The following interview is a conversation we had with Alex Zekoff, CEO of Thoughtful AI, on our podcast Category Visionaries. You can view the full episode here: $21 Million Raised to Power the Future of Healthcare Automation

Alex Zekoff
Alex, thanks for chatting with me today. Thanks, Bret. Glad to be here. 

Brett
To kick things off, could we just start with a quick summary of who you are and maybe a bit more about your background? 

Alex Zekoff
Yeah, absolutely. So, Alex Zikoff, Co-Founder and CEO of Thoughtful AI. I started my career in Deloitte Consulting. So really just learning process tech systems, the fun SAP implementations, if you will, but really learned a lot about Fortune 500 enterprise process and engineering. I then got an opportunity to move to Japan, where I helped Mitsubishi set up a company called Mitsubishi Aircraft Corporation. I took that opportunity. I had a blast two years, learned a lot. After that, I was sponsored to go back to business school, found myself at the west coast, went to Berkeley for a couple of years studying entrepreneurship, design, thinking, venture capital. Since I was sponsored, I had to go back to Deloitte, the old golden handcuffs. 

Alex Zekoff
Fortunately, I went back into RPA and ML and started deploying software robots circa 2017 on top of systems like the SAP systems we had built earlier in my career. Really had the insight that if you really market size how many people on annual basis operate software, it’s $7 trillion of labor, move data around. And so I had a very quick insight that if you fundamentally believe that is going to be software, then this is a massive market. And I was willing to invest my entire career to start kind of going focus on that way. So left aloe. 2019 took the plunge. I met basically my girlfriend, now wife at the time, just told me, hey, stop working for people. Go out on your own and having to look back. 

Alex Zekoff
Started raising angel money in 2020, early investors and just have been iterating and pivoting and the classic entrepreneurial journey the last three and a half years. And to be honest, when we started this company, it wasn’t the aipowered healthcare administration platform, it was just bots. Getting bots deployed and trying to bring down the cost. And that’s where we’re here today. And so a lot of it’s just been a fun, exciting journey the last three and a half years to get here. 

Brett
So if I look at the timing there, you leave Deloitte, start the company January 2020, thinking, this is going to be so fun. This is an exciting adventure. And then what, two months later, Covid hits. Is that an accurate timeline there? 

Alex Zekoff
Yeah, it was like the universe was just handing me everything once in a platter. I think every entrepreneur, you just get these tests sometimes where when it rains, it pours. So, yeah, January I raised forty k from friends and family. My Co-Founder was first angel investor, so I was a single founder just trying to innovate in the RPA space robotic process automation. Happy to dive in later if any questions arise from that. Started building bots, got a first customer, a pilot customer. I’m really excited. Landed that in February, March hits Covid. I was extremely nervous or scared that I was going to lose this pilot customer because that was it, basically. I didn’t have enough Runway after the 40k really to go past that. And the customer called me, the CFO, and said, hey, this is a big initiative. 

Alex Zekoff
We’re still going to work on this. We deployed our mvp of our platform plus the product in six weeks. Remote got to a first sort of pilot revenue. It was $2,000 a month. Very excited. The time that we got to that in four months. And from there, we’ve just been, I think, a combination of very blessed with the timing, been able to raise money at the right time, been very iterative in that process, and we’ve just taken it day by day, week by week to get to where we are today. But, yeah, it was definitely a lot in Q one of 2020 with COVID landing a customer, building an mvp of a platform, and just sort of hoping and praying it all works. It is sort of the first sentiment in the first three months there. 

Brett
So a lot of my friends who work in consulting like that, they tell me it’s very tedious, it’s a lot of work, it’s exhausting. And a lot of them tend to kind of stick with that path once they start on it for you. When you started down that path, did you have in the back of your head this idea, yeah, maybe I’ll start a company someday. Or were you initially planning to really make consulting your career? 

Alex Zekoff

I hit this fork in the road post MBA. I was 32 at the time, and I had to make this decision. And the decision was, do I keep investing into consulting? My career, my time, my energy. Do I go for partner sales track? Probably make that when I’m 40. So put another eight years in, and partners at big firms like Deloitte, McKinsey Bay and BCG, they make great money. And so I thought that was obviously a path that could have led to a nice monetary outcome. But then I started weighing in the risk. The risk is what happens when I get eight years in my career. I’m 40, and I don’t make partner. What do I do then? And so just kind of playing the no regrets situation, I said, this is the time in my career to take risk. I have no kids. 

