrome again.

0

11

47

staysaasy

@staysaasy

2 years

@paulg What if they all say their VC.

1

0

44

staysaasy

@staysaasy

11 months

@thdxr All new tech hires should need to do a required 12 month stint at a dying Series A startup

1

2

45

staysaasy

@staysaasy

2 years

@paulg Isaac Newton lost all his money in the stock market. Guy defined the universe but couldn’t manage a 401k. It happens.

1

2

43

staysaasy

@staysaasy

5 months

@jaltma We invest in founders from all locations: SOMA, the mission, hayes valley, fidi and even design district if we're feeling extra wild.

0

45

staysaasy

@staysaasy

2 months

@Carnage4Life Saying "we're a family" is a warning sign because it's either used to manipulate teams (not that common) or is a sign that leadership is still inexperienced at leading through hard times. Nobody says it after they've gone through the hard stuff at scale.

0

44

staysaasy

@staysaasy

8 months

In the last 3-4 years it feels like the startup world has finally taken off the mask and gone from "I want to change the world" to "startups are the fastest and most fulfilling way to have a shot at getting filthy rich." I actually find the honesty refreshing.

2

42

staysaasy

@staysaasy

23 days

I fucking love how unreasonably optimistic people with early startup experience are. There’s a brick wall, no problem, I’ll go through it! And I fucking loathe how easily people who don’t have that experience claim they are helpless. I have to talk to someone I don’t know, nooo!

4

0

43

staysaasy

@staysaasy

8 months

At some level, it’s impossible to be “nice” when people are severely incompetent. When you don’t manage underperformance, the truth of situations is simply not nice. In the worst cases, you force high performing, high responsibility people to be truth tellers to low performers,

6

4

43

staysaasy

@staysaasy

6 months

Underrated executive skills: * Memory * Writing * Ability to run a good meeting * Sense of humor * Ability to act carefully while being anxious/nervous * Consistency

2

40

staysaasy

@staysaasy

4 months

Startups are hard but you sure do learn a lot. I regularly see CEOs of companies at $1-2m ARR who are noticeably more poised and *wise* than directors / VPs of companies at scale - even ones with 10x larger teams than the startup CEO's entire company.

3

1

40

staysaasy

@staysaasy

1 year

@GRDecter It must have been on a 10b5-1 plan though, right? ... right?!

5

2

36

staysaasy

@staysaasy

2 months

@devahaz This is compounded because most startups massively overestimate the quality of background they can recruit. As a result most of the best people at a startup are diamonds in the rough, and if you want to find a diamond you've got to go through a whole lot of rough.

4

0

38

staysaasy

@staysaasy

7 months

@andrew__reed Ehhh bit of a yellow flag that he owns a suit jacket (although +points for it not fitting properly)

1

0

37

staysaasy

@staysaasy

1 year

@Rainmaker1973 Also me after they finally pull me away from the Pizza Hut buffet

0

37

staysaasy

@staysaasy

3 months

Just move fast 90% of your planning, prevaricating, debating, analyzing, and project managing could be avoided if you moved faster. Instead of ordering priorities A B C like you're arranging the carriages for the royal wedding, just do all of them Just move fast

2

5

35

staysaasy

@staysaasy

30 days

Growing as a leader is not about doing more complex stuff. Growing as a leader is about convincing smarter and smarter people that they should do the simple thing.

1

35

staysaasy

@staysaasy

1 month

Habit of highly successful teams #57 : when you identify a superstar employee, you push the chips all in on them immediately. You don't make them wait their turn, you don't set them up for a high visibility win to help optics. You put the money and power in their hands that week

2

0

35

staysaasy

@staysaasy

5 months

I've never seen a successful startup founder / early employee / exec who wasn't an absolute machine at getting things done. It's A+ to be strategically brilliant, inspirational, excellent at sales and more, but the best also always output at an obviously higher rate at baseline

0

2

34

staysaasy

@staysaasy

1 year

@Carnage4Life They were fixing the problem of not having as much money as they would like

1

0

32

staysaasy

@staysaasy

2 months

If you’re not already an amazing company, how can you get amazing people to join you? The answer is by being focused on hiring what you need, vs looking for perfect people. OpenAI and Google and Meta are going to get all the people who are Staff Engineer level technical and

