The Journey of Ian Swanson Starting 3 Venture-Backed Successes (Ian Swanson / Protect AI)

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Ian Swanson:

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you know, on an early stage company, when you don't have a lot of credibility of starting companies over and over again, it's who else can vouch for you? Who else can say this is a good human, first and foremost. and then the second part is not only is a good human, it's like this person actually can carry through an idea from concept execution to driving real value for investors. ​

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Jason Yeh:

What makes someone a successful founder? Is it. How much money they're able to generate how well they're able to lead their companies. How well they treat their employees. Or maybe. How many investors they're able to land. Those all play a role. I'm sure. But the real answer is probably more nuanced and certainly harder [00:01:00] to pinpoint. When we look at any successful founder throughout history. It's natural to wonder how they got there. To wonder what made them different from the thousands of others that try to walk the same path. But failed.

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Today I get to talk to Ian Swanson, three times venture backed founder and current co-founder and CEO of protect AI. Ian has raised over $82 million in venture capital throughout his career with two successful exits. And today's interview.

I decided to run things a bit differently. I wanted to learn what shaped him into the successful founder that he is. And what mistakes he learned along the way with raising and scaling as companies. To do that instead of focusing on his most recent fundraise. We ended up touching on all three of his companies. Sharing the ups and downs and the in-betweens of running a venture backed company. But to start things off, we didn't just go back to his first company.

I wanted to see if there was anything in Ian's childhood that hinted at him becoming an entrepreneur.

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[00:02:00]

Ian Swanson: what I can say is growing up, um, I was a middle class family. Grew up in a small town outside of Los Angeles, two hours east of L. A. No Starbucks, no McDonald's in my town. Um, again, middle class. But my dad did own a small company. And what I remember fondly growing up, uh, was sitting around the dinner table.

We ate dinner every night together, you know, as a family. Um, and he would talk about his day, you know, and talk about his business. And, And, now when I look back on that, there was a lot of lessons that I probably just soaked up and just learned. And also. Kind of put that itch, if you will, of like, Hey, I think I might want to start a company one day.

Jason Yeh: Yeah, so you did have an entrepreneurial role model. There's another part of the, kind of like your personality growing up that I'd love to touch on. I'm guessing his business wasn't a venture backed business. [00:03:00] Is that

Ian Swanson: No, it wasn't. He started it with a, I think a 10, 000 loan from his dad. It was in the construction space, you know, kind of your, your typical mom and pop business that, you know, over time grew,

but, you know, we had it for over 30 years and, you know, there's a lot of lessons that you learn in starting a scrappy business that you are effectively funding yourself.

Jason Yeh: totally. So then the other side of things that like I'm curious about is what, what were you personality wise in terms of like, were you, Introverted, were you extroverted? What was your relationship with like asking people for help, asking for money? If, if you can look back that far,

Ian Swanson: I would say I was definitely an introvert. I mean, I can, I can turn it on right in a networking and in a social setting. Um, but I was always the one that I would be locked up in my room doing my work and getting it done and not really. You know, in the team environment, maybe as much as I should. Now, growing up and getting into sports and stuff, you know, captain of various teams, you know, at that point, I started taking a leadership [00:04:00] role, you know, maybe it's starting to assert myself a little bit more, you know, at university and at college. Um, but it was really trial by fire with my first company of really getting into my first kind of leadership role,

you know, managing and building teams.

Jason Yeh: Um, amazing. So people can start from introverted backgrounds and then really, really accelerate their careers. People don't have to feel like only one personality type is the type that will build these big companies that will raise millions and millions of dollars.

Ian Swanson: Well, quick, quick story though

there. I, I remember I was in a speech class at university and I had to give a speech. I think it was to like 15 people. I was so nervous. So I probably failed miserably in that speech. Fast forward. I remember earlier in my tech career, um, I was having to give a keynote speech into it in front of literally over a thousand of their employees.

It was being broadcasted all over the place. And I got the prompt for the speech [00:05:00] 30 minutes before I was supposed to give it. And it was, Hey, you got to give the speech on innovation. And I'm like, innovation? Like, that's such a broad topic. Like, originally I thought I was going to be on a panel, maybe a fireside chat, maybe I was going to talk about my startup. And so, it is funny, like, you might think if I reflect back in college being so nervous and sweating about this speech class, you can break through those barriers in a pretty big way that now, I have no problem speaking in front of big audiences. I was in front of Congress last month. Like, you're able to learn, you're able to grow as an individual.

Jason Yeh: It's a great segue, Ian, into actually how I wanted this conversation to go, which is, you just said, like, there are skills out there that you might not, that might not come naturally to you, but after repetition, after, um, you know, working through some of your problems and getting better, you can become great at this.

And you're one of the first founders that we've talked to that has had multiple exits, successful exits under their belt. [00:06:00] From venture backed companies. You're now, correct me if I'm wrong, but you're now on your third venture backed startup as, the co founder or the founder and CEO of Protect AI. And I, and where we usually take these conversations is to dive very specifically into the company that they're working on today, how they thought about raising capital, where these things came about, like what are With the first challenges they ran into.

But when you went to start Protect AI, you were the global head of AI and ML at, at Amazon. You were, I think, spending tons of time, with leadership and had already sold a couple companies. You had a huge network within venture capital, um, just because of all the stuff you had done before. So that conversation of, of like, how did you go out and raise that first round of capital is less exciting to me.

And I think. Maybe doesn't, expose as many lessons as I would hope. So maybe you and I can talk a little bit more about if we rewind back to your first company, [00:07:00] Symmetrix, and we, we do a little bit more of a comparison to think about like, what was it like going to raise money as a founder the first time out?

and Symmetrix and, and how different that is today so that people can understand. I think one of the things that people figure out is when you hear about a founder that is raising capital and it takes no time, a lot of people as they start going and reading those articles are like, Oh, like, could I do that?

Oh, it only took, it only took Ian, Two weeks to raise 15 million. A lot of times that's actually two weeks plus a 15 year career in order to get there. So maybe we can rewind back to the beginning days of Symmetrix. And do you remember what it was like thinking about, I'm going to start a company and one, and then two, whether or not you wanted to raise capital for that?

Can you think back that far?

