Many entrepreneurs dream of scaling a niche product, achieving market dominance, and ultimately securing a successful exit—but few actually make it happen. How do you take an idea from concept to acquisition, and what key lessons can other business leaders, including marketers, take from that journey?
Joining me today is Chris Tilkov, General Manager at DocuSketch, an automated estimation and documentation platform that helps homeowners rebuild after natural disasters. Before joining DocuSketch, Chris founded AskAiME, a platform that was successfully acquired. But his journey didn’t start in tech—he began his career as a carpet cleaner before transitioning into the world of technology and entrepreneurship.
About Chris Tilkov
Chris Tilkov is a director at DocuSketch and is the founder of AskAime, an InsurTech that simplifies estimating and quality assurance for the insurance restoration industry to settle claims quickly and accurately. With over 25 years’ experience from flood technician to nationally held positions, Chris works with companies to provide the training and education needed to produce fair and consistent estimates through collaborative technology. In 2023, DocuSketch acquired Aime Estimate Review Inc. Chris Tilkov on LinkedIn: https://www.linkedin.com/in/chris-tilkov-a5038b3b/
Resources
Docusketch: https://www.docusketch.com/
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Transcript
Greg Kihlstrom (00:34)
Many entrepreneurs dream of scaling a niche product, achieving market dominance, and ultimately securing a successful exit. I’m going to just start that over again. Many entrepreneurs dream of scaling a niche product, achieving market dominance, and ultimately securing a successful exit, but few actually make it happen. How do you take an idea from concept to acquisition, and what key lessons can other business leaders, including marketers, take from that journey?
Joining me today is Chris Tilkov, General Manager at DocuSketch, an automated estimation and documentation platform that helps homeowners rebuild after natural disasters. Before joining DocuSketch, Chris founded Ask AiME a platform that was successfully acquired. But his journey didn’t start in tech. He began his career as a carpet cleaner before transitioning into the world of technology and entrepreneurship. Chris, welcome to the show.
Chris Tilkov (01:28)
Thank you for having me, Greg.
Greg Kihlstrom (01:29)
Yeah, looking forward to talking about all this with you. Before we dive in though, why don’t you give us a little more background on how your journey from carpet cleaning to technology led you where you are today.
Chris Tilkov (01:41)
Sure, yeah. Somehow I’m a started in this industry, restoration and insurance when I was 17 and I’m a millennial. I don’t think you’ll find too many millennials out there that stayed in the same industry so long. I was a flood technician at first and a carpet cleaner. So a flood tech would be somebody that comes to your house or business anytime day and night when if you had a flood. So I learned a lot about building science and materials to demolition. At the same time, through my career, I was often studying part time and
What I was learning, studying mirrored what I was doing in the field. So I studied architecture and engineering. I studied business and ultimately onto technology. Created some set successful products for the companies that I worked for along the way, tied into ERP solutions and came up with sales reporting for one company that fundamentally changed the way they did business. And moved on to build a national estimating platform for a franchise group.
I eventually kind of really wanted to try something on my own. So that’s when I stepped out and, uh, put my efforts into AiME which is an automated review platform, reviewing insurance based estimates. Um, and you know, the long short highs and lows strikes and gutters on that journey as any entrepreneur has, um, but ended well. And I’m now part of DocuSketch and DocuSketch, um, captures 360 images at the beginning of the job for the insurance industry.
We write the estimate and use my product to review those estimates. So very natural fit and no looking back and no regrets.
Greg Kihlstrom (03:15)
Yeah. Love it. Love it. So yeah, let’s maybe, maybe take a step back and start, start towards the beginning here. And, you know, I want to talk about building and scaling the, product with which, you know, certainly fills a, an important niche there. So, you know, what inspired you to launch Ask AiME and, and how did you identify the market needs?