Alex Zekoff
I was just dating my girlfriend at the time, really, no liabilities. And so I said, let’s jump off here. Let’s take the risk. Because if I spend six to eight years grinding on something I love and it doesn’t work, I had conviction that those skills would be useful in the market, and at least I went for it. And I would look back at my life when I’m 80 and not have a regret that I didn’t take that chance when it was the right timing in my own career and knowledge. And I actually had enough ability, I think, at that point, to take the leap, learning enough skills to actually learn how to raise money. Have worked in consulting for ten years, so I actually had some expertise in some systems design, managing engineers. So for me, that was the bet. It did pay off. 

Alex Zekoff
It doesn’t always pay off, but I had high conviction in the market were going after, in the solution space and in the problems were solving. So that was, for me, betting on myself and going for it. 

Brett
What founder do you admire the most and what do you admire about them? 

Alex Zekoff
I’m going to go with my dad. He is one of the still at 66 years old, puts in 80 hours work weeks and grinds, and is constantly iterating and innovating. And he’s a veterinarian, so by trade he’s a scientist, practitioner of medicine, but he built his own practice when he was 28 years old. He took the leap, too, and got into business. He didn’t know what he was doing and just figured out along the way. So as a kid, watching him go through that journey, watching the stresses, seeing the wins, seeing the monetary rewards of him selling his practice, that really gave me, I think, a lighthouse to model. I think early my twenty s, I was maybe a little fearful of that path because I saw how much trust in work it was. So that’s why I went into consulting. 

Alex Zekoff
I think it was a safer path. But as I gravitated more towards that calling of wanting to be an entrepreneur, my dad always was in my ear, saying, alex, when are you going to start your own company? When are you going to get out of the corporate grind? And I appreciate that he kept on it, and I did take the plunge. And so for me, my dad has always been the guy I look up to in that sense and just taking the chance, because again, he had no business skills and he learned how to create a business and sell it. And that at least gave me the hope that I have not created a multi billion dollar unicorn SaaS tech company, but as long as I can believe in myself and my skills, I’ll just keep pushing and driving and innovating along the way. 

Brett
What about books and the way we like to frame this? We got this from Ryan Holiday. 

Alex Zekoff
He calls them quake books. 

Brett
So a quick book is a book that rocks you to your core, really influences how you think about the world. 

Alex Zekoff
And how you approach life. Do any quake books come to mind moonwalking with Einstein? I read that book 15 years ago. The premise of the book is around memory competitions and how the people that memorize PI up to thousands of digits do it, using these concepts called memory palaces. It also highlighted a concept of time perception, and that when we create more novel experiences in our life, the perception of our life is longer. And so once I read that, I took a real, basically decisive path to create novelty in my twenty s of experience of my network, of traveling and experiencing as much as I could. And that really just shaped how I think about life. I’m chasing the experience, the learning, like slowing it down. 

Alex Zekoff
And so that book has really helped me think about memory from our own human perspective and our own cognition, and helped me form my own strategy for living a meaningful, fulfilling life. 

Brett
What does a meaningful and fulfilling life mean for you? 

Alex Zekoff
As I kind of mentioned a little bit earlier, just looking back and having no regrets that I built the story or a narrative that if I read my own autobiography or biography that I would be proud of. I think being the primary actor in your own play or in your narratives is important. And if there are things that intuitively I feel I need to be pursuing, leaning into that intuition and not going towards the easy path. So a fulfilling life to me is something that’s taking the challenging path, doing the working on the hard thing, focusing on multidecade outcomes, and not just the one or two year outcomes. So fulfillment to me is developing a masterpiece, if you will. If you think about this in the artist context of a masterpiece might take decades to develop. 

Alex Zekoff
But knowing that when you get to the end of developing that masterpiece, you’re really proud of the work, the outcome, the impact you’ve had industry like healthcare, that we’re focused in right now. So that’s fulfillment for me. And then fulfillment also lies in my personal relationships, so strong relationships with my family, my close friends, my wife. That’s number one. Without that, any monetary or career legacy would mean nothing if I couldn’t master my personal relationships. 

