You.com COO Alex Triplett | The True Role of a Chief of Staff (Podcast 597)

Every day you wake up, there will be a surprise. You don't know if it's good or bad. You just mentally prepare yourself. It's going to be bad. Something bad will happen today. You are responsible for dealing with it. And so then there's no emotion, right? You just like, you walk into it and it's like, ah, this thing happened. Okay, no worries. Let's figure it out. No problem. I try to box when I look at Slack. I try to box when I look at email and I try to chunk it. And there's like so much literature and research that shows you, you just degrade your ability to make great decisions. If you're looking at 2 or 3 or 4 different things at the same time, or if you superficially float by things and don't kind of dive in. People making decisions on Slack and Teams, like, you're not thinking it through.

Our guest today is Alex Triplet, who is the COO of You.com. It's a brand that you may not have heard of, but they are huge. All of the top tech companies are clients of theirs, and I've actually just added them to my watchlist on AngelList. I want to be an investor as soon as possible. Alex started his career in investment banking and private equity. He made the jump 12 years ago to the corporate side at the ION Group, where he co-ran the corporates division, leading 23 M&A deals and driving 20x revenue growth from $100 million to $3 billion while overseeing a team of 1,600 people. He then served as joint COO and CFO at Appfire. Now at You.com, Alex is, Alex is scaling the infrastructure that powers AI search and agents for companies like Alibaba and Volkswagen. He can speak to the benefits of applying an investor's lens to ops and why he believes in real-time business reviews over monthly financial reporting. He takes the same outcomes-based approach to AI adoption. He can share how he redesigned workflows around clear and measurable goals. He also speaks in layman's terms. You will understand everything he says. You'll have some huge takeaways on this. Grab a notepad. Listen, write down all the ideas you're gonna get from this and share this one. This is an episode that every entrepreneur, every leadership team member, and certainly every COO can learn from. We'll see you on the inside. All right, if you're an entrepreneur, you've gotta go check out the Genius Network. The Genius Network is for ambitious, giving entrepreneurs who wanna be part of the highest level connection group. And it's not just another mastermind. In fact, I have been a Genius Network member for 8 years. Genius Network helps build a better entrepreneur by focusing on health, wealth and making your business and life more ELF, which stands for easy, lucrative, and fun. Don't apply if you're just a taker, but do apply if you're a giving entrepreneur and you earn at least $1 million or more in revenue. And to see if you qualify, go check out geniusnetwork.com/apply. Again, that's geniusnetwork.com/apply. So Alex, welcome to the Second in Command Podcast.

Thank you, Cameron. Pleasure to be here.

Yeah, looking forward to this. Um, I was taking a look at what U.com is doing, and clearly you're not in a world that I'm orbiting in. I'm more in the entrepreneurial midsize company. You guys have got every— pretty much every single brand name that is in the tech sector as a client right now. You guys are, are really kind of crushing it. Can you tell us who U.com is and, you know, what your core products and services are, just so that our, our listeners understand.

Absolutely, Cameron. So at its most simple essence, we are Google Search for AI agents. So let me unpack what that means. You have this complete paradigm shift with the advent of AI. We know that software and what humans would do in a digital or non-digital way is getting replaced with agents all across the board. Whether it's an AI-native business in legal, like our customer Harvey, or whether it's a very large enterprise software business, like our customer Salesforce, now building and promoting Agentforce, another kind of tooling. Agents are how work gets done. Those agents rely on LLMs, or large language models, like OpenAI and Anthropic and Gemini and others to do core reasoning. But what they're all missing is that a model's training data only goes so far. It doesn't know what happened in the last couple of months. It has no idea what's going on in the Gulf region right now. It does not know that the Knicks just won in 5. Go Knicks. I'm a Knicks fan. So it doesn't know those things.

That was huge. I mean, are you kidding me? Game 4 was ridiculous.

Oh, man. Every— just the tightrope we walked, and every time we'd get down, and then we'd come back. Oh, so fulfilling. But the, the, the point of why we existed is LLMs are amazing and powerful, but they don't have that real-time context from the web. And these agents often need to supplement core reasoning from an LLM with what we call augmented intelligence or real-time intelligence from the web. And in the past, you and I would go to Google, we'd type in a prompt, and we'd get 10 blue links. And because we're humans, we read them very slowly. We don't go after page 1. Very rarely do we click on page 2., and we often click on the first 2 or 3 that are surfaced because of our personas and who we are and how we can get monetized by Google or other people. Yep. An agent doesn't need any of that stuff. An agent can read 100 responses like that. They can read full-page contents like that. They can discern that the response in number 32 of 100 was the right one.

