MasterStroke with Monica Enand & Sejal Pietrzak

AI, Macro Trends, Innovation and Ethics

• Season 1 • Episode 6

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“There is no such thing as timing the market…no one can time the market”

In this episode of MasterStroke, hosts Monica Enand and Sejal Pietrzak discuss the unpredictability of market timing, trend creation and positioning oneself to capitalize on both. They explore the benefits of first mover advantage versus showing up later to the party.

This conversation highlights AI’s disruptive potential in the legal field,  coupled with the growing need to preserve  the human touch.

Monica and Sejal focus on AI transparency, and explainability, emphasizing  the importance of collaboration  between technologists and regulators to fully understand the impact of AI’s rapid development and disruption across society and business.

They conclude by sharing their optimism for the next generation to examinethe role of technology and the ethical application of AI.










Georgianna Moreland - Creator, Executive Producer & Managing Editor;
Matt Stoker - Editor


Monica Enand:

How do you know if it's right for your business to react to trends? What?

Sejal Pietrzak :

if you could actually create the trend. Welcome to the Masterstroke podcast with Monica Enand and Sejal Pietrzak Conversations with Founders, CEOs and visionary leaders in technology and beyond.

Monica Enand:

AI is a trend, right, and it's one of many trends, right. Software as a service was a trend. Blockchain was a trend. There are technology trends. There are economic trends. This is kind of fusing that macroeconomic one, the economy. It's like before growth was valued in startup company, in software companies, growth was valued in any company, but now profitability is valued because interest rates are high. Right, that's another trend.

Monica Enand:

These are all macro trends and the question as an executive is you get all kinds of macro trends. I mean, some of them are stupid and then some of them are brilliant, like software as a service, and you ignore at your own peril, like you cannot be a camel and stick your head in the sand, or I don't know what animal sticks their head in their sand. Camel and stick your head in the sand, or I don't know what animal sticks their head in their sand. But anyway, the point is like every executive has to monitor trends and how do you know if it's right for your business to react to trends? So, for instance, people say to me all the time oh my gosh, you timed the market really well. Being an entrepreneur, it's so good that you timed the market. And I just laugh. I'm like nobody times the market. Anybody who tells you they timed the market, they're lying.

Monica Enand:

Instead of thinking about timing the market, what you really have to do is look at macro trends, see their validity, their applicability to your business, and then you position your surfboard. If a wave is coming, you can position your surfboard so that when the wave hits, you ride the heck out of that wave. But a lot of it is just like surfing you paddle out there and then you wait for the wave and you paddle, and you paddle and you paddle until the wave hits right, so it's not so much. And then in retrospect, after the wave hits, everyone goes, oh my God, you timed the market perfectly. Look at your surfboard on that wave. It's like, yeah, well, I also swam out there six times. A wave didn't hit. I also swam out there and paddled and waded and I want to focus on AI.

Monica Enand:

I think we can focus on AI and say like okay, how do we know the? What are the indicators to you, Sejal, that AI is a real trend and that maybe your businesses should be doing something about it? And why? Now, Like people have talked about AI for 20 years? I mean longer than that, probably, but I've been sort of hearing about AI for 25, 30 years. Why now?

Sejal Pietrzak :

You know one thing I want to say is go. So go back to your surfing analogy and and trying to figure out what is a trend, or can you catch the trend? What if you could actually create the trend, Absolutely?

Monica Enand:

I think AI sure, chat, gpt-4 did things and was usable in a way that was really accessible to people, but had they not done that, someone else would have. I mean, the technology was ripe. It's like the genie is going to get out of the bottle and once the genie gets out of the bottle, nobody can control or put the genie back. Right, like there are all these, like Google, there are all these different open AI competitors right, that are launching similar things and have different advantages, but the technology was ready to happen. Now, why was it ready to happen? Is it because of Moore's Law? Is it because computing power is finally there? Is it because bandwidth, because there's enough pipes to shuttle enough data? Is it because we're all using mobile devices and we're creating so much data? Is it because, you know, I mean there were a number of things that you could say didn't exist 20 years ago. There didn't exist the computing power, there didn't exist the broadband pipes, 5g, mobile devices, the proliferation of mobile devices and the quantity of data that we're all generating, right to do these training models. Those things didn't exist 20 years ago, but now they do, and so it was going to happen. Like it was going to happen, no matter who was going to do it.

Monica Enand:

Now is somebody first. Is it best? I mean, the other question is is it best to be first? I don't know. You know, I think Yahoo was probably first to the internet browser. Or, you know, mosaic was the first internet browser, but then Google. You know, when it comes to search, google ate everybody's lunch. I don't know if it's best to be first.

