Ashley Smith, GP & Founder at Vermilion Cliffs Ventures: From Startup Operator to Venture Investor

Scott Smith: I’m excited to welcome Ashley Smith. She is the GP and founder of Vermillion Cliffs. a venture fund. Or maybe I’ll just say I’m excited to welcome Ashley Smith, GP and founder of Vermillion Cliffs, known for driving growth at Twilio,…

Scott Smith: GitLab, GitHub, and being an investor, entrepreneur, operator, and I’m excited to have her talking with us on our podcast today. Welcome, Ashley.

Ashley Smith: Hey there.

Ashley Smith: Good to see you, Scott.

Scott Smith: Yeah, so just to start off with, Ashley and I have known each other for quite a long time. and I worked together at a startup and company called Pars where I was a lowly account executive. She was the director of marketing and she basically taught me how to do so many amazing and incredible things in the startup world and it’s been fun to get a chance to bring her back. So actually we’re going to talk about a bunch of things today we talked about your venture fund that you’re going to be launching this week soonish. You want to tell me a little bit about that first?

Ashley Smith: will tell you I am unmanageable. I don’t like working for people and that’s okay and I’ve always wanted to do my own thing and so angel invested for a long time in a very early stage company. So preceded and seed and am launching my fund it’s called Vermillion Clips Ventures and I do preceded and seed dev data infra security really anything technical created by technical founders. and I’ve been going for about a year and a half now, fully raised. which was really interesting. It’s a whole different conversation. and have backed about 25 founders already. So, it’s been really, really fun to work across a lot of different companies that have been embedded into one. and it really does feel like, I’ve found my place in this weird world of tech.

Scott Smith: Amazing. I think the fact that you have described yourself as unmanageable that should probably be…

Scott Smith: if you ever write a book that should probably be a great title for a book.

Ashley Smith: Yeah, it’s funny you say that.

Ashley Smith: We were working on the launch and I’m really excited for the launch press and everything to go out, but I wrote this and you’ll see It’s a 21page manifesto. just as I started writing and trying to explain how I got into tech and where I’m from and all that, it just got longer and longer and longer. And so, the press team that’s helped me out was like, you should really make this into a book. And I was like, I’m pretty private. I don’t know if I want to do that, but I do think unmanageable is probably the best way. It is the singular word that describes me. I think Yep.

Scott Smith: the best tech tech companies in the world. And how did you get in?

Scott Smith: How did you get started with even just where did that begin? How did you get there? High school, Ashley, maybe

Ashley Smith: Yeah. I mean,…

Ashley Smith: No, for most people, my dad was the CEO of Twilio. I’m kidding. it’s not how I got in. So, I you’ll probably hear my accent. it es and flows these days because I’ve been out of the South for a while. I think Scott, you probably remember it being a bit stronger. I don’t know. I grew up in South Georgia. Technology is not really a thing down there and still isn’t. It’s a wonderful place. But I had big dreams for some reason. I don’t know why. I can’t explain that. started coding when I was 12 and ended up going to Georgia Tech, which is a great state school and a great engineering school, biomedical engineering, computer science, and just found my people. I had always been the weird kid in the room reading books and playing on my computer. And I got there and I was not the nerdiest person around which was very new.

Ashley Smith: And yeah, it made me realize I really love technology. And so after college, I don’t know when you entered the workforce, but it was right during that the giant housing crash and everything was going wrong and there were no jobs and kind of similar to what we’re seeing now.  But I started just applying for entry-level jobs at startups because a good friend of mine was got to Y cominator doing his little startups. and I just started applying and I was either overqualified or underqualified for everything. None of them made sense really. but the one that I applied for, got an interview for and got hired on the same day was a entry level job at Twilio.

