How Troy Daily Scaled to 70+ STRs (and Kept His Sanity)

**Jasper Ribbers:**Welcome back to another episode of Get Paid For Your Pad. I’m Jasper Ribbers, and today I’m joined by a long-time friend and partner, Troy Daily. He’s the founder and CEO of Elevated Homes and Hospitality, based in the beautiful lake town of Traverse City, Michigan. Troy, welcome to the show.

**Troy Daily:**Thanks for having me, Jasper. Excited to be here.

Jasper:
You've been in the short-term rental game for a while. I think we started working together around 2021, right after you joined Legends X?

Troy:
That's right. I got into my first STR investment in 2017 with two friends. We bought a duplex, and I handled everything, the listing, cleaning, guest communication, maintenance. About six months later, we bought another, and I was still doing it all solo.

Jasper:
Sounds like classic hectic host mode.

Troy:
Exactly. Then we bought a 7-unit complex. That pushed me into chaos. I started outsourcing housekeeping, but I was still overwhelmed. That’s when I got my real estate license and joined Legends X in 2021 to figure out how to scale without losing my mind. I think I had 18 units at the time.

Jasper:
And now you’re managing over 70 units. That’s incredible. You were also our first RPM client. I remember those early pricing conversations.

Troy:
Yes. I didn’t have time to focus on pricing, and your team stepped in. That changed everything. Between Legends X, the coaching, and RPM, I had the support to grow fast and smart.

Jasper:
I remember you had 23 units when we started RPM, and now you’re close to 100. Did that support free you up to focus on acquisitions?

Troy:
Definitely. I hired an operations manager in late 2022, who also took over housekeeping. We brought all cleaning in-house to control quality, which was a massive shift. Creating those systems was intense, but it paid off. Our real growth started Q1 2023, and we’ve doubled each year since.

Jasper:
That’s impressive. What’s next for Elevated Homes?

Troy:
Now we’re being more selective. We’re onboarding a luxury 15-unit condo-hotel. It’s high-end, new construction, and aligns with the caliber of owner and guest we want to work with.

Jasper:
I remember we looked at that project a year ago and ran some projections.

Troy:
Yep. It took time due to construction, but it’s almost ready. Should go live in June.

Jasper:
You also run several other businesses, bike tours, kayaks, wine tours. Have you always been entrepreneurial?

Troy:
Yeah. My parents owned the first Kilwins candy store. I grew up learning everything about running a business. After college, I opened my own Kilwins in Virginia, ran it for four years, burned out, and moved back to Traverse City. Since then, I’ve launched about eight interconnected businesses.

Jasper:
That’s a lot. And you have three kids. How do you balance everything?

Troy:
I have an incredible wife and team. I love working, and my hobbies are my businesses and my family. My teams understand the vision and want to grow with me.

Jasper:
Hiring and team building are major challenges. What’s been your biggest learning there?

Troy:
Clear communication and setting expectations. It’s easy to hand someone a job, but if they don’t understand it, things fall apart. Also, just being a decent human helps, being approachable and listening to your team.

Jasper:
You’re one of our fastest-growing clients. What’s your acquisition strategy?

Troy:
Reputation and SEO helped early on. We invested in Google presence and got a lot of organic and referral leads. Then we partnered with Vintory for targeted marketing, emails, calls, postcards. But the key is delivering high quality. Owners know what we stand for.

Jasper:
If you had to start over, what would you do differently?

Troy:
I might not change much, but I’m glad I found Legends X early. Otherwise, I would’ve burned out. Systems saved my business.

Jasper:
For new STR operators, what advice would you share?

Troy:
Hire the right people for the right roles. Don’t just hire to ease overwhelm. Define the position clearly. It took some trial and error, but now we have a great culture.

Jasper:
How do you maintain high review scores at scale?

Troy:
We brought cleaning in-house to control quality. One bad clean can wreck a review. We hired a head of guest experience who oversees everything from listings to pre-arrival info to post-stay follow-up. One unique thing we do is call every guest two to three weeks before check-in. Just to say thanks, learn why they’re visiting, and offer help. People love it.

Jasper:
That’s amazing. Any guests who didn’t like being contacted?

Troy:
A few don’t answer or give short replies. But even then, we leave a nice voicemail or follow up with a text. The gesture means a lot. It only takes a few hours a week.

Jasper:
Any other guest experience tips?

Troy:
We’re working on more in-unit and out-of-unit experiences. Partnering with local businesses to offer curated activities. It also helps us promote our other ventures.

Jasper:
How can people connect with you or book a stay?

Troy:
Visit elevatedstays.com for Elevated Homes and Hospitality. For all my other ventures and real estate work, go to adventuretraversecity.com. If you’re in Traverse City, reach out. Let’s grab a coffee or a beer.

Jasper:
Thanks for joining us, Troy. I love working with you and appreciate everything you’re building. Looking forward to seeing you at IMN and watching your next phase of growth.

Troy:
Thanks, Jasper. I appreciate you and the whole team. Looking forward to what’s next.

Jasper:
Thanks for listening to Get Paid For Your Pad. See you next time.