Ian Swanson: Yeah, [00:08:00] absolutely. So I'll share a couple stories on that journey. Um, I was freshly out of college and I was in telecom and I was doing well. Um, I worked for a company called Nextel at the time that eventually Sprint. Sprint had acquired Nextel. And in my early 20s, Making what I thought was good money, um, but I was bored to be honest and I wasn't stimulated and I wanted to innovate.

I wanted to build and there was a magazine at the time that I would read that I was really excited about. It's called Business 2. 0 and it was the, the first kind of technology magazine that I would read about all these founders that are creating companies and innovating, you know, and building really cool stuff.

And on the cover was, uh, Chris and Tom who sold Myspace. And I remember reading that and I was like, I want to be those guys. I want to build, you know, the products that a lot of people use and they're great value. So I came up with my first business idea. I was like, I'm going to build the MySpace for businesses. I was like, businesses should have a place where [00:09:00] they network and stuff. Now, one could go, Ian, that's LinkedIn. I was like, yeah, this is a long time ago.

Now, mind you. In my early twenties, I never would have been able to execute on LinkedIn. So I'm not saying I missed out on my, my big win, but I do remember I went and I pitched somebody that idea and I pitched a family member and a family member who was at one of the biggest firms in the world. And so when you talk about like, I had a connection, I had a lead in, you know, for my first business idea. And I remember sitting down with him over lunch and I pitched him on this concept of a social network for businesses. And his response was like, no, this is silly. He's like, go

Jason Yeh: That'll never work.

Ian Swanson: He's like, go get your MBA. And I remember just feeling so dejected. And that was my first no of like a business. Now there's many, many more no's that came after that. And I remember going back to my, uh, my girlfriend at the time, who's my wife. And I was like, man, I was like, I got shut down, but I really want to do this. And so instead of going back and getting my [00:10:00] MBA. Um, I was on TechCrunch at the time and I saw there was a company in Santa Monica hiring called UserPoint. And I met with the CEO and I was very open. I was like, Hey, I want to start a company in the next year. But I want to learn from you. And I want to learn from the scrappy startup that had just exited to AOL. I was like, I'm going to use this as my one year MBA, if you will, of tech. And so I came up with an idea. Um, I met two other co founders. Um, we actually created it on a piece of paper in a Facebook developers garage meetup in like 2007 of like, here's a business we want to create together. And then we went out and we found our initial check of 200, 000. Um, from the CEO of that company that I was at, he was one of the first monies in and another friend that we had that was higher up in the tech space. That wasn't too hard to get the 200K, but getting the next million dollars, I probably had like 80 nos, you know, at that point. I mean, it was knocking on a lot of doors.

It was showing [00:11:00] conviction. Um, and at the time we were building, uh, technology that would do analytics and advertising targeting on socio demographic data,

nobody was doing it back in 2007,

Jason Yeh: So, that's, well, first of all, the fact that you were able to land 200k from the CEO that you worked for says a little bit about you. A little bit about you, I think, like, um, that's a good nod in your direction. But you did go through 80 no's to get the full round together, right? Like that, overall, that was still a painful process.

Now, that was your first company. You had done data science after that, raised quite a bit of money for that, sold that company, and then have raised quite a bit for Protect AI. You have tons of experience now in terms of how you think about building companies, raising capital, finding partners. When you look back on your early days of raising capital for Symmetrix, now, now this is kind of like you, as, you know, you and I are probably similar ages, gray hair, thinking about, um, [00:12:00] Ian in, in your early twenties, what were some of the biggest mistakes you saw Ian making then as you were starting a venture backed company that you know now on your third company, it was like, man, I, I would have advised me to do something very different, something that other people could learn from.

Ian Swanson: you know, it's, it's a really good question. Um, I'm going to give kind of a weird answer. And that was, as it relates to raising money, I don't really think there were that many mistakes we made in the first company. There was actually mistakes in the second company.

Jason Yeh: Whoa.

Ian Swanson: and in the first company. You know, something that I, that I learned that eventually we were able to close around is I remember going in and meeting with these investors that wrote a million dollar check into the company and they said, Hey, we heard about you from four other people prior to you stepping into this room. And what I, what I realized was all of those meetups and all the things that I spent time on, on building my network really helped give that kind of credibility when you don't have credibility on those [00:13:00] early days. And so such a value add, and I would have done more of that probably. Because when I said I met with 80 people, it probably wasn't 80, maybe it was like 40 or so.

Um, you know, the first 35, first 37 people I met with, they didn't, I didn't have that warm referral in. And that was so critical, you know, on an early stage company, when you don't have a lot of credibility of starting companies over and over again, it's who else can vouch for you? Who else can say this is a good human, first and foremost. Um, and then the second part is not only is a good human, it's like this person actually can carry through an idea from concept execution to driving real value for investors.

Jason Yeh: Right. And I think that's a, that's a great call out, right? Because after you were able to do that once, twice, now the third time around probably didn't have to spend as much time like going to meetups beforehand, but a similar, a similar outcome, you know, happens when you go raise for your third company.

People have [00:14:00] heard about you, people have seen what you've been able to do. So you have that credibility there. It's a great call out for the first time founders out there that are saying, Hey, I would like to build a company, a company that needs investment before we can actually get to revenues. If you are 23 years old, 25 years old, never done anything before, the best thing you can do is meet people, give them a good sense for who you are, have some positivity because you know, it sounds superficial, but it goes way further than people expect.

Um, so When you think about not making a lot of mistakes, quote unquote mistakes, in your first company fundraising, do you think that was dumb luck or did you have people holding your hand along the way?

Ian Swanson: Um, I had met some people through that journey. So our We had raised not a lot for that company. We raised a 200, 000 or maybe it was 250 K then somewhere around a million and then somewhere around 5 million. And then we had a, a line of credit for our accounts [00:15:00] receivable and accounts payable cause we had a big float on a monthly basis.

So we didn't raise a ton. Um, but when we raised that million dollar check, I met one of my mentors, uh, Richard Wolpert through that. And he has been an operator, you know, and been on the investment side, um,

whether it's angel investing or at larger firms. And so I did have somebody that I could, I could speak with, I could talk to.

And I think that's one of the most critical things, especially doing this your first time is you just don't know what you're not going to know. And you need to be able to sit down. People have done this and walk this path before you so that you don't make early mistakes. So I, so I would view that as one critical area of help.

The other one was like my lawyer. That sounds weird. I've worked with the same general counsel and same law firm since 2007, uh, gregheibel. org.