Oof.

And so we are providing search results that could be up to 100 pages. Full-page contents. We have different endpoints that allow for an LLM to reason against the responses we provide. So we feed the web into an agent or into an LLM. We are Google for AI agents. That's what U.com is. And I think that people are starting to wake up to the fact that that search layer, that relevant real-time information layer, is so critical in making sure the accuracy of what happens with your LLM question being answered or with your agent taking an action. And it's becoming more and more prevalent, and I think we're in a good spot.

So this is— so enterprise is using your tools. Is the consumer using it? Like, are we using this instead of Grok or Perplexity or Claude or Gemini or like OpenAI? Like, or who's using the Google Search for AI agents?

Yeah, you could be using you.com with. So if you are a user of Anthropic, okay, the web search is a third party that's not Anthropic. If you are the user of Salesforce AgentForce, your web search is powered through U.com. If you are a user of, of Harvey and you're using the agent underneath the hood, they're using LLMs for a piece of it. And then the web search is powered by U.com. So holy shit, they're a really important pick and shovel. In the AI ecosystem. Because if you think about the stack, you've got the agent that you touch, you've got the LLM that you, you may touch or power the agent. If you keep going down, you've got this search layer, that's where we are. And then you keep going down, you've got chips, and you keep going down, you've got power. So we're one of that layer cake, information search layer.

So, so, so you're part of the system that we don't really see as the consumer, but without you, it's impossible to even get anything that we're getting. Correct. All right. So I don't know why you're not on my watch list on AngelList, but you will be now. Um, I'll have to go take a look and add you to that when I'm done. So in, in terms of working with enterprise, I know a lot of companies out there that are mid-sized organizations are trying to sell to enterprise, trying to sell to larger accounts. What have you learned in the whole go-to-market space of working with some of these bigger companies? I feel like, you know, back in the day when I was doing sales, I'm going to date myself going back 30 years ago, I felt like big corporate would always say yes to every presentation. And, you know, every one out of 50 might get to the finish line, but one out of 49 felt like I was just keeping them busy to validate their jobs to their boss. But there was never any intent. How do you sell to enterprise? How do you know when they're wasting your time? How do you get through kind of that clutter? Can you give us kind of a short course on that?

Would love to. Our motion is comprised really of two. So we think about it as a pincer. The bottom is what we call developer-led growth or DLG, which is akin to what software companies call PLG. We want to have users, typically engineers, that are builders. They may be inside of a large corporation. They may be you and me building on the weekend, you know, using Lovable or Replit or Genspark or something. And We have an easy-to-use API. You can pick it up and plug it into your application and you can start running calls through it and we give you $100 of credits for free. So that's 20,000 web search calls for free. And so we love to have developer-led growth, just adopt, which is really nice because that just builds up a good ecosystem of, of adopters. Typically though, with that motion, we're leading to what we call SLG or sales-led growth, which is selling to the enterprise that you talked about. And this is where a lot of people that I think start in Silicon Valley and frankly everywhere, it's a struggle for the reasons you mentioned, right? How do I get through procurement? How do we get to business decision maker? How do I run the classic medic or med tech or all those, those playbooks? And so we've come to find firstly, it's a very technical sale in what we're selling because we're selling an API that provides for web search, an API for those listening that may not be familiar. Application Programmable Interface. So think of it as a, a, an electrical cord that hooks one thing to another thing. That's basically what it is in simple terms. And typically the evaluator of this is an engineer. So the beauty of this is engineers, they are really judicious with their own time and they typically will evaluate us versus a benchmark. Hey, look, we have 100 questions. Your API can answer questions from the web. Can you answer them correctly and quickly?

That's it.

