Now Enrolling: The Second Home First Academy

Two wooden lounge chairs on a tile poolside patio near a swimming pool.

A five-week, guided, community-based program for people who want more income, optionality, and freedom in their lives.

Enroll Now

What You'll Learn

In just five weeks, you’ll develop the knowledge, tools, and confidence to buy a vacation home that pays for itself — alongside a small group committed to doing the same.

A large wooden house with a stone foundation surrounded by tall pine trees in a mountainous area, with a paved driveway leading up to it and a blue vehicle parked nearby.

Week 01

Step 1: Dream It

Week one is all about envisioning your perfect vacation home and turning that into a clear, actionable plan. Through a combination of brainstorming exercises, worksheets, quizzes, and checklists, you’ll refine your vision, set priorities and lay the foundation to turn your dream into reality.

Live Community Call:

April 8, 6:00–7:30pm ET (90 minutes)

Residential houses by a water body with docks, balconies, and outdoor furniture, under a clear blue sky.

Week 02

Step 2: Plan It

Week two establishes the financial foundation of your vacation home search. Worksheets, calculators, and checklists equip you to navigate budgeting and financing with ease. Empowered with this knowledge, you’ll be ready to confidently purchase your dream vacation home.

Live Community Call:

April 15, 6:00–7:00pm ET (60 minutes)

A tropical beachfront with a thatched roof building on stilts, surrounded by palm trees, with a sandy shore, clear turquoise water, and a cloudy sky in the background.

Week 03

Step 3: Prep It

Week three focuses on preparing your vacation home to host both you and your family, as well as your paying guests. Helpful tools, worksheets and checklists make it easy to define your ideal guest, design your dream space and seamlessly welcome your first visitor. Pro tips ensure the property runs smoothly, making it a place you'll love to escape to and a home guests will never want to leave.

Live Community Call:

April 22, 6:00–7:00pm ET (60 minutes)

A backyard with a swimming pool, two lounge chairs, trees, and a brick wall.

Week 04

Step 4: Live It

Week four zooms in on the practicalities of managing your vacation home. This week includes quizzes, checklists and expert advice to help you select the best management option for your needs. It also highlights strategies for future-proofing your investment so you can enjoy a sustainable vacation home for years to come.

Live Community Call:

April 29, 6:00–7:00pm ET (60 minutes)

Modern living room with large glass windows, a wood-burning stove, a gray sofa, a black coffee table, a dining table with white chairs, and a view of a wooded yard outside.

Week 05

Your Roadmap

Week five brings everything together into a cohesive, personalized roadmap. Through guided exercises, strategic prompts, and practical checklists, you’ll define your budget confirm your financing path, clarify your timeline, and identify potential blind spots. By the end of the course, you’ll have a clear, actionable plan tailored to your specific goals, giving you the confidence to move forward and turn your vision into reality.

Live Community Call:

May 6, 6:00–7:00pm ET (60 minutes)

Enroll Now - Spots are Limited

Meet Your Instructor:
Katie Cline

A woman with blonde hair wearing a beige wide-brimmed hat, blue blazer, and gold chain necklace, sitting outdoors with green and purple foliage in the background.

Katie Cline is an award-winning publicist, hospitality veteran & short-term rental expert. She's the host of two podcasts: Second Home First and Suite Success (now part of Skift)— and the creator of the free weekly newsletter at BuyYourSecondHomeFirst.com, where she helps readers turn their dream of owning a vacation home into a practical wealth-building strategy.

Katie led global communications for iconic hotel brands, including The Ritz-Carlton, St. Regis, and W Hotels in both New York and London. Today, she brings those five-star insights to her own portfolio of vacation homes in upstate New York: Trout Landing(near Lake George), Gallant Fox (in Saratoga Springs), and The Lazy Oar (on Seneca Lake). An obsessive traveler and dual citizen of the U.S. and Ireland, Katie can typically be found trying a new restaurant in Astoria (NYC) with her husband; schooling her British-born toddler on the magnificence of New York bagels; or researching her next investment property while snuggling her infant son.

Katie’s Vacation Homes

  • A two-story house with a steep gable roof and black trim, surrounded by trees, with warm lights on inside. In front of the house, there is a backyard patio with a fire pit and several chairs, where two people are sitting and conversing amid string lights overhead at dusk.

    Trout Landing

    BOLTON LANDING, NY

    Trout Landing is a four-bedroom, three-bathroom pet friendly chalet, set on 6+ serene, wooded acres just minutes from Lake George.

  • Living room with green sofa, plaid pillows, and a dining area with wooden table and tan chairs, picture window, black and white wall art, black starburst chandelier, arched doorway, hardwood floors, and light-colored walls.

    Gallant Fox

    SARATOGA SPRINGS, NY

    Gallant Fox is a four-bedroom, two-bathroom pet friendly home located in the heart of Saratoga Springs, walking distance to beloved local attractions such as Broadway, Beekman and the race track.

  • A wooden outdoor dining table with six chairs on a deck overlooking a body of water, surrounded by trees.

    The Lazy Oar

    LODI, NY

    Drive through a vineyard to reach The Lazy Oar, a two-bedroom, one-bathroom waterfront home perched on a cliff above Seneca Lake. Stroll down to your personal lakeside oasis to enjoy 50’ of lake frontage.

Frequently Asked Questions

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Enroll Today

  • For people who want more income, optionality, and freedom in their lives.

  • In just five weeks, you’ll develop the knowledge, tools, and confidence to buy a vacation home that pays for itself — alongside a small group committed to doing the same.

  • SHF Academy is a five-week, community-based program designed to guide you step-by-step through buying and launching your own second home first.

    Inside the Academy, you’ll receive:

    • Five live weekly sessions (30 minutes of focused teaching + 30 minutes of live Q&A)

    • On-demand lessons to deepen your understanding between sessions, completed on your own timeline

    • Worksheets, quizzes, calculators, and checklists to turn ideas into action

    • Proven frameworks to help you define your vision, confirm your budget, identify your target market, map your financing path, and select the right management model

    • Expert guidance on designing a home you’ll love — and guests will love to book

    • Real-world insights from my three vacation homes, including lessons learned and mistakes avoided

    • Access to session replays so you can revisit key lessons

    • A personalized roadmap that brings everything together into a clear, actionable plan

    By the end of the program, you won’t just have inspiration — you’ll have clarity, strategy, and a defined path forward so you can buy a vacation home that pays for itself.

  • SHF Academy’s inaugural class begins April 8, 2026. Enrollment is intentionally limited to ensure a high-touch experience and will close on April 7 at 8:00 PM ET, or once capacity is reached. Live sessions for the inaugural class will take place every Wednesday at 6:00pm ET, though all sessions will be recorded if you cannot attend. The last session will take place on May 6.

  • Enter your email address below to join the waitlist to receive priority access — plus a special launch discount available only to subscribers.

  • Feel free to email me directly at Hello@BuyYourSecondHomeFirst.com with any questions or concerns you may have. I look forward to connecting!

  • Spots are intentionally limited for the inaugural class, so enroll now.

    https://secondhomefirst.thrivecart.com/second-home-first-academy/