238: He Built an 8-Figure Software Company AI Still Can’t Replace with Dean Guida

Dean Guida started Infragistics at 23 to build UX/UI tools for professional software developers.

Thirty-seven years later, the company operates across six countries, its software is used by more than two million developers, and its customers span the entire S&P 500—including Fidelity, Morgan Stanley, Exxon, Intuit, and Bank of America.

But AI can now generate functional software in minutes. So what prevents a company like Infragistics from becoming obsolete?

I wanted to understand which parts of software AI will commoditize, where lasting competitive moats will still exist, and why Dean believes the idea that software is disappearing has been dramatically oversold.

We also talk about how he built a multi-8-figure company without outside capital, why he might raise money if he started again today, and what founders need to build once grit alone is no longer enough to scale.

Mic Drop Moments

• “Software is the key to stitch everything together. They say, ‘Oh, software’s going away.’ Are you kidding me? That’s such a silly statement.” – Dean Guida

• “Driving growth and making money is hard. I don’t care who you are, how great you are, how much experience you have. That never seems to get easier.” – Dean Guida

• “Really good business concepts are easy to understand, but hard in practice. That’s where repetition, working through it, and involving the team is so important.” – Dean Guida

• From $25K to Multi-8-Figures
• 37 Years Without Raising Capital
• Why a Bootstrapped Company Has a Board
• Inside Dean’s Quarterly Board Meeting
• What Infragistics Does Today
• Software Moats in the AI Era
• Where Token Costs Are Really Headed
• The $50M Internal Innovation Fund
• When Grit Is Not Enough to Scale
• Using Micromanagement the Right Way
• Aligning a 250-Person Global Team
• Fixing Meetings That Waste Time
• When Performance Slips as a Team
• The Easiest Way to Wreck Culture

Brad Weimert: Dean, you have bootstrapped your first company, Infragistics, from $25,000 to a multi-eight-figures. You sell to predominantly Fortune 500 companies. But since then, you’ve gone through this windy road of launching new products, new companies, all through that lens. You also are the author of When Grit Is Not Enough. Welcome to the show. Thanks for joining me, man.

Dean Guida: Yeah, thanks. I mean, I think some of the unique things that the path we followed is 37 years ago, when I was 23, we founded the company in building UI components for software developers in Windows 2.0. I mean, that’s so long ago. People don’t even probably know what it is. But, like, the innovation to Windows 3.0 is where you had overlapped windows. I mean, that was innovation back then. And we never took money, and to this day, we’ve never taken money. And today, we have three companies. Our user interface UI component is working in agentic code generation for building out really data-intensive applications that we saw. Actually, mainly our biggest audience are customers or other software companies.

But we sell to all the Fortune 500, and so, like, we’re in all the trading apps, Schwab, Fidelity, Morgan Stanley, and a lot of commercial apps, Intuit, and others. And then we have two other big brands, Slingshot, which is an AI agentic go-to-market platform, and we have Reveal BI, which is an AI analytics component SDK that we sell to mainly other SaaS software companies, so that they can embed AI and embed analytics right into their applications.

Brad Weimert: Well, I want to talk about kind of that windy road. So, you have adjusted course a number of times, from creating this UI component library 25 years ago to SaaS products, to kind of an internal fund to grow things. How do you know when you should just close something and start a new company or iterate?

Dean Guida: Yeah. I mean, I think it comes way before closing down a product line, and your team needs to know it that you’re going to start investing in a different product line, because you’re kind of seeing around the corner and seeing the future. But yeah, a lot of your revenue and your R&D is going into the product that is bringing in all your revenue. But you have to start shifting talent and resources and investment in future technologies. And so, that’s what’s kept us around for 37 years is that ability, but it’s never easy, and we’ve made wrong bets. And in a good and a bad way, we’re really passionate about software. That’s good and bad, where we like love software, and we love building software, which is good, and it’s bad.

Brad Weimert: Interesting time to love software.

Dean Guida: So, it’s a double-edged sword, but it’s me and a number of others, since we love software, just staying connected with what everyone’s doing and where technology’s going, and trying to figure out the opportunity where we can compete, add value, and have a competitive advantage, which is the hard part.

Brad Weimert: So, I want to dig into kind of the arc and the different products, but you have bootstrapped the entire time, and I probably ad nauseum talk about my affinity for bootstrapping, but I have this curiosity around raising too. For 35 years, you’ve elected to not raise capital. Has there ever been a time when that’s been tempting?

Dean Guida: Yeah, I always reflect on that. Should we raise money? Even today, we would probably be bigger than we are now, and so it’s always thought about. In the early days, it was never thought about. It was just like grind it out. We’re going to make it. I have some points where you don’t think you’re going to make it, and then something good happens. And then go for stretches where you don’t think you’re going to make it, and something good happens, and then you finally like punch through, and you have a sustainable business model. So, it really wasn’t until, I mean, I’ve been doing this 37 years, and so probably in the last 15 years, I keep reflecting, “Should I have taken money? Should we have taken money?”

And there’s a hard choice, because not taking money, we kind of make our decisions based on where we, you know, not external pressures of hitting certain revenue targets with certain hit multiples to exit. That’s a whole different pressure versus really investing in people, investing in product, having a little bit more patience, and figuring out the market, and not having that external pressure. So, that’s like the good side of it. The downside of it is that you don’t have as much capital. When you take risks, like all for 37 years, when we took risks, we had no safety net. Like, if we fall, we hit the ground. It’s going to hurt. And so, that creates a sort of edge too, where, like, take care of the customer. Who pays us every day? The customer. We have to deliver value. Every day, the market shifts in what value means. It’s harder today. It’s always been hard, but today it’s even harder.

Brad Weimert: If you were to start over today, would you bootstrap today, or would you raise money?