Benchmark us against some set of queries that you have. I love that because like an athlete, if you run fastest in this race or jump highest, you win. And so unlike when I used to sell enterprise software where there's art and craft to the demo and the pre-sales and this and that, and you're not sure where you stand, a lot of times in a technical sale, you know exactly where you stand. People will publish the benchmarks back and say, hey, look, you hit X% and someone else hit Y%, and that's why we're choosing you. So there's a portion of our SLG process that is, that is our sales-led growth process that is technical. But then what it comes down to is also we're driving a business outcome. And the thing that I keep preaching to the team that I think is inherent in every enterprise sales motion is, yes, you can cater to the engineer through a really good developer-led growth motion or through a good technical sale. But ultimately, whoever's writing that check or making the business decision, and they may well be a CTO, a CIO, a VP of search, a VP of engineering, whatever. They may be technical as well, but they want to know that you're driving some business outcome. So one of the things that we really focus on is our ability to go in and say, yes, we're selling you a technical product that does this thing that you need, but then here's why we help you drive value because of X, Y, Z. And that linkage to like the business outcome and driving value That's the important part. I once had a CRO that said, because you can. That was his sales pitch. And that was what he pitched to customers. I'll give you this thing or sell you this thing because then you can do something else. So at its essence, we try to marry that philosophy of finding the person or persons that really want to understand the business value that we're driving, make sure that's clear, do really, really well in the technical part, the evaluation, the benchmark. And so we marry those two things up and that's how we get enterprise deals done. And then the last thing I would note is many of these companies procure in a certain way. They have standards, they have protocols, they have contracts. AI is revolutionizing the way that software is, is, or technology is, you know, provisioned and, and, you know, what access looks like and what a contract would look like. So I'm very sympathetic to those people in procurement or legal inside a large company that have a job to do, that have their template that works for SaaS because it's been honed for 20 years, works for software as a service, but doesn't necessarily work for AI. So we try to also make an attempt to be really thoughtful about working with those folks to get them over the line as well. Because look, they have a job to do. And so you want to wrap your arm around procurement or legal and say, we understand the positions you're taking. Let us help you get through your job. So again, it's driving to their own business outcome. But that in a summary, Cameron, it's just business outcomes. Win the technical sale. Understand, put yourself in the shoes of the buyer, whatever counterparty, the buyer you're talking to, whether it's procurement, legal, business person, executive, engineer, etc.

Interesting. I think I've just noticed one of your superpowers, which is the ability to explain the kind of complicated in tech to kind of the layman. You work really well in soundbites and just even using like electrical cord examples, like, oh, fuck. Now I understand what an API is like. It was just so— it's so simple. Do you, do you think that's why you're able to work at the executive C-suite level? I know that you, you kind of work with Richard, who's the founder. I think you said you work with the CTO and then I believe you said the other kind of third in that if there were three in a box is maybe the chief of staff or four in a box. Is that one of your superpowers, the ability to explain and communicate? Because I think you said earlier before we went live that you're not truly a hardcore tech person either.

Yeah, I think it's, it's a combination of being really intellectually curious. And whenever I get involved in a company, I want to understand as, as deeply as I possibly can, what do we do on a product and technical level? And I think anybody in a company, whether an executive on down, should have a, a vested interest in exactly what you sell. If you work for Coca-Cola, you want to understand the products that you, you make. You may not get access to the secret formula, but you have a pretty good idea of what it takes to get those components and put it together. And, you know, you have a relationship with bottlers that you may own or not own and how it gets out the door and why marketing is really important and how placement works and all those kinds of things. And that just makes life fun, is understanding how things work. And so I take that to any position I've had. So that would be kind of first and foremost. And so I was never a developer, but I'm reasonably competent and dangerous around technology because I've spent a ton of time buying businesses, looking at architecture diagrams, demoing products of using products, understanding how things are built and what differences are in terms of architectural decisions, code bases, delivery methodologies, so on and so forth. Because how else can I be competent and capable to lead folks if I can't put myself in their shoes, understand enough? So that's been one, is just the intellectual curiosity. And I think the second thing is figuring out ways— you've said it, I think, on your website or in some of your books on connecting the dots. If I'm connecting the dots for the entire organization, I've got to be reasonably competent in understanding most of the pieces of the organization, and then be able to bring that to the other parts and say it in such a way where it's easily consumable. So the executive assistant knows what an API is, and that's important. The sales team understands why we're building certain things. The engineering team understands the way that we sell and how we attract customers, and, you know, what things, concepts like annual recurring revenue and ARR or financial metrics are. And so the more that people kind of understand that, it's self-fulfilling, it's better. And so a lot of my job is doing exactly that. Intellectual curiosity to understand, because I just want to know. Ability to kind of abstract, connect the dots and synthesize and had a lot of practice.

