How To Use AI to Scale Your Business

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200 Employees, One Founder, and a Whole Lot of AI

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The AI Playbook: How to Build More With Less with Jon Tucker

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This week on Fundraising Demystified, I sit down with 
Jon Tucker, founder of HelpFlow, who bootstrapped his company to 200+ employees and is now using AI to outcompete, automate, and scale faster than ever.

What you can expect:

  • 01:30 - AI’s impact on customer service & workforce reduction
  • 04:00 - The Importance of Evaluating AI Performance
  • 07:15 - How AI enables business efficiency and scalability
  • 12:45 - AI’s role in startup growth and venture capital trends
  • 18:30 - AI workflow automation & AI-assisted coding
  • 24:00 - Future of AI: Chief AI Officers, automation, and scaling
  • 28:30 - Boardy AI and next-gen AI-powered networking

Watch it Now

ABOUT JON TUCKER

Jon Tucker is the CEO at Help Flow. Over the past decade, he’s managed remote teams and faced the frustrations of micromanaging every detail—an experience that drove him to embrace AI for smarter delegation.

Through HelpFlow’s “smart staff” model and their proprietary GuideLayer AI, Jon transforms traditional virtual assistants into high-value, autonomous team members. His goal? Free founders from busywork so they can scale faster and focus on what truly matters. Ready to see how AI can change the way you work? Try the AI at HelpFlow.com/demo-ai-video.

Connect with Jon Tucker

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How To Use AI to Scale Your Business

Jason Kirby (00:13.401): Layering AI into your startup, um, to maximize runway efficiency and profitability with reducing the need for outside capital. So something along those, obviously not that keyword, but something along those lines of the, you layering, using AI at your startup today or something like that, or like, can you integrate integrating AI into your startup? Um, something along those lines. And then we have this graphic that.

Jason Kirby: Here I'll flash my screen so they know what it is.

Jon Tucker (00:44.632): Yeah.

Jason Kirby (00:48.377): Entire screen, sure. So I'm referring to this graphic here. I'll send you guys the link. There will be publishing this week, so try to give as much help as I can.

Jon Tucker (00:51.607): It.

Jon Tucker (00:58.444): Yeah, think another, I think a way that might actually frame it up with that image too is like the leverage your team can get from AI. So like getting leverage as a team with AI, something along those lines. I don't know what the SEO keyword is, but like that's the core of how I think of AI is like, I get 5X more done than another CEO that like doesn't use AI, right? Like every one of my team is the same way.

Jason Kirby (01:21.442): So that's interesting. Think, just given our relationship and stuff like that, I think it'd be interesting maybe to also discuss how we're using AI. So how we're using AI in our companies, you know, pre when AI wasn't a thing. And so I'd be interested to like, have you—so like we built our companies before AI exploded and how we're adopting AI in our business today.

Jon Tucker (01:33.165): Yeah.

Jon Tucker (01:40.098): You mean repeat that so I understand what you're saying.

Jason Kirby (01:49.241): And so I'm, it's more geared towards you of having a 200 plus person team. Um, you know, bootstrapping since day one and now how are you leveraging AI today.

Jon Tucker (02:47.626): Let me know. So you're going to do—can you give me kind of the quick frame of the whole thing? So you're doing intro. We'll do some questions. First question is essentially like, what is the first question generally?

Jason Kirby (02:48.217): You.

Jason Kirby (02:59.065): Um, you know, welcome to the show. Um, you know, can you tell us a little bit about your, you know, how you bootstrapped your business, uh, to 200 people and that's all a start. And then I'm like, well, now how do you think about using AI when you have 200 people—like low, you know, low cost, you know, should I say low cost labor?—is that okay if you're team? All right. Um, know, scaling to 200 people overseas to, how are you going to leverage AI now, uh, with that workforce?

Jon Tucker (03:19.778): Yeah, that's fine.

Jason Kirby (03:29.049): So that's how we'll do that. All right.

Jon Tucker (03:30.796): And then service at the end—won't integrate it into every question—like how, how will you, or how should I address the service that we do?

Jason Kirby (03:42.201): So I will, at the very end, I will, like, if it weaves in, you can explain what you do. Like that, it's like, hey, you bootstrapped your business to—know, to teach your people—tell the audience a little bit about what you built. And then we'll talk about now how do you use AI? And then we'll go into, then it'll be a back-and-forth conversation about how startups need to be using AI today in their business. You know, they might not be an AI company.

Jon Tucker (04:33.985): Cool. All right, I'm good with that, dude. And then how long is it? Just so I kind of know roughly where we're at.

Jason Kirby (04:37.529): We might be wrapping up at the end of the hour. Do you have a hard stop at the end of the hour? I would like to keep it up to wrap it up at the end of the hour, but if it goes over, fine.

Jon Tucker (04:41.678): No, no, I'm good.

Jon Tucker (04:47.97): Cool. Let me message my team real quick because I have a 1pm with them, but I will tell them I'll stock them when I'm ready. JC.

