Kirby Winfield | Ascend

0:00Kirby Winfield: Pitch, pitch, pass, iterate it fast. Story beats data when the storyline's vast. Visions the ignition, but the numbers steer the ride. Conviction and precision watch investors collide. Hey, everybody. Welcome to another episode of Fundraising, a podcast where we interview early stage investors to get all the tips, tricks, tidbits, anything that you need as a fundraising founder to hopefully make your fundraising process that much easier. And today I have a very special guest, Kirby, the founding general partner of Ascend, an early stage venture fund out of Seattle, where he lives. And we were just talking about earlier is also a hotbed for engineering talent, which we will definitely jump into here as well.

0:45But Kirby, thank you for being on. Can we start with a little background on the fund itself, including what you're investing in, average check size, and then we'll go from there. Yeah, absolutely. Matt, thanks for having me on. I'm super stoked for this. I've been a fan. So pleased to finally make it here. Yeah. So Ascend is an inception stage venture capital fund backing what we call unusual founders with unpopular ideas. And I'll get into kind of maybe what that means. But, you know, just for brass tacks for founders, since I was a founder myself, venture backed twice, you really only care about a couple of things.

1:21One is a 500K check. We will lead. We also will catalyze around with the folks that We like to invest alongside of the bigger checks like Felicia's first round, 0.72, folks like that. And we invest, you know, all over. We've got, you know, certainly a big presence in Seattle, but also probably 20 deals in San Francisco Bay Area, you know, probably 10 in New York. We're in Austin, we're in Boston. And probably equally importantly, we focus on enterprise AI and deep tech. And we can get into sort of why that is and how. But those are the basics. I love that. I'm kind of curious on the, maybe as a quick tangent, what are your thoughts on the investor operator background versus the investor finance background?

2:07Those are the two that we kind of see here. Curious if from your operating background, having founded a company, is that a unique advantage that you would say for founders that are listening when they're looking at like a characteristic to index on? And one of the questions they've been asking lately is whether they should be targeting investors that were founders before or that were maybe not founders before. So I think it's critical to have someone who understands the zero to one journey. and you you can understand it if maybe you didn't live it as a founder but if you were on the founding team or if you've been an inception stage vc for a decade and you've been you know a high eq beloved helpful investor to those companies over that decade then maybe you've learned but otherwise i mean we see it all the time it's just dangerous to have capital from quants at pre-seed or seed you know i always say like you don't want me underwriting growth like that's not that's not you know i don't have an mba i'm not i'm not an hbs guy like you know i was an english major i was going to write the grand novel and then i i tripped and stumbled into into startups for you know 20 years and we did four of them and two went public and then the two i ran and sold uh we raised venture for and all that all that which is to say like again i i'm not there's a reason i don't do you know i'm not running a long short hedge fund i think i'm purpose built and people like me are purpose bill for that first check.

3:31And that's kind of what we see founders resonate with. I like that. And it kind of gives a little background on what you were doing before becoming a VC as well, which is great. We see back and forth on whether or not founders should work with the traditional VC, because I think you mentioned this. And you can have both, certainly, after a while. But when you have the pattern reps of longtime VC and finance, the advice and context that you can give to founders is valuable. but I don't think that anything replaces the founder empathy that you get, obviously from having lived through it yourself.

4:06Yeah. Yeah. I always say like we're in a deal where we were the first check alongside Vinod Khosla and the founder goes, look, you're the guy I call what I, what I don't want to call Vinod and turns out, you know, replace Vinod with any other, you know, sort of blue chip, multi-stage VC. The answer all the way up almost is that most of the things that you need to talk about, you're not going to talk to that VC about. And so you want to find a partner who, you know, has the horsepower and the experience and the capacity and the sort of empathy to have those conversations, you know, and the backbone to tell you what you may not want to hear so that you're not, you know, burning cycles with the person who might lead you next round.

4:49Yep. Absolutely right. I agree. One of the questions that is one of the more favorite once here from founders is what is your favorite part about the job and being a VC? And then what is your least favorite part? Man, there's so many favorite parts. We're lucky. We're lucky we get to do this. Yeah. Yeah. If you asked me as a founder, I would have said I have one favorite part. It's when we exit. No. Yeah. But as a VC, I think my favorite part of the job is when you're in a founder for the first time and you just click over to pitch mode. So you probably have felt this feeling where you're like going to a meeting and sometimes you don't even want to take the meeting based on the merits.