I like it. Yeah. Well, you definitely have. Yeah. This isn't like your first time in working in a tech firm for sure. You've been in it for 20-odd years. So working with the team that you're working with right now, One of the lead roles that you mentioned is the Chief of Staff. I'm curious, it feels to me like it's become a title that too many small companies are using, or maybe even mistitling an executive assistant. The only time I'd ever really seen a Chief of Staff before was the Chief of Staff for the President of the United States. And I mean, I saw it on a, a TV show 30 years ago, but they certainly weren't an executive assistant. They felt like they were more of a traffic controller. They were more controlling a calendar. They were making sure that communication was happening. What's a chief of staff and what's the size of U.com? Let's give us some perspective in terms of scope that you can talk about. And then what's a chief of staff do at a company of your size versus an executive assistant or whatever other titles they might have?

Yeah, it's a great question. And we're gonna be a little bit, uh, you, you'll hear in a second why we've got a chief of staff at, at our size. And then I can go on and talk about, you know, perspectives I've seen in other, other versions of chief of staff. So we are about 120 people. So pretty, pretty reasonably sized Series C company. We've got all the AI growth that you would want. So 10x the revenue last year, and we're in approaching 9 digits of annual recurring revenue. So not there yet, but we are powering our way there. So from all aspects, reasonably sized in a lot of angles, but not the type of company that would be big enough to necessitate a chief of staff. You're exactly right. Like a great executive assistant, I think they do a multitude of things. Ours run calendar. Ours also will run office. They'll run events. We have really two incredibly capable executive assistants who want more and more, and we give them more and more. They run the weekly all-hands that we have. So they do all sorts of different things that are kind of above and beyond just, hey, you're assigned to one executive, take care of their calendar. Yeah. You know, that's a job, but that's— there's so much more they can do and they can do. For a chief of staff, The reason why we have it is our founder, Richard, it's quite amazing. He's got his own venture capital firm. He's the founder and CEO of You.com, and he's the founder and CEO or co-founder and CEO of a frontier lab called Recursive Superintelligence. And they just raised very publicly about $650 million on a $4 billion valuation recently. So he's got 3 businesses. And so part of the chief of staff's job is How do I figure out what is most important for Richard to do across the 3 businesses? And then there are certain things that he does, a lot of speaking engagements. He gets asked often to participate in public events and things of that nature, just given that he's been working in AI on the frontier for about the last 16 years and is one of the more cited authors in some of the early works that were really formative in bringing what we now know as brings artificial intelligence and large language models to the fore. So the chief of staff really, you know, acts as that, as that, you know, thought partner to say, what's priority? How do I ensure Richard is well prepped to address that priority? In some cases, that can be scheduling. In a lot of cases, that is, you know, we've got to go engage investors on the road because we're raising capital for recursive superintelligence. How do I, how do I manage Richard's time? How do I help in that process? So it's, it's like a, How can I put it? I mean, you've 3 or there's 3 or 4 roles in one. There's a, there's a business analyst, there's a strategist, there's a, you know, personal COO light. There's, there's a scheduling element to it. And we, we pulled the guy Ryan out of, um, being an investor. He was a venture investor. So it's perfect because a lot of what we do is, you know, capital raising.

Okay. So help, help me understand this. I've always said that a person can only sit on one more than, or sit on one toilet at a time. You try to sit on more than one toilet, it gets kind of messy. Um, I got misquoted recently and someone said that I said you can only shit on one toilet at a time, which I did not say. I said sit, but either way it gets messy. How the heck does he work? Like the VC firm, I can kind of understand. Um, but recursive, especially raising that kind of money, that kind of valuation. And then you at the size that you're at both series, you know, Series C for You.com. How the heck does he do that? And how does your board even allow that? I mean, I guess Elon. Yeah. So if Elon's doing it, everybody else can too.

Elon can do it and Jack Dorsey can do it. And there's, I think, handfuls of people that can do it. Part of it, and this was a little bit of the attraction of me coming to you.com, is if you've got somebody that can focus and has the appetite to focus on an incredibly wide breadth of the day-to-day, you know, running the engine for U.com. He's got, you know, similar, he's got more co-founders at Recursive. So there's a, there's a whole, the whole team there. Um, but with, with U.com, uh, that's the beautiful partnership that he and I have is he likes to do certain things. And this is the relationship that I think makes sense for CEO and COO. He likes to do certain things, which is, which is I want him to do. Is ultimate North Star vision, big PR, engage big customers, large technical problems, and I do everything else.

Got it.