Jon Tucker (05:04.302): All right. Let’s turn all this.

Jason Kirby (05:06.061): And as you talk, make sure to try to focus on the camera when talking.

Jon Tucker (05:10.067): Yeah, absolutely. Yeah, I got it up there too. I might actually click away from Riverside to like not see you. That'll help me, I think. I won't close it though. I know the process. Actually, it's like I can see me over here. Is there a way on Zoom to turn off my video for me? There's not, right? Let me see here. Speaker split screen. There you go. Follow host view. That didn't do it.

Jason Kirby (05:17.049): It'll help you.

Jason Kirby (05:31.953): Don't turn it off, because then I won't know if you get recorded if you do something like that. I have to be able to see you, I think. Let's just...

Jon Tucker (05:35.758): Okay, yeah, okay, cool. You know what I'll do? I'll put my notes over me and that will work.

Jason Kirby (05:41.793): You can look at me, but when you talk, try to make eye contact with the camera. All right.

Jon Tucker (05:45.506): Yeah, got it.

Jason Kirby (05:51.833): Roll. All right, now we're starting. If there's any tidbits from that part you can use, go for it. All right, one, two. Hey everyone, welcome back to Fundraising Demystified. Today, we're going back in time a little bit with a very close friend of mine who pretty much introduced the word entrepreneur to me back when I was 18 in college. John, it's great to have you on the show. Finally, you know...

Jon Tucker (06:01.806): Everyone.

Jason Kirby (06:20.077): Bring our conversation into the public limelight. I'm so tired. I'm so excited to have you on the show. So John Tucker, founder of Help Flow, bootstrapper since day one of all of his businesses ever since I've known him. I'm excited to have you on the show, John.

Jon Tucker (06:41.388): Thanks, man. I appreciate you having me, man. It makes me feel old as we... As you said, I don't know if you said it in this intro, but like—we met when we were 18. We're not 18 anymore. So time goes by fast.

Jason Kirby (06:51.201): Yeah, it's been a long time. But John, the reason why I wanted you on the show is you and I have been riffing offline about integrating AI into our companies—how we're using it, how you're using it. You're on a 200 plus person organization and it's heavily built on human labor. And you're being so proactive in integrating AI that I thought it'd be important to have you on the show.

Jon Tucker (07:37.294): Yeah, so Help Flow started as basically a customer service agency in 2014. So it's been a little over 10 years. And by CS agency, I essentially mean doing customer support for other e-commerce stores. We have agents, we staff those agents, we train them, and they do customer service for our clients. And so started that in 2014. I've always been really tech-minded. I remember hacking together our initial technical systems to learn the client's business and give the agent the right resources. At our core, we're a people business—doing customer service at first—but we've always been technical and systems-minded. Fast forward, now we provide virtual assistance for any business for any role, not just customer service, and we layer AI onto the entire thing. It's an AI-empowered human virtual assistant. And we've been able to accomplish a ton with AI over the last couple of years. That's the journey in a nutshell.

Jason Kirby (08:46.669): What's interesting about this—and what I think every founder needs to consider—is that we always look at growing headcount to handle more capacity. But with all the AI tools you’re using, how does that change your staffing requirements?

Jon Tucker (09:14.222): Yeah, I would answer it in two ways. One, with customer service, it's very systematic. A couple of years into the business, I realized technology is going to replace this, and over the past couple of years, AI can handle many tier-one questions. In our core business, you might need half the customer service agents you used to. Internally, it's an efficiency game. A team member in sales, for instance, can handle two to three times the deal flow compared to competitors using basic AI. We're leveraging AI across various steps—from meeting prep to email outreach—so we're effectively supercharging our team.

Jason Kirby (10:55.043): What comes to mind is competitive pricing. With AI-supported staff, you can lower your price and still maintain profitability compared to full AI automation solutions, while keeping the human oversight many people value. So, how do you think about building these systems? Is it through Zapier integrations, custom code, or something else?

Jon Tucker (11:41.292): I always consider myself very systems-minded. I remember someone once said, 'John, you're an algorithmic thinker.' That stuck with me. For me, algorithmic thinking means breaking down a process into steps. For example, one friend mentioned how process-minded I am when preparing for a meeting. It’s crucial when working with AI—you have to be very specific. You can call it prompt engineering. Our team culture is based on this mindset, which lets us communicate effectively with AI. Over time, we evolved from Frankenstein-like Zapier integrations to custom code, especially after understanding OpenAI's suite of APIs. Today, we even use agentic AI that acts like a team of humans doing research, quality checks, and more.

Jason Kirby (15:07.417): Then, what about tracking all that tinkering? How do you keep track of all the tweaks to prompts and data inputs?

Jon Tucker (16:01.566): EVALS. When you build AI, you need quality control. EVALS are essentially your quality checks. You define what you want and then measure if the AI meets that standard. Once it reaches a certain point, you stop tweaking. Of course, if there are major changes, you re-run your evals. It’s similar to how you’d test software—there’s always room for improvement, but having a clear metric helps set an endpoint for tinkering.

