Patrick Driscoll: Welcome everyone, and thanks for tuning in to “The Innovation Imperative.” My name is Patrick Driscoll, and I’m the director of client development for emerging companies and venture capital at Holland & Knight. At Holland & Knight, we work closely with founders, venture capital firms and investors navigating the full life cycle of innovation, from company formation and early fundraising through growth, scaling and ultimately that exit. A big part of our work sits at the intersection of law, capital and strategy, helping innovators and investors think clearly about how they build, fund and protect durable businesses. “The Innovation Imperative” is really about that journey. Each episode we sit down with founders, investors and operators who are shaping the innovation economy, often behind the scenes, to unpack the real stories, lessons learned and inflection points that don’t always show up in a pitch deck or press release. We focus on VC, early-stage companies and the decisions that matter most when the stakes are high.
I’m pretty excited about today’s conversation, as I’ve followed this fund for a long time. It brings together two great perspectives. I’m joined by my colleague, Tim Poydenis, a partner at Holland & Knight and the head of our EC/VC practice group who advises funds in emerging companies across formation, financing and strategic transactions. And we’re thrilled to welcome Paige Craig, general partner at Outlander VC, an early-stage firm known for its founder-first approach and systematic sourcing model. Paige has invested across categories with a sharp lens on what makes a team and market truly fundable. And with that, I’ll hand it off to Tim to take away the conversation.
Tim Poydenis: Thanks, Patrick. Really excited to be here and pumped to have Paige as guest number one in this podcast series for us. So, Paige, welcome, we love working with you and we’ve thought highly of you and your fund for a while. So I think it’d be helpful for everyone out there listening to hear your story and your path and how it shaped what you’re doing over at Outlander.
Paige Craig: Yeah, thank you. I think it is only relevant in the sense that my very unconventional, weird path reflects the kind of people we like to invest in. So I grew up dirt poor. In fact, we were homeless. We lived in cars, lived in a river in Sacramento. I had a pretty good family life, but you know, we were just very poor folks from Pennsylvania. And I had a very early life of struggle. I eventually went into the Marine Corps, the intelligence community, built a wildly successful private military, across the battlefields of Iraq, Afghanistan, Syria, sold that company in ’09 and built my venture fund back then. And that weird journey really led me to realize two things. One, I tried to raise money for my startup. I was a weirdo, I was very different. I thought that because I was first in my class at Dam Neck, Virginia, that [because] I was extremely good at my job, people would throw money at me when I left to go start my defense startup back in 2002. Defense was not cool then like it is now.
Tim Poydenis: Yeah.
Paige Craig: And I also learned along the way – I had no idea what VC was, I never thought I’d be a VC – but when I did get into venture, I realized that most of VC looks at tech or market or momentum and it doesn’t actually look at people. And the unusual thing about my background is, in the intel world, I spent a lot of time understanding, analyzing or recruiting people overseas for a lot of the intel and other work that we did. And so my lens was really framed by an unconventional journey as an operator and founder and by this lens that people are the most important thing. And so that’s what really framed me when I came into the startup world back in ’09 and decided that I was going to go be an investor with zero experience, zero background, funding, investing, like I knew nothing about it.
Tim Poydenis: Wow, well, first off, thank you for your service. That’s a phenomenal story and background that you gave us. So when did you start Outlander? When did your fund come to life?
Paige Craig: So Outlander is a rebrand of our fund that I started in 2014, but I started investing in ’09 as an angel. So I spent five years and did roughly 70 deals, just out of my own capital. And then I’ve been a VC from the end of 2014 to the present day.
Tim Poydenis: Wow. And a lot of your thesis, if you look at a lot of your guys’ social media and your website and conversations, I know you and I have had, you talk a lot about being founder first. Can you give a little bit of color on what that actually means? Because I think a lot of folks out there say that, but I don’t think everyone truly follows it. So it’d be helpful to get some commentary.
Paige Craig: 100 percent. All humans are somewhat social animals, some of us are more social than others. Every VC probably tells you they invest in great people, and that’s true, we all want to invest in great people. What we mean when we say we are founder first, it means two things.
One, which is quite common, I think, in venture, is that we really understand that we see startups from the end of a straw, right? And so we don’t get to see the big picture that founders see. And so we really respect being mostly former operators here at Outlander, we really try to make decisions and work with founders in a way that we would have wanted when we were operators. Doesn’t mean that we don’t have hard discussions, but we really try to remember that we are here to back up these crazy big visionary founders who are struggling daily. So we try to avoid second guessing them, but we try to make sure we have hard conversations with them. So we try be a great friend to founders, and that means also not pulling punches. There’s a lot of people out there that I think are cheerleaders to founders versus being good coaches and mentors. So first we want to be aligned with our founders helping them build big companies.