Brett
You come across here as very wise, very mindful. Have you always been that way? Take us back to Alex at age 20. Would you have been saying the same things or all these things that you’ve learned over the last 1015 years? 

Alex Zekoff
Yeah. Alex, age 20, was still very much not in his wisdom path yet. Definitely going through the college phase, growing up, figuring stuff out. I started more personal self development and growth in my mid to late 20s, probably when I got to California, and really started wanting to be a better human, just generally wanting to understand my own psychology. I think the principles that I’ve learned have come from my mom. My mom is a very wise person, very methodical, very patient. I think she gave me maybe the core skills of wisdom, but I think wisdom is an investment in our own consciousness, being aware of how we are coming off, how we’re investing into others, how we’re not projecting our own insecurities. I would say in the last seven to eight years, I’ve been really invested into personal self development and growth. 

Alex Zekoff
My wife actually is one of my executive coaches. I have three executive coaches right now in different facets of my life, and she is one of the most mindful, conscious, deliberate, loving people I’ve ever interacted. And she is, from a wise perspective, much more advanced than me. So I’m still trying to get on her level, a Jedi knight status, but she has opened that door of conscious communication, understanding, self reflection, and internal awareness. That has definitely been the last six to eight years. It’s been more of my focus in that area. 

Brett
You’re going to win some major points here when she listens to this episode as well. 

Alex Zekoff
Yeah, I hope so. Definitely helps. 

Brett
What personal skill are you working to develop right now? I’m sure there’s a bunch of different things that you’re working on, but if you had to choose, like, one big thing that you’re really working on improving, what is it? 

Alex Zekoff
Right now, I am acting CEO, but my two other roles right now at the company are CRO and CFO. I am really working on becoming a great chief revenue officer, a great salesperson, creating a great go to market playbook, how to close deals. So I am obsessed with learning offers and contracts and how to get customers to really love what you purchase. So I’m really focused on buyer experience right now. I listen to a lot of podcasters, like Alex Hormozi for example, is a leader of mine in the sales and marketing space. But I love his content. I love listening to how to go get the deal done in a way that has high integrity actually from his work and creating slots of what he calls it. 

Alex Zekoff
We’ve actually implemented slots of the company where we only sell one new customer a month and that’s helped us drive up prices, demand, all of that. And that was from him. So I’ve been implementing that. So I’ve really been working on a sales go to market motion and becoming a master in that domain. 

Brett
Have you read his new book? 

Alex Zekoff
I’m halfway through it. It’s amazing. My Co-Founder, Dan Parsons, who is also our chief marketing officer, they came out and were right on it. So 100 million dollar offers was amazing. 100 million dollar leads has also been great. So right now, actually, from his lead magnet chapter, we’re really focusing on our lead magnets right now. 

Brett
Nice. Yeah. I read that first book that came out last year. I listened to it on audible, I should say. And it’s such a great book. I love Alex Ramosi. I think he’s so entertaining and fun to watch. 

Alex Zekoff
Yeah. And he’s also just doesn’t care in a good way, like what people think of know he has the beard, the big beard, he wears the tank top. He’s just like, that’s me. And I love how authentic he is. And it’s awesome that he is leading a new generation of entrepreneurs, especially on the sales and marketing front, which sometimes doesn’t get the love that maybe product and r and D does. So exciting that he’s like being a leader in that space. 

Brett
I was watching one of his interviews and he talked about how his initial plan for life was to be, I think he called it rich and anonymous. And now he’s made that switch to really put himself out there and he’s a very public figure. Obviously we’re talking about him here, so he’s out there. You put yourself out there like that. 

Alex Zekoff
Yeah. I still think I’m on the rich and anonymous side. I think one day I might flip. I think maybe it’s when I get to that level where I feel like I’ve achieved enough success. I think hormosi actually talks about this is like it’s kind of never enough. And so when do I feel like I’ve achieved enough success to start sharing? I think right now we’re just so heads down in building that I don’t even have enough time to give it my best at creating a pod or creating content. One day I think that will flip. I have a relentless focus on us getting to a billion dollars in ARR, so I think once I can pull my head up and maybe see around, then I’d love to share how we got there. Kudos to Armozi for doing it live while he’s building it. 

