226: How He Scaled to $30M ARR (While Living a Life of Extreme Adventure) with Jonathan Ronzio

I’m sitting down with Jonathan Ronzio, who scaled Trainual from an idea to $30M ARR—while building a company known for its culture and still finding time to climb mountains, run marathons, and live a full life outside of work.

What stood out to me in this conversation is how intentional he’s been about building systems—not just in the business, but in his life. We talk about why most founders document the wrong things early, how structure actually creates freedom, and how AI is completely reshaping how companies build, sell, and operate.

We also get into how he thinks about balance versus alignment, what changes (and what doesn’t) after raising capital, and why the most defining moments in business are usually the ones you never planned for.

If you’re trying to scale without becoming consumed by your business, there’s a lot here worth paying attention to.

Mic Drop Moments

• “The earliest thing that you could document that’s going to be the most wildly effective and have the highest ROI for your company is going to be stuff like your mission, your vision, your founding story, your core values, the stuff that really sets the bar for what everybody’s experience is when they first interact with your company, when they come on as a new employee.” – Jonathan Ronzio

• “Anything that you are iterating on, on a frequent basis, is not worth spending the time to document.” – Jonathan Ronzio

• “It’s still cheaper to buy powerful SaaS products that fit into their stack than it is to stand up the infrastructure of building and managing themselves.” – Jonathan Ronzio

• “We have a high bar for people coming in. I mean, we’ve let people go that are absolutely stellar at their job, but that just are not core values fit and don’t collaborate and communicate and have too much ego or too much entitlement, like that’s just culture cancer and that’s got to go despite how good they are.” – Jonathan Ronzio

• “No decision is difficult for me because I’ve made life or death decisions in the backcountry.” – Jonathan Ronzio

• “When you start your business, the most memorable part of your entire business journey is not going to be something you can plan for. It’s going to be when a disaster strikes or when something in the market changes and you are forced to adapt and you’re forced to think inside of yourself and figure out and go deep and how resourceful and resilient and creative can I be to get through this. And that’s what’s going to make the biggest impact for you in your life and in your business.” – Jonathan Ronzio

• 00:00 Introduction
• 00:49 Summiting Aconcagua vs Closing a Series B
• 02:32 What Is Trainual and Why It Exists
• 03:40 The #1 Thing SaaS Founders Document Too Late
• 05:02 When to Create Company Core Values?
• 06:51 Why Structure Actually Creates Freedom
• 10:17 Which Processes Deserve SOPs?
• 11:40 How AI Transformed Trainual’s Product Roadmap
• 15:31 Will AI Kill SaaS? His Honest Take
• 20:45 Figure Out How to Disrupt Your Business
• 21:40 Agentic AI and the New Outbound Playbook
• 24:24 The Exact AI Tech Stack His Team Uses
• 28:08 Data Security in the Age of AI
• 32:37 $400K in Credit Card Debt for FB Ads
• 35:52 Balance vs. Alignment
• 38:24 Why Daymond John Joined the Cap Table
• 41:49 Cultural Practices That Actually Work
• 44:39 Project Management & Communication Tools
• 49:10 How to Define Culture at Scale
• 50:17 Mountaineering Lessons That Made Him a Better Leader
• 57:12 Living an Adventurous Life
• 01:05:19 Obsessive Compulsive Creative Disorder
• 01:08:11 Advice for Founders Torn Between Focus and Exploration

Brad Weimert: You scaled Trainual from an idea to 30 million in ARR, while getting accolades for being one of the best places to work consistently. You have thousands of people using it. You have also done some crazy high-altitude mountaineering. You shot an award-winning documentary while doing it, and you’re a pretty good snowboarder, too. Jonathan Ronzio, welcome to the show.

Jonathan Ronzio: Thanks a lot, Brad. Great to be here. Excited to wrap with you for a little while.

Brad Weimert: Yeah, for sure. So, alright, summiting Aconcagua, or closing your Series B, what produced more excitement for you and why?

Jonathan Ronzio: Closing the Series B because, so I actually, about 1,200 feet shy of the summit of Aconcagua, fell to my knees with symptoms of high altitude pulmonary edema. And so, my two buddies made it to the top, but I did not get there. And that ended up being like the worst 18 hours of my life, trying to get down to lower altitude and dealing with what was going on inside of me. So, yeah, hell of a time on that mountain, but closing the Series B was better. It was a wild day, actually, in New York. We were out there shooting. This was like June of 2021. We were shooting a new commercial with Daymond John from Shark Tank and with Montell Jordan from “This Is How We Do It.”

And I had just wrote a new like a remix to This Is How We Do it with Montell for a Trainual song. And you could see behind me, obviously, music is a big part of my life and that’s made its way into a lot of our marketing campaigns, but we’re like in the city, in Brooklyn, just finished wrapping this commercial with Montell and Daymond’s and went to dinner and then got back to the hotel and literally saw the wires hit for closing the Series B. And that same day, that morning, my wife told me that she was pregnant with our first son. So, it was just an unbelievable day.

Brad Weimert: Crazy. Well, not that anything could beat being violently ill at the top of a mountain, having to struggle to get down for 18 hours, but it does sound more exciting on the business and life front there. Alright. So, you founded Trainual. In one sentence, describe Trainual to a bartender at Base Camp.

Jonathan Ronzio: Yeah. Trainual is your company’s operational brain. It is the thing that knows what everybody does, what is the best way to do things, how you’ve done it versus how you need to do it, where the processes are breaking. It’s the centralized system that runs all of your onboarding and training, and who does what and how, and constantly grows in its knowledge with your company, so that when somebody key leaves, everything that they’ve done for you and everything they know doesn’t walk out the door with them. It’s that.

Brad Weimert: Love it. That was way more than one sentence, but I love it.

Jonathan Ronzio: It was a run-on sentence. I like commas. Dude, we’re at a bar in base camp, you said. I’m going to keep talking.

Brad Weimert: Well, I’m excited to dig into how it’s evolved over time. But before we do, fundamentally, you started with documentation, documentation, documentation. What is one thing that most SaaS founders forget to document early, and it’s way too late by the time they do?

Jonathan Ronzio: Honestly, I’m going to answer this from a culture standpoint. Most people don’t start like, they think in terms of like I need to document our Facebook ad process, or I need to document our payroll process, or something like that. Like, they’re trying to think about, like, operational intricacies of the company. And the earliest thing that you could document that’s going to be the most wildly effective and have the most like long-term ROI for your company is going to be stuff like your mission, your vision, your founding story, your core values, the stuff that really sets the bar for what everybody’s experience is when they first interact with your company, when they come on as a new employee.

Like, you want that so dialed in that everybody who starts, whether it’s four years out or four months out, or four weeks out from when you actually started the company feels like they’ve been there since the beginning and they’re on that rocket ship with you and totally aligned and mission critical to what’s happening because they understand the intricacies of what you value as an organization.

