In this video, Rachel Go chats with StartSure CEO and founder Tim DiPietro about some common points of confusion when it comes to inventory insurance. They also discuss what inventory insurance covers, who is responsible for insuring goods in the warehouse, and much more.
Transcript below.
Rachel Andrea Go: So, thank you, Tim, for joining me today. You have a long history in insurance. Can you tell me a little bit about how you got started?
Tim DiPietro: Thank you. Yeah, I’m excited to be here. Yeah, I’ve been in insurance for pretty much my whole career now — 20 years, which is crazy and sounds crazy every time I say that it’s been 20 years. It’s flown by. But yeah, I got into the business. My dad was actually an insurance broker, and [I] sort of followed his path into it.
[I] started off working at some of the larger insurance companies where we were actually assessing risk as underwriters, starting at The Hartford and then at Arch, and learned a lot about how policies are structured and about how insurance companies and underwriters think about, you know, understanding risk and creating policy forums to address various coverages. So, that was a good, you know, sort of first part of my career.
And then I moved over to the brokerage side after about eight years on the underwriting side, where I worked with companies of all sizes, ranging from start-ups through large, publicly traded companies, and it was really start-ups that I enjoyed working with most, which led me to launch StartSure.
All business owners have to deal with navigating what insurance they need, either to protect their business or to simply satisfy contractual requirements. And for no one did it seem more stressful than entrepreneurs that are already wearing a million different hats, that are typically more tech forward, and just want it to be a clean and easy digital experience that we would expect in today’s age, and insurance has typically been far from that. So, that’s my path which brought me here today.
Rachel Andrea Go: And was there any particular trigger moment or a time that really inspired the beginning of StartSure?
Tim DiPietro: Yeah, actually, it was when coworking was still pretty early, and I had some clients that were through my traditional brokerage role that—one of them was actually a coworking operator, and the operator came to me one day and said, “Hey, our lawyers were telling us that, you know, the members in our space need to have insurance and they’ve been trying to get it but, you know, they said that either they don’t have time for it, they don’t know where to go, and we just want to be a cool, easy place to work and it’s causing friction. You’ve been great by us; can we just send them to you?”
And I thought about it and, as a broker where you make money on commission, maybe it’s not, you know, worth my trade, but — you know, doing these smaller policies — but, you know, they were cool companies and it was interesting, and I thought, “How much work could it be?” And even someone that, you know, comes from the digital age and [is] trying to make things super easy, you know, I created a digital form and thought that [it would take] no more than a day or two to put these little policies in place.
But, because each one of these companies was doing something unique, it was causing questions and it was basically, you know, a four- to six-week process just because I’d, you know, oftentimes have these follow-up questions, and that entrepreneur had moved on to be doing something else and you’d have to reengage them. They weren’t necessarily the hardest questions but, in summary, it was a miserable experience for them and for me.
And so I went to go and look at online solutions and see what else existed to basically say, “You know, you should go and use one of these, because this isn’t working for us, you know, on either side.” And [I] found that, you know, while the first wave of InsureTax had digitized the traditional apps that—those InsureTax that were out there were more or less asking the same thing that I was doing — they’d put it on a website instead of a, you know, fillable PDF — but they were still giving the same errors at the end; while they were promising instant quotes, the end result was, “Hey, there’s something unique about your business. We need to hop on a call.”
So, that forced me to sort of put on my underwriting hat of, “What’s driving these additional questions? These are people sitting in an office and, like, they just want to check a box and get insurance; they’re not trying to get all this different, you know, protection,” and create our first insurance product back in 2020 that allows businesses and coworking spaces to literally check that box and get coverage in under 60 seconds.
And with the success of that, we looked at other areas where businesses are faced with some of their first contractual requirements and, you know, set off on our goal of creating StartSure to simplify how entrepreneurs get insurance and just making this as easy as possible to check the box for those first contractual requirements and then further protect, you know, all that they have worked hard to build and just making it easy to get, easy to understand, and that clean, digital experience that, you know, any one of us would expect today.
Rachel Andrea Go: And what lessons from your extensive experience in insurance helped you start and grow StartSure?