Chris Tilkov (03:38)
Yeah. Well, first off, I kind of mentioned I had a couple Identifying Market Needs and Launching Ask AiME successes for others and I really did want to try something on my own. I actually pitched the idea of AiME to one of my employers and it just wasn’t for them. They weren’t looking to get into the tech space. So fair enough. And I kind of assessed and realized that I was at a time in my life that I could take the risk. And so before what inspired that you kind of sometimes have to do a self assessment if you are really trying going the bootstrap method, like I did to really assess things. So I was single, no dependence. It was the time for me. this was the only industry that I knew and I specialize in reviewing estimates. It’s very time consuming to do that. You’ve got somebody on the restoration contractors kind of side of the negotiation doing it. You’ve got groups on the carrier side of the negotiation doing that. They’re not enough people. There were not enough experts and it was a terribly inefficient pro pro process. So that was the need.
I was confident from my experience and having becoming an expert, traveling, being a trainer, really knowing these systems inside and out that you, that I could design a system that could, parse these out and, and help in the process. it was definitely a leap of faith. you couldn’t test a small partial product here. You had to kind of build enough rules behind it so that it actually produced a result.
But it like I say, was the time in my life to go out and really try to do. So I saw a pretty significant need to improve efficiencies across the industry.
Greg Kihlstrom (05:08)
Yeah. And so, mean, in that stuff, I, know, there’s, different kinds of founders. There’s, know, there’s, there’s the technical founders that are, you know, they’re, writing code, but may not have as much of the hands-on experience that you had. So in other words, you’re, you’re coming at this from like the, market need was something that you experienced and the data for lack of a better way of explaining it was, was firsthand.
knowledge, right? Is that did you have other data that was kind of guiding your your decisions there as well?
Chris Tilkov (05:39)
Eventually, I mean, that became helpful when the company grew, we were able to empirically show both time savings and value change in the estimate to make it both more compliant and more accurate. For the personal experience, yeah, every single estimate is meticulously reviewed and there was very little automation out there. It did
quickly become data-driven when you do have that empirical value coming. Like today, for example, as part of DocuSketch at the scale we’re doing, we’re reviewing billions of dollars in estimates value. And each estimate on average, there’s big ones and small ones, but on average we’ll move hundreds of dollars to add additional items in that are warranted work that somebody is really gonna be doing in somebody’s home or business. And it also will move hundreds of dollars in the…
to reduce it for compliance, overages or mistakes. So we’re really bringing the two sides. I don’t want to put them on as adversaries, but they’re negotiating. We’re really trying to get them to a reviewed and approved estimate quicker with improved cycle times through the use of our combined product, AiME and DocuSketch.
Yeah. Yeah. And so, you know, this product, obviously very valuable and time saving for this industry, but, know, it fills a niche. so, you know, it’s not necessarily something, you know, consumers aren’t going out looking for this. So, you know, when you look at scaling a product like this, and when you look at the competition in the space, you know, how do you, you know, what were some of the biggest challenges that you had in gaining traction and, you know, what
What methods, organic growth, partnerships, paid marketing, what methods were used to really scale it?
Chris Tilkov (07:30)
Yeah, I am the tech more on the technical side. So I spent a lot of time on product. It had to be right. And I believe that, yeah, you had to have enough rules in this thing to make it presentable to somebody. And they had to be accurate. We’re helping people settle, like we’re commenting on an estimate to assist them to sell a claim. So it had to be right. And for sales,
I really ended up leaning on my reputation in the very beginning. So, the product was first kind of built on the shoulders of my reputation. I traveled a lot. I provided training for both restoration contractors and insurers. I was known for speaking at conferences, et cetera. and now far and away, the biggest users of, of AiME are actually DocuSketch internally. So it’s kind of like an internal customer is the acquire the value proposition that we’ve created together from initial documentation to estimating a review and has have a scale together. we combining those products for a greater one for our common clients now has been a huge catalyst. We’re doing, you know, many times over the volume that AiME was doing by itself.
Greg Kihlstrom (08:41)
Yeah, yeah. And so, you know, certainly there’s, there’s that, the deep technical knowledge, you know, both technical from a code perspective, but also technical knowledge of what’s needed for the, for the business to make a compelling product. You know, that’s certainly a key part. What about branding and storytelling and some of those marketing things? Like how, how much of a role did that help as, as you were going to market and scaling?