Brad Weimert: Dude, that’s such an interesting topic because I feel like entrepreneurs have very different approaches to core values, and I leaned very, very heavily on them. And I’ve sort of learned of the value of core values as I’ve gotten older as an entrepreneur and had more experience, and they’re more and more important to me as time goes on. Some people believe that you should create your values with your team, some people believe that your values emerge through the existence, and some people believe that you should create them and then push everything through that lens. Do you think that you need to create your core values before anything else when you start the company? Is that where you’re going with that? At what point do you need to put them in place?

Jonathan Ronzio: Yeah, I believe you create them right from the start, and you set the tone of the company that you want to build, but that doesn’t mean that they’re static. I think that they evolve as the company evolves and as the team grows. And maybe you’re the person that right at the beginning, says like, “These are the five things that I value in a company and that I want to see represented in the next few key crucial hires that I bring on board.” But then a little down the line, you’ve got 50 people and you go on an executive offsite and you’ve got your six people on your C-suite team or whatever, and together, you might analyze like how we’ve changed as a company and does this core value still fit our day-to-day practices and processes, and our culture, or do we need to iterate on this? I think that culture is ever evolving.

Brad Weimert: Yeah, I love that. I want to dive deeper into culture, a little bit later. But I love the frame of doing it as a procedural element and making sure that it’s part of the SOP framework. And I think a lot of people lose that and don’t actually, as a result, anything you don’t systemize and track doesn’t get the attention that it needs, and it sort of slips through the cracks.

Jonathan Ronzio: Right. Yeah.

Brad Weimert: So, for such a dynamic human, do you get tired talking about SOPs? It’s sort of a boring subject matter.

Jonathan Ronzio: Yeah. You know what’s funny? I’m not the SOP guy, but I am representative of the value of SOPs in terms of what they do to give you freedom, in terms of removing the bottlenecks of your business to unlock your genius zone that you need to live in. So, Trainual started with my brother and I. It was actually built as a beta product inside of his operational consulting firm in the earlier days, when I still had a venture media company. But he and I have had tons of businesses together, collaborated our whole lives. And when he was thinking about spinning this out as a separate software product and closing down the consulting, he tagged me in to like figure out, can I help build this brand and build all the marketing systems around getting it started?

I didn’t necessarily think that I would be here eight years later, still involved with this company. I was like, “Cool, I’m going to come hang out in Arizona and get this off the ground with you and then bounce back to whatever mountain I have next to climb.” But then it just got to be so fun working together again. And so, Chris, my brother, has always been more of the process mind, the one where like the vision of the SOP product kind of came from. But through our previous company together, we had both dialed in this muscle around systemization, and brand style consistency, and hiring and training. Like, we had a video company that we did amateur sporting events and all across the country, we’d have different figure skating events or cheer events, and we couldn’t be at everything.

And so, we had to figure out how to train up a network of video operators and contractors and sales professionals that could like, on a dime, be there and run the event as if we were there because we had everything so dialed in. So, we both had that in us, but Chris was definitely more of the ops process kind of mind. And I was more of the creative storytelling, media marketing person. And so, yeah, I wouldn’t say I talk about SOPs all the time, but I talk about what SOPs can do for your life.

Brad Weimert: Dude, I can’t tell you how much I love that. I think that one of the most common things that I see with entrepreneurs, or the common entrepreneur archetype, I should say, is this rebellion against structure because they’re chasing the new thing, and they want something exciting and different, and they feel like they’re not authentic if they have this rigid framework. And I very, very much believe that it’s within structure that you find freedom, and you, in no uncertain terms, said that, which I think is beautiful.

Jonathan Ronzio: No, I agree with that. I used to, like, prior to Trainual, I did a bunch of speaking in the adventure space, and there was a concept I used to teach called unplanning, and it was around this idea of like not having a schedule or an itinerary and just booking a ticket and landing and figuring it out. And I just lived in that exploratory mindset. But now more than a decade later, I’ve got Jesse Itzler’s big ass calendar on my wall, and my entire year is mapped out, and I know everything that’s happening and like dialed in on a weekly basis, on a daily time blocking basis. And now I’m more planned than I’ve ever been, but it’s created more opportunity to do more in my life than I ever have.

Brad Weimert: I love that. Well, in the world of documentation and creating roadmap, structure framework, SOPs, you can lean in the direction of getting too granular. How do you decide which processes deserve a full procedure SOP versus like a quick Loom is good enough?

Jonathan Ronzio: Yeah. And anything that you are iterating on, on a frequent basis, is not worth spending the time to document. If you’re still figuring out a channel, if you’re still dialing in a certain process, if you’re testing how you interact with customers, that’s not worth documenting. But if you have figured out that like this is the thing that we do, we do it consistently, it’s been that way for the last three, six months, and now we need more people to learn how to do it, and we need to remove the vulnerability of somebody going on vacation or leaving the company or whatever, and somebody else has to pick that up immediately or we’re hiring 10 other people to do the same role.

Like, if you have things dialed in that are done on a consistent basis, document that, but I’m not spending any time documenting what we’re doing with AI inside of our go-to-market architecture right now, because every single week it’s a different tool to test.

Brad Weimert: Yeah, I love that. I think that’s a good guidance. And you kind of, well, let’s talk about AI. So, it’s April of 2026, and as you mentioned, that date stamp is tremendously relevant because the pace of change is exciting, insane, anxiety-producing for some, and it is just rapid iteration, nonstop if you’re leaning in. How has AI changed Trainual from a product roadmap perspective, customer adoption, or even kind of internal workflows in the company?

Jonathan Ronzio: Tremendously, in every aspect of what you just mentioned. I mean, as far as product roadmap, we can talk about that. Like, we first started messing around with the OpenAI API as soon as it was available, like months after ChatGPT launched, and started like one of the biggest blockers to people documenting their SOPs is actually spending the time to document it. They’re like, “What do I write? I don’t know how to write,” right? So, like, we just put that in the product immediately was like, cool, and let’s just give it some prompts and some bullet points, or like bring what you already have from other places, and it’ll build out your perfect training for you or make your SOPs.

So, that’s existed for a long time, but now where we’re driving is more proactive AI insights and like not waiting for you to ask an agent anything, but actually like the next time you log into the system, because it’s connected to these different systems of work that you already use to integrate it in certain meaningful ways on top of the value props of our training and operations and performance, the things that we do inside the platform. Now, we’re building proactive interactions on top of that data structure that the AI essentially becomes your continuous improvement manager, your learning and development manager, your hiring and training manager, and it’s helping you uncover things that are happening around the business that you might not be able to see otherwise.

And becoming like this brain that helps level up all managers or this faux manager that’s helping give every employee consistent experience. So, it’s absolutely impacted the roadmap in a huge way that we’re like centralizing so much around the AI inside of Trainual and how the interactions with the AI become more powerful. From a standpoint of what we’re doing with our, like, internal processes, I mean, things that would take two months or four months in terms of a product and engineering sprint in the past are now cut to two days or two weeks, and we’re not spending time with product managers that need a month to go talk to customers and put together a one-pager and validate an idea before it goes to design, and then have a static clickable basic wire frame that then gets vetted to customers again.