And that's perfect because I have a tremendous appetite to do many, many things. I want to drive business forward. I love owning go-to-market cycle. I love owning product. I love owning the operations, putting those three things together. And he and I work really well together because there's just lots of things that I'm perfectly happy to do and there's there's things that he would do but would prefer I do. So that's the happy marriage. And I think unlocks his ability to then apportion his time appropriately. And that's what I tell him is like, look, I want you in high leverage, high alpha. And then if it's not high leverage, high alpha, it's going to be important, but maybe not quite there. I'll take it.

Yeah. Stay out of the way. Stay out of my swim lane. It's interesting. I spoke about that in my newest book. It's called The Second in Command. It came out a couple of years ago where I talk about the yin and yang approach with the CEO and COO. Part of it is deciding on roles and responsibilities, who's doing what. And you guys have clearly, clearly delineated that. But it also, I think, answers to me why you chose this COO role versus moving into a CEO role at some new company. Like you said, it's because you are kind of the Gwen of SpaceX, that you, you're really here running the business while he's doing again some of the high alpha stuff. But you are really— would it be fair to say that you are really there running the business?

I think it's fair to say I run a— I am running a large force in the business.

I'm—

yeah, I, I, I— yeah, there's a nuance in it. I would say yes, I'm, I'm probably running the business, but look, I report to Richard. He's the CEO, he's the founder. Uh, I really have a great relationship with him, and so it ultimately is one of these— it is very symbiotic yin and yang, and I think that's why we, we are very compatible because Neither of us have a particularly big ego about it. We just want to put points on the board and get stuff done. And so, you know, part of my job is how can I empower him to do the things that he can do best? And for him, it's, I know Alex wants more and more, and how can I give Alex more and more? So you're exactly right, though. I— alternatives to You.com are go run mid-sized software company as CEO. And I thought long and hard about that, and I felt like this period of time, particularly in technology, in AI, getting into this arena and aligning myself in a space that I thought was incredibly valuable in search and was probably a little bit underappreciated. And then a founder like Richard, who both I respect and admire as a visionary, but also naturally has set himself up to say, I really need somebody like you to take more and more. It just worked really well.

Did you know him prior, or how did, how did they find you, or you find them?

Yeah, I met Richard through a board member, which is always kind of a good thing. Is we had a mutual, uh, friend. One of my, one of my friends has, has been, um, uh, has been a lifelong friend for 20 years. He was on our board, was led their Series C, and just in the course of a cup of coffee, he said, oh, by the way, I've just gotten on the board of this really interesting business. I think you and the founder would hit it off. Are you open to meeting? And my default answer is typically I'm pretty open to meeting just about anybody at least once, because you never know where it goes.

I moved my residence and my company to Dubai 4 years ago, and that's literally the default for everyone in Dubai or Abu Dhabi is yes, because everyone has moved there to, it's kind of like going to the Bay Area in '95. Like no one was from there. Everyone moved there. Everyone was on this perpetual motion machine and we said yes to everything. But it feels like so many people in like in New York especially don't say yes because you're always gauging like, why should I say yes? I'm protecting my time. What are they looking for? I love that that is your default answer in a market where typically yes isn't the answer.

You just never know. I mean, you never know when you open a door and the worst-case scenario is yes, you spent 30 minutes or 45 minutes and one of you paid for the cup of coffee and you had a pleasant conversation, but you just never know where these things lead. And the other thing, the instinct that I've had is And this is kind of just a human instinct more than a business instinct, but you just help people. You figure out ways to be helpful. You make an introduction here or there. You try to help people. You try to provide advice. You just never know when it gets repaid. So that's also my default is if someone asks me for help, I will likely try to do my best and help.

That's been my default as well. My dad, um, one of my dad's mantras was the answer is yes. What's the question? He was, he was just, he was just very helpful and very engaging and very, and that was probably one of his skill sets as an entrepreneur. So when you came in as COO for You.com, um, my guess is that there weren't 120 employees, but there weren't 3. How many were there when you joined and what was it like coming in into an existing team over top of an existing team? And, and what was your first 90 days like coming in?

Yeah, it's, it's a great question. This has become interesting too, because there were actually 135 people when I came in.

Ooh, this is going to get good today.

