Why Your Next Executive Assistant Will Be an AI — Deon Nicholas (Espa.ai)

7 May 2026 · 41 min · 19 chapters

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Deon Nicholas explains agentic AI’s shift from answering questions to taking actions, then applies that idea to his new consumer product, ESPA—an AI executive assistant that schedules, drafts and sends emails, and proactively handles tasks using learned personal context while emphasizing privacy.

Guest backgrounds

Deon Nicholas is a pioneer in agentic AI. His first company, Forethought, used AI for customer support and was acquired by Zendesk. He previously worked at Meta (Facebook), Palantir, and Dropbox; he studied AI/NLP at the University of Waterloo and grew up in inner-city Toronto.

Key claims

Action + context drive much higher resolution rates (70–80% vs 20–30% industry). Founders must “reinvent” as model tech changes. ESPA learns patterns (tone, scheduling habits) and lets users audit/edit “memories” for privacy.

Notable examples

ESPA rescheduled meetings after he tore his Achilles; reminded him about medication; found 1099s/receipts during tax season; voice-requested an introduction email; texts users only for high-stakes decisions.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

AI in Customer Service: The Future

0:00 to 1:00

Learn how AI can revolutionize customer service by solving problems effectively.

“If you phone in your customer service and you're like, can you tell me about a refund for my package?”

Formative Experiences of a Tech Entrepreneur

1:37 to 4:20

Explore Deon Nicholas's childhood influences and early interests in technology.

“Well, sometimes I see you in front of the mic and you're singing.”

Founding Forethought: The AI Journey

4:21 to 7:11

Discover how Deon founded Forethought and the importance of customer-centric AI.

“And then let's leap ahead to your first startup, which we were proud to back.”

Evolving with AI: Lessons from Forethought

7:12 to 8:52

Learn about the rapid evolution of AI technology and its implications for startups.

“And yeah, really the vision was always take cutting edge AI and transform how the customer experience happens in businesses and consumers.”

Navigating the AI Landscape: Insights for Founders

8:53 to 12:11

Gain insights on how to innovate effectively within the evolving AI landscape.

“So we were always reading papers trying to stay on the cutting edge.”

Reflecting on Leadership and Company Culture

12:12 to 14:01

Deon shares his reflections on leadership, company culture, and personal growth.

“And before we get into that idea maze, what do you want to do the same in this second company?”

Building a Company Culture

14:01 to 15:46

Learn how a CEO's strengths and weaknesses shape company culture.

“And being extremely in tune with what those are is actually what is in the end going to be how you build a great company around yourself.”

Introducing ESPA: The AI Executive Assistant

15:47 to 18:16

Discover the vision behind ESPA and its potential to transform the way we manage tasks.

“And so can you tell a little bit about the next brainchild that struck you?”

ESPA's Functional Advantages

18:17 to 21:21

Explore how ESPA can automate tasks and learn user preferences for better support.

“You want the thing done, and everyone's feeling overwhelmed.”

Balancing Personalization and Privacy

21:22 to 22:55

Understand the challenges of maintaining user privacy while delivering personalized AI experiences.

“But in short, like nobody wants their data being sucked up and used by, you know, open AI or whatever.”
Show all 19 chapters

Real-world Applications of ESPA

22:56 to 24:16

Hear about practical uses of ESPA, including a demo of its capabilities in action.

“Well, and I saw an actual demo the other day.”

The Future of AI Executive Assistants

24:17 to 28:01

Gain insights on the evolving landscape of AI assistants and their role in everyday life.

“So obviously Apple wants to own the user, you know, Google and Gmail and G Suite and all the agentic frameworks.”

The Rise of AI Executive Assistants

28:01 to 28:53

Explore the growing importance and potential of AI executive assistants.

“And the model layer labs are going to start to kind of turn inward and be like, well, this is the next thing we have to either try to own or buy or build or whatever.”

Surprising Use Cases for AI Assistance

28:54 to 30:19

Learn about unique and practical applications of AI in everyday tasks.

“And so what are you learning about how they used it?”

The Personality of AI Assistants

30:20 to 31:34

Delve into the design of AI personalities and their relationships with users.

“So actually, that brings up an interesting question.”

Balancing Proactivity and User Comfort

31:35 to 33:04

Understand the nuances between proactive AI assistance and user annoyance.

“And so Aespa has a personality you can actually customize.”

Future of AI in Workflow Integration

33:05 to 35:06

Discuss the potential for AI to seamlessly integrate into personal workflows.

“And then you realize, no, people don't actually want that level of proactivity.”

Collaborative AI for Contextual Assistance

35:07 to 37:19

Examine how AI can facilitate collaboration and context sharing among users.

“And that seems like the TAM is humongous, right?”

Executing Tasks with AI: The Future

37:20 to 39:45

Learn about the capabilities of AI in executing various tasks and transactions.

“new paradigms for collaboration, calendaring, and context actually appear.”
Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00Deon Nicholas:If you phone in your customer service and you're like, can you tell me about a refund for my package? Most AI bots out there will be like, well, here's our refund policy. Good luck. They want their problem solved. They want an AI that can ask, OK, who are you? I know who you are. And I know our refund policy. And I'm going to decide on the spot, will you get the refund? And heck, I'm going to issue the PayPal or whatever that may be. Again, if you're running a business, you're a founder, you're a VC, whatever, you're out and about, you're doing things. And so for me, one of my favorite things to do with ESPA is literally that voice memo on the go.

