How do you close a seed round when VCs move the goalposts?

welcome to episode 32 of fundraising demystified today we have Jeremy vahan with us CEO and co-founder of start left security a cyber security software company for developers they've raised a $3 million seed round after passing 1 million in AR Jeremy walks us through the critical moment he meets his mentor to get his first check why he decided to participate in multiple accelerator programs how he managed fundraising like the sales process and how he was on the brink of running out of money multiple times but still managed to close new clients and successfully raise a seed WP as a reminder be sure to get notified of our weekly podcast and newsletters every week on Tuesdays and Thursdays Please Subscribe at join. thunder. BC again that's join. thunder. BC now on to the show hey everyone welcome back to fundraising demystified today we have Jeremy vau with us founder and CEO of start left security welcome to the show Jeremy thank you good to be here now I'm excited to to hear your story and be able to kind of understand your lessons to share to Founders on how you and about raising Capital so let's just jump right into it can you just tell Founders a little bit about you and what you're doing at start left security yeah so um I would say graduated a finance degree um which gave me a little bit of Finance chops to talk language of investors right business language um and then when smartphones came out I just knew technology was where I needed to go and so that happened to also be the recession 2008 2009 so moved into Tech um and so been a tech entrepreneur um in and around software software development um for the last 16 16 years and so um built uh start left security over the last couple years um and brought it to Market I in 2019 so you started in 2019 and you recently raised uh a seed round of around three million back in the summer of 2023 that's four years what were you doing in that time like what the what was the business achieving what were you working on how did you stay afloat how' that work Blood Sweat tears man um you know you everybody jokes about the ramen noodles and all that kind of stuff I didn't have it that bad but um it was it was sheer grit just to be honest with you um I raised a small Angel round um from a local investor that I had known for a few years prior um basically said hey I'm going to build I'm bringing this technology it's patented to Market and here's the opportunity present it to him he's like Hey listen i' I've always believed in you I knew you at your previous business roles and things like that so you know I'm in right and so that little belief and and and that that gentleman has always been he he had somebody do that earlier in his career right he's like somebody came in and just kind of changed the trajectory of his life and so he wanted to pay it forward that was the guy that he chose to pay it forward so I'm incredibly grateful and blessed that I met him um and at that particular time he had a little bit of U money to throw at a a a struggling startup right so um you know so we're we're in Florida right so we don't have access to Silo Valley money my Network's you know more geographically located at that time and so um I had to figure out like Hey how do I create a bigger Network and start to grow and and and meet people in other areas and so um I decided to join some accelerator programs that EXT expanded my extended my network to like New England U Northeast area um more in the Florida area so like I started covering more of um the East Coast right and try to get more um more our name and and things out there if you go packtrack the the timeline um that's when covid uh you know hit right and so I started creating relationships with investors back when that happened um and said hey I'm G to keep on building you know nobody wanted to put money to work during that time um I actually had some big deals uh that I had investors lined up with that if these deals came in they were going to back me and we could go accelerate right Co hit everything fell apart the the snowball just blew up right and so um I basically took a step back and said okay I'm just going to educate people I'm gonna still create relationships with investors and really just change the position of our our uh talk track which is hey I'm going to go create Revenue I'm going to figure this out I'm going to um educate the market form Channel Partnerships and what metrics do you want to see us achieve and then that way it make it make our make me come back with a more valuable conversation of hey we've done this on the product side we've done this we're we're reaching these Revenue metrics and really just wanted to keep investors close to our story um and actually see us execute and that became a really cool thing because the investors started to stay close with us and they saw us execute and I had to keep our reminding I'm like I'm doing this with no money right imagine if we can do if what we could do what my team could do if we had a little bit of cash right and so um that's what we've been doing um up until 2023 um the channel partner Network really paid off um because it did take that good 12 to 18 months to get running but in 2022 um we got a lot of Channel Partners throwing us uh deals and we were able to get up and over a million dollars in Revenue before we even started the seed round race um and so that was just us proactively being like you know what investors are the economic Times right now really hard investors don't really you know have the confidence to invest right now we got to do something else so that's what we did there are so many things I want to unpack from here and let's take a step back um looking kind of early days I want to go back to that angel invasor was it only one Angel check that you got or did you get multiple Angel checks so we got one at the beginning um the very beginning um and that helps me get through some legal stuff that we needed to get through launch the company um start building more to the product things like that it's important