Second, we look deeply into the nature of the founder or the founding team. And what that means is beyond just thinking like a vibe investment: Do we like this person? We dig into your life from middle school, even elementary school onward. And we have a founder framework. It used to be 38 points, I condensed it down to 20 in the last year, but it started life as a 14-point framework a decade ago. We have evolved it, but it’s a very formal framework for all of our partners to dig in and analyze the founding journey. And it focuses on vision, intelligence, character and execution. And it’s a selection process where we have long conversations with founders. We really don’t care that much about reference calls. We really look at life and talk to you about your life. I teach my partners a couple dozen elicitation tactics, essentially ways to talk to people and try to get the truth. And not that these are people trying to lie to us mostly, or they’re not foreign adversaries trying to deceive us, but the reality is everyone lies and deceives themselves to a bit. And so we really try to get to the uncomfortable truth about who you really are, what drives you, why do you do this? So that’s really important to us, spending a lot of time digging into the founding journey. And like, we don’t want to see decks. We tell people to send us a deck just so we understand where you kind of plug in for future combos, but we really dig deep into your story: your love, your hates, your disappointments, the wrecks, the abysmal low points of your life. We want to dig into everything that was crap and understand what happened, how you dealt with it. So that’s us. So we really get in the weeds of who a founder is and what drives them to be great.
Tim Poydenis: Two questions there. The first one: Do you dig into the attorneys that you decide to work with at that level?
Paige Craig: No, and I’ve had VCs and LPs, especially LPs, always want to know, oh, let me tell you my story. And it’s like, you can build a framework – because we did this in the military – we built these frameworks to understand certain types of targets. And so in this case, this is specifically built for founders, early-stage founders in high-growth technology startups. This framework does not define a good buddy, a coach, a father figure, it’s designed based on now over 10 years of work and thousands of interviews to find founders that have a better chance than the average population to succeed.
Tim Poydenis: Sure, on that point, obviously founders know that funds and potential investors are vetting them individually in the business. Do your founders at the outset know that you’re running that level of process on them behind closed doors? Or do you just sort of tell them you’re going through your typical checks and diligence? Or do they understand what the process entails?
Paige Craig: I think anyone that reads anything about us should know. We do tell them what we care about. We don’t tell them each detail because we do not want people to game us, but we do tell them that we really care about them. So most founders, even the thousands we reject – we take about 5,000 partner meetings a year – we tell founders, we are really digging into you. We’re trying to find not only great founders, but founders that are going to work well with us. There has to be a match between us and the founder as well. There’re people out there who sometimes think there’s something special about them, but it’s not a fit for us as a partnership.
Tim Poydenis: Yeah, let’s just look at the start of 2026, like if you had a checklist of things that need to be true for you guys to lean in on a deal and ultimately make an investment, what are those high-level punch list items?
Paige Craig: It’s three things. So the founder framework side, we need to be 90-plus percent certain that you just knock it out of the park for our founder framework. Second, you need to be in a sector that we think is going to have extraordinary outcomes in the next decade where we have an unfair advantage to help you win. And third, the deal needs to be right. And this is often where our lawyers help us out. Everything from the pricing, the terms, the board, board observer, all those little details that we go through on those term sheets in the week.
Tim Poydenis: Sure.
Paige Craig: All three, and this is something I learned as an angel and early VC: It can’t just be a great founder, and it can’t just be a great founder in a sector that I love, it’s got to be a great founder in a great sector with a deal, with terms that let me make a massive return if you win and let me invest along the way and all this, you know, all the other stuff that you guys do as lawyers to help us get that edge on the deal.
Tim Poydenis: No, for sure. And that’s an interesting one. I mean, I’ve been fortunate enough and our team’s been fortunate to work alongside you guys on a number of deals. And I can tell folks listening that I’ve had a front row seat to where you guys have put terms out there, we thought we had a deal and then terms tried to get renegotiated at the finish line and Paige swoops in for a phone call saying, hey, I’m going to talk to Founder X and this is the deal, take it or leave it, otherwise we’re walking. As much as I’m sure you guys don’t like walking away from deals, there have been situations where I’ve seen you walk. So I do think that it shows a lot of focus to the guidelines that you guys have and commitment to your deals. And I know that there’s investors out there that sometimes, for lack of a better word, can cave. But that’s interesting to hear on your guys’ approach. You talked a little bit there about the industries over the next decade or so that you think are going to be there for success. In terms of like the industry focus and pockets within the industry that you think are high right now, what would be a focus area for you guys in the market?