0:29Deon Nicholas:I was playing basketball and I tore my Achilles heel. I kid you not, it like sucked. I had a bunch of meetings that whole week and I just asked Aespa to like reschedule everything, reach out to people, say I'm so sorry, whatever, right? Like in that moment, that was what I needed Aespa for. You know, like I had painkillers or whatever medication. I was like, I'm a forgetful guy. Aespa, can you just remind me like every like da-da-da when I need to take my doses? And it would text me.

1:01Anne Dwane:Hello, and welcome to the Village Global Podcast. I'm Anne Duane, and today we have a very special guest in Dion Nicholas. So Dion was a pioneer in agentic AI with his first company, Forethought, which put AI to work in customer support. And that company was recently acquired by Zendesk. Now, Dionne is starting fresh and applying really cutting-edge agentic AI to personal productivity with an executive AI assistant that's really innovative and super helpful. So, without further ado, let's talk to Dionne. Welcome, Dionne. It's so good to see you.

1:37Deon Nicholas:Thanks for having me.

1:39Anne Dwane:Okay. Well, sometimes I see you in front of the mic and you're singing. We'll get that done later. But today, let's talk a little bit about you. And before we dig in, what two or three stories shaped you? What made you the person and the founder you are today?

1:58Deon Nicholas:That's a good question. Off the dome, off the top of my head. So I would start with just like growing up, like my childhood, and just like randomly getting into computers and technology. So I grew up in inner city Toronto. My parents were immigrants from the Caribbean. We basically had no money. It was me, my three brothers. I have two older brothers, one younger brother. And, you know, but it was home. It was us, you know. And we would game a lot. We loved to play video games. And for me, I got, like, really fascinated when I was, like, really young with, like, what makes up a video game? Like, how do you even, like, how?

2:42Deon Nicholas:How do we have video games? How does a Game Boy work and all of that? And there was this one kid, my older brother's friend, he was like really into technology, really into computers. He was like the only one in our whole neighborhood. I think he was an actual hacker. Or like I told myself that, you know, as a little kid, I was like, oh, my gosh, like you can like get into people's computers and steal stuff. But he saw that I was like super interested in computers and technology and how video games worked. And he we had like I think it was a Windows 95 or Windows 98 computer back in the day. And he downloaded this little game maker on my computer called RBG Maker.

3:15Deon Nicholas:and that was like this this like aha moment for me because I started learning you can make the games like these stories that I would play with action figures or you know ideas I had with video games I learned how to like create them and it was drag and drop and you know over the years eventually I learned to code and because of that but I think that was like what set me on this path to eventually becoming a tech entrepreneur which is super cool one other random note on that is so my Twitter handle and everything is Dojideon. And many people are like, what the heck is that? Like, why is that your Twitter handle?

3:51Deon Nicholas:So the very first video game I ever made, obviously I was a kid, and I was really fascinated with Pokemon and Digimon. And so I made a game called Dojimon. And it was cute. It was very silly. But I was so proud of myself. And for me, that's kind of the symbol of, like, you know, where we began, you know, and why I decided to become a coder, technologist, and now an entrepreneur, investor. And so, yeah, that's what I keep with me.

4:20Anne Dwane:Okay, so those are formative experiences. And then let's leap ahead to your first startup, which we were proud to back. And tell us a little bit about what was the idea maze there, and then we'll get to how it evolved.

4:34Deon Nicholas:So continuing, I'll actually keep on the formative experience train because it's actually important. And so growing up in Canada, my family at some point in high school moved out to Edmonton, Alberta, which is like middle of nowhere. Like as far as most Americans are concerned. But in Canada, there are only a few AI labs. One is the Alberta Machine Intelligence Institute, which is based in Edmonton. It was affiliated with like the university there. And a lot of like early folks there are now at like Google DeepMind and things like that. So in high school, I like lucked into basically interning there.

5:09Deon Nicholas:And that was where I first learned of this concept called machine learning. But it was fascinating. It was all math and statistics and all of that. But there was like this inkling, the beginnings of like what could be possible, right? And so I got really fascinated with AI, machine learning. You know, there was a lot of concepts around reinforcement learning and supervised learning and all these things. After that, I started getting really interested particularly in natural language processing. AI that could understand language, answer questions, things like that. Being a student at the time, I was like, dude, can this be my AI personal tutor?

5:45Deon Nicholas:Like, whatever. Like, these are all the ideas that were kind of floating around. I guess, like, maybe precursor to being an entrepreneur, right? But, you know, fast forward many years. So I went to school out in University of Waterloo, studied AI, studied all the NLP courses. So by the time I moved to Silicon Valley and I was a software engineer, I'd worked at companies like Facebook, I guess we call it Meta now. Yeah, heard of it. Palantir, Dropbox. And in around 2018, actually 2017 really, I started to realize that a lot of the technology in natural language processing was starting to see the beginnings of like this exponential curve.

