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The Logan Bartlett Show / episode intelligence

EP 150: Bret Taylor (CEO, Sierra): A New Class of Software Winners

12 Sept 2025 8 published claims 0 attributable people
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8 published records

01 / prediction

All of a sudden the total dressable market looks huge because the addressable market of legal advice and legal labor is actually quite large. So that's really interesting to me because I think the traditional perception of where there are addressable markets in software I think has been upended because agents aren't simply productivity enhancements for people, but actually doing a job.

“All of a sudden the total dressable market looks huge because the addressable market of legal advice and legal labor is actually quite large. So that's really interesting to me because I think the traditional perception of where there are addressable markets in software I think has been upended because agents aren't simply productivity enhancements for people, but actually doing a job.”
Speaker
Not verified from transcript
Publisher
The Logan Bartlett Show

02 / prediction

sudden you look more or less profitable even though I was laughing about accounting it's like it's like the cash flow is the same but all these numbers shift around and then on top of you have to have be a great storyteller and bring your employees along with you your investors along with you your your your customers along with you it's formidable I'd say I said you know I think a lot of entrepreneurs are like yeah we're gonna you know disrupt the incumbents that actually sort of funny having sat in that seat for a while I have a ton of empathy and I think some great leaders will come out of this and and just like the reputation such a house for transitioning Microsoft into the Azure cloud era but it is absolutely not a fair going conclusion in fact I think you know for most of these incumbents the defaults will be that they will be disruptive they don't embrace you know where software is going you've talked about this in the past and you kind of alluded to it there but the the business model elements of it seem far harder with all those constituencies you talked about shareholders and employees and customers and just managing expectations and and taking people through all the acco

“sudden you look more or less profitable even though I was laughing about accounting it's like it's like the cash flow is the same but all these numbers shift around and then on top of you have to have be a great storyteller and bring your employees along with you your investors along with you your your your customers along with you it's formidable I'd say I said you know I think a lot of entrepreneurs are like yeah we're gonna you know disrupt the incumbents that actually sort of funny having sat in that seat for a while I have a ton of empathy and I think some great leaders will come out of this and and just like the reputation such a house for transitioning Microsoft into the Azure cloud era but it is absolutely not a fair going conclusion in fact I think you know for most of these incumbents the defaults will be that they will be disruptive they don't embrace you know where software is going you've talked about this in the past and you kind of alluded to it there but the the business model elements of it seem far harder with all those constituencies you talked about shareholders and employees and customers and just managing expectations and and taking people through all the acco”
Speaker
Not verified from transcript
Publisher
The Logan Bartlett Show

03 / evaluation

u 10 million dollars but if you roll that out that year it would go down to two hundred thousand dollars how do you actually do that if you're a public company that's really hard just because like all of a sudden you're going to look like your business is slowing down even though you're just eating your vegetables for a greater you know a brighter future if you're a not unprofitable or not cash low positive start up you know all of a sudden just your burn rate you know go way up if you have let's say none of those applied you're a private company that somehow is ready for all those things all of a sudden to do your employees like you know jump ship in the middle because they're betting on the the come and you just look at the transition from like windows revenue to azure active directory each one of those is a ground game at the customer by customer level to sort of transition people into that new world and it's so easy for you know armchair strategist like of course that's the correct thing to do and then the question is like well if you don't care about the messy middle yeah it's totally obvious but everyone in the world cares about the messy middle so it requires just incredibly

“u 10 million dollars but if you roll that out that year it would go down to two hundred thousand dollars how do you actually do that if you're a public company that's really hard just because like all of a sudden you're going to look like your business is slowing down even though you're just eating your vegetables for a greater you know a brighter future if you're a not unprofitable or not cash low positive start up you know all of a sudden just your burn rate you know go way up if you have let's say none of those applied you're a private company that somehow is ready for all those things all of a sudden to do your employees like you know jump ship in the middle because they're betting on the the come and you just look at the transition from like windows revenue to azure active directory each one of those is a ground game at the customer by customer level to sort of transition people into that new world and it's so easy for you know armchair strategist like of course that's the correct thing to do and then the question is like well if you don't care about the messy middle yeah it's totally obvious but everyone in the world cares about the messy middle so it requires just incredibly”
Speaker
Not verified from transcript
Publisher
The Logan Bartlett Show