Paige Craig: There’s a handful. I mean, this is the fun part. Beyond picking the right people, we’ve done, I think, exceptionally well predicting the future of the world. And that’s something I had to do back to my North Korea, Iraq – like, one of the fun things about intel is one of my jobs was to digest the world, literally the world, and talk to generals and admirals about where the world was going in the next 10, 20 years. And so that’s the other really fun part of our job, kind of predicting where that puck is going. So where do we think the world’s going right now? America and the world are at an amazing inflection point. Obviously applied AI, we started off doing infrastructure AI a decade ago, before it was cool. We’ve been very focused on applied AI for the last five years. But we’ve also set our sights on robotics, hardware and autonomy, which is still not as popular, but we started doing that years ago. And the recognition was that software is becoming a commodity. It is clearly going to be a commodity when anyone can build software. That’s where we’re going. And so you need another edge if you’re going to create value. We think hardware and robotics are two places where investors can find value, where founders can create value. So AI and software embedded in a robot that does agriculture, does construction, does healthcare, does anything – we’re at this amazing point where software plus hardware can build that future world. And also related to that is the re-industrialization of America. We are investing in 3D printing battery companies, companies that build software to design propellers and homes. We have a 3D printing munitions business that’s 3D printing weapons and warheads for the next generation systems out there. So we really think that robotics, industry, autonomy and deep tech are our big categories for the next 10 years. And we really invest in people, so we’re open to any idea, but those are four lanes that get a lot of our attention these days.
Tim Poydenis: Yeah. It’s truly remarkable to hear and how you compare it to the time you spent in North Korea and Iraq. It’s a perspective that I can imagine founders are in a room with you, and there’s a reason why so many companies want you on their board and want you guys on their cap table, given that perspective and just viewpoint on the direction, not only just where the venture landscape is going, but more just where the world’s going. In terms of industry and your investments that you’ve made, I obviously have an idea or two on what I think some of your favorite investments have been over the course of your investing, but I think one that’s obviously very interesting to me and most people that are probably listening was the investment you all made in Scale. Can you give a little bit of background on how that investment came to be? And I know that you guys, I think, I mean, you tell us, were the first check in, right?
Paige Craig: Yeah, we were the first and only check in their very first round pre-Y Combinator. The founders had come to us – and not that we were the first or only – like every founder out there, they had pitched dozens and dozens of people, and we were someone that they hit up. And so the story goes that they were in an Uber, the Uber driver knew about us and said, hey, you should go pitch Paige. They reached out on Twitter, I said hey, follow me back. Within days, we were doing a hike in the San Monica Mountains and a few weeks later, we were the first and only money in that first round. They went to Y Combinator, did OK, it wasn’t amazing business, but we introduced them to like literally 90-plus different VCs. Accel, amazing fund, Dan Levine led that round, he was instrumental in their business. But yeah, that was the early days. And the funny thing is when we invested, it had nothing to do with their product. At the time, the company was called Avra. They had a couple different AI ideas: One was dating, one was medical, but neither one was actually core to the founders. And I really think I did probably only two things that really mattered in the life of that business. One was investing in them and saying, I don’t care about either one of these products, I think you guys are amazing. And second, when they came back a couple months later and said, hey, we think this data labeling thing is big, we want to do this API, where any AI company can call up our API and just get data labeled. And I read through it and I called them back and I responded, saying, this is a big idea, this is worth dropping everything else and just focusing on that.
Tim Poydenis: Wow, that’s wild. From a Twitter message to an Uber ride to hiking in the Santa Monica Mountains, that’s a pretty wild backstory. And something you said there was very interesting for me, because I know a lot of founders that we work with ask this question. You mentioned after that initial investment, you made introductions and reached out to I think hundreds of other venture funds for them. Is that something that you do with all of your portfolio companies, like when the time is right, do you try and play matchmaker and facilitator for them?
Paige Craig: We do. So I’ve been a big believer back to my intel days that you want to build a massive network and then you want to leverage it for your founders as they prove themselves. So in early days of Scale, we saw that they’re very impressive. So we started to do more and more investor intros. Customers are another thing we focus on in early days. But we help founders build out their early networks. It’s one of the things that you could do as a VC, is to really open up these networks to founders who might be on their first company. The founders of Scale were 18 and 19 years old when we funded them and didn’t have much of a network. We just funded a group, amazing guys, actually a guy whose family escaped Iraq and he was a little boy when I was running around Iraq.