6:26Deon Nicholas:And so because I was fascinated with it, reading a lot of the papers, I was thinking about where can this apply to everyone, quite frankly. And working at big companies, I realized that what's more important than your technology is actually your customers. And that was kind of the lifeblood of any business, which was like to serve your customers and how you do that well. And the best businesses were the ones that did that well. And so I thought about AI being applied to customers and their questions. And it was this natural marriage really between the technology being like ripe, or I guess at that time I was probably underestimating how like big it was going to be.

7:00Deon Nicholas:But then also just thinking about this like user problem of what ended up becoming like customer service and customer support. And yeah, so started Forethought, which was my last company we launched in 2018. We were the TechCrunch Disrupt winners, which was super exciting, backed by Village Global. And yeah, really the vision was always take cutting edge AI and transform how the customer experience happens in businesses and consumers. And, you know, we scaled that to, I think, doing about a billion interactions every single month. And then just recently announced the acquisition by Zendesk.

7:32Anne Dwane:Congratulations. Thank you.

7:33Deon Nicholas:Yeah, which is super exciting. where I'm an advisor there now, and the team and the product continues to grow. So, yeah, really exciting journey from zero to where we are.

7:45Anne Dwane:Yeah. And tell me a little bit about you started, in a sense, pre-Transformer or pre-LLMs. Pre-LLMs. Right, and then the LLM thing happened. And so how is a good lesson for an entrepreneur how you navigate the tech changes that happen?

8:00Deon Nicholas:I think for me, I've been thinking about this idea as like the only constant is reinvention. And so we were fortunate enough to be able to kind of like see the future of what was coming with AI. And again, I actually think even underestimated. We were like selling this big vision of like, you know, NLP and AI and all these things are going to be really big. And people are like, oh, that's crazy. And then it's like even bigger than we were expecting, which is cool to say the least. But yeah, I think the average startup, if you're growing, it's a different company every six to nine months. And that was true before AI, and it's probably even more compressed now.

8:40Deon Nicholas:Like probably you try to, you know, every three to six months or so. And so in order to succeed, you as a founder, as a CEO, as leaders have to continue to grow, but also how you're doing things. Your product has to change and so on. So we always kind of embrace that at Forethought, this idea that we're constantly reinventing. So we were always reading papers trying to stay on the cutting edge. When we just launched, it was recurrent neural networks were the state of the art, but those didn't work well. So then there were long, short-term networks and then transformers and so on and so forth, right?

9:13Deon Nicholas:And so GPT-1 arrived in like 20, I want to say 2018, 2019, 2019 probably. And so we were aware of all these things. We were even using like when GPT-2 came and using some of these technologies. but it was so funny because when, by the time GPT-3 rolled around, we thought it was, oh, well, it was just going to be an advancement of GPT-2, which you can use to auto-complete a few sentences. So we actually almost missed when, you know, like when the like real AI came because we had been like, there's nothing, you know, nothing new here. But luckily we didn't. We kept innovating, kept thinking about it.

9:48Deon Nicholas:And really is like the idea is like keep throwing away your code. Like if there's something that is better than what you've got, keep reinventing it.

9:54Anne Dwane:Right, because you were able to surf on top of an improving, like, base frontier model environment. Correct. And do you have any advice for other application companies?

10:06Deon Nicholas:So one is, like, you have to move really quickly in staying on that wave, so to speak. And don't reinvent the wheel. Like part of the part of the game as an application layer company is to decide where you're going to innovate and where the underlying language models are going to just like take over. Right. And they're not perfect, you know, overlap. So there is a lot of white space, one versus the other. And so, you know, fundamental intelligence was the language models game. Right. Like they're going to get smarter and smarter and smarter. So then the question becomes, if you have Albert Einstein or the equivalent of like 10 Albert Einsteins, what would make that person really great or really bad at customer service was kind of how we thought about it, right?

10:55Deon Nicholas:And so you're going to get the raw intelligence, but you're going to need context. It turns out in our case, most of the distinction between good customer service AI and bad customer service AI was actually the ability to take action. you know hey if you phone in your customer service and you're like can you tell me about a refund for my package most AI bots out there will be like well here's our refund policy good luck right they'll give you an FAQ right whereas what that person really wants is they want their problem solved they want an AI that can ask okay who are you I know who you are I'm going to look up the order the problem the thing that you're doing I know everything about you and I know our refund policy, and I'm going to decide on the spot, will you get the refund?

11:37Deon Nicholas:And heck, I'm going to issue the PayPal or whatever that may be, right? And that's like, that became the distinction between 70, 80 % resolution rates, which we're seeing at Forethought, to like 20, 30%, which the average industry was seeing, right? And so when you can find those deep insights on where you're going to innovate, right, in our case, it was action, it was the ability to have self-learning AI and things like that, you start to draw separation. And so even though there are companies that are, you know, racing into a space because they think it's hot, they're actually racing to like that lowest common denominator problem and not what's going to drive 10x value.

12:10Anne Dwane:Amazing. Okay, so now you're thinking about your next company. And before we get into that idea maze, what do you want to do the same in this second company? And what do you want to do differently? Because it's a very successful, 4Thought's very successful, it's going on. But as you reflect back, what will you replicate? What will you change?