Alex Zekoff
I think I’m just so obsessed and focused and all in right now on this thing that I wouldn’t give it the proper time it needed to give it. I know myself, I’m obsessed with things when I get into them. So if I got into it would take time away from sales and r and D and all that. So I hope one day I move to the public Persona. But yeah, right now, still in the rich and anonymous camp. 

Brett
Yeah. And I think he didn’t do that anyways either until after he had his big exit. Right. I think some of those early interviews I watched with him, he was saying, just google my name and you’ll see. A private equity firm bought my company. It was already out there. So he wasn’t in that day to day grind on at least the first thing at that point. So that makes sense what you’re saying as well. I think it’d be very difficult to do that as you’re in the middle of building a company. 

Alex Zekoff
Billion dollars ARR. Yeah, exactly. 

Brett
This show is brought to you by Front Lines Media, a podcast production studio that helps B2B founders launch, manage, and grow their own podcast. Now, if you’re a founder, you may be thinking, I don’t have time to host a podcast. I’ve got a company to build. Well, that’s exactly what we’ve built our service to do. You show up and host, and we handle literally everything else. To set up a call to discuss launching your own podcast, visit frontlines.io podcast. Now back today’s episode. Let’s switch gears and let’s dive deeper into the company. How we like to start this part of the interview is let’s focus on the problem. 

Alex Zekoff
What problem do you solve? We help mid market healthcare providers get paid all of their money faster. And when I say all their money is they submit claims to payers, insurance companies, Medicaid and they are only collecting 65. That’s common. We use our software robots as augmented revenue cycle employees, healthcare workers. We train those revenue cycle employees how to use these workers and so they can ten x their throughput, less mistakes. And we help those companies collect 95%. We help increase their day sales outstanding from 50 days to five days. And so we’re really solving a cash flow problem in the healthcare industry using our AI solutions. And so what does that all mean? More cash in those healthcare providers banks means better patient experiences. They can invest more in doctors to spend more time with the patients. 

Alex Zekoff
It’s a better outcome for the US healthcare industry. So we believe we are fundamentally attacking the US healthcare cost problem from its root cause, which is healthcare administration, which has notoriously been expensive, a bloat in healthcare providers, and something they don’t want to do. They don’t want to run systems and process. They want to serve patients. So that’s the problem we’re going after and the problem we’re solving with our aipowered solutions. 

Brett
And how do you uncover this problem? Is your Co-Founder a doctor? Do they work at healthcare for 20 years? When you were at Deloitte, were you working with a lot of healthcare companies? How’d you uncover this problem and even. 

Alex Zekoff
Know it exists by accident is the truth. I worked in aerospace and defense for my first ten years. So heavy manufacturing, so not healthcare. I did learn RPA. I did learn really great solutions while I was there. And so when we first started the model we created, were a notorious amazing solution, but didn’t really have a problem set that was compelling for it. We had a great model, great solution. So we started deploying our software robots in 2020, and we just lucked into mid market healthcare. That was our first customer that happened to be now, fast forward today. Last year, went through this thing because in the first two years, were selling bots to everyone. I think every founder kind of goes through this where they kind of want to go too wide, too fast, too many skus. 

Alex Zekoff
We were selling legal robots, real estate robots, manufacturing robots, and weren’t developing an expertise of what is really the KPIs that these robots are moving, that our buyers care about. So last year, we looked at all of our robots. We had about 85 live robots in production systems across our 35 customers. And we looked at all the data and we’re trying to figure out where is product market fit, like, which one of our robot segments are the highest ROI. We looked under the hood and all of our mid market healthcare companies, the robots were 1000% rois. They were spending 200% net revenue retention. And so by actually just using data of our existing fleet of robots, we found product market fit. We pivoted to just go mid market healthcare and we’ve been off to the races this year. 

Alex Zekoff
It’s been an awesome experience to actually experience product market fit. Our first version of product market fit was just selling a lot of robots and industries, and that felt like a demand wave. But then we sold out last year a little bit because we didn’t know how to repeat that story to the same buyer over and over. And so this last six months, we’ve really been focused on our robots augmenting healthcare workers, human healthcare workers, so you can turbocharge them to ten x their throughput. We sell right to executive teams who are looking to transform their companies and inject AI and automation. And we come from a very different approach. I like to call this transformation company. And that’s because we decided the hardest part of buying tech is that you typically have to have an internal team. 

