Ops, Bookkeeping, and Preventing Breakage

Connect with Sean:

Instagram: https://www.instagram.com/sean_bakhtiari/

Check out Seacoast 2 Summit: https://www.seacoast2summit.com

Check out our free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

What happens when a corporate finance guy from Boston decides he's done working for someone else — and bets on short-term rentals?

Sean Bakhtiari is the co-founder of Seacoast 2 Summit Vacation Rentals and The Bakhtiari Group, a top-performing real estate sales team across Massachusetts, New Hampshire, and Maine. As an active STR investor, his work sits at the intersection of real estate, hospitality, and investment strategy throughout New England.

After 9 years in Boston's financial district, Sean bought his first STR. Then a second. Then started building a management company.

At 12 properties, he hit a wall. He was good at business development and client relationships. But systems, operations, and scale? Not his strengths. That's when a serendipitous call from Chris changed everything.

Today, Sean and Chris co-run Seacoast to Summit Vacation Rentals — managing 120+ properties across the New Hampshire seacoast, lakes and mountains region, and North Shore of Massachusetts. Almost entirely on referrals, with virtually no paid marketing.

In this episode, Sean and Chris pull back the curtain on:

- How they identified each other as the right partner (and what 3 things you need to align on before you sign anything)

- Sean's "help first, never sell" philosophy — and why it's responsible for most of their growth

- Why they've said no to 10+ deals in the last 3 months (and why that's the right call)

- The two fears they stay up at night thinking about as they scale

- How to delegate without feeling like you're losing control

- What it takes to keep your team culture intact as you grow

- Why boutique hotels might be the next frontier for this business

This is a rare episode — a founder bringing on his business partner and pulling off the veil on how a real, values-driven STR company actually works at scale.

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Timestamps:

0:00 - Introducing Sean Bakhtiari: Chris's Business Partner

2:45 - How Sean Went From Corporate Finance to STR Management

6:30 - Building Seacoast to Summit: From 12 to 120 Properties

10:15 - How Sean and Chris Found Each Other (The Serendipitous Call)

15:00 - The 3 Things You Must Align On Before Partnering

18:30 - The "Help First" Sales Mindset That Built the Business

23:00 - Why They Said No to 10 Deals in 3 Months

27:00 - The Two Fears They Have About Growing Too Fast

32:30 - How to Delegate Without Losing Control

37:00 - Keeping Team Culture Intact at Scale

42:00 - What the Future Looks Like: Boutique Hotels and Brand Building

46:00 - Sean's #1 Secret to STR Success