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Natty Zola | Matchstick Ventures

47m 12s

Natty Zola | Matchstick Ventures

In this episode of "Fun Raising," host Matt interviews Nadi Zola, partner at Matchstick Ventures and former Techstars managing director. Nadi shares her journey from founder to VC, emphasizing her passion for coaching entrepreneurs. Matchstick invests in pre-seed and seed stage companies in between-the-coast markets, writing checks of $1–1.5 million, and focuses on generalist investments with growing interest in deep tech, quantum, aerospace, and service-as-software. Nadi highlights that founders often underestimate their power in the VC relationship, as VCs need founders to exist. She advises founders to qualify investors carefully, seeking those who already believe in their thesis rather than trying to convince skeptics. Matchstick differentiates by providing high-value, low-overhead support, leveraging founder empathy, local presence, and strong Series A graduation rates. Nadi also notes that their LPs include charitable organizations and pensions, aligning returns with social good. The conversation covers the fundraising process in three phases: building a targeted investor list, making a strong first impression, and closing the round efficiently.

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[Music] Hey everybody, welcome to another episode of fun raising where we interview top early stage investors and ask them all the questions that you as a fundraising founder want to know or wish you knew about the fundraising process which as the name implies is actually not very fun at all. And today I have a very, very special guest special to me. I think special for all the people that are going to be listening. Nadi Zola, partner at matchstick ventures and then was also managing director of tech stars for six years. We mentioned this before the call. I think it's absolutely true. I think there are very few people on the planet that have seen more pitch decks than you have Nadi. I also want to call out that you were also an investor in my first startup and can say very easily that you were one of the most impactful investors on my cap table. So again pleasure is mine. I'm very excited to have you on here today. Can we start a little bit with a quick overview of matchstick ventures? What are you investing in? Average check size and maybe the stages that you're investing in? Great. Well, thank you for having me on Matt and it's been fun to follow your journey and be a little piece of it as well. So yeah, I'm a partner in matchstick ventures. I'm based in Boulder, Colorado. Our fun thesis we're investing in preceding seed stage companies that are based between the coast heavy emphasis on Boulder Denver, Salt Lake City, Austin, Chicago, Minneapolis, Toronto are kind of the six major markets where we're finding high quality entrepreneurs, high talent density, high entrepreneurial density, a lot of overlooked founders, frankly. And then we're opportunistic across the broader regions, but mostly focused on those six geographies. As I mentioned, preceding seed stage, average check size, one to one and a half million. We're happy to lead. We're happy to follow. We mostly just want to get conviction in a partnership with a great founding team and work alongside of them. We are generalists believing that we're not the best predictors of the future. The founders that we back are and it's our job to go out and meet tons of them and find the ones that we're most inspired by and line up capital behind their vision. So yeah, we are generalists and I have historically done mostly software, but some of you will talk about later as we're doing a lot more hard tech and deep tech because we're seeing a lot of strength in those areas between the coast and New Mexico, Colorado, leading in quantum, a ton of aerospace, advanced manufacturing, robotics, stuff like that. And that's very exciting to us right now as well. Yeah, I love that. It's a great overview. It's also a theme that we're seeing kind of across the board in venture these days. I feel like you know, software and AI not only as an unlocked so much, but I think more than anything, it's unlocked so much more in hardware, like teams that you historically would have taken dozens of people, maybe tens or hundreds and millions of dollars can now take, you know, small fraction of team and cost to get further, further along. So we'll definitely talk more about that. We have a few questions here, introduction ones that were essentially voted on by the founders that are that are listening. The goal these is to get to know you a little bit, but also maybe peek behind the curtain at what it is to be a VC. The first one is, why did you choose to be a VC? You have a neat background that maybe get into as a founder operator turn VC, which I think is one of the best paths. But maybe to the audience here, why did you choose to jump into to VC? Yeah, I started as a founder first. I got a finance degree, worked in banking for a while, but I decided to start a business with my childhood best friend and moved into our parents' basements, taught ourselves how to code and built a company in 2008. And I loved building. I loved being a founder, and I loved my VCs. And I think I got really lucky because I had really good VCs as investors in my company and VCs as friends and mentors. And I always thought while I was a founder, I'm like, someday I'd like to do that, but I was on my founder journey. When I sold my company, I worked at the acquire for a couple of years. And after that, I got a call from Techstars, who was hiring a new managing director for the flagship Techstars accelerator program in Boulder. And I applied for that and realizing, hey, this could be a great opportunity to start my investing career. And I ended getting that job. And it was a great opportunity for me to learn and see was I helpful at helping founders in the early stages. Did I like it? And I fell in love with it. I think I'm a really good coach. I think I'm a good player, but maybe I'm a better coach. And so getting to be an investor, you get to help founders through the entrepreneurial journey. And I kept helping founders through running Techstars. And the main feedback I got was, hey, Nadi, we love working with you. We just wish you could write a bigger check. And so I decided, hey, I can go solve that problem. And I teamed up with another colleague at Techstars. And we ran matchstick ventures on the side for a couple years. And started writing bigger and bigger checks and raising more and more money into these founders that we were working with. And it's just snowballed. And now we're onto our fourth fund. And I just, I love helping. I think I'm a better, maybe better coach than player. And I just love entrepreneurs. I think entrepreneurs build a better future for all of us. And so there's no better job than being a little bit of tailwind on that journey. And I'm a little bit biased because I got to ride along a little bit during the time when you were at Techstars. But I also think it was one of the more meaningful times that Techstars kind of had here in Colorado. Truly, I think solidified itself. Not that before you didn't do that already. But certainly, what was it? Like late teens, right? Is that like 2015 to 2020? I think Techstars was really hitting its stride. And then I think, obviously, during the pandemic and all those areas too, you were a cornerstone here in Colorado. Still