Dean Guida: Yeah, that’s a good question. I think I’m in a different position, where I have money to bootstrap again, so I wouldn’t have to have that. But at the same time, there’s value also of taking money, which I didn’t mention. Like, I know a lot of private equity and a lot of people, and I really like them, and I’ve had met them many times in dinners. They still court us. And the value is that they have all these go-to-market experts on their staff, which is immensely helpful in your own operations to help you win. So, I probably would take money now if I started over, because you can go faster, you can do more, and you have this external party that can also add value operationally.

And then it probably will be a little bit more pressure. I’ve been reporting to a board for 20 years, so I’m good at all that, but I think it’s a little bit different when it’s someone else’s money and they just want ROI, and maybe not as patient or understanding, which puts more pressure on you, which is good and bad.

Brad Weimert: Well, you said you really liked them, but you haven’t taken their money yet, so.

Dean Guida: That’s a really important point, Brad, because they are so nice to me. I mean, it’s unbelievable how nice they are, which I know the second we take their money, a new person will show up the next day. He told that, I know that, and so, yeah, that’s 100% true.

Brad Weimert: Well, you said you had a board, but you didn’t raise money. How’s that work?

Dean Guida: Well, about 25 years ago, I merged my company with my number one competitor, and so there was new shareholders, and I remain CEO of the company, but then we created this fiduciary board. And quite frankly, the rhythm and process is really great, where we have to create strategic plans, we have to create annual plans, and that quarterly rhythm of just reporting out our problems and where we’re focused and our goals, and then the approval of the cycle of strat planning and annual planning. It’s a good process, and audited financials, and tracking key metrics, and we have an internal fictitious stock price, not fictitious, but after like formulaic, financially fictitious, and it’s just for maybe internal options. It’s not for more than that.

And so, it’s been a good thing, and I wasn’t good at it, like everything. Like, you’re not good at anything until you do lots of repetition. And so, it took me a while to get good at it, and it’s been beneficial in running the company.

Brad Weimert: That’s an interesting construct. Do you think that it would be helpful for all entrepreneurs to create some sort of board to hold them accountable?

Dean Guida: I think it’s valuable. I mean, you can create an advisory board, which is just a diversity. Like, what’s so important I’ve learned over the years is diversity of thinking. And so, if you can get a diverse board that thinks differently than you, and I’ll answer your question directly, but like I used to hire everyone like me, and we got along. We always made the same decisions, and life was great, but that was the problem. Like, we would always solve the problem the same way. And then I went to the Center for Creative Leadership, which was eye-opening to me. And one of the things I learned there was I need to hire people that are not like me and don’t think like me, so that as you’re solving problems, they’ll come up with an idea to go right, and then you guys build on that.

And so, circling back to your question, yeah, I mean, when you have outside advisors and you’re very strategic about who you want to put on there, like what are competencies you don’t have, or what experiences you don’t have, or what markets that you don’t have a great experience, and having advisors will really help. And then getting that external outside in thinking and commenting is really valuable. And then, if it’s a fiduciary board, I believe in that now. If you had asked me this before that, it’s like extra work. I don’t want to do it. But now that I’ve gone through it, it is valuable. It creates a discipline in thinking and running the company.

Brad Weimert: Yeah, I was just talking to somebody earlier today about how fundamentally, as an entrepreneur, bootstrap entrepreneur, there is no accountability, right? The accountability is to you, right? And you can say you have accountability to other people, but ultimately you’re reporting to you. So, I think having a board there seems like a pretty strong measure of accountability that you don’t otherwise have when you’re bootstrapped.

Dean Guida: Yeah, and it makes you prepare about thoughts in a structured way. It makes you talk about real issues. And I mean, you have to have a trusting board, so you’re just not going there and doing a dog and pony show how everything’s great, and hiding all your problems, and that’s just a waste of everyone’s time. Don’t do that. Because everything’s always hard and driving growth and making money is hard. I don’t care who you are, how great you are, how much experience you have. That never seems to get easier. And so, if you come at it from that point of view, just thinking about how to write a board packet, and like, we send it out a week in advance, our CFO writes up a whole MDNA, and I write up a whole board packet, and based on the quarter, whether we’re doing action or strategic plans.

But the important thing is we send out a week in advance, and we’re not presenting like everyone reads everything, and then at the meeting you’re talking about problems and how are you trying to fix things and get different perspectives, so it becomes very valuable. In the beginning, even my board members weren’t good at it. It was like they didn’t read the information, or they’d want me to present the information. I was like, “That’s just a waste of time.”

Brad Weimert: Yeah, okay. So, what is the board meeting like? How long does that last? So, when you say board meeting, I think about sort of quarterly planning, and how I structure quarterly planning, and how inevitably inefficient my quarterly planning is, and everybody prepping and reading makes lots of sense to condense that space. How long is that quarterly board meeting?

Dean Guida: Yeah. I mean, we have an agenda. It’s anywhere from, let’s see, nine to two, so it’s like anywhere from three to four hours. And so, it kicks off where I have the first hour, which is what I prepare to like, what are our problems, what’s the future look like, and whatever issues are happening. Usually, our core like drivers and investments don’t change much, but if they did, I’d talk about that, and they do change sometimes. So, I have the first hour, and the first hour usually goes probably longer than an hour. And then after that, based on the quarter, we’ll have the audit committee checking in. We’re audited every year, and that’s like 30 minutes. We’ll have different agenda items.

We’ll have in Q2, I present a kind of strategic P&L future three years’ P&L of where our investments are, where our expenses and spend on a very high level, and the strategic drivers of that. So, that happens in Q2. Everyone buys into that, and then in Q3, the main topic is delivering our strategic plan. And then in Q4, delivering our action plan, how are we going to support that strategic plan the next year? And it gets a lot more serious because that’s where we’re going to spend money and burn cash or make cash, but it’s to support the three-year strategic plan. And then our strategic plan is usually a bit more optimistic, because why wouldn’t it be, but then our annual plan needs to be more like stretch goals, where it’s always more. We always have to do more in terms of revenue, but so you’re stretching it.