04 / prediction

The thing that we've seen just time and time again technology though is you know there's all the fancy names for innovators dilemma crossing the chasm I can't remember what they all mean anymore but you know effectively when you're an incumbent you sort of become addicted to your product and business model and as a consequence when there's a big platform shift underneath you you end up usually with a graveyard of companies who usually for business model reasons couldn't make that transition seabull systems with on-premises software relative to some company like Salesforce you could see the you know companies like Microsoft you know had fits and starts with the internet and cloud and came out quite strong and so if you're big enough you get multiple out that's you know with with these transitions so my guess is we will have a few stories you know maybe maybe a such a level story of a company that came out even stronger on the other side of it and we'll have some stories like seabull systems you know of companies that saw the slow motion car wreck in front of them and couldn't turn the wheel fast enough just because of the natural gravitational forces that they keep large companies

“The thing that we've seen just time and time again technology though is you know there's all the fancy names for innovators dilemma crossing the chasm I can't remember what they all mean anymore but you know effectively when you're an incumbent you sort of become addicted to your product and business model and as a consequence when there's a big platform shift underneath you you end up usually with a graveyard of companies who usually for business model reasons couldn't make that transition seabull systems with on-premises software relative to some company like Salesforce you could see the you know companies like Microsoft you know had fits and starts with the internet and cloud and came out quite strong and so if you're big enough you get multiple out that's you know with with these transitions so my guess is we will have a few stories you know maybe maybe a such a level story of a company that came out even stronger on the other side of it and we'll have some stories like seabull systems you know of companies that saw the slow motion car wreck in front of them and couldn't turn the wheel fast enough just because of the natural gravitational forces that they keep large companies”
Speaker
Not verified from transcript
Publisher
The Logan Bartlett Show

05 / prediction

look at something like log code which is kind of saddened between being the foundation model and the actual application itself I guess where you said you have an interesting purview of both you have a board seat with open AI and then you also have a company is there any way that you you think about that and like where companies can exist as applied AI systems on top of foundation models versus where foundation models are going to capture value I'll give sort of one framework that I think about the technology evolution which is in the early days of a new technology whether it's the smartphone or the web browser in the early days of the technology adoption cycle a lot of the value and as making it just work like it's it's hard to make a website or a database that scales to consumer scale on a website that was true in 1995 it was true in 1998 in 2025 it's absolutely trivial to make a website it's absolutely trivial to make a scalable database you're going to sell or whatever and do it in afternoon so if you're in the early days these technology cycles often startups and incumbents will be selling the vision of what that new platform is and it works and that's the value proposition if

“look at something like log code which is kind of saddened between being the foundation model and the actual application itself I guess where you said you have an interesting purview of both you have a board seat with open AI and then you also have a company is there any way that you you think about that and like where companies can exist as applied AI systems on top of foundation models versus where foundation models are going to capture value I'll give sort of one framework that I think about the technology evolution which is in the early days of a new technology whether it's the smartphone or the web browser in the early days of the technology adoption cycle a lot of the value and as making it just work like it's it's hard to make a website or a database that scales to consumer scale on a website that was true in 1995 it was true in 1998 in 2025 it's absolutely trivial to make a website it's absolutely trivial to make a scalable database you're going to sell or whatever and do it in afternoon so if you're in the early days these technology cycles often startups and incumbents will be selling the vision of what that new platform is and it works and that's the value proposition if”
Speaker
Not verified from transcript
Publisher
The Logan Bartlett Show

06 / evaluation

It's interesting. It's an interesting point and maybe I need to reframe how I ask the question because I think you might be right that the totality of the value created on top of the platform itself dwarfs that.

“It's interesting. It's an interesting point and maybe I need to reframe how I ask the question because I think you might be right that the totality of the value created on top of the platform itself dwarfs that.”
Speaker
Not verified from transcript
Publisher
The Logan Bartlett Show

07 / belief

I think part of the reason that there's price compression for tools like Zoom or Slack and Teams is in part because the value you get from a sort of horizontal productivity tool is very hard to measure.

“I think part of the reason that there's price compression for tools like Zoom or Slack and Teams is in part because the value you get from a sort of horizontal productivity tool is very hard to measure.”
Speaker
Not verified from transcript
Publisher
The Logan Bartlett Show

08 / belief

The thing I think will happen, which is a mix of competition and technology adoption is a lot of AI agents now are being compared to their human counterparts, whether it's labor costs or effectiveness, in a market like software engineering or customer service in area that you know, perhaps like you know, conventional wisdom as AI agents will come to be dominant parts of this industry.

“The thing I think will happen, which is a mix of competition and technology adoption is a lot of AI agents now are being compared to their human counterparts, whether it's labor costs or effectiveness, in a market like software engineering or customer service in area that you know, perhaps like you know, conventional wisdom as AI agents will come to be dominant parts of this industry.”
Speaker
Not verified from transcript
Publisher
The Logan Bartlett Show
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