Chris Tilkov (09:08)
Yeah. So, yeah, the brand, like I kind of mentioned the brand at first, at least stood on the shoulders of my reputation, but for storytelling, maybe I can tell a, a story here. So how I ended up at DocuSketch, a big part of it was, through, through somebody I knew. So, I grew up in this industry, as we said, I eventually was leading an estimating department and a national franchise group estimating department. when problems with some of the estimates.
occurred, they kind of go uphill to a certain point to me and Nelson Higgins, who works at DocuSketch now as well, was in the same position but on the carrier side. So he ran the review teams and great guy, but we had to figure things out together. So reputation being what it is, when things got to us, we always knew that we could look each other in the eye get to the bottom of things, know, somebody wasn’t going to like it at the end of the day, usually me, because I was the contractor and they were paying the bills. But we’d come to like a amenable ⁓ agreement on things. And where these things can often be seen as adversarial and negotiating all the time with the same people. He was eventually who introduced me to DocuSketch. His company, he eventually stepped out and was creating an estimating product.
That’s now DocuSketch estimating. They acquired his company and I was introduced and made, you know, becoming part of the product at the very same time. So branding in this case was very much me. I was told by competitors in the industry that were, you know, as they were coming up that, you know, when we, when we say, ⁓ we’re, trying to figure out if, they’re looking at any other products, they’ll hear my name as often as they’ll hear the product, they’ll say, you’re working with Tilkov versus, we’re working with AiME. So it was very apparent that it was kind of one in the same. I was really transitioning a lot of my knowledge to a database is a lot of what the product was. I’m learning more from all the experts around the industry and combining it. But yeah, reputation was huge for the brand in this particular case.
Greg Kihlstrom (11:05)
Yeah, yeah. you know, it sounds like, you know, and I’ve been through the acquisition process before as well. And, you know, there’s obviously there’s opportunities that line up. you know, knowing the right people and your reputation, all those things are a key component of it. But there’s also a mindset shift. You know, there are some people that have all those opportunities and they’re like, no, I’m going to go it alone and and and all that. You know, what at what point did you like kind of make that mindset shift and say, okay, this, you know, an acquisition is the right move and you know, or was it always part of the strategy?
Chris Tilkov (11:39)
I’d say it was always a want of the strategy. had some early investors earlier on and I learned a lot from that experience. I had to buy them out to own 100 % again. It was just not the right fit from best I could tell they wanted to use it for their own internal purposes. Then there were some tire kickers and I didn’t really want AiME the product to end up with any one company just like the investors that were involved in being that used it for one purpose. So AiME’s a very unbiased attempts to be unbiased down the middle helps settle quicker, not going to add too much for a contractor, not going to take too much out for a carrier, but just have like, let’s bring the industry resources together. So I didn’t want it to land with a group that just wanted to use it for one purpose. So, so I knew that about the product, but I wasn’t going to sell out. All right.
Maybe one day I would have had to sell out, it certainly wasn’t part of plan. so I wanted the right bit. And when DocuSketch came along and I understood the prior, was aware of their product, 360 image. It’s kind of the source of truth for a claim and documentation around that. that’s where AiME fits as well. We just want to get to the right number, be truthful, honest, put it all right in front of everybody and help, speed up the touch points on the claim, speed up the cycle time.
I get to reviewed and approved quicker. So that was the right company at the right time. mean, it was quite, by the time it was acquired, it was quite profitable. I’d gone through the tough times, which were very real. It was quite profitable. So I would have loved to have cruised along a few more years at the profitable time. If that’s the peak, I don’t know. I don’t know. You can never know what would happen if you kept on going the other way. make the choice.
Chris Tilkov (13:17)
And the last thing for the acquisition was the timing was right. mean, just like I said, the timing was right for me to go out and try to create a product and, you know, I could maybe afford to fail and take that risk. The acquisition timing ended up being quite kind of stressfully just within a couple of days of when my first born son came into this world. So it created quite the hectic time.