But you don’t want it to be too optimistic, because there’s nothing worse with your team reviewing where you’re at on your goals, and you’re 30% below plan all the time. That’s just debilitating and is a waste of time. But at the same time, everyone wants more money, it costs more money, you need to grow the top line, so you try and get that sweet spot of stretch goal in your annual plan, but that’s when it really matters, so we kind of go through that. And then the board sets my pay, so that’s talked about in Q1 and Q2, and then it has to be locked in the Q3 board meeting, because I need that to flow into our budgets.

Brad Weimert: Yeah, man. I mean, that is significantly more structured than most bootstrap companies.

Dean Guida: Yeah. We’ve been doing it a long time. I mean, we’re, like I said, revs of anything makes you better, and you forget how hard it was to do something the first time. And after you’ve done it so many times, you think that it’s easy, and then when others have to do it, and I have no patience, but you have to have patience. Like, people have to have those revs, and then they get performant. And so, yeah, it was not easy in the beginning, but after a lot of revs, you get good at it.

Brad Weimert: Well, my ambition generally, when I’m talking to people, is to have very quick questions in the beginning, but I had to stop and talk about that one, because that’s just fundamentally a different approach than almost all bootstrapped entrepreneurs. So, the idea of going through that structure, the board, I think, is awesome. Let’s back out to Infragistics. So, you’ve been doing this forever. As a starting point, what does Infragistics do exactly?

Dean Guida: Well, we build UI components for the different web stacks, React, Angular, Blazer, web component, and we have open source UI components, and then we also have commercial components that we sell, so those are like spreadsheets, hierarchical grids, doc managers that require to handle lots of data, virtual data that Claude or Cursor or Copilot or OpenAI, they can generate a quick grid. But when you’re dealing like we’re probably in almost every trading app out there, we’re going to have the fastest grids and really functional. So, data-intensive applications use our components, and we have over 2 million developers using our components.

And we’re in Schwab’s trading app, we’re in Fidelity’s trading app, Morgan Stanley, Bank of America, where Hitachi built this app, where we’re controlling all the power for Japan and Poland. And then a big customer of ours is actually the Js, which is in Japan, that controls all the bullet trains, subways, and trains, use our software to build that. We’re in probably 40 different ERP systems. We’re in all these different commercial apps that you probably use all the time. And then we’re really good at design to code, so going from like design systems into production code. We’re really good at that and dealing with design systems. And since the beginning, that’s been a 37-year product that has evolved.

I mean, in the beginning, we’ve done everything when you talk about component models and platforms, from desktop to web to mobile to now everyone’s focused on web, but also we do a lot of work now for AI with MCP servers, so that, like, reducing token cost, first time pass on getting a beautiful functional UI that right every time with accessibility built in, with performance built in, with theming built in. And so, that’s what we just shipped a couple of MCP servers over the last couple of quarters, one for our UI components and another for theming and for React, Blazer, Angular, all the different web stacks. That’s a big product liner.

Brad Weimert: You’re clearly a nerd, and that would be incredibly valuable in the early days to say, “Hey, here are these elements that don’t exist anywhere. You have to come to us to buy them.” Immediately, when I heard that, and you articulated it right away, but I think that for the era that we’re in, it’s June of 2026 right now, you look at Claude, you look at Cursor, you look at any of the AI tools out there that will generate a lot of this stuff automatically, but what you said was specifically the market at the moment is data intensive architecture, right? So, you’re looking at how to visualize data that is really intensive on the back end, you’re handling a lot, probably across a bunch of different tables, or lots of volume.

Dean Guida: Yeah, and speed. And so, if you’re building a trading app, or if you’re building a healthcare app, or if you’re building an insurance app, it’s just a lot of data, and you have built-in virtualization, and have really fast performance scrolling, like we’re the fastest on the market, millions and millions of rows. And then to have advanced features like column pinning, exporting to Excel, and all kinds of different cell type and filtering, you can’t do that, actually, with Claude. You could try, and you’ll probably spend, I don’t know, 20,000 in token costs, and you still won’t get the accessibility, which is really important, the security.

Brad Weimert: And you’ll break it 15 times through the process.

Dean Guida: Yeah. And that whole loop of like adding that feature, breaking this, adding that feature. So, it’s very productive to like get stuff done, but not build commercial class components that you need. And so, we know, like, we go to a lot of developer trade shows. We were just at Build in San Francisco, and yeah, everyone knows, like, you really need to use frameworks and components along with agentic code generation, because why do you want to support that? Why do you want to waste tokens to generate that when there’s already, like, for us, for $1,000, you can have this that’s tested in all these ERP and financial apps and insurance apps. And yeah, Claude or Cursor, or whatever, they’ll generate this div to table. Oh, try adding a million rows to that, or try adding 100,000 rows to that. It’s going to break. It will not break. It won’t work.

Brad Weimert: So, there are two things that come to mind there. One is kind of like talking about the future of things. The other is I want to highlight to anybody listening that the reality of trying to digest or play with lots of data is compressing to the lowest common denominator. And what I mean by that is that we are going to be more and more and more and more in a place where the expectation of people is that you are going to be able to handle tons of data. So, like the examples that you’re using right now are like, oh, trading platforms, insurance, healthcare, like these massive data sets, but the reality of the world is that’s where we’re going.