5:31And you might be having a rough day. You might not be excited. And you go in and you're like, okay, now I got to put my gear on. I got to be helpful. Because my goal with every meeting with a founder is I want to leave them with one thing that they come back two years from now, if we don't give them money, they go, dude, when you told me that, that really changed how I thought about things and really helped. That's my goal in every founder meeting. So you got to have energy for it, but you don't expect every time, of course, or even that often at all to be 10 minutes into the meeting and all of a sudden cut them off and go, okay, let me tell you more about how we work with founders, how we support founders.

6:07Let me give you some examples of places where we've kind of catalyzed, you know, blue chip series, AC, and beyond and where we've helped you hire your CFO or your founding engineer. And it's just, I love that feeling because then you get off the call and you're like, okay, who do I know that knows this founder who can back channel? Like, you know, how quickly can I get confident about their capability? Because it's not like I've learned, like, I missed some great deals by over-diligencing at the inception stage. like it's not about me getting smart about networking or or you know chip design it's about me getting smart about the person who needs to be smart about that and just put that whole feeling of like oh my god we got to go like we got to get we got to pull out all the stops like we're we're chasing this chasing this down that is my favorite part of the job yeah i'm going to put a bookmark in that too because we'll talk about what triggers that in those meetings later on here.

7:08What is your least favorite part about the job? I wouldn't say it's my least favorite because I don't mind fundraising and I like our investors a lot. I learn from them. But every, every, you know, every day, week, month that I'm raising money is a day, week, month. I'm not helping our companies. So I'd say that's maybe not my least favorite, but like the most unfortunate part of the job. I think my least favorite part of the job is seeing, it's not seeing founders, It's not seeing companies fail because I need them to not fail because we, as you probably do too, right? We underwrite to a way more than 50 % failure rate.

7:42But seeing, because I've been a founder who actually sold companies and still felt like a failure. And, you know, seeing people just, especially after they've raised a decent amount of money or they've, you know, kind of been hot for a minute or they've just been, you know, true believers and they just stall out and they can't make the journey. That is my least favorite part is seeing the human, the sort of human fallout of this industry. Because it's real. I mean, people, you know, for every person who sacrifices their, you know, well-being and their family life and ends up, you know, making a bunch of money or making a dent in the world.

8:19There are thousands of people who make those same sacrifices and get zeroed out. And it's just, it just sucks. The human element of seeing so many companies and founders give everything that they have to come up short, even if that means that they sold the company or succeeded, it didn't quite hit the goals that they had, it can be heartbreaking. And to your point, it is more often than not. It is more than half the time. Yeah. Yeah, right. You know, when you get into this job, you know, you're going to have a lot of those conversations. And what you hope is that, what does Josh Wolf always say, chips on shoulders, put chips in pockets.

9:00And we've backed companies, founders that have failed in our portfolio for their second go-rounds. And, you know, it's not always the last dance. Yeah, agreed. You mentioned earlier you're investing in, what was it, enterprise, AI, and deep tech. Is that right? Yeah. What are some of the areas specifically within those fields that are getting you excited right now? And or why are those the areas that you're kind of thinking about at a high level? So at a high level, I mean, look, the first startup I was with, there were five of us and we built a portal and we used semantic web search. And so that was AI in 1996.

9:36You know, the second startup that we ended up starting and taking out was use of rudimentary machine learning to, you know, append metadata to 200 ,000 websites that we own and then dynamically call ads and content to those sites. And then I did a big data analytics startup. And then I did. So I've always been doing AI and I helped, you know, Paul Allen launch his incubator at the Allen Institute for Artificial Intelligence. Awesome. And sat there. You were way ahead of the curve. Got there for two years, seeing the pre-GPT wave of talent and technology and got conviction around investing in it.

10:07So I started a fund in 2019 behind that thesis. And I think what we started to see was this. this. So post-GPT, the fidelity of physical world data and sensors and the ability for AI to then take that data and create novel applications has just like skyrocketed. And so seeing that coming down the pike, we invested in Overland AI, which is, you know, I think one of the top 10 defense tech companies in the United States now. And we did the pre-read and we did it when nobody was investing in defense tech and we did it when it was sketchy for me as a an ai software investor to think about investing in something that had hardware and sensors in it now of course they're you know they're they're building vehicles that you know carry payloads to to the front line of of the battle theater and i didn't think i'd be investing in that uh so i guess you know one thing is just like from a from a where's the puck going perspective like it became more and more clear that these software hardware hybrids were going to be, I think, more defensible maybe than some of the vertical stuff that we'd invested in in 2019 to 20.