Alex Zekoff
You have to buy an implementer, maybe like a deloitte, and then the technology licenses. We are all three of those things. So we are your internal team, we are your implementer, and we are your technology. And that means the price is one price. So when you buy us, it’s very easy to model ROI. And then we tie our outcomes to objectives that executives care about. Executives in healthcare, they care about cash flow, they care about collecting more money. And so we actually tie our contracts to success of those outcomes. And that has helped us really speak the same language that our healthcare providers are speaking. 

Brett
A while back, I was watching a Bill Ackman interview, and he mentioned a book that he liked called the Outsiders. And I bought it and read it. And it basically dives deep into, I think it’s eight ceos who were industry outsiders. They hadn’t come from the space they came in as CEO, and they’ve just dominated the field. Do you view yourself then as an outsider, and do you view that as an advantage? 

Alex Zekoff
Yes, absolutely. In healthcare. And I love it because I have no preconceived notions in healthcare of how it’s supposed to be done. So I come with a beginner’s mindset every day. First principles of what’s the core problem here, and how are we solving it best for the customer experience? Thinking about how Jeff Bezos built Amazon, it was always the customer obsession over the customer. And so with our healthcare customers, we really are diving in, and we care about the problem. Our customers. If you talk to any of them, they will tell you that we care. We show up, we fly on site, we meet with the executive team. We want to understand what their biggest pain points are and then we help solve those pain points. So we are your partner to deploy AI across your business. 

Alex Zekoff
And because we’re outsiders, we come at it with fresh eyes and they can feel that energy that we’re actually excited to come at this problem in a new way and get the outcomes they want in the process. So I 100% agree. Outsiders is sometimes the best way to get to the next version. The version two, the innovation. 

Brett
When I was looking at your website the other day, I did notice just how clean and crisp the messaging is and just really how good the branding is. Did it start off that way? Has the message always been this clear? Has the branding always been this dialed in? Or was it a journey to really get to this point? 

Alex Zekoff
Probably 100 version journey of our website. If I would have showed you our website two years ago, you would laugh. There was a lot of ego in our website. It was a solutions focused website saying, I think were testing the tagline, our bots are better, faster, smarter, which doesn’t really mean anything to anyone. It just is talking about our technical solution, which our bots are better, faster, smarter. But that doesn’t really resonate with people who don’t understand what bots are. So we’ve really been working on the website to speak to the market and really trying to dial in message, market fit. And this last six months we’ve iterated extremely fast using tools, large language models like chap, CBT and mid journey. We’ve been able to go from 100 page website to I think we have over 3500 content pages on our site. 

Alex Zekoff
So we’re really trying to serve with more content, more better messaging and make this as simple as possible because diving into AI and automation can be scary, especially with the plethora of tools that are out there. So we are trying to make this as simple and elegant as possible for our healthcare providers. So thank you for that. We’ve been working on that for the last two years and it’s been a journey. 

Brett
How do you separate from all the. 

Alex Zekoff
Noise that’s out there? 

Brett
Obviously, AI is everywhere, especially after what, November when chat GBT really got released into the world. So how do you separate from all that noise? How do you make sure that your customers know that your AI is different from the thousand other companies that are also using AI as well, or say. 

Alex Zekoff
They’Re using AI as well? It’s a challenge. And that’s why we’ve been very intentional with marketing ourselves as not a tool, but a full experience. Every account that launches with us has an eight person team assigned to them for the first year. That touch is so unique in the market, like coming to a customer and just really having that level of white glove service is a differentiator. That’s why we’re only selling one customer a month. That’s our capacity right now. And we tell our customers we’re committed to quality and excellence, not just pushing seats, pushing pools. Which is unique in the market is we are not a tech tool that you have to fit your process in. We inject the automation AI in your process so it’s all custom delivered. And so our buyers love that. They love that. 

Alex Zekoff
We’re not asking them to put up a new system and put data somewhere. We work on top of their existing tech stack. We deploy the robots, and we’re kind of building this layer of the system of intelligence on top of their systems of record, where we’re speeding up their throughput, and we’re putting one console where they can really operate these different software robots across different departments and see a data view of their company that is unique and hasn’t really been built yet. So by building custom, we’re able to actually one hit the customers needs because the process usually is their process, and they don’t want to have to change their process to fit into a new box of technology. And I’ve seen that since I was 22 years old. Deploying SAP out of the box. 