And so, just like your phone was capable of doing nothing 20 years ago, and now it’s got a terabyte in it, or whatever, of storage, right? The same thing’s going to happen with just data processing. So, the capacity to manage that stuff is becoming more relevant to the lowest common denominator. The question for you is, immediately, when I was looking at your businesses, I thought, what is the defensibility moving forward, and how do you look at the democratization of software? So, how do you look at… As these code generation platforms get better and better and better, what will the moats be, and where will we be in five years with your business?

Dean Guida: Yeah. We see a huge moat around, like we have four businesses, but the UI component business that we’re talking about, the moat is there, like we’re a trusted brand, we’re going to support it. If you’re selling to the government, accessibility is important. Who wants to vibe code or agentic code accessibility and test it, and test it, and keep it up to date? Like I said, doing virtualization on data, you’re not going to spend. Why spend? And token cost is getting more expensive now, so it’s getting to be 10 times more expensive. Like, GitHub led with, we would spend. I mean, our guys are telling me, “Look, we’re spending per dev, like, a couple $100 a month per dev. Some guys blow their tokens out.”

And maybe we’re spending $1,000 a month with these devs. But they’re prepping me, like, “Okay, it’s going to probably cost us like 100,000 now,” and I’m like, “A year?” They’re like, “No, a month.” I’m like, “What?” Because everyone’s been subsidized by Anthropic and OpenAI to get market share, and now that they’re all going public, they’re like, the new… Fable, okay, they brought it back, but that’s 10 times more expensive. And so, it’s getting more and more expensive to have intelligence, but we code 90% of our apps identically and supporting our commercial software. But as everyone knows, when you get below the hype, you still need architects, you still need engineering, you still need product management, and yes, you can go faster.

But faster is not always better in terms of you have to think things structurally through of what you’re building and how it’s going to work. And so, yeah, we see a 5, 10-year easy moat, what we’re doing with our UI components, and it’s validated. In the beginning, we were scared, like everyone else, because everyone was like, “Oh, the whole workforce is going to go away.” Like, “Oh, really?” “Yeah, developers are going to go. No one needs developers anymore. No one’s going to need financial analysts anymore, and all these jobs are going to go away.” But they did too good of a job on PR, and quite frankly, it backfired because everyone hates AI because they don’t want to lose their job.

And it’s created this really panic, like for the younger generation like, “Should I go to college? If I do go to college, what should I study?” And so, they oversold it. I love AI. It’s unbelievable what you can do with intelligence, but the opportunities are so great. Software is the key to stitch everything together to, like, harness things, do tool chaining, to bring data sources in, and contacts, and skills, and all this stuff. I mean, there’s been so much hype that they say, “Oh, software’s going away.” Are you kidding me? Like, that’s silly. It’s just a silly statement.

Brad Weimert: I mean, I agree with you now, and in the short run, and you left the mark out for defensibility for five to ten years. I guess, even token costs, there’s evidence to suggest that those will drive down over time. I think we’re obviously in an expensive place right now, but so token costs would be a really relevant consideration moving forward.

Dean Guida: I don’t think it’s going to drive down once they go public. Where it’s going to drive down is local models on laptop models, models that are reinforcement learned, reinforcement trained, that are open source models. I think, like we already do this today, we have a lot of AI built into our products, and every task or every workflow doesn’t need the highest model that costs the most. And so, we’re already optimizing, and a lot of people are, to use different models for different tasks, because of cost matters. And future people are going to have payroll budgets and token budgets, but it’s always going to be a consideration. And plus, no executive or manager likes to not like understand cost for the year.

“Oh, what do you mean? Okay, I paid $20 a month for my ChatGPT, but now you’re telling me, like these toolings they’re blowing their token costs out, and now it could be $1,000 a month?” and that’s happening. It’s like the new pricing model is, yeah, predictability on user seat, which has a bunch of tokens built into it, and then when you go beyond that, you’re buying new packets. But businesses don’t like that, but it’s the only way to protect some of these costs as an entrepreneur or as an AI company.

Brad Weimert: Do you think that we’ll get to a point in the next five or ten years where, agentically, you can recreate the complex structures in a cost-effective manner?

Dean Guida: I’m not sure what you mean, recreate the complex structures. I mean, I think agentic is great. There’s a lot of power.

Brad Weimert: I mean, specifically your use case, right? So, you’re talking about some of the great, unique features that are super complicated to build, right? So, handling tremendous amounts of data very quickly with a very dynamic interface, virtually, right? So, that’s currently your moat. Do you think that five years from now, ten years from now, we will be in a place where it will be feasible for a coding agent to recreate that stuff on the fly, period, and if yes, in a cost-effective manner, where the tokens would be cheap enough that that would be disruptive to you?

Dean Guida: Well, I don’t think tokens are going to get cheaper, but they will get cheaper from like some of the things we just talked about. But I think frameworks and components always make sense for someone else’s problem to maintain and have reusability. We have this one guy on our team, and we have this product called Slingshot, which we’ve been building for eight years, spent tens of millions building it. And because we wrote all these APIs, and we have MCP server, over the weekend he used Claude, and he rebuilt Slingshot, and he said he did it in a couple of days. And he did do it, but he was reusing all this stuff we already built. Now, could have he generated all the stuff that we built?

Yeah, but like that’s so expensive. Why do that? So, economics comes into it. Even in the future, like, why not have someone… Here’s the CIO problem: everyone can create, and then they leave your company. I mean, do you want that mess where you have to have bugs and problems and new things come out that you have to add and change? Who wants that burden, unless you’re a software company? So, even though it’s easier, there are all these economics and maintainability jobs that are going to be there.

Brad Weimert: Yeah. Look, I think it’s an interesting conversation, because we don’t know where it’s going to go, but my general hypothesis is along the lines of yours, which is that we will probably find ourselves in a position, certainly now, but even down the road, where the frameworks or components or pipelines for things are what will remain, and then the other stuff will be created on the fly for whatever you want, but then it’ll always want to plug into something else, because why would you actually do it?

