Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
from Invest Like the Best with Patrick O'Shaughnessy
58m 26s
The rapid evolution of AI is fundamentally reshaping how businesses operate, forcing a shift from traditional metrics like headcount and past performance to agility, adaptability, and customer-focused innovation. Ravi Gupta argues that the most valuable trait for modern leaders is not predictive foresight, but the ability to react swiftly and decisively to change—what he calls being a "world-class reactor." This mindset enables organizations to become more agile, customer-centric, and resilient. Small, nimble teams are gaining a significant edge over large, bureaucratic ones, as they can respond faster and deliver more value per employee. Leaders are urged to reevaluate core business models—such as pricing and roles—through an AI-lens, questioning whether current structures still make sense in a world where AI can perform complex tasks at scale. Real value comes not from isolated AI experiments, but from embedding AI into daily operations with deep context and shared understanding. Companies that embrace these changes will outperform those clinging to past practices. For investors, this means prioritizing founders with ambition, curiosity, and adaptability, and identifying companies that are not just adopting AI, but actively redefining their value propositions. Boards must evolve from passive oversight to active enablers of change, asking critical questions about leadership agility. Ultimately, the future belongs to organizations that prioritize speed, innovation, and customer value over size and tradition.
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Hello and welcome everyone.
I'm Patrick O'Shaughnessy and this is Invest Like The Best.
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Patrick O'Shaughnessy is the CEO of Positive Sum.
All opinions expressed by Patrick and podcast guests are solely their own opinions and do not
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My guest today is my good friend Ravi Gupta.
Ravi is a partner at Sequoia Capital and also the host of Glue Guys,
a podcast on the Colossus Network that discusses both business and sports.
I wanted to have him back on a vest like the best to discuss a recent essay of his that he called
AI or Die. As someone with incredible operating and investing chops,
Ravi believes we're entering an era where the constraints that historically limited small
teams are dissolving, creating unprecedented opportunities for those willing to embrace change
aggressively. We discuss why traditional metrics of corporate success like headcount
and processed adherence may become liabilities.
What it means to be a world-class reactor versus a world-class predictor and how magic per
employee and organizational agility will emerge as crucial measures of value creation.
Please enjoy my great conversation with Ravi Gupta.
So Ravi, a couple days ago you sent me a draft of this really interesting essay that you wrote
called AI or Die, which is such an interesting framing for something that I know you've been
thinking a lot about and have been thinking more and more about in a crescendoing way in the
last few weeks and months. Can you just start by describing the process of arriving at this essay
and like what precipitated it and then we'll talk about all of its various implications?
Like everyone you see these new model advances and they've come out so quickly that you are using
the models for whatever you're using the for the day before and it's hard to think of even what
to ask them when the new ones come out. So a couple of things happened. One, you know I'm on the
board of Sierra Breton Clay's company and they started describing some of the things that were
able to be done in O1 Pro that were not able to be done with 4.0 and I was surprised and I think
that the specific example that came up was when Clay was talking about something he was doing with it.
I asked him to show me how he was using it and when he did that he asked the model a question
which was are my instructions clearer? Is there anything else I can do to make it to clarify
what I'd like to have you do? That interaction was so different than anything I'd ever thought about
with a model. I'd never thought to ask it a question and the model came back and said no actually in
fact can you please clarify these five or six things and I was pretty stunned by that interaction.
That was point one point two was a friend of mine who was at one of the model companies left to go
to another one and I said hey what happened and he said the pace of progress has changed so much
in the last three months that I had to go to this one and in our business take them at Kohler
quote that you and I both love Matt is a good friend of ours both of ours our job is not to see
the future it's to see the present very clearly all of a sudden it felt like the present was
different than what I thought and so I just started trying to use it more myself and I think I'm
barely scratching the surface but I was pretty stunned at what was possible from this and I'm somebody
who like lives in Silicon Valley and works as a venture capitalist it made me wonder if there was
other people who are gonna be as stunned as I was so maybe talk about what you mean by AI or
dial in its most kind of intense form well if you take that Dario quote from his essay from October
he describes what he believes powerful AI will be and it's this idea of a country of geniuses
in a data center that's what's going to be available to anyone and he take what Sam has been saying
the quote he has is in a decade every person will be more capable than any person is today and if
you just take a moment literally just read the words again or say them again in your brain
they are like mind bending and so the point of what do I mean by AI or die if they're at all
right if there's something approaching right there's going to be dramatic change that is going to
come to any company to any person if we then think about the most intense version of that if that's
true then you should be able to recreate what we have now with dramatically fewer people working
on it because there are a country of geniuses available in a data center and so I think the
most intense version of that is envisioning a group of developers hanging out on a Friday night
and sorting companies based on their market cap and their number of people and their NPS
in some calculation and finding the biggest company with the most people with the lowest NPS
and then competing about who can build it faster it's just like a crazy thought of what could happen
but I don't think it's crazy if the AI's turned out to be as powerful as we think and then
the much less intense version that I think is very real is anything you have that prevents you
from embracing change right now is a huge limiter it's a huge limer if it's a lot of people in your
organization if it's adherence to a quarterly earnings that you've committed to if it is unwillingness
to make a change if this is changing as fast as I think it is and I think the people that run these
companies say it is anything that reduces your agility is a massive problem so since you first
had these couple aha moments with your friends at those leaving edge companies
what have you personally done differently to try to respect this faster than you thought
pace of change I love the word choice to respect it so the first thing I guess to be very honest
was I talked to Avni about what are we doing to educate our kids if this is true my first thought
was not what does it mean for businesses it means what does it mean for our family what does
it mean for the kids what is the right way to teach them in a world where the tools that are
going to be available to them are going to be totally different we realize that I don't think
that there's actually skills that I can teach them there's behaviors there's feelings there's
approaches and so what we got to was some version of we got to make sure that they're ambitious
we got to make sure they're curious we got to make sure they're resilient adaptable and their
high agency I think the reason that that then dovetailed like what have changed now I was sort of like
that's the same thing you have to be if you're like at a company you actually need the exact same
things and you and I have talked about this separately and I think you've added a couple to that
which we should go through those same behaviors are going to have to exist in the company specifically
what I've done personally is I try to use it more for real work I had dinner with somebody recently
and I hope he's not listening because of the setup I'm going to give you but it was with a company
somebody who was on the board of a company that I didn't know that much about I was not well prepared
for the dinner and it was somebody who I wanted to make sure I had a productive conversation with
and there was 20 minutes before I was going to go to the dinner and I prompted the model the latest
model the $200 a month one which I know sometimes people just don't want to do that because $200 a month
a lot of money it is but it's not a lot of money when you think about relatives like seeing the future
I mean that's literally what they're offering you right now so I put in I said I am a sophisticated
investor that was a very generous term for myself I have a dinner in 20 minutes I am not prepared for
this dinner and I'd like to understand deeply what this company does in a way that I can understand
within 10 or 15 minutes I'd like to understand these four or five things and I'd like to have some
good ideas for this person for what they could do and are my instructions clear and I use deep
research and he said no can you tell me these four or five things I told it four minutes of thinking
and it came back and I read it on the way to the dinner and we had a great dinner this person
thought that I knew what I was talking about that is a pretty different use then can you summarize
this email for me I think that the AI interaction most of us have is apples and amazing company
but the Apple intelligence summary of your text messages the most absurd it's a terrible experience
right and it's truly like laughable it's more used
for a comedy than it is used for like actual value right now.