Sejal Pietrzak :

You know it's interesting. So, going back to creating the trend, yeah, I mean, sometimes being first isn't the right thing in 1995. So I mean, I guess we're dating ourselves. I got a cell phone back then and I thought this is great to have, because now I'll be able to reach people and connect. And it wasn't the flip phone yet, it was just a regular kind of phone, I don't even know how to describe it. But you know what happened after three, four, five months of having it, I realized I never used it because nobody else had a phone. So the trend and anything, you think, well, of course, why not? But you know, the whole point is being able to, you know, connect with people, mainly for, hey, I'm meeting you at this restaurant, where are you, you know? But then if they don't have a phone, are you going to call them at home and leave a voice message? You know they're already on their way. And it became something where, if you didn't have the other half, uh, it didn't work. So, um, you know, for me I got rid of the phone. And then I started realizing maybe it was around 2000 when I actually got my phone and that's when everybody was using it, but that was five years later. What a big difference from the time that it was first out there and consumers get it. And I think I paid $45 a month in my first one and back then in 1995, $45 was a lot but I thought it was worth it. But it wasn't because you were too early on in the trend.

Sejal Pietrzak :

And I think that's the same thing with AI. I think it's been around. You asked what you know. It's been around for 20, 30 years and it has, and companies have used it and people don't even realize what is AI versus not.

Sejal Pietrzak :

You know, when you use as a consumer, you go on um a website and you chat, you know, with someone. You know I think people automatically thought, oh, I'm chatting with a person, but then you realize no, it's actually a chatbot and they're utilizing all the data that the chatbot is using, all the data that it has to be able to respond, and it's not chatting. You know it's not speaking. Back then it was just, you know, writing back and forth in sort of a chat box, this chat bot, and that was all AI. But it wasn't as good as it is today and it's going to keep getting better and better. And so you know there's trends that are out there, that have been there for a while but now are getting even better. And then you start realizing you're right. No one can time the wave because no one knows when it's really going to hit or when the new technologies are going to really make an impact. But I guess you keep staying out on that surfboard waiting and then making it happen when you know when it does.

Monica Enand:

Yeah, one of the big trends that that our company took advantage of was the kind of consumerization of software and that, you know, once iPhones and apps were proliferating, we as humans all got better at using software and their user interfaces got easier and sort of more consumer friendly. And at the time that we started Zapproved and launched our first product we were going to market at a time where business software was bleh. I mean, it was gross. Like you could walk around a trade show and look at business software and it was all these grids. It was basically the databases exported to the viewer right, and it was basically the databases exported to the viewer right as opposed to thinking about how a user might go through a task. It was sort of the engineers exporting their understanding of the data and the data relationships to the user interface.

Monica Enand:

And we said, hey, like the consumerization of software is going to be important for usability, kind of the consumerization of the user interface of software. And so we said, okay, what is the task that a user is trying to accomplish? And let's make our user interface look that way. Let's use a bunch of stuff that people are familiar from using apps and we'll do enterprise software, but beautiful and easy to use enterprise software and in the beginning that was the competitive advantage we had you know, the number one when we did.

Monica Enand:

You know, one of our best practices in product management was to do these win-loss calls and kind of, when we were in a competitive deal, we would go back and say, all right, why did you choose us? Why did you not choose us? Why did you choose our competition? The number one reason we heard where we won we won on usability and that was definitely the beginning of a trend and, of course, everybody caught up. But it really helped to be there first because that was a trend that kind of we knew was going to stay, because the way that mobile apps were proliferating and consumers were using apps.

Monica Enand:

You know, sometimes I think it does pay to be first and first mover advantage really allows you to build kind of a moat or an audience. But sometimes it's not. And it's not bad to be second or third. When I say there is first mover advantage, there is, but that doesn't mean that the second or third or being later to a trend is inherently a disadvantage. It actually has advantages. And then the question is are there lower risks to be second or third or later in a trend? Do you think about that with your companies when you think about this trend of AI?

Sejal Pietrzak :

Yeah, I mean, there's no way to be first because it's been out there for so long already, but what I find is that with AI, there's multiple different ways that you can utilize AI in your companies.

Sejal Pietrzak :

You can be thinking about AI and people often think about AI as oh, how am I going to put AI into my products and what am I going to do to be able to create those products that are even more and you talk about usability but make them even more valuable to the customer?