Dean Guida: Exactly. Like, the same thing with the data architecture, right? It’s like, oh, I can easily connect to data from multiple sources, whether it’s Salesforce or GA4 or Databricks, right? I can easily one-off connect to it. You want to do it in a performant way, and you want to do it in a data security way, you want to do it in a compliance way, in a governance way, and then you want to do it at a performance at scale. You need to build a really strong data architecture that’s feeding the AI contextually to have good output. Okay, you could vibe code that, or agentically code that, but unless you’re a serious architect, you just don’t want anyone doing that. Just because you can drive a Ferrari, you’re not going to go race around the track, like not if the stakes are high, right? If you’re going to race around the track for fun, okay, but if it’s running a business, that’s serious.

Brad Weimert: Yeah. Well, let me back out and talk about the other elements of your business. So, at some point, tell me about sort of the $50 million internal innovation fund, and how that came to be, and what the point is of it.

Dean Guida: Yeah, the point is that, like, we’ve been through so many technology change. I mean, this is the biggest, but we’ve been through so much. And so, we wanted to have a way and a structure to invest in the best ideas that our teams come up with. And so, we created that fund, so that we could choose and have money set aside that wasn’t for generating top line and already spoken for to be able to invest in these new opportunities. And that’s where our Reveal BI came out of, which is it’s an embedded analytics SDK that connects the data, does dashboarding, does AI agentic or not agentic, but conversational business analysis using AI. And that’s just another example of the other conversation, which is, “Oh, could someone just vibe code that product?” Not really.

And then, why would you? Like, you have a choice where to spend your time and tokens. So, like, if you’re an enterprise, you know how much technical debt you have that you should burn down? You know how much you have to say no to every business unit that you can now provide? Why would you build some fundamental horizontal technology? And so, it just comes down to choice of where you’re allocating time and money.

Brad Weimert: Okay. So, you’ve been in business forever. You wrote a book called “When Grit Is Not Enough.” There’s this, like, I think fundamentally, there’s this grind culture in entrepreneurship, and that gets you moving, but if you don’t build systems and scale, at some point, you don’t have a business. First of all, you just have an expensive job or a time-consuming job that might pay you very well. If people are reading your book, what principles in there do you think first-time founders underestimate the most?

Dean Guida: Cool. Underestimate. It takes time to build process and systems. I don’t know. It’s easier and faster today with AI, but also people are part of that process. So, when that happens, you got to get people into a rhythm, train them, observe them, make sure it’s flown, and then move on to the next thing. So, I think I don’t know if people underestimate that, but that’s certainly not a given. Getting good at doing things is hard, so like even we underestimated like OKRs. We love OKRs, and it’s a very simple framework. Objective and key result was invented in the 70s by Andy Grove, CEO of Intel, kind of like really popularized by John Doerr, the famous venture capitalist, so like. Google, Microsoft, DoorDash, a lot of people use them.

I really love it, because if I just say to you, “Increase margin by 20%,” you’re like, “Okay, there’s lots we can do with that.” But if we collaborate as a team, which is also important in creating OKRs, and you say, “Oh, okay, negotiate with vendors, get 5% there, train our people to be more effective, we can get 5% there,” so we’re like prioritizing three to five things that we’re doing to achieve the objective. That’s why I really like OKRs, but like I said, the framework’s really simple, but it’s so hard to do it. We have smart people, and I kind of feel like it took us 12 to 16 months to get really good at it. And I’m a Vistage speaker, which is like a speaker to there’s like 45,000 mid-market CEOs in there, and really smart CEOs, really great businesses.

And we go through the OKR exercise, and everyone thinks it’s easy, and then we do it, like I make people do it with them, and it’s hard, like it’s hard. So, there are frameworks and processes that are easy to understand but hard to implement. I think that’s another thing. And another part thing I talk about in the book is a scientific method of driving business outcomes. Very easy concept, like look at the data, trying to identify signals of why you’re not achieving something, create hypotheses with the team how you can do an experiment to improve that outcome. Intentionally say what you want to learn and measure. Go do it. It worked. You fixed it. It worked partially. You learned. It didn’t work. You learned, and you keep iterating.

Again, simple concept. The scientific method has been around forever, but it’s still hard to do, and then being data-driven too is hard to do, because data always tells you what’s happening, not why, and that’s the hardest part. Like, data tells you what’s happening, and then you have to like work with the team. If you ask, keep asking why, why, why, why, maybe you’ll drive your team a little crazy, but you’ll really make them think, because you start running out of answers, but it makes you think, think, think. And so, why is conversion so low? Why aren’t people sticking? Why, why, why? And then people start off, unfortunately, with just like ideas, but not why.

And so, that’s another really good process, but… So, really good business concepts are easy to understand, but hard in practice, and so that’s where that repetition and working through it, and involving the team, that’s so important. Because when you involve the team in solving problems and executing, you all learn together, and you get better ideas, and you get alignment and shared execution. So, a lot of people that are A-players, they’re like, “I could just do it faster myself,” but you got to bring people along. And today, equations change a little bit, like we’re really focused on being a great AI go-to-market company, and how we execute, and so things are changing a little bit. We’re like, okay, an A-plus player usually gets to work, done work of 30 people, right?

And then sometimes they’re impatient with others to get worked on. Now, because of AI, they can get 100x work, and they actually don’t need as many people. So, the equation is changing a little bit, but still, the management principle of the team comes up with really good ideas, collaborate, you get alignment, it’s better at executing, and funner, and are more fun. I don’t know if that’s a real word, but.