to know we already had like an existing product before I got that angel investment um so so we we actually invested in ourselves and put money into our product into our business before we asked anybody else and I would say a lot of a lot of people won't do that and that to a lot of investors is a red flag um they want to see that you're committed they want to see that you're going to do whatever you can to get this thing up and running and if you didn't put your own blood sweat tears money into it um a lot of investors will just say no like really quickly um and so you know now that I'm in this position and if I looked at somebody else looking to get money from me I would be the same way hey what did you put into it you know did you put anything into it like are your coach Founders invested you know um there's a lot of questions that you can go with that but yeah we got I would say we had that one and then um I got a VC firm um early on that provided us a little like a $50,000 check um above and beyond that kind of provided this bridge um to revenue right so like I closed our first deal which was a 100 it was the lifetime value $150,000 over two years and I was like that's closing in like three months we're literally about to run out of money um can I can and they gave us $50,000 to keep us up and running so it like we were in the red I was starting to spend my own money again and um it was scary right and um they we got that extra 50 we closed the deal um I was able to turn that deal into some more deals um and that really kept us afloat um you know moving into uh um 2022 and then we get we did get a I would say a grant um a small Grant from one of the accelerator programs that we were in um very small but also that helped us you know keep afloat stay above zero um and and you know manage manage the business what accelerators did you go through um so we did the which is no longer uh there it was a startup boot camp had a um Hartford insur attack Hub accelerator um so I actually lived in Harford for 6 weeks until Co hit and then the the program was was shut down you know as soon as Co hit um and so they gave us a little check it would that program was awesome I would say was one of the best ones that I've been exposed to um because they as a community they realized like what are they good at insurance right they have a bunch of insurance companies there they basically made made an economic development play of hey why don't we get all the insurance companies to um get involved with this program and then software companies can actually have um direct uh access to these people that could give us feedback they could do proof of value uh with you and you can learn like through the program with a lot of times real Revenue um but access to talent and access to people for that feedback which was which was a really cool thing um Tampa Bay wave um also um another acceler program we were the first cohort of cyber security um firms through that and um we were part of the University of North Florida um incubator program as well and so each one provide provided its own value provided its own network um and they were a they all added to a little bit of our s success here or there um so that's it was it was good um good timing too because again like covid it was everything was shut down yeah no I I find this interesting with a lot of Founders it just you got to do whatever it takes and you know sometimes those accelerator programs are can be a lifesaver sometimes they can be a burden down the road depending on how they're structured and whatnot and I always find that story fascinating because a lot of Founders you know they try to go out it alone especially like a first-time founder or you know someone does had hasn't had the experience those accelerator is can to open up new networks New Opportunities education stuff like that despite them you everyone's like oh I want to go to YC it's like well not everyone's going to go into YC so y uh there's plenty of other really good programs out there and especially if you're not in a major Tech Hub um I do see a lot of you mention like Tampa Bay has uh uh a location like that's you know not in Silicon Valley but they have resources towards you know supporting uh small businesses and startups and stuff like that which is great in Tampa has for us anyway then this is part of the story and what I think people should pay attention to as well as like the reason why we went insurance is because we're kind of like an insurance platform for software company security right um so and secur insurance is gonna want to see what we are providing and what we're measuring eventually when that when the insurance Market catches up and they realize like what we have and we can we can show for insurance claims and things like that um or underwriting um it'll become a thing we were way too early for Market um back in 2019 2020 for for charts um but Tampa Bay also cyber security Hub now right so like there's a lot of cyber firms down there there's a lot of activity around cyber security um so that was a a strategic move for us is like we wanted to get introduced to the Tampa Bay Community um in the Cy in the cyber secur space no that makes sense and you know one thing that uh you you talked about alluded to is just kind of really maintaining relationships with investors uh over the course of the business and being smart asking them like what do you want to see like when when you say like come to us down the road when you know when you're at later stage or whatever but it sounds like you specifically asked what were those metrics and then you work towards you know hitting those metrics and uh sharing that with them I guess what was that experience like how did you keep track of them how did you keep track of uh not just your you know not your metrics but how you presented it to investors and managed the those relationships over an extended period of time yeah Excel spreadsheet um but it was um I could I would say and this this intuition this confidence that I gain doesn't come quickly right so like when when people say