Have you ever poured years of your life into something, only to realize you’ve completely lost yourself in it? Yeah. Most entrepreneurs know that feeling way too well. And today’s guest has lived it, learned from it, and built something pretty incredible on the other side of it.
In this episode of The Happy Hustle Podcast, I sit down with Nic De Castro, founder and CEO of LandTrust, a land sharing marketplace that connects hunters, anglers, and outdoor enthusiasts with private landowners across the country. Nic spent most of his twenties working in early-stage tech startups, living out of a suitcase, crossing a million flight miles before he ever got serious about the things he actually loved. He grew up spearfishing in Southern California, moved to Montana in 2016, and pretty much immediately stumbled onto the idea that would become LandTrust. Six and a half years later, he’s running a platform with over a million and a half acres, tens of thousands of users, and a lean team that’s growing faster than ever. He’s also a husband and a dad to three girls, which, trust me, comes up in the conversation in the best way. This episode matters because Nic isn’t some billion dollar exit guy telling you how easy it all was. He’s in it right now, doing the work, navigating the hard stuff, and being real about all of it.
One of the biggest things Nic drives home is this: don’t make your company your identity. It’s so easy, especially as a first time founder, to let your business become who you are. When it’s doing well, you feel great. When it tanks, you feel like a failure as a human. Nic’s been there. He’s had investors he shouldn’t have taken money from, he’s had near acquisitions fall apart, he lost 15 pounds in a month during one of the hardest stretches. And what got him through it wasn’t hustle. It was faith. Surrendering control, trusting that God’s plans are bigger than his plans, and slowly learning to hold the business a little looser.
On the venture capital side, Nic is refreshingly honest. His advice? Don’t take outside money unless you absolutely have to. Once you do, you’ve got partners, you’ve got a board, and you’ve got pressure that changes everything. He’s navigated some genuinely tough investor situations and come out the other side, but he’s clear that bootstrap founders have a freedom he genuinely envies. If you’re thinking about raising capital, this part of the conversation alone is worth your time.
Nic also talks about how LandTrust is using AI in a way that actually makes sense. They built an AI trip planning assistant named Buck, and the goal is to have 85% of all bookings happen through him by end of year. What’s cool is how Nic thinks about trust with AI agents. Same as hiring a new employee, you check their work, you ask why they made the decisions they made, and over time, as they prove themselves, you give them more room. It’s a practical, grounded way to think about bringing AI into your business without just slapping the word on your branding and calling it a day.
And then there’s the balance piece. Nic started LandTrust full time on July 1st, 2019. His first daughter was born August 5th, 2019. One month later. He was waking up at 3:30 in the morning for years. He’ll be the first to tell you the balance wasn’t great back then. But he’s course corrected. His team is the smallest it’s been in years and they’re growing faster than ever. His word for it is sustainability, not grinding until you break, but building something you can actually show up for, year after year, without losing your family or yourself in the process.
If you’ve ever felt like your business was swallowing you whole, or you’re curious about building a marketplace from scratch, or you just want to hear from a real founder who’s figuring it out in real time, this episode is going to hit home.
Go listen to the full episode at caryjack.com/podcast. You won’t regret it.
What does Happy Hustlin’ mean to you?
Nic said working and having a vacation and being good at what you do and getting joy out of that, again, using the skills and talents that God gave you, that’s what we should be doing, but also not letting that whole thing take over your life and be who you are.
Connect with Nic
Find Nic on his website: https://www.landtrust.com
Connect with Cary!
Get a copy of his new book, The Happy Hustle, 10 Alignments to Avoid Burnout & Achieve Blissful Balance
Sign up for The Journey: 10 Days To Become a Happy Hustler Online Course
Apply to the Montana Mastermind Epic Camping Adventure
“It’s time to Happy Hustle, a blissfully balanced life you love, full of passion, purpose, and positive impact!”
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