11:14And also that the capital existed to fund these things. Because I think, you know, historically, those were not always the most favorable sectors to place your bets on as a pre-seed investor. But now with American dynamism and, you know, the sort of the 75 % of the venture capital raised in the past year going to five funds? Well, guess what? All five of those funds love these categories. And, you know, that's not to let the tail wag the dog, but it matters. And then from an AI perspective, I mean, again, I've kind of lived it forever. I view AI on the long, sort of the longer continuum. So I think the GPD is a moment, but, you know, the emergency machine learning was a moment.

11:55So it's, I have a friend, an LP who's advised presidents on AI. And he always says, look, AI is just really, really, really, really, really fast, cheap data processing. And, and it's more than that, but like, so I try not to get too caught up in, you know, what the particular flavor of technology and maybe think more about like, where is the technology best applied? And, you know, one of the, one of the framings, one of the things I like about AI today and deep tech as well is that you, you can still find founders and companies that are doing things that make you sick to your stomach because they're so hard and because they're not obvious.

12:37Because, I mean, we like it when we can't find other people to do deals with us when we get conviction. Like, I'm like, because as it turns out, if everyone's excited about it, we all know this, right? It's probably because, you know, that's the thing that's hot at Series B right now, but you're investing pre-seed. So you're investing, you know, four years ahead of the B at least, maybe three. And these days, maybe two yeah yeah right i mean we've seen it right uh but but uh but i think there's in these categories there's still so many hard problems to solve and so many sort of unseen opportunities and certainly so many talented talented talented people attacking them so that's that and i think we're going to see more and more of these unlocked over the next couple years for sure yeah yeah did you ever read the three body problem yeah yeah so it's like i I always think about AI or technology writ large as sort of a sofa on unlock.

13:32Unlock, sorry. It's just this idea of there will be a moment where energy becomes ubiquitous and cheap, if not free. Where disease is entirely curable or preventable. I just believe those things will happen on a long enough timeline. It might not even be that long. Yeah. I think within our lifetime. Yeah. I mean, I agree. Now, can we keep society together until those things happen? That's probably the harder challenge, which is crazy to think of. But anyway, sorry, we're drifting on. No, it's all good. It's a good conversation. Last question here before we go into the fundraising process itself, a little time for you to shine here.

14:13Why should founders want you and or Ascend on their cap table, especially in these early stages? Yeah, I mean, I think, you know, it's hard because I'm kind of intellectually honest to a fault. And so I think a lot of folks will say the same things. You know, we've helped people land their founding talent, their first engineering hire, whatever. We've connected people with their seed lead, their Series A lead. You know, we serve as the sort of consigliere of the, you know, dark nights of the soul that founders have because I've been there. But, you know, I think honestly, if you're the kind of founder who finds my approach to our relationship to be sort of, it's vibes.

15:00Like, look, if you don't think I bring value in the first meeting, like, then you probably shouldn't take my money. Or if you don't walk first meeting going, I want to talk to him again, then you probably shouldn't take my money. Like, but, but my bet is, and then if you were to ask around, you know, the market or, you know, our, certainly our founders, the ones who have, you know, raised hundreds of millions of dollars and the ones who have failed, like, I think you, they would tell you they're happy they took our money and that we've been the most helpful, active member of the pre-seed cap table and almost every one of those deals, if not every one of those deals.

15:32So I guess I would say, you know, take our money because social proof, because I think increasingly we're a strong signal to the market. You know, our companies are backed by Founders Fund and Co-Sla and Lightspeed and Menlo and 8VC and the folks that you'd want to work with. But, you know, really just take our money because you think you want to work with me. Yeah. Sometimes at the end of the day, that's what matters most. Right. Yeah. It's a long game. you want to it's you know we talked about this a lot on the show where it's a lot of vibes based it's you know especially at the early stage there's a lot of vibe space for sure well you got it i i talked to another investor he said and he said something interesting which is like you got to just want to talk to this person when you invest in a founder you have to want to take their call it just isn't gonna like and the later you go in in the capital stack the less that matters, right?

16:25It really doesn't matter almost at all past series B or C. But at the earliest stage, because you know you're going to be in there. I mean, if you care about founders and you care about your reputation, which you have to in our business, because it's all you have, so you don't have more need to do anything with, you go, well, I'm going to work my ass off for this guy or this gal. And for me to do that, for me to answer the bell every time, I need to believe in them and I need to really, and I didn't like them and I didn't want to spend time with them. And I, and so, you know, I think founders need to think the same way.

16:58Agreed. All right, Kirby, let's jump into the fundraising process itself. We break it up into three parts on this show. The first is getting in the room. A lot of founders listening may not have the, the Rolodex or the email list or the contacts to just jump right into an inbox for a VC. So getting in the room, getting in front of a VC is very important. One of the things, though, that we want to talk about before that is, do you have any feedback for founders as they're thinking about who even to reach out to? A lot of times founders will just go to some sort of lists, almost like VC sheet, and just look at the top names, all the ones they recognize, the Andreessen, Sequoia, Founder Fund of the World, and they just put them at the top of the list and they just start email blasting.