And that's the interaction that most of us are having with this thing versus that wow
experience for me of, oh my gosh, I actually know a lot more about this company now.
And I would have never known this in this time period.
That's real work.
So the biggest change is like trying to have it help me with real work.
I want to dig in a little bit more to that imaginary spreadsheet you envisioned earlier,
which you said market cap number of employees and PS if your only thought exercise was trying
to find a single target for a company to go like you could have a activist help you
and have a hostile takeover of the company or something and install yourself as the CEO
with the goal of maximum value creation or something using this new tooling.
Talk me through how you would process that search trying to find that single company
that can be most positively impacted if they embrace this back to AI or die.
And maybe we'll die if whoever's running it doesn't embrace this rapid pace of change.
That is a good question and a very hard question.
I think that when we say the AI is much better than we think, I think practically speaking,
it means that it is way better and this is a stolen insight from our friend of mine.
But it is better at figuring out hard to figure out patterns than we would give it credit
for.
Do you see what I'm saying?
It finds patterns in ways that wouldn't be obvious and it finds them ridiculously quickly.
So you can be more ambitious and like where there might be a pattern that's not obvious.
Its ability to discern that is different.
So maybe an example would be if you give it some framework, it can give you good acquisition
ideas for the company because it can identify ways to optimize for the question you have.
I want to improve my distribution and I'm in this space.
It will find companies that are in a similar space that have tons of customers that might
be a nice tuck in or a transformational acquisition.
So I guess one thing would be where can the AI help me being more ambitious about thinking
about what it could do.
So maybe practically speaking, Patrick, I wrote this in the blog.
I think going through role by role and figuring out what does that job actually do inside
my company for a customer.
And if I replaced it with a really, really, really well prompted AI, could it do it?
And I think that you have companies that are vertical agent oriented companies all over
the place right now.
You have it in customer service.
You have it in SDRs.
You have it in marketing.
There's companies that are popping up, frankly, on the marketing side right now going through
each one and saying, okay, which one of those could be replaced or augmented by AI today.
And then this is a really important one.
What about in six months?
Paul Graham had this tweet that you and I both saw, which was the people that are really
bleeding edge in AI.
You should be building things that don't quite work right now with the models and are
way too expensive because what do you know?
You know that the model is going to get much better in the next three or six months and
you know what's going to get way cheaper at a hundredth of the price or whatever.
So I think maybe role by role can AI do it now?
Can AI do it in six months?
That's probably one exercise that I try to go through for like disruptability of my company
with somebody else.
The second thing that I'd probably be thinking about is ability to be the AI strategy for
another company.
Let's assume most companies are not going to be able to do this themselves.
Can I be their answer to be the foot in the future?
That to me is like a absolutely gold insight.
If your company has that possibility, if you can promise your customers, the world is
changing really quickly, we are your way to deal with that.
That is incredibly valuable, I think, because all of a sudden you have infinite ability to
move out of one spot into more because the AI will continue to be better and better.
And then I think the third thing, and this is not exactly answering your question, but
I do think this is a big deal related to like companies that are going to struggle.
I think anything that reduces your agility in any way, anything that prevents you from
adapting or changing is 100x more painful than it's ever been before.
And this is where I think all of us will start to think of companies, oh my gosh, everything
is a sub cost.
The example that comes to mind here is Satya Nadella in Q4 2022, our mutual friend modest
proposal has talked about this.
If you go back and look at the earnings report, Satya Nadella in Q4 2022 is talking about
the enterprise metaverse.
Okay.
That is discussed on the Microsoft earnings call two years ago.
And now look at what's discussed on the Microsoft earnings cost.
Like we're going to spend a hundred billion dollars on CapEx.
We're doing everything related to AI.
He doesn't care what he said on that earnings call.
All he cares is what is happening going forward.
I think that so many companies are held hostage by what they said to their team or what
they said on an earnings call or what they said is going to happen.
And this willingness or this desire to be consistent with their past selves is preventing
them, embracing the biggest technological change that we probably seen in our lifetimes.
Can you riff a little bit on how all of this change and this frame of thinking makes you
think about individual employees inside of an organization and what they actually cost?
The simple thing would be they cost $150,000 of salary and benefits or something.
But I think you're thinking about this in some new ways, which is beyond just hard direct
costs and is more holistic from the company's perspective related to the customer.
Talk about the cost of an employee and how that's changing.
So you and I have been talking about how there's this meme that's sort of starting to arise
of like small companies, small team meme, small team me, yeah, small team me.
And I think that Dar Mesh from HubSpot talked about this of SMB doesn't stand for small
and medium businesses anymore.
It's answer small and mighty businesses.
So if you start with this premise, maybe small is even better than we thought.
Maybe small is even more of an advantage than we thought.
The question is why?
And I think that there's a lot of hidden costs to having a lot of people.
We've all talked about in the past while coordinating amongst them.
Well, okay, that seems like a hidden cost.
And then there's all the other things that we've talked about in the past.
If you have a lot of people, you would spend a lot of time interviewing and hiring.
You also spend a lot of time putting people on pips.
You spend a lot of time discussing all those very specific things.