Tim DiPietro: You know, I think from that experience that I just highlighted — aside from, you know, when people would ask me at a party what I do, and I’d say insurance, and they’d roll their eyes and walk away, because anyone that had dealt with it knew that it was a painful, annoying experience — it was really as much as, you know, being, like, “God, yeah, insurance really does suck,” but it is an important thing that we all need to protect our businesses. We’re all working hard to build these things. It is a relatively little expense, and if you can make it easy — you know, that time expense obviously is important too — like, it’s a valuable tool to work all the—you know, to protect all that you’ve worked hard to build.
So, you know, I think it was as much of finding that first problem that I highlighted with the coworking spaces. It’s just being sick of people turning their backs on me at parties and networking events when I mentioned insurance, so.
Rachel Andrea Go: So, we’ve mentioned StartSure a couple times now, but could you tell us a little bit more about what exactly StartSure is and does?
Tim DiPietro: Yeah, so, StartSure is the solution to all those problems that I highlighted, right? Both for me personally as well as, more importantly, for our customers. We are a digital-enabled brokerage that combines really the best in class of technology and insurance expertise.
So, what I saw with—when I went to go and look with that coworking example that I gave earlier of this first wave of InsureTax that had digitized things, they were primarily a bunch of tech people that had bad experience in prior start-ups with getting insurance and thought, “Oh, we’ll digitize and make it easy.” But they didn’t really innovate on the product side, on creating new policy forms for the way today’s modern businesses work, and as a result, that’s why they couldn’t provide a better solution back then and where I saw the opportunity to create coworking and now to create our new solution with inventory insurance.
So, really trying to innovate as much on both the technology as well as on products, and then also pairing that with insurance professionals—experienced insurance professionals that can help guide these business owners to what they need because, while everyone wants that clean, digital experience — and we can give an experience to customers that is purely digital and they can purchase everything online without talking to anyone if they want — we find that, more often than not they’ve, got questions. And a lot of those questions are stemming from, you know, a contractual requirement that a client or vendor is asking of them, or a warehouse operator, or the coworking space. And, you know, they might have questions about what this coverage does or, you know, why they need it and maybe even what else we recommend.
We try to be very forward with also our recommendations of what other coverages they might need, not in a salesy way but, because 80% of our customers are first-time buyers, I feel like it’s as much about education as anything. You know, things like cyber liability — they’ve probably heard of them or DNL, but for them to understand what that does and why it’s important to them, I think is important.
So, we very much lead when we’re connecting with our customers with, “Hey, thanks for buying our inventory insurance,” or “Thanks for buying the working policy, but, hey, we see that you’ve created this cool digital platform. Your bigger exposure is if your website gets hacked or, you know, some technical glitch causes, you know, your system to go down and you’re losing revenue for a period of time. Like, that’s really your bigger exposure. You’ve satisfied your contractual requirement for the coworking or the warehouse, whatever it might be, but, like, let’s focus on that.” And because we’re bringing it to their attention of what that implication and impact could be on their business, you know, they more or less—more often than not engage, and then we can have a meaningful conversation and help them protect their business as opposed to just pushing a product. So, that’s really you know, sort of the core of what we’re doing at StartSure.
Rachel Andrea Go: So, I haven’t often seen coworking spaces and eCommerce inventory lumped into one sentence — at all, ever. So, can you tell me how you got into insurance for eCommerce inventory in particular, coming from the coworking side?
Tim DiPietro: Yeah, so, it was really, you know, looking at where else today’s modern businesses might face those first contractual requirements, seeing the pain point that we saw in coworking, and looking to where else that might be.
And, you know, I feel like it sounds a little corny, but I was listening to a Tim Ferriss podcast, and they were interviewing the founder of Shopify, and he was talking about, you know, all that Shopify was doing and the rise of the 3PL warehouse ecosystem that supports the, you know, the huge eCommerce boom that we saw, you know, supported by COVID and everything else. And that sort of thought of a light bulb off in my head of, “Oh, I wonder if these warehouses are requiring any kind of insurance?” And as I started reaching out to some of, you know, the 3PLs that I was able to, you know, get to in the beginning, [I] realized that they all do and that every one of them requires the merchants that are storing their goods in them to insure against things like fire and natural disaster and that, furthermore, that this was a thing that was really hard to get for these business owners. It wasn’t a quick, easy solution.