17:39But I found that the best founders can go a little bit deeper and characterize the right people to reach out to. Any advice that you'd give founders as they're trying to think about who they should reach out to in the beginning? I mean, my advice would be to reach out to figure out which VCs you have a warm connection to and reach out to them. I think at the beginning, that matters way more than like any sort of programmatic outreach, which I hate and highly recommend you don't do, which we can get into why. But initially, Essentially, you just need to train yourself on what it looks like to get the intro to the VC and then how you carry that intro to a call, to a follow-up.

18:21And like, what is a conversation with a VC? I mean, if you're really starting from scratch, what is it like to talk to an investor? Because I'll never forget as a founder, the first time I walked into a meeting with the investors, some investors that I knew, one that I knew in particular, I was like, we were bootstrapping. And I was like, this is just a friendly meeting. and uh it was on a monday and it was on sand hill road and i walked in and it turned out it was a partner meeting oh wow and he you know my friend had told his partners like hey these guys have done you know startups before i'm like they're doing a new thing and and i was like yeah i don't know if we're going to raise venture so clearly we did and didn't raise it from them because i didn't have the right like so so i think just learning like what does that feel like what what That is because the other thing is it's so different telling a story to a VC versus a customer.

19:14And all you've been doing is talking to customers. You're so proud of all the things you have and the features and how smart you are. And you're going to try to tell the VC all that stuff and they're just going to puke because they just want you to make it simple. They need to remember one thing about your stupid meeting. Like stop with, right? And you just won't know that until you do that enough. So that's a really long winded way of saying that back into it by like just any anyone you have warm connections to talk to. Angels, if they're, you know, like serious angels, but really there's nobody there's no way to replicate like a venture venture mindset.

19:52So I think that's critical. Yeah, just getting the reps in, getting in front of as many VCs as you can. And the other thing I wanted to call out that you mentioned from earlier is it is almost more important to get the warm intro than the cold outreach to the perfect investor. the reason why is that oftentimes what'll happen is if you get the warm introduction to an investor even if they're not interested in what you're investing in that person that investor probably has a network of other investors where something might come to mind for them so if you get a warm introduction to an investor they could very easily take the meeting themselves and or top of mind go i know somebody who would be interested in this and then they'll forward it along which is you know it's a warm intro from a warm intro but that still can be better than a cold outreach i think that i think the thing that almost no founders know is if if you meet a vc and they are impressed impressed with you you know maybe they can't invest for whatever reason but they're impressed like like wow they look good introducing you to their friends and the people that they want to impress.

21:01Like your, your job is to, in any meeting with any investor, have them walk away going, holy shit, like that, that woman is backable. Like that woman is smart. That woman is going to make me look like I've got the best deal flow in the world when I share this intro. That's why you do, you just got to get in front of investors. Yeah. And it's one of those things that you just get better at with every single meeting and every introduction. So the more that you can do high volume, the better for sure. Let's talk a little bit about the process of pitch decks is maybe the right way. But even before then, I like to call them blurbs.

21:42I think blurbs are one of the most underrated things that you can do kind of during this phase, even with a warm introduction. Because you mentioned earlier, investors just want to be told specifically and succinctly and not in a thousand words, what it is that you're doing, why it's worth their time, all these different things. What are you looking for in that blurb or that, you know, the one liner, one paragraph, the forwardable email, the piece before the pitch deck to get you excited to even dive into that pitch deck? What does a founder need to include in that? I mean, shockingly, they need to lead with who they are and a hyperlink to their LinkedIn page.

22:22It's left out a lot. phenomenal to me how few people, I mean, it's like, I mean, it might be half. I don't know. It's crazy. We're investing in you. So, and you don't - What do you say to the Gen Z people out there though, that maybe don't have a LinkedIn account and they're thinking, well, do people even use LinkedIn anymore? My son is 19 and him and every single one of his college classmates and high school friends all have LinkedIn pages. So, I mean - It's feedback I've gotten before where they're like, oh, LinkedIn. I just didn't think that That was something that people used. I'm like, yes, your investors use it.

22:54Yeah, yeah. I think it's more likely that you will be converted to LinkedIn than you will convert us all to some other method of finding out who you are and what you did. Of course, if you're special special, then you're special special and I'll go to your, you know, I'll go to your GitHub, you know. And to that point, though, that means that you should also spend the time to make sure that your LinkedIn profile is also not just an afterthought either. I mean, I saw this the other day with a guy that I actually wrote a term sheet to. And I was like, before we go out and share this with other investors, like, you got to update your LinkedIn.

