travel entrepreneur

"Don’t shy away from challenges and obstacles within your business" with Julie Singh

Julie Singh

Julie Singh founded with her husband Reet out of a shared enthusiasm for outdoor adventure and travel.  After many frustrating experiences wasting valuable vacation time renting equipment, they created a website where outdoor enthusiasts save time and effort by easily booking outdoor adventures and gear online.  Julie spent 15 years in retail, finance, and technology at a fortune 30 company and left her corporate career in 2017 to pursue her passions and build  TripOutside is a fully mobile company – they gather information on the best outdoor destinations for their customers by exploring the country in their motorhome with their cat Juke.

Can you tell our readers about your background?

After graduating with a finance degree and getting my CPA, I spent 15 years in Corporate America working first for food & beverage companies in Finance and Internal Audit and then spending 10 years in Finance and Merchandising at Home Depot Corporate.  My last role was running a $1B business as the buyer for Water Heaters for all 2000 stores.  Through these roles, I gained a ton of valuable knowledge and experience that has provided a great foundation for me to start my business.

What inspired you to start your business?

The idea for TripOutside came about on one of our vacations.  My husband and I traveled a lot in our free time, and spent as much time outdoors as we could.  We rented gear like bikes, kayaks, and skis during our adventures and saw a problem to be solved with online gear rental.  We wasted too much of our vacation time renting equipment!  The typical process involves online searches, calling shops about availability, booking over the phone, and waiting for bikes, skis or kayaks to be prepared in-store.  So, we created, a website that allows outdoor enthusiasts to compare prices and book gear and experiences on one website at the top-rated shops in key outdoor destinations.  The gear will be waiting at the outfitter, getting customers to their adventure faster!

We also wanted to be able to travel more, work from anywhere, and focus more on our passions of travel and outdoor adventure.  Starting TripOutside allowed us to do these things, and help get more people outdoors!

Where is your business based?

TripOutside is a fully mobile company, and we are based wherever we are traveling.  We are traveling in our motorhome in the Sierra range of California.  It works out really well, because as we hit the top outdoor destinations to bike, paddle or ski, we also visit the best shops in the area to get them featured on

How did you start your business? What were the first steps you took?

The first steps we took was to do a ton of research on what types of websites already existed.  We wanted to arm ourselves with as much knowledge about the industry as we could, and make sure that our site would provide the best experience possible and solve a true problem for our customers.  We started designing mockups of how we would like our website to work, and the features and functionality that we thought would be important.  We brainstormed names during a car ride to the mountains and came up with TripOutside.  The domain was available, and we bought it!  Then we created an LLC using Legal Zoom, which made it easy for first-timers like us to start a company. 

What has been the most effective way of raising awareness for your business?

Because we are a marketplace, we work to raise awareness with both outfitters and customers!  Initially, this was our biggest challenge – especially the first couple of outfitters!  Therefore, traveling to these locations and visiting outfitters in person was important.  Once we gained traction, it became easier and now we have outfitters finding us through google, social media and word of mouth!  On the customer side, we are still working on building awareness through a variety of avenues like SEO, paid, affiliates, influencers and more. Raising awareness is always a work in progress for us, and we are constantly testing different ways of getting the word out!

What have been your biggest challenges and how did you overcome them?

We have been working with a lot of contractors on things like website development, marketing, research, etc. and hire from websites like Upwork frequently.  We had challenges with some of our initial contractors not meeting our expectations and not work on time or to plan.  We constantly looked for new contractors.  It was a learning process–we learned not to hire solely based on their profile and reviews because they can be misleading. 

First, we now only target contractors with 99% or 100% job success–even 1 bad review can mean they may not be a good fit for us.  Second, we give each potential candidate for a small project first to see how they do.  Based on their quality of work, communication, adherence to deadlines, etc. we then hire for a larger project.  Third–and this one is important–we try not to hire someone to work that we don’t fully understand.  We have learned that we have to build at least a basic level of understanding of all aspects of our business to guide others on what we want.  Online training sites like Udemy and have great resources for everything from Marketing to Finance to Operations, and help you learn the key points so you don’t have to rely on a contractor to handle the strategy for parts of YOUR business.  We also subscribe to various industry leaders for things like SEO so we can communicate goals and understand exactly what our contractors are doing to accomplish them.

How do you stay focused?