And with that light bulb going off, [it] led me down the way of, “All right, how do we replicate what we did with coworking insurance where we can literally let these people just check a box and take care of this under 60 seconds and set off on going out and finding an underwriting partner and carrier that can back it?” Because, you know, while I have the experience, you know, that I highlighted to be the insurance companies, it takes a lot of capital, and I don’t think that that’s the best place for start-ups to be, protecting all that they’ve worked hard with a start-up that doesn’t have secure capital. We wanted to make sure that we had large, multinational insurance companies that are backing us so that, in the event of a claim, that client’s getting paid.
So, it was as much a part of going and finding those good carrier partners. In our case, Arch insurance was the insurance company that backed our first coworking policy, and we brought the idea to them, and they were very excited about creating a solution for inventory as well. So, [it was] fortunate to have Arch as a carrier partner and the one that’s taking on the risk and really believing in what we’ve created here and creating new policy terms and supporting the whole flow.
Rachel Andrea Go: Is it mostly common for retailers to purchase their own insurance? Or, is it more common for warehouses to purchase insurance for their inventory that is in that warehouse? Or, is it common for brands to purchase insurance through their warehouse? Or, how does that usually work?
Tim DiPietro: Yeah, so, what we found is that it seems like it’s a very confusing process for brands in particular. When selecting a 3PL, you know, they’re trying to find the—not only the best place from a logistics standpoint of fulfilling all their orders and just, you know, something with clean tech and makes it all easy, but they also are looking for secure, safe warehouses, and as part of that process, you know, the assumption of a lot of brands, we found, is that the warehouse is responsible for ensuring their goods if something was to happen. And, while the warehouse is responsible if something goes wrong as a result of their negligence, right — if they forget to lock the door or forget to pay the heating bill and the pipes burst because it freezes or, you know, one of their employees is stealing — any kind of scenario like that where the warehouse is negligent, yes, they’re responsible. But anything that’s outside of their control, like a fire or earthquake or other natural disaster — that’s something every warehouse operator that we’ve spoken with so far requires of the brand.
And what has been interesting also is that, because this is such a young industry and a relatively immature industry, you know — it’s not only new, but everyone’s trying to figure it out and there’s so much competition in it — that, because insurance has traditionally been such a, you know—getting this inventory insurance in particular has been such a pain point, a lot of 3PLs, why they require it, might mention it in the initial onboarding. Sometimes they just skip over that requirement.
And, you know, the thought is that they don’t want to introduce friction that might lose the deal and have them go to another 3PL, which I totally get. But it is doing the customer a disservice in the end because, in the event of a loss, you know, it could be a real issue, not only because the customer’s now lost, you know, all they’ve worked hard to build and this very valuable inventory to their business, which could easily bankrupt it, but it could be a pretty bad PR moment for the 3PL as well, right? Because that customer might be like, “Well, you never told me I needed this,” or “You never enforced this requirement,” whatever it might be.
I mean, we were talking to a brand the other day that is doing $90 million in sales that has $10 million of inventory across three facilities, and they were just under the assumption that it was covered by the warehouse, and, you know, we said, “Look at the contract and talk to your warehouse operator, because, you know, we’re almost certain it’s not,” and it was a real, you know, “Oh, s***” moment, and fortunately, it wasn’t as a result of a claim, you know, it was a result of them getting put in touch with us on something. But had that been an event of a claim, it would have been a real issue.
So, to answer your question — I know that that sort of dragged on a little bit, but hopefully paints a good picture — it is the responsibility of the brand. At what point they get it, you know, we’re seeing a lot of variation in. Some of that variation comes down to that company and, you know, more often than not that founder’s risk tolerance. You’ve got some people that, you know, have a business background that might have dealt with insurance before that are very conservative that, you know, want to make sure that all that they’re doing is protected.
More often than not, there are younger entrepreneurs that are very ambitious, very smart, and very driven on top-line growth but not necessarily focused on insurance, largely because of a lack of understanding. And where we do see insurance coming into play before a brand might move into a 3PL and have a need for inventory insurance is largely around satisfying the contractual requirements of vendors or, you know, other operators like an Amazon, like a Walmart that, in order to do business with us, you need to have a certain amount of general liability and product liability. And sometimes these limits can be really high and expensive. You know, they might need a five-million-dollar umbrella sitting over the top for a business that’s generating half a million dollars’ revenue. Like, it’s a little inverted, but if you want to work with, you know, a Walmart, that’s what you need to have. And so brands obviously buy that because they want to, you know, get that contract.