23:31Because the vast majority of us, the first thing we do is we go to the LinkedIn and we take a snapshot. And a lot of times that snapshot, I mean, I'll tell you that, again, in the context of what's the blurb, I don't know what the blurb is. But most of us aren't reading the blurb. Like, we don't get to the blurb. at this point, I don't even have time for your blurb. So you're going to their LinkedIn first before you even read anything else. Yeah. Because I need to find, I need to figure out if you're credible and everyone's definition of that is going to be different. But your background and work history are good indicators of credibility.

24:09Yeah. And I think - There's no faster way to just get a snapshot of that. You get a snapshot and you almost never hard pass on that, But it sets it up for then the rest of the board, which, you know, may or may not have to be less or more convincing based on what your profile is. I always say like there's three things that matter. It's, you know, what team technology and traction. And the more you have one, the less you need of the others. So if I go to your LinkedIn and it turns out you're Steve Jobs, you know, part two, then, OK, I don't care anything else. If you're not, then I have to look at, OK, well, what what what what are you chasing?

24:44What's your vision of the world 10 years from now? like, you know, why is it unusual and audacious? And if it, and if what you're saying you're going to do about it to effectuate it works, like, does it matter? That's the question that I want to answer. And then at pre-seed, I don't even want to hear about your traction. Like if you got a pilot, great. It's almost, but almost for pre-seed investors, I don't know how you feel, Matt, but like, I almost, I'm like, if they have, if they have a little revenue, I'm almost like, because now you've started the journey and maybe you have a bad customer or bad customers.

25:14And like, I really want to be there before that happened. We can talk about it and I can help you kind of think about shaping it. The further I've just learned, the further it gets towards seed, like the less likely I'm going to see an outlier deal. Yeah. You know what I'm saying? Like, we got it like, again, I'll speak for myself. I got to be betting while you're still at your existing job. you know i gotta be betting before you've got your deck like i've gotten you betting so early because if you're if you're right then you're not going to talk to me six months from now and and so that means that if you are talking to me six months from now it's negative signal like if you've got 200k in revenue i'm like okay if you started a year and a half ago i'm like well why are we talking like that's been a weird learning in this job actually because because i think it's it's it's it's intellectually like it's not what you would initially think you would think oh more traction de-risked well you know i don't care about being de-risked i care about opportunity for exponential upside and if you're showing me that you don't have it the longer that you've been showing me you don't have it like the less likely it is you're going to get it this is also something that founders do not understand about venture the clock starts and Yeah.

26:36I like to talk to all of our founders. It's velocity and momentum. And you need to be able to show both of those things where if you, to your point, if you show 200 ,000 in revenue and it's a year and a half, that's very different than even 100 ,000 in revenue or 50 ,000 in revenue in two weeks. Like we'll take the shorter timeline than that. Even then, whenever I've met founders that are like, we've been doing this for three years. And over the last three years, we've gotten a million in revenue. It's like, well, it's a long time. And again, it's like, well, why now? But then you dig deep and you're like, oh, but that million came within the last like two months.

27:10You guys started two months ago. Like let's change the narrative here. I love that. I love that, dude. Yeah. I love it. Because also the mistake people make, well, now we're going to go off to something else. But like they raise money and then they go, we got to grow. oh, we need revenue. And I'm like, no, no, no, no, no. You need to get ready to make a lot of money in a short period of time. Like nobody cares what you do after your raise. You get a six to 12 months grace period. As long as the four months before your next raise, you're going from one unit to three units to six units to 12 units to 20 units.

27:44Yeah. And you need that velocity. Yeah. Yeah. You're totally right. Yeah. Really quickly on pitch decks. you've already given some good examples of the things that you're looking for, whether it's in the blurb or the pitch deck, any high level advice on just the pitch deck itself, maybe less about what to include, although you can add that in there, but maybe how it's presented or any other mistakes or common mistakes that you see with pitch decks. That's a hard one because some of the best companies have the worst decks. I know. That's true. So it's sort of, I think the pitch deck question is a lot like the investor update question.

28:22oh yeah you can find data that you know there's correlation and and there's some correlation and potentially no causation like so so whether you send updates or not like i i prefer you do because it makes my job easier but it's not going to make your company different unless you're unless you're preternaturally like disorganized or whatever which case the discipline helps when it comes to pitch decks what i will say is like just don't it's almost like what not to do don't get creative with the structure don't have more than 12 slides do have the 12 slides that doc send says you should have based based on their billions and billions of decks worth of data know that investors spend an average of 20 to 30 seconds on your deck know that if you do get to present it in a partner meeting because you're certainly not going to present it on a call that often.