And before it even goes to the tickets to engineering to start building, it’s like we’re in real time product and design are just building prototypes for the roadmap, and like the next day, the engineering is pulling the react code base out of that, throwing it into Claude or whatever else to like run QA against how it merges into our own system. And things are pushed to production in no time. So, it’s accelerated so much, and not even to mention how things are happening in terms of go-to-market and the optimization of ad platforms and the AI SDRs, and just in general related to headcount. We’ve got 12 people on our marketing team, and at one point last year, we were like, “Oh, we’re probably going to need another product marketing manager.”

And now we’re like, “No, our product marketing manager just needs a product marketing agent that she then directs.” So, every single person, it’s not like we’re downsizing by any means. We haven’t laid anybody off, but we’re giving everybody the tools to multiply themselves without headcount.

Brad Weimert: Damn it, man. Now, I have like five different paths to go down with you around AI. So, let me start with this. Will AI kill SaaS?

Jonathan Ronzio: No, I don’t believe so. I think that SaaS will always fall into this buyer build bucket, right? And in the past build was exorbitantly expensive, and so most people went with the off-the-shelf buy. I think that there is going to be a compression of that consideration set, and for massive enterprise companies who have so many custom data and security and integration needs, and they’ve got the budget to actually have a team that might build their own custom tools, maybe that becomes the enterprise market on the top end. It might become a little less friendly to buying SaaS products. Similarly, I think, on the lowest end, any startup can jump into Claude code or Perplexity or Replit or Lovable, and they can build their own basic things that they need for their workflows without having to buy something.

And that’s cheaper and token credits than it is on a SaaS subscription. But I think in the middle of the market, like higher-end SMB, and mid-market to lower-end enterprise, for the foreseeable future, I don’t see a vulnerability because it’s still cheaper to buy powerful SaaS products that fit into their stack than it is to stand up the infrastructure of building and managing themselves.

Brad Weimert: Yeah, that’s an interesting take. The buy versus build conversation, if you’re involved in software, that is the conversation you have nonstop. And I think if you’re outside of software, you haven’t been forced to have that conversation, right? Because you didn’t have the capacity to build. But if you are building software nonstop, when you’re building, you’re presented with other services and other softwares that you can license or integrate or use. And you have to ask that question, do we pay for the service to integrate it or do we rebuild that entire function in the software? I guess the question is, as building gets easier and easier and easier, where do you finally get to the point where building is always the cost-effective proposition?

And we’re certainly not there now. Anybody that’s tried to build like actual software and with a no-code tool, we’re definitely not there now. But complex software, I should say, or that’s architecture heavy, permission heavy, et cetera, security heavy, takes time no matter what. I look at this arc over the course of the next three to five years and wonder how good it’s going to get. And if you are a prompt away or a day’s worth of prompts away from creating something super complex that is handled and built for you, and maybe even then, you aren’t going to be thoughtful enough in the creation to build the right thing. And so, maybe then it makes sense to pay somebody to solve those problems for you anyway. How do you think about that?

Jonathan Ronzio: I don’t think that you’re wrong, but I think that it’s mind-blowing how few people have even tested ChatGPT. I think if you’re inside of tech and you live in this world, everything feels like it’s happening on a tomorrow timeline. But Redbox is still an incredibly successful company with their vending machines of DVDs around the world. And like, how does that make sense with the amount of people that have Disney+ and Netflix, and HBO, and all these different streaming apps, right? So, I think that there is just a lag in the market that when you’re on the forefront of tech, you are a little oblivious to and have blinders on. And there are so many people that are just so non-technical that even their founding teams won’t even think about the capability of what they could build.

Brad Weimert: Yeah, I think you’re spot on there. I think you’re totally right. The way that I’ve been thinking about it is, because of what you just said, we have a longer period of time than people realize for adoption. And I don’t know what that period is, but I anticipate at some point we’ll get through that curve. And in my head, this is sort of the 2, 3, 5-year mark where people start to see, “Oh, I can do this.” And then we get to a point where a huge chunk of people are building on their own. Technology gets there, the learning curve gets there, the exposure curve gets there. And then what?

And so, I’m kind of, the way I’m thinking about building stuff internally is, build to enable people with the most badass sh*t possible right now while framing out a structure for five years from now, or three or seven or whatever it is to be a different product that works within the pipelines and the infrastructure that I think will probably exist where building becomes so democratized that almost every business is doing it.

Jonathan Ronzio: Yeah, 100%. I’m a big fan of kind of a skunkworks or a labs project in your business that is like its sole purpose is to put you out of business. It’s like figure out how to disrupt yourself. And like, that’s not where you push in all your chips right now, but it’s something that you need to think about. What is the five-year, 10-year roadmap? Like, you’ve read the book, The Infinite Game, like you have to be laser focused on, like, what is that infinite problem that we are solving and in what way we’re doing it well today with this version of who we are? And in what way does that need to change based on what I’m seeing in the landscape that maybe we don’t have the…

Maybe what we have today is more like the Titanic, and it can’t turn fast, but like, let’s have the speedboat over here and play with that in separate waters.

Brad Weimert: Yeah, I like that. Okay, so I want to talk about kind of your path of growth, but before we do, while we’re on AI, specifically, the go-to-market side of things, the sales, the customer acquisition, the distribution, how has that changed in the last six months since like agentic has popped up? And what I mean by that is AI that can go do things for you as opposed to just give you a response. And how do you see it changing in the next year?

Jonathan Ronzio: Yeah, as far as like how it’s doing things for you right now, like you no longer have to do all your manual prospecting, right? You just like set up your parameters and give it the ICP, and it’ll just go and build out all your lists, monitor the signals, pipe everything into your CRM, then have that trigger if you’ve built it. SDR that is always on your speed to lead is two seconds. It’s trained contextually on literally every signal that came in against that lead, whether it came from a lead magnet or a cold prospecting kind of an agent. It’s not only just sending the initial email and waiting for a positive reply. It’s trained with enough context to actually go back and forth and engage and get to a point of being interested in booking that demo.

From an advertising and content analytics standpoint, like you can set up an entire agent architecture around monitoring every single thing that happens on your organic social across every system. And if you’re using Manus, don’t use anything but Manus on ad accounts right now with Facebook. Otherwise, you get banned. But you can pipe all that data back into your content analytics dashboard, and then an agent can be using all of that to fuel creating new ad creative with Nano Banana and working with your creative team to… I’m leveraging all this, but I’m also against being a 100% AI in the creative. We still do a lot with our team. I still come from a background of really valuing authentic human storytelling in the adventure world and try to layer that into what we’re doing. But we’re letting AI speed up the process of creation.