Jason Kirby (18:05.433): And that's usually what I run into. It takes a lot of tinkering, but in the end, it's worth it. Our team uses similar processes, especially when building our own AI tools for Thunder, like our capital strategy assessment.

Jon Tucker (19:01.602): Exactly.

Jason Kirby (19:04.697): The takeaway is that while AI can handle 70% of the work, there's still that human element needed. And it’s transformational—what used to take weeks can now take hours.

Jon Tucker (20:45.294): And when advising businesses, I often say that everyone wants to integrate AI, but few truly understand how to implement it. The key is understanding your workflow and then fitting AI into it.

Jason Kirby (21:00+): [Discussion continues along these lines, diving into the challenges and opportunities presented by AI integration in traditional business models.]

Jon Tucker (23:01.474): But like our onboarding process—what used to take five or six days now takes about 90 minutes. The client does a 10-minute call with our AI system, and then our team reviews and annotates the output. We’ve spent 10 years perfecting the process, and AI has accelerated it dramatically.

Jason Kirby (24:33.463): And on the market side, I see many founders adopting AI either to outcompete or even to acquire less efficient businesses. It’s a transformational shift in the startup landscape.

Jon Tucker (25:55.406): Exactly. I'm even looking at a deal for a VA business that we could replicate. The typical VA business trains employees and builds skill sets. But with AI, you separate the tactical tasks from strategic decisions—AI can handle the routine stuff, while humans focus on strategy.

Jason Kirby (29:45.753): And there’s the margin game—if you're not integrating AI, someone else is going to capture that value. Your margin is my opportunity.

Jon Tucker (30:33.282): Exactly. OpenAI is winning the margin battle by taking over labor costs. Companies will either adapt and integrate AI or get left behind.

Jason Kirby (31:42.881): And look, with rapid adoption compared to past technologies, the gap is closing fast. Soon, every business will have a chief AI officer or equivalent.

Jon Tucker (32:24.376): Absolutely. Leaders need to understand AI at its core, not just delegate it to a specialist. Otherwise, you'll be paying someone else's margin.

Jason Kirby (32:33.717): I got something to add on that too. It’s like treating AI as an intern—expecting associate-level work but grading it on the same scale as a full-time team member.

Jon Tucker (35:10.094): Exactly. For software businesses especially, getting into AI-assisted coding is crucial. Even if you're not a coder, understanding the process can transform your approach. I’ve spent a lot of time learning front-end and back-end frameworks, and it’s made it feasible for us to build products using AI.

Jason Kirby (39:26.585): And that's why it's essential not just to adopt AI tools, but to truly understand how they work so you can integrate them into your business effectively. Your margin is my opportunity.

Jon Tucker (39:29.774): Absolutely, that's a Jeff Bezos quote, right? Your margin is my opportunity.

Jason Kirby (39:32.218): Yes, and it highlights how companies not embracing AI will eventually lose their competitive edge.

Jon Tucker (40:06.442): Exactly. And if you're not interested in learning the intricacies of AI, you end up paying for someone else's expertise—while missing out on capturing that margin.

Jason Kirby (40:11.565): And at the end of the day, despite the automation, there will always be a desire for human engagement. It’s all about supercharging what humans do best.

Jon Tucker (40:32.974): Exactly. Adapt or become obsolete—that’s the reality with AI.

Jason Kirby (41:00.729): Now, before we wrap up, can you share a bit about your pet project? How are you taking the latest AI tools and building something new?

Jon Tucker (41:10.094): Sure. I could go in a couple of directions—either the coding aspect or our broader approach to integrating AI into our processes. For those running software businesses, it's critical to dive into AI-assisted coding. I've been exploring how tools like ChatGPT, Claude, and others can integrate into our code base to expedite development without sacrificing quality.

Jason Kirby (43:05.592): I know we started talking about that, but it really highlights the need to build your own internal tools rather than relying solely on external solutions.

Jon Tucker (43:28.013): Right. And it’s all about having an interface that works. For example, some companies like Borty AI have shown innovative ways to use AI in networking—though they’re still figuring out the data challenges. It’s a complex problem, but it’s clear that the companies that figure it out will have a significant advantage.

Jason Kirby (43:35.128): Yeah, it’s interesting to see how these early experiments are paving the way for more robust solutions in the near future.

Jon Tucker (43:53.718): Absolutely. Workflow and evals are the keys. You have to treat AI like a human intern—clear instructions, repetition if needed, and context is critical.

Jason Kirby (44:12.377): Well, all I can say is it's worth the tinkering. John, thank you so much for being on the show. Really appreciate your insights and just catching up and having a fun AI chat. So we'll get this episode out and share it with our audience ASAP.

Jon Tucker (44:30.851): Absolutely. Thank you so much, Jason. I appreciate it, man. And for everyone listening, I hope it's been helpful. Get into AI. Get interested in it. Enjoy it. And be grateful for the time we have—this is the biggest change that's ever happened.