29:17You might if that's your style, but we don't like it, right? So it's kind of a leave behind. It's kind of you know, now it should to the extent that it guides or reflects your narrative, it's very important. So I would say there's the pitch deck, the physical artifact, which, you know, just follow the rules and make it look good and, you know, I don't know, whatever. I found that people can only make the pitch deck that they can make. I was like a B-minus deck maker. There you go. If it's too good, sometimes you're like, something's wrong here. Sometimes there's, yeah, when you get a pre-seed deck that looks like a, you know, IPO, pre-IPO roadshow deck, there's.

30:00So, but, but, but I think, I think the things that you do need to remember, again, your job is to leave the, the, the recipient of your deck with one idea, which is like, these, these are the people, these are the right people to do this thing. And this thing matters. And this thing is X. It's a marketplace for pet owners and caregivers. It's a verification platform for generative AI. it's a like people it's again shocking how few people realize that not only they have to be clear about that at the very beginning of the deck or else you lose people for the whole pitch you just say what you're doing and you need to have a logical progression but but that's the whole point that's all you're supposed to do it's not the goal the goal is to get another meeting exactly yep let's talk about the the meeting itself uh because that's an important part we We kind of call that the phase two here.

30:58So you've impressed them enough to get that 30 minutes of time. You mentioned earlier, one of the things that you love the most is when you have that moment in that meeting where all of a sudden you go, I need to invest in this founder. I'm excited to invest in this founder. You start going into pitch mode yourself. What does it take or what is it that makes that click for you during those meetings to get you excited? i mean if i could answer that question you know super accurately i'd i'd probably i'd if i i so so the answer is i don't know it's it's there's there's sometimes sometimes it's like a subtle indicator and i'll be i'll be willing to admit that i may have been played once or twice right because you can you're a good poker player as a founder you can kind of there are things you can do but you gotta be real careful because it can be corny and obvious but if and also you kind of have to have the cards.

31:49But, you know, when I hear like, if it's someone I already like, I'm excited about, but then I also hear like, you know, we've been talking, we've been talking investors for, for like the last week. And, you know, it feels like, you know, it feels like we'll be wrapping this up in a week. Like that's something that sort of peaks you a little bit. I think that what I was going to add on top of that is that to your point, it's hard to build the checklist of like what you need to get excited because it's different every time. But you mentioned earlier, something that I think is important is you mentioned that what was it?

32:22The three T's with, you know, team traction. What was one of the other T's? Technology, which is just technology. Yeah. Almost the idea of like what you're building. And you're exactly right that sometimes if you have one of those things that is, you know, top percentile, the other ones don't matter as much. And it might be in this case that that person's background or that person's team or just the way that they're going about it is so good that you get excited to invest. One question maybe to add on top of that, maybe as a replacement question is, do you ever see it where does one of those things need to spike?

32:54Or if all of those things were just good, like B plus, is that enough? I guess, is it, do you need an A plus with one of those? Yeah. Yeah. Yeah. Yeah. So I was thinking about this recently and I realized, yeah, no, one of them needs to spike you have to be uh and it's so it's so painful this job is so painful because you just have to learn through you know reps and and it's like i think my first fund which i love the founders we backed and we've had a lot of successful companies in that fund but if i look at on on the on the whole like i backed a lot of folks and and teams and and companies that, yeah, they were pretty damn good on all those fronts.

33:42And this was, yeah, Jake Storm at Felicis was the one that introduced me because they used the term spikes. He's like, we look for spikes. Yeah. Yeah. It matters much more that you're really, really, really good at one thing. And I'm an example of this as a founder. Like, I was very good at most things. And I was not insanely good at anything. Like, and which is great if you're like on the founding team or if, you know, before if you're a GM or if you're running a PNL or, you know, like there's all sorts of jobs that I was suited for being a VC where I don't think you need to be quite as spiky, but, but I was not, I didn't have it.

34:24And that's why, you know, we sold companies and they were fine, but we were never going and go parabolic, no matter how good my technical team and co-founders were, which is kind of like did them a disservice. But yeah, and it's also that thing you go, yeah, you just get more comfortable as you go in this job, investing in spiky folks. That's really well said. Yeah. Are there any mistakes that you see founders make during some of those intro calls where you're maybe meeting them for the first time? I mean, never have another person on the call, never have like an introducer on the call or an advisor oh yeah if someone introduced you and that person thinks they should be on the call just no that's it it's it's the death knell you can't do so you it's got to be you and and if it's to you and your co-founder have a reason for your co-founder to be there like if they're just sitting there tag team it yeah if they're sitting there watching the show that's it's or answering emails on the side yeah it's a net negative and it also shows me that you're not valuing, you know, your time, like you're not valuing your time or their time.