12:27Deon Nicholas:One thing I'm excited about, and I think we did a really good job of, was being really customer-centric and focused on product market fit at every step of the way. And again, that spirit of innovation, right? So that's something that, you know, in hindsight, I think we did pretty well, which was like being customer-obsessed, figuring out how we're going to drive ROI, how we're going to drive value, and not just be like a research lab. And there is a space for research labs. It's very hot right now. It's very hot, exactly. Like, I'm an app player guy. I just, I know, you know what I'm saying? But the, and the distinction there and the superpower, I think for us was in being able to say, we know how to be on the forefront.

13:06Deon Nicholas:You know, we were publishing papers or patents or like all of these things, um, building the best technical team. Um, but also at the same time, we know how to take that and just like focus on the end user. Um, and that's what really gave us this power and the ability to like build a great business in like a very competitive, um, space, right? Right. It's the that ability to focus on not just like what the models are doing, but literally what's going to solve the problem for the customer. So I think there's there's a lot of lessons to take away in scaling a company in that sense. Things I'm going to do differently.

13:36Deon Nicholas:I've learned a lot about myself as a leader and as a CEO and as a founder. You know, like just how you think about hiring decisions, how you think about running a company at scale, kind of like the operational leadership. For me, probably the best way I'd boil it down is that every CEO has their own superpowers, their strengths, and has their own blind spots or weaknesses. And being extremely in tune with what those are is actually what is in the end going to be how you build a great company around yourself. In many ways, every company is a reflection. Like the company culture is a reflection of both the strengths and weaknesses of any given CEO.

14:16Deon Nicholas:And I think there's beauty in that. Like you're making the choice. You can't have everything. And that's what kind of co-creates these different company cultures. And so I've learned to kind of embrace that. I think in my first company, I was almost like afraid of that. It was like this weird imposter syndrome, if you know what I mean. As just like a simple example of that, I come from a deeply technical background. when I first went to fundraise, a lot of investors were like, well, you're an engineer, your co-founder's an engineer, who's going to sell the product? Like, how are you going to sell?

14:51Deon Nicholas:And that, like, I weirdly internalized that a lot. And so for like the first, you know, few, probably a couple of years of forethought, I just assumed we had to hire other people who could sell, you know? And eventually I started realizing, well, I'm closing this deal, I'm closing that deal. and like my teammates and co-founders like bringing me into like, you know, pitch and and storytell and do all these things. And I didn't realize that like the ability to to connect with people, the ability to storytell, which means to sell, to fundraise, to recruit is like one of my superpowers, you know, and it's something like like I'm not kind of ashamed to say that.

15:29Deon Nicholas:Right. In a sense. And so that means that like I was probably building the company completely wrong for the first, you know, maybe three to four years, at least in that regard. Whereas, like, there will be other strengths, there will be other weaknesses, and knowing what those are and, like, embracing those will actually teach you where you need to hire, for example.

15:46Anne Dwane:Yeah. So you identified an idea that is not a B2B idea. And you're a B2B founder. And so can you tell a little bit about the next brainchild that struck you?

16:02Deon Nicholas:Yes, yes, yes. So I'm excited. We are launching ESPA, the AI executive assistant for everyone, effectively. And yeah, like when I think about this idea, one of the things that excites me is just that agentic AI, the ability for AI to actually move and act and, you know, so to speak, live and breathe in your world and the things that matter to you is actually still on in its infancy, so to speak, especially outside of Silicon Valley. Like we in Silicon Valley like to live like five years in the future. Everyone's got their open claw and their clawed code and they're on the terminal and they've got their MacBook Mini that they never close because it's running some, you know.

16:45Deon Nicholas:And then the moment you leave Silicon Valley, and there's nothing wrong with that, but the moment you leave Silicon Valley, you realize that everyone who is trying to achieve great things, right, whether it's a freelance designer or a realtor, a CPA, all of these people, their use case for AI today is basically using ChatGPT like a search engine, right? And so how then, if you're a small business owner running a company, how do you get help in terms of your emails, scheduling, all the tasks and to-dos that are being thrown your way, all of those things, right? And so Aespa is really the embodiment of solving that problem.

17:25Deon Nicholas:It's an AI assistant that plugs into all of your integrations, all of your worlds. So whether it's your Gmail, your Outlook, even your OpenTable for booking meetings or your Uber for booking rides, like all of the interfaces that you have every single day. And it is effectively your executive support. Right. So if you're scheduling meetings, you can text ESPA and just be like, hey, put this on the calendar, reach out to, you know, and schedule the podcast appointment. Right? Like all those things you can do and you can interact with us all through text, WhatsApp, and existing interfaces. And so I fundamentally believe this is going to be the kind of AI that, you know, billions of people are going to be able to have access to.

18:08Deon Nicholas:Kind of like, you know, everyone talks about like the Iron Man's Jarvis. Yes. And we don't yet have that in the world. And I think there, you know, it's time for something like that.

18:15Anne Dwane:It's, I mean, it seems like an amazing vision because nobody wants to build an app. You want the thing, right? You want the thing done, and everyone's feeling overwhelmed. So many emails, so many messages, so many texts. And you have a claim for your beta product that you can respond to emails three times faster. So what's actually going on in terms of helping prioritize all the messages?