Brad Weimert: Yeah, I love that. So, you gave a good tip, which was Manus with ads because Facebook bought it, and they’re going to smack you otherwise. Other than that, all of that sounds like a magic trick to probably 99% of entrepreneurs out there right now, which speaks directly to your commentary on when you’re in the tech space, you feel like it has to be done tomorrow, or you’re going to fall behind. The reality is most people are playing a little but have no idea what to do. And when they’re playing with AI, they’re having an email written for them, or they just figured out that they can execute something, getting added to their calendar, right? But they’re not actually deploying in the way that you’re talking about it. What tools are you currently using in April of ‘26 to execute that outbound motion?

Jonathan Ronzio: Yeah. So, for anybody that was listening to that and every word I said sounded like gibberish, the beautiful thing is you can just ask the AI to teach you how to do it. Like, literally, like open up Claude, or your model of choice, and just give it the problem you’re trying to solve, and say, and I am a total AI novice, I know nothing about setting up data stores and workflows with n8n, or like any of these things that I’m talking about. Like, you don’t have to know how to use it. You just ask the AI, and it’ll just like literally give you the play-by-play to do it. And you can ask it, “Hey, how do I set up Claude Cowork onto my computer so that you can actually do this for me?” Like, it will literally be your coach thing.

It’s so crazy that actually you can’t see it right now, but there is an amp, a Marshall amp over in the corner that I bought when I was in high school, and it blew at, or I thought it blew like at a show probably 20 years ago. And it had just been sitting collecting dust. And I opened up the back of it, and I took some pictures and sent it into ChatGPT and was like, “Hey, what do you see? How can I fix this?” And I knew nothing about fixing speakers or doing anything with electricity or welding or whatever, but like, not welding, soldering, but ChatGPT walked me through within a couple of hours how to fix that speaker. Unreal. So, back to your question of what are we using today, I mean, HubSpot’s at the center of our stack. That’s our kind of our source of truth for all of our customer data and lead data.

We are using things like Smartlead and Lemlist to test outbound campaigns. We are using Alta, which is a kind of an AI SDR platform that we’re piloting right now, which is our outbound reps are leveraging that for all of their list building autonomously and sending campaigns kind of on their behalf. It’s also what’s running that anybody that doesn’t have time to touch all the leads that are coming in because their demos are booked, all those leads would be sitting there otherwise. Now, we have campaigns that are running always on, like I was mentioning. We use n8n and Zapier as like the two different tools for workflow connection and building out all the infrastructure of how tools can act. What else? There’s a lot. I’m trying to think of things off the top of my head. Comet…

Brad Weimert: I mean, I think those are, yeah, what’s… Go ahead.

Jonathan Ronzio: No, I was just saying Cometly is something that helps us optimize all of our ad campaigns and like all of our marketing attribution. Navattic is another one. We’ve used Navattic in the past. It was a tool that like instead of having a video demo on your site, you could actually just create a clickable kind of interactive walkthrough of your product. And when we tried that, it increased our conversion rate for booking a demo by 430%, I think it was, of the interactive tour versus just watching a video. And so, now the iteration on that that we’re testing is they just rolled out agentic demos.

And so, instead of an interactive clickable tour, it’s a full-screen sandbox experience that you just talk to a voice agent that’s trained on the entire platform and knows all the workflows and memories and paths based on what you’re trying to sell. And basically, creates a self-serve selling model of an agent demo.

Brad Weimert: Sick. What’s that tool called?

Jonathan Ronzio: That’s Navattic.

Brad Weimert: Navattic. Love that. So, I’m scratching my own itch, but Easy Pay Direct is incredibly sensitive data, right? We’ve got all this personal information, we’ve got banking data, we’ve got customer data, we’ve got credit cards, et cetera, et cetera, et cetera. So, I have a very high on my list out of necessity is privacy and security. How do you think about exposure of your data or any of this stuff to one of the main models? Do you have any desire to run a model internally, like an open source model, or are you okay using the APIs of all the other platforms to process this stuff?

Jonathan Ronzio: So, we don’t touch, like we’re SOC 2 compliant, Type 2 as well, so we have to adhere to strict security guidelines in terms of the tool sets that we use. So, we can’t connect any vendor unless we look at their data room and verify all their privacy security policies. Our CTO is very stringent about that. So, that’s kind of our first line of defense. I’m not standing up any kind of open claw that touches anything that we do. And we also have certain rules about even if we’ve okayed a tool, inside of the stack for certain purposes, we have a different level of threshold for what can connect to certain key systems like Stripe or HubSpot.

So, we look at it on a case-by-case basis, but no, we’re not building anything. We’re using anything open source internally.

Brad Weimert: I was talking to my CTO yesterday, and he said, “How do you feel about sending this set of data?” And it was no incredibly private data, right? It wasn’t personal information, it wasn’t social security numbers, EINs, et cetera, et cetera. But how do you feel about using OpenAI’s enterprise API to process this particular request? Their privacy policy says that they don’t train on the data, don’t share the data, they’re compliant, et cetera, et cetera. And my response was, “Wait, OpenAI is a nonprofit, right?” And I was like, “The privacy policies can change.” So, I have concerns over those things in general, and I’m bringing it up because, A, it’s sort of funny, but, B, like, I don’t know, man. Clearly, the major companies of the world, up to this point, regardless of privacy policies, seem to be sharing data at different places that we’re unaware of.

Jonathan Ronzio: You’re not wrong. I think we’re in an interesting, it’s the wild west of all of that right now. I think that we can only be as cautious as we can be while still trying to be competitive, and you don’t want to be absolutely careless by any means, but you can take all the precautions necessary. But then Anthropic just talked about how, like they won’t even release the Mythos model for another 100 days because they need to lock this thing down because it like found 10,000 zero day vulnerabilities across 20-year-old systems that nobody on earth even knew were there and could like, basically, break the entire internet and release everybody’s data if they just let it go.

And so, things like that are being created, and who knows if a catastrophe in data security is going to happen at some point, regardless of the precautions that you take, not to say you shouldn’t take precautions.

Brad Weimert: Yeah. I think it’s a tough question. I like to get people’s stakes on it. Also, as far as Mythos goes, the Anthropic, how much of that do you think is a PR play to, I mean, this seems to be their playbook, right? Every model they release, they talk about this catastrophe because their model’s so dope that it’s going to break the internet. Do you think that this is PR? Do you think there’s a real threat? Is it a balance between?

Jonathan Ronzio: I think it’s a balance between. I think that is their playbook, and they’ve proven to do that every time. They do some sort of like fear hype about the capabilities because it grabs attention, and that works. But the fact that they’re not just sitting on it themselves, and then like the fact that they did put together like a coalition of 40 of the top companies in the world to actually analyze this, tells me that there’s something real.

Brad Weimert: Yeah, I think that’s probably fair. Okay. We’ll get back to AI probably a thousand times because it’s relevant in every area of business. But let’s back out to sort of the growth of Trainual, period. So, you start the company, and you’ve raised money a couple of times through the process. Notable rounds, I think 6.75 million for the Series A, and then 20 plus million for the Series B. Is that accurate?

Jonathan Ronzio: Yep.