35:31So it's a negative signal. What other mistakes people make going into your pitch deck without asking? Yeah, just reading through it. Yeah. Or without asking if the investor wants you to, like, I mean, I'd much, much, much rather just have a conversation with you about who you are and why you're doing what you're doing. Like there's not, it's not a test and your pitch deck isn't going to help you pass the test. Yeah. Like, do you think it's one of the things that founders asked? One of the questions that we have is should founders ask the questions up front to say, what are you looking for in this meeting?

36:03What are you trying to, what can I explain to you that maybe you didn't see in the pitch deck? Are those types of things that you'd recommend founders kind of lead with as they're going into it? I think this is very subjective investor by investor. My thing is if you are overbaked, anything that smells like overbaking it is a red flag or a yellow flag for an investor. Like, you should be really, really busy doing important stuff. And then, yeah, you have a deck. You made the deck and the deck's like, okay, investor, you want to see a deck? I got a deck. You're on even ground with the investor.

36:42I know it doesn't feel like it, but you you and you don't i hate when they you can't get coach people get coached to be like too brash and interview you as an investor like you ask me to coach him it's fine but like don't be arrogant yeah don't be arrogant but but also like two way too many people are limping in and it's like look no don't ask don't walk in and be ready like walk in and assume that you're going to have a conversation about something that you know better than anyone on the planet and you're pumped to educate someone and share that with someone. That's all. And if someone, and if that person needs you to walk through a deck, be ready to walk through a deck.

37:20But, and, and if, you know, I think it's good practice to walk, to assume not, and then, and ask at the outset, like, you want me to walk you through a deck today? Or should we just have a conversation? And because the conversation is where we get excited. That's where we find out you're the person. We're not backing decks. Like, I've never been excited to invest after a founder reads through a deck. Not once. Right. And I think I read, I also mistake being too precious with your deck. Send it ahead of time. If you're asked to send it ahead of time, send it ahead of time if you're not asked. Because then I can scan it two minutes before our call and I'll be smarter.

37:58I'll be ready. You know, investors are not spending 20 minutes preparing for your intro call. And a good deck gets me there fast. So, yeah, when it's not there, you're only disadvantaging yourself. Nobody's going to steal your idea. Maybe series B, like, again, when scale up competitors, all that, but early on. Yeah, no, I agree. What are some of the mistakes that you see founders make as they're closing up? So one of the benefits of being an early stage investor is that you are typically there first or early and then you get to watch them close out the round. So I find that these investors typically have a good wisdom around the right way and wrong way of finishing out that round.

38:41What are some of the mistakes or it could put in a different way? What should founders be aiming for when building out their cap table? I mean, that's a big question. I think a mistake founders make in general when they're raising rounds is that they don't have enough VCs on their hit list. Like they just don't, they don't stuff the pipeline. They get, they get, you know, optimistic. So I think when I've seen people struggle, I can't remember the last time we had a founder that we, you know, were first checked into that didn't close the round, but, or, you know, or we come over subscribed even, but like when we've seen people struggle, it's when they think it's like, okay, well, you know, Kirby's in.

39:19and then we've got, you know, two other 500K checks. We've got a million dollar check that we've been talking to. We think they're probably in. So we're not going to start any new conversations. And it's like, well, did they, why are the money they signed at Docs? Because, you know, until that happens, go and talk to everyone that you think would be awesome. Exactly. It doesn't hurt because they could always come in later or they could get excited and oversubscribed. There's no downside to talking to more investors, except it's, you know, it takes your time, but that's the job. So I think that's a mistake we've seen.

39:46I think something that people, I've seen people do that I like is traunching. And so especially if - It's like closing. So that's the idea of closing kind of as you go. Yeah. Because here's the thing, and nobody's going to feel bad for me. They never feel bad for us. But I literally, I don't think I've ever asked a founder at the pre-seed when we're committing to invest who else is investing. I just don't care. But because of that, I'm taking the most risk of anyone on the cap table. So like, give me, you know, if you're concerned, if you want the valuation of your round to be 18 post or 20 post, okay.