I think the bigger picture zoom out that I believe is sort of like how much of your time
is spent dealing with employees in a way that doesn't actually help your customer.
What percentage of your day, if you're a CEO or a founder or a leader, is spent on things
that your customer cares about?
And I think that number is vanishingly and astonishingly small for a lot of people.
This is why I think sometimes you'll hear CEOs that don't even like my job.
Because they don't actually spend that much time doing stuff for the customers.
And I do think that that exponentially goes up the more people you have, or it has the
risk of exponentially going up the more people you have.
I have a friend who runs an organization that's like 400 people.
He was telling me that he had to let go of like 20 people last year.
He's like, it's taken up the most crazy amount of time of setting up how he does the layoff,
figuring out how to talk to each of those people.
What is the severance package for each of those people?
How does he talk to the people that stay?
How does he describe to them what's going on and why it's going to be durable and why
it's okay?
There's just all these hidden costs that go in and they all prevent for a percentage of
time you are focused on delivering a resolution to your customer.
If we envision there's this incredible advantage right now that's pronounced and even more
pronounced than has probably ever been of just people that spend time thinking about what
their customer wants and how to deliver it to them in the best fastest, cheapest way.
And I think that moments that you get to free up your brain to think about that are the
moments that are going to deliver value for your company.
So maybe going back to your question of like, how would I think about the biggest value
creation lever for a company if you were dropped in as the leader and be like, what percentage
of time does the senior leadership team think about how to deliver value to the customer
in the best fastest and cheapest way in six months, 12 months, 18 months, 20 formats?
The lower that percentage is, the more that there's opportunity for that.
There's a massive hidden cost right now.
Are there companies that you know well enough that you would say are exemplars of doing
a great job of the senior team spending lots of their time on what's good for the customer?
I'll give you a couple of examples that come to mind.
I'll give you one that's inside of our portfolio and one that I work with closely and one
that I don't.
Bill McDermott famously, when he took over his CEO of ServiceNow, talked about the number
of customer meetings he had in his first 90 days.
And it was some number that effectively equated to like 10 per day, 10 customer meetings
per day, including weekends.
But I think he said he met a thousand customers in the first quarter that is baffling.
ServiceNow is a huge company.
He has all these things that he has to do.
If what he's saying is true, which I presume it is because he's Bill McDermott and he's
an amazing CEO, that would make me pretty darn bullish about service now realizing what
their customers want and how to go build it for him because the CEO is so incredibly
externally focused.
I love this idea and every company that I am lucky enough to talk to, I tell them like
please be externally focused, one, it's so much more fun, but it's also so much more
impactful to like go and solve customer problems than it is to like deal with internal nonsense.
So that's one.
And then I do think Sierra is doing a really good job on this dimension too.
I think that team is focused on what do customers want?
How can we deliver it to them and how can we embrace AI to the maximum ability?
And I think that means don't do one off things like have AI help you with it.
Anytime you figure something out that can be helped with AI, do it, tell the whole team.
And I think that practically speaking Patrick, I think that it's almost easier for us to
think about the companies that probably aren't doing this and they probably make us have
a little bit of a pit in our stomach like oh gosh.
How is that going to work?
What are they going to do then?
Are they going to go and change?
And I actually think right now being private is a huge advantage.
Is a general matter.
Because you really have to be courageous to not let something that you've said in the
past to a public market investor, not let that stop you from doing things.
You know how big of a fan I am a Fiji, like Fiji will do whatever is right for Instacart.
It doesn't matter if they're private or public.
But there's a lot of people who feel really obligated to their past self and not to do the
right thing for the long term.
I also think it's not a coincidence that the people that are going to do this well are
people that understand customer problems.
But then they also understand the technology of what it can do.
I think the anecdotal experience of AI not changing your life is really dangerous right
now.
Because if you're kind of like math, if you want to be contrarian right now and be like,
God the model is there not that great.
That's fun to say probably like a cocktail party and it fits with people's anecdotal experiences.
But that is dangerous as hell.
Go sit with a bunch of people devoting their lives to this and have them tell you about
the future.
I really believe that is incredibly valuable.
What do you make of this inversion of that old trope that the race was between startups
getting distribution before the incumbents got innovation?
When back to this small team meme like everyone's posting about cursor and companies like
it that are growing zero to a hundred million of revenue with 10 to 30 people in a year.
And actually what's interesting is that you can debate how much better cursor is than
whatever a big company's co-pilot or something.
But they're getting distribution way faster than we've ever seen before.
What do you make of that and what does that tell us about how the future might unfold?
I actually think that that trope that you mentioned was actually like pretty brilliant
for a very long time.
I suspect it still applies a can of startup build distribution faster than a big company
can build product or build innovation.
I actually think it's still the right question.
I think the thing that's probably changed is the speed at which you can build distribution
with a great product has probably gone up.
The willingness for somebody to adopt something that feels like magic.
Maybe that's the point.
I think that AI can make your product feel like magic.
And I think people are really willing to adopt things that feel like magic.
So the speed that a really well executing startup that produces magic can get distribution
is probably higher than it's ever been.
Would be my guess.
I'm not enough of a student of this to know that for sure.
But I do think they are producing magic.
The thing that is actually interesting though if you're a startup just to make it real
is if somebody has distribution already and they thoughtfully deploy AI and they actually
go and disrupt themselves and they actually put it into their product, they're even harder
to compete with right now.
I think that Microsoft is way harder to compete with now than it's ever been before because
they have this ridiculous distribution, insane distribution.
And they are really pushing to get AI into their products in a way that feels like magic.
I think that no one doubts that's at the end of the day gets this.
Nobody wonders about whether they get it.
The only thing that limits their speed is like their organizational size.
It's not intestinal fortitude from Sutthia.
I think there are other big companies that you really worry that they like actually are
not going to be able to get the product in because they're going to let organizational
stuff get in their way.
I actually think it's still the same question.
I just think that if you're a big company, you better be awfully paranoid about a startup
because their ability to build distribution is way faster than it's ever been.
And I think that if you're a startup, you better be really clear about who you're going
up against. There is a massive difference in speed amongst the big companies at how
quickly they are leveraging their distribution of data.
It's becoming popular to say be an AI first or AI native company for startups.
It kind of obvious what that means.
What does that mean for a 10,000 person public company that sells software or provides
a service or is a white collar-ish company or something like that?