remain to be. So we definitely attest to that. Another question here. What is your favorite part about the job and being a VC? And then what is your least favorite part about the job? Maybe two things I'll highlight on favorite is first, I just love working with super smart and ambitious people. I need the best, the best part of this job is like every day I'm just meeting people who are trying to build something pursue something they're passionate about and want to change the future. And ultimately, we spend time, most of our time, we spend with people. And I just get to spend it with inspiring people. So that's first, maybe in foremost. And then second, I would say, is like I did a find your why exercise. And one of the main why's for me is helping other people feel safe and secure to pursue their dreams. Ultimately, like when I see a sappy, cheesy sports movie, like tears flow, I love seeing people like achieve big audacious things. And I don't know, it's just very motivating for me to be a small piece of that journey. And so I just frankly, I love seeing people accomplish difficult things. I love seeing people work really, really hard and hopefully succeed at the end of that. And even if they don't just seeing the transformation of those people over time, that's just fills my cup up. And so that's my favorite things, my two favorite things. I would say least favorite is probably the opposite of that is I hate seeing people not achieve their dreams. You know, it's hard. Not every company works. People work super hard and don't get the outcome that they want. I hope that they all can look and say, hey, at least the journey was worth it. I grew. I did something that very few people accomplish, even if maybe I didn't achieve my goals. But I just think the hardest thing is seeing people work really hard and not achieve their dreams. So that's that's the toughest part. One of the things we talk about a lot of this podcast is that the odds are kind of against every founder. Most founders don't make it. So it is important to try and learn as much as you can and enjoy the process as best you can, even when the times are hard. Next question, what are some of the things that you wish founders maybe better understood in the life of a VC? I think a lot of times it feels like it's kind of mysterious and behind the curtain a little bit. Is there any information or things you wish founders maybe better understood about the VC world? I feel like that founders don't realize that like we need them more than they need us. So VC doesn't exist if there aren't people building companies. And I think the power dynamics adventure have been set up in a way that makes it feel like the VCs have all the power. And yes, entrepreneurs do often need money. But without entrepreneurs, we have no job ourselves. And so I'm always coaching founders to at least mentally somewhat flip the table for themselves and say, the VC needs me to exist for them to to have their job. And frankly, I'm giving them an opportunity to buy equity into my company and benefit from all my hard work at the lowest price possible and maybe make them rich, make them successful, help them achieve their goals and build a little bit more confidence. And I guess take a little bit of the power away from the VC. So that's the thing that I wish founders more understood about VC is how much we need them that they have more power than they I think they feel like or the system is set up to make them feel. No, a lot of founders listen, they probably definitely don't feel quite that way. And maybe takes two or three companies in to feel that way after a couple of good exits or something there. Next question, what areas or industries are you personally excited about? You mentioned being a generalist, which is great. Any areas right now that you think of that are maybe more exciting or that you're excited about? Yeah, a couple here. I think this trend around like service as software is really interesting. So we have a couple investments where we're running a service business with a bunch of AI under the hood in ways that services business weren't able to be run prior. And ultimately what the goal of that is to just run a high increase the margins in these service businesses and therefore increase the quality of the offering to their customers. So I think we're really interested in that space. I would say we're we're very interested in like a deep tech, quantum aerospace. We've been doing a lot of work in New Mexico and there's a lot of really interesting technology coming out of there. Colorado and New Mexico have partnered on a Quantum initiative that the federal government has backed. That's very interesting energy infrastructure, which is something I think VCs were not that interested in a while ago is something we've looked a lot at right now. So yeah, I would say like maybe stuff that's untraditional for VCs. So services, services software and then hard and deep tech have been big focus areas for us lately. - Yeah, I love that, those are good ones. Our last question here on this particular section, this is kind of your moment to shine for a minute or two on why founders should pick matchstick or you to be on their cap table. - I'll let maybe our founders talk on that. So we have a super INPS from our founders. And I always ask them, you know, why do you give us a high rating? And ultimately they say the signal to noise ratio from us is very high and the value to overhead or time ratio is very high. And ultimately the way we think about it is like founder time is the most important thing. So we should be like massively accretive to the founder's time. And so that means we don't bother founders with dumb things. We're really only like here to help open doors, put a little tailwind in the sales or be there for a difficult moment. And so maybe sometimes that shows up as like we're less hands on than other investors, maybe we're more hands on but it's very like, I don't know, I would say like the ratio of help to overhead is very high for us, which I think founders appreciate. We've all, every partner in our fund has been a founder. So we know what it's like. We've been in their shoes. And I think we have like a very high like EQ and empathy level for founders. I know every VC says that their first call. I truly think we are like the number of 11 or 12 p.m. phone calls on a Friday night we get is is a lot. And I love every single one of those because it means the founders really trust us. And then I think a lot of founders want to have a local partner where they know we can drive over and see them or jump on a short flight. That's I think really beneficial as you're trying to scale a company between the coast. Another one is we've been very successful at helping companies graduate like our graduation rate to series A is two or three times the national average. And so many founders know that they need to raise that next round and we're really good at helping a company not only achieve the milestones to earn that next round but meet those investors, especially if they're based between the coast. We often joke that many of our founders can't go to the Soma Blue bottle and run into 10 series A firms over lunch. So we are effectively the Soma Blue bottle for them where we build those relationships and make sure that those series A investors are paying attention to the companies in our market, which is a really I think powerful thing to help entrepreneurs between the coast. And