they talk to hundreds of investors or whatnot um I talk to hundreds of investors um and so um eventually you kind of get intu an intuition of like how they answer the qu exactly how they interview US of like how we answer um specific things and like they're we we can do the same thing to them and like let's be honest like we're the entrepreneurs we're the ones with the the the ideas that's going to make them money so like we we need to really start being more confident of like talking to investors and doing the interviewing and um what I really figured out is like how to create fomo um if you're missing out and I did that through um basically saying hey here's what we're doing over the next quarter um I want to talk to you and can you please like put something on the schedule in April right and in April I'm going to share with you what we did what I have clear line of sight into and it's going to be everything you want to know about the business right and eventually we're going to meet the metrics that you want but I also will say I'm doing this with several other Venture firms that I'm tracking I'm keeping um I'm keep interviewing them and I you know it's it's you know I want to work with companies and and partners that are actually going to be partners to us um and I think in early stages um a lot of people just want the cash and there's so much cash out there but it's I don't want to say it's easy to get but I want to say you probably should be more strategic on who you bring into your business and so those those qualification questions exactly what we do in sales you know I don't want to do business with everybody we're we're a fit for certain companies and certain um characteristics of those companies and same I do the same thing with VCS is what are the characteristics I like in these in these people that I'm talking to um their value propositions um what they're going to do for us how they're going to work with us and so I would create like a qualification system for everybody and um you know also keep them true like hey I want to talk in um Q2 this day and let's just stay in in contact and of course a lot of people fell off through through that process um but then you were able to see like who the ones were going to last and be with you anyways and so you know just just create kind of like a sales process um like you do with anything else did you know that most Founders waste days of their lives chasing the wrong investors well as a Founder you know your time is your most valuable resource don't waste it on the investors that aren't going to write you a check here at Thunder we built a free tool that identifies exactly which VCS are worth your time to Pur we score your company against 3500 VCS and family offices that have been vetted and are actively writing checks into companies like yours get your AI recommended list of investors that will look like this absolutely free by creating a free profile at thunder. 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VC now let's get back to the show and it's a it's it's a demonstration of a skill set that BC's like to see in a Founder in in terms of being out run of sales process especially early stage Founders you know most of the revenue growth is going to be founder that sales so if the founder can run a effective sales process for raising money they can probably run an effective sales process process for acquiring customers yep uh so it's a it's a checkbox VC's look for and they often make Founders go through oops and hurdles to kind of validate that that skill set is there um especially if the relationship wasn't previously existing you know they don't know who you are they want to see that performance over extended period of time and four years is an extended period of time four years is a very extended period of time I would also say like there wasn't through the four years of at the very beginning I probably didn't have enough Insight or data points to I would say more predict the future um because like when the world's stagnant and nobody's adopting things and you expected things to happen um especially after events let's say like solar winds um regulation and all that kind of stuff happened like years later right and then we're sitting here waiting like that that solar winds event should literally make people move now but it didn't regulation had to come out which took years and now people are moving right and so um I didn't have enough like the data and let's just say things that were occurring in the industry to really be confident in telling people like hey this is what's going to happen and here's why right um once we kind of saw um some things unfold we were able to create a very impressive narrative that could predict what's GNA happen I could say hey I know that this is GNA happen this year this is GNA happen this year our high adoption year is going to be 2024 and then the major adoption years are going to be 2025 and 2026 and here's the data that's backing that right and so um once you're kind of able to get into those like confidence um points and you're able to like guide the the VCS um with that they're like yeah I agree with you or hey I see it a little bit different and here's why and a lot of times towards the end of that or once I get in like halfway to the capital race I had enough data that like the the uh BCS were following my lead they were like yep I totally agree with that I understand what you're saying and why that matters and why we're going to invest in you now because that's going to happen in the timeline that that you're saying it is and so um you know getting that confidence and getting those data points to be able to kind of like say predict that future um and make that feel confident and comfortable in that investment um is really important you know being that thought leader and and sharing that level of expertise and basically making the VC smarter um is is an incredible way to again build trust build a relationship and you know if they don't believe in you then you know it's probably not going to be a fit so you know finding those