What would you recommend those CEOs literally do?
Not like a mindset. First 100 day presidential plan, we're going to become AI native.
What does that mean?
You and I have talked about in the past, this idea of enthusiastically rehiring somebody
is the standard.
If you could do it again, would you hire this person to do this job?
I think you have to enthusiastically re-underwrite your business and what do I mean by that specifically?
You need to go and say what is the purpose of your company for these customers?
What is the best, fastest and cheapest way for us to go and deliver that?
Is it what we're doing now or not?
You can hold nothing sacred.
What do I mean specifically?
Let's take pricing.
Today, a lot of companies have seat-based pricing models.
I don't believe that that will be the future of the way that people buy software.
I think that there is something we've heard from different people, but maybe they're
going to pay for the job to be done.
Maybe they're just going to say I want this piece of work done and I want to pay just
for that piece of work done.
I don't want to pay for each person that uses your software.
I want to pay only when something gets done.
Well, that is a massive and dramatic shift if you're a big company to move away from
the pricing model that got you there.
But understanding that that might be the future of your pricing, that is a big realization
that has a bunch of knock-on effects as to like, well, what do you go do then?
And maybe it means you'll have 60% less revenue now if you move to that.
But in the future, you have the potential for 5x more revenue because you have a bigger
customer base that you can go after or you can do more jobs for somebody.
But I think one thing that you can hold nothing dear, that's one thing, which is pricing
model, has to be evaluated.
All under this idea of enthusiastically re-underright, the way that you're delivering the purpose
of your company to its customers.
That's why.
Two, I think that you do have to go roll by roll and figure out what is this AI superpower
version of each of these roles.
Is it that it's replaced, is it that it's augmented, and I think that that is a big deal
of like the specific role by role conversation.
And I know people like, well, we have 5,000 people, I don't even do that.
Like, can you tell me what's more important than that?
What is more important than figuring out whether you have the right people doing the right
jobs for your company?
So that's that.
I think the third thing, Patrick, is this idea of what percentage of our time do we spend
thinking about our customers?
I really think that's valuable.
You know this thing that Shopify does?
Shopify will just kill meetings and recurring meetings randomly.
I think doing the calendar audit of what percentage of our time as a company, as a leadership
team, first as the CEO, then as a leadership team, then as a company, is spent on things
that move the needle for our customer.
What percentage of time do our engineers spend coding?
All these things I would do, and it's easy for me to say because I don't have the responsibility
of doing this.
You asked, what would you suggest to somebody?
It would be that.
And then I think the last one, which is maybe the most optimistic, is like, what have
we dreamed about providing for our customers that was impossible before?
And let's all use this idea of what is barely possible now and too expensive.
Oh my God, that's going to be possible in six or 12 months.
Let's go build that.
One of the things that you and I have been talking about separately is how much should we
care about margins right now?
Well, it actually means you should care a lot about margins in certain topics and not
a lot about other topics. If something's like an AI first product, you probably shouldn't
care that much about the margins of it because it's going to get so much cheaper to deliver
that.
Whereas if something's not an AI first product, you should care a lot about the margins
because that is the durable future.
Those are a few things that I think I would do and I would suggest to people to do.
And I also think anything that prevents me from being agile.
I know I keep on coming back to this.
Anything that prevents me from making a change, I would try to write down and figure out
how I eliminate and maybe that means you don't provide guidance anymore.
Maybe it means that you tell people like there's going to be a negative and then there's
long term going to be a positive.
Maybe it means that you tell your team that we're in the midst of a big change and like
some things are not going to be as predictable.
You have to be able to make the changes you need in the company and it's hard to predict
those changes right now.
And so I think you need to like give yourself the ability to be very, very, very nimble.
What would you say to a leader that said okay, I get it.
This is cool.
I love using chat GPT on the weekends.
I get why this is interesting.
But I'm scared that I'm going to like pivot my entire battleship of a company in this
new direction and it's a wild goose chase.
It takes longer or things change too much and it doesn't actually work in production
use cases and I'm going to waste my next two years chasing this thing like I'm going
to chase the metaverse.
There's no there there.
It's just like it was a waste of my time and I screwed up the company as a result.
And I'm willing to eat years to wait and see where these things get and where the equilibrium
settles out and wherever that Jeffrey Moore third cat not early adopter not early majority
like the next one.
I'll be the one of those and I'll be fine.
It is so easy to say when you're not in the seat.
I want to recognize that my response is as you can't outsource your conviction, which
means don't do it because somebody tells you.
I do think before you come to that conclusion, you owe it to yourself.
To spend weeks or a month really trying to convince yourself that you're wrong.
Because I think this is the point that I feel most strongly about go figure it out for
yourself as to what's actually happening with a lens of trying to break your prior thought
on it.
It's convenient to think that you can just gradually get into this.
It is really convenient to think I'll just figure it out later and I'll do it in a gradual
way because that's just way easier for us to deal with as people and I think any time
you have a convenient belief on something important, you should really examine it and I think
in this case examine that convenient belief and if you really after a month of being super
open-minded and really trying to break it, you come up with that great, do it, but do
it affirmatively.
don't do it because it's
the convenient path that allows you to not have to change very much, you and I are both NBA fans.
It is really hard for an NBA team to be like really good for a long time and never bottom out
before they get to be good again. It's really hard to just keep it going and reloading and reloading
and reloading. It usually has a really painful period afterwards on the bulls fan. Look at the bulls
like jeez. It's very convenient to think maybe I'll just be able to do it both ways. I'll just be
able to stay good and then I'll just figure it out and I'll get the second track and we'll make it work.
Maybe, but I would affirmatively really try to figure it out by trying to break it in your own mind.
One of my favorite points that you wrote about and that you and I have talked about is whether or not
you're treating these things like you would a genius that just joined your team that has the
capabilities. Forget six months from now, just the capabilities that it has today. If that person
showed up at your office and you're paying them, how would you treat them? Are you treating
these models and their capabilities in the same way? I love that thought experiment. Can you
flush that out? Yeah. I think we have a standard for these models that is so insane right now,
which is effective. If I just ask you to do something and I'm not clear in what I'm asking you and
you don't know anything about my company, do you just make it happen? If you don't get it the first
time perfectly, I base on my math. This thing doesn't work. The thought experiment you and I are
talking about is what if you just like knew the person was brilliant and you knew that they would
work 24 hours a day for you and you just knew that they had this crazy potential. The first time
they messed up, you wouldn't just be like, oh, they suck. You'd be like, I got to do something
differently in order to get them most out of this person. That would just totally be the reaction.