Sejal Pietrzak :

There's also a whole aspect of AI, which is an internal AI within the company, and ways to be able to make the company more efficient, to do more with less by utilizing AI in your operations, and more and more and you talked about profitability at the beginning of our conversation. It's so important to be able to think about how do you do more with less when having that level of profitability and understanding that having money for a rainy day, having money to be able to go do more acquisitions, having money so that it's just like a savings day, having money to be able to go do more acquisitions, having money so that it's just like a savings account, right, the way we all have money in our own personal lives that we save. You know companies need to do the same thing. There's ways to do more with less spend, be more efficient, be more operationally excellent by utilizing AI, and I think that is a new trend. It's not new, but that is a trend that a lot of companies are starting to embrace.

Monica Enand:

Well, and I would add, I would go even farther. I agree with you and I would go even farther. I was recently at an event and I was chatting with the CMO of a software company and he was saying that, oh, they aren't going to, they're going to resist using AI because he believed the personal touch of sort of demand gen emails and drip you know the drip emails you know it was really important. I couldn't help but listen to him and think, wow, you're putting your company at a huge disadvantage. Help, but listen to him and think, wow, you're putting your company at a huge disadvantage Because if you are not using AI to help write the content that you need to write to generate for a demand generation engine for, you know, generating demand in the marketing engine I think it is super inefficient. Other people are going to and they're going to have. Their customer acquisition cost is going to go way down compared to yours. Their investment dollars are going to stretch farther and I don't think I don't think that's a winning strategy Like it can't possibly be.

Monica Enand:

When people come to me and want to work for me or my company, I do appreciate it when they tell me hey, I watched this interview of yours, or I read this article of yours and I saw how you talked about this and like I appreciate the work and the effort that they put into. It tells me that they are a diligent person. It tells me that they really have done the work to figure out who I am, who our company is. It tells me that you know they're, they're serious about what they do. So like does any of that sort of diminish in the in the sort of like I threw everything in chat, gpt, I don't know? Part of me feels a little bit like it does.

Sejal Pietrzak :

Here's the thing If you put it all into chat GPT without actually reading it yourself or watching the videos and the interviews of the CEO yourself or reading the press releases, then it's going to come out during the interview that you didn't actually know any of that stuff and it's going to come out at some point where you're going to look at it and say that will hurt you at the end of the day and if you are truly interested in the company, you're going to want to do that. You don't do it because you're going to go into an interview. You don't do it because you are trying to get the job or get the interview. You read all of that information because it truly interests you and, frankly, if that company and what that CEO and the company's press releases and the company's values and all of that isn't of interest to you enough to spend the time to read it, then you shouldn't apply to that company If it doesn't resonate with you enough that you like were caught up in it.

Sejal Pietrzak :

To watch it, yeah, to watch the videos, to watch the interviews, whatever it is, as you're doing the research, then then then, of course, you don't want to apply to that company, because that means it doesn't matter enough to you. So I think it can be used as a tool. It's not to replace what you might otherwise do in terms of talking to people, but I think AI can and should be used as a tool in the right way, in the right context. Why not? I mean, we use the internet when we search on whatever search engine you use, google or otherwise, to be able to gather information quickly. Is that back then, when that first came out, instead of using Encyclopedia Britannica or going to the library now, we went to Google search? Is that cheating? No, no.

Monica Enand:

I agree with you. It was I agree with you. It just takes us a while to get used to new technologies and new trends. I agree as humans.

Sejal Pietrzak :

Just because it makes it all easier.

Monica Enand:

So do you ever think about with your companies? I mean one thing when I get presented with a new trend and AI is definitely one, though, that I had been thinking about a lot, because our company worked in the legal profession and in legal, I am confident that AI is going to be incredibly it's already starting to be and is going to, over the next 10 years, be incredibly disruptive to the profession of law, to attorneys, in so many different ways. But do you ever think sometimes that, and when you're advising your companies and your executives, do you ever think about there's an adage that people who have a hammer are going and looking for a nail. Do you ever fear that? Sometimes people will say, oh, I have AI, so I should find everywhere that I can use it, and that they use it in places that it shouldn't.

Sejal Pietrzak :

Give me an example.

Monica Enand:

You know, I think there are some applications where you could spend a whole lot of time trying to figure out AI and it not necessarily be the right technology, or do you think it's just going to disrupt everything? I mean, it's possible that it disrupts everything, but there are certain things that are truly interact, like the personal touch right and humans where it matters right, it absolutely matters, meaning the human touch absolutely matters.

Sejal Pietrzak :

Now, you know, with not wanting to a lot of companies, being remote first, not wanting to go back into the offices, I think it's a challenge to be able. You miss out on that human touch, you miss out on that ability to connect with people. I mean.