Brad Weimert: So, before you raised, how did the constraints of bootstrapping shape your growth playbook, and how did it change once the first round of capital hit?

Jonathan Ronzio: To be honest, we didn’t operate differently. We took more bets in different new channels. Maybe once we had enough funding, we scaled the team a little bit faster, the roadmap a little bit faster. But how we operated the company didn’t change a lot. Like, even before the Series A, it probably like April or May of 2018, we were a few months into the business. That’s when we started like messing around with Facebook ads and testing scale that way. And when we saw that things were working like just insane results, we just started doubling down, and kudos to my brother. He took a flyer on this, but he ended up going like almost $400,000 in credit card debt just on Facebook ads.

And so, yeah, so we just kept pushing because the CAC worked and the unit economics seemed right, and we wanted to push growth fast enough to gain market share and have a shot at a raise. So, it’s not like we waited for the money to take those big bets. We were spending a lot of money that we didn’t have in the early days.

Brad Weimert: Yeah, that’s the bootstrap game, I suppose.

Jonathan Ronzio: Yeah. No, it got fun though. It changed the scale of what we could go after. I mentioned the whole like Montell-Daymond kind of thing. We wouldn’t have been able to do that in the first year to reach out and collaborate with those kinds of people. But I always had Super Bowl-worthy ideas that I wanted to pursue. And it got more possible to do kind of wild ad campaigns and bigger experiences.

Brad Weimert: What KPI dashboards open on your phone right now? What are you looking at on a daily basis?

Jonathan Ronzio: Strava.

Brad Weimert: Love it.

Jonathan Ronzio: I’ve got the London Marathon in two weeks, so that’s the one open on my phone.

Brad Weimert: Damn. That’s ambitious, man. That’s awesome.

Jonathan Ronzio: No, actually, I don’t look at the KPI dashboards of anything in the company on my phone. I contain that to work. I mean, I’ve got Slack on my phone and email on my phone, but I’ll check in and coordinate and collaborate with the team via mobile.

But generally, I like to not let that be a distraction when I’m out with my family or on an adventure with you up in British Columbia or whatever it might be. So, I keep most of those dashboards and the real meticulous insights and analytics on my laptop here.

Brad Weimert: That’s amazing. I don’t know how to do that. You have to teach me. So, that’s actually a really relevant consideration for, I think, most entrepreneurs. I think most entrepreneurs feel like they’re pulled in a thousand directions all the time. And the vast majority I see behave that way. And it is the few that seem to have some sense of, I’m going to call it balance, but my approach to life has defaulted heavily in the direction of alignment over balance. And so, I’m trying to find the activities that I can do that feel like they enable me to experience other parts of life without losing sight of, or motivation for, or the drive towards the primary objective of the business. How do you look at balance versus alignment?

Jonathan Ronzio: I love how you say it. I think that balance on a short-term scale is total BS. I think that anybody thinks that they need to have their, like I work my nine to five and then I clock out and I don’t touch anything, and I hang out with my family and they’re like, on a daily basis, that just doesn’t work for me. I try to look at balance. I agree with alignment in terms of like what I’m pursuing in a year. I look at the macro of it and make sure that my year has enough stuff with my wife, enough stuff with the kids, enough stuff music-wise with my band, and taking into account all the things I have to do for the business and all the different trips and events and board meetings and whatever else, travel and adventure, and stuff. I make sure all that is reflected in my year so that on a day-to-day or on a week-to-week or month-to-month basis, certain things may take more priority, more attention share from me.

And like, sometimes you have to grind harder to push different goals forward. And then other times, there’s a little more leeway in this area of your life. And so, you can pour more energy into the other bucket that you need to fill up. But I look at it on more of like an over time, do I feel like I am giving enough attention to give myself fulfillment in the areas that matter, like all the different areas that matter to me versus do I have work-life balance today?

Brad Weimert: So, I think, what I kind of heard, and maybe, I don’t know, this is just how I internalized it, but was sort of alignment in the day-to-day balance in the aggregate?

Jonathan Ronzio: Yeah, I would say so.

Brad Weimert: Okay, let me go back to fundraising here. So, two rounds, and at some point, Daymond John joined the cap table. And it sounds like you had this kind of ongoing courtship or relationship with him where you’re talking and at some point, he came in on the cap table. Why was bringing him an important to you? And did he have some cultural imprint on the company? What was the significance of that particular participant on the cap table?

Jonathan Ronzio: Yeah. So, when we did first start raise, running Facebook ads, this was back before the Advantage Plus and kind like AI doing all of your targeting for you on these channels. It was when you had like real targeting based on lookalike audiences. And so, we would select people like Gary Vee, people that watch Shark Tank, people that read Entrepreneur Magazine, like we had this profile of people that we were going after.

Now, our ICP has changed over the years. So, today, it’s less that audience, that’s small, small business audience, a little more mature. You have to have management layers in your company and mature SMB. But in the early days, the founders of small companies we were targeting for early adopters of the product and Shark Tank, and the Sharks were very effective, lookalike audiences for us. And so, we knew that if we could collaborate with one of them and get them to endorse Trainual, we could run that as an ad and that would stop people scrolling in their feed more than just seeing a selfie video of me.

Not that those didn’t work, but we borrowed some brand authority from Daymond. So, yeah, we initially engaged him for our virtual user conference. The first time we did it was November of 2020. And so, this was like when all these speakers, their speaking roster went out the window because of the pandemic. And so, then now they were taking every virtual thing that they could, so we got Daymond for chief to do like opening Q&A or like the keynote Q&A of our playbook events.

And after that event, his team reached out. He was like, hey, he really likes what you guys are doing, liked your vibe. Like, let’s keep talking and see if there’s some alignment here. And we just kept talking until separately, we had the series B that was happening and he ended up participating in that. And I wouldn’t say he left any kind of cultural imprint on the organization. He very seldom interacted with most of the team. But he spent time with Chris and I or a couple other people that would be involved in shooting commercials when we get together.

But no, it was a really effective partnership for many years. And we’re still friends. He’s still on the cap table, but he sends gifts to my son every once in a while. But we’re not using him in commercials anymore because we go after a different audience.

Brad Weimert: Is it exclusively FUBU that he sends him? Is that weird?

Jonathan Ronzio: No, no. It’s like this shark box thing that he has where like, it’s a video, where you open up the box and there’s a video of him. And that’s what my 4-year-old just freaking loves. He opens up the box and he sees Daymond dressed in some sort of crazy outfit and talking about like whatever’s in there that’s like new products that he’s testing out and sending to people.

Brad Weimert: Oh, dude, that’s awesome. What a clever gift for him. Just promote his own sh*t and get some hype around it. That’s amazing, dude. And everybody likes it. No, I love that. All right, so Trainual has gotten accolades for culture and from the moment we hit record today, that came up. And the shocking answer of what SOP do you document first was core values and culture related. Are you in person? Are you remote? Are you hybrid?

