About our guest

Tim Prugar is the Head of Product and Engineering at fileAI, leading the technical teams who are solving the problem of AI data preparation.

Previously, Tim was the VP of Operations and Product Owner at Next Caller (YC14) where, as a member of the leadership team, he grew the company and guided it to a successful exit to Pindrop Security in 2021. While at Pindrop, Tim functioned as the Chief of Staff to the CTO, bringing scalable processes to Pindrop’s Product and Engineering efforts. Tim relocated to Singapore in 2022 to set up Pindrop’s Asia-Pacific and Japan office, functioning as the lead technical resource in the region.

Timestamps

(00:00) Part 1 Highlight and Introduction to fileAI and Tim Prugar.

Watch Part 1:

(00:46) What sets fileAI apart from other AI startups Tim has helped build

(03:23) Building AI in Singapore and Southeast Asia vs the US

(06:52) Bringing education and coaching philosophies into startup leadership

(10:12) “Life or death” moment in Tim’s career

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Directed by Paulo Joquiño

Produced by Paulo Joquiño

The content of this podcast is for informational purposes only, should not be taken as legal, tax, or business advice or be used to evaluate any investment or security, and is not directed at any investors or potential investors in any Insignia Ventures fund. Any and all opinions shared in this episode are solely personal thoughts and reflections of the guest and the host.

Part 2 Transcript

Opening Highlight and Introduction

Paulo: Hi folks. Welcome back to On Call with Insignia, we’re here with none other than Tim Prugar who leads engineering and product at fileAI.

You don’t know what you don’t know. I think it is great that the customers are letting you guys know. I remember a conversation with another product leader and she said the best customer to have is the one who complains. It is always good to have feedback.

I wanted to switch gears a little bit and move from fileAI to also talk about you as a product leader. You mentioned you’ve worked in a couple of AI companies before this. It’s not your first rodeo, but is there anything, I guess the obvious question is like, what sets fileAI apart from the past AI adventures you’ve had, but maybe also is there anything that you’ve been bringing into fileAI from these past experiences as well?

What Sets fileAI Apart

Tim: Absolutely, I think so. I had the privilege of working at Next Caller, which was a YC 14 company, which was then acquired by Pindrop Security which was an Andreessen portfolio company. IVP just crossed a hundred million ARR. I’ve seen, joined one at the seed stage, joined one post series D and now joined fileAI.

I think what I bring from that is a few things. One, I’ve seen firsthand what happens when you listen to engineers and let them build. I think fileAI is a deep tech company that deeply trusts the engineering team and the product team, and that’s something I’ve tried to bring from my previous experience to amplify and grow.

I think another thing is just comfort with the growing pains of a scale up. Having been in a startup, having been in a scale up now at a scale up at fileAI, there are inevitable pitfalls and mistakes you step in and great opportunities you recognize and run to. I think my experience brings to fileAI an excitement for what’s happening, that when delivery teams feel stressed because we’re delivering on 10 enterprise deals at once. That’s really exciting. That’s a place you want to be. You don’t want to be bored wondering if a deal’s going to come in. You want to be figuring out how to make it work and how to deliver a truly exceptional customer experience.

Then I think the third is just being unapologetically bold about putting new technologies into production. At Next Caller we did it with AWS’s SageMaker at Pindrop. It was probably the most intense research institution I’ve ever worked in. The way that new models were productized and put into production, and then here at fileAI of the velocity with which generative AI in general is working.

But the demand that senior management and frankly the engineering team has for, let’s test this. Let’s try this, let’s roll it out. Let’s make that customer experience better. Because you cannot wait in this environment. You need to move fast, you need to move definitively, and you need to learn really quickly.

I think those are the things that I bring from my previous experience. Also, frankly this works too hard not to have fun. I enjoy working with people who are kind, collaborative, fun, funny, and have a high bar for excellence. I’ve been really fortunate to have that at three straight places, with fileAI being the present.

Building AI in Singapore and Southeast Asia

Paulo: Speaking of going from what you’ve taken from your past experiences, is there anything new as you’ve joined fileAI that you’ve discovered, especially working in Singapore, the different geography, culture, whatnot.

Tim: Absolutely. I think the talent here in Singapore is exceptional. Incredibly fortunate with the team that I have, both that I inherited and was fortunate enough to find and build and hire. I think the biggest adjustment for me was just navigating the different regulatory privacy technology landscapes in your backyard.

You could probably tell I come from the United States. I’m accustomed, I grew up in Kentucky. I’m used to my neighbors being Indiana, Tennessee, and Ohio. Here my neighbors are Malaysia, Indonesia and Thailand, which are completely different countries. Just thinking about that as a product and an engineering leader of, it’s one extra layer of complexity when you’re thinking about how and what you build. What are the regulations of the places you’re shipping what microservices are available? What does your deployment model need to look like?

Honestly, the amount that I’ve been able to learn. That I have a very gracious and compassionate team that they’ve been teaching me as well. It has been just a massive career development for me, and I think one of the things that I’ve learned the most is stepping into this role.

Paulo: You brought up a good point actually. About, I guess it also adds to the whole moat of fileAI as well. Having been able to navigate all of these differences maybe. Just for our audience, can you give like an example of how like the differences in kind of perhaps regulation or how people like view data privacy and all that have

Tim: Absolutely. In the United States you have an absolutely massive market. No federal data privacy laws, particularly you have localized like state-based laws that you have to comply with, like CCPA. Here, you have PDPA in Singapore, you have MAS and IMDA’s trusted AI framework, which is guidance that you’re expected to abide by in Indonesia.

You have different cloud services that are and are not present. Really strong data residency and data privacy rules working through the OJK there. Australia, extremely strong AI data, privacy laws working in Japan, expectations there. You really have to think through all of this, am I being authentically an excellent, highly secure steward of data?