VCS that do buy into your vision buy into kind of your predictions of where the Market's going are key indicators that there could be you know a relationship there for for them investing in you Absolut you know you got to a million dollars in Revenue um and imagine it's it's SAS so it's is it like you know that's your Mr AR is around a million plus is that when you kind of decided like Now's the Time to start asking for money or did VC start to see your updates to like hey what's up Jeremy what are you doing both of those things happened um and I don't know how VCS get um maybe it's done in Ry I don't know I don't know how they get you know radio waves of we have money coming in but um I would say I tried to raise seed earlier and I stopped um and I stopped because I got frustrated I I was like I would get 300,000 revenue and they'd be like oh if you only got the 500 we'd be interested then I get to 500 and they'd be like oh well if you got to a million then we'd be interested and I'm like come on guys your moving the cheese like really like it gets to a point where and I think investors need to understand this is like if we get to a point where we don't need you anymore and you start throwing us money we don't need you anymore like you missed your opportunity right and you know I had another VC and I I it cracks me up he he always made jokes um and they they were part of one of the first VC's in um they were like I thought this was called Venture Capital like why is everybody being like you you have a good idea the Market's demonstrating it um you're you have the ability to form a team and talent it's Venture Capital it's not private Equity like let's go right so then this is like another VC um I was I was like can you talk to some of these VCS for me for me and uh it it was just a weird time but you know once we got over that million I was like you know what maybe this is time and maybe the conversation is going to be easy and if these if the guys that are telling me or girls whatever that they're still out and we're over a million that I got to move on like I'm not calling you anymore we're not friends anymore like I'm moving on like you know what I mean like you're just not that into whatever it is yeah exactly yeah yeah they're just not head to you um right so moving on and basically created a whole another way to to you know some of them stuck around not all of them stuck around you know but I do like to share this story because at the very end of the seed round I had money trickl or people trickling back in that were like oh you guys got that investor in you got that investor in can you take a million dollars from us and I'm like guy like we're already shutting the the round down and these are guys that told me no several times move the cheese on me several times and I'm like no guys like I told you like if if people come in first and you keep moving the cheese on me I'm not going to invite you to the to the dance anymore um so moving on um it was incredibly awesome to say no to to a couple million dollars um when they kind of made you squirm for months and months and months you know no it's a it's a very sweet moment when you get to go with the people that you actually want to go with and get to say no to the ones that you and it's your job like as a Founder you got to keep putting yourself out there and you you learn because you're putting yourself out there you can't just expect to hit a home run with the first relationship hope it does happen sometimes but in reality it's you know like you said you talked to a hundred investors you kept you know kept at it you kept building those relationships you kept knocking on their door and when you actually were the you know the person to be investable you know when you became investable and you were the the what do you call the the homecoming King that everyone wanted to be with um then you got your your pick I think the moral of the story the other day is one yes run a sales process you know build those relationships but build a great business correct build a business that has Revenue build a business that has defensibility in the market and that's ultimately what gives you the most strength and yeah sure maybe you don't need the money anymore but the money would be nice and the money can help you outpaced competition innovate be faster uh and hit that Venture scale velocity yep exactly so sounds like you ran us uh you know I'll be long but smart process and you played your cards right um what kind of growth rate were you at in terms of like month over month when you were at that you know million dollar Mark when you decided to go out and raise honestly I was not tracking that type of stuff back then it was I was just trying to keep the training wheels on man like and just just to kind of give you some data points on that it was literally me and my CTO and our director of engineering that were doing everything um so and then a couple contractors so like literally four four to five people getting up over a million dollars a year is hard as crap and so um I look at my team now I'm like I used to do that I used to do that I used to do that I used to you know what I mean I'm like these all these hats I'm like this is this is crazy right and so um you know uh we started when we got closer to that million dollars we started hiring more more people right so I say we are about four or five people for a good portion of that then I would say about when we started hitting four to five we started bringing on a little bit more part um contractors to help us out um and so you know we had to manage a team and we had a lot of processes that we needed to make and we like I said we were just trying to keep the the training wheels on and you know then not to not to overlook that raising capital is also a full-time job um so I honestly didn't really care about our metrics at that time I is like if I could have some money I could have some breathing room to uh start evaluating the metrics and and actually like making it repeatable well sounds like you played your cards right built something