And so when you have people that you trust around you, you're able to work with them to understand like, Hey, how do I make sure I'm not going to make mistakes on the get go, you know, and solve for that and upfront versus trying to unwind it, you know,

Jason Yeh: [00:16:00] Yeah. So this is a great thing that I was hoping would come out somewhere along the way, which is showing that Ian on his own, talented for sure, but he had help, right? Like the best people have help along the way. Uh, Richard Wolpert, also someone that I've had the, had the pleasure of spending time with in the LA ecosystem.

Great guy. Um, can we double click a little bit more into that relationship? Because he had built companies, he had sold companies. That is a guy that has, um, a lot of experience that he could share. Not sure why he would share it with you versus somebody else. And so maybe you could talk a little bit about your experience, getting a really great mentor to want to spend time with you.

Because I think this is a piece of advice that, people hear thrown around, like get great advisors, you know, get great advisors, get great mentors, but similar to other startup and fundraising advice, it's given in a very soundbite y, uh, fashion where it's like, [00:17:00] That's a great idea. And then you're like, how, how do I do that?

So you could either say, do you have any tactical advice around how you do that? Or just maybe tell the story of how you met Richard and got him to want to like you, him to like you enough to want to spend more time with you and to help you.

Ian Swanson: Um, from a tactical advice perspective, honestly, I just, I think I just got lucky. You know, with some of the people that I met, especially early on, uh, in my career, I think if there's a common denominator or something foundational and some of those early relationships that I've had in technology, it was working again with good human beings. You know, people that, you know, aren't just surface level wanting to talk about, you know, the, the business metrics and the product, but trying to talk about the people behind those products. And the challenges that you're trying to solve and not being scared, scared away by some of those challenges. And you get that with some investors. So Richard, it was, you know, he was actually the first million [00:18:00] dollar in, he was part of a JV fund that Excel, uh, Venrock and, uh, William Morris put together. With another guy named Paul Brico. And that was one of those, like, Hey, I walked in the room. There was four referrals, warm intros into it. And so there was some level of, of trust. Um, but then once we worked together, you know, for the first six months, the first year, you know, having regular board meetings, we developed a relationship that I could just text them or call them. And so some of my best board members have been that level of a relationship where it's like, no, we can just pick up a call and just, you know, Pick up a phone.

We don't have to have a scheduled board meeting. A lot of people get really concerned about oversight. They get concerned that a board's going to dictate, what they're going to do. I've always seen it as a huge value add. And I look at them as mentors and people I want to learn from. And if you treat it, the relationship as such, it could be a wonderful two way street. Um, and that's where I've gotten some of my early mentors was from board members and some of my early [00:19:00] investors,

Jason Yeh: Yeah, I think it's such a great call out. Uh, people are, Often swept up in the headlines of like, the crazy things that happen at certain companies, where certain boards do certain bad things, and it's like the only thing they hear about, but um,

Ian Swanson: but that's, that's, that's few and far between. Like I, like if they're going to do something bad, it's generally that there's something bad at the company is my view.

Like, like people go early on in my companies. I give a board seat. On my seed rounds, sometimes a couple of board seats, you know, and there, and you know, maybe I don't even have controlling equity, like after my first round, cause I have business partners that I work with and they go, Oh my gosh, you're giving up too much or there's too much risk there.

It's like, hang on, if I'm doing my job well, they're going to keep me around. And Oh, by the way, if we find a better CEO than me, let's go hire that person because I'm a stakeholder in this company too, right?

So like all those things are super important.

Jason Yeh: that's really funny, I don't know if you noticed, but some fireworks went off in your screen, and I

Ian Swanson: Yeah. That was very awkward at that moment.

Jason Yeh: [00:20:00] Okay, so there's another, there's another side of what you said about mentorship and advice. Richard Wolpert, uh, Paul Brico, amazing guys who, who have a lot to give. The other side was a lawyer. And I'm not sure that everyone thinks about their attorney as a source for great support or great advice.

Um, How did you get so lucky or is there an approach that you came up with to figure out that, you know, that partnership? What would you tell people about, um, sort of the service providers that they bring on and how they, you would work with them or advise people to work with them?

I love the call-out Ian made around this lingering fear founders have of board members gaining too much power. I think his answer gives you all a look inside the mind of a successful founder. When we come back from the break, Ian shares a wise take on how he thinks of his relationships with his service providers.

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Jason Yeh: [00:21:00] [00:22:00] Yeh,

Ian Swanson: uh, medium sized business and one of his confidants and people that he would always talk about around the dinner table was his accountant, you know, meeting with them and sharing business advice and how to scale up the business. And so maybe it was ingrained in me that, Hey, your service providers aren't just there to provide you the very specific service that they're selling you, meaning billable hours on this, but it's maybe, Hey, you work across dozens and dozens of companies. You've seen the patterns like I should be asking you questions, you know, on things that we can do to be a better business, better company or better operator, you know, on that. So I think I went in with that mindset. I don't think everybody goes in with that. And I think I got lucky on the partner, you know, that I worked with, like it was pure happenstance of how we got connected. Um, but the way that we have treated that relationship is one where I could call him on a cell phone. I could text him in between [00:23:00] jobs. I've reached out to him. So he's not even working. For me or for the company, but you know, we've been able to bounce ideas off each other. So it's a real relationship and you get to know these people.

You can't just treat them as just your service providers.

Jason Yeh: Yeh, Yeh. Well, I think if you can, if you do treat them just as your service provider, you are kind of missing out on an opportunity to add more value to you and your company. And I'm glad you said it in different words than I usually use. I tend, uh, you know, I think lawyers and accountants might bristle at this, but I tend to think like the core service that they offer, it is fairly commoditized.

I mean, as long as you find someone that has the experience of working with startups, they are going to give similar legal advice. And so people under trying to decide how they make decisions, really what you should do is to see how much additional value they can provide. How good is the relationship?

How much do you enjoy, Bouncing ideas off of them, getting advice around what you do so I'm glad you called [00:24:00] that out as a big part of, you know, sort of your growth and your success over the years. Um, so you went on and raised multiple rounds of capital at Symmetrix. Got to a great exit. Um, but you just referenced something that, um, We'll see if you're comfortable talking about.

Um, you know, you're in your third company and we're talking about what were the things that you, what were the mistakes you made at your first company raising capital? You felt like you did a pretty good job, but after all that experience, something happened at data science where in your, you know, your own reflection, you're like, maybe not the best things.

