Living Out Hospitality: Lessons from a $250M Entrepreneur
I spent Saturday with an incredibly successful entrepreneur, Nathan Barry. But what impressed me most wasn’t his net worth ($250M+). It was his sense of hospitality in how he lives life.
Some valuable takeaways here. Let’s dive in.
A few months back, Nathan invited me to join him on his podcast next time I was in Boise. Well, a couple days ago, I found myself in Idaho filming a mini-documentary on the train car project for CNBC, thanks to a thread I shared that went viral and led to coverage in outlets like Vice, NY Post, Business Insider, Daily Mail, and more. A producer at CNBC read one of these articles, and suddenly, I was headed to Idaho! This is the new way media works, and I love it.
On set at Car 306
“Build it, [I’ll add: share it], and they’ll come!”
After a fun (but exhausting) 24 hours in Deary, I flew down to Boise, and Nathan invited me over.
I arrived at his unpretentious farmhouse just in time for a hearty family breakfast. Nathan, Hillary, and their three boys live on a spacious 9-acre homestead alive with chickens, goats, and gardens they’ve cultivated over the past seven years—a true labor of love. (Not where you’d expect a tech CEO worth hundreds of million to live).
So how did I meet Nathan, and who is he?
In June 2022, I had no social media presence, newsletter, or email knowledge.
I’d just opened Live Oak Lake, which was gaining traction with social reach and direct bookings. Some random guy (@thesamparr) texted me one day. I told him about my business, and a few hours later, he tweeted about it.
Just minutes after Sam’s tweet, I got a phone call from an unknown number. The caller was genuinely interested in STRs and impressed by what I was doing. He told me he ran an email software company and wanted to stay in touch. His name was Nathan Barry.
Nathan and Sam onstage at Craft + Commerce - 2022
A few weeks later, I met both Nathan and Sam in person at ConvertKit’s annual conference.
Since then, email has been life-changing for me, and I owe a lot of that success to these guys. They’re two of the best marketers in the world, and both wonderful humans.
So, back to the story…
After breakfast, Nathan and I hauled furniture to his new hangar (he’s a pilot) and assembled it. We chatted business, life, farming, and flying.
Assembling furniture in the new hangar
Later, he took me to the new Kit Studio downtown. Building this was a really bold move—requiring a huge investment. This first one (he has more planned) features five uniquely designed, pro-lit, multi-camera recording studios—completely free for kit users to record podcasts, courses, and content.
One of the 5 studios at Kit Studios Boise
This studio project is a fantastic example of how a business can practice unreasonable hospitality. What other competitor or similar company is doing this? None that I know of. It creates a moat around the core software business while empowering creators to level-up their content, earn more, and save money. People are flying in from all over just to record here.
Nathan and I ended up recording 3 hours of conversation (2 entire podcasts), then drove home for a fantastic dinner Hillary had just finished preparing. We even squeezed in a round of pickleball before calling it a night. I stayed in their cozy guesthouse, rounding off an incredible day.
As I reflect on all this on my flight home, I want to share a few takeaways:
Act Earnestly and Immediately: When Nathan first heard about me, he found my number and called immediately. His genuine interest and immediate action meant a lot, especially to someone like me who had no audience or platform at the time.
Go All-In on Email: Email has been transformative. It fueled direct bookings at Live Oak Lake and my education/consulting business @xhospo. An engaged list is an invaluable asset, no matter the business. Go all in on it!
Hospitality as a Way of Life: Nathan lives hospitality in every area of his life. He leads with kindness and generousity. It shows in the way he makes business decisions, in the way he treats his family, his employees, every customer (and every non-customer too). He’s unreasonably hospitable, and it’s infectious.
In a world where winning at a high level often changes people for the worse, Nathan is an exception.
You don’t have to be cutthroat to win. Focus on what truly matters—kindness, decency, and serving others—and you’ll win not in spite of it, but because of it.
Keep winning, Nathan! And thanks for your example and friendship.
After our recording marathon
—Isaac
P.S. I use and highly recommend Kit for email and light CRM/digital product software. This post isn’t sponsored in any way. You can check them out and sign up completely free by clicking here!