So, yes, exactly. So what we had done prior to me joining was we were going after the enterprise with the API business I talked about, which has long been the significant majority of our business. But we also had this other business line that had kind of arose in 2025 timeframe. Which was building custom agents and providing a chat user interface or UI for enterprises. And the reason we did both of those things was the ultimate starting of u.com back in 2020 was to provide a consumer chat user interface. This is pre kind of OpenAI's, you know, revolutionary announcements in the '21 and '22 timeframe. This is pre-Perplexity. And their progress with consumer, and then pre-Anthropic and all these other things. And what you need to do in consumer life is you need to have a massive amount of capital for either compute in AI or marketing. And u.com had not raised the massive amount of capital to do those two things, although our UI was better in many ways, better answers, better responsiveness, et cetera.. And we found the enterprise had pulled us and said, we want to use this. And part of it was accuracy of answers, but part of it was we were model agnostic. So you could, you could use any of the large language models, whether it was Gemini, you know, Claude, OpenAI, you know, Qwin, whatever you want, KIMI, all those things. And we were having some progress there and also having some progress when customers would come to us and say, this is great that you're selling me this, this user interface. It's great that you're selling me these APIs. Gee, wouldn't it be amazing if you could wrap those APIs with a custom agent? Because I'd also want agents to do certain things in my company, and I don't quite know how to get that done. And sometimes in life, when customers give you money, you do things, which is not always good. So we had this other business, we're building custom agents and, and providing the user interface, small minority portion of our business. And you probably know from your experience, focus breeds success. And so when I came into the company, I said, look, this Search API business, this Google for agents, the market's very compelling. It's large, it's growing, it's underappreciated, all the things we talked about at the outset of the podcast. This is a great market. And we're really good at this because we were the first to get here. We've got great product here. We've got great traction, momentum, and growth. And then we've got this smaller business, not bad, like in a different world, that on its own is, is perfectly fine. We're providing a chat UI and some custom agents to, to enterprises. But that's less scalable because if you bespoke products like a custom agent, it's non-repeatable. It's hard to resell that stuff. And I looked at that. I said, we really ought to focus only on the APIs. And so to do that, how do I do that and, you know, separate the two, the two businesses? And we had this really nice solution where we created a joint venture We found a professional services partner that loves doing professional services for XAI Groq or ServiceNow or Salesforce or others. And they've started many, many businesses like this where they will, they will spin up an entity that basically does services around a larger corporation. And in our case, they'll do services around U.com customers or frankly other AI customers. And as I was able to take a portion of the team about 10 folks, put them into the JV, and then we were able to go through a nice communication with customers and say, hey, look, we're not going to focus on this business, but this joint venture is. And so here's, here's the glide slope off. So we went from about 135 people down to, to 1, like 110, because we also took the opportunity, I took the opportunity to exit some folks who really were really capable at enterprise software and and those types of motions, but not as AI forward, engineering forward, developer forward, those kinds of things. And so we took that opportunity as we did the little separation to also really, I think, unlock some folks that have better potential elsewhere and do a reset. And then we hire back to 120. So that was the story of getting from 135 to 110, back to 120, and really just taking what we were doing 90% of and making it 100%. Focus breeds success. And then I tell you the power it unlocked within the company because when you tell people we're just doing one thing, we have one mission, one North Star, which is also incredibly aligned to Richard's personal North Star he's had for 20 years, all of that stuff in alignment, everybody gathered around one singular mission, boom, just exploded. So that's been the thing. That was my first 90 days and the second 90 days was now go-to-market and putting the pedal to the metal.

That makes perfect sense. I love the whole, um, the whole principle around focus. I mean, I read something about 40 years ago called The Only Person Who Gets Anything Done Is the Monomaniac with a Mission. It's that monomaniacal focus. Um, but I also like the whole cut deep, cut once. I mean, if you're going to be moving 10 people out, you may as well get rid of any of the dead weight that you can, or the people that aren't completely aligned. It's a chance to kind of, you know, make that, that huge cut. I'm also still a little bit curious though of, of When you came in as COO, how did you get the current team to know you, to like you, and to trust you? And then how did you also get to know them and like them? And how long did it take, or how long did you give yourself before you started to make big decisions? Did you come in on day one, start swinging for the fences, or did you come in on day one and, okay, let me get to know the people and the history and the, like, does that make sense?