I wonder if you wouldn't, um, be too uncomfortable talking a little bit about that.

Ian Swanson: Yeah, I'm absolutely transparent. Happy to share. I, I would say one other thing, um, and this will play into this story. Um, I've always started companies with a team. Um, I've always had two co founders. Um, it's never been me on my own. And I think that's really important, [00:25:00] uh, is especially when it's gonna be your first time raising capital, for example, for a technology company, you know, they're investing in you.

And I think it's, it really helps when you have a team, whether it's people that, you know, work on the product side, you know, dive deep on technology or on the business. It's always been beneficial for me, whether it was Matt and Joe with Symmetrix, Colin and John, you know, with data science or Badar and Dee in this company. Um, it's a team effort, you know, and it goes all the way down, you know, to everybody on the team. Now to fast forward to what you're saying, I, I, I, mentioned, Hey, on Symmetrix, I think fundraising, right? We got pretty right. Even though it was small rounds and all that, I think it was the right people, the right timing.

And we pushed through data science. The lesson learned was, Sometimes things are too good to be true. Um, and so we had raised a small seed of like a million dollars. We raised a very small, a round of like 5 million. We had cash in the bank. We weren't raising, [00:26:00] and we had a group that met with us in our office and they were looking at companies in the Los Angeles area to invest in, and they said, well, what about your company?

Cause I was talking about all these other companies, all my friends companies in the ecosystem. And I was like, Oh, we're not raising. And they're like, well, what do you do? I was like, Oh, we do DataScience but we're not raising. They go well, would you take 10 million? I was like That's weird. I didn't even ask for the money. And so I, I go out the room and I call one of my investors. I was like, these poeple just offer me 10 million. He's like, go back in and ask for 25. This is a joke. I went back in and I asked for 20 or no, I asked for 20 and they said, how about 25? And then I was like, Oh my gosh. I was like, so I went and called one of my investors.

like, they said yes to 20, but they asked if we would take 25. So we ended up doing the round. And it was. It was advantageous. Like the, the, the deal made sense in terms of how it was papered, but I think it was a little bit too much money too soon. We hadn't figured out some things, you know, that we needed to kind of go through the pains of figuring [00:27:00] out. And so having money, sometimes sitting in your account, you sometimes move a little bit too fast. And so we moved a little bit too fast on go to market. Um, and then the money, even though it was too good to be true, like it was almost like free money from an investor that maybe wasn't your typical investor. It came with some challenges. Like we were always having to educate them what a good investor and proper board member, you know, might be, you know, and they had to set up a local group that was actually a Middle East group that has set up a local team, which is great, but it was all this like added hurdles that was like, this is not typical. And so even though it was easy money, just going down a non typical path is not always a win.

Jason Yeh: So I knew some of the story because, um, you know, we're lightly associated at my old firm. And so I wonder this idea of overcapitalizing a company is something that founders will hear from venture capitalists in different forms. Sometimes it's because a VC firm is trying to convince you to take their money [00:28:00] over someone else's.

But, sometimes, there's some real nuggets of wisdom in there, and you talked a little bit about it, I wonder if we could spend more time on that, what, you said something like, with all this money, it kind of got spent too fast, are you saying that there wasn't, there isn't a way to take on a lot of capital and do so, um, Appropriately or is it just so hard to do once you have the capital and I wonder if you could like explain that to people who have never had 25 million dollars dropped in the bank accounts at the very beginning of a company.

Ian Swanson: So. Yes, you can raise a lot more money and be prudent, you know, on how you spend that money. So let me be super clear there. And we weren't, we weren't egregious, you know, by any means, but, but I would say there's a lot of, uh, reports have been coming out that when you raise less capital, it's a forcing function to be super scrappy, you know, on that side, you know, and, and to be time bound of like, Hey, you know, even though we have X amount of, you know, in the bank, like we, we have to make [00:29:00] sure we reach product success before we raise the next round.

And it, it just. compresses everything. And I think it forces something on a company that, you know, is, is natural. When you raise a lot of money, it releases some of that, some of that tension, that I think is good tension. Now, fast forward to this company. Um, I raised 13 and a half million in my first round.

We'll get maybe more details. Then I raised the 35 million. I'm still sitting on 35 million cash in my bank account.

Like we, we can easily hire more salespeople, more marketing people, stuff, but we're early in our business journey that we're still figuring out some of the nuances of the product and the fit and the customers.

And it's going great by the way, but we just want to be super diligent in how we're spending this. And then when we see that the sales motions, the sales plays are repeatable, we triple down on it and we go super fast.

Jason Yeh: That's, that's fascinating. So if you're thinking about Ian, when he gets this offer for data science of, you want 20, can you make it 25? What do you think [00:30:00] you would have done differently with hindsight as, you know, hindsight of 2020? Would you have done anything differently? Would you have taken different

Ian Swanson: I, I may have, I may have done the round. But I would have, I'm going to speak against what a typical founder might say. I would have done it at a lower valuation. Um, and when I, I've been in this space since 2007, I've I've met a lot of friends that have been CEOs of their company. And aside from not getting product market fit or wrong timing or whatever, sometimes raising too high of a valuation can also be a death nail. In a company, and you're definitely seeing it a lot in the last five years where companies can't get up to the value that their valuation was at. And so

they're stuck. They don't know what their exit plan is. And so we got fortunate, like we found a buyer for that company in Oracle, which was a great buyer, great company there.

I still have, I think over a hundred people from our former team are still there, you know, [00:31:00] six years later,

which is awesome, like shipping product. Um, but I, I would say I would have lowered the valuation a little bit, which would have been nice. And that would have gave us more optionality for future investments or even other liquidity events. Um, and we, we took that to heart at this company at Protect AI. We could have raised that a massive valuation, but we purposely did not.

Jason Yeh: Hmm. Okay. So this will get us to Act 3 of, of Ian Swanson and fundraising. And where I just want you to say a few words is, tell us, tell me a little bit about the advantages you've had coming in to decide that you wanted to start this next company and that you wanted to raise money for it. Um, you know, sort of blend it with where you were.

Why you decided to do this next thing and what it's felt like, you know, at least everything else is hard. Company building, I think is always hard, but for this one part of it, like, it feels like you probably have it on lock. Maybe you can tell us a little bit about, [00:32:00] um, how starting this company and raising has been for Protect AI.