18:40Deon Nicholas:Yes, yes, yes. This is fun. We can dig in. So I actually like to think about Aespa's core advantage in terms of three to four buckets. The first bucket is execution. Can ESPA actually take on tasks for you, do independent research proactively, and ultimately do something for you? So in this case around emails or scheduling, ESPA is actually able to automatically, as emails are coming in, figure out, is this an important email? Does it need a reply? Is it just an FYI? Is it spam? And for the ones that need a reply or even need an action, it can start to execute against that. Like, oh, okay, Ann is going to be free tomorrow at 3 p.m.

Read the full transcript

19:21Deon Nicholas:That is usually when she likes to tackle this kind of issue. Let's put something on her calendar, and then she'll be able to do that. So I suppose able to do something like that. For ones that require a simple reply, like, hey, can we meet tomorrow? You know, something like that. It's going to look up your calendar. It's going to draft a reply in your voice, and then it's going to send that email back to the person. So there's this ability to execute. And then the second piece is your context. Again, you can have all the intelligence in the world, but if you don't have context on the person, then you're kind of screwed.

19:50Deon Nicholas:And so when it comes to context, we think about that in terms of both personalization and integration. And so one of the secret sauces of Aespa is that Aespa really rapidly learns you from, for example, your emails and your patterns. Like, oh, Ann likes to go for a run at 5 p.m. Dion has kiddo time from 7 to 8 a.m. And little things like that, it's able to learn from your communications and from your scheduling so that when it's scheduling for you or when it needs to answer a question or do whatever, it just knows how to do that. It learns your tone of voice so that if you hate emdashes, I'm actually an emdash guy.

20:31Deon Nicholas:I'm not going to lie. I'm so mad that everyone's trying to get rid of the emdash. But if you hate emdashes, it will learn those nuances. is learn how to talk like you. You speak formal to your LPs, and you're pretty colloquial to your founders or your one-line chat. One of my friends was literally, she talks in shorthand, very Gen Z. Instead of saying for real, she'll just say FR when talking to her friends over email or whatever. And her ESPA has learned that. And so you can see that.

21:01Anne Dwane:Okay, so this is different than prompting because I see in the product there's some custom instructions, but you're saying way beyond that. It's observing patterns. It's observing patterns, exactly.

21:10Deon Nicholas:And then actually that actually ties into the last piece, which is privacy, which is actually in so many ways a pillar. So the fundamental question is how can you get personalization and privacy at the same time? And we're actually doing a ton of really fun, innovative stuff around how to do that. But in short, like nobody wants their data being sucked up and used by, you know, open AI or whatever. But at the same time, you do want the personalization. And so you can do that either through prompting, prompt engineering, or you can do that through models, right? And over time, we're actually going to do both.

21:43Deon Nicholas:But with models, if you're training a model on somebody's data, then you have to train that only for them, right? And so I think in the long term, there's going to be the resurrection of this idea of small language models rather than large language models that are monolithic, trained on everything. Imagine a small language model that can either run on your phone or run on a local machine or just run in a way that only you have access to it, but it is constantly learning you. So that's one way to think about personalization with privacy. Another way of doing that is through the creation of quote-unquote memories, right?

22:12Deon Nicholas:Like this idea of which eventually become context and documents or whatever back into the model. But it's human readable. It's human editable. So imagine if you can, and you can do this with Aespa today, you can literally audit and see everything it's learned about you in plain English. And if you don't like something, like, you know what? I do want to bring back the em dash. Well, then let's just go and, you know, let's just go and edit that, right? Oh, that's awesome. So imagine being able to do all these things in ways that the user can control, right? Like no training on your data in some monolithic model.

22:41Deon Nicholas:And anything that the model is learning about you, you get control of. And then there's a lot of technology and a lot of algorithmic prowess that you kind of have to build into the model in order to be able to do that at scale. So very, very excited about these kind of pillars, right, from execution to like the context layer, but then also through to privacy.

23:00Anne Dwane:Well, and I saw an actual demo the other day. We were at a meeting and you spoke into your phone and said, introduce this person to this person. And almost instantaneously, the email was sent out. And so it's like the self-completing to-do list. Exactly. That was amazing.

23:19Deon Nicholas:Which is super cool. Yeah. And so that's such a fun use case. And again, I believe in and as part of the context pillar, complete integration into your life. The average person doesn't actually want to interact with AI by sitting in front of a text box. Right. The average person, again, if you're running a business, you're a founder, you're a VC, whatever, you're out and about, you're doing things. And so for me, one of my favorite things to do with Espa is literally that voice memo on the go. You know, I'm at a dinner party or I'm driving even like you can just voice voice speak. so it's hands-free, all of these things.

23:50Deon Nicholas:Yeah, and that was a really cool case. I had met someone who was starting a fund, and he wanted an intro to an LP. And I was like, oh, you should meet my guy Robbie over here. And, yeah, and then I just voiced. I was like, hey, introduce Robbie to Satish, and boom, boom, boom. And it worked out, right? It just happened. It just happened. Yeah, yeah, it was amazing. And that goes, again, to that execution pillar. So that's how we think about that flywheel with something like Aespa.

24:16Anne Dwane:Got it. And let's zoom ahead to the future. What does it look like? So obviously Apple wants to own the user, you know, Google and Gmail and G Suite and all the agentic frameworks. So what do you think in a few years the world looks like of individuals with agents?

