#160: The Boutique STR Path to Profit Without Burnout — with Jessica Hill

Ever feel like scaling your STR biz means sacrificing your sanity?

Jessica Hill is living proof it doesn’t have to be that way.

In this episode, we chat with the inspiring mama, healthcare pro, and STR entrepreneur behind Jet Setter Property Management — where intentional design meets boutique profitability. With just 12 hand-picked properties, Jessica has built a wildly successful short-term rental business that’s rich in personality and profit… without managing dozens of doors or burning the candle at both ends.

She gets real about:

• Designing properties that connect emotionally (hello, custom murals and curated guest experiences)
• Balancing a demanding W-2, motherhood, and business ownership
• The systems, boundaries, and support that make her model sustainable

This convo is a masterclass in doing STRs differently — and doing them on your terms.

If you’re craving a business that feels good and does good, this episode will remind you that “more” isn’t the goal — meaning is.

HIGHLIGHTS AND KEY POINTS:

[00:56] A short introduction about our guest Jessica Hill and how she got into the world of short-term rentals

[03:32] Jessica talks about her company and explains why she intentionally operates a boutique, hands-on property management model instead of scaling into a large, volume-driven portfolio

[05:19] Jessica emphasizes the importance of intimate, hands-on management that boutique operators provide compared to large-scale property managers

[09:55] Jessica’s active involvement in the guest experience and daily operations despite having a team

[11:03] Jessica shares about her W-2 job and what she has pulled over from her W-2 into her short term rental business

[12:35] Jessica explains explains why strategic design is a performance lever, not just aesthetics, in driving bookings and brand demand

[16:11] Jessica talks about how she monetizes design and listing optimization as value-add services within her boutique hosting model

[17:31] Jessica shares the key foundations smaller hosts should prioritize to deliver a high-touch guest experience through a boutique-style approach

[20:11] How Jessica balances a full-time W2 career, motherhood to a special needs child, and her co-hosting business through intentional time management

[22:32] Jessica shares how motherhood shaped her communication philosophy in short-term rentals

[25:15] Jessica emphasizes the power of over-communicating with her team to build ownership and brand-aligned service

[27:27] Jessica shares her piece of advice for all women who are chasing big dreams while also navigating life, being a mom, working a full time job

[29:51] The lightning round

Golden Nuggets:

• “Start and make sure that you have the proper systems in place.”
• “I have brought those people on my team to help with those things, so that way I can be a more effective property manager and do the things that I love to do.”
• “When you love what you do, you never work a day in your life.”
• “Don't lose yourself in the day to day of motherhood. Carve out a little time for yourself,...