We tried to actually avoid that scenario. DocuSketch was great in adjusting timelines to try to accommodate, but ⁓ when DocuSketch ran two weeks late and my child came two weeks early, it created some intense time. So quite the week there in the end.
Greg Kihlstrom (14:00)
Yeah, so what were some of the lessons that you learned through that acquisition process that you might share with some other founders that are early on, let’s say?
Chris Tilkov (14:10)
Yeah, sure. What was very apparent and probably, a lot of people would jump to really quickly. It was like our books were well managed, ⁓ no significant items to clear up there. our pricing model was very simple and easy to understand. made sense. we didn’t have many options for our clients or exceptions, so we didn’t have to sift through, all sorts of scenarios. and I learned during that, like how valuable licensing was as a model. So how much investors like a licensing model. I didn’t necessarily strategically do that purposely. It was the model I picked for, you know, it just made sense to me. And you know what, I guess it was attractive to me as a business owner and that makes sense how it would be for investors. I mean, in hindsight to say that reliable recurring revenue is attractive to investors should be pretty obvious. ⁓ But how much that mattered was part of what drove a good valuation. Then lastly, knowing that the other founder out there ⁓ was going through the same process as me, it made the acquisition process quite simple knowing that somebody in my very similar position to me was already ahead in the process. I trusted that person and we’re already going to become part of DocuSketch.
we cleared hurdles pretty fast on a trust basis, which I don’t think, you should always be careful out there and I certainly was careful, but I think I was able to move along a little bit faster on that path with that knowledge.
Greg Kihlstrom (15:37)
Yeah, that’s great.
So, you know, obviously your, your knowledge and your experiences is really deep and, in, your industry to broaden it out, you know, I see a lot of applications myself to, other industries as well, but just curious from, from your perspective, you know, what lessons would you share with, with marketers, you know, across, across other industries that, as far as your approach to growth and customer acquisition.
Chris Tilkov (16:06)
Uh, other industries from a guy who’s been in it in the same industry since he was 17. Um, so I guess it remains to be seen for me. Um, what’s been interesting, uh, I I’ve learned a lot, uh, after becoming part of DocuSketch it was a much bigger company. It’s continued to grow and expand and serve our customer base. And, uh, so I’m learning a lot from how bigger organizations, um, operate. And I was from more like bricks and mortar.
Chris Tilkov (16:35)
going to the job site boots on the ground type industry too. pretty, pretty significant trends. Some days I might be saucer died at some of the knowledge and ideas that are going on around me. But how the DocuSketch organizes, assesses, prototypes, reports and everything has been interesting to see. And I know that my expertise contributes to DocuSketch. have so many boots on the ground type people from the past that really
drive our product. like we do rely on that. I think I’m going tangential to your original question, but we push, like we know that we have some of the best people in the industry that with from both the restoration contractor side, the insurance side and tech side now as well.
Working with these people every single day has been just a great privilege and I’m learning so much for them. So sorry I don’t have a big ⁓ gem to share there, but I’m learning a lot all the time from this change.
Greg Kihlstrom (17:29)
I’m sorry.
Well, Chris, thanks so much for joining today. One last question before we wrap up. I like to ask everybody here, what do do to stay agile in your role and how do you find a way to do it consistently?
Chris Tilkov (17:47)
Well, yeah, quick, quick story there is, some of the clients that actually come to AiME, this will relate to how I stay agile. I promise come to AiME, come to DocuSketch. They’re actually like the technicians or the project managers. They just try our product. They don’t go to the, they’re, you know, the owner or the operations per person. They see it, they see the value. And then after doing a few files, understanding it, there are introduction to the company.
And similarly, some of the biggest successes in my career have been not through asking, but by just doing. you know, go out, try a product, develops a prototype if you can, hire somebody without asking, be careful out there too. Don’t take these. This is what you should do right now. but basically always keep moving. And I hope that most of your listeners, are in positions where they can, especially if they’re creatives.
I hope you’re in positions where they can get out there and try new things. And if you are creative and you can, it might be worth looking for a position that allows you to do that thing. And for managers out there, foster an environment that encourages creativity and stay agile.