24:36Deon Nicholas:Yeah, what I'm finding is there's like this really interesting kind of white space in a sense, because all of the people you would expect to be building something like this have perverse incentives on some level. So what I mean by that is like take, you know, the open AIs and the anthropics of the world, right? They, on the one hand, they're very positioned to build like a great agentic product. But on the other hand, A, they are incentivized to be building better and better models. And how do you do that? By having people's data and doing that sort of thing. So the idea of privacy, like you can't have zero data retention from like these bigger models unless you're a company or an enterprise or something like that, which is why like we, you know, as Team Aespa have negotiated that so that we can give that benefit to our users.

25:24Deon Nicholas:Right. And so I think that there's a little bit of like misaligned incentives. And then I also think on this at the same time, focus is a little bit different. Right. Like you saw OpenAI completely cancel Sora. Right. Which would have been a great consumer product. but they're focused on their revenue bottom line, which is like finding probably more and more enterprise use cases around, you know, GPT or cloud or whatever it is there. On the other hand, you have like the open clause of the world and they're effectively just built for developers. Very powerful technology. I think really, really cool stuff.

25:56Deon Nicholas:But like the average person is not that. Like, again, it's Silicon Valley. It's us building for ourselves. And so when you actually look at it, like all the people who kind of have potentially an in here end up kind of creating their own form of lowest common denominator. And so when you think about the average person who has the need for an agentic AI assistant to actually be able to take action in their lives, it's going to be quite a while. You know, in the absence of like aespa, it's going to be quite a while before you're going to be able to get access to that. I think like it's really five, 10 years away in most cases.

26:30Deon Nicholas:So that's why we're really building this and we're trying to accelerate that timeline so that everyone, again, small business owners, freelancers, creators, like we actually have music producers using Aespa right now and swearing by it, right? And it's kind of crazy to see that, right? So I think in five to 10 years, we are going to see a convergence. I think the best way to describe it is very similar to the cursor model. You know, AI coding should not really have been a category. Like it was just like, you know, there was a GitHub co-pilot here and all these other things there. And like there was never, there should never have been a now$60 billion company built on coding agents.

27:08Deon Nicholas:Or there should never have been a cognition, right? Like in all those things, my portfolio company. But what happened was the great builders started to focus and go all in on creating a 10x better experience. And in some levels, the model layer labs followed. And they've been chasing. And I think Cloud Code is actually very, very good. But again, you still have cursor, which many people are like, well, there's no moat. Should they die? Like, what's going on here? But you realize that once you have the breakout capacity and differentiation, you can actually create a moat, right? And in their case, they're either going to build the model or go with SpaceX, right?

27:44Deon Nicholas:Yeah, right. And so I think that's just fascinating. And so right now, for the next two, three years, a lot of these companies are probably focusing all their energy in chasing this market. I think the AI, personal, exec assistant, whatever you want to describe it market is going to be a fast fall. It's going to be the next domino where you're going to have a few companies who are going to be able to create breakout amazing products. And the model layer labs are going to start to kind of turn inward and be like, well, this is the next thing we have to either try to own or buy or build or whatever.

28:15Deon Nicholas:And you're going to see a similar race and probably an even bigger one. Like we've learned that the cap on coding is pretty infinite, like the amount of things we can build. But I think like the cap on human work is also infinite in terms of the things we can achieve, the things everyone wants to do, especially in post-COVID era. You have people who are now you've got work, you've got life, you know, founders are doubling as investors. You've got, you know what I mean? Like people are our work, their parents, like all these things going on. And we're going to see more of that. Right. In terms of this life.

28:47Deon Nicholas:And so I think this need for like, you know, I think the Uber moment for an AI executive assistant is arriving.

28:52Anne Dwane:And you have some early users. And so what are you learning about how they used it? Anything surprising?

29:00Deon Nicholas:Yeah. So first of all, some fun use cases that people are using it for. Like, it was really cool. We saw like a spike during tax season. Yeah, it was like a bunch of people like, hey, can you find all the like 1099s in my email or find all charitable receipts from the last year? Because I'm like, I'm good, you know. So we saw a bunch of really cool stuff. So what's fun about these use cases is people know what they need when they need it. So for me, for example, a few months ago, I actually was playing basketball and I tore my Achilles heel. I kid you not. It sucked. I'm still more or less recovering.

29:41Deon Nicholas:But I remember and I was like, this really sucked. And so I had a bunch of meetings that whole week. And I just asked Aespa to reschedule everything, reach out to people, say I'm so sorry, whatever. right like in that moment that that was what i needed as before um and then i was like you know like i had painkillers or whatever medication i was like i'm a forgetful guy as but can you just remind me like every like when i need to take my doses um and it would text me you know as what would technically be like all right did you take it how much when blah blah blah all right i'll remember for next time little things like that um i don't even know these aren't even like you you know, regulatoryly combined use statements, whatever.

30:17Deon Nicholas:That's prescribing. Yeah, like it's not, but yeah.

30:20Anne Dwane:So actually, that brings up an interesting question. There's a fine line between an agentic assistant and a companion. Do you think about that ever? Like personality or, you know, people have...

30:34Deon Nicholas:Yeah, yeah, yeah.

30:35Anne Dwane:Get engaged with...