It can be hard, especially when we are in incredible outdoor destinations!  The good thing is that it allows us to get out and experience the destinations we are featuring for our customers.  We try to get outside and explore for most days and then focus the rest of the day working.  We are passionate about helping get others outdoors, and we enjoy work–so that definitely helps.  If we work 24/7 (which definitely happens when you start your own business!), we try to step away and get out into nature to help us clear our heads, maintain our positivity and even get the creative juices flowing!

How do you differentiate your business from the competition?

TripOutside is the only website that allows outdoor enthusiasts to find top outdoor destinations, compare the pricing of the top shops and book bikes, kayaks, paddle boards, rafts, skis and more online.  Our key differentiation is that we focus primarily on the outdoor customer who wants to build their own outdoor adventure–either DIY or guided.  Many other travel sites exist where customers can book a broad variety of experiences–everything from museum visits to guided city tours.  We have a smaller niche, but everything on our site applies to the outdoor enthusiast.

Tahoe SUP_Julie.jpg

 What’s your best piece of advice for aspiring and new entrepreneurs?

The obstacle is the way.  Don’t shy away from challenges and obstacles within your business – this is probably why you started the business, to begin with!  The challenges are usually where the big “aha!” moments come from, and where you can make the most difference.  It will not always be easy, but that’s also why it probably hasn’t been done before.  Have confidence in yourself and your ability to figure it out!

What’s your favorite app, blog, and book? Why?

We love the books Essentialism and the Power of Now – they are not business specific but have provided great guidance and insight that applies to many aspects of our lives.

What’s your favorite business tool or resource? Why?

Some of our favorite business tools are Canva, which allows us to create Marketing content, and Buffer, which helps us manage our social media. 

Who is your business role model? Why?

I’m inspired by Arianna Huffington and her hard work on the Huffington Post, which is one of my favorite news outlets.  She’s not afraid to put herself out there and to change her mind about her views.

What do you have planned for the next six months?

We are focused on adding new outfitters in key destinations every day and expanding internationally.  We are building great tools for both customers and outfitters–like pricing comparisons, trip guides, brand demo days features, and user-generated content. 

How can our readers connect with you?


IG:  @trip.outside

FB:  tripoutside

Q&A with Entrepreneur Valeria Duflot

Photo Credit: Sebastian Fagarazzi / Venezia Autentica

Photo Credit: Sebastian Fagarazzi / Venezia Autentica

Valeria Duflot is the co-founder and startup CEO of the social business Venezia Autentica. She is a believer in the digital world, tech,  innovation, social justice, and sustainability. Valeria holds degrees in Health & Biology and Business Administration and is a neuro and mental health advocate.

Can you tell our readers about your background? 

I'm a 30 year old well-traveled Frenchy with a serious need to try to make things around me better. I'm convinced that business can and should be used to make a positive impact on our world.

Before Venezia Autentica I co-started and co-run a business focused on giving a platform to creative entrepreneurs, worked as a consultant in the healthcare industry and  (co)-organised and curated numerous events and festivals in the field of tech, innovation, performance arts, and entrepreneurship.

I also started researching and developing a couple of businesses ideas that I later paused, one because I realized that it wouldn't work, at least not the way I wanted to go about it,  the other one when I had the idea of Venezia Autentica. 

I hold degrees in Health and Biology and Business Administration and have been living abroad more or less continuously since 2011.

My current venture, Venezia Autentica, is a social business I've co-founded to halt the exodus of the Venetians who are pushed out off their city by unregulated mass tourism. We are trying to do so by making it easy for visitors to feel like locals in Venice while making a positive impact on the life of the Venetians.

What inspired you to start your business? 

I had a 'Eureka ' moment after living in Venice for a few months with my boyfriend, and co-founder Sebastian, who is a native Venetian. 

Due to our interactions and the ones with the people around us,  I was aware of the struggles Venetians face to stay in their city as well as the 'theme-parkisation' of Venice. 

One day, when having a walk, I found myself in between a huge guided group of day trippers and a bunch of young Venetians men who were singing local songs and harboring the Venetian flag. 

I knew the impact that day tourism had on the city and remembered that when my friend and I first visited Venice, we had a completely different approach and that we really enjoyed taking our time and spending time with local artisans who shared their world with us. 