Alex Zekoff
You go to any Fortune 500 enterprise install, it’s now just become a custom ERP system, not SAP out of the box. So this persists across most companies. So they love the white glove service, they love the custom nature, and they love that we tie contracts to outcomes. So it’s not just, hey, I’m going to pay this fee and then do I actually get the thing? The ROI that you promised in the sales pitch, we actually have clauses state that you don’t have to pay us until we achieve those outcomes. So those three things are differentiators in the market that are helping drive our growth right now. 

Brett
Are you going to be able to maintain that level of white glove service as you scale to a billion dollars in annual revenue? 

Alex Zekoff
So we think about this, we believe, yes. And how we’re going to do that is we’re investing more into R and D to close that gap. So if right now we can launch one customer at an excellent customer satisfaction score, per month. Our question next year is, how are we going to launch one per week? Just like SpaceX could launch one rocket per month, how do they be able to launch multiple rockets per day? And we think a lot of this is just, again, more innovation, r and D, more AI powered tools internally that help us scale. We actually believe we have a strategy. The company is 100 million ARR, 100 customers, 100 employees. And so we are investing so much internally with AI tooling to be able to make that happen. 

Alex Zekoff
And we believe we can scale to four launches per month next year. And again, our contracts are not small by any means. We do have a pretty large ticket size, but with that comes exceptional outcomes tied to ROI. Typically, a customer will pay us back our fees in four to five and a half months, and then they’re in the profit zone. So because of that, we believe getting to 100 million ARR, 100 customers, we can achieve that by 2026. And so we’re kind of just on that dedicated path. We’re also working to be cash flow positive. We want to be a company that actually spit off profits, and we believe in the world of AI, that needing less human labor will mean that companies become profitable quicker. And so it will change the whole thesis of how we build companies going forward. 

Brett
What keeps you up at night right now? 

Alex Zekoff
Great question. To be honest, I try to leave it all in the field every day. So if there’s ever a conversation that I didn’t have that day with an employee or my Co-Founder or an executive, that will keep me up at night, because I know I needed to have that conversation and we needed to have that communication. So I try to leave every day with having those conversations to make sure I’m not leaving any. If I’m feeling resentment or any anger, I don’t want to leave that internal inside of me. So I will work to have those conversations as quickly as possible. Right now, I’ve been pretty good at that. 

Alex Zekoff
So I typically sleep pretty well at night, but there’s days where I can’t get to those conversations as quickly as I can, and those can keep me up for a couple of nights until I have them. 

Brett
You said something earlier in the interview I want to ask about as well, and that was, I think you said, three executive coaches. So you have an entourage with you. The impact and what value have you gotten from executive coaches and why do you need three? I guess would be another question, like, do they have different functions, different areas they’re focusing on, or what’s the deal with the team? 

Alex Zekoff
So one of our coaches is my Co-Founder. He is a CEO coach and were very fortunate. He’s working with us sort of on a, we’re not paying his full retail rate. He advises Fortune 500 ceos. He even advised Steve Jobs at one point. The way he brings data to the coaching, we take all of his diagnostics and tests and he compares us to his entire leadership database is an amazing insight into how we compare to other ceos in Fortune 500 companies. And then we put plans to close the gaps. So that’s just like an awesome data driven CEO coach that my Co-Founder and I utilize. My next coach, I meet with her every two weeks, not my wife yet. This coach is really focused on the empowered self. 

Alex Zekoff
So me coming in kind of that, manifesting that vision for how big we want the company to be. If I’m ever feeling fear in a decision, helping me move through the fear to make the decision quicker, and understanding where maybe the trauma is or where I’m getting blocked. And then my wife, my first executive coach, she is just such an amazing insight on deals and intuition and helping me understand nuances in the company that I can’t see. She’s kind of my blind spot checkered coach and whenever she’s bringing something up, I need to address it because she is very accurate and she’s really helped me see things that I was missing. So across those three, they kind of formed this robust crew that helps me in different facets of my career. 

Brett
I mentioned there in the intro, you’ve raised 21 million to date. What have you learned about fundraising throughout this process? 