Brad Weimert: What you gave me, like five things or 10 that are from the book, that I think are practical takeaways, but I want to double click on the people thing. But I also want to highlight a principle that you just said that I think’s a really, really relevant one. First, that is that simple things are often very difficult to execute, and I think refining thinking, i.e., defining the OKR that you’re coming after, is it reminds me of a Mark Twain quote, which I always mess up, but it’s something like, “I was going to write you a short note, but I didn’t have time, so here’s a long letter instead.”

Dean Guida: Exactly. Exactly.

Brad Weimert: To drill down and actually have that clarity of thought is really difficult, and it takes a lot of time, but that is the planning that allows you to run fast later.

Dean Guida: Yeah.

Brad Weimert: The other thing you said is you have a lot of power with AI to like create the plan or help with the thinking, but you still need the people to do it. And so, it’s not good enough to write the SOP. You then need to manage the SOP for some period of time until it’s actually in practice and running well. And sometimes you didn’t write the SOP the right way in the first place. You need to clean it up. Sometimes it just takes time for the team to latch on to it and do it well, right? But if you let it go and you just try to put an SOP on and move to the next thing, you’re going to have to go back and fix it later.

Dean Guida: Yeah, that’s exactly right. You need to do what you just said, because there are issues, and like, your good players will say, “Hey, the SOP is wrong. Here’s how to improve it,” and then they improve it, and they share with others. Others, not everyone’s an A player. Others will be just like, “This is a stupid process. I’m doing it. I’m doing it.” And then you check in because you’re not getting results a month later, and like, “Why didn’t you speak up?” Yeah. See, I’m a bit like micromanagement has this bad connotation. It’s not bad, actually. If you consciously use it, not by default use it, but like, whether you have onboarding a new executive or a new person, you should micromanage them. And you want to know why?

Because in 30 days, you will know 100% their capability and their work style and their initiative and motivation. You really will, and so it’s kind of worth it. Well, one, you’re micromanaging because you’re teaching them and you’re helping them, and it’s worth that time. And then you could just zoom out and leave them alone, or maybe you made the wrong hire, and the best thing to do is fire early. But like, so micromanagement is a tool, not a negative thing, like I believe in it, whenever you’re onboarding a new person. And then if someone’s challenged, there’s nothing wrong with you getting in there and getting on the front lines and helping, and then you can zoom back out.

Now, if you do it all the time. Of course, there’s different skilled people, so like, you kind of have realistic expectations for different people in different roles and what you’re paying them. But no matter what, if you’re doing it all the time, there’s a problem with your management, and there’s also a problem with your people not owning what they have to do.

Brad Weimert: Yeah, I agree with that vehemently. My operations guy likes to say, “I’m in heated agreement with you right now.” It has a terrible connotation. Of course, employees that aren’t doing the process and/or aren’t doing well get angry when somebody is micromanaging, but I think that also very much comes to how you do it and how you approach it. But the fact of the matter is you need to have alignment to get the activities done the way that they should be done to drive the right outcomes. And sometimes it’s the activities that aren’t done right, sometimes it’s the wrong activities, and you sometimes need to play with that to figure out how to get the outcomes.

Dean Guida: Yeah.

Brad Weimert: But I’m a huge proponent of that personally. People can be a very challenging part of the entrepreneurial journey when they’re building a system, and obviously, everybody has different skill sets. You have a pretty distributed workforce, though, don’t you?

Dean Guida: Yeah, we’re global. We’re in like eight countries, and we’re all remote, except for two countries. We still have like 60 people coming in one office, maybe like 80 coming into the other, but no, we’re all remote now since COVID. And we built this beautiful building in New Jersey, 75,000 square foot beautiful building that we got 14 years of use out of, and I mean we’re renting it out now, but it’s kind of a shame, but we’re all loving working from home.

Brad Weimert: How many people are on the team?

Dean Guida: We’re a little over 250 people.

Brad Weimert: How do you align a global workforce around a large goal?

Dean Guida: Well, repetition in message, repetition, repetition, but like for us, it starts with our strategic plan, then our action plans. And our action annual plan that we do, which supports we talked earlier, our three-year, where we want to build capability over three years, where we’re maybe shifting how we go to market, maybe we have product shifts, and what we’re building, but it talks about that, so people get how we’re shifting or what we want to do new or build. I mean, that’s what the strategic plan does for us. And then annually, we actually create a whole slide deck of OKRs, and we kind of like cascade them down.

So, for example, like objective, deliver 5 million more in revenue, and then the three key actions are account-based selling, digital marketing, inside sales, whatever. And then those key results then can be an objective of and then cascade down. So, we kind of do it at a high level, and then we push the cascade down to the teams. And the things that are not negotiable, like we can’t change our revenue targets, but we could change pretty much everything else underneath. And we typically don’t change like major product direction, unless it’s a full process to kind of go through to that. But then, like once you start executing, things just don’t work, and that’s where that whole experimentation and OKR thing comes in, and data-driven, but then you can keep changing to improve it.

But a global organization, so it starts with that, and then it’s just repetition. Like, monthly I talk in front of the whole company, and I always talk about our vision and our core objectives and sharing our wins. And so, like, as a leader, it’s really important to share stories, purposely good stories, which people love and remember that highlights your vision, highlights your objectives, highlights your wins, make people feel good. And so, telling stories as a leader is really important. It’s very memorable for people, and it’s purposeful, so you’re highlighting your brand, your capability, your vision. Like, we always talk about simplicity and beauty in the world, one app at a time. And so, like you talked about before, Mark Twain, it’s hard to make things simple. It’s so hard.