3

1

33

staysaasy

@staysaasy

11 months

If you're looking for the right tone to set at work I think a good default is "team player who doesn't tolerate being fucked with"

1

4

33

staysaasy

@staysaasy

1 month

Is it just me or does the AI hype still just not match reality? I get that GitHub copilot is better and deep fake scammers are better. But like Nvidia biggest company in the world doesn’t match my day to day benefit from the tech. Like I bought a bunch of iPhones and

6

3

32

staysaasy

@staysaasy

18 days

I’ve seen a lot of startup growth, and I like dumb plans. I like plans that can fit on a single Powerpoint slide. I like plans that don’t require you to know frameworks, or methodologies, or advanced math to determine whether they make sense. I like plans that don’t require

3

1

30

staysaasy

@staysaasy

7 months

My brother asked me for high risk, high reward investment advice. My advice: focus on your career. People spend countless hours trying to invest better, but won’t ask for a promotion because it’s uncomfortable, or there’s associated risk. But the least risk high risk thing you

1

5

28

staysaasy

@staysaasy

11 months

@nikillinit @patio11 It's a nerd version of Coming to America and I can't get enough

0

30

staysaasy

@staysaasy

1 month

@GergelyOrosz Facebook is no longer Meta's most important product Google is still by far and away Alphabet's most important holding

1

0

30

staysaasy

@staysaasy

9 months

Here's the advice I wish somebody would have given me when I got out of college: * Be patient every year but urgent everyday. Seriously bias towards action - ship the code, build the thing. You’d spent enough time studying, get reps in. Avoid any company that makes you wait to

1

0

29

staysaasy

@staysaasy

3 months

One of the best ways of judging a leader is how they treat people 10+ years younger than them. If they're overly firm, it usually means they have a big ego, and no concept of the advantages they had. If they're overly apologetic, it usually means they don't have the backbone

2

1

28

staysaasy

@staysaasy

8 months

When you're a VP, roughly 25% of your job is simply not losing your shit when you hear bad surprises.

1

0

27

staysaasy

@staysaasy

17 days

The most common form of gaslighting in business is managers who lie to their reports about how good they think they are. You’re doing solid, good, great even. This feedback keeps happening. But somehow that doesn’t translate to promotions, or comp increases, or more

1

28

staysaasy

@staysaasy

2 months

Thinking today about my buddy who died in Afghanistan. We both were sort of floaters between different groups in high school. Both a little stir crazy, a little independent, a little more interested in reading than getting fucked up. We were both smart, but my grades were a

1

27

staysaasy

@staysaasy

11 months

I’m a big believer that every highly motivated individual has at least one person who tells them they’re great and makes them believe they can do anything, and one person who told them they couldn’t do something, who they want to prove wrong.

3

2

27

staysaasy

@staysaasy

2 months

@devahaz "We're only looking for the best talent, A players" "My brother, the A players are less horny for your startup with $39.99 in MRR than you seem to think"

0

25

staysaasy

@staysaasy

20 days

@jonmasters @Carnage4Life Such a weird response to something I did not say.

1

0

27

staysaasy

@staysaasy

2 months

The only thing more infectious than a young ambitious person is an old ambitious person.

0

3

26

staysaasy

@staysaasy

3 months

The absolute number one skill in leadership is the ability to sustain extremely long periods of chaos and anarchy, and avoid the instinct to give up or fix things in the easy way. An easy example is giving feedback. Something happens in a meeting. Sure you could give feedback

0

26

staysaasy

@staysaasy

1 month

@rohindhar I guess that’s cool if you’re into beauty and serenity.

0

1

26

staysaasy

@staysaasy

2 years

@Rainmaker1973 Been a crazy year for Pluto.

0

26

staysaasy

@staysaasy

2 months

If you think working with a globally distributed team is easy lets chat tonight at 11:00pm and talk about it for an hour.

7

2

26

staysaasy

@staysaasy

1 year

@sama So ChatGPT can handle gestures now?!?