Tim Poydenis: Oh my God.
Paige Craig: And this amazing dude Hadi from Lebanon, and they came to Canada, they went to school up there. Hassan, the CEO, went to University of Waterloo, and we just funded his AI lab. They’re building this amazing technology to help AI navigate the web and make it useful, which it can’t actually do right now. And I just spent the last week making introductions to founders, angels, investors and helping them just meet really brilliant founders and other folks that are like a step ahead of them. And we do that for almost everyone we invest in, whether it’s investments across the Pentagon or investments in industry, it is one of the biggest things that an investor can do.
Tim Poydenis: That’s awesome. I think that if you talk to any of my entrepreneur clients on the company side, I think they’ll all recognize this phrase that I say to them when they’re talking about term sheets and everyone’s bogged down on what’s the valuation, how much cash are we getting and all this. And the phrase that I always come back to is, “not all money is created equal.” Like you truly need to be evaluating the funds that’s investing into you because it’s going to be a partnership for, potentially, the whole life cycle of the company. So I think hearing your guys’ approach to working with your portfolio companies and founders is something that’s pretty remarkable. And we’ve seen it firsthand on the success your companies have had with your guys’ touch points all over them. I want to go back a little bit to something that you mentioned a handful of minutes ago when you were talking about your team at Outlander. You made a comment about how you guys are all former operators. Is that a requirement for your team as you’re growing, that you only want former founders, former entrepreneurs as part of the investment team?
Paige Craig: I’d say mostly. We’ve made some exceptions, but on the partner, senior partner, managing partner level, yes, to come here at any of those levels. And we are looking, so if you’re out there, we want operators, founders who’ve had success, who are now ready to be coaches and mentors to the next generation of founders. I think that experience and that perspective is critical to the stage and strategy that we have of being very hands-on and being very early. And the other part that we didn’t really nail as part of our strategy is we are not looking for hot deals. We want to reject those deals, not because they’re not good, but the founder who can get Andreessen’s attention on day one, YC’s attention on day one – you could be a great person, but we are really looking for those oddball, unknown, under networked, underrepresented, we’re looking for those black swan opportunities. And so we want the founder who really wants our assistance. We like working with those founders that are not known quantities right now.
Tim Poydenis: And why is that? Is that because you think you’ll get better deal terms, or is it because you think that with your guys’ relationship and the infrastructure you build up for your founders and your portfolio companies, that you’ll help push them in the right direction?
Paige Craig: For me, it’s three things. One, it really just speaks to where I came from, and I really like working with people where success is not guaranteed, it has to be earned.
Tim Poydenis: Sure.
Paige Craig: I really love working with founders who come at it with determinism and a work ethic that is undefeatable. Second, as an investor theme of strategy, I would rather have this night vision to pick the right person and help them win when that deal and that opportunity is unproven. We get a better price. And third, we have a real impact on the world. There’s a lot of great companies and founders I meet and they’re raising, not just high terms, because usually an inflated evaluation as we think about it, or just a high valuation, is simply a reflection about how the market perceives the risk or quality of this team. And so someone coming out of their third great startup with two unicorns under their belt. The price is high, but it’s high because most of the market is saying, hey, we think this is a de-risk deal. I want to go find that first-time founder or that founder that had three massive failures under their belt but they’ve learned from it. I want that founder who is ready to win and the market doesn’t see it. And when they win, we know that we did something important in the world and we had an amazing 10-, 15-year journey with them. That is what we want. We want all three of those things to be true when we invest in that unknown founder.
Tim Poydenis: I don’t know how a founder doesn’t want to be on your guys’ portfolio. It’s pretty awesome to hear and to hear it explained like that. It speaks volumes, I think, about how you operate. You gave in your history and sort of your character and reputation that I know you’ve built in the industry. So it’s exciting for me just to hear you lay that out. In terms of the success that you guys have had, obviously, with a lot of your wins – not limited to the one that we spoke about – I know there’s been a lot of other successful investments. I think it’d be helpful for the funds folks out there to understand how have you been able to scale your fund and the size of your portfolio with building the right infrastructure, both internally and externally, with support and help. Because as much of a stud you are, I imagine that you only have so many hours in the day, so you need to build stuff up around you.
Paige Craig: We do. You know, venture is really limited, not by the dollars, but by the people that work here and the support that we have. So one thing is we haven’t scaled that fast. We have focused on results and driving returns versus getting too large. I think the last decade showed a lot of funds that got too big, too fast.
Tim Poydenis: Sure.
