The Boostly Podcast: "Turning Stays into Stories: A Host’s Journey to Creating Memories"

Release Date: October 7, 2024

In this enlightening episode of The Boostly Podcast, host Liam Carolan welcomes Andy Cheetham, the owner and managing director of The Terrace Windermere, a unique collection of large Victorian holiday properties in the picturesque Lake District. Andy shares his inspiring journey from a successful advertising career to building a thriving holiday let business, emphasizing the transformative power of direct bookings and the importance of leveraging technology and community support.

1. Introduction to Andy Cheetham and The Terrace Windermere

Liam introduces Andy Cheetham, highlighting the exceptional nature of The Terrace Windermere, which comprises six large Victorian houses designed to accommodate substantial groups. Andy explains the uniqueness of owning an entire private street, allowing full control over guest experiences and property management.

Andy Cheetham [03:24]: "We have six large houses, one small house which just happened to come as with a large house. The Terrace itself consists of five pretty large Victorian properties, listed buildings..."

2. From Advertising to Holiday Lets: Andy’s Business Journey

Andy recounts his transition from founding a successful advertising agency in 1993 to venturing into the holiday rental market in 2006. Faced with lucrative opportunities in the property boom and motivated by a strategic shift away from advertising post-IPO by WPP, Andy embraced real estate as a sustainable and profitable alternative.

Andy Cheetham [09:13]: "I was a founder and owner of quite a large advertising agency... I started the holiday net business actually by mistake a little bit... I thought, I need something else."

3. Navigating Economic Challenges and Building Resilience

The financial crash posed significant challenges, including negative equity and mounting debts. Despite these hurdles, Andy persevered, expanding his portfolio to nine properties. His resilience was further tested during the COVID-19 lockdown, prompting him to reevaluate and pivot his business strategies towards direct bookings.

Andy Cheetham [13:50]: "I had a big mountain bike crash in Canada and smashed my hip... It was time to just address the business."

4. Embracing Direct Bookings: A Strategic Pivot

Frustrated with the increasing automation and depersonalization of OTAs (Online Travel Agencies), Andy sought to regain control over his bookings. Inspired by The Boostly Podcast, he implemented direct booking strategies, resulting in a significant increase in revenue and a loyal customer base.

Andy Cheetham [26:34]: "I found that it's time I looked at my strategy and moved forward from there."

Liam Carolan [56:31]: "A moment in my life. When I started listening to more podcasts was when I saw a definite increase in quality of the business..."

5. Building an Effective Tech Stack for Efficiency

Andy emphasizes the importance of leveraging technology to streamline operations. Central to his tech stack is Super Control, a property management system that integrates seamlessly with his Boostly-built websites. Additionally, he utilizes tools like Inspire Heating Systems and Money Penny Telephone Answering to enhance guest experiences and operational efficiency.

Andy Cheetham [37:38]: "My tech stack really, it's got super control at the center of it, which is the PMS... and then out of that, really second to that or in tandem with that comes the Boostly websites."

6. The Power of a Dedicated Team and Exceptional Service

Andy attributes much of his success to his dedicated team. With 14 housekeepers and two maintenance staff, he ensures that every property remains pristine and guest experiences are exceptional. He underscores the value of treating team members well, fostering a sense of ownership and pride in their roles.

Andy Cheetham [46:01]: "We've got a really good housekeeping team. ... They're the driving force of your business."

7. Key Tactics for Growing Direct Bookings

Andy shares actionable strategies that have propelled his business forward:

• Focus on Sales: Prioritize driving more sales rather than merely cutting costs. Increasing revenue streams directly impacts business growth.

  Andy Cheetham [48:06]: "Sales solve everything... if you can drive more sales then you're going to have more success."

• Leverage Community and Resources: Utilize platforms like The Boostly Podcast and engage with supportive communities to gain insights and stay updated on industry trends.

• Invest in Technology: Implement integrated systems that automate and streamline operations, allowing for more direct interactions with guests and better data management.

8. Inspirational Insights and Personal Growth

Andy reflects on his personal growth and the satisfaction derived from creating memorable experiences for guests. He highlights the importance of resilience, continuous learning, and maintaining an optimistic outlook.

Andy Cheetham [50:51]: "Givers get lucky. If you can give more than you take, if you can help people, if you can give just some thanks... you're going to actually eventually receive more."

9. Conclusion and Takeaways

The episode concludes with Andy expressing deep gratitude towards The Boostly Podcast and its team for providing the tools and confidence necessary to transform his business. He encourages fellow hosts to focus on sales, invest in the right technology, and cultivate a dedicated team to achieve success in the competitive holiday rental market.

Andy Cheetham [54:14]: "Boostly is more than a website building company, it's more than a community. It's more of a transformation business..."

Key Quotes with Timestamps

• Andy Cheetham [03:24]: "We have six large houses, one small house which just happened to come as with a large house..."

• Andy Cheetham [09:13]: "I was a founder and owner of quite a large advertising agency..."

• Andy Cheetham [26:34]: "I found that it's time I looked at my strategy and moved forward from there."

• Andy Cheetham [37:38]: "My tech stack really, it's got super control at the center of it, which is the PMS..."

• Andy Cheetham [48:06]: "Sales solve everything... if you can drive more sales then you're going to have more success."

• Andy Cheetham [50:51]: "Givers get lucky. If you can give more than you take..."

• Andy Cheetham [54:14]: "Boostly is more than a website building company, it's more than a community..."

Final Thoughts

Andy Cheetham’s journey is a testament to the power of adaptability, strategic planning, and community support in overcoming business challenges. His success with The Terrace Windermere showcases how leveraging direct bookings and investing in the right technology can transform a business, providing stability and growth in an ever-evolving market. Hosts and aspiring entrepreneurs alike can draw valuable lessons from Andy’s experiences, emphasizing the importance of resilience, continuous learning, and a customer-centric approach.

For more insights and strategies on boosting direct bookings, listeners are encouraged to explore The Boostly Podcast and join the thriving hospitality community.

Connect with Andy Cheetham:

• Website: terracewindermere.co.uk
• Website: rsheadhouse.co.uk

Join the Boostly Community:

• YouTube Channel: boostly.co.uk/youtube
• Facebook Community: Hospitality Community

Recommended Reading:

• "Direct Booking Playbook" by Mark Simpson – Available on Amazon and major bookstores.