Ian Swanson: Yeah. I mean, if, if I was raising for my first company in 2007 with not much of a network, not much of a background or track record, you know, that was, that was a tough process, right? You had

to really convince people fast forward. And now it's like, I had exited two companies. I've been a, you know, a vice president at American Express, a vice president at Oracle.

Yeah. I had just left Amazon where I was the worldwide leader of AI machine learning. So responsible for the revenue number across 17 products and a worldwide team working with a hundred thousand customers. And so the genesis for this business was a lot different and I was in a totally different spot. And so Protect AI, I'm probably terrible at branding, but it does as the name says, Protects AI. We're a security company for artificial intelligence. And so I saw the problems at scale for my previous roles that I had. And so when I was thinking about [00:33:00] starting this company, I was actually at an event. Um, and it's a event for enterprise software executives, like myself and like venture, you know, leaders of the top firms. And this particular event, it's kind of weird. You sit on like beanbags, there's a topic on the door, and you free for all talk about whatever you want. Yeah, there's a little bit of a moderator there, but you know, it's pretty casual, and it's off the cuff, and you talk about whatever you think's important. And we're sitting in the room of this particular, uh, event that says security. So anybody want to talk about cybersecurity is in there sitting on a beanbag. And I ask a question, what about security of artificial intelligence? And I get like, looks at me like I'm crazy. They go two things. Number one, software, software codes, code. Well, I know that's not true. The second one, they say, well, we, we buy it from all the big, you know, cloud incumbents and they have security figured out. Well, actually I know that's not a hundred percent true either. And so as I'm sitting on a bean bag, I get a text. [00:34:00] From a guy two beanbags over, Ed Sim, who's the Managing Director of Boldstart. And he's like, let's get out of this room and figure out how to start your new company. So I didn't have to go around pitching people, and by the way, I'd already had another check that was me flying over to this event. Somebody was like, Hey, we'd like to fund it before you even talk about it. I didn't have my team yet. I did not have a deck of slides. I did not have a business plan. I didn't even know what we were going to do other than security of AI. And actually at the pool at this event, my wife was here at this particular event is when I bought the domain. Um, and so I didn't have any of that stuff. So, so the difference of like having to go and pitch dozens and dozens of VCs, not having your network, not having credibility fast forward to this time. It was. It was truly what they call inception investing.

It was before I had a company, before I had a team, it was just an idea. And I think that's going to be the new wave of investing is not just angel investing, it's inception investing. And you're seeing it with Bold Start and some of the other leaders that are out [00:35:00] there.

Jason Yeh: So that's a really great painting of that picture and the thing that I want to follow up is something that we had mentioned very on in our conversation. I don't want anyone listening to that and being like, just seething at what you were able to do, right? It's like, Oh my God, he went to a conference and had his buddy, you know, like text him and say they want to give him millions of dollars.

It's like this guy that has all the advantages in the world. The thing that we, we really need to point out is like, you've met Ed Sims at Boldstart over a 15, 20 year

Ian Swanson: was, it was over 10 years.

And so like we, we actually pitched him and his firm, I think at my first company Symmetrix in 2007, they hadn't even set up their firm quite yet. It was, you know, Elliot in LA trying to figure out like what to

do, working with his partner, Ed. And so that relationship like matured over time to where I was even trying to buy one of their portfolio companies when I was the CEO of datascience.

com. [00:36:00] And so to go back to, for the listeners, um, yeah, this wasn't a, Hey, I showed up at an event and got lucky, right. And

I'm super privileged, you know, it was, you know, years and years of building out a network and investing in the people, right.

You know, and, and I think that's where like a lesson learned is these relationships take time to sometimes squeeze value out of them, but you can get a lot of value if you put the appropriate amount of time, um, you know, it's huge value add.

Jason Yeh: Yeah. And the other thing I was going to say is so, one part that we just described why you, why you were able to do that is when VCs make bets this early on, they're betting on the people. And they have to have. Conviction in a person's ability to execute. They have to feel comfort in their, in their, uh, and what they believe a working relationship is going to be like.

And so that happens over a 10 year period of building relationships, seeing you execute. The other thing VCs tend to want to know about is market validation, problem [00:37:00] validation, right? And when we think about investing, the words that I use are like, whether or not a founder has a unique insight. And the word that I've been seeing layered on top of that, I saw Andrew Chen reference it recently, is hard earned insights.

So like, I like combining those two things and, you know, for you to have ran, run AI at one of the biggest tech companies in the world, you know, you have some insights in there and you were, you were talking about people raising their hands and saying, well, you know, like we buy from the biggest tech vendors and they have security.

Figured out and it's like, well, You were a leader at Oracle for a number of years and you do have some kind of hard earned insights And so if we layer that on top of the relationships that you built over 10 years You should be getting money way sooner than other people that don't have that. And so I think One of my big takeaways from this conversation is people can look at what is [00:38:00] possible after grinding it out For 15 plus years.

And if you believe that you still want to go raise capital, you should expect a bit of a delta, right? Like, you're either going to be grinding over 15 years and have a quick fundraise process, or when you go out and raise, you gotta expect some sort of grind in order to show investors who don't know you that you're trustworthy, that you're worth backing.

To show them that you have hard earned insights into a market, into a problem. Um, And so it's cool to just be able to talk to you, um, quickly to touch base on three different stops along the way. Um, and now you're building something that I think sounds like it's going to be massive. So, uh, and this was really fun.

I really appreciate you finding time to, to just share some of these insights. Um, you know, I always try to end with some kind of conversation, piece, question that is a little bit more fun. In terms of Protect AI, you know, you're, you're building cybersecurity for a new generation of [00:39:00] technology that honestly has, like, I feel like the vast majority of the world just found out about a year ago.

Um, and there are a lot of funny stories of AI and what happens out there. have you, has your company had to do much in terms of Interacting with funny experiences that enterprises have with AI. Like what's any of the weirdest or craziest things you've seen AI do within companies that you've had to, um, sort of like

Ian Swanson: So I'll give, I'll give two stories, um, on the side. Uh, first is the definition of AI and kind of. What people think it is today versus what it has been for a while. And so we'll meet with a customer in a large financial services or big technology company, and they'll have their chief information security officer on the call. And he'll go, Ian, we're on this call for education purposes. We don't really have any AI deployed yet. You know, so we're, we're kind of new on the journey. Now here's the odd thing where it gets kind of funny. The head of AI is on the same call for that company and the head of AI [00:40:00] raises their hand and say, actually, we have 7, 000 machine learning models live.