Like, It makes complete sense. And I took the following approach, which I've taken before, and I highly recommend it for any listener that's out there thinking about coming into a new situation and how to encounter it at any executive level, frankly, is I did a bit of outside-in for about 4 to 6 weeks. So thinking about Udemy.com before I joined, doing as much research as I could possibly, you know, what do we do? What's our positioning? Who do I know within the company? Who are competitors? Who are the alternatives? As much as you possibly can. So at least you have a baseline level of competency. And then the first 30 days of my 90 days is all about listening. It's the Socratic method of learning. I talked to as many people as I possibly could. So within a company at the time of 130 people, I talked to probably 45 people. I did one-on-ones with 45 plus people. I talked to as many customers as I could. So I talked to a couple dozen customers. I got as close to the products as I could. So I just fiddled around and read and touched the products because businesses at the end of the day all boil down to people, products, customers. And so to me, the first 30 days as an executive is get close to those three things and do it in a very organic way. And then at that point, The instinct I had before joining, which was we really ought to focus on APIs because it's just a better business and we're, and we're, we do much more of it. It's where the significant majority of the revenue comes from. It's where the edge is. It's where the, the products are, are the best. That instinct, then after 30 days was validated. And so then at that point, the next 30 days was I went back to the management team. I said, okay, great. I've done this listening tour. I've talked to 45 people. Here's what they say. To a person, they said, man, if we only did the one thing and the one thing being APIs, we could really unlock something special. And I kept hearing that over and over. And when I talked to customers, the happiest ones were the ones who were API customers. And then when I looked at our products and I thought, where do we have sustainable competitive advantage for the next— in AI land, 2 years is a long time, but I'm trying to think about 3, 4, 5. Like, where can I squint and see, like, a moat? APIs. So I came to the executive team and said, I really— here's what I'm hearing. And oh, by the way, then I backed it up with data because I looked at the pipeline. Where are our best win rates? Where's the best velocity? Where's the biggest pipeline? Look at the customers. Where's, where's, where's the best retention? And so you have all this data and you say, all right, the organization's saying this, the customers are saying this. I think we all have this instinct around product. Here's what the sales and pipeline data say. I think we ought to do this. And so then we worked for 2 or 3 weeks to go through how can we do this, which was how do we eloquently tell some amount of customers we're not going to focus on the thing that we sold them previously, which is delicate because I respect the relationships that are built and want to honor those. How can we treat people with care as they may not be with the organization any longer? They may be going out into this JV. How can we set up this JV? So we spent the next 30 days doing that and then we pulled the trigger on March 23rd, not that I remember the date. And from there we went.

I love it. And I love that you actually did some of, of your understanding the company before you joined them. That makes perfect sense on how you kind of fast-forwarded the 90 days. But then I really love, and I'm completely aligned on that first 30 of only listening, talking to team members. The only thing I ever remember from, I think it was grade 9 or grade 10 science class, was like state the hypothesis, test the hypothesis. And that's kind of what you did. In the— like, but so many people, I think, make that mistake where they come in before they really know the people, before the people know them, and they come in with that big idea, even though it's right, but they cause too many ripple effects. And I think you did it— well, I know you did it in completely the right way. Last couple of questions I've got is, what do you focus on day to day, and how do you kind of orbit the minutiae? I had someone tell me one time that I majored in the minors, and they were so right. I was trying to get every franchisee at 1-800-GOT-JUNK to have the proper email signature. And Alan Reamer from, from Philly said, you know, great, yes, but you've got, you know, 100 franchisees that don't have a marketing budget, a marketing calendar, a marketing plan, and you're worried about the fucking signature. Major in the majors. How do you orbit, orbit that? How do you stay focused on the important stuff and not get sucked into the day-to-day of every decision and every meeting?