Ashley Smith: which was basically answering the phone was the very original job. It was just like some people are calling us, customers are trying to please talk to them back. and I’m not extroverted. but I figured it out. And so from there, I started going to all the developer events. I started doing all the website working on the emails that would go out to developers and just learn the ins and outs of go to market from an engineering perspective. So, it was by chance that I got that job. I didn’t know anybody. I’m so proud that they interviewed me and took the chance on this person who they didn’t know. and that’s how I got into tech,

00:05:00

Ashley Smith: the very first startup role.

Scott Smith: and…

Scott Smith: especially developer focused products, right? Julio is one of those types of companies and…

Ashley Smith: Yeah. Yeah. Yeah.

Scott Smith: you continued to take that type of expertise and enhance and refine it as you went further and further Okay.

Ashley Smith: I can’t imag I appreciate a lot of the startups I see that are selling to other markets or building for other markets. I love selling to and marketing to and building for developers. it as soon as I got a few months in and it wasn’t strategic. I like engineering things. I should work on there was no strategy involved. frankly I think people when they were from the age of five I knew I wanted to build a developer product and blah blah. I think that’s all not true.

Ashley Smith: I think I found my way into it and then when I got there I was like this really works and this fits and from there I never branched out like I just stuck to developer facing products and what I know and I got some feedback a few times of you should go do consumer that way you have a broader view on things and I’m like I don’t want to do that but yeah so I’ve always worked on technical products primarily in technical products I can invest in stuff that’s a little bit outside of that. enterprise software is kind of the bucket. but yeah, mostly people building tools for developers.

Scott Smith: to sort of shift and transition from Twilio where as far as I understand you’re more individual contributor were you I don’t know if you were managing people to parse where you were leading the whole thing Yeah,…

Ashley Smith: I’m a little bit bossy, so even if I’m an IC, I’m still kind of everyone around me. and that’s okay.

Ashley Smith: But I was an icy across a bunch of different things, but I was creating the thing at Twilly. I was creating the thing and then passing it off to someone that we hired to take that on. I did manage someone she was incredible. I think she was an intern. She might have been full-time. As you get older, your memory goes. I don’t know if you know that yet. so yeah,…

Scott Smith: I don’t have that problem yet. I’m only like 39, dude.

Ashley Smith: I don’t know what you’re talking about. Me either. so yeah, I managed someone at Twilio, but I wasn’t like we had an incredible CMO, Linda Smith. we’re very close. And I was so lucky to have her because she really did teach me the parts of enterprise marketing that I had never seen as it applied to a technical product which are very different than the developer love, go build a great product that developers want to use.

Ashley Smith: When you layer that enterprise marketing on top of it and enterprise sales, as you know, it just kind of supercharges the ability to actually grow a technical product.

Scott Smith: The first one it was Halloween and you came into the office wearing a dragon or dinosaur outfit onesie.

Ashley Smith: How dare you? Yeah. Yeah.

Scott Smith: Yeah, that was incredible. I thought, okay, this person who I thought was hardcore and intense and I was a little bit scared of, it’s like, she’s totally cool. She’s totally chill. And it was one of those ways that I don’t know was able to see you as a coworker friend and that was super cool. and then on top of that, the thing that always surprised me with a lot of your efforts and work was that somehow you figured out how to get us into Techrunch top of YC over and over and over. And I didn’t understand it. I still don’t understand. how did you figure out how to do that?

Ashley Smith: I really don’t think it was me, right? I mean, I take credit for doing the actual work,…

Scott Smith: Okay. Yeah.

Ashley Smith: I’m the person that did the thing, but pars as a product was so compelling at the time. we’re riding the wave of AI. We were some people were riding the wave of crypto and that world. Before that, there was this whole big data push, right? every single few years, we see the new thing we’re wait we’re writing.

Ashley Smith: And I feel like pars perfectly intersected when mobile took off and people knew they needed a mobile app but they didn’t know what that meant and there mobile developers were still a new thing right and…

Scott Smith: Right.