0

1

25

staysaasy

@staysaasy

2 months

Great software can be highly stable, but not perfectly stable. The only totally stable software is software that isn’t updated and isn’t used. New users and new functionality incur risk. It’s a delicate balance. What complicates things is that there is software that is

2

4

25

staysaasy

@staysaasy

5 months

UX is weird as an enterprise differentiator * If your UX is like 1.5-2x better, it basically doesn't matter. Jira still crushes it. Teams is hammering Slack. * But if your UX is 5x better than the competition you run the table. 100% of the market is going to move to Figma.

3

2

25

staysaasy

@staysaasy

15 days

@Carnage4Life But have you considered that if you complete the ritual of spinning in a circle 5 times while chanting "AI" you can summon an Elder Growth Investor to do your next round

0

24

staysaasy

@staysaasy

27 days

If you’re a manager of multiple teams, a big part of the job is copying best practices from your higher performing teams to your lower performing teams. Not all best practices work everywhere, but most do. Suggest adoption vs force it, in most cases. Low performing teams

2

24

staysaasy

@staysaasy

3 months

Being a middling performer who thinks they're a top performer is often worse than just being a middling performer who knows it and is working on their skills. And the #1 sign of this pattern is a rigid worldview.

1

24

staysaasy

@staysaasy

9 months

A consolidated list of communication advice: * Agree with ideas, not with people. Avoid saying "I agree with Bob" when you could say "I agree with X" (which Bob just said). The former divides the room into teams. * Agree async, disagree synchronously. Don't do more than 5

2

6

24

staysaasy

@staysaasy

2 months

A key to startup success seems to be being introspective enough that you can improve/evolve over time, but not so introspective that you strongly question whether you should keep working really hard

2

0

24

staysaasy

@staysaasy

28 days

Next week on Stay SaaSy we talk about knowing when it’s time to quit your job, a critical skill for anyone in tech, and also for people who travel with the nuclear suitcase.

0

1

24

staysaasy

@staysaasy

28 days

It’s really easy not to ignore your direct reports. Just have good 1:1s. With 30 minutes once a week of actual focus, you can make every direct report feel challenged, considered, and understood. It’s crazy how many managers just suck at 1:1s. Phone them in, no agenda, no

1

24

staysaasy

@staysaasy

1 month

You gott ask a prospective employer questions when interviewing for a job. If you can't think of good ones, try these: * What's your TAM and why are you best positioned to take it? * Who is your strongest competitor and how will you defeat them? * What urgent problem does hiring

1

24

staysaasy

@staysaasy

9 months

Reasons you're struggling as a software engineer: * You’re not doing the small stuff fast enough. Most repetitive tasks should have aliases. Toggle between applications without taking your hands off the keyboard. Learn emacs or vim basics. Do the small stuff fast. * You’re not

0

5

24

staysaasy

@staysaasy

3 months

Zuck in 2 years.

0

1

23

staysaasy

@staysaasy

1 year

@ChrisJBakke @anothercohen I'm sorry that this happened to you, you should consider signing up for my $68.99 / month therapy startup in which you tell ChatGPT your deepest secrets and it responds with an AI-generated NFT. We just raised a $5m debt line from SVB.

1

0

22

staysaasy

@staysaasy

4 months

Literally your entire job as a manager is getting people to act in ways they otherwise wouldn’t. About half of doing that is just embracing discomfort and doing the hard thing. It’s being ambitious. It’s hiring the right people. It’s firing the right people. It’s finally

0

2

21

staysaasy

@staysaasy

5 months

@Jason Gotta buy a bunch of fries when prices are low and sell them down the street when prices are high. Carbitrage.

1

0

22

staysaasy

@staysaasy

11 months

Finding a successful, good-cultured, mission-driven (save the world) startup can be extremely difficult to do. And even if you do find one, many missions prove less effective or noble in hindsight. As an alternative, if you want to make the world better, find a company whose

0

3

22

staysaasy

@staysaasy

2 years

@elonmusk @Jason @DavidSacks @Zappos You gotta get some sleep man.

0

21

staysaasy

@staysaasy

30 days

“I can’t change the behavior of people who don’t report to me” is nonsense. Learning how to solve problems of that shape is a core aspect of leadership.