then the last one I'll highlight here is our LPs are mostly large charitable organizations and pensions. And so the returns that we generate go to people who are doing real heroic work, firefighters, police officers, school teachers, and I think many founders prefer to have their returns go back to the great institutions that have chosen to back match stick that were grateful to work on behalf of. So I know maybe maybe those are the main reasons to choose. Those are all those are all really good reasons. And then I can say as a as a former founder invested in by match stick that I think more than most VCs you truly do have a carrying you care about the founders almost not more than the returns, but I a lot of VCs even some they were on my cap table. It was always a how are things going and what they were looking for was like house growth and how's revenue you would reach out and it would be truly on how are you doing because at the end of the day it's a very, very hard journey. And I was felt like you were in my corner is a is a human being at the time to when I was raising I just had my first kid. In fact, I think I signed the first term sheet right when I was in the hospital and and you were there I think for the first few months and making sure that I was taking care of myself, which you know again VCs all like to say they are the first call and they do care about those things and they do, but I do think that you were truly truly great at doing that. Well, thanks. Well, we do really care and at the end of the day it's people, you know, and we want to see you achieve your dreams. And also like we deeply believe that the main limiting factor in a company is the capacity of the leadership team and their energy and focus. And so it's like, yes, we can solve a marketing challenge. Yes, we can make an introduction, but if we can help make sure that the founders are operating at their highest level because we're helping them scale, we're helping them grow or we're helping them just manage something in their personal life or aware of it. Like that is what pays the most dividends in terms of like long term leveling up of that, the potential of that company. Absolutely. It's a marathon, not a sprint. And that certainly plays into that too. All right. Let's get into the actual fundraising process here. We break it up into three parts, essentially. We have the first, which is a lot of folks listening. They don't have the network to your point. They don't have a blue bottle coffee or any place where they can go and just all of a sudden start meeting new investors all the time. They don't have the role of decks. How do they actually start making those relationships get their decks in front of the right people, choose the right investors to reach out to everything there? The second phase is they've done those things. They now have the first initial meeting, the first 30 minutes where they can hopefully make a good impression. How do they shine during that moment is the second phase. Third phase, they've lined a lot of those up. They've knocked them out of the park. How do they actually push things over the finish line and close up their round? So we'll cover each of those. Starting with the first one, we see a lot of founders. What they typically do is they make a role of decks, a CRM of all the investors that they want to reach out to. But a lot of times when I see these lists, there's a lot of mistakes. They've reached out to maybe you're trying to reach out to the wrong investors. What feedback would you give founders in making that initial list of VCs or funds to reach out to? I think qualification is super critical. Like everyone needs to do it. Sales, people, founders, we need to do it. Frankly, when we're raising our funds, who's excited about investing in preceded stage companies between the coast. And so I think qualification is super key and don't waste time and with people who are outside of who are not focused on what what stage you're at, what area you're in, et cetera. So that should be table stakes. The way that I advise founders on this is goal number one is for you to find the investor who already believes in what you're doing and has been looking for you. It's a little bit counterintuitive, but it's like you almost would rather have a smaller list of investors who are interested in your market than a lot of investors potentially interested in your market because it helps with the qualification step. But ultimately, and I mean this in a loving way, you kind of just got to kiss a lot of frogs till you find your prints. And a lot of that is just figuring out who already believes because it's way easier to get an investor to say yes when they've already believing your thesis or your business model and have been looking for you. So I generally think that that's your goal is to find the believers who are already out there. Your second goal is to find the investors who are open-minded and like will become believers and you teach them something that helps them think differently about the world. And therefore, they become a believer. That the anti-pattern is to try to convince an investor who doesn't believe is just a waste of time. So I think the main goal a founder has in the first meeting is just figuring out is this like a potential believer in my company or are they already a believer? And if you feel like no, I would move on from that investor. If you feel like maybe, okay, do another call. And if you think yes, put like mega effort behind that investor. Yeah, I think that it's very common that we see founders spend way too much time. Investors are very good, not maybe evocally saying how excited they are, but in their actions are usually pretty good. It's saying how excited they are about something. But it's hard sometimes to hear that. So I agree finding the right investors that are excited about what you're doing. That is absolutely true. Well, let's say they found that list. They have some investors. The goal for them now is to outreach and get in touch with these investors. What are some of the best ways maybe for you at match that founders can get in touch with you, but then maybe across the industry, where you seeing founders have the best rate of getting in front of VCs? We pride ourselves on being accessible. So like our emails on our website, we have a form on our website. And so we do look at everything and candidly like it's an uphill battle to get our attention and investor attention. And so the good news for founders is VC is more competitive than ever. We are all we all want to be accessible. We all want to meet as many companies as we can. So it should be relatively easy to get in touch with someone. But that also means that there's way more noise for all of us. And so my main advice on this is you have to do something to stand out. How do you stand out? That's like a warm intro is like the obvious one. Maybe accomplishing something that you can then share that is noteworthy. Some sort of breakthrough in your industry that we can pay attention to, win a pitch competition, do an accelerator. You basically have to like do something to stand out. And if you can't figure out a way to do that, maybe your best bet is just right and incredible cold email. And I think that's hard to do. How do you keep it short? How do you make it memorable? But ultimately you just have to do something to stand out. Yeah, agreed. Is there anything that you look for in those initial cold out reaches emails, whether