interesting got revenue to a point where it's was attracting the right uh players but I guess you got the three mil you you got some good investors coming in uh you're happy with that like what happened after you got that money well what what's been the last you know six to eight months uh since you got the money yeah it's been um I had to get um basically product operations running um getting the vision the understanding um head of product in there you know more people that can help us on a full-time basis um on the product and starting up our sales and marketing engine right so we've hired a lot of people in sales and marketing whether they're internal or agencies or or whatnot so we have a lot of things in the works that we're managing um and then uh really getting through um uh I would say we had almost product Market fit when I first rised we didn't have complete like our we didn't complete our our entire value proposition yet and so over the last six months has been a fullon like Sprint to get V version two out the door and make sales for um 21 and so um we made a couple sales at the end of the year but a lot of a lot of companies wanted to see our next vers and buy in the new year so um we got the version two out um early January um with no hiccups and we're we're screaming um our product Ops are working um everybody's in alignment um design are our new UI is slick um we're getting a ton of people understanding security above and beyond security people so like that was a goal of ours like make this less technical so like business people can can see what's going on um and then our our sales and marketing engine right and so um sales is hard to manage um simplifying your message from the founder to scaling it to salespeople is hard right and so like I can talk any language because and just to say it like we service like devops developers security cyber security people and business side people so like I can flip my language and how do I speak to people and like the value propositions to each like Persona on on a dime right um I can't expect salespeople to do the same thing immediately so simplifying the message simplifying how we're going to Market and simplifying how we're actually explaining the value proposition and then having scripts through the demos you know things like that that's been a that's been a learning curve for our entire company because what we're selling is not it's complex but we've made it simple and we're trying to make it more and more simpler um for people to go ahead and and push it out for us and I guess from you kind of mentioned the the buyer persona but what type of companies are these uh companies that you work with that you're going after are these like Enterprise scale side uh you know sales or are these more like small business type good question um we can Service Enterprise um in fact we have Enterprise in our Bine we haven't closed any Enterprise um we're getting more of those Enterprise clients via our Channel Partners um our my go to market what I wanted to focus on is software companies SAS companies um series like post seed series a b c um and here's why the there's a lot of tools in our Market Point Solutions one tool can eat up the application security budget and these are traditional vendors trying to play in our space um we took of a more of a stance of why can't we build a platform that has all these tools and then offer it to SAS SM SMB market for like a fraction of the cost of like traditional vendors in our space and so um I always say like don't bring your Enterprise strategy or or Batman belt to the SAS SMB like you're going to eat up all the budget why don't you take a different approach get it all in one place we can actually be your company your platform that can meet your needs and help you mature over the entire uh business life cycle meaning from raising Capital to audits to um preparing for exit so like your technical due diligence we help companies stay prepared we call it resilient and ready all day every day um and so having to be able to show security and security performance um throughout the all that is is really helpful for um all these people both the practitioners doing the work but also when the CEO is like hey guys we have an audit coming up are we prepared uh we have an exit coming up or we have like forensic investigation coming up are we prepared or we going to have to scramble because the more scrambling there is the more developers are not actually delivering product features so um that's what we that's the insurance piece of we're helping you um keep the speed of velocity and the interruptions to a minimal that's actually a lot of value there just cuz you know when I when we sold our company to wall the diligence and just the tech and it was just like and not being able to tell our team why they're having to produce certain like security reports and stuff like that like hey like you look into this and tell us what's going on there like I'm busy doing this what do you want me to do like uh prioritize the thing that doesn't sound very important yep yep and trust me it's it's worth it just just don't ask questions yeah man and like this is what I was trying to say earlier is like to predict what was happening in the market and when this stuff was going to happen on the timeline was very important and so like everything that I predicted is starting to come true on pretty much the timeline that I said to the investers and like we've done Tech due diligence with companies like we work with a couple private Equity companies that um their port codes are all software companies right and so I'm like guys like security is just good business now it's it's it's it's it's not going to get easier it's going to be more and more a requirement more we go into the future right so you might as well start dealing with this now um and so that's I mean that's really what's happening that's you know um these we've done Tech due diligence we've persuaded people not to buy because of certain things and we've given companies more valuation because of the things that we were able to