As a result, they often are overlooking the need for inventory insurance, and that’s what’s really, you know, protecting them, more so than that the general liability. Yes, the general liability and product liability in particular is important because, if their product causes harm or damage to someone—so, if it’s a skincare product and it gives someone a rash or, you know, we see this a lot with lithium ion products, if that product has a, you know—catches fire, which has, unfortunately, been something that’s been in the news plenty, and causes damage to a building or, you know, a structure, like—that’s all general liability, and that’s a very important coverage to have to protect that company. But, if
If they’ve got a million dollars or, you know, more—whatever is a big number relative to, you know, their operations sitting in a warehouse, and that gets wiped out by a tornado or a fire or whatever and that’s gone, I mean, that’s the majority of the assets of that business, and it’s a real exposure that, once we’re able to get people to understand that, you know, the light bulb typically goes off and they want to get the coverage in place.
We do also have the ability to offer this solution through the 3PL warehouse. So, we are in talks with a few 3PLs that do have this very concern that I highlighted as well, and in being more proactive, they’re looking at buying this inventory insurance solution to purchase themselves as the warehouse operator and then offer to their customers and just sort of add it into their monthly bill.
One thing that I didn’t mention yet, but which I’m really proud of is, with both products — either the product that the customer can buy, you know, directly through our website or through a warehouse partner and this new blanket policy that we’re in talks with a few operators with — is that we’ve made it smart. So, aside from making it really easy to get that initial purchase, we’ve built Integrations right now with Shopify, Flexport, and some other WMS platforms that allow us to actively see the ebbs and flows of inventory, and our coverage then adjusts as their inventory ebbs and flows.
And this is important on two fronts, which, I think, are really solving for once again the way that today’s businesses work: One, a traditional broker putting a similar coverage in place would ask that brand, “Hey, what do you think your maximum inventory is going to be over the next 12 months?” So that, if there’s a fire at peak inventory, you’re protected, right? We want to make sure that, [in the] worst-case scenario, you’re protected. That’s, you know, the core of insurance.
It might be a hard sort of “crystal ball” scenario for that brand to say, “Oh, well, on our projections, we plan on this and, you know, we’re hedging it a little.” Whatever it might be, they pick a number, [and] that number could be too high, it could be too low, and say they have a really great year — I mean, they might have a value that they’re insured to for half or a quarter of what they ultimately have as an exposure. So, if you had that scenario where you had a claim at peak inventory, they could be underinsured there. And they’re not thinking, “Oh, I’ve got to go back and talk to my broker,” when they’re having a rocking year and, like, so focused on everything — like, that’s the last thing on their mind. So, that’s one.
But the thing that I think has been more exciting to the brand is—the reality is that you’re not at peak inventory for the majority of the year. If you’re a seasonal business, that peak could be a very short part of the year. So, you’re paying for more than you need for the majority of the time.
By our coverage adjusting on a monthly basis, you’re only paying for what you need. So, you get that upside protection of never having to worry about being underinsured. But what we’re seeing right now is, because we’re making it dynamic, that the savings on average is about 35% for a typical brand, and for the seasonal brands, you know, it can be upwards of 60%–70%. So, that can be very meaningful savings as, you know, we’re all looking to be as lean as possible and optimize spend and be smart about that. So, that’s another component of what we’re doing with inventory that we’re really excited about.
Rachel Andrea Go: That’s amazing. Actually, one of the things I was wondering was how do merchants ensure their rates are fair despite inventory fluctuations, and so that answers that perfectly. Sort of in line with this kind of price-and-fee question or this line of—this topic, how can merchants know what’s a fair price to pay for insurance?
Tim DiPietro: Yeah, so, you mentioned rate earlier, and, you know, you’ve got the two components of what goes into creating insurance premiums: You’ve got the rate — what is being charged per—on a per unit basis per dollar basis — and then the amount of inventory. The rate is going to be fluctuating between carriers and solutions. For us at StartSure, it’s driven by location and product type. So, for products that are basically higher risk of theft or damage — high-value luxury items, you know, that we are defining as over $750 per item, electronics—high-value electronics, things that are fragile — those will typically have higher rates than more standard goods like, you know, a t-shirt or something more benign. And then location. You know, typically, if it’s in a coastal location or somewhere that’s more prone to wildfire, that can drive rate as well.