Monica Enand:

I think Gen Z has anxiety rates much higher than the older generations and I think all the Zoom and remote work is contributing to it because they don't feel as connected to it. Because they don't feel as connected. So, okay, you asked me for an example of a profession. But therapists, what are HR? I mean even the hiring in the headhunters or recruiters, even in the hiring process. Now they might use AI to help narrow down candidates or to look at a lot, review a lot of resumes or whatever.

Sejal Pietrzak :

But in the final. I've heard of this.

Monica Enand:

Yeah, a lot of companies do that, do you? Don't? You think that HR is an area where AI is not going to take over their jobs? It's not.

Sejal Pietrzak :

I mean, I don't there's no way to be able to really get to know someone there's.

Sejal Pietrzak :

I mean, it goes back to that human touch, that human element, and that's why, even when I interview people, I always like to meet them in person.

Sejal Pietrzak :

You know, I mean now a lot of interviews are done by zoom, but I think there's this element of you're working with an individual, a person, and it's so important to connect face to face, shake hands, sit across the table from each other. You know, there's something that I call the airplane test, whenever I'm interviewing someone, which is could I sit on a plane next to this person in a middle seat for six hours across the country? Is that someone that I would want to do that with, and do they pass that airplane test or not? And you can't do that with AI, you can't do that remotely. You got to not to say that you have to sit, you know, on a plane with the person for six hours, but at least sitting down with them and meeting them and thinking about, you know, if there was no movie to watch and nothing to do outside of you know, sitting and talking to the person. Let's pretend that was the case.

Monica Enand:

Could you do it, and there's something about their EQ and their ability to read people and that you that you can only get by sitting down with people. But you know, there are people, obviously people who are brilliant at certain things. You need them to do. I had brilliant engineers that I would not want to sit but developed amazing technology, but I would not want to sit with them on an airplane. But it depends on what you're hiring them. You know the job for.

Sejal Pietrzak :

Oh, that's a good point.

Monica Enand:

That's a great point. Yes, no-transcript. And that some impartial, fair person presides over that and makes rulings and decisions. I don't know. Would we ever trust that? Do you think to an AI? I don't know. I don't know. Would we ever trust that do?

Sejal Pietrzak :

you think to an AI? No, I don't think so, but I don't think anybody's saying AI should take over everything. Ai I think of as a tool, just like anything else that we utilize as a tool, like Google Search as a tool, various different apps that we have on our phone they're all tools. You know various different apps that we have on our phone. They're all tools, but they don't fully replace what you do on a human level.

Monica Enand:

I agree and I think what I'm trying to get at is as an executive, as a person who's in the working world and has to navigate where does AI make sense and where doesn't it make sense?

Sejal Pietrzak :

Well, Monica, what do you think in terms of? Are there professions or areas where AI actually could not work?

Monica Enand:

or maybe even hurt. We're hearing a lot about AI safety and people afraid of AI right and trying to slow it down. Now, while I don't think you can put the genie back in the bottle, I think those safety concerns are warranted and we should be careful and intentional about where we use this technology. You know, in the. You know I worked with a lot of lawyers and judges in my profession because you know my software was for the legal industry. You know, a lot of those judges were really scared about what AI, while it couldn't replace them, they were scared about what AI was going to do in terms of impacting how they do their jobs. One example was there were there's a push to use in bail awards. They recidivism, or the likelihood to commit another crime, is one of the factors in whether they decide to award bail. Well, a lot of that prediction algorithms are based on training data.

Sejal Pietrzak :

Yeah, because AI is taking input data to then be able to come up with the answer.

Monica Enand:

I mean, that's what it's taking massive amounts of data and all of so those, so those algorithms are trained on the, the data that we have. And if you look at the data we have about committing crimes, we know that our justice system is incredibly racist, right, it has historically been incredibly racist. We know that, for instance, marijuana use, when there were a lot of people in jail or still are, I guess for marijuana use, even though marijuana use was about the same in white and black communities, there were eight times as many black and brown people in jail for marijuana use than there were white people. Why? Because we convict more black and brown people, and we know this in all aspects of our criminal justice system, right. And so now you feed that data. So now you say, okay, all of that historical, massive amounts of data that we have about convictions and we feed it in, we say, okay, predict who's going.

Monica Enand:

That's going to be incredibly racist. If the data was racist and the history was racist, then the AI is going to be incredibly racist. If the data was racist and the history was racist, then the AI is going to be incredibly racist, right, and have all its bias and discrimination. It's not just race, it's gender, it's you know all the different ways in which there is bias and discrimination in our lives. It's just going to exacerbate it as opposed to fixing it, if we take all the training data, and you know that's.

Sejal Pietrzak :

I mean that's got to be.