Ashley Smith: so I think that because we were building such a compelling incredible product as our engineering team was creating fantastic content we were shooting at a crazy rate we just had great tailwinds because of that and so then when I would go pitch I didn’t never had a PR team. People always think that I had a team of people. I had, obviously I’d make Hector go to every event on the planet. and then Our engineers were so great that we just all did it together. but I would just go cold email these Tech Crunches and Business Insiders and whatever the places we were getting coverage.

00:10:00

Ashley Smith: And then when Hacker News, I think organically people were just excited to see what we were launching. I mean, I think we didn’t have this big voting ring of thousands of people going and uploading things, right? I would definitely be …

Ashley Smith: “Hey, we just launched on Hacker News. Make sure you go read it and upvote it.” But that was just internally to our team, which was only what at the time 10 15 people. So we weren’t gaming the system. we were just launching actually unique things and doing it at a rate that was insane. That team was just,…

Scott Smith: Yeah, it’s tiny.

Ashley Smith: I’ve said this publicly before, that team was just one of, if not the best teams I’ve ever seen, even today. Yeah. Right.

Scott Smith: Yeah, I think I’ve worked for a lot of engineers at many different companies and…

Scott Smith: I think the desire to market and evangelize and document and talk about what you’re creating was I was like, ” wait. you’re not supposed to be doing this.” Or at least I’ve never heard of any engineer…

Ashley Smith: It was amazing. Yeah, absolutely. Yeah.

Scott Smith: who wants to do this kind of stuff.

Ashley Smith: I mean this day I mean at other companies I would always beg for engineering resources to write a blog post that would and I would be like hey can we put in the OKRs that if you want to write a blog post you can do that and you’ll get bonus whatever at pars I would have them coming to me with content saying hey can we maybe post this and I was just like absolutely because nobody wants to respectfully to you and nobody wants to hear in the developer world nobody wants to hear about some random very businessy thing as it relates to developer products.

Scott Smith: Which is Yeah.

Ashley Smith: They want to hear from the people building it. And I think that was always just so powerful from the Pars team. And Twilio was the same way. Twilio, we had some great content coming out. and our engineers were writing, but Pars it was like every single day I’d have something to talk about and it wasn’t me having to create all the content.

Scott Smith: Which is just super nice. So that’s actually …

Ashley Smith: It was just a very special team to be on.

Scott Smith: sorry. Go ahead. Yeah. Yeah,…

Ashley Smith: I think it’s crazy.

Scott Smith: absolutely. I think some of the things I love the most is I would go work out with one of our engineers, his name is Andrew. He would mock me relentlessly because I couldn’t do as many pull-ups as he could. We had an engineer named Hodny who I’d go run with and it was like he was the most incredible engineer, but he could also just run forever and he just destroyed me every day.

Ashley Smith: It’s not fair.

Scott Smith: So, I think you make a really great point about the team building a strong team culture. You’ve worked with many great companies, and I imagine at least you have some sense for what makes these teams really great and some of these individuals so strong? do you have any ideas or thoughts on how to build a great team culture? what have you seen? how do you do it?

Ashley Smith: one of the strongest CEOs that I’ve ever been exposed to. and all my CEOs have been incredible. So, I never realized that sort of startups could fail because it was just like bam bam. All my teams are great. and we had good traction. But, I watched Jeff purposely hire people that if they wanted to spin out and start a company, they could. And they took total ownership of the role they were doing and total ownership of the success of that role.  And so I think there’s something to be said about hiring people that are a little bit quirky, but a little bit over the top in ways that are good and really own the thing that they’re doing and want to do the best that they can at what they’re building. And you kind of see that a lot of the people we work with at Parse now either have their own companies or, RBC’s or they’re high level somewhere or they’re still at Google building really interesting AI tool.

Ashley Smith: there’s just everyone was unique and interesting. I think what I learned from Jeff is one time and it was my mistake. We were interviewing for a role and I just needed to hire for this particular role and the person was good enough but not great. and I said we were probably like a hundred people. I remember saying sometimes you have to start hiring people that are just good enough for the role. And he’s like no we will only hire great. I was and understood and now I so deeply understand what he meant. and I think that everywhere I’ve worked has done that. So yeah, I think we just ended up hiring people that were just culturally a great fit. We had such a unique diverse group of humans from all different backgrounds bringing very different perspectives at PARS and we all really had fun. there’s not a single person that I probably couldn’t just go hang out with even today.