it's an email itself or even the subject line itself that can get your attention that founders need to include? Yeah, the main thing for me is like I'm always just looking to be surprised. So that is like an interesting stat I didn't know about a new market opportunity that's emerging because of some trend. Some unique experience that someone had that makes them uniquely qualified to do this business. Like I just want to be surprised. And I think many founders don't realize, we're meeting each of us is meeting somewhere between five and 20 companies a week or looking at. So we just see a lot. And it all unfortunately kind of blurs together unless there's something that's surprising. So For whatever your business is, is fear out what's the most surprising thing around you, your company, around your industry, and like try to use that as the way to stand out is my best advice. Yeah, I like that. One of the best ways that you can get a VC's attention is in the pitch deck. If you've done the right things, maybe it's a warm intro. They've somehow written some sort of blurb that gets you excited. Usually, VCs will go to the pitch deck. Are there any slides that stand out for you or slides that maybe you gravitate towards it being some of the more important ones before you'd hop on a call? I think I go to two first. One is team. We're very team-centric investors, so I kind of want to know who you are. I think most team slides are terrible because they don't tell me why are you uniquely suited to solve this problem. They always kind of say like, logo's of where you worked, but I want to know why you. And so I encourage founders to make your team slide much better. What is your unique insight? What is your unique capabilities? Why you, more than what have you done in the past? And then the second one I go to actually is competition. And so I want to know who do you think is your competition? Most competition slides are not good, but I really want to know the best competition slide I want to see is what are other people doing in your space and what are they good at and where are they going and how are you good at something different and going in a different direction? And so I kind of go to those two slides, which yeah, that's right. Those are good ones and they kind of complement each other in a lot of ways too. So that is great. What about you seeing more? It helps me know like how are you aware of what's happening in your market and like are you picking good real and real competitors, which gives me confidence that you really have done your homework on the market? Yeah, I agree. Are you seeing more memos these days too? I think the other thing you mentioned investing more into deep tech. Deep tech is hard because typically you have to spend a lot of time explaining very complicated, you know, science, developments, all these different things. What about memos or longer form ways that founders can get that in front of you? I actually prefer a memo. Maybe I don't know if that's unusual, but I prefer a memo because I want I actually want to hear your see or writing and your depth of thought. I think slides focus too much on aesthetic then content or like whatever sizzle versus steak or whatever you want to say. So I like a memo, but it also still has to be skimmables. Like there's the layout of the memo is important. Like give me the skimmable headlines and then I will choose to dive in, but I actually prefer a memo because I can I think I can get more depth of thinking out of that than a pitch deck. I saw I've seen this on websites now, but we had a few folks do this more recently, which I thought was great is they had a one click put into like Claude or open AI that immediately like uploaded their memo, but then allowed you to like talk about it and all these different things that even had like suggested questions. And I thought that was great. And I see more founders or sorry, more VCs today that are taking either a pitch deck or a memo and they're just putting it into Claude and then using that as a way to kind of get questions back and forth. So if you assume that that's a process VCs are going to take, it doesn't hurt to have that as a solution to great. We have we I mean, we do that too for sure. Yeah. Yeah. Other question or are there anything that we're missing on this phase of any advice feedback mistakes that you see founders make during this initial phase where they're reaching out to a lot of VCs cold outreach and just trying to get their attention trying to get that first meeting. Authenticity cells so like don't feel like you have to be someone else be yourself. Many of the big winners have come from people who are not out of central casting and I think like lean into that if that's you. If you're if you're out of central casting or whatever that means great. That's you too. But like especially at pre seat and seed don't don't let too much like VC speak creep into your pitch deck or your memo or your narrative. Yes, like be aware of VC speak but like if you're not authentic, I think it's an easy it's easier to dismiss it. I agree. I think the authenticity piece is huge too and founders I think try to pretend to be maybe something that they are not to really try and impress. But we see so many of these that sometimes it's easy to to to see right through that. So I agree be yourself. It's certainly a long journey. It's going to be hard to be somebody else for that long. All right, let's say they've done all these things. They've done the right things. They've landed a meeting with you. What are you thinking of going into this meeting? What do you need to get as a VC during that 30 minute intro conversation with the founder? Two big things I'm looking for is one is like depth of understanding of the business opportunity or market. And then similar to that is clarity of thinking. So I like to see founders who have relatively short answers but are very precise and well thought out. So longer, but sort of the longer the answer, the the worst for me. I want to cover a lot of brown. Get the materials ahead of time. We do decent prep for every meeting. And so we're ready to meet those founders and go relatively deep with them. And often it can be clear that there was not a huge depth of understanding or thinking because the answers are long. What's the classic thing out if I had more time? I would have read in a shorter letter. That's really what we're looking for is like depth of thinking depth of understanding clarity of thought. And we want to cover a lot of ground in first meetings. Couple recent questions. The founders were kind of curious about maybe like rapid fire style. What do you feel about multiple founders on a call versus you know, just the CEO. Is there any sort of balance or cadence there? Because we have a lot of founders that are like we bring the whole team. Do we just bring the CEO? Especially with hard tech and deep tech. There's a little bit more questions there. What are your thoughts on that? I don't care for the first initial call, but at least from our perspective, from our second call on, it's always the full team. We want like we feel like we're investing in a whole team and we want to see how they interact with each other, understand their roles, how they divide stuff up. So for us, it's okay to like when we're first learning about the company, keep it maybe just the CEO, but after that, it's full team always. Yeah. Other question was pitch deck or no pitch tech in that