We’re SOC 2 Type 2 ISO 27001. We’re actually going above and beyond what is expected of companies at our stage. By getting ISO 42001 as well as SOC 1, Type 2 in our next audit cycle, which is happening currently. Thinking through how does data privacy, how does privacy by design, how do regulatory considerations not come up as things you’re trying to comply with after the fact, but that are fundamentally built into the DNA of how you build your products and how your team thinks about meeting customer needs.

Paulo: I think that’s pretty interesting. I like how you word it like a steward of data. Normally I think in the tech space I think the business model of being like an asset light platform and not really having, being like low touch is pretty predominant.

But at the same time, I think it’s always good for companies to, as they mature, have greater ownership and responsibility over the things that happen on their platform, data included.

From Education to Engineering Leadership

Paulo: In your career previously you weren’t always in AI, you weren’t always in software, you were previously also in education. I think you mentioned wrestling as well. I guess for entrepreneurs and tech leaders, I think the folks I’ve spoken to on this podcast in the past have often cited athletes as sources of inspiration. Where were they learned from in terms of leadership and all this? Maybe you can share a little bit about how that whole experience as a wrestling coach has impacted the way that you managed, engineers and, sales and, all that.

Tim: No, I absolutely wrestled my whole life and had a massive impact on me as a person and a leader. I don’t know, based on my record in college, if you call me an athlete but I certainly was a participant. No, I was very fortunate to work at a number of schools and with a number of absolutely exceptional educators. I think one of the things that I bring from my life in education and coaching to my work is there’s this great book Teaching as Leadership, and it’s the idea that there are so many external factors working against classroom teachers.

One can either dwell on those or realize that you are the ultimate owner and leader of the four walls of your classroom. I carry that over to the startup world. Where there are so many reasons why you should fail. There are way more headwinds than tailwinds. There are naysayers, there are changing funding environments.

There’s always a problem. What you can focus on is your locus of control and focus on being a leader within your organization. I think that’s really important. Working with middle schoolers high velocity decision making is very important. When you’re dealing with problems all day, every day, you have about three minutes to solve one or another one.

I actually think startup life’s similar. The more that you hem and haw, the more those decisions pile up and you need to rightly or wrongly move quickly. Also working with middle schoolers, you get very accustomed to being told you’re wrong. That pretty much happened all day, every day when I was a teacher, and I think listening to what people are saying when they’re giving you feedback. What are they trying to understand? What are they experiencing and how do you infuse that into your practice?

I think that’s one of the places where whether it was listening to teachers about the best way to run things or students about the best way to run things, it’s why I now listen to engineers and salespeople. I really take that feedback and that advice. Also there’s no substitute for humor. You can make someone’s day or break someone’s day by how you respond to them and interact with them. It doesn’t matter if they’re a 50-year-old hardcore COBOL engineer or a 12-year-old wrestler.

It’s the same mindset and the same thing. But that’s a lot of what I’ve taken and factors in quite a bit. I think I am an educator at heart. Which means I’m always learning frequently wrong. I listen really well, and every once in a while I get it right. That’s what I bring to fileAI from my time as a teacher and a coach.

Paulo: I haven’t really encountered that many people who have come from that background and move into software or tech. It’s very interesting to see how you’ve translated a lot of the mindset especially.

A Career-Defining Moment

Before we wrap up our conversation I always like to ask our guests about a make or break moment in their career and what they’ve learned from that. Like anything, do or die. Maybe not literally life or death, but a really pivotal moment from your career that maybe our listeners, especially those who are working at startups could learn from.

Tim: It wasn’t life or death, but it was life or death of the company. I was at Next Caller in 2017, 2018, and we had this product that was doing solid ARR, but we were noticing problems. The margins weren’t great. Our customer base, we didn’t really have an ICP. None of our sales seemed replicable. We had this other product on the side that was high margin, low revenue, but being used by a major bank.

I think about this moment a lot because I think it was some of the most courage I’ve seen from a leader the CEO at the time in Ron Caroni when we were talking through, what do we do? Had we stayed the course with the high revenue product, we would’ve plateaued. The company would not have become what it did. If we took a risk and focused on the high margin replicable use case enterprise product, we had a chance at being a rocket ship.

We have, in talking about risk, I think Ian correctly sussed out the risk isn’t staying the course. Like the risk isn’t changing course. The risk is not changing course. This is the clear answer. The data shows it, the opportunity shows it, the upside shows it. I think having the courage to actually end the life of one product to focus 100% of company resources on the other in the following year, we 6X’ed revenue and we doubled it year over year after that until we were acquired.

To me it was absolutely the right decision and the amount of courage. Who knows the number of behind the scenes investor conversations that had to happen. But that idea of, sometimes pivoting, changing course, making a bold decision, that actually isn’t the risk. The risk is staying the course, pretending everything’s fine when things clearly aren’t.

Paulo: Hindsight’s 20/20, but obviously not knowing any of what you guys achieved afterwards is certainly daunting, let’s say the least. No. On that note, hopefully for those who are listening, you guys can get inspired by that story and maybe not as big of a decision, but even in the smaller details find some courage there.

On that note, thanks so much, Tim, for coming on the show. I appreciate it.

Tim: Thank you for having me. Quite the discussion.

Paulo: For those who are interested to learn more about fileAI, Six letters, file.ai, type it in your browser. You’ll be able to test out the platform. By the time this podcast is out, you guys should be able to try out MCP as well.

As Tim has mentioned, don’t be afraid to leave comments and feedback. I’m sure you’ll please whether it’s on our platform or there’s and hopefully, get to have you or more leaders from fileAI on the show in the episodes to come.

Tim: We’re chock full of leaders I’m sure you will.