40:25You know, get us in at 12 post and close, close a tranche at 18 and close one at 28. Like, and that's a great catalyst because founders are always like, well, how do I get people to close? Like, well, tell them that this tranche is closing. That, that aside from having a term sheet from like a tier one, tranching is probably the single most effective way to get people to sign the docs like it's it's great and and the thing is you just take where take where you want to be subtract three that's the first tranche add three that's the second tranche and and you'll raise half your round overnight and like i don't know why more people don't do it i think it's uh because i did that when i was raising i think the downside there which you don't really maybe it's a good problem to have, but you do end up getting cranky investors as you go through because you will have investors that are, you know, as long as there's maybe flexibility as a founder, but if you're meeting with an investor and it's like, oh, last week, this person wrote a check at this value.

41:25Well, I want that valuation. And so I would say those that that's not a sophisticated investor. Yeah. Like, I mean, it's true. I mean, you know what? Like, I'm like, we just did a deal actually where someone else had committed before us, which does not happen that often, but we really liked the founder. And we paid 25 % higher than the person who had committed before us. And I didn't ask whether that was a week or two weeks ago. It doesn't matter to me. Like, fair is fair. I should have spent four months with the founder. I didn't. And by the way, when Matt writes a check, by virtue of that, the company is worth more money because you've now put your name on it.

42:05You've done the diligence. They can look at your portfolio. Other investors can look at your portfolio and feel de-risked. So I think the time thing is a total fiction. Yeah, I like that. All right. Maybe last question here because we're butting up on time. A lot of times we see founders, they think about the fundraise, but after the fundraise is when the work really begins. And a lot of times founders stumble a little bit after because there's almost a chain shift. Their mental model has to change almost immediately. What is some advice and or maybe some mistakes or pitfalls that you see founders make immediately after they close the round and maybe for the first few months after?

42:44Like I said, I think one is just getting obsessed with revenue and closing customers at sort of all costs. And this is all pre-seed advice. So obviously, you know. Of course. Yeah. First check. Yeah. First round is just closed. Yeah. Yeah. I mean, I think people also make the mistake of feeling like they need to hire a team in air quotes versus like add the most insanely talented people they can possibly find and take their time to do that. Like just build and do customer development. You can do customer development when you don't have a product. Like do customer development, hire a sick team.

43:17And if those are the only two things you do for six months, you're going to be in great shape in month seven. I mean, so I just think people get it twisted and they feel, especially first time founders. And I've done this, you know, you're like, well, I have the money. I guess I got to hire a marketing associate and a customer success person. I'm like, you didn't even have a customer, you know? Yeah. You're hiring a marketing person. Got to hire HR to then manage the people that I don't have yet. Yeah, it's the worst. And, you know, I mean, we've even, like, unless it's a co-founder, I don't want you hiring a CTO.

43:49Like, there's just a lot of that stuff, I think, are common, pretty common mistakes for folks who are doing it the first time and haven't been around. like haven't been around great like i think it's such an advantage and this and people always like oh well why do vcs always just want to back like people that were at a successful startup early like what does that have to do they got lucky i'm like well they got lucky but they got lucky to see what great looks like like that's how if you're not like what are the odds that you stumble on that yourself you know yeah but if you know if you were at spacex you know for the for the development of Starship and you worked on a project directly, like, yeah, I think I'm going to be excited to back you and your team out of SpaceX.

44:31It makes a difference. Knowing and seeing what success is, even if you were a smaller part in that success, it carries over. It definitely does as a founder. Kirby, this was awesome. We covered a lot in a little bit of time here, and we could have gone on for at least another hour, I think, as well. Thank you so much for being on, where can folks continue to follow along with you and the fund? I am on a Twitter hiatus, which, yeah, it's self-enforced. Good, that's healthy. Nobody else made me do it. But yeah, I'm on LinkedIn, Kirby Winfield, and our website is ascend.vc. And if you want to see the reason that I quit Twitter, you can go to at Kirby Winfield.

45:15Oh, boy. No, no, no. Now I'm going to I have to. Years and years of compounding rants and good stuff. But anyway, yeah. And I'm just Kirby at Ascend.vc is my email. If anyone wants to hit me up, happy to. There you go. Warm intro preferred though. For sure. But asynchronous email responses will be delivered. There you go. I'm fine doing that. Perfect. Well, Kirby, thank you again. I'm excited to maybe chat again soon. We shared before this that we have some Colorado connections, which is always good. So hopefully maybe next time we'll do this in person. It's been a blast. Thanks so much. Absolutely.

45:55You can tell I get a little overexcited. I love this stuff. So hopefully I didn't jump through the screen on you, but this was really fun. No, definitely not. No. Awesome. Thank you again. Let's chat again soon. Sounds good. Bye. Bye-bye.

46:15Kirby Winfield: Three Line's Fast, Visions the Ignition, but the numbers steer the ride. Conviction and Precision Watch Investors Collide!