initial meeting. Do you have a preference? I'm probably 50, 50. I don't think I cared that maybe more it's like how do you use either of those, whichever we go, a bad pattern is to say, hey, I'm going to pull up the pitch deck and then use 15 minutes straight going through it and not at least checking in. So like there's some EQ that needs to happen. If you use the pitch deck, which is to first assess, like, hey, have you seen the pitch deck? Do you have any questions off the top? Are there any areas you want me to emphasize? I'm going to go through it at a certain cadence, maybe pause at the end of each slide to check in. I can't tell you how many founders they feel like they can sort of like getting the pitch deck up gives them 15 minutes to just talk and I'm like trying so hard not to check out, but it's like so hard not to check out if there's not back and forth. So if you're going to use a pitch deck, just be very intentional around how you use it. And then if you don't use a pitch deck, just know that you're not really as able to control the flow of conversation. But I think it's a little bit better than because then you're hopefully asking more questions to the VC around what they're interested in versus you sort of inundating them with the things that you want them to say. Let me take that full circle though. I do think founders should have three must errors, which are the three most important things they want to make sure they get across in every meeting. And that changes based on maybe it's meeting three with the VC versus meeting one, your must errors change, but you have to figure out a way to get those three things into every meeting, regardless of what the structure of that meeting is and have the intention around that. And that's probably the more important thing is like what do you want to make sure you communicate in this meeting and get across whether you're using a pitch deck or a or not? Yeah. Kind of similar to that. You mentioned like a little bit of a back and forth. Other questions that we get from founders are whether they should be asking questions. Like how much ownership should they take into this? You already mentioned some on maybe at the beginning on how to direct the call. What about towards the end of it or more specific to the fund itself? Are there any questions that you would recommend founders ask of the funds during that meeting? I mean, the classic ones are what's your process look like, but I would actually go deeper than that. I would ask them, well, was their last investment they made and why did they get excited about it? That tells you two things as a founder one. Are they actually active? I met an LP once who we had five great meetings and I asked them in the fifth meeting when was the last fund they backed and it was 2015. And this is me. I still love them. I mean, but if I know that meeting one or two, I might have prioritized them differently and they're good friends still. So it's totally okay. But what was their last investment? So one, you figure out if they're active or not. Two, you can kind of dig in and figure out like what got them excited and that gives you a lot of intel to then make sure you're telling sort of a narrative that can match that as well or figuring out where the gap is there. And then the other question I would ask is what are they excited about or looking at right now in their pipeline specifically because I think founders don't realize they are competing with what else is in the investor's pipeline more so than maybe anything else. Like every business I meet and every founder I meet like has some fundable story or it is compelling. Like everybody has a compelling story. It's more just like I can only invest in one out of every 250 companies I meet or something like that. So you're really competing with the other 249 companies that I'm looking at more so than anything else. So you can kind of like get a sense of what Let's go. is interested in and hopefully calibrate where are you in their pipeline is a helpful thing to ask. Yep, yep. That's a really good one. What about towards the end of it? What do you typically see founders or what's the best way for them to end a call? A lot of times you see founders almost forcefully say, hey, like you're free on Friday. Let's hop on a follow up call and they almost push it too much. Sometimes that's good, but founders want to know like where's the balance in trying to schedule the next meeting or how should they end it in a way that continues to build momentum, but maybe isn't too pushy. I think the founders should always figure out some sort of follow up the founders responsible for. So, hey, why don't I send you some research on our market or hey, we dove in a ton on competition. I have a set side memo on competition. Why don't I follow up with you on that and we'll set up. So I think you want to have marry that with also something that you're hopefully going to get out of the VC. Almost always the next step with the VC is another meeting. And so you're likely trying to figure out like how can I get that scheduled. But the more little like touch points that you can get with someone, the better. I'll remind founders that VCs are super busy sending long responses like you want lots of little touch points. I think the Mark Suster investors invest in lines not dots is like so true. And so you want to figure out like what are some dots that I can plant along along the journey here as small quick check in touch points that like steer towards a meeting and show your momentum and progress. Yeah, before we jump into the next phase, any other pieces of advice pitfalls mistakes things that founders can do to better prepare or shine during the initial meetings. Nothing comes to mind. Okay, perfect. All right, so they've done well. Usually they're lining up a bunch of these initial meetings. After that, you end up going into this next phase, which feels so strange. It can sometimes go quickly. Sometimes it can take a lot longer than you think usually it does, but usually you're kind of in this area of hurting cats. You're trying to get in touch with VCs, maintain momentum. You're trying to get answers from VCs. Like you mentioned, they're always busy. So it's hard to keep attention. What are some of the things that you see founders do well? Maybe during this phase of the process in keeping momentum strong as they're trying to coordinate all this. The best thing founders can do is be very disciplined on their process. So fundraising is weird. It's basically sales, except for unlike say sales, your goal is to close as many people as soon as possible. Goal in fundraising for a founder. It's sales, but you want everyone to close at the same date. Or you basically want to like steer like the best scenario for you is you get multiple term sheets at the same time. Or you said another way you have VCs all at the same point in their process at the same time. So as a founder, you have to really understand like some people you're speeding up in your pipeline, some people you're slowing down, because ultimately you want to get like a bunch of folks close to decision, get one of those people to say yes, and then leverage that to like increase the number of options that you have as a founder so you can pick the right partner for you. And so really the only way you can do that is to just be very disciplined on the process and your note taking and set it up ahead of time. Try to do a ton of outreach at the same time. Focus