00:15:00

Scott Smith: or at least we wouldn’t say it on the recording way.

Ashley Smith: I like spinning through my head. I’m like is there anyone I don’t want to see? And it’s like we were having pars meetups until not recently but before the pandemic and I always think we should do a pars meet up soon…

Scott Smith: Yeah,…

Ashley Smith: because it really is such a strong group of people.

Scott Smith: absolutely. And I think one of the memories that I have that it still annoys me really deeply is we were hiring for a role at Parse and…

Scott Smith: it was just at this beginning stage where we were starting to interview for I feel like it was like a product marketing manager or something like that and we were still our own company and…

Ashley Smith: Yeah. Yeah.

Scott Smith: and maybe it was like an AE but what whatever and I remember we kept bringing candidates to Ilia and Ilya was just like nope not good enough not good enough not good enough and it just drove me crazy I was like dude I’m so overwhelmed like we just need more people…

Scott Smith: but yeah I felt like it was similar vibe with

Ashley Smith: He was exactly the same way and…

Ashley Smith: still is. Ilia expects excellence and if you bring him a candidate and he says they’re not good enough at the time, he probably had a good reason why. And I trust his judgment. and yeah, I think you have to if there’s ever a doubt in your mind that someone maybe isn’t like they’re great for right now but not for maybe the next three years, it’s probably not the right person. yes, Facebook. It didn’t work out.

Scott Smith: Something about Facebook, as somebody who is unmanageable, surrounded by managers,

Ashley Smith: No,…

Scott Smith: Yeah. …

Ashley Smith: I think we for a while.

Scott Smith: you were there for a while, right? So, you figured out how to transition from startup to giant company growing incredibly fast.

Ashley Smith: Yeah. Wow. it’s funny.

Ashley Smith: I just caught up with Julian a few weeks ago and we were laughing at how yeah.

Scott Smith: By the way, for anyone who’s listening, who is Julian? Just to give some context.

Ashley Smith: So Julian was on the business when we got acquired. There was a group of executives that were sort of representative of different parts of Facebook trying to help shepherd par into Facebook. And so Julian was on the business side. And so Julian I think you have to help me with this. He was leading sales partnerships. I think he was your manager at some point. Yeah. He was like And so he was he also expected excellence and I’m walking in from a perspective where I’ve always been queen bee within reason, and I now have someone asking me about metrics and blah blah blah and all these questions from more of a sales perspective. So think about sales enablement versus, community building.

Ashley Smith: But he deeply understood both pieces. But he pushed me really hard to frankly uplevel the way I thought about the way I led marketing and at the time I was more junior in my career and unable to take the feedback. Anyways, so unmanageable as always, but luckily everyone that worked at Facebook at the time early on really wanted us to succeed, were really good to us.  I don’t know if you remember that party We launched something. I don’t remember what it was, but Facebook was I planned this little party. We call our parties and meetups are always great, but they were like, “Here’s some money and a team of people to help you.” And then some pe and it was just crazy. All of a sudden, they had all these resources at my disposal to help me do that. It was at the W in San Francisco.

Ashley Smith: And it ended up just being like I didn’t have to do anything and two weeks prior I was ironing banners and trying to keep everyone’s coffee cups off of the event things and I was the one doing everything and it was just very different to have resources. so from that perspective it was incredible.

Scott Smith: Totally.

Ashley Smith: There’s such good people at Facebook that were at that time great to us. I think the hard thing was I don’t think any of us knew exactly where we fit in to the strategy that is why does Facebook need a mobile app developer platform? and I think that it was tricky to watch that part of it happen. And we’d all come to a startup. We weren’t trying to work at a big company.