And instead, I think we are treating the models like they're like someone's nephew that we had
to hire. It's like, no, I gave him the chance and I knew it. He sucked. The mental model of no,
this is the person that you fought like crazy to hire and you were so lucky to get and you didn't
think they were going to come. And the first project was it perfect. It's like, no, I'm going to
make this work. That mental model is so different and so much better and frankly, we have so much
positivity for your company. I really like that mental model. And if something doesn't work right
with the model, it's your fault, not the models. It's not a question of the model's capability. It's
a question of your prompting and your understanding and your ability to give it context. Context is
going to grow even more important here. And I think most of what's missing from the models in order
to be magic for you is context. Part of the reason I think that HRSA and cognition,
some of these other companies have done so well is they actually have shared context of the code
base and then they get better and better with the more work that they do alongside of you.
I think what's missing a lot of times with what people try to get out of the model is giving it
enough context for it to be great. The relationship idea here would be like, the relationship most
of us have the most shared context in is the one with our spouse with your spouse. You can like
flicker your eyes at a party and they know it's time to go. You just have so much shared context that
the smallest movement of the way your eyes look, the length of a blink, all of a sudden they know
everything. Avni can perfectly tell what I will think about something without me even being
there. She can perfectly imagine what I will react to something with. That's because of a lot of
shared context and I think my point on envisioning these models as a collaborator and now take that
to work. There are people you've worked it for a long time or like they just know what you're
going to want. These models I think can and will be able to do that as collaborators but we have
to give them the context. I think the only way to really lead through this is to lead through
optimism. Like the only thing I didn't like about the title of this recent blog, it sounds negative,
AI or die and I'm kind of like remember, yes, if you don't embrace this, your company has a real
risk of fading into a relevance. But you can live in a way that you never thought possible. You can
make magic. You are here to make magic for these customers and you actually now have the tools to
do it. That's the part that I really believe has changed in my thinking on it which is if you
approach this with optimism, dude, what a time to be alive. What a time to be alive.
I love Tyler Collins idea that most of his writing now is for AI's not for humans, that he is generating
context that will make them better for him in the future. I hope that there's more and more ways
that make it easy to do that. I think lots of people that are optimistic about this would very
quickly opt into something that generated more context in an easy way, low friction way for
these things to work with. And I love that idea. Think about context and how much you have already
and how much you're building as part of preparing to use these things really well. I also really
like your idea of the difference between a world class predictor and a world class reactor. Can
you talk about that new dichotomy? It's such a perfect question for me because it gets to merge
together things that I love that may not seem like they have anything to do with each other.
But the first person I heard say that was Coach Kay at Duke. He said, "I am not a world class
predictor, but I am a world class reactor." And he was referring to it as like when college
basketball changed from people that stayed for four years to people that played for one and then
go to the NBA. He was like, "I couldn't have predicted that that's the way the rules would go.
I didn't know." But you know what? Once that was the game on the field, I played it extremely well.
That actually was very helpful for me, Patrick, along with Coler's quote, because it's very
intimidating to think about predicting the future. There are really smart people in Silicon Valley.
There are really smart people all over the world. I don't know how to predict the future.
I do not have the IQ points for that. There are people that are much brighter than me who can do that.
I think the thing that I do have in my control is the ability to respond quickly to new information.
I can control that. I can control being open-minded to seeing new information and then reacting quickly.
I can control being averse to change. That is something that it feels empowering to me.
And it's something that's in my hands and it's in the team's hands too. I can help the team be like,
"Guys, let's embrace this change. Let's embrace this reality and let's go react to it."
I think right now, the world is totally awesome for people that can be world-class reactors
rather than world-class predictors. If you look at the people that created these labs,
they were world-class predictors. That was an amazing insight, however many years ago,
look at what the scaling laws are going to do, look at these exponentials,
and they themselves funny enough or sort of humble about it. They're like, "It wasn't that hard.
If you just believe that the scaling laws continue, you could bet that this was going to happen."
I'm like, "It was hard." Looking at what a model can do today and being like, "That's going
to be cheaper in the future." That's not being a world-class predictor. That's just looking at
the facts. What is hard is choosing optimism to go and react to that, but it's totally within our
control. It's hard the way going to the gym is hard. It's not hard the way creating a new mathematical
theorem is hard. It takes discipline and it takes fortitude and it takes a choice. But I love those
kinds of things because those are in our control and they don't require a new brain. They require
more discipline. That's something all of us can do. What do you think you would have done if you
zoom back, you picked the moment, to the most intense operational trenches that you were in at
Instacart. If you had this set of tools back then, do you think that would have been like? How would
you have used them? If we take our logic of work from the customer backwards, one thing I think that
we were good at at Instacart and Instacart still get at a percentage of time basement thinking
about the customer. I don't think there's a huge optimization on that. I do think that figuring out
the most abstracting of what does a customer want? A customer wants to save the trip to the store.
They don't want to go and they want to be able to be at home when they get it. When I was thinking
to your point, having these tools, the better, faster, cheaper version, I would be trying to make
the order use as much context as I could to make their ordering process be as fast as possible
and to make sure that their order is delivered as accurately as possible. True like main thing
things, and when I say make the order as fast as possible, I would be trying to do stuff where like
their last grocery order is something that I can ingest in some way, even if it wasn't on Instacart.
And so therefore, I can as quickly as possible get them through to where they can check out.
So that's one. And then on the like as accurately as possible, I'd be trying to be better at
figuring out what's in the store right now so that I never show them something that they're not
going to get. And then on the delivery side of it, I am not technical enough to tell you the optimal
batching strategy that would be used using an LLM. But whatever I could do to cut off minutes off
that delivery, I'd be trying to figure out what is the AI way of doing that. And then maybe the other
thing I'd be trying to do is like, is there something we can do like over the phone that's now
not economic today that will be economic in the future for people that don't want to do it online.
But want to just call older people maybe aren't as familiar with the app. What can I do to make it
where it feels like magic for them of like, I want these groceries. Okay, cool. Then they show up.