highlight and by the way these Tech due diligence people um they're going to try to devalue you as much as they can right and so any little thing that they're going to find they're going to be like hey they had a security incident and what we found is they didn't actually ever do any mitigation it's still a wide open hole and the CTO did nothing about it and so okay like once they discover that we're not buying anymore yeah so they could definitely go deals like cyber security is especially in a bigger company and a larger scale buying a smaller company they're big risk is some kind of security breach that leads to a press release tying the big company name to a very small business yep where the net negative impact outweighs the purchase price yep um of the company and with my nent insignificant size startup in comparison to the Behemoth Walmart they dug deep real real real deep uh and so I can definitely relate to the significance of um you just Cy security as as a whole and for any tech company that you know if your product involves technology to any degree uh or you're St customer data or anything of that sort uh cyber security is a is Mission critical so oh yeah well you saw I mean you saw when MGM went down right uh that was all software by the way and uh how many millions of dollars of Revenue did they miss every single day right like a ton a ton like hundreds of millions of Revenue it I know they reported less than that but let's be honest it didn't actually line up to their their yearly annual revenue um so that's what else like everybody's focused on like customer Data customer data like that's what compliance is focused on yada yada yes our customer data is valuable but I even said this somewhere else like the whole industry jokes about like the data is already out there right so like why do we even care about that stuff but where you where it's like a product focused company or software Focus company all of your Revenue all of your customer experience is going through that um if back to MGM uptime availability like these are all security these don't this isn't really talked about in Security in normal cyber security or traditional cyers secur this is the proactive security that we actually enable that we're trying to say hey guys if your system goes down you're dependent on your system and so are your customers like that's a lot of money that you're missing like that's that should be important to you I completely agree and I'm really glad you got the opportunity to kind of share more about what you guys do at startl security uh for for the people watching or are listening into this show where could people learn more about you and what you're doing at startl security um I'm on LinkedIn Jeremy vaugh uh that's spell vaug g h an um you can find me have a I think a bright pink portfolio or biopic um and then uh starse security.com is another one and uh before we we part ways here what would be some advice for for Founders that are looking to kind of get their seed Brown closed and you know something that maybe we didn't cover um so far yeah I would say this is something that I learned the hard way um and I think you mentioned it on a on another video but like um I used to be scared to go to Industry focused VCS like safe cyber security so I did a lot of General um VCS or ones that were focused on data or like it infrastructure right and like of them just didn't get it right and the reason why I was scared is like these cyber security VCS get a lot of the same decks like presentations and I'm like do they share them around are they gonna steal my idea blah blah so I was really scared um I took a step back and I got over it um and the second I did it changed a trajectory and I changed my thinking of I just need one cyber security lead uh investor that is very well known in the space and go get that one and then go create fomo and momentum with everybody else and so what I did is I went um we got Ron Gula founder tenable um his VC firm invested and a couple of his members there and then I took that and I got litical and I got you know a couple General VC funds and also when you're talking about the characteristics of these VCS um I asked them hey can you help me like if you're really a parter can you guys help me so like they would like a couple of them started to protect their investment and in in uh inro us into other BCS that would invest alongside right and so you kind of have to push people to do stuff to help you but like once you start to get them and they're already in like it's a lot easier for them to go and push you through their Network right and so that's also a sign that they're going to help you in F in the future as well and so um that's just a little little learning curve that I had and uh you know I think I think it's really valuable to kind of change your mindset and your perspective of how you you actually attack um raising your Capital that is some great parting advice for for Founders to to understand you kind of poked on one thing that that fear aspect of will they steal my idea will they share the deck and uh the common response and I always tell founder is that if if you're worried about your entire business being stolen and being you know you're going to go under because you shared a deck then your business wasn't that good in the first place um and so that's something I always kind of remind founders of to yes just put yourself out there you're gonna you know things may happen but you're not going to have a shot unless you build those relationships and put yourself out there so agree I'm glad you shared that with h with our audience um so Jeremy it's been an absolute pleasure having you on the show really appreciate your insights thank you so much for for joining us thank you thank you for your time love the show thanks for listening to the show today we hope you learned something valuable and if you did be sure to let us know in the comments or by hitting that like button and if you're a Founder looking to raise Capital then join us at thunder. 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