In just a few short years, Curious Retreats has become one of Suffolk’s most distinctive names in the luxury holiday rental space, combining the charm of handpicked properties with a genuine passion for hospitality. Founded by Tim Ripman and Tim Cook, the company has built a reputation for delivering exceptional guest experiences while championing local communities and sustainable practices.
In this exclusive conversation, Louis Mason from Oportfolio Mortgages sat down with the two Tims to uncover the story behind Curious Retreats, from their very different professional beginnings to the shared values that have shaped their growing brand. They talk candidly about the realities of running a hospitality business, the thrill of seeing every new booking come in, the lessons learned along the way, and the balance between passion and practicality that keeps them moving forward.
It’s a conversation filled with warmth, humour, and honesty. A reminder that success isn’t solely measured in numbers, but also in the joy of creating experiences that last long after the guests have gone home.
A Passion For Curious Retreats
Louis: So Tim and Tim, how did the idea of Curious Retreats come about?
Tim R: That’s a good question to start with. First of all, Tim and I go back 30 years. We have very different work backgrounds. Mine is in hospitality, and Tim’s was in the City of London financial markets, but we’ve been extremely good friends for such a long time. Over the years, at many dinner parties, nights out, stag dos, you name it, we’ve compared notes on what’s going on in each other’s work lives.
I think it was at a dinner party at my house, maybe four or five years ago, that the idea started to form. I mentioned that Best of Suffolk, where I was working at the time, was about to be sold to a big national player. Tim had just been part of a sell-out of a start-up in the City. We saw a potential opportunity for a local holiday home agency in our home county of Suffolk.
That’s when we put our collective experience and strengths on the table. Being very good friends, we also had complementary skills, and different weaknesses, which actually works well. With my eight years of experience in the industry, we saw an opportunity, not yet called Curious Retreats, for a quality-led, high-end holiday home agency in Suffolk that could compete with the big national players.
After many planning sessions in a spare bedroom of Tim’s, with whiteboards and brainstorming, we launched in August 2023. And here we are, two years down the line.
Louis: That’s great. I think everyone has those conversations with their best mates about starting a business together, but actually going for it, that must be scary. Was it, or did it feel natural since you were good friends?
Tim C: Well, for both of us, it felt quite natural. I’ve come from small start-up companies, so I had some comfort with taking a step like this. Of course, there’s always the financial responsibility, but with Tim’s experience in the industry, it felt like a logical move. From my perspective, it didn’t feel too scary.
The big risk, of course, is stepping out of a comfort zone and putting up financial commitment. The safety net of a corporate job is gone. But the upside isn’t just financial, it’s emotional and life-changing.
We recognised that doing this with someone we’ve known for decades meant we already understood each other’s work ethic, aptitude, and skills. That gave a lot of comfort. Going in 50-50 and fully committed, we knew our chances of success were much higher.
Louis: You’ve already touched a bit on your past experiences. How specifically would you say that each of your experiences has influenced the way you approach the hospitality and property industry?
Tim R: My background is hospitality through and through. After university, I worked in boutique and five-star hotels in Nottingham and London, mainly in front-of-house and service departments. I’ve always been operational, 24/7, and I absolutely loved it.
I remember being a young professional in London, watching some friends, including Tim, go off and earn good money in the City, while I was putting in ridiculously long hours. But I loved it. There are perks to this industry, as well as the blood, sweat, and tears. You can see the connection to what we do now, while we’re not literally 24/7, we do accommodate guests overnight, seven days a week, 52 weeks a year. There’s a real duty of care. So that’s what I bring to the table, along with eight years at Best of Suffolk before Curious Retreats.
Tim C: As Tim said, my background is completely different, but in terms of personality and skills, I bring traits that complement what we do, along with financial expertise. Interestingly, there are more similarities with hospitality than you might expect.
Financial markets involve a very high level of customer care and service because you’re dealing with clients who can be extremely demanding. In hospitality, it’s similar, guests often pay a premium and have high expectations. You really have to understand how to manage client relationships and expectations.