almost all your energy on fundraising for a limited period of time. Not trickle it out over a long stretch of time. So I just think like founders are too flippant on the process itself and they would be better served to run it much tighter. Yeah. Speaking of process, could you give a quick overview of what your process typically looks like at matchstick from the diligence side from initial meeting to the kind of final check? Our process is pretty light. So we have three, three investing partners on the team. You don't as a founder, you don't need all of us to be a hell yes. You need one of us to be a hell yes. So we are a champion focused versus a consensus focused firm. And we believe strongly that one person needs to be a hell yes. The other two need to give it a thumbs up and say they support it because we're all responsible for everything in our portfolio and will help every company equally. But we don't all have to be a hell yes. So really what that looks like is one of us gets super engaged and then we start to loop in the other people to use them to help us understand the opportunity to get them comfortable with it. So our process is pretty organic. It's just a bunch of meetings. And so that can take two weeks. It can take six weeks. I think the fastest that we've taken is probably four days. But it's just a lot of getting us comfortable with you. And frankly, I think it's also you as the founder getting comfortable and excited about us. So we one of our checks in our in our processes. Are we getting more excited? Every subsequent meeting with the founders and hopefully are the founders getting more excited about working with us every meeting that they meet with us. And if those aren't trending up into the right, it's likely a pass on both our sides. And so I would encourage founders to not rush the process because you're dating us as much as we're dating you. And I'll remind founders that the average startup journey lasts longer than the average marriage in the US here. So this is someone you're going to be a partner with for a very long time. Make sure you're doing your diligence on on the VC as well. Is this kind of a good phase where maybe asking for founder references? Is that okay to do kind of during this phase if things are getting a little bit towards the end? Yes. I think that I think that founders should do way more of that than they do. Everyone's on their best behavior during this courting process. But like how does that investor act when things aren't going well? How like go talk to a company that had a mediocre exit or a failure? And how did that investor behave? I would be doing that for sure if I was a founder. The other thing that I think founders don't totally think about is like, who do you want to win or fail with? Like who's going to be someone that you you go ring the bell in New York Sockist James, the NASDAQ, whatever you go ring the bell? Like you're going to have 20 to 30 people up on the stage with you there. Is this a person you want up there with you? Are you going to like look over like you want to be up there and look over and be like, I can't believe I just made that person a lot of money or like that person was such an a hole in that like you want to look over and I love you. Oh my god. Remember when we like figured that crappy thing out? Like that's what you want. And so I recognize not every founder has that many options and sometimes you you get what you get. But like I would do a lot more diligence on the VC if I was a founder. Yeah. That's some good feedback into kind of this other question. We see it kind of a lot. I think founders will be surprised. It's not always the case. But having a fund or sorry around that is slightly over subscribed is kind of what I call it. Maybe you have like one or two checks that you're kind of debating on. You have to move some pieces around thinking about who you'd want at New York when you ring the bell is a good one. But what other mistakes or things do you think founders should index on when making that pick to fill up their cap table? I will say something like I I love the multi-stage firms and they're like great partners stars. I don't think it's great for founders to take multi-stage capital at preceding seed. I think it's too much signal too early. I think it's typically too much capital too early. And I think it's really an option on you and you want to have a partner for whom you're not an option for whom you really really really matter. So I think that it's really important to raise money from firms that focus on your stage. And I would say the multi-stages are best from series A and up. And I would focus on who's a who's a great seed focused investor in your precede or seed round. And the second thing I'd say is this is a tough one. But like I would focus more on partner than brand, meaning the person you're working with and the brand that that person works for. However, there's more mobility and venture than we've ever seen. And so you can't really guarantee that that person's going to stay at that firm. So have that conversation with them. How invested are they at being at that VC fund? Because if they move to another fund, you're going to get assigned a different partner. So I tend to lean towards like to like emphasize partner over brand, but recognize you may end up with like the brand is always with you. The partner may not always be with you. But that's why I love seed focused funds because it's very rare for seems very rare for like seed focused partners to be like jumping around like they are more in later stage. Yeah, that's great advice. I want to go two points we've had from previous folks. One of them Adam Burrows who we both know mentioned that his big thing is if you go with some of those multi-stage funds to them, not that you're a drop in the bucket, but when you're taking a check from a smaller VC fund, especially a smaller fund from a amount of investors or partners in the fund, that check means so much more to you that they will be there and go to about with you because if it doesn't work out, it affects them heavily, where you know, if a if a tier one writes a check and you know doesn't work out, it's it's kind of more the norm. So I agree with that. I think that that's true. Another one here Leo from from Humber, he mentions that he sees a lot of times more often than not. Founders will take a check from a tier one in the very early stage and more often than not, that fund does not follow them, even though that's one of the reasons why they take that check. They think, oh, tier ones giving me a check, they're going to be there for the next series A. I can't remember the stats on there, but it was the majority of the time he's found that they do not follow on. So it's not a reason to keep them in. And that's a big red flag to other investors. Oh, hey, this company was at the table and didn't follow on. And I'll remind founders, they are always there at the next round. Like their bread and butter series A series B like that's where they want, like if you have a billion dollar fund, you need to be writing big checks. So actually saying no at pre-seed and seed is actually good because you give, you make them feel a little bit, except excited about tracking you because oh, they didn't get in. And then you get them in at the right time because they're always still in play. Absolutely. No, that's great advice. Any other mistakes that you see founders make kind of during this final phase where they're