Monica Enand:

It's a good question. You know there are lots of smarter people than me thinking hard about what to do, but I do think one important area is, you know, transparency. A lot of these models and these AI, I mean okay, they're all just black boxes If you think about. I mean okay, they're all just black boxes If you think about Facebook or social media. A lot of the dangers that arose in social media was because we were getting shown content or decisions were being made about what we would see and, honestly, the algorithm designers themselves don't know why the algorithm is choosing to show you whatever it's showing you versus what it shows me. They don't know because the AI is a black box. They're feeding in data that things are coming out, decisions are coming out, but they don't know right. So I think it's really important and I know there's a growing area of explainability in AI where people are trying to put in transparency and like why do algorithms make decisions that they do, for instance, being approved for a loan?

Monica Enand:

You know banks are going to approve credit worthy, you know loans for people who they deem credit worthy, right, if they know what about that person, what characteristic about that person is why the AI made that decision. They can eliminate, they can go. Then a human can go back and go. Okay, this was an aid. Like you said, it's a tool, but it requires a human to actually go through. Because we have ethics in a society, like we have ethical things that we want our society to be, and if we, if we allow it, if we don't have that human making those ethical judgments, I don't think that we can let kind of AI run amok and be overused. I don't think we'll have the society and the outcomes that we really want as a race.

Sejal Pietrzak :

Absolutely, absolutely, I mean. That's why, you know, I really believe it. It's one aspect, or a tool, or an efficiency measure or a benefit to be able to give us a different way to think about something, but it is not the answer that can result in, you know, decisions being made without that human intervention, without that human touch. There's probably a lot of different ways that you know this. Ai safety, as you called it, and this notion of doing AI for good, has to be a part of everything every executive is looking at, as it's becoming part of the way technology is put in place, the way decisions are being made and utilizing it. What do you think we should be doing more of as executives and as leaders of companies?

Monica Enand:

I have to say that I'm feeling with AI. I am feeling that technologists are doing a better job than we ever have in the past. You know of asking these questions and thinking about it and, in fact, involving regulators and saying like, hey, this needs to be regulated, and sounding the alarm bells. Right, if you think about the social media era, it was move fast and break things and let's just go and do these things, and there were so many unintended consequences that I don't think and usually technologists I mean, I'm a technologist, I love technology, I love the advancement of technology and I want to see it happen.

Monica Enand:

And technologists are usually the ones that are kind of running headlong into something, wanting to have it happen as fast as possible, without thinking about all the potential unintended consequences. And I think in this one, actually this is the first time I've seen where people are actually starting to say, hey, should we be real? People who understand the technology are saying should we be slowing down? Should we be thinking about this? Should government get involved in regulating? How can this go wrong? Right? So the fact that we're actually asking those questions and having those conversations, that's, you know, that's the biggest part of it, right?

Sejal Pietrzak :

No, I think that's really important important.

Monica Enand:

I am super hopeful about the next generation because I think this generation that we see coming up through the ranks are just entering their careers more so than ever and maybe because they've lived with this climate emergency but more so than ever are asking questions like what do we want this world to be and how do we use our talents to make it the world that we want it to be, as opposed to the world that it always has been? Whereas, honestly, when I was 22 and graduating college and getting my first job, I don't think I asked those questions. I don't remember asking those questions. I remember thinking what is the best job I can get, what is the most interesting job with the best work environment, but I don't think I was asking those kind of hard questions about hey, where could this technology take us? How is it going to shape the world? What do I want the world to be like? You know, I have to say I'm very, very hopeful about the next decade and to get to that point even further.

Sejal Pietrzak :

I think these young driven folks coming out of college in their twenties right now and are asking those questions really do believe that they will and have the ability to make a difference in the future outcomes of where we are. And and it is true, because when you believe it you can make- it happen.

Monica Enand:

There is something contagious about the hope and the belief that you can do something to impact the world, and I I think that's the best thing you can spread.

Sejal Pietrzak :

That's really great. Well, this has been a really exciting topic around everything from macro trends and, and uh AI to having that exciting belief in where the next generation is taking us, and and and. We're excited to continue talking about all of these things and more uh on our podcast.

Monica Enand:

I could definitely sit on a plane with you, say, jill, for six hours. I don't think we would need a movie at all.

Sejal Pietrzak :

I know it's so true. We could literally talk for hours and hours and, and, uh, and uh, yeah, well, thank you, monica, and thank you to Georgiana Moreland, our executive producer. And this is Sejal, looking forward to talking to you next time. Thank you for joining us. Please follow and subscribe wherever you get your podcast. We would love to hear from you on our LinkedIn page at Masterstroke Podcast with Monica Enid and Sejal Pietrzak.