We also conduct regular performance reviews with property owners, much like I did in finance with banks about the performance of training technology. We look at the data, highlight areas for improvement, identify opportunities for more upside, or recommend reducing certain things. Those “awkward conversations” feel very similar to the finance world, even though they seem completely unrelated at first.
Louis: That’s really interesting. As someone not in the industry, I wouldn’t have considered that side of things.
Tim R: Exactly. On the strengths and weaknesses side, I’m motivated by front-of-house work, guest experience, and problem-solving. My weakness is data analysis and, to some extent, technology, areas that Tim brings to the table.
What’s In A Name?
The two Tims are based in Suffolk, but have big ambitions
Louis: The name Curious Retreats is really evocative. How did you land on that name?
Tim R: One of the highlights of our first foray into Curious Retreats was the branding exercise. We were recommended a company based in Tunbridge Wells that specialises in branding, PR, and marketing. They suggested we spend some time with them, so we went up for a day-and-night visit.
We were essentially locked in a room with a creative team, answering lots of questions, not just about the company, but about our values, our purpose, and the core beliefs that drive us. From that, a few ideas started to emerge.
In Suffolk, many agencies have the location in their name, like Suffolk Retreats or Eastern Retreats. We didn’t want to limit ourselves geographically because we have bold ambitions. We wanted a name that could grow with us.
Curious was one of the words we had considered before going to Tunbridge Wells, and it came back as one of the options. It felt right. It evokes exploration and interest, something that makes people want to learn more and experience more, which reflects what we want guests to feel when they come to Suffolk.
Tim C: There was also a fun moment when we shared some of the designs with our wives. Tim’s wife, Jules, noticed that the initials C and R weren’t just Curious Retreats, they also represented Cook and Ripman. It was a happy coincidence that made the name feel even more personal.
Tim R: And even though Suffolk is central to our brand, we didn’t want to be limited by it. We’re Curious Retreats, not Curious Suffolk. That gives us flexibility to expand anywhere in the future.
Suffolk, Where It All Began…
Both Tim C and Tim R grew up in Woodbridge, Suffolk
Louis: Speaking of Suffolk, why was it the right location for you?
Tim C: It’s our comfort zone. We were both born and bred here, though we’ve lived and worked elsewhere for periods. We have great contacts, a strong portfolio of second homes, and access to all the tradespeople and services needed to maintain high standards, housekeepers, gardeners, electricians, plumbers, you name it. Woodbridge is our base, but we cover the county.
Tim R: That said, we’ve had interest from places like Cambridge and Norfolk, but our approach is one step at a time. We want to do what we do in Suffolk really, really well first.
We know the region intimately, which helps us offer a unique guest experience, from concierge services and private chefs to golf courses and local attractions. Our lived experience gives us an edge that research alone can’t provide.
Tim C: Exactly. If we expand to other regions, we’ll need people with that local knowledge. Doing it well in one area gives us a benchmark for growth.
Louis: That makes a lot of sense. It will clearly set you apart from companies that don’t know the area and just claim to.
Tim R: Yes. Suffolk has a lot to offer visitors, from domestic tourists to those coming from further afield. It’s still undersold as a staycation destination, despite its proximity to London and the Midlands. We want people to come, stay, and enjoy it, maybe for a long weekend or even a full week, and want to come back.
Tim C: For example, getting from Southwest London to Woodbridge is really easy. For Londoners, a weekend trip is convenient, either by car via the A12 or by train. Once you’re here, in many of our properties, you don’t even need a car to enjoy the area.
Louis: The site mentions that all the properties offer something different, something special, something curious. What standards or criteria do you use when selecting a property for your portfolio?
Tim R: There’s a huge amount of variety. Going back to Curious, we don’t define ourselves as luxury, boutique, or contemporary because we handpick properties that fit our ethos. It’s about balancing quantity and quality so we can manage a portfolio where guests consistently get a five-star-plus experience.
Our properties vary in size, location, and style, but the owners are a key part of the process. We’ve tried to surround ourselves with people who want to be part of the journey, part of the family. While we act as their agent and market their property, owners have the final say on what happens.