And so, our customers come back to us and say, “Yeah, I’m using your UI components, and like my app’s so beautiful, I’m winning deals. And you guys won the deal over your competitors, because Reveal BI was, it was beautiful.” We’re like, “Yeah,” and it’s true, but you repeat those stories. And then we have OKR, so it’s really grounded, not in fluffy conversations, you know, “How’s leads going?” No, no, no, it’s not just leads for lead’s sake. Are they converting to a meeting, converting to a pipe, converting to a forecast? And so, like, we’re kind of like it takes a while, but we’re data-driven, which you have to be careful of, too, by the way. You can have too many metrics.

But we’re kind of always talking about things like I was reviewing our monthly GTM, like so each product line has a monthly GTM, and it’s like filled with OKRs, like here’s what’s going on with sales, here’s what’s going on with marketing, and here’s what our sales are, but here’s going on marketing, here’s going on with sales, here’s what’s going on with SEO. So, it’s really that alignment and the process of planning, which I’m a believer in lightweight planning, but the process of planning also globally aligns people on execution, that’s the value of it. And then you go and execute. I prefer most of our time spent on execution, but there’s a piece of planning in there.

And I talk about those things in my book, like OKR, scientific method, strategic plan, annual plan, go-to-market plan. And then the thing that keeps everyone informed and together is the rhythm of the business. So, the rhythm of business sounds fancy, maybe to you, or maybe not, but it’s like, okay, what’s your daily, weekly, quarterly? What’s your cadence of talking about problems and goals and formulation to how to fix your go-to market or fix whatever?

So, all those pieces, really, the book prize, and everything I learned over when I wrote it, like two or three years ago, everything I learned over 35 years through reading, learning from others, and then the thing is, it’s all from us doing what’s very operationally focused. And I love to read, and a lot of people love to learn. I do too, but I hate it when I read a book, and they give me three great concepts, but then I’ve never been able to just stop reading. I have to read the last 200 pages. It’s like a real big problem I have. I think a lot of people have that problem. But like, I don’t need to hear 80 stories. I’m exaggerating, like, give me two or three examples. I got it. And so, I tried to do that in the book, give a lot of value, give some examples, but don’t overdo it.

Brad Weimert: I love that. So, do a good job of your planning, break it down into OKRs, which are the objective you want, then the key results that lead to the OKR. If you want a different framework, the EOS framework is you have rocks, and then you have milestones that lead to the rocks, and you have quarterly goals around that, whatever it is. Big goal broken down to little goals and then reiterate that on a very consistent basis in a consistent cadence, so you have a rhythm of the business that allows you to reiterate that naturally, where people come to expect it, and it creates sort of an ingrained habit of the team and the culture.

Dean Guida: Yeah, and be careful of having meetings around just informing, like try and stop that, and it keeps popping up. See, here’s the other thing: if you run a business long enough, you do really well, but over time, when you stop doing things well, you got to watch for that. So, like, there’s nothing worse than sending a PowerPoint deck out. It’s 30 slides, and the meeting’s about reviewing the 30 slides. Horrible. Send it out two days in advance, everyone needs to read it, and then you come with questions and problem-solving. That’s an effective meeting. And we talked about boards earlier, and I had to, like, train my board to not do that. And it took a lot of me saying, “You guys got to read this. Did you read it? You got to read it.”

And then some people would not answer, then you call them out. It’s like when people aren’t speaking in a meeting, you need to call them out. Why? Because you need to know what they’re thinking. They’re either aligned, not aligned, or negatively aligned, or something. So, those are like just good tactical techniques. Read everything before, don’t have informed meetings, a waste of time, except for like the five-minute stand-up. I totally believe in all that kind of stuff, but.

Brad Weimert: Yeah, that’s a rhythm thing.

Dean Guida: Yeah, we do that a lot digitally. But anyways, those are some really good tactics. And then over time, too, it’s weird how all of a sudden you still start to have too many meanings, and you have to look at that and then readjust. It’s a living organism, a company.

Brad Weimert: I love that. So, being methodical about making sure that meetings are valuable to all people that are there, and you get a couple of tactics to ensure that that’s the case, which is prep for the meeting, and if you have something you need to cover in the meeting, have everybody prep ahead of time and come with questions for discussion if they need it. I would invite my team in those situations to say, “After you’ve read this, if we don’t need the meeting, we can cancel it.” Right?

Dean Guida: Yeah.

Brad Weimert: The placeholder is on the calendar because I want to make sure we have the space for it on a routine basis, but if we don’t need it at some point in time, let’s cancel it.

Dean Guida: Yeah, good.

Brad Weimert: I have a close friend, Cameron Herold, who’s actually been on the show a number of times, and he wrote a book called Meetings Suck, and he has several frameworks for different types of meetings, which is very helpful if you’re doing a creative meeting versus an update meeting, or whatever, but one of the premise, the fundamentals of it is what you just said, which is you should never have a meeting that doesn’t have a clear agenda.

Dean Guida: Yeah, no doubt.

Brad Weimert: If you do, get it off the books.

Dean Guida: Yeah, I agree. And then here’s like another tactical tip that I learned through the Vistage group that I was part of, for so long. They start every meeting with, like, this quick check-in, professionally and personally. I got to tell you, that personal part bonds the team. Like, you can share whatever you want. It doesn’t matter. But when you have your team, like, in the beginning, just like I do it every… Our exec team meets every Tuesday for two hours, and we do it right at the beginning, and it gels, it creates trust and bonds a team. So, like, “Oh yeah, this weekend I did this with my dog, or whatever, I cooked this, or I watched, did that.” It’s just sharing personal bonds the team.

Brad Weimert: Yeah, I love that. We do that as an executive team, and I just actually made a note, because we don’t do it for other teams, and I think you’re totally right. I think for operators, it seems like some fluffy bullsh*t.

Dean Guida: It’s real.

Brad Weimert: Yeah. From a culture perspective, there’s no question,

Dean Guida: And it’s real per execution. Like, if you’re an operator, it’s for execution too.