Jonathan Ronzio: We’re a hybrid team. About 60% of our 120 employees are in Tempe, Arizona, or that’s where the HQ is, but they’re in the Arizona area, but I live about 20 minutes south of Boston. So, I go to the office maybe once a month or once every other month for different events and planning sessions, but I’m primarily remote.

Brad Weimert: What specific cultural practices do you have to ensure that you have strong culture in-house and throughout the remote organization?

Jonathan Ronzio: Yeah, I mean, in-house, we’ve got an amazing people ops team. I think one of the things that we did really well is we prioritized hiring a people leader. I think a lot of people wait until their business is a little bit bigger than we did. Like, I think our VP of people was maybe our 13th employee. Before there were real teams with multi-management layers and real HR issues. We knew we wanted to invest in that.

And one, it’s a matter of who not how, right? And Chris and I love people and love the team, but like also didn’t want to be the ones in the weeds of dealing with some of the issues that were coming up in the HR side of things. And we wanted somebody who was passionate about that so that we could focus on growth strategy and product strategy, right? So, we hired a people leader very early, and Sasha, to her credit, has built an amazing people operations function that really has dialed in the in-person experience, like whether you’re in person or remote, we fly everybody into the company for their first week of onboarding, roll out the red carpet for them in every possible way. We care, obviously, because it’s our product. We care a lot about the onboarding and training experience. There’s plenty of events that happen at the office all the time, different activations.

And then from a remote standpoint, like similarly, we have affinity groups set up. So, everybody via a Slack channel, there’s ones about family, there’s ones about certain ethnicities and heritage, celebration, there’s stuff about pet owners, there’s stuff about music releases and like any kind of thing that you can imagine that multiple people are interested in. They’ve set up clubs for inside of Slack and then have Zoom engagements every once in a while for those clubs as well.

Brad Weimert: Two things, one, I find Slack to be horrifically disruptive. We use Slack for urgent communication, is the label that we put on it inside of the company because I don’t want it to distract people throughout the day, and just like your phone and text messages or an inbox, but now it’s really text messages on your phone, it can drive your entire day if you let it.

Jonathan Ronzio: If you let it.

Brad Weimert: If you let it. So, do you have rules in place or how do you think about those Slack channels that are there to build and promote culture intersecting with their day-to-day work? And how do you architect that and make sure that it does what it’s supposed to do?

Jonathan Ronzio: I mean, we live in Slack. Like, nobody internally emails each other unless they’re on a thread with somebody externally. Everything is communicated in Slack or a meeting in Zoom or an in-person meeting. But there’s no micromanagement on this. It’s just we trust our people to get their work done. We trust our leaders to assign the right priorities and to be managing accountability on deadlines and results.

And as long as the work is happening, I don’t care if somebody is jumping in the family matters Slack channel a couple times a day to like somebody’s photo of their kids and in between their meetings of other important stuff they have to do. Everybody’s adults and everybody can manage their own stuff as long as we’re accountable to the results at the end of the day.

Brad Weimert: I have a fear that things get lost in Slack and that it’s not a great place to track things. How do you pull project management out of Slack? Or how does it get intertwined with that fast-paced communication inside of Slack?

Jonathan Ronzio: So, project management, we use Asana. So, anything specifically related to deliverables or projects that need multiple people oversight on, it’s all running Asana. Slack is more for quick feedback, conversations, questions, that kind of stuff. So, there’s pretty good delineation. And as far as like searching Slack, I mean, you can search for anything you need or you can pipe Slack into Manus as well and you can ask the AI to search whatever you need.

Brad Weimert: Yeah, that’s a fair point. You mentioned events happening at the office. What do those events look like? Are they external events where you’re pulling in prospective clients? Are they parties? Are they yoga sessions? What does it look like? What are you doing for these events that you do at the office to build culture?

Jonathan Ronzio: Yeah, I mean, a lot of it is just team lunches. We’ll bring them catered lunches. It’s generally more employee focused. We very rarely have partner events at the office. But a couple times a year, we might bring some people in. But there’s trainings. There’s our, like– we have a cadence of every other Monday, we do an all hands and anybody who’s in the office is getting together, gathering in the training room there. Every quarter, we do a whole quarterly all hands that’s always themed and we get everybody to dress up and stupid things like– one of the themes was like pick your favorite decade. And everybody else was picking like ‘50s, ‘70s, ‘90s, whatever. I picked the 1790s and I went full like George Washington garb.

Brad Weimert: Amazing.

Jonathan Ronzio: So, yeah, we really lean into that kind of fun stuff. So, there might be wine tastings in the office. There might be, everybody go to a movie.

Brad Weimert: And your head of people guides this?

Jonathan Ronzio: Yeah. Her and her team. They do. They do a great job. But I mean, it came from us at the beginning and just wanting to build a place that we wanted to work and bring in people that we wanted to work with, like good humans that are driven, that are talented, and that bring a heart and passion to the table. So, we have a high bar for people coming in. I mean, we’ve let people go that are absolutely stellar at their job, but that just are not core values fit and don’t collaborate and communicate and have too much ego or too much entitlement, like that’s just culture cancer and that’s got to go despite how good they are.

Brad Weimert: Yeah. I was just talking about this actually. I just did an episode with Dan Brisse, who we were snowboarding with at– he is amazing. And we were talking about values and kind of, I’ve learned the value of values over a long path. How do you define culture at large? Because I think, being clear on what that is or what that looks like with anything, if you can clearly define it, it’s helpful. How do you think about it? And how do you actually define the culture of the company?

Jonathan Ronzio: I think it’s the feeling of belonging and purpose where you work. Culture is related to community. And so, the old adage of like people leave managers, not jobs, right? That’s because they don’t like working with that person. They feel belittled or micromanaged or like there’s aggression. So, people might leave that. And so, I think a good culture that is self-selective of good people or the right people that choose that this is where I want to be and I feel good about being here and thus, I am motivated to help achieve what this company is aiming for.

Brad Weimert: I like it. Okay, I mentioned this before, you are a dynamic human. You’ve got a band. You’ve got instruments behind you. I met you through snowboarding in the backcountry in British Columbia doing inappropriate things that might get us hurt. You’ve climbed some mountains. Specifically, you made this award-winning documentary about your journey between Aconcagua and Denali. What lessons did you get from climbing those mountains that have made their way into Trainual’s culture or your leadership style or just a part of business in general?

Jonathan Ronzio: I am the leader I am today because of my early mountaineering days. I think that everything about those adventure pursuits informed my day to day in terms of what I bring to business. And like, no decision is difficult for me because I’ve made life or death decisions in the backcountry. And I think that when you have those benchmarks, where you’ve literally– there were times on Denali, where like, well, I’m having, and I was always leading the team too, so like I would have my rope team, I had to understand everybody’s skill on the team. I had to figure out how to navigate us through a whiteout on a crevasse field with slopes around us and Abby conditions and punching through crevasses as we go through and trying to get around that stuff and like have to make split second decisions based on how the weather changes or based on how the snow conditions change in order to ensure the safety of me and my team and understand that we’re all working together.