And the CISA goes, well, that's not AI. Well, if we think about it, AI is the vehicle for digital transformation, but machine learning models, machine learning is the power trainer, the engine. And so we're still at this phase of trying to explain as there's massive tailwinds. With large language models and chat GPT and it's in all the shareholder notes, you know, right now, it's kind of funny to me that we're still having to educate these large organizations of how they are similar in many ways the same.

And oh, by the way, you've been doing this for decades,

but maybe you haven't been securing it the way you have. The second story that I would give is. I was in front of Congress, um, uh, this past December and it was on the security, state of security of AI. And I'm giving a testimonial in Congress and it's my first time in front of Congress.

And one of the questions I get asked is, well, what about, you know, AI security as it relates to my local flower shop? And I'm like, wait a minute here. [00:41:00] I was like, I was like, we, we have such bigger problems on like our critical infrastructure, as an example. Like, why don't we focus there? And so to back it up, you know, funny use cases of AI, you know, there's, there's a lot of different ones.

I think for me, it's, even though I've been in this space for close to 15 years, I still have to take a step back and go, a lot of people still don't understand what is artificial intelligence and how it is pervasive. It's being used all over the place. There are millions. of machine learning models live all around the world in our most dearest companies, and all of that needs to be protected,

and people just have not been doing that.

Jason Yeh: Amazing. Um, last thing I wanted to ask you, uh, from your seat, you're now in Seattle. You have a lot of connections within Amazon and. Um, throughout the startup ecosystem in California. And I have to imagine that the role that Richard Wolpert, Paul Brico played for you early on is something that you're able to do for, [00:42:00] um, some founders out there.

Are there any names either of people or companies that you want to give a shout out to, or that you think we should be watching? We've done this here and there with some of our guests and had had some amazing success from our early guests. Two and a half years ago calling out the founders that who would be now raising series A's and series B's this year.

Um, any names that you want to share with us? Yeah.

Ian Swanson: out, and they're building out the tools around AI, and I think that's where there's a big opportunity. It's not just about the models and what you see from chatGPT, um, but I would say there's vertical applications of AI. And then there's the pick and the shovels, you know, on how to build to implement. Um, you know, there's a particular company, for example, in Los Angeles body, that's working on like multimodal, you know, models. That's doing some really interesting stuff in generative AI. And, and Stephanie is an amazing leader with, you know, prior exits and stuff.

So I try to affiliate myself, you know, with, with people, not that I've [00:43:00] done this before, but also good people. And, and if you've gone through an exit before, you've shown that you've been able to build out a team. You know, run a culture, build up a culture, and she's an example of that. The other part too is, um, I don't mind paying it forward for when Richard and Paul spent time with me, it's easy for me to jump on a phone call with people.

And so I try to carve out time every week just to sit there, listen, learn from others, and share whatever I can. And perhaps connect the dots, you know, to investors or to even people that they can hire and bring on on their team. I think it's in all of us, if you are listening and you're a CEO, you're on that side, like we have to give back.

And that's one way to give back is for that next generation of founders and making sure they learn from the lessons that, that we've painfully have gone through throughout these journeys.

Jason Yeh: Well, man, uh, I mean, we don't have to look much further for evidence and you doing that than cold outreach from us. You certainly don't remember [00:44:00] me from my days at Greycroft, but like, very open to having this conversation. And we've been able to touch on some things that I think will be super valuable for the people that can listen to this.

So, Ian, uh, really appreciate your time, man. And hopefully we'll be seeing more and more about Protect AI.

Ian Swanson: Awesome. Hey, thanks for the opportunity and really appreciate It.

Jason Yeh: That was my conversation with Ian Swanson co-founder and CEO of protect AI. The top platform for AI and machine learning security.

I hope this episode gave you a new perspective around venture capital. And what it takes to scale your company. After the break, I'll be sitting down with my producer page to talk about the many golden nuggets in this conversation.

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[00:45:00] What's up Paige? Hi Jason. How are you doing? Good. Good. Um, excited to talk about you. I mean, what a guy, like seriously, what a guy, like almost unbelievable. I am very happy that we got to kind of have on, uh, I feel like we're getting into the space with the podcast where we're having a variety of founders come on, which is really exciting.

Um, because I think there's insights to be pulled from people who have [00:46:00] just raised their first round and what's going on currently in the market. And then also people who have now raised multiple rounds of capital, um, that have a lot of different insights on what they would do differently, you know, what they're doing now and how they're raising their rounds now.

So I thought Ian was one of those really cool cases where we got to hear. Kind of his journey through all three of his companies, which was, um, Symmetrix, Data Science, Protect AI, and really get his look into what it means to raise for him now. Yeh, I do like that call out. It's like, I see a lot of value in us telling stories for founders, uh, of like founders that are maybe one step ahead of them because then they can be like, Ooh, I'll just follow behind them.

But then it's also really valuable to talk to someone like an Ian, who is maybe many steps ahead of many of the listeners of this pod. Um, but that's, that's helpful. It's like, can I just see a picture of what is possible? And it's like, in [00:47:00] its best form, what is possible. Cause then I can work towards that.

Um, yeah, these conversations are amazing and Ian Swanson is, well, super impressive. Well, I know that's what, that was my thought. I was just like, whoa, because like, I liked also how you guys did a really good job going through kind of the full journey. I know there was a little bit of bouncing around, but you know, he shared everything from, How he was fresh out of school.

He had a job, he was making good money. He didn't really like it. And he thought of his first idea and found like, um, a family friend who could introduce him to his first investor. And that investor was like, that idea sucks. And then, and then going from. Using that as an opportunity to go work for a startup and have a mentor and learn from someone and he calls it his one year MBA, which I thought was pretty cool too.

All the way to raising his 35 million round for Protect AI right now. So I just really love the variety of this episode. [00:48:00] Yeah, and, um, I forget if we explicitly mentioned it, but, um, he and I crossed paths when I was an investor at Greycroft. And, you know, I was just a junior VC when he was like coming up and at his first exit and then data science.