Tim C: For us, it’s about whether a property can deliver an experience where guests enjoy themselves. Ideally, they give us a five-star review, come back, or spread the word to their friends and family. Word-of-mouth has been critical to our growth, and we hope it continues.
Tim R: It’s not just about having mod cons or luxury amenities. Some guests want off-grid experiences, like shepherd’s huts or quiet retreats to disconnect. We aim to have a balanced portfolio: properties for large family gatherings, as well as places for individuals to relax, write, paint, or just unwind.
Tim C: When we evaluate a property, we ask ourselves: can we imagine ourselves here? Would we be happy coming here with our families? If a property meets those high expectations and we’re working with the right owners, then it’s a fit.
Tim R: For example, we have a property called The Crow’s Nest on the River Deben. It’s a three-bedroom, three-bathroom home with terraces overlooking the river. Whether it’s high tide on a sunny day or a stormy winter afternoon, it’s a special place to be. It’s hard not to smile whenever you stay there.
A Curious Concierge Service
Tim and Tim traded their employed jobs to become their own bosses
Louis: Tell me more about the Curious Concierge service. That seems really popular and quite unique. What kind of requests do guests typically make?
Tim C: Curious Concierge is an extension of our guest experience. It’s about creating lasting memories and ensuring guests want to come back. There’s really no limit. Requests range from private dining experiences for 14 people with a specific cuisine, to balloons for birthday celebrations. We have a network of trusted vendors and chefs to facilitate these experiences.
Tim R: It can also be lighter touches, like recommending walking routes, dog-friendly beaches, or places to hire electric bikes. Concierge is flexible, it can be as hands-on as the guest wants, or just guidance and advice.
Tim C: We feel a responsibility to showcase what makes Suffolk great. We have a network of local producers, salmon in Orford, mussels in Maldon, chocolate shops, microbreweries, vineyards, and we help guests connect with them. If guests enjoy these experiences, they’ll tell their friends and come back themselves.
Tim R: A recent example: a guest here on an extended stay requested dog-walking and supervision for her daughter’s dog. It’s a dog-friendly property, but we needed to ensure someone could take care of the dog while they were out. It’s a small but important detail that enhances the overall experience.
Louis: It sounds like you’re very committed to guests, even in the smaller details.
Tim C: Absolutely. Suffolk is a very dog-friendly county, and we are a dog-friendly business. While I don’t personally own a dog, we’re all fans. We’ve had other more unusual requests from guests, but we work with property owners to accommodate these cases safely.
Tim R: Our goal is to provide an exceptional, personalised experience, no matter how unusual the request.
What The Future Holds For Curious Retreats
Suffolk is a hotspot for staycations in England
Louis: What are your short-term and medium-term goals with Curious Retreats over the next one, three, and five years?
Tim R: We’ve broken it down mainly around business growth. We recently hit a milestone of managing over 50 properties, which is really exciting. Tim mentioned earlier that much of this growth has come through word of mouth.
Looking ahead, we feel comfortable aiming for 100 properties under management with the resources we currently have. Beyond that, say 150 to 250 properties, we’d need to consider recruitment and expansion to maintain service levels. The biggest challenge is scaling without compromising the consistency and quality of the guest experience we currently provide.
Tim C: Exactly. It’s about maintaining what we’ve achieved to date. We’re ambitious and want to grow, but not at the expense of the experience we’ve worked hard to build. Sometimes that means politely declining opportunities that aren’t the right fit.
Louis: You’ve achieved a lot in just a couple of years. What has been the biggest challenge as a fairly new business? Any surprises along the way?
Tim R: Competition has been a major challenge. While there aren’t huge numbers of competitors, the ones that exist often have extremely deep marketing budgets. They are parts of large organisations, often based in the City, spending millions on marketing.
The challenge for us is visibility. Word-of-mouth has been great, but many property owners don’t even know we exist. We’ve had to be strategic with a limited budget, using third-party experts when needed, to make sure we appear in the right places online and attract prospective clients.