What you're saying though has like a very embedded thing that's very real, which is the more your
product is physical. The more the bottleneck for using the AI is the physical world rather than the
software world. And I do think it will be slower as there are constraints that are physical in nature.
The AI is not fixing traffic today. It's not making a human being run faster through the store.
I think figuring out whether your constraints are physical or whether they're like software-related
digital. I think the more digital only you are, the faster this will come and create magic. It's
sort of like this either you're going to create magic or someone else is going to create magic with
a lot fewer people than you. And the customer is going to expect magic. This Bezos thing of
customers are divinely discontent. They are just going to expect, we already do this. We are
going to expect magic from every experience. And either you're going to deliver it or someone
else is going to deliver it. But that's the new standard. We've talked a lot about the role of
status before in all things. Apply your ideas about status.
in our status seeking nature and behavior to this new world.
- This has been observed in the past,
but I think sometimes there is historical status
in business to like the size of the team that you manage.
Sometimes still today, how many people do you have
is a question that is asked to like a startup founder
as some indication of progress
or the scale of your company.
How much money have you raised?
How many people do you have?
- I think if you take this idea that you talked about
the small team meme or Darmash's idea
of small and mighty businesses,
it seems possible that the new status is to having a small team.
The ratio of magic to people
and I think magic sure it can be like measured in revenue
if you wanna use a very blunt instrument,
but like maybe this idea of magic per employee
implied being like, oh my God, you did that with 10 people.
That kind of thing.
- Can you feel that already?
That feels like that shift has happened already.
- I think so, and I think that if it's happening,
that's great.
And it's not because that means people will lose their job.
That's not the point.
The point is that each person will deliver more magic.
They might leave a bigger thing and start a smaller thing
or join a smaller thing and have more impact,
have more purpose.
Nobody likes being a cog in the wheel.
Nobody likes feeling like if they left, nothing would change.
And I think that the more we can get to people
like getting more out of their potential,
that would be freaking awesome.
It does seem like it's starting to go that way
and I think that is an awesome thing.
Small teams feeling like they can do anything.
Oh man, there's nothing that stops us from doing that.
I think that would be an awesome thing for the ecosystem.
And frankly, I think that this is conflating two things,
but most companies are probably way too big
relative to what they need to be public companies.
There's no way that most of these companies
will run efficiently right now.
Even without AI, you have this thing
that these companies are bloated relative to what they should be.
I think now you factor in AI,
you actually have a real reason to change that
and to make yourself lean and customer oriented
and seeking of magic.
But I do think that this idea of the new status
might be a small team.
I think that's very possible.
How are you changing your investing as a result of all this?
Whether that's the way you look for companies,
whether that's the way you underwrite a company,
whether that's attributes of a founder
that are changing, some of these things
are the small team meme companies.
If you look at the price of the equity,
the valuations that they've raised at is it's high,
nominally, they're growing insanely fast.
It's hard to know what they should be priced at.
Are you changing your valuation expectations?
Like what are all the ways in which you think you're actually
approaching things differently than you did two years ago
or something?
One of my favorite concepts that I've heard,
I don't know who the first person was to say this,
the first person I heard it from was Pat Grady,
you know, my partner, which was we invest in slope,
not in our set.
I guess if I really take that as the logic,
I think that's still very true.
I think the thing that is possible is that
for the best companies, the slope can be way different
and the slope can be way steeper.
And I think if you take that to its extreme,
that means that for the best things,
sure, like you should be willing to pay more,
what I think it really puts a premium on those,
be earlier into those companies,
figure out what those things are gonna be.
And I think that what that then comes back to is like,
okay, what are the attributes of the people
who are building them?
And I think that comes back to some of the stuff
that you've talked about and we've talked about,
but like I mentioned ambition,
I mentioned curiosity, I mentioned resilience,
I mentioned adaptability.
You mentioned imagination in there.
I think that's a hugely important word
for thinking about this.
So figuring out people that are close to what this can do,
optimistic about what it can do,
have some imagination and then are also adaptable as hell,
because it keeps changing.
When it changes, the only thing that you keep dear
is like the obligation to deliver magic to the customer
and everything else can change.
Probably the bigger thing I would add to my list, Patrick,
is in the past, I think resilience grit,
those are things that have always been there
for any founder that you like really want.
I think the thing that I do believe is newly important,
it's always been important,
but more important for me is the like agility adaptability.
It's the world class reactor point.
It is the willingness to change on a dime with new information
and the desire to go and figure out that new information
and to never hold a convenient belief into examine it.
That's probably new and that combined with more slope
for the best ones.
I think that what's gonna happen,
the best companies are gonna be worth more
and the mediocre ones are gonna be worth less.
I just think the gap is gonna widen
and that is exciting and intimidating
'cause you better get it right.
- You get to sit literally at ground zero
of the community of people that are investing
in these companies, probably could be well argued
that any company raising is going to Sequoia first
or amongst a handful of firms that they're going to first
and would love to take their capital if they could.
You get this complete tip of the spear view into this world.
If the class of investor in Silicon Valley
draw radius around your office is wise to this,
does that mean that maybe the better way to make money
as an investor is to be like a private equity investor
in New York that just appreciates this more
than your peers do who aren't in the center of things.
They don't watch cursor happening.
- I don't think it's better.
If you believe this is true,
I think there's multiple ways to express it.
So maybe a few different ways.
One, I think if you are an investor in early stage companies
and you pick the right founders building the right things,
I think the upside is better than it's ever been.
That I think is an amazing place to sit
and it's about picking the right people
and being lucky enough to have them pick you.
So that I think is still an incredible privilege
and lucky place to sit.
I genuinely believe that.
I think that if you are someone who doesn't sit here,
there's different ways that are really good to make money.
Figure out the public companies
that are actually going to embrace this.
I think that Mark Casey at Capital Group
tells this great story from a long time ago
of how during the beginning of the internet era,
he was really impressed with how Home Depot
was thinking about this.
And his example was we went through item by item that we sell
and we figured out the price of the item relative
to the cost of the shipping and we specifically went through
and we are tracking that over time,
but the ones that are most relevant for internet sales
are the ones where this ratio makes sense for a customer.
And we will continue to update our opinions
as we figure out shipping costs go down
and we might choose different products
if customers want to buy it though.