Well, I was lucky enough to be. In that ecosystem and part of that deal and watch it all happen. Um, but yeah, so I know he doesn't remember me from the time, but I do remember watching him and just continuing to see him level up, like from one to the next, the next, it's almost like, how could you do any more?

And he just seems to be able to do it. Over and over again. But yeah, very fun to hear from his words. He got something. Yeah, totally. And I did have, I wasn't confused on a bunch of things, but I, I kind of wanted clarification on some things that he touched on. Um, I don't know if they were like crazy takes or anything, but something that I jotted down, um, as, [00:49:00] as it was going on was this thought of, The thoughts he was sharing around, uh, giving board seats and how I actually really loved his take around board members and how it's like, he, he was basically saying if I'm not doing my job right, then someone should replace me.

So if the board is doing that, you know, then clearly there's a reason behind it. Or I know that might've, um, I don't know if everyone agrees with that, but I also heard him say that he gives out board seats on his seat around and he kind of said it in a way that was like, People don't do this. So I, I just wanted your thoughts on that or, yeah, is it uncommon to give a board seat on a seat round or?

Yeh, the, the common, the common advice is that you should try to maintain as much control over your company as possible for as long as you can. And, um, what that means is like selling as little of your company as you can and hoarding board seats. So not like, not just. [00:50:00] Willingly giving away board seats because once someone is on the board, like it starts, um, you start essentially relinquishing control of your company because there's another person that votes on company matters.

And, uh, most people have any board at a pre seed and I, you have to look at the numbers, but I would say the vast majority of companies at the seed level don't even need a board and investors at that level aren't. Aren't requiring a board or a board seat. Now that's, I mean, that's the common school of thought.

That's the common advice that's delivered to founders in it. And I think it's there to protect, protect against bad actors. Um, bad investors, horror stories where you hear about founders getting kicked off, um, when they didn't deserve to be kicked off and, you know, knowing like there's a chance that you could be removed from your own company.

And that is a horror story that is told to many [00:51:00] founders. But I think as Ian was describing it, there is a flip side to it, right? Um, I don't believe that. Most investors go into a deal thinking, I want to do this deal so that I can kick Paige out of her company and then control the company. Investors are not operators.

They don't want to operate your company. They want the best operator in the seat that they can, that they can have. And they want the best possible outcome for the company and themselves and their investors. And so usually, When those things are happening, when change of control is happening or when an investor is making moves to change the executive layer, they usually have seen something, you know, they've seen something that gives them pause, that makes them want to make a change.

And so, look, I think there are two sides to every story. Um, certainly there are horror stories. And in, in an Ian's case, look, I don't know if I have the [00:52:00] general advice that you should set up a board at the seed level, but what he's saying is real. It's just like. If you bring the best partners on board as investors, you should want them close to the company.

You should want them to work alongside you and be working in concert to have the best outcome possible. And like he said, if I have someone that is close to me and we're working together and they see something and we see something where it's like, I'm not the best person to be running this company, then he's right.

He's like, we should all be working to try to find out who that is. And I think a lot of times egos get involved. It's like, I was the founder, I was the initial CEO. There's so much identity tied into running a company that when someone says. Jason, you're not the right CEO for this company, even if it's right, it can be very hard to hear.

And so look, I think it takes a lot of maturity. I think it takes three companies, you [00:53:00] know, and, and to be like, look, I want real partners. I want to build a big company. And I want, um, I want someone close to the business early on so that we can drive towards the best outcome that we can. And I'll, I'll tell you, One personal story is, um, and my last company, I ventured that company because I am a good fundraiser.

I was able to raise capital on my terms and I was able to fully control the company, no board, no nothing, um, sell very little of the company. And I look back on it and I think we would have gotten to a better outcome had I actually brought investors in closer, like, and had the company had the investors maybe take a board seat early on, engage with me more and sort of push us as a team in the right direction, as opposed to being like, no, no, we know everything we can get this all done.

We don't need investors. So long winded way of saying. If you're building a partnership with [00:54:00] investors, then you shouldn't be scared of them. You shouldn't be scared of them being part of the, the, um, management of the overall direction of the company. That's what you're bringing them in, in there for. And so, um, that's something for everyone to learn from.

Whether or not that means that You should give away a board seat at the seed level. It certainly means that you should be working closely with your investors because they're part of the team too. Yeah. I also liked how Ian was like, listen, I'm, I'm a stakeholder in this company too. You know, like I want this company like he put the company before himself, which I think.

Clearly, so far, that's worked out pretty well for him. He has ended up being the CEO, I think, for all three of his companies. Um, but just even having that mindset in there of like, okay, if there ever comes a day where I'm not best fit for this, then I'm not best fit for this and we should find someone who is.

I just think that's very honorable and I like that. Um, I also feel like, It's just one of the, to me, how I took that advice is like, if you [00:55:00] have a gem of an investor that you just, you click with, you trust, you feel like they're going to push you in the right direction, then, you know, if the only thing stopping you is, Oh, I shouldn't give a board seat away yet, then maybe you can rethink it.

And that's like, that's all I kind of took away from, from that. Another thing I kind of wanted to get clarification on that I honestly didn't know much about is this idea of like outside investors or outside investor firms, because on Ian's second company, Data Science, he ended up, as you heard in the episode, having this crazy weird round, like where he, it started off as He thought the conversation was a joke that he was having with this guy of like, I'll give you 10 million for it.

I'll give you 25 million, whatever. And they ended up doing the round for 25 million from an outside investor. And I liked how he spoke on the ups of that, the downs of that. Um, some of those downs being, you know, he felt like they kind of [00:56:00] had to train the investors and how to be investors. Um, and like this idea of having too much money and using it too fast.

And, and I think that gave a lot of really good insights for founders. But I also just wanted to ask you, like, is this something that you see a lot? I'm assuming it's not something you see a lot, but when you do see it, how do these, how do these even happen? I just, I'm, I'm kind of confused, honestly. I think he's talking about sort of atypical investors, right?

Um, most times when you're raising capital for a high growth tech startup, you're talking to high growth tech venture capitalists, um, who invest at different stages. They understand the motion. They understand the expectations. They understand what it takes to get a company from Let's say pre seed to a seed if I'm investing at the pre seed or from a seed to an A if I'm a seed investor and so on and so forth.