wrapping things up and they're closing out their cap table? Not, not, yes, but nothing notable. Nothing notable. That's great. All right. Let's say that they've, they've done all this. They've closed their round. It feels awesome. You get to celebrate for five minutes. Now the work kind of begins and it's this weird 180 kind of flipped in the switch that you have to kind of do. You've spent weeks or months fundraising and all of a sudden it's like you're back in this new mode again. Maybe we go even take a step back. What is your relationship typically with the founder after Dave closed their round? What does that look like for you in matchstick? Well, like we are mentioning, you know, for us, every investment really matters. Each partner does two to four investments a year or so. Like we're, I would say we're like quite hands on, but not like handsy. Like every company we work with, we figure out like what's a custom engagement that makes sense for that founder and where they're at in their journey. I have one founder, for instance, he's incredibly experienced. We check in once a quarter and he's off on his on his journey and doing great. Another founder we're talking weekly. So it really depends on what kind of help and where the startup is that. But like ultimately we're here to be a tailwind for that founder, open doors, help them benchmark. I think it's a huge thing that these that founders should use VCs for is benchmarking. Like what's the standard of performance right now that will raise the next round. And we're always out there understanding where the bar is and making sure that we can communicate that to our founders so that they know, okay, like is this going to be a hard series A or is going to be hard or an easy series A based on on the benchmarks right now. So yeah, I mean, it's just like whatever the founder needs rolling up our sleeves. A lot of tough love in a good way. Like maybe I should emphasize love on the first side, but also we're not afraid to be candid and say, Hey, look, the date is not great here. Like what are we doing about it? So yeah, I don't know. Hands on, but not handsy. Yep. I like that. Is there any other kind of from a high level? I think they maybe the cliche is that typically what happens is they write the check and then the round is closed and the VCs kind of disappear. Is that kind of something like what's the precedent or what's the standard just so you can kind of set the bar maybe for what founders should expect from VCs after they close? Because I think you're an anomaly in what you're saying is maybe more of an anomaly. Any other like from from a high level expectation setting that founders should have. I think it depends on the type of investor. So, you know, if you if you got a multi stage involved at seed, I would sort of expect very low engagement from them and them just like wanting to get updates. If you have a dedicated seed fund investing, I think the standard is at least quarterly board meetings, if not monthly calls and like actually that's good for founders. I think the extra accountability increases performance. I think it forces the investors to pull their weight and try to show up and help and not kind of get away with with not helping. I think the training for founders to be able to run effective board meetings or effective stakeholder meetings at seed and build muscle around that serves them really well when they get to series A and actually have to do do that at in a very formal setting. So I think the standard is like engagement. I think that's the standard also is that VCs are more like I guess more difficult and like then helpful. I don't know that that like I think that VCs tend to take up founder time in ways that don't actually make the company better and are just a cost to founders and they don't realize that like they think they're helping. And so that's the default and so it's rare to find and I'm sure I'm guilty of that too, but I really, really try hard to not do that. Well, you really want to find as a founders of VCE with that high like value to overhead ratio. Yeah, I like that. All right, last question here. What are some of the mistakes that founders make in the first three to six months after they close their round and then maybe on top of that are those the same mistakes or what other mistakes do you see that ultimately end up being kind of the nail in the coffin? Like why did the startups actually fail in the end? Yeah. The biggest mistake I see is companies increase their burn too fast. And it's mostly around a concept that I call hiring in advance versus hiring in a rears. So this is a longer conversation, but the TLDR on it is often you raise money and then you're like, okay, we should hire a customer success person. Okay, we should add two sales people. Okay, we need to add three more engineers and all of a sudden you spend all this time focused on hiring. You take your eye off the ball and serving customers. Revenue starts to dip because you but you think, oh, I'm going to get all these butts in these seats and we're going to figure stuff out. Then you get the butts in the seats and now you got to find work for them. And you are totally you actually didn't really have like a full time amount of work for these people. So then you manufacture work because you're now paying this person to work and you feel like, oh, I'm paying this person. I got to find work for them. And so you end up unfocused. So my strong recommendation to founders is raise the round and don't spend any money for three months and just wait and figure out like what do you actually need? So that to me is hiring in a rears versus hiring in advance because most of your burn goes towards people. Hiring in advance is what I described earlier, which is like thinking you need roles and hiring for them, but not really actually needing them. Hiring in a rears is shoot. I'm the CEO. I'm working 80 hours a week. 40 hours a week of that is task X. Okay, I need to hire someone to actually take this work off of my plate. You hire better for that. You know exactly what what success looks like in that role. And it's a good use of capital. Then because then you can get that was 40 hours a week off your plate or whatever it is and reallocate it somewhere else. So ultimately it comes down to like hiring too fast, increasing burn too fast. And then that does lean into, you know, why do I see most startups fail? It's that they didn't make enough progress on the amount of capital that they had. So really the highest most important ratio for a startup is progress to capital or progress to time, but time and capital are effectively the same thing once you've raised money. And so you just need to be like tracking that ratio very, very closely because once you get upside down on that, you're likely to fail. Nady, this was awesome. This was a lot of information. Paxy to a little bit of time. I think it was going to be very helpful for founders. Where can folks continue to to fall along with you and match stick and continue on that journey? Yeah, match stick.vc. All of our partners are on X and LinkedIn. We've not been posting much lately, but actually a goal of ours this year is to post more. So hopefully you'll see more from us this year. Yeah, match stick.vc, our contact info is on there and happy to meet founders, of course. Love it. Nady, thanks again. I'm sure that we will see each other soon, but I appreciate you being on. Thanks for doing this. Have a good one. Bye.