Brad Weimert: Yeah, I think you’re right. I think it’s very easy to think that the fluffy stuff doesn’t translate to the actual rubber on the road, and I think that’s foolish. People are, I think, one of the most common reasons to leave jobs is they don’t like their work environment, they don’t like their manager, or the people that they’re working with, right? And I think you can navigate through quite a bit of that if you encourage the personal connection and communication.

Dean Guida: Yeah, you get to know people, and then, like, it makes you want to help them. It makes you be more understanding of problems, and it just gels a team. Yeah.

Brad Weimert: Well, to that end, do you have any frameworks for having difficult conversations when performance slips in a team?

Dean Guida: Yeah, I talked about it at the beginning of our interview. I went to the Center for Creative Leadership, which was like scary, spooky how advanced psychology is like they know everything about us. And so, like I had to take all these tests and got interviewed, and so they knew everything, how I react. They knew how to like pull out my good and bad, and they placed me with people in different situations and high-pressure real experiential learning to pull it out. Like, there’s nothing like feedback, but there’s nothing like forcing you into a bad situation to pull out your bad traits, and then you’re like, you can’t deny it. You just experienced it. So, at the end of this week, there was like some very strong A-plus players there that were crying.

I mean, it was that. It broke you down like that, but I learned this framework there: situation, behavior, impact, which is really powerful. Like, you got to have the hard conversations for sure, and you need to do it like one-on-one, privately. Sometimes you have to have a second person there because of HR reasons, but most of the time you don’t. Really just you’re really releasing somebody having that HR person there, but situation, behavior, impact is like, “Okay, Brad, we were in that meeting, and like, you kept cutting everyone off, so that’s the situation, that’s your behavior. And the impact was everyone stopped talking, and the impact was like, we stopped collaborating.” And like, “Oh, I wasn’t doing that.” And I’m like, “Okay, you don’t have to debate it, but like, you gave that feedback.”

And so, it’s kind of a powerful situation, behavior impact, so it makes people, “Oh, you interrupt too many people in meetings.” Well, if you give it soon enough, so like everyone wants examples, so that’s like a powerful framework. And giving feedback is important. I mean, normally, people don’t want to do a bad job, right? So, people either thank you for the feedback, or people will be whatever their personality is, they’ll be resisting the feedback. But even people who are resisting the feedback in the meeting, then you can see behavior change, because, okay, fine, I don’t care if you admit it or not. We’re all just trying to win. But the problem is when you just let things happen, and then everyone observes you.

Your A players observe you as the manager, and if you keep putting up with bad behavior, they’re going to leave, and they’re not going to respect you as a manager. So, it has like a really bad team effect.

Brad Weimert: Well, so to that end, yeah, I love that. Any framework, I love frameworks in general, like, dude, the thing that allows you to sort of follow a process to get somewhere. I think, like, I have a deep-seated belief that entrepreneurs really all want somebody to just tell them what to do. The problem is we have a hard time with authority, and so we have a hard time respecting or listening to the person that, or believing the person that’s telling us what to do. We’re always unique in some way in our heads, but I like frameworks for that reason. So, finish the sentence. The easiest way to wreck a high-performance culture is…

Dean Guida: Putting up with bad behavior. It’s debilitating, and resources are precious.

Brad Weimert: I love that. Well, a couple of quick ones for you. What is a belief you’ve changed about scaling a business in the last 10 years?

Dean Guida: Belief I’ve changed.

Brad Weimert: Or from when you started. How did you look at scaling when you were starting the business in the beginning, versus how you look at it today?

Dean Guida: I mean, a lot changed since then, so I’m glad you opened it up more. I mean, I was probably like most people, like I work 24/7. I was like able to do so much work fast. I hired people like me. I had no patience. I learned to have some patience and take time to get to know people. I was just so… I learned so many processes, but I guess, so one thing is, you got to take time to build a culture and build a team and be thoughtful about the culture you want, because what all culture is how everyone behaves with each other, how you guys get work done together. And so, you want to be very thoughtful about that, and it can be yours and unique, but you’re going to attract and keep people that like that.

If you have a good culture, you’re going to have retention, good retention, and attract good people, and good people are going to stay for a really long time, even though they can make way more money at some big company, but they know the consequences of making way more money working at some big company where they hate their job. And so, like, we have some amazing talent that can make so much more money elsewhere, but they stay because they like the products they’re working on, they like the people they’re working on, and they’re mature enough to know that way more money doesn’t mean happy life. And so, it really matters, and it only takes a few bad moves to go work at some big logo and be a cog on the wheel, and people don’t care as much, and people like you won’t like it.

And if you do like it, then great. You shouldn’t work here, where we are. Like, we need to be elite, where we can’t afford extra, and we need to get stuff done. And yeah, we want to have fun doing it, for sure, because life’s too short, and work takes so much time, so you want to have fun. But, yeah, so I don’t know if I answered your question.

Brad Weimert: That’s great.

Dean Guida: Did I answer your question?

Brad Weimert: You did, and you’re full of great frameworks, thought, story, so I love it. Where can people find out more about your work, the book, Slingshot, wherever you want to drive them?

Dean Guida: Yeah, DeanGuida.com is like my personal website. That’s where you can find out about my book and then some of the articles I write, like one article every couple of months for Entrepreneur.com. But you can go to Infragistics.com. That’s our kind of umbrella with all our products, but then there’s SlingshotApp.io, there’s RevealBI.io, and there’s AppBuilder.dev. So, we have like different branded products, and that’s like how you can learn about our products, but those are places people can go to learn more.

Brad Weimert: Dean, I love it. We’ll put all that in the show notes, and let’s get some time to hang sometime soon.

Dean Guida: Yeah, that sounds great. Thank you.

Brad Weimert: Yeah. Thank you, man.