Alex Zekoff
It’s hard in the beginning. It gets easier as you have people back you. I’ve learned to always be honest. If you’re not doing well, the company, tell your investor if you’re doing well, don’t overhype it, just be really accurate. And I think investors really love founders who expose the weak spots of their business. And right now we have a lot of investors that are really excited for our next fundraising milestone inbound. And I try to share with them that it has been a journey. We did have to let go of negative gross margin accounts. We did that strategically so we could be more profitable growth. Just not trying to sugarcoat where the business is, exposing where the risks are, what the real opportunity is. 

Alex Zekoff
That’s really been my experience the last three and a half years as I’ve raised money, is to just be honest and just be truthful where the business is. And sometimes as founders, we want to sell our own narrative too. Much we believe in our own narrative. It’s always good to detach for me from the business and observe it from a third party and think about, if I was an investor, would I want to invest in this business? If I knew that this thing was happening in the business, and then it helps me be a better leader and ceos, then I can come from a very detached place when I make decisions. 

Brett
Let’s imagine you were starting the company. 

Alex Zekoff
Again today from scratch. 

Brett
Based on everything you’ve learned so far, what would be the number one piece of advice that you’d give to yourself? 

Alex Zekoff
Great question. You can go faster than you think. I think looking now, what’s changed is my pace of execution, how fast I make decisions, how fast I move. So that’s been one thing is you can go faster than you think in achieving anything. And then two, I would say, is really slow the hiring process down. Like the early employees need to be. We call our employees warriors discipline. We have all these characteristics, but really just people who are so aligned. You say one sense they get it and there’s high integrity. That thing is going to get done probably before you needed it to get done. That level of connectivity early is so important. And slowing down to speed up really makes sense when you’re hiring employees that want to be building a company with you for a year. 

Alex Zekoff
So those are two things that I think I’ve experienced in real life of going through the journey. But now I would definitely say I can always go faster. I’m always challenging myself to go faster in our team and go slower to hire. 

Brett
Final question before we wrap up here, let’s zoom out three to five years into the future. What’s the big picture vision that you’re building? 

Alex Zekoff
We are really excited about healthcare. As I mentioned, we believe it could be a $1 billion ARR franchise. We have built the technology to be horizontal. We can automate anything in the world. We can replicate a human workflow, any system, any process in three months. We do believe that after a blockbuster, we might ipo with healthcare. But after that, we do have ambitions to go into government in Fortune 500 as different categories where we could play with our platform. Healthcare is such an amazing first blockbuster hit that we really want to focus and nail it. And so billion ar and healthcare, that’s just getting started for us, that’s sort of like maybe YPO just in healthcare and then post ipo, we would think about other sectors for us, too. 

Alex Zekoff
We realize that innovation is happening at a much faster rate, as we’ve seen with large language models coming out, there’s new tools and new ideas and things are coming at rapid pace. So we need to stay ahead of the curve. We think this is our first act. Our software robots are amazing at collecting meta process data and training data. And so we actually believe all the data, the metadata we’re collecting on processes will create really innovative large process models that are going to be really interesting to sell as a new product and service in five to six years. So we’re already thinking about that and how can we, even if we have to disrupt ourselves, how are we going to make sure we’re ahead of the curve? Always. 

Alex Zekoff
So investing more into r and D is a primary focus right now as we think about looking around the curve for what’s next, especially in AI, as the pace is picking up quicker than anticipated. Amazing. 

Brett
I love the vision and I love the approach you’re taking to building the company. Alex. We are up on time, so we’ll have to wrap here before we do, if any founders listening in want to follow along with your journey. Where should they go? 

Alex Zekoff
Thoughtful AI is our website. We’ve got a lot of stuff there around the company, what we sell and all that. I say that’s where you can find most of the contact information, all of that. If you want to follow me, I’m on LinkedIn. Alex Zeekoff, you can follow the company there too. Thoughtful AI. We’re excited. Like you saw on our website, we are building more content so we’ll be getting more involved in social media. Even my co buyer. I think about starting a podcast as well, so we might have to talk to you, Bret, the trade here, how to get going on podcasts. But come find us, come talk to us and would love to chat. Awesome. 

Brett
Alex, thanks so much for taking the time. I really enjoyed the conversation. 

Alex Zekoff
Same here. Thanks, Brett. 

Brett
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