Tim C: We’ve done everything on a relative budget. What we’ve never compromised is guest experience and service levels. We’re fully self-funded and haven’t taken external investment. While we could raise funds to expand marketing, we’d then be accountable to investors who may not share our values or vision. Staying independent allows us to focus on building the company according to our ambitions and values.
Tim R: The period from 50 to 100 properties will be about momentum. Right now, it feels challenging, but in hindsight, we’ll see it as a necessary phase of building credibility and trust with property owners. Reviews, both from guests and owners, are essential in that process. They demonstrate the quality of our service and help prospective clients feel confident working with us.
Tim C: Reviews are massive for us. We integrate them from Airbnb, Google, and our website. Google reviews are especially valuable because of their reach. Every new five-star review is celebrated, it motivates the team and reinforces why we do what we do.
Tim R: At the end of the day, it’s about enjoyment and satisfaction. If bookings were coming in but we were constantly getting negative reviews, it would feel like a burden. Instead, we’re in a place where the business grows, guests are happy, and we get to enjoy the process.
Tim C: Managing Curious Retreats involves juggling multiple touchpoints, guests, property owners, housekeepers, tradespeople. As a small team, it keeps us on our toes, but personally, I love that. It’s dynamic, rewarding, and fulfilling.
Louis: You can really tell the passion you both have for everything you do. There really is nothing better than having job satisfaction.
Tim R: Absolutely. Job satisfaction is huge. I think back to my years in hospitality, never earning huge sums, but the enjoyment and pride in the work were what mattered. Likewise now, we want to make a huge success of Curious Retreats, but also have a damn good time.
Tim C: I spent 20 years in an industry focused on making money rather than job satisfaction. Towards the end, if you weren’t chasing the paycheck, there wasn’t much fun. I’ve seen friends completely change career paths because of that, and they’re much happier now. It really emphasizes how important enjoyment is in your work.
Taking Pride In What You Do
The scenic Suffolk coast is an ideal getaway
Louis: What has been your proudest moment or milestone in building Curious Retreats so far?
Tim R: Sitting here today and reflecting on everything we’ve achieved in just over two years. One personal highlight was when Tim joined full-time, he was already deeply involved but being operational day-to-day brought a new dynamic. Successfully navigating our third summer in 2025 was another, along with increased SEO performance and a 400% increase in Google reviews.
Tim C: For me, it was the first direct booking through the website. That slight endorphin hit, you know someone trusts us enough to part with their money, is something neither of us will ever get bored of.
Tim R: I also take pride in how the business looks from an operational and financial perspective. Even the spreadsheets show a fully functioning, sustainable business. We’ve always been thoughtful about where we spend money, making Curious Retreats viable and not just a vanity project.
Tim C: It’s also rewarding that people want to join the team. We’ve met candidates with impressive CVs who are excited to be part of Curious Retreats. It shows the business is appealing and has a strong foundation.
Louis: That must feel great.
Tim R: Absolutely. Even with all the bookings and tasks, there’s a rhythm to dividing and conquering. One of us might be office-based while the other is out meeting owners or networking. It allows us to maximize our time, and every day brings something different, owner meetings, guest requests, property viewings, or filming for social media.
Tim C: It’s diverse, dynamic, and keeps us on our toes. We don’t have a fully functional office like some businesses, so we’re often out with phones in hand, making it work despite network challenges.
Tim R: And importantly, even with the pace, we still get downtime, holidays, and family time. Curious Retreats runs smoothly while allowing us a balanced lifestyle. And we both still get to go on our own holidays!
Louis: Where did you go on holiday?
Tim C: I was in America to see my brother and then had a week in France.
Tim R: I went to Menorca with the family. We went the first week the children broke up, so there was still a lot of summer left. We also stayed in an Aldeburgh property for a big summer week covering the regatta and carnival. I also went up to Barnard Castle in County Durham because my son was playing cricket there for a week.
Work Life Integration
There are lots of property times to match your personal preference
Louis: It sounds like you both managed to get away while still working?