Every, every once in a while, there are people with money, organizations with [00:57:00] money who happen to hear about an opportunity, uh, and then you get what these, what, what Ian was talking about in his experience, where he ran into a sovereign wealth fund in the Middle East or something like that. And, um, they get enamored with the idea of investing in tech, even though that's not their core competency, even though that's not something they've done.

And one thing to point out is that I've grown up in the world of venture capital, especially call it pre seed all the way to series B. And we're talking about million dollar rounds, 2 to 4 million dollar rounds, 5 to 10 million dollar rounds. And when we're talking about big money, we're talking about 10 to 20 million dollar series B rounds.

It's like, Oh my God, a lot of money. But if you take a step back in the world of finance, Sub hundred million dollar rounds are tiny rounds to some people. And, uh, the same motion and effort it takes to [00:58:00] raise a 2 million round. It's kind of the same motion and effort it takes to raise a 200 million round.

It's just, you're talking to different people and vice versa in terms of, uh, As an investor, putting a 2 million dollar check in versus a 200 million dollar check, it can feel very similar. It's just we're adding a few zeros, right? And so, um, that's just a side comment. But there are these times when, through the course of networking, through the course of running your business, you may Run into somebody who's like, who gets enamored with the idea of investing in your company, who doesn't have any exposure to it.

In this case, it seems like, you know, a Middle East fund who, like I said, is used to writing way bigger checks. So when they met an experienced entrepreneur like Ian doing something interesting around data science. They're like 25 million, dropping the bucket. That's like, and so this can happen and I've seen it happen multiple times.

Does it happen a [00:59:00] lot? No. Right. It's good that we, we, you know, Ian talked a little bit about the pros and cons. On one side, the pro is like, more money than he was expecting, right? And, you know, that can, in some ways, solve a lot of problems. In a lot of ways, it doesn't solve a lot of problems, right? So, um, there is a real trap around overcapitalizing a company.

It can be, um, it can feel like that money is burning a hole in your pocket, so you just kind of increase spend when the company isn't prepared. To, to put that sort of money to work. And so you become a little bit loose with how you make decisions. And then all of a sudden you're burning away more capital than you need to.

And, um, you know, maybe not making the progress that you might had you been more disciplined with less capital. Also, whether it's a Middle East fund that usually invests in real estate. industrials, or let's say, you know, [01:00:00] investing in a 25 million round or a dentist, a dentist who had an extra 50, 000, who is investing in your angel round.

These are two types of investors that don't know what high tech startups are about, don't know what to expect. And in those situations, While it might've been easy to get the money because they're like, sure, whatever, you might find that it's harder to work with them, right? They might be bothering you about revenue when revenue is the last thing that's on your mind.

They might be all of a sudden on the dentist side, worried about the 50, 000 because they thought it was like putting money into a CD or a, you know, a public stock where it's like they can get their money out. You know, they, they didn't expect that. And on the Middle East Fund, they might be You're just asking the wrong questions, not actually driving the value that a, an experienced investor in your industry would be able to drive.

So yes, does it happen? It [01:01:00] does. There are, there are good things about it. There are bad things about it. I think Ian ended up managing it, uh, relatively well, but yeah, it's a, it's a funny thing that happened to him. And I'd be curious if you would do it again in the future. Yeah, I think, how I think about it is, if I was going to do that, I would have to have a close group of people, like, in the VC world that I could get my feedback from them.

Like, I, that would have to be How I thought about it, which I'm sure Ian figured out a way to do that. It's just get information like, okay, here's the investors for the money. And then here's my like mentors and my people who are actually going to give me feedback around what to do. So it kind of is double the relationships then.

But I guess if you have the right people, then it could work. And I want to, What makes me, makes my heart, you know, so happy. It's like, you're really growing up in this world and that's exactly how [01:02:00] you do it. If you're going to play that card, then realize that you still need the support and find your other advisors, find the other people to get the feedback and advice that you need if it's not going to be your main investor.

So, great call. Thanks. And then I kind of wanted to tie this back to where Ian is now, which is, he just raised his 35 million round for Protect AI, and I liked how he, he tied it back to this point that we were just talking about, which is, he's still sitting on that 35 million and taking his time with it.

He's figuring out, he's strategically thinking about how to use this capital. I think that's genius, but I did have a question that came up around it is, is there a deadline For using capital, like I know there's probably like hypothetical deadlines that investors are going to push you in, but is there like an actual deadline?

That's a very good question. The answer is. No, not a real deadline. Um, but, but [01:03:00] investors have their own bosses and they are, they need to demonstrate certain progress in their own portfolio. So they want to be able to report on the money they put into Protect AI or the money they put into your company or whatever.

And in some ways you could, in some situations you can see investors Kind of push in order to deploy the capital faster, use it to grow, use it to invest in certain growth areas. Um, but I would imagine in, um, in Ian's case, the investors that put the money in trust Ian. And because Ian is taking this approach to grow and protect AI, before he took that check in, I'm sure he had this conversation with the investors saying, this is how we're going to run it.

Like, the expectation is that we are going to earmark the first X million dollars, first 5 million to run this [01:04:00] motion and get to this level. The rest of that 30, you know, that other 30 million. Is earmarked for the next phase. And we're not going to be, you know, we're not going to be spending like we need to spend 35 million in two years necessarily.

Um, I think that's one big call out for, for anyone who's going out to fundraising, whether it's you were going to raise 10 and ended up being able to raise 35, or you went out to raise one and you were able to raise four. I think there's a mindset that everyone can have, which is like, let's not get ahead of ourselves.

Let's not use, let's not take the additional money that investors were willing to spend as indication that we are further along in the company than we actually are. Because of that, investors need to, founders need to say, we are where we are, what is the right approach to getting to the next stage? Well, if I raised four, even though I only needed one, we're going to take the first [01:05:00] 1 million and run it.

Run the company the way we expected to run it. And if we hit the milestones, it'll be like we have access to another 3 million. And I like the approach. This is not everyone's approach, but I like thinking about oversized rounds as we just skipped the next fundraise. As in, if hit our milestones, then we get the money that we were going to raise in the next round anyways, and that's when we'll start spending that money.

So, that's my approach to oversized rounds. Um, I'm not sure I've got a chance to ask Ian that, but I, but I would imagine he has a similar viewpoint on that. I mean, that, that's a wrap for me. Like, I think that was, that was a great piece of advice to end it. That was. I like that. I would do that too.

[01:06:00]

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