Podcast Summary

Key Points:

  1. Nadi Zola is a partner at Matchstick Ventures, investing in pre-seed/seed stage startups in between-the-coast markets (e.g., Boulder, Austin, Chicago), with average checks of $1–1.5 million.
  2. She became a VC after founding a company, selling it, and then leading Techstars Boulder; she enjoys coaching founders and helping them achieve their dreams, but dislikes seeing founders fail.
  3. Founders should understand that VCs need them more than they need VCs, flipping the power dynamic; qualification is critical to find investors who already believe in their thesis.
  4. Matchstick Ventures differentiates by offering high signal-to-noise value, founder empathy (all partners are former founders), local support, high Series A graduation rates, and LP backing from charitable organizations.
  5. The fundraising process is broken into three phases

Summary:

In this episode of "Fun Raising," host Matt interviews Nadi Zola, partner at Matchstick Ventures and former Techstars managing director. Nadi shares her journey from founder to VC, emphasizing her passion for coaching entrepreneurs. 5 million, and focuses on generalist investments with growing interest in deep tech, quantum, aerospace, and service-as-software.

Nadi highlights that founders often underestimate their power in the VC relationship, as VCs need founders to exist. She advises founders to qualify investors carefully, seeking those who already believe in their thesis rather than trying to convince skeptics. Matchstick differentiates by providing high-value, low-overhead support, leveraging founder empathy, local presence, and strong Series A graduation rates.

Nadi also notes that their LPs include charitable organizations and pensions, aligning returns with social good. The conversation covers the fundraising process in three phases: building a targeted investor list, making a strong first impression, and closing the round efficiently.

FAQs

Matchstick Ventures invests in pre-seed and seed stage companies between the coasts, focusing on markets like Boulder, Denver, Salt Lake City, Austin, Chicago, Minneapolis, and Toronto. Average check size is $1-1.5 million, and they are generalists with a growing interest in hard tech and deep tech.

Nadi started as a founder, loved building companies and working with VCs, and after selling his company, he became a managing director at Techstars. He discovered he was a better coach than player and later co-founded Matchstick Ventures to write larger checks and help founders more directly.

His favorite parts are working with inspiring, ambitious founders and helping them feel safe to pursue their dreams. His least favorite is seeing founders work hard and not achieve their desired outcomes.

He wishes founders knew that VCs need founders more than founders need VCs, and that founders have more power in the relationship than they often realize.

They are excited about service-as-software, deep tech like quantum and aerospace, and energy infrastructure, focusing on untraditional VC areas and hard tech.

Founders appreciate their high signal-to-noise ratio, efficient use of founder time, founder empathy, local presence, and strong Series A graduation rate. Their LPs are charitable organizations and pensions, which founders find meaningful.

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