3

1

22

staysaasy

@staysaasy

2 months

Not caring whether your team succeeds is the most contagious emotion. Patient zero can spread the attitude to an entire team, who can spread it further and further. It's worse than being mean, rude, or even disrespectful. People don't contract rudeness at the same rate.

2

22

staysaasy

@staysaasy

2 years

A quiet warning sign of burnout - people start saying what they're really thinking, instead of the politically acceptable version of what they're supposed to say

0

9

21

staysaasy

@staysaasy

3 months

One of the super fun parts of working with a great team is taking meetings with external parties and watching people realize you’ve got a bunch of stone cold killers with you.

1

21

staysaasy

@staysaasy

10 months

One of the things you should really try to do before you’re like 27 is be part of a winning team. Could be sports or debate or a band or a a great company or whatever. The difference between a lackluster, lame ass team and a championship team is so foundationally different it

2

1

21

staysaasy

@staysaasy

6 months

People don’t want transparency, they want comprehension. When a system is complex, simple transparency is often counterproductive. Eg here’s the tax code, good luck. Here’s the binary source code, good luck. When a system is complex, broad comprehension can require -

3

0

21

staysaasy

@staysaasy

10 months

@gokulr @martin_c_mao +100 these cross-company conversations are the only form of work-related therapy that most of these successful CEOs get. At least the VPs / C-suite can get a beer and talk it out with some of their peers.

0

1

19

staysaasy

@staysaasy

5 months

Pro tip - if you’re interviewing at Google right now, just answer every question like “I’m sorry I can’t answer that question because it’d reinforce bias around the best way to invert a b-tree.”

1

4

21

staysaasy

@staysaasy

29 days

I would've expected that taking initiative was extremely coachable, but IME it's a really hard trait to change. In both ways: almost impossible to make someone a self-starter. And it's actually even harder to get a true powerhouse to *stop* taking the initiative as well

2

0

21

staysaasy

@staysaasy

1 year

@WillManidis ex-WeWork can't ship anything ex-Google can't understand business ex-IBM can't do addition/subtraction

1

19

staysaasy

@staysaasy

1 month

Great leaders recommend you books about every 18 months. They read something great, tell you about it, then get busy implementing it. Mid leaders tell you about great books all the time. But they never apply anything, they’re just in theory mode. Bad leaders don’t read.

2

1

21

staysaasy

@staysaasy

2 months

The more you trust Gartner about anything the less I trust you about everything

4

1

21

staysaasy

@staysaasy

1 month

One really subtle but major effect of hiring really good people, is that it inhibits weasel behavior. When people think their coworkers are a bunch of losers, they don't care if they think they're a piece of garbage. But if you hire the best, people will think "I really don't

1

20

staysaasy

@staysaasy

29 days

@Samantha_SN1 The Bum Bum Song My United States Of Whatever Shanequa Goldberg Variations Morton Feldman Captain Beefheart

3

0

20

staysaasy

@staysaasy

7 months

There are two ways to make sure that your team gets important things done: * Ask them to do 25 things, and only check on 20% of them * Ask them to do 5 things, and thoroughly check on every one of them 100% of the time Strategy #2 eats strategy #1 every time

1

3

20

staysaasy

@staysaasy

4 months

@Carnage4Life

0

1

19

staysaasy

@staysaasy

2 months

2

3

19

staysaasy

@staysaasy

4 months

One of the worst outcomes of retaining brilliant jerks is that they almost never, ever admit when they are wrong. This defensiveness leads to a lack of ability to clearly diagnose problems, which makes it hard to fix problems. You end up with brilliant jerks who always seem to

3

2

20

staysaasy

@staysaasy

8 months

One of the worst ways to shoot yourself in the foot as a leader at a technology company is to not understand exactly why some projects are harder than others, and why product velocity can be so variable. This can result in coming across as ignorant (best case) or completely

0

1

19

staysaasy

@staysaasy

3 months

A unique failure condition of high performers is the high performer who is great at executing most of the time, but is unreasonably pessimistic or stubborn in the face of some big goals. What's happening is that they don't know how to do a thing, but instead of saying "I don't

1

20