I’ve lived through times where people on the rope team did not work well together or didn’t know what their role on the team should be and that led to frustrations. And everything about the resilience and the grit and the determination and the decision making and the ability to find comfort in uncomfortable situations has translated to how I think about business strategy and leadership and how I build the team, even from a standpoint of just like reporting structures. I know that you don’t want more than five or six people on a rope team. And five or six is what I think is the max of your ability to actually effectively manage direct reports.

Brad Weimert: Yeah, for anybody that has not spent any time mountaineering, which is probably 99.9% of the audience, navigating through a crevasse field in a whiteout is a terrifying proposition. I’ve done just a couple little baby mountains, relatively speaking here. I did Mont Blanc and then the Matterhorn, which are dramatically different. Yeah, blast, super fun. And that was my crash course. I had never done anything crash course into mountaineering with a buddy.

But have you ever fallen into a crevasse? Can you explain what that whole dynamic looks like? And if you’re walking through this field, what the danger is, how you circumvent the danger, and what happens if you fall in?

Jonathan Ronzio: Yeah, I’ve punched into some but without fully falling, fortunately. When you’re split boarding, it’s a little easier. You have like the board covers more surface area, so you might punch down in certain spots, but you don’t fall completely unless the crevasse is absolutely huge. But I have jumped into one as a training exercise and that was wild on Mount Rainier. So, yeah, I mean, the biggest thing to watch out for is snow bridges. That’s where people get– when I’m talking about punch through, is that’s what it is. You can’t see that it’s there other than maybe a slight depression in the snow, but if it’s a whiteout or if it’s flat light, you might miss that. And then you, you know.

Brad Weimert: Let’s explain what a crevasse is, first of all.

Jonathan Ronzio: Yeah. A crevasse is basically all the snow that gathers on the top of a mountain compacts over time and it moves like a slow frozen river down the mountain. And you get to a point where the actual frozen mass of ice that is moving down that mountain starts to crack, and that’s called the bergschrund. And then underneath that, it becomes like an open crevasse field. And the cracks in the snow, as it moves, build. Like anybody who’s watched anything on Everest, there’s like the Khumbu Icefall. That’s like the end of one of those glaciers moving down a mountain. And so, crevasses are cracks in the glacier that can be small, can be massive, and a lot of times, they’re hidden by recent snowfall.

Brad Weimert: Yeah, and they can be anything from a couple hundred feet to several thousand feet. And if you fall, this is the purpose of ropes, right? So, you’re roped up to the other people on your team, and if you fall, the role of your team is to stop-arrest, which is basically just fall down and dig their ax into the snow to stop you from sliding because you get your whole body as the surface area onto the snow, which that drag actually has tremendous power in stopping a fall if you do it right away. So, never a full fall, but you’ve had scares.

Jonathan Ronzio: Yeah. But like the lesson in the learning about crevasse rescue technique is, as the person who falls, it is your responsibility to try and save yourself. As the person who like arrested the fall, it is your responsibility to try and save the person who fell. And you’re working towards the goal of savior from both ends. And like that can translate, of course, to anything that you do on your team as well. That’s like, we have a core value that carry the groceries. It’s like help others out, right? It’s not just about you or them. And so, you’re both trying to achieve the same outcome as a business. And so, figure out from either end, like who’s going to get there first? How can we help each other, right?

Because if you actually fell, if you didn’t go unconscious because you hit something and you’re just hanging there on the rope, it’s now your responsibility to use what are called ascenders or a Texas foot Prusik, which is a system that allows you to slide a rope and keep pressing your foot into the rope and keep climbing up. You do that while at the same time, the people who arrested the fall, ideally more than one person, you have one person still dug in on their ice ax, and then the others are setting up a Z-pulley system on taking slack off of the rope so that everybody can get up. And you’re not reliant on somebody just dangling on an ice ax to hold you. You actually set up some ice screws and snow anchors that then you can set up a pulley to get somebody out, but you’re working from both sides to achieve the same result.

Brad Weimert: Yeah, that’s terrifying. Okay, so I don’t know if you’ve thought about this, and this question might go nowhere, but in your documentary, you have a section where you got stranded on a Chilean beach between these two mountains that you were climbing. That clip is the most replayed section of the documentary that’s on YouTube, which is one of the places you can find it today. What is the Chile beach moment that every founder could engineer in their brand story?

Jonathan Ronzio: So, yeah, that was not in the plan. That’s the lesson there, right? Like, when we think back to the entirety of what that trip was, of course, we had amazing times on the mountains, of course, like the actual road trip and hitchhiking and everything through Route 1 of the Pan-American and all the countries, and all the volunteering that we did was amazing. But when me and Ethan and Ryan get together and talk about that trip, we always reflect on Arica Chile, which is where we got stuck, not being able to get our truck that we bought in Santiago over the border into Peru because of some paperwork issue. And so, in order to keep going on the trip, we had to actually just like live on the beach out of our high altitude mountaineering tent, and every single day for two weeks, try to figure out how to sell that truck on the street.

And that unexpected two weeks living on the beach and just interacting with the people in this town, this like northern border town, the last annexed territory in Chile, was the most memorable part of the trip. And to be honest, I didn’t even know that that had that stat as far as like the most replayed thing on the YouTube video, but that’s amazing. And it’s because it was such a special, unexpected moment of the trip. And I think that that is the lesson is that when you start your business, the most memorable part of your entire business journey is not going to be something you can plan for. It’s going to be when a disaster strikes or when something in the market changes and you are forced to adapt and you’re forced to think inside of yourself and figure out and go deep and how resourceful and resilient and creative can I be to get through this. And that’s what’s going to make the biggest impact for you in your life and in your business.

For us at Trainual, we could never have foreseen the pandemic. There was no strategy for how to get through that, but that was one of the most meaningful parts of our entire business journey in terms of how the whole team adapted to all the changes that came from COVID-19. Similarly, when SVB collapsed, my brother and I were on a boat on our way to Antarctica. And our series B funds were in the SVB at the time. Fortunately, everything worked out, but the time we spent on the Drake Passage, trying to figure out what to do with our company, if all of our money went to zero, and like, what would we do when we came back from Antarctica two weeks later? How would we course correct that? That is one of those moments that you find out what you’re worth.

Brad Weimert: Adventures in general, do you do them for the experience or for the story?

Jonathan Ronzio: Both. And the stories are amazing, but I’m just innately drawn to experience new things and to push myself in new challenges and see new places and experience new cultures, communities, sites, whatever. It was something– I played traditional sports growing up, but I was never really into them. I didn’t go too deep down like the baseball or the basketball route. I don’t watch professional sports ever. I watched Planet Earth when that first came out in Discovery and was like, I got to New Zealand. Like, I need to experience the world, and then just became addicted to travel and adventure and pushing what we’re capable of. Like, we have finite time on this planet, and I’m trying to live every life that I can.