Paige Craig: And we know what our mission is. We know that our focus is to invest in the earliest stage unknown founders and to be hands-on with them, which means we can’t grow too fast. But the way I’ve scaled is every year we’re open to hiring a partner and maybe an operational support person. That’s kind of been our growth. On the fun side, we added an opportunity fund last year, which let us double down on our biggest wins, but we’ve been very careful to not expand our cash too much and we interview a ton of people to find the operators that join us. And then on top of that, we have, like most funds, we have a back office that helps us on the finances, the auditing, all the financial stuff that none of us as partners are great at, nor is it the best use of our time. We employ lawyers, you guys handle a lot of the diligence to not just do the deal, the term sheets in it, but to look over and have a second set of eyes to make sure that we’re checking and doing proper diligence for these deals. As much as we love founders and deals, it’s important to have that perspective, the second institution that’s not vested in the deal, to make sure that we don’t make a mistake. And we all know that we get deep on a deal and we want to make it happen, but you guys can come in there and say, hey, did you see this issue and this issue? And that’s also very helpful. So in areas like finance and legal, we’ve outsourced some of that work to make sure it’s done the right way.
Tim Poydenis: My last question is – I know we’re coming up on needing to wrap this up – what’s a day in the life of Paige look like on a regular workday with all the things you have on your plate?
Paige Craig: I have, probably, a different perspective than many. I try to keep about half my day completely free and that way I generally am working from around 6:30 in the morning – I have a 2-year-old and a 4-year old – so generally around 6:30 ’til midnight, 1 a.m., I’m living and working through all of those moments. And 24/7, weekends, holidays, doesn’t matter to me. I invest in founders, and I tell them you can hit me up any time you want. Like this weekend I talked to the AI Labs company, I talked to Havoc, one of our maritime and multimodal autonomy companies. I talked with a laser weapons business. I talked to Calvis, an AI company for security. And like, that was all over the weekend, that was on Sunday. I keep half my schedule open every day. And I like to do this thing, I walk and talk. I pick up the phone, and I dial friends, colleagues, new contacts and I just see if I can get ahold of people. I have my deliberate calendar of things that need to get done. If a founder texts me, half the time I’m available to call or text back quickly. I called a number of VCs today, and I just have conversations. And those conversations can be about things I’m looking to invest in, they can be about my startups that are raising money, they can be for talent that we’re helping our founders with. And so I keep half my calendar free to support my founders and to let me go out there and engage versus having the calendar tell me what to do.
Tim Poydenis: That’s awesome. I love that approach.
Paige Craig: And everyone that works for me knows that you might wake up to a 7 a.m. call or a 10 p.m. call. I would like to call all the partners and junior folks every week and just talk to them about what they’re working on, what they are struggling with, what they are interested in. That’s just how I work. It’s a little bit different, but that’s my process.
Tim Poydenis: I think that’s awesome. And I think it helps the team see it from the front lines, but then also it helps some of your younger partners grow and have that direct interaction with you that I’m sure that folks in other funds and honestly other companies just don’t get. So I love that approach that you have. Patrick, I’m going to turn it over to you here.
Patrick Driscoll: Yeah, and I think if you’re adding a ton of value, working at that rate makes so much sense, right? And thanks so much to both of you. This was a very interesting conversation. And I wanted to highlight my top three points and my takeaways from it. One is founder-first investing is a rigorous discipline, not really a slogan. So, I think, Paige, your background in intelligence really allows you to figure out the framework of how to get after those founders who are going to change the world, so that was super interesting to hear. The second one is great outcomes come from the right founder, in the right sector, with the right deal. I love this point because you always hear VCs talk about, we only look at the founder, we only look at the founder, we only look at the founder. And you’re being a little bit more truthful here. It has to be a sector fit and it has to be a good deal, and VCs, I don’t know if they talk about that as openly as they should. And the third is the frontier of innovation is kind of shifting towards the deep tech, autonomy, AI infrastructure, robotics and re-industrialization sectors. You mentioned your ability to digest the world, which, I love that term, allows you to kind of figure out where the momentum really is in this VC investment sector.
And with that, I did want to say thanks again to Tim and to Paige and to everyone who’s listening. If you want to learn more about Outlander VC and their founder-first approach, check them out. You could find them on their website, find Paige on LinkedIn, and for the guidance on forming funds, structuring deals and supporting early-stage companies, check out Holland & Knight. Our EC/VC team is quite fantastic and robust. Tim is the lead of the team, and you could find his information online. And with that, we’ll see you next time on “The Innovation Imperative.”