Thinking about this, it suddenly hit me,  I realized that my friend and I couldn't have been the only tourists looking forward to meeting locals, and to support authentic businesses. I thought to myself that if a part of the 30 million tourists coming to Venice yearly would spend their time and money in the right places, and especially at the local businesses then it could have a huge impact on the 55,000 Venetian residents future and the city itself. 

No one was doing anything really to help the Venetians, so I decided that if I could convince Seba to come on board, we would do it ourselves.

Where is your business based?

We're based in Venice, Italy but being a digital company, we are accessible everywhere in the world.

How did you start your business? What were the first steps you took?

The first thing I had to do was to convince my partner in life to work with me on this project as I couldn't see it making any sense without someone who knew the problem from the Venetian perspective in and out. Moreover, as Sebastian and his family used to run a local business in Venice, his insights were invaluable for the success of our project.  So, my first move was to get the right co-founder.

To convince him, I started mocking the website and drawing a rough business model idea focussing on understanding what we wanted to do, how, and who we wanted to touch. Once Sebastian on-boarded, we started taking a lot of time to brainstorm on our strategy, mission and business model. We aimed at understanding how to approach the challenge and what was feasible. Once we had a reasonable idea of what we were going to be, we immediately started working on defining our identity and quickly got online on social media making Facebook our hub for communication.

What has been the most effective way of raising awareness for your business? 

Being present and consistent online has been the most efficient way of raising awareness for our cause and business, so far. Press and media features are also doing wonder to help us broaden our reach and spread our message to a bigger audience.

What have been your biggest challenges and how did you overcome them? 

The most significant challenges we've been facing have been to:

1/ Running a business with my better half.  

It is not always easy to separate the personal from the professional. We're overcoming it by clearly allocating responsibilities and tasks while keeping each other accountable and taking all the big decisions together. And we work in different rooms. 

2/Not being in the middle of an ecosystem. 

I used to live in Bangalore, India, where the entrepreneur and creative ecosystem was striving. I could access entrepreneurs of all kind and of all stages, attend meetups and events very easily. These are things that I miss. I find it essential to have the opportunity to speak with people who understand what you are going through. In Venice, there is no such ecosystem and having been in the center of the action I'm aware of the fact that we're missing something. I try to compensate by doing a lot of online reading, learning and attending events in Paris where I go regularly and where the startup scene is growing.

3/Lack of resources:

Like many bootstrapped startup we have limited resources and plenty of needs and ambitions. We've made this limitation a strength by learning to trust ourselves and to learn to do almost everything while recognizing when certain things are beyond our capacity and better outsourced.

How do you stay focused?

I like this question because the more I learn, the more I realize that productivity is crucial and that productivity is, mainly, focus.

I stay focused by doing 3 things: 

1/ Continually creating and evolving a routine which fits me and my objectives, by working on building habits

2/ Removing interruptions 

3/ Using a system of daily to-do lists matched to our company roadmaps. 

I introduce new habits progressively to make them part of my routine more easily or find a better way to do so.  Indeed, I found that implementing big dramatic changes, New Year's resolution style didn't work with me, while let's say introducing one new habit at a time such as  'spending 40 min learning something new' for example, was doing the trick. 

Regarding my to-dos, I organize my daily tasks by priority, identifying the must do of the day and always keeping space for improvisation, opportunities and, obviously, to put out fires. My to-do lists are made of daily micro or routine tasks (checking e-mail, learning something new..)  and 5 to-dos of the day, within which 3 are absolute must do. When I'm too tired to continue working and that I have completed these 3 tasks along with my micro-tasks, I stop working and prioritize rest or leisure,  as taking the risk to burn out or have a migraine attack is never a good idea, according to me. After all, founding a business is more a marathon than a sprint. You need to last the distance.

Something else I do is to remove as many interferences as I can, by filtering my mailbox, checking e-mails and socials at set times, and trying to take calls and meetings only when necessary. The latest one being the part I still struggle the most with as it is not always easy to say 'This is not part of our priorities right now, we'll be happy to meet with you at the right time,"

During the day, I always have a notebook and agenda with me at all time as well as note-taking application on my cell phone.   I use them to write ideas I do not want to forget, and schedule tasks to the following days. This is the best method I've found to achieve the essential objectives of my day without splitting my attention nor fearing to love a valuable idea for my venture.

How do you differentiate your business from the competition? 

We differentiate ourselves from our competition at several levels.

We have a clear purpose. We exist to solve an identified and relatable present social problem, the displacement of a local