30:38Deon Nicholas:Your AI personal companion. Damn. No, we do, actually. Like, as in, you do have to think about what kind of personality and, like, what kind of relationship and what kind of, like, relation to the world you want your AI to have. Yeah. So even when we were launching and thinking about, like, our website and our brand and all of those things, like, is Aespa your AI assistant? Is Aespa your AI companion? Is Aespa your AI agent? Like, how do you— Confidant. Confidant, right.

31:11Anne Dwane:Like, I mean, he really does know a lot about you. And the best, like, chief of staff or executive support people actually are quite, I don't know, they can think ahead and they're prescient and they know you so well. It's a really interesting thing.

31:24Deon Nicholas:It is a really interesting thing. And so we've erred on, again, like when we think about our pillars, right, like execution, context, and privacy. Like we've really been grounded in those things. And so the first one being, like, the ability to execute. And so Aespa has a personality you can actually customize. It's actually one of the memories that, you know, as you're talking as you can kind of like configure. Again, you have full control over. But at the same time, like it's really focused on the people who are trying to achieve great things and trying to get stuff done. And so, yeah, we see it as like this kind of personal executive assistance.

31:57Deon Nicholas:Why we kind of use that phrase. But, yeah, when it comes to just like AI these days, like, I mean, it's a crazy world.

32:04Anne Dwane:Yeah. Yeah. Well, it is interesting. And like reflection had that pie. Do you remember pie? I remember pie. And it would sometimes a couple days later ask you a question about a conversation you had. Right. Like, oh, how'd that turn out? And it was just like kind of amazing. Yeah. I get care.

32:23Deon Nicholas:You care about me. Yeah. Yeah. One of the surprising things in terms of user behavior that we found was there's this balance between proactivity in your AI and annoyance. Yeah, or creepy. Or creepy. Yeah, like proactive or creepy. Which one is it? You know? And so that's been an interesting product learning, I would say. For example, one of the features we have is when you get an important email, ESPA can decide if it's important enough to literally text you about it. And in the early days, we got it wrong. Yeah, I got a lot of texts. You remember that. You're like, I remember the text. And it's like, we got that wrong.

33:04Deon Nicholas:And we're like, well, it's being proactive. And then you realize, no, people don't actually want that level of proactivity. Now, it's so funny. I got texts from some of our users being like, this is the coolest thing ever, because we've dialed in on that nuance. And so, for example, it only texts you if, A, it's a very big decision that an assistant shouldn't be making, and it's not sure, it doesn't have enough context for the answer. And those are rare enough and important enough that when you get that text, you're like, oh, this actually deserves my attention. Yeah, it's working well. And that shift was super cool to see when we just nailed that.

33:39Deon Nicholas:And so I think there's a lot of nuance like that when building any AI agent.

33:42Anne Dwane:And how do you think about your interface is a lot about, to me, voice, text, and it's abstracting a lot of the inbox away. Correct. Do you feel like that's the future?

33:56Deon Nicholas:That's a great question. So I'm a bit biased in this sense because I never really wanted to build a workflow tool. Like I don't want to build another inbox or anything else precisely because of what you're saying there. I think like at the end of the day, when you take like a step up in kind of the Maslow's hierarchy of needs here, people don't really care about having another tool. They care about the job that they're trying to get done. And so when you if you were to hire an executive assistant, you don't hire someone who also has an app that they're like, well, you can only talk to me through this app.

34:34Deon Nicholas:Like, it's not how this works. It's another teammate who you Slack with or you WhatsApp or you email. And I think that is the paradigm we want here at Aespa is that you are focused. You're in your workflows. You're in your inbox. You're doing things. But then by having an AI assistant supporting you on the executive side, you're going to spend less time in that inbox and thinking about the mechanics of it. And you're going to be spending more time thinking about the high-level function or the job you're trying to get done.

35:05Anne Dwane:Yeah. I mean, that is exciting. And that seems like the TAM is humongous, right? Exactly, yeah. And will ESPA work with other ESPAs?

35:15Deon Nicholas:Yes. In fact, that is available literally today. It was so cool. Another one of those things where when you crack it, you're like, this is sick. Like, I just, like, the future is here. Yeah, you can actually do this today, right now. So, you know, you can CC your assistant at ESPA.ai or your ESPA assistant on a thread. and it will schedule meetings for you. So like literally, if you're meeting with a founder, meeting with a VC, hey, adding my AI assistant, I think it's pretty, you should be clear, it's an AI. But it just works, right? And it can have a full-on conversation. It has all your contacts.

35:50Deon Nicholas:It knows when you don't want to meet, like all of these things and can schedule. And when we think about it, maybe this is like an interesting topic for a broader conversation around defensibility and moats. I actually think the idea of connected context is actually in so many ways the future. Because imagine now, anytime you and I ever want to meet, let's add aespa to our text thread. Or let's add aespa to our email thread. My aespa talks to your aespa. Instantaneously, we now have a meeting. So that's calendar, shared calendar. What about shared collaboration? If you and Ben have both met with a founder maybe separately and you're trying to write the memo on this, well your aespa has your context and ben's aespa has his context imagine just being like hey aespa like write the first draft of this memo and it's going to have all of the nuances of what you all think and so when it comes to context and collaboration or documents or getting stuff done like aespa will be able to do that um this is a very bad example because this is not something i should have my assistant help me with my wife keeps reminding me um is but like let's say i'm trying to shop for a gift for my wife and, you know, she's been using aespa and maybe she's been shopping and maybe aespa has connections to perplexity or other AI for, for search and shopping.