I want to be a musician. I want to be a SaaS founder. I want to be an adventurer. I want to be a dad. Who knows what’s next? Maybe I’ll start a brewery or something. I have no idea. But I’m trying to live every life and I’m trying to do more on this planet in my time here than anybody else that I know. And if there’s people that are doing more than me, I respect the hell out of them and I want to be around them and learn from them.

Brad Weimert: That’s dope. Yeah, I ask because my experience in adventures is there seems to be some critique amongst adventures for those that are doing it just for the story. And the more experiences I have that are unique, the more I believe that the story is a major part of the experience because the experience is locked in time and you get to have that experience with the people that you do it with and you bond with the people that you do it with. But the story stays with you forever. And the amount of relationships that you can build through sharing the story far exceeds that you build through the experience itself. It’s very different, but it’s certainly a big part of that experience for me as well.

Jonathan Ronzio: Yeah, I agree. I mean, it’s the definition of type two fun, right? Like, any of the things that we do that hurt in the moment, that like when you’re taking your next step at mile 40, crossing the rim to rim to rim in the Grand Canyon, and you’re trying to back up that last self-rim, the head wall, it’s not feeling good. You’re like, why? Why the heck am I doing this? But then as soon as you finish, whether you share that story on a stage or on social media or never, but you reflect on that story with the people you were there with, the story always is what makes it worth it in the end.

Brad Weimert: Or in a lodge in the middle of nowhere of British Columbia as it was.

Jonathan Ronzio: That’s right.

Brad Weimert: Yeah, I love that. Outside of snowboarding with me in BC next year, what other adventures do you have lined up?

Jonathan Ronzio: So, like I mentioned, I got the London Marathon in two weeks. I’ve got 29029, the Everesting challenge in Whistler at the end of August. I have the Berlin Marathon at the end of September. Yeah, yeah, so after knocking out London and Berlin, I’ll just have Tokyo and Sydney left on the majors. So, hopefully, those next year in addition to obviously the Baldface trip. And then other than that, a ton of time with family. I think we’re going to Italy for my mom’s 70th in November, and actually, last week, I got word that I got my dual citizenship for Italy.

Brad Weimert: Crazy. Why’d you do that?

Jonathan Ronzio: I mean, if I didn’t do it, my kids would never have been able to. There was something about like the timing of it, you had to be a certain amount of generation removed and after that, like you wouldn’t have the ability to claim it. And so, my great-great grandfather, Rafael, came over from Italy in 1913. He happened to have children in the United States before he naturalized. And so, based on a couple different things, like I qualified. And so, my brother and I went for it and we got it. Now, our sons have it as well. Our wives can have spouse residencies without having timed visas. And now, we can open businesses anywhere in the EU or have property anywhere in the EU. And so, that’s exciting.

Brad Weimert: Cool. Okay, so you have all these other things going, and this idea of balance and alignment is fascinating to me. For those things, which are very clearly life-enriching activities, both the type two sh*t, like running marathons or adventures that crush you physically, and also, the ones that are purely enjoyment, right? And I look at Baldface that way, right? I look at adventure snowboarding that way, backcountry, HeliCat, whatever.

But then you have this other chapter. So, you launch BreakBot, which is seemingly like a side hustle. You have a funded company that is accelerating through this new change of AI in an ever-changing world. How do you think about having your head in the game and building your core project or doing these extracurricular activities like BreakBot? Was that a strategic brand play or was that a creative release? Was it a side hustle? Where does that fit in? And how do you rationalize that versus it being a distraction?

Jonathan Ronzio: Yeah, so I’ll answer this in a couple ways. The BreakBot in and of itself was actually a lead gen tool for Trainual. So, it was like, during the pandemic when everybody went to Zoom and everybody was just getting booked back to back to back to back, I was feeling that. It was like, what? I never have time to even get up to take a piss or grab a coffee. And everybody’s complaining about this. And so, I just like, work to create AI, a Google app or a Google Calendar plugin that like, automatically, you set the rules and it automatically scanned your calendar and added whatever size breaks, like 10 or 15 minutes breaks you wanted if you were booked for three hours or two hours, whatever parameters you set, just automatically added breaks to your day to take care of you proactively.

And the value prop there was, like if you actually opened up the thing to set your settings at the bottom, it was like saving time. And that was the CTA, and you’d click like saving time and it went to a landing page for Trainual that explained everything about how Trainual saves time in your business for your operations, your onboarding, and training and stuff. So, it was a free tool I made just for myself to solve a problem. But then I threaded the value prop back to Trainual to make it a lead asset.

Separately, to answer your question though, I do just create things on the side every once in a while because I want to. I just have, I don’t know, like an obsessive compulsive/creative disorder or something. And so, like when things pop into my head, I just sometimes have to act on them. Like I vibe coded an app for my band to manage all of our songs, shows, set lists, venue analytics, contacts, all of that. And it was working so well for us. I just spun it out as a new thing called Setlistly. And now, there’s like 150 bands that are using Setlistly and that’s like growing on its own. And I’ve got music influencers just promoting it and it’s like, the thing is there’s no stress tied to that. Like it could go to zero, but it’s still a cool app for me. But it’s like, cool, if other people want to use this and pay for it, awesome. But it’s not the thing I’m pouring all my energy into, but I had to create it because I wanted to. But the primary focus is still obviously what we’re doing with Trainual.

Brad Weimert: I love it. What advice do you have for a 25-year-old entrepreneur who is torn between business focus and exploration?

Jonathan Ronzio: Find a way to do both. Honestly, I’m an and, not or guy. And the very start of my career, what was really like, I told you about the video company. I had this background in video production. I had studied marketing in school. I was obsessed with adventure and I ended up getting this opportunity with Old Spice, where they sent me out to Zermatt, to the Matterhorn, when they launched their Matterhorn deodorant scent. And for two weeks, they just paid me to do crazy stunts around the glacier and the town of Zermatt to promote the new product when social media was brand new and vlogging was new and I was tweeting on their account and stuff. And that like combo of things hit me and that’s what inspired between the peaks.

It was like, well, I’m graduating business school, but I don’t want to go work at a day job behind a desk. I want to go explore the world, but how do I take that passion for exploration and weave it into my baseline of production knowledge and business knowledge and marketing and PR and let me figure out how to get brands that want to be involved with this to give us gear or help us promote it? And so, I approached that project like it was a business and that became a foundation for everything I did with Explore Inspired my media agency after that. And then all those skills fed into Trainual. So, I would say do both.

Brad Weimert: Dope. Where do you want to point people, man? Where can people find out more about you, Trainual, or whatever else you want to throw their way?

Jonathan Ronzio: Yeah, I mean @jonathanronzio on Instagram is probably where I’m most active, or @jonathan.ronzio on TikTok. You can connect with me on LinkedIn. It’s just my name on there as well. You can check out Trainual.com. If you’re interested in my music, you can find it on my socials. I actually just released a single today.

Brad Weimert: Amazing, man. I love it, dude. Well, great catching up. It’s good to hear more of the story and I’ll look forward to the next adventure.

Jonathan Ronzio: For sure, man. Can’t wait.