Tim R: Exactly. Tim and I could still work when needed, with evening catch-ups, but the flexibility to be “off-grid” for hours is quite nice.
Tim C: We don’t have a rigid separation between work and life. We work long hours, obviously, but we can take time for family, children’s sports, birthdays, or a round of golf. There’s no bureaucracy or sign-off process, it’s mutual trust.
Louis: That reminds me of what BrewDog’s James Watt calls work-life integration rather than balance.
Tim R: Yes, exactly. When you enjoy what you do, it’s embedded in you. Even on a Saturday afternoon, I might check the numbers or bookings, not because I have to, but because I’m curious. Unlike previous jobs, I don’t feel the need to completely switch off.
Louis: That’s fascinating. And looking at guests, how do you hope they feel when they stay at a Curious Retreats property?
Tim C: We hope guests feel that Curious Retreats is their “home away from home.” Many of our repeat guests return multiple times, some four, five times or more. That’s the kind of connection we want: long-term relationships, where guests feel valued and cared for.
Tim R: Guests get both a high-quality property and a personal touch. They know that if they need something, before, during, or after their stay, it’s frictionless. Most companies struggle with direct contact, but we actively encourage it via phone, WhatsApp, live chat, or email.
Tim C: Even something as simple as recognising the two Tims can be a fun experience. Guests can tell our voices apart, which creates familiarity. The personal connection is part of the Curious Retreats experience.
Green Footprint and Giving Back To The Community
Best friends turned business partners Tim Cook and Tim Ripman with their curious electric van
Louis: That’s brilliant. I suppose in this day and age, things like sustainability, re-investing in the community, and green business practices are things that a lot of guests are passionate about.
Tim R: Absolutely. One of the things that we, as business owners, are really focused on is our green footprint and giving back to the area. We try to leave Suffolk better than we found it. That means:
- Paperless operations wherever possible.
- Electric vehicles for the business.
- Planting a tree for every booking via Just One Tree, with clear carbon offset tracking.
Tim C: Beyond that, we support local events and charities. For example, next weekend we’re sponsoring the St Joseph’s Rugby Festival, a two-day event for schoolboy rugby. It’s about contributing to the community while also showcasing Curious Retreats in a meaningful way.
Louis: That’s fantastic. You’re combining business success, sustainability, and local community support.
Tim R: Exactly. If we can have fun along the way, watching rugby, hosting clients, playing golf, while also contributing to causes like Just One Tree, it all aligns with our mission.
Louis: Well, it’s been amazing hearing the journey of Curious Retreats from the very beginning to where you are now. Thank you so much for sharing all these stories, insights, and behind-the-scenes moments.
Tim R: Thanks, Louis. It’s been great to reflect on everything, we’ve covered a lot of ground, and it’s nice to see how far we’ve come in just a couple of years.
Tim C: Absolutely. And hopefully, people reading this can get a sense of what makes Curious Retreats special: the properties, the people, the experiences, and that personal touch that we care so much about.
Louis: I think you’ve absolutely conveyed that. It’s clear this is more than just a business, it’s a passion, a community, and an experience for everyone involved.
Tim R: That’s exactly what we hope people take away from it. We want guests to leave with a smile, owners to feel proud of the properties we manage, and the local community to see the positive impact we try to make.
Tim C: And for us personally, it’s about enjoying the journey, celebrating the wins, learning from the challenges, and continuing to grow, while staying true to the values that started it all.
Curious Retreats – Your Partner In Finding Your Dream Holiday Rental
From our conversation with Tim Cook and Tim Ripman of Curious Retreats, it’s clear that running a successful holiday rental business requires far more than simply renting out properties. True success comes from a deep passion for what you do and an intimate understanding of the area you operate in. With that combination, you can deliver exceptional guest experiences and give your region, along with its beautiful properties, the recognition it deserves.
A huge thank you to Curious Retreats for sharing their story with us. If you’re looking for your next Curious Retreat in the UK, you can get in touch with Tim and Tim here.