37:06Deon Nicholas:And she, you know, she gives my aespa permission to, to her aespa. I like, I know maybe her wish list or whatever. And aespa can help me figure out what that is. And so that's again, shared context. Right. And so I actually do think like when you really extrapolate to the future, new paradigms for collaboration, calendaring, and context actually appear.

37:30Anne Dwane:Yeah.

37:31Deon Nicholas:And in so many ways, that becomes a weird network effect in the AI age, which I would not have expected for an AI company.

37:36Anne Dwane:Yeah. And it's interesting to think about your agent can be controlling your privacy, but letting you get things done. Correct. Exactly. And like, I don't have to share my calendar with everybody if my agent can one-off work with other agents.

37:49Deon Nicholas:Exactly. And it's almost like you're giving out tokens or, you know, like app authorizations for somebody else's ESPA or some other, you know, token. Again, like a shopping app may just want your contacts and you can like one-off be like, yeah, ESPA, you're allowed to give that to that shopping app. And then it will be able to do something for you.

38:05Anne Dwane:And what is state of the art in execution today? Like credit card purchases? What's happening with and without authorization? Yeah.

38:13Deon Nicholas:I mean, I think all of that is possible, if not going to be possible over the next few months, quite frankly. So today, we started with your kind of productivity suite. So your emails, calendars were also plugged into your granola notes and all of your meeting notes and things like that. We're building out integrations every single day. We're backed by Zapier and folks like that. But yeah, like the other day, someone was like, well, can I use ESPA to book a lift? Right? Because, you know, imagine doing that. I'm like, I look it up. I'm like, the API is there. Like, why can you not? Right? And so I think all of these things, whether you're trying to book a reservation for a hotel, whether you're trying to book a lift, book airport travel.

38:57Deon Nicholas:Again, these are all like booking use cases. But again, you're trying to get work done. Whatever that may be, you can use ESPA. We're going to enable over time things like payments and credit cards and stuff like that. I think there's a whole fascinating discussion on what is the payment economy for agents? Yes. Is it crypto? Who knows, right? But like, you know, the ability to at least give a, imagine like literally just an AESPA. You give your AESPA a small credit card and permissions over certain things. All of that's going to be possible. Browser use is also the other thing. There's a lot of companies working on that.

39:30Deon Nicholas:And we're also integrating that into AESPA as well. So being able to log into your, like one of your portals. Again, like for me, for this Achilles thing, like, you know, having Aespa log in and be able to see when all my physio is, put that on my calendar. Today, it can do that not through login, but I just sent it my, like I had literally downloaded a PDF and I was like, figure this out for me. But imagine like it just being able to have all your context.

39:54Anne Dwane:It's amazing. Okay. So where can people find Aespa and what's the call to action for them to try it?

40:01Deon Nicholas:Yeah. So Aespa is really a tool for everyone, which is really cool. Like if you're listening to this podcast, then you're probably trying to achieve amazing things. You're probably a founder. You're trying to raise funding, trying to launch your company or what have you. Right. And so I think everyone who is trying to achieve more should be using Aespa. So head over to www.aespa.ai and, yeah, sign up. Start a free trial. And, yeah, excited to see what you achieve.

40:31Anne Dwane:Great. And would you like to sing the tagline of Aespa?

40:37Deon Nicholas:I will not be karaoke-ing on this podcast. Okay, got it. But you still owe me. I want to know. You were supposed to tell me what your go-to karaoke song is.

40:44Anne Dwane:Yeah, I got to get back to you on that. Where's Claude? We're out. We're out. Time to go. Okay, well, thank you so much.

40:52Deon Nicholas:I think this was a lot of fun. Thank you so much for having me. Thank you.

40:58Deon Nicholas:Hey, this is Ben Kaznoka, co-founder of Village Global. Thanks so much for tuning in to the Village Global podcast, where we go deep on all of the biggest topics in tech. If you enjoyed this conversation, please subscribe to our YouTube channel. You can check us out on Spotify, Apple, wherever you get your podcasts. We'd love to see you for the next one.

From the publisher

Deon is the co-founder and CEO of Espa Labs. His previous company, Forethought, was a TechCrunch Disrupt winner in 2018, scaled to roughly a billion customer interactions a month, and was recently acquired by Zendesk, where Deon now serves as advisor.

Village Global GP Anne Dwane sits down with Deon to talk about the launch and the journey that brought him here. They cover what he learned scaling Forethought through the GPT-1 to GPT-4 era, why the Iron Man Jarvis vision is finally within reach for everyone (not just Silicon Valley), the three pillars of Espa, why the model labs have perverse incentives that leave the door open for a new app-layer winner, the surprising network effect that emerges when one Espa starts talking to another, and where personal productivity AI is heading over the next five to ten years.

Thanks for listening — if you like what you hear, please review us on your favorite podcast platform.

Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.

Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

More from Village Global Podcast

All 44 episodes
Why Your Next Executive Assistant Will Be an AI — Deon Nicholas (Espa.ai)Village Global Podcast · 41 min
Listen in VO