Ashley Smith: But the food was good and the people were really nice and I think we made a lot of progress just all of us in our careers and also Pars continued to grow. obviously it eventually got shut down because it does not make sense for Facebook to have a mobile app platform. It just does not and I think a good example of an acquisition like that is the Firebase one which we still see is still going. but yeah, Facebook was good. Hard to be managed.

Ashley Smith: I think everyone started leaving. our founders were jumping to different teams and for me, I just didn’t want to be at a big company anymore, I thought. And then I tried another big company and realized I really don’t want to be at a big company. And then I jump back into early stage because that’s kind of

00:20:00

Scott Smith: Yeah, I think that that whole experience really resonates with me.

Scott Smith: It’s funny when I look back to your point about being younger and I mean it’s not that long ago but I remember how often I would come home and complain to my wife and be like I have to do this or somebody told me to do that and it’s like dude that that’s like what a job is but I think exactly  Hey, heat.

Ashley Smith: Yeah. …

Ashley Smith: And we were being you and I and Hector in particular were being flown around the world to go to developer events that I could plan and it was amazing and we got to F8 happened and they were like Ashley figure out F8 and I was got it and so there was just so many pieces of that experience that were great. I think that some of the harder things were so many people were trying to give advice and feedback and we didn’t have a singular person that was kind of the person that was helping us understand how we fit in. I think when you put a bunch of big personalities from a startup into a big company,…

Ashley Smith: there’s going to be some friction.

Ashley Smith: And I do think that, at the end of the day, no offense to the South Bay or Peninsula or whatever you call that place, but we were all living in San Francisco and it was a very big shift for a lot of us to be in San Francisco walking to our dinky little office that had just been upgraded to this nicer office.

Scott Smith: That new office was so sick. Yeah. Yeah.

Ashley Smith: And then a week later, they were like, “Just kidding. We’re dismantling it and you’re going to go live in Menllo Park. Is that what it’s called?” Yeah.

Scott Smith: Yeah. Right.

Ashley Smith: Facebook campus is beautiful.

Ashley Smith: I’m not complaining about that. very fortunate to have that, but it was a shock to the system for me financially. It was my very first time ever having money and not even a lot of it, but just enough to eat. So that was cool, And so I’m so thankful for that time. It paid off my student loans.

Ashley Smith: I got to pay off my credit card debt. all those things. it was a little tricky in some ways. You remember all of it. It wasn’t that could have done a better job of handling it,…

Scott Smith: Yeah.

Scott Smith: Yeah. I in fact Yeah.

Ashley Smith: I think. Yeah.

Scott Smith: And I think that’s part of growing up and learning how to go through good experiences that are challenging. Okay. So, one of the other things that I’m particularly interested in and having now your own investment fund. obviously that is pretty cool because you get to lend into lots of different companies and you think about all the developer experiences you’re now seeing this wave and…

Scott Smith: shift of AI and I imagine AI it’s this obsession that runs through everything, every conversation. What’s that What are you seeing?

Ashley Smith: conversation. …

Ashley Smith: it’s good and bad. The good thing is a lot of people are just trying to build AI for something, And that may not be the best approach, but from everyone trying to build something AI related, there’s a lot of gems coming out of that that are actually pretty interesting. I don’t know if we need more AI for lawyers things like I’ve just heard I’ve been that and that’s not what I invest in. So, I’m sure it’s very useful and important, but we’re seeing a lot of that.

Ashley Smith: I think where I get excited and what I’m seeing every single day a lot of is AI infrastructure pieces. So somehow enabling security to help you build the law more securely. that to me is more interesting. I just saw a CD thing that is automated AI CI/CD so that you’re not having to do manual testing. So very specific use cases that empower developers to do their work more effectively and…

Scott Smith: Yeah. What’s your feeling on the replace versus enhance?