The fluctuation and rates that we see between various carriers — it is—there’s not a ton of fluctuation. Obviously, you’re going to always have, you know, one solution that’s better than the other, and there’s competition amongst carriers on that, and some are better on certain product types and certain locations than others. But, in general, we see that our savings is coming from the dynamic component of what we’re doing. So, we have negotiated what we believe to be one of the most favorable rates in the market and we’ve seen that with the customers that we put in place, but the savings that we’re able to pass on to the customer comes from not insuring at the peak value for the full year. And so, yes, rate is important. But, you know, I think that component, which doesn’t exist elsewhere in the marketplace, is the thing that allows us to be the most competitive solution.
Rachel Andrea Go: Got it, thank you. So, in the interest of awareness for brands, what are the types of insurance that they need throughout their inventory life cycle?
Tim DiPietro: Yeah, so, inventory insurance protects you against more or less everything that’s out of your—outside of your or your warehouse operator’s control. So, I mentioned earlier things like fire or other natural disasters; those other natural disasters could include earthquake, hurricanes, tornadoes, flooding — it’s a very broad policy, even covering theft. Now when we say, “theft,” just to clarify — because, like, a lawyer, you know—we always have to put the preamble or the explanation there — we cover theft by forcible entry. So, if it’s theft that a warehouse operator’s employees are stealing, that’s, once again, as mentioned earlier, on the warehouse operator, but if the warehouse gets broken into, our policy responds.
So, when looking at other solutions, you want to make sure that you’re getting that broad coverage. Not all policies are going to cover things like natural disaster, you know? Or, sorry, I’ll take that back — things like hurricanes. Sometimes you’ll have the natural disaster coverage, but there’ll be a hurricane exclusion. So, especially if your goods are located in a hurricane-prone area, that could be excluded. It’s because it’s a higher risk, right? And it’s something that’s harder for the insurance companies to underrate. You know, based off of our underwriting team and expertise that is supporting us at Arch and, you know, what we’ve been able to build combined with the technology that we use, we’ve been able to get comfortable with that hurricane exposure even in higher risk areas.
As far as other things to think about: deductible. A deductible, most people are familiar with from your car insurance, right? It’s the cost that you have to pay before the insurance claim kicks in. You want to make sure that you’re looking at the deductible. There’s typically a deductible for normal losses — you know, as if a fire was to happen — and then for those, you know, hurricane-type losses, that can be different. So, you want to look at the policy and see what those deductible amounts are and how they compare to whatever alternative option you’re looking at, because that’s ultimately going to be [the amount] you’re out of pocket that you’re paying in the event of a claim. So, that’s important to be aware of.
You know, that’s really, I think, the high level of what our inventory insurance covers against. It does only right now cover the products in the warehouse. If you need transit coverage, either inbound Intermodal between warehouses that you might be working with, or to the end customers, we can provide solutions for that as well. But the core inventory policy is only covering the product while it’s in the warehouse. So, if you do have a high transit exposure, you know, you’re importing goods from China, for example, or, you know, wherever overseas, that is an important thing to consider. It is also something that we see most brands having a lot of confusion around of who’s responsibility that is.
Part of what we do, as mentioned earlier, is providing insurance expertise and a real person to talk to. So, a lot of the times, in those scenarios, we just simply ask the customer to send us a copy of the contract with, you know, whoever that supplier is overseas, whoever the shipping company is overseas. And if they can’t figure it out themselves, we’ll dive into that contract for them and say, you know, “It says right here that it’s your supplier’s responsibility to get it to the warehouse.” Most of the time, that’s where we see the responsibility of the brands picking up is upon receipt at the warehouse. Sometimes it can be at the port, sometimes it can be in transit, so understanding what your responsibilities are in that transit scenario is another thing that’s important to understand.
Rachel Andrea Go: You know, your hurricane story made me wonder: Is there anything else that brands should really be aware of when they assume, you know, “My insurance must cover this or that,” but, in fact, it’s often that these things are not covered?