I thought that suggested they were ready for a world
where people were in a shop differently than they were
in retail and I suspect Mark did really well
on an investment in that company a long time ago.
By the way, one of my favorite episodes, of course,
was with Ken Langone.
There was amazing.
And the Frank Blake one too.
But anyways, figuring out what public companies
are going to embrace this,
what kinds of people are going to embrace this?
Big deal.
And then I think on the private equity side,
my instinct is encouraging those CEOs
to get closer to what this can do
and having that come back and impact their business.
The reason I laughed, I was laughing a little bit
when you asked because the shared delusion
of the how we're using AI slides in a board deck
that everyone sees as the board member
and produces as a operator,
is probably one of the funnier things out there right now,
which is some 20 to 30% reduction
and some sliver of your business to be like,
"Hey, board, don't worry, we're using AI."
And the board's like, "Okay, cool.
I'm glad you're using AI."
Nobody really thinks that's enough
but everyone's doing it for each other.
I would say that one way to, I think, make money
is the more that you're not doing that,
the more that the companies you work with are.
Either we, hey, we've looked at it,
it doesn't work for us, here's why,
or this is a huge deal for us.
What should board members do?
This seems actually potentially a really big problem.
If you're a public company, well-paid board member,
maybe on some prestigious company,
a lot of these roles are not hyperactive
and influencing the business
and they're sort of governance bodies
that sometimes don't do much.
What is the risk and opportunity set right now
for board members of these companies?
- I'm like a fuel person on a lot of stuff.
If you think about the only real job of a board
be on some very highly legal, corporate governance stuff,
it's like, do you have the right CEO?
And if you're on a board right now
and you just see how you feel at each company
you're on the board of, do you have the right CEO?
- You feel amazing right now if you have the right CEO.
- Truly, this is a place where I feel very,
very, very lucky, which is, if you have a right CEO,
you're like, okay, cool, they're gonna ride this way.
They're gonna figure this out.
They're gonna go embrace this.
If you're a public company board member
and you don't have that feeling right now,
I think you gotta examine why do you not have that feeling
and what are you gonna do about it?
And ideally what you do is that person is somebody
who actually does wanna embrace this
but is nervous about something board related
and what you wanna do then is appease their fears.
Of like, no, we want you to go and play.
We want you to play free.
We want you to go figure this out.
I think that if you don't have somebody
who wants to embrace this not because of board fear
but because of their capabilities
or because they don't wanna play in this next chapter of the game,
like, you gotta figure that out.
I definitely think as a board member,
remembering that you don't get to help in a lot of ways
on a public company board,
but the one or two ways is really asking a good question
every once in a while that makes a big difference.
This is a good time to ask one of those questions
and see how you feel in a world of accelerating change.
This is something Doug Leoni would always say,
he would talk about the accelerating change.
I will add the second part.
In a world of accelerating change,
how do you feel about the person leading your business?
You probably either feel like amazing or you feel nervous.
Are there any other conversations
as you've processed this change
that most stand out as interesting
notable. What other conversations have you had that most impacted you in the last
say three months? There has been a bunch. Maybe I'll describe it more as like
the spirit of the conversation. This is probably the thing that I really hope
comes through the most. The conversations that have been the most impactful to
me all have this element of insane humility in them. Which is wow. There is a lot
happening. I don't totally understand it. I need to go and figure out more. All of
them. They're not assertions as much as they are curiosity. There's so much of
like, oh man, there is a lot going on. I got to get closer to the metal. I
got to do more truth seeking. The conversations that have been the most
interesting are all like that. There are people that are really trying to like
listen. There are people that are really trying to get closer and they are all
people that are sort of, you know, confused is the right word, but certainly like
man, there is a lot going on right now. And that humility is probably the
thing that I most attracted to in a conversation right now about these topics.
Which is, here's what I know. Cool. Now like I just want to figure out a bunch of
stuff. That's why I come back to like, don't outsource your conviction. Don't do
something because I think I believe something. Do something because you believe
it. But we'll try to figure it out. I think that the people that I respect the
most, I heard one time that the Colossans, I remember who said this, but they said
they listen with predatory curiosity. Think about that language. I really need to
know what you're saying and why you're saying it. I think right now people that
are going to do great things are really willing to change and very much very
curious, very humble. I love this story. Shane Badi, I told you about his career
training when he was young and this idea of the ghost. Can you relay that?
Because I do think it's as an analogy, an interesting way to think about what's
happening here. Shane Badi, a foreign professional basketball player and a dear
friend. He's very different than most people and that when he was growing up,
he sort of knew he wanted to be an NBA player and was working accordingly to do
that from very young age. A lot of kids say that, but they're not serious about it.
I think Shane describes himself as like I was like a professional basketball player
from the time I was 10 years old. I went and did these things. I was working. I
was working with the goal of life. So he tells this story of there was a poster in
his room and the poster in his room had basically like somewhere, somebody is
out there working while you're not. Somebody somewhere is out there practicing
while you're not. And Shane would talk about how that haunted him. There was
this ghost that was out there and it would make him work hard because it's like,
gosh, if I take a break, there's somebody out there who's doing it. So he tells
this story and of course it like ends well because he plays in the NBA and he ends
up being amazing and he has this 13 year career and it's like the value of hard work.
But the thing that's so interesting is Shane met the ghost. When he played the NBA,
Kobe Bryant was that ghost. Kobe Bryant was working all the time.
Kobe Bryant was born a month after Shane. It's crazy.
Grew up in Italy. He wasn't like around the corner in Michigan. There literally was
someone on the other side of the world working all the time and then he comes face to face with
this guy and he was out of this world. Good. And that was how Shane had to ultimately
measure himself. As we think about this moment in what's happening, there is someone out
there working right now to produce the magic that you promise to your customers.
There is someone out there working on it and they are working on it a lot.
You're going to come face to face with them because your customer is going to decide at some
point. Do they want to work with you or do they want to work with them? You got to approach
that with joy. You got to approach like I'm going to come face to face. I'm going to go earn
the right to play against this person and I'm going to be amazing. And I'm going to go and
take this opportunity because I'm given this chance. But that reminded me so much of this moment
for a CEO or a leader or anything. The ghost is out there and you get a chance to play against
them. But you got to embrace it and you got to go do it because the ghost is good.