That is the classic question. And it is something that I think about almost every day and every week about how do I use my time in the most effective way to drive the mass— the most amount of value or the most massive amount of value for the company. What I try to do is I'm incredibly structured with my own time, and I like to be very calendared and compartmentalize what I do. And so one of the things that I will do is at the start of every week, I've got my to-do list and there are 3 or 4 things that I know are the absolute biggest ticket things that we need to focus on. It may be large customer engagement. It may be a large product decision. It may be large prospect. It may be reshaping the way that reporting goes. It may be empowering a team to fulfill something. So it's what are those big ticket things that if we just ignored everything else, and I wasn't involved and it ran on its own, what do we have to get done that ultimately drives the P&L and drives shareholder value? Because that's what I've got to be directly impacting those things. And so those are the first things, and then trying to figure out how to apportion my week and my time focusing on those things. And then there's kind of a second level of things where it's executive overlay. So it is breaking ties, making a decision on something, being the final say on a legal document, thinking about the strategy of a partner, opening up some accounts for the sales team where I've got direct relationships. Those things are really important and they can lead to the bigger things. So you don't want to forget them, but there can be 10, 20, 30 of those, uh, you know, a week, a given week, and Sometimes they don't always get fulfilled. So again, you're kind of like prioritizing those things. And then at the bottom is all the day-to-days. And I joke to people, the life of an executive is every day you wake up, there will be a surprise. You don't know if it's good or bad. You just mentally prepare yourself, it's going to be bad. Something bad will happen today. You are responsible for dealing with it. And so then there's no emotion, right? You just like, you walk into it and it's like, Ah, this thing happened. Okay, no worries. Let's figure it out. No problem. And, and so there's like that, that there's that kind of mentality. But the other day-to-day thing is there's just lots of these little things, as you, as you said, the minutia, right? Majoring in the minors. And so what I try to do is I try to box when I look at Slack, I try to box when I look at email, and I try to chunk it. And I'm a huge fan of I'm anti-multitasking. And there's like so much literature and research that shows you, you just degrade your ability to make great decisions if you're looking at 2 or 3 or 4 different things at the same time, or if you superficially float by things and don't kind of dive in. And I really, I don't like, I enjoy Slack because it's a great form of communication. Teams is the same thing, but people making decisions on Slack and Teams, like you're not thinking it through. No, decision-making is not that. And so I typically will not look for 2 or 3 hours because I've got meetings I want to focus on, or I have a thing that I want to read, or I have a decision that needs to be made, or I've got a customer engagement, whatever. And then I've got a window and I will go through my Slack and emails. And often if I read something and determine this requires more than 1 minute of cognitive thinking, I should not respond superficially to this person. I will unread it and deal with it later. Oftentimes in the morning, or at night when I'm fresh after the gym in the morning at like 6:30 in the morning or at night after my daughter's gone to sleep and it's quiet and it's 8:30 because those things deserve time that I don't want to superficially flow by. So that's kind of my— like you got the start of the week checklist, you get the big huge alpha things you got to do, you get the medium things you got to do most of them, and then you got to time box the kind of day-to-day leaving some buffer for the surprise. But yeah, I'm a big, I'm a big, like, on the day-to-day minutia, I unread things all the time because I'm like, I don't care about the bubble. I don't care about the dopamine hit. Like, social media, Slack media is not going to get me. I don't need my stuff to be read. I need it to be right.

I like it. There was, there's, there's some huge, huge, huge nuggets in what you just covered there, which would, thank you. A couple that I want to just, just go back to. One is the idea of the top 3. I mean, even if you're just doing 3 big things on a weekly basis, that's 156 huge things that you're doing over the course of a year, which is way more than most executives ever get done. The second one was around expecting the unexpected. When, when we were building what's now called Gerber Auto Collision in the US, Boyd Autobody in Canada, it's now the largest collision repair chain in the world. My partner Terry, said that he would always expect the worst or expect things to go sideways. And when they did, he crossed them off his list. And I said, well, what do you mean? He goes, you know Greg in our office? I'm like, yeah. He goes, Greg pisses me off every day. I'm like, yeah, I know. He goes, so I wrote on my to-do list one day, get pissed off by Greg. And he goes, at 11 o'clock, Greg came in, did something, pissed me off. And Terry goes, I laughed and I checked it off my list as completed. And then I dealt with the issue. I'm like, dude, that is so brilliant. It's ridiculous. Like, it's just so, you know, so it's It's kind of, but I think that's really important as a mindset because stuff does happen, stuff does go sideways. And if you're expecting everything to go perfect, you're, you're completely setting yourself up for failure. It's why, by the way, most perfectionists really struggle at being entrepreneurs is they've never had to deal with adversity before. My wife got better than a perfect GPA. I didn't even know that it was a thing. She had a 4.2 or 4.3 GPA. I had a 2.7. I mean, I was dealing with failure my whole life, so I'm used to it. All right. I want to go back to the last little nugget for yourself. If you were giving some advice to the younger you, the 21 or 22-year-old Alex starting off in your career, what advice would you give the younger you that you know to be true today?

You have two ears and one mouth, and that is the perfect ratio.

Use them in that ratio. Yep. I love that. Alex Trippett, the COO for You.com. Thanks so much for sharing with us on the Second in Command podcast. Really appreciate all the, uh, the wisdom and the time today.

Thank you, Cameron. Really appreciate your time.