Mindtrip Blueprints: How a 12-Person Founding Team is Building the Future of Travel AI

BuilderOps Blueprints is a newsletter on company building foundations for early-stage startups by Costanoa Ventures, a VC firm that backs builders across data, dev, and fintech. Throughout this series, Costanoa's BuilderOps team interviews founders and startup leaders, showcasing their superpowers and learnings on all things company building.

For our latest edition of BuilderOps Blueprints, we interviewed Andy Moss , a 5x founder and currently the Co-Founder & CEO at Mindtrip, Inc. , who recently announced their seed round in TechCrunch: Mindtrip wants to become your AI travel agent.

Quick overview on what Mindtrip does for those who don't know.

Mindtrip is your personal AI travel assistant – an all-new travel platform built on top of Large Language Models (LLMs) to simplify the way travelers discover, plan and book travel all in one place. We’re taking sign ups for the waitlist for those who want an early look: https://mindtrip.ai/?

GenAI is top-of-mind for most people these days. What is the hardest challenge that you’ve overcome in the early stages of building Mindtrip??

We are building our application on top of generative AI and LLMs. So the biggest decision we had to make was if a team of highly talented engineers, who were not AI specialists, could adapt and learn the APIs, the LLM models, prompts. We spent some time evaluating this upfront, and Madison Hawkinson on the Costanoa team helped introduce us to a bunch of folks. We eventually concluded that with great engineers, they could learn how to integrate the AI. And more importantly, we figured out that anyone who was a PhD sort of math wiz probably didn't want to come and work on an application on top of the LLM. They wanted to be at one of the companies that are actually running the LLMs.?

And the other thing we discovered is the more AI research type of people actually aren't as good at building products. That's a different type of engineer that wants to do research and the math stuff, and they're having that moment at OpenAI or Googlebot or DeepMind or Anthropic.?

When coming from a traditional coding world, we’re very used to going into the code to fix a bug. With LLMs, we're finding that you have to be able to live in a world of uncertainty a little bit more because what the LLM comes back with is not identical every time. You can ask the same question 20 times and you can get 20 different answers. And none of them would be wrong! I think it's just very different from how engineering has been done in the past,?

It’s a mindset difference the engineers have had to deal with.?

How has this been different from your previous founder journeys??

Most large companies have trouble with innovation. A lot of them were actually pretty bad at making the move from desktop to mobile when iPhone came out. They actually had to buy companies in order to get that talent and extend their products in that way. We're looking at travel companies that took exactly that path and didn’t have the skillset inhouse.?

In today’s world, there’s a whole different level of complexity and uncertainty where shifting to LLMs is a much bigger engineering challenge than simply shrinking stuff down to fit on a smaller screen with touch capabilities.

If you're working at a company that is used to having a lot of predictability and controls with a Chief Security Officer saying, “Well, of course we have to know what it's going to do.” And it's basically, “Well, we don't actually know exactly what it's going to do..” That's probably pretty scary if you're working for a Fortune 500 company.?

So we think that's a huge advantage for us as a startup because it's going to be very hard for those kinds of companies to do what we’re doing, or at least do it quickly.

Now that you’re starting your fifth company, what would you tell your first-time founder self that you didn’t know then?

This is actually pretty real as I am witnessing my son, Matt Moss , starting his first company, Locket.?

Locket took off really quickly with millions of users, and for a period of time, it was just Matt, which was pretty daunting for a 22-year-old right out of college. His biggest challenge at the time was figuring out how do you actually build a team?

When I assembled the Mindtrip founding team, I had the luxury of having worked with all these amazing people across multiple different companies. As a multi-time founder, you already have a network to pull from.?

At the beginning of Matt’s founder journey, he thought, “I'm just not really good at hiring.” But the reality is, hiring is just really hard, especially if you don't have the network to start with. And so we supplemented him with a couple of people from my network to help out. Fast forward 6-9 months later, he has an amazing team now. And if he starts another company down the road, he's going to be in great shape because he has this core group of people–perhaps even co-founders–and it's going to be a little less lonely.

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There's a lot of things like legal or payroll on the corporate side, or even fundraising where we were very keen on getting the team back together, which included Costanoa. We already knew we had good chemistry at the board level and saw the world the same way about culture, product, and all those kinds of things. So it made it easy to not look too far. We decided that as long as the price was in the ballpark of what we think is fair, then we'd much prefer to do that than try to do a beauty contest with 20 firms and maximize the last penny on valuation.?

The key thing is, if you've done it before, a lot of the company formation set up becomes much faster, leaving much more time to focus on meeting partners and advisors in the travel space, focusing on the product, and getting the team built.

So I guess my biggest lessons for any first-time founders would be:

1. The first time is actually the hardest time.?
2. Hiring cold is really hard and it just takes time. Stay at it and if you have a good product, you're going to have that network of people for a lifetime.??
3. Having great co-founders is super helpful vs. going at it alone.

One of your superpowers is building an incredible team. Tell us about how you’ve been able to persuade such impressive leaders to leave their previous roles to start something new with you.?

We knew pretty early on that we're in a race with AI. We think there's going to be a whole wave of products that just couldn't have been built before and are very consumer-focused, new types of UX built on top of the LLM platforms. So, time to market is kind of key, let alone if there's somebody else in travel that's also thinking of doing the same thing. So we went deep on the size of the team for Mindtrip right from the outset.?

Right now, our focus is on building fast, and the Mindtrip engineering team is 2-3x the size of what we did with my previous company, Roadster, which was very intentional.?

We also have a 12-person founding team, which is pretty rare. I’ve worked with all of them in one or more of my previous companies. For example, Garrick was a co-founder at Shopstyle, but then went off and did big tech and ended up running Gmail engineering at Google, where he had close to a thousand engineers working for him. After ShopStyle, Manish became one of the key ops guys for LinkedIn pre IPO and stayed at Microsoft. But both wanted to get back to building stuff and had really enjoyed working as part of the ShopStyle team so they are now back to startup life as co-founders at Mindtrip.?

We’re currently very focused on building our product, so we have no need right now for certain operational roles while we’re focused on thatt. We also have two fantastic designers that again, as part of that group, we've worked with all the way back to the ShopStyle days.?

But across marketing, finance, HR, and business operations, including COO and CMO roles, we've already got five really great executives lined up from past companies that will be amazing at the right time. It doesn’t make sense to bring them onboard now, but we’ve brought them on as advisors that can convert to full-time when we are ready.?

What is the biggest productivity hack that you still use today?

I don't know if it's a productivity hack, but philosophy-wise I try to avoid as much formalized process for as long as possible. Especially in the early days, I prefer doing things the most simple way vs. a more rigorous, written, procedural approach more common at bigger companies. You're better off just having a bunch of people that are empowered and will just jump on a Slack or a Zoom to solve problems as they come up, as opposed to regularly scheduled meetings. The engineers have a day in the office where we try to get together and cover a bunch of topics, but there's no fixed agenda. It's making sure we're co-working for certain times. That changes over time as the company gets bigger and you get to 150 people, like we did at Roadster. But I am always the one who is pushing for less as opposed to more process until a more structured approach becomes really necessary.?

What is something interesting that people wouldn’t know about you by looking at your LinkedIn profile??

With Mindtrip, everyone on the team loves to travel. One of our advisors just did 30+ days on the Camino de Santiago, from France to Santiago in Spain. He did 750 kilometers, and I joined him for the last 8-10 days of that and did about 180 kilometers. That combined travel and hiking, which is where I spend most of my free time now that I’m an empty-nester.?

BuilderOps Blueprints is a newsletter created by the Costanoa?BuilderOps team. Stay tuned for upcoming features!