I think it's helpful to think about what's happening from both directions, from both the lens
of opportunity and the lens of risk. And if you think about the title of your post AI or die,
I think one represents opportunity together represents risk. Even the story about Shane,
two sides of an interesting coin. Maybe in closing, talk about the optimistic side of this.
I know that this is your primary takeaway, that this is a tremendous opportunity for the right
kind of people. And then it will lead to lots of fascinating things and products and companies
and careers. Maybe just try to put a bow on this for us. You've thought about this a lot now.
You're talking to these founders every day. You're working with the investors that get this the most.
What's your summary of this entire exploration? The post starts with this quote from
Ertencena, which is that this is a moment where you can actually pass a bunch of cars in front of
you. And I think the reason that that creates the optimism for me is you are only limited at this
moment by the scale of your ambition. This is something Rulaf asked a lot of founders, but like,
what is the scale of your ambition? This moment, you can go and pass 15 cars in front of you. And
remember, like you get to decide what race you're in. So if your company's worth $10 billion,
this is a chance for you to be worth $100 billion. And if your company's worth $3 trillion,
it's a chance for you to be worth $30 trillion. And if your company's just getting started,
you have a chance to beat people that you never thought you'd have a chance to be. You get to choose
the racetrack. So the reason that I think there's such an incredible optimistic moment here is there's
going to be a bunch of change. None of us want to live in stasis. None of us want to be stuck where
we are. All of us want to have upward movement that comes from doing something great and like earning
it. This is a moment where if you earn it, if you are willing to go and learn this stuff and go and
just be committed to being excellent, the world is available to you in a way that it's never been
before. You don't even need to hire a lot of people think about all the constraints that existed
before. If it's true that a 20 person company can do something that a 20 person company can never
do before, it's so much easier to find 20 awesome people than it is to like run a 10,000 person
org that's so far away. You can do it faster. The thing for me is like for high agency ambitious
people, you've been given tools to like go into a race you never knew possible and to fucking win
it. That is so awesome. That is what I hope people get. It's not, yeah, sure. If you choose stasis,
yeah, you might go into a relevance. But if you choose optimism and you choose forward motion and
you choose embracing this, there is no limit to what you can go and do. And that is the what a time
to be alive thinking. That is the thing that makes you excited about your kids. Oh my gosh go back
to what Sam said. Every person in a decade will be more capable than every person now. I mean,
that's awesome. Now let's go get it. Our mutual friend Sam Teller, one of my favorite people,
has this line that always has stuck with me, which is if you just see excellence in people at the
highest level, it's a huge competitive advantage because you just have this bar that you can walk
around with and compare things to and make better decisions and work with better people. And it's
all about having seen the highest level of excellence that you can. I feel like my takeaway from
your post is that actually we've democratized this. We've all had a chat GPT aha moment experience
or several amid journey experience, whatever. And the imperative that I take from your post is we
actually should all not rest until we've created one of those in our business. We should have a
moment that wows us in our own product in the same way we've been wowed by some of these incredible
original products. And until then we shouldn't rest and then we should keep going. And I just think
a writing is such a cool call to action for an exciting wave of the market in the market economy
and companies. So thank you for writing it and thanks for outlining with us today. Absolutely,
thank you for having me. If you enjoyed this episode visit join Colossus.com where you'll find every
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you
Podcast Summary
Key Points:
AI is rapidly advancing, disrupting traditional business models and making past constraints like headcount and rigid processes obsolete.
The most impactful shift is moving from being a "world-class predictor" to a "world-class reactor"—focusing on agility, adaptability, and quick response to change rather than forecasting.
Companies that embrace AI and prioritize customer-centricity, speed, and operational flexibility will outperform those stuck in legacy structures.
Small, nimble teams are gaining an advantage over large, bureaucratic organizations due to faster decision-making and higher per-employee value creation.
Leaders must actively challenge their assumptions, foster curiosity, and cultivate resilience and adaptability to thrive in an AI-driven era.
Existing business models, such as seat-based pricing, may become outdated as AI enables pay-per-job or outcome-based pricing.
Real-world AI use must be grounded in rich context and shared understanding—especially in customer-facing roles—where collaboration and clarity drive results.
Boards and executives must evolve by questioning leadership agility and ensuring alignment with rapid technological change, rather than maintaining outdated protocols.
Summary:
The rapid evolution of AI is fundamentally reshaping how businesses operate, forcing a shift from traditional metrics like headcount and past performance to agility, adaptability, and customer-focused innovation. " This mindset enables organizations to become more agile, customer-centric, and resilient. Small, nimble teams are gaining a significant edge over large, bureaucratic ones, as they can respond faster and deliver more value per employee.
Leaders are urged to reevaluate core business models—such as pricing and roles—through an AI-lens, questioning whether current structures still make sense in a world where AI can perform complex tasks at scale. Real value comes not from isolated AI experiments, but from embedding AI into daily operations with deep context and shared understanding. Companies that embrace these changes will outperform those clinging to past practices.
For investors, this means prioritizing founders with ambition, curiosity, and adaptability, and identifying companies that are not just adopting AI, but actively redefining their value propositions. Boards must evolve from passive oversight to active enablers of change, asking critical questions about leadership agility. Ultimately, the future belongs to organizations that prioritize speed, innovation, and customer value over size and tradition.
FAQs
Ridgeline is a unified platform that automates complex tasks like portfolio accounting, reconciliation, reporting, and trading compliance, reducing headcount and risk by streamlining operations across the entire investment lifecycle.
Crosby AI uses custom AI agents to provide fast, detailed legal advice—such as identifying key negotiation points in 43 minutes—enabling faster deal closures and reducing the time and cost traditionally associated with legal review.
Ravi argues that AI's rapid advancement will force companies to either adapt quickly or become obsolete, emphasizing that traditional metrics like headcount are outdated and agility, not predictability, will define future success.
Companies should conduct role-by-role assessments to determine if AI can perform current tasks now or in six months, and evaluate whether their business model—like pricing or customer focus—needs to evolve to stay competitive.
A world-class predictor tries to forecast the future, while a world-class reactor responds quickly to new information. Ravi believes agility and adaptability are more valuable than prediction in the current AI-driven era.
Leaders should use AI for real-time, strategic tasks—like deep research on a company before a meeting—rather than for basic summarizations, to gain deeper insights and improve decision-making.
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