Tim DiPietro: So, this is a little outside of inventory, but going back to going back to my comments earlier on general liability: General liability can be a multifaceted coverage. A component of that is product liability. It might not be included in the general liability policy; you can buy really cheap general liability policies that don’t have product liability. Now, if you’re dealing with one of those large, you know, vendors like I mentioned earlier — dealing with a Walmart, an Amazon — they’ll require a certificate of insurance that shows each one of those coverages line by line, so it might have a requirement specifically stating product liability where you have to show that. And so that’s where a lot of brands will be aware of if they have that coverage or not, but that’s not an important thing to look at absent an insurance requirement. Maybe you’re just starting out and you’re in a really early stage.
If you have a product that could create damage or harm to someone, that’s probably the first policy that you should be buying. And make sure that, you know, you’re not just buying a basic general liability policy, but you’re buying one that has broad coverage to protect whatever product you’re selling against so that, if something was to happen early on, especially when you might not have the controls in place to make sure that, you know, all the testings being done — obviously, we’re all moving fast. Outside of inventory insurance, that would be an important one.
And the other one we see is cyber. You hear about these large cyber attacks in the news, and they’re typically against the larger, big-box retailers or whatever else that makes the front cover of The New York Times. But every day, small businesses are hit with cyber instance, the most common being fraudulent transfer, where, you know, we see this very often: They might get an email from someone that looks like a vendor saying, “We need you to wire this money,” and it, you know, may just have an “n” instead of an “m” in the email address or whatever it might be, and they are once again moving fast and they wire that money without, you know, verifying that change in banking information or whatever it might be, and now that money is gone. So, that would be one of the more common cyber scenarios that we see.
Aside from just simply selling an insurance solution to protect it — you know, one takeaway from this call that everyone should be doing is, whenever you first get wire instructions or a change in wire instructions, pick up the call and verify. That’s the best insurance policy to do and, you know, absent buying any type of insurance, just make sure that you’re doing that, especially as an early operator to make sure that you’re not having that money go out the door because it’s next to impossible to get back otherwise.
Rachel Andrea Go: So, what is your advice to small versus medium versus enterprise brands regarding insurance?
Tim DiPietro: So, I think we see this across all levels. I mentioned that large company earlier that was doing $90 million in sales and had $10 million of inventory. It’s very easy, obviously, to get to that point. You know, you can have a very successful brand that grows fast, and all of a sudden, you’re at that point where you’re doing $90 million in sale and it, you know, could happen over the course of a year, it could happen over the course of 10 years. But I think just taking a second to pay attention to insurance. We recognize that no one wants to deal with insurance; that’s why we created StartSure, to try to make it as easy as possible, right? But it is a very important tool to protect your business, right? And coverage, whether it be through us or, you know, some other solutions that now exist, can be purchased online in a relatively quick and painless way.
And I think focus on protecting your business [rather] than just satisfying contractual requirements. Obviously, we all need to satisfy those contractual requirements if we want to land the big customer and move forward — [I] totally get that, you know; we can be helpful in reviewing those contracts and, you know, getting them satisfied and whatever else. But, like, just take a second, you know, 30 seconds, five minutes, whatever it is to sit down and look at what you have and say, “Is this protecting all that I’ve worked hard to build?” Right? And if you have questions, I’m sure we’ll find a way to link, you now, to StartSure where we’d be happy to consult with and answer any questions.
But I think what we see more often than not is just people sticking their head in the sand when it comes to dealing with insurance. And, unfortunately, we see it when companies call us back after we’ve maybe recommended things like cyber liability and they have one of those fraudulent transfer incidents. They’re like, “Is it too late to buy that coverage you recommended? We just had something.” Yes, that’s too late at that point. And relative to the risk that you’re protecting, it can be very cost-effective. You know, it is obviously another expense. We’re all trying to be as lean as possible, but, you know, don’t be whatever it is — pound— a penny foolish, whatever the saying is. Sorry, I’m forgetting it right now. But, you know, it is an important and valuable tool.
As the company grows, you’re going to have people that might be exclusively dedicated to insurance that typically come from an insurance background — they’re as a risk manager — you know, so, those large enterprises, they get it and they’re spending a significant amount of money on insurance because they understand the value and importance of it. Obviously, the earlier the stage the company is, the less experience they have with it, the less appreciation they have for what it could do to protect what they’re doing. And so that’s where we’re really focused on, you know, scaling down to the earliest stage about educating and just making people be aware of, you know, the solutions that exist to protect what they’ve created.