Ashley Smith: not like I’m building a robot that replaces all computers that’s not really I think where we’re at yet. but yeah I think it’s an enhance I think some stuff needs to be replaced not humans but some tasks I’m like why am I doing this manually?

Ashley Smith: but I think it’s an enhance and not a replace. But I think that it’s going to compensate. I could be totally wrong. but I think because so much more information and tools and knowledge and everything is coming at us as a human, we need to be more efficient so that we can manage everything that’s happening. And I think that AI will help us do that. I think about 20 years ago, is that 20 years ago.  And when you think work, I was an IT intern somewhere and they were still sending out physical memos and you had to know how to address the memo and you would send it out through paper and that was such a slower process than sending out 50 emails in 10 seconds. and so I think that we need to be more efficient. We’re all over we have too much coming at us. I think it’ll make us more efficient. I think the same is true for development.

00:25:00

Ashley Smith: I think developers are getting more and more complexity in their tool stack. I think there’s more and more complexity across everything you’re building.

Ashley Smith: There needs to be more eyes and even if that’s automated eyes on what’s being built. I think those are pretty interesting use cases.

Scott Smith: It’s pretty interesting.

Scott Smith: And are there any particular technologies where you’re of all the things that you’re kind of most excited about some trend or…

Scott Smith: specific AI thing or specific or developer area?

Ashley Smith: Yeah, I like the quote unquote boring stuff.

Ashley Smith: It’s not boring at all, but I don’t get excited about the stuff that’s very like buzzy and everyone’s trying to do it. I like this is going to sound so bad. I like compliance and sec. I’m obsessed with security right now.

Ashley Smith: I think that because we have so much more complexity hitting that the security issues that we’re going to see are just pretty much higher. And so I’m very excited about the security stuff I’m seeing. I think the way that we like store and trade data amongst different products or different tools is kind of weird and I think that’s going to get better. so yeah, I just like not the less trendier side of all of it, but it really is just like anything in AI infrastructure is where I get excited. Yeah. Yeah.

Scott Smith: you’re not going to have budget to pay for it, too. I think that’s a big part of it that I think about.

Ashley Smith: I want and I love what I do. I love working on de development products and working with founders,…

Ashley Smith: but at the end of the day, I have to make money because if I don’t make money, then I don’t have a fund.

Ashley Smith: And so I understand the parts that actually monetize and the parts that make sense in the context of building products as a developer and boring unfortunately or fortunately does monetize.

Scott Smith: Which is an important part of building a business.

Scott Smith: It’s nice to build cool stuff.

Ashley Smith: It is Yeah it is. Yeah. …

Scott Smith: So you have this distinction at least that you mentioned early on with respect to Vermillion Cliffs and also just kind of general investing. You talked about, technical founders. Talk to me a little bit about that.  What does that typically mean for you? Why is that important?

Ashley Smith: there’s an interesting kind of person and Ilia from PARs is one of them. Kevin, James, all of those founders. You need to find a technical founder that can also talk to customers. You probably know this deeply.

Ashley Smith: a founder’s job for the first few years, if you’re doing it right, is going to be spent a lot of time on the phone or on video chat or in person with customers, about thinking about go to market. But I prefer to work with technical founders that can go to market side if given a little bit of coaching, but that they’re naturally a bit extroverted or at least can pretend to be a little bit extroverted.  I think not all of my founders are deeply technical, but all of them have worked on products that are technical. So I consider you to be technical, and in your mind you’re like, ” I worked in sales on technical products. To me, that makes you technical.” and so that’s how I kind of distinguish it.

Ashley Smith: But really the main key thing I’m looking for are founders that know how to talk to customers and get excited about talking to customers because they know that customers are just users and that will be excited to use their product and give them feedback and all those things. So I think we’re calling it founderled sales now, but it should just be is a part of the founders’s job in my opinion.

Scott Smith: Yeah, it’s funny how you have to describe the action that you’re supposed to be doing in a way that makes it more clear you should do it. It’s like you should build a product.

Ashley Smith: Yeah. Yeah. Yeah, exactly.

Scott Smith: So, it’s a founder building technology or something. It’s kind of weird.

Ashley Smith: We put these taglines and things, but it’s founderled sales. it’s just like the job.

Ashley Smith: It’s like…

Scott Smith: 

Scott Smith: Yeah. Yeah.

Ashley Smith: what they Incredible. Yes.

Scott Smith: Absolutely. I think the way you’re thinking about is awesome as I’ve worked with so many technical founders who are friends and there’s usually two scenarios.  One is they are so reluctant and just hate talking to customers or potential customers and you’re kind of like that’s oxygen to your business and you either got to figure it out or you need to be lucky enough to hire sales people but that assumes you have some revenue or there’s the person who’s a good example I think it parses Matt one of our early software engineers. Yeah.

Scott Smith: and he builds this pharmacy delivery product and they spend him and Jamie spend most of their time presumably coding and then also doing pharmacy stuff. But if they couldn’t keep up with the demands on the technical side, the product probably wouldn’t have worked. And I think it’s a great example where Matt’s he’s a jitsu testosterone customerf facing kind of guy…

00:30:00

Scott Smith: but early on he was almost afraid to do it. So he completely changed and he still has that technical skill set and that customer skill set right.

Ashley Smith: and he was great when we put him on stage for talks.

Ashley Smith: He was incredible. So, he really came, I have a soft spot for everyone at Paris. he’s an incredible example of someone who really figured out how to be customerf facing, got on stage, gave talks, stood in the booth, would talk for hours, and just got better and better and better at it.

Ashley Smith: down. Yeah.

Scott Smith: 

Scott Smith: Yeah, absolutely. I have kind of two other sort of follow-up questions maybe two final questions for you. One is I think particularly on competition. So you mentioned there’s sort of the boring companies that are building cool stuff customers things that our customers want Paul Paul Graham style like build something people want. and obviously there’s a lot of competition.  So when you think about the advice that you give to founders with respect to competition what’s your view on it how do you think about is it always aware you’re just kind of focused on your own thing how do you make sure that your product is excellent for your customer you’re aware of your competition how do you make sure it doesn’t consume

Ashley Smith: want to have multiple people kind of playing in the same market because it’s validating and it helps do brand awareness for all of the companies trying to do a similar thing. You can’t obsessively watch what they’re launching and copy it because then you look like you’re just, a copycat. You want to build things that are unique to what you’re creating.  Ultimately, it comes down to great product, great marketing, which some founders, I think, fall into the trap of if we built the best product ever, we’ll win. And we’ve seen that time and time again. That is not what happens. You have to have great customer support, great marketing, great sales. You have to really build a full package of a company.

Ashley Smith: And then on top of all of that, you need to be shipping at a pace that is outshipping most of your rivals. And I think that’s why it’s so interesting when I see people like the competing with a Google or an Amazon, great giant companies, And they ship a little bit of everything. And you’re always going to be kind of competitive with them if you’re building in technical products, but they ship very slowly. They’re not moving as quickly as a startup can do.  And so I think that the speed at which you can ship at a startup is how you primarily win the earlier market and then just building a great team that can do all those other pieces. You’re always going to have comp ideally you have competitors. and it’s okay. It’s not something you should obsess over. Yep.

Scott Smith: Right. Yeah. I think the speed aspect of things just looking back at all the best companies that I’ve worked at in whatever department that I was working with, engineering, sales, marketing was always…

Scott Smith: how fast can you ship and keep high quality.

Ashley Smith: Yep. Yeah,…

Scott Smith: If it was slow, that team just got ground to dust for

Ashley Smith: it just is what happens. and I think something else interesting is a lot of especi in my market which is all developers, we’re curious beings, right? We want to use the new cool fun thing. And in some ways, being the startup doing something that maybe Google or Amazon are trying to do or are starting to do is a good thing because we’d all kind of prefer to try the new fun thing versus just turning on a different setting or a different product from a company that’s bigger and a bit scarier.

Ashley Smith: So yeah.

Scott Smith: It’s funny.

Scott Smith: I don’t know what the right word or title for it is, but it’s like I’m in this monogous relationship with Google Docs, but if there’s a new product, I’m going to go out and…

Ashley Smith: Yeah. Yeah.

Scott Smith: try it right away. Google’s like,…

Ashley Smith: I think…

Scott Smith: “What’s up, dude?” Yeah.

Ashley Smith: but then we’ll always use Google Docs too, but there’s going to be other stuff and then some of it sticks and we pay for it and that’s great. And sometimes we’re like this is terrible. I’m never going to use it again. So Yeah,…

Scott Smith: Last question for you and this is kind of coming back to the beginning.  So, Vermillion Cliffs is the new main focus for Talk to me a little bit about what you’re excited about over the next 6, 12, 18 months with them. And also, just tell me a little bit about what it’s like to start this kind of new business. and I know you’re unmanageable, but you’re still in charge. So, what’s that like?

Ashley Smith: I am unmanageable. it is so much fun.

Ashley Smith: It is constant anxiety because you know that if you fail or if anything goes wrong or it’s all your fault and that’s just part of it. I think that’s part of being a founder and part of being in my case a solo GP. but it is really I’ve loved my whole career. everything I’ve done nothing’s been perfect but I’m very appreciative and love all of it.  This has been by far the most rewarding and interesting thing I’ve done because I had to learn how do you build a fund? Okay, what does the back office look like? How do you raise money from these giant institutional investors? What does it mean to build your network in a way that you’re getting fuel flow? there’s so many pieces and layers to my job. I’ve heard so many times ” VC’s life’s so easy. You just kind of talk to founders and write checks.” And I was like, “I wish.”

00:35:00

Ashley Smith: frankly that is about 20% of my day. there’s so much in fund management and fundraising and just the back office side of having a fund that people don’t realize. And especially if you’re a solo GP and quote unquote emerging manager. it’s a lot of learning which is fun and a lot of work just to keep the wheels on. I think I love talking I get energy from watching founders get excited about what they’re building. And I think that if you get to meet with a few of those a day who are so excited to work on what they’re building, it kind of transfers and you’re like, ” yeah, that is cool. I love that.” And I think that I really love. operating versus investing is interesting. Operating, you’re obviously in one thing and you’re so deep into that one thing, you don’t see outside that bubble.

Ashley Smith: investing is interesting because you get a view of everything and I love it. I like helping the founders figure out things like you and I have seen some things over and over and over again can give advice that we have a history kind of informing and just when one of my founders I have a Slack channel full of all of them and we chat really yeah it’s so much fun. and one will ask me a question that I’m like, ” yeah. You just do this. Here’s a link. Do that.” And I feel like, ” I helped somebody. This is great.” So, it’s really rewarding work. I’m thankful to my big investors that have helped me get started and yeah, I love the job. It’s great. I’ll be doing it until, I can’t do it anymore. So, I think this is a long-term career path for me.

Scott Smith: Love this idea of Ashley Smith this grandmotherly helper in this Slack channel hey does anybody need help with their I think it’s great no I guess grandmother’s right it’s more like the aunt right I don’t  Awesome.

Ashley Smith: Yeah, it’s totally it.

Ashley Smith: I’m like, does anyone need help launching? that’s my current thing. Call me You can call me grandmother. It’s fine. but yeah, no, it’s really nice. it’s an interesting thing to take all of my experience and all my experience working with so many great people and kind of apply it in a different way. changing careers is I guess I didn’t think I’d be changing careers after having such a big operating journey. but it really does as a transition make so much sense.

Scott Smith: Hey, thanks for spending some time answering some great questions. the questions were okay, but your answers were great.

Scott Smith: Ashley, thanks so much and I’ll see you again soon.

Ashley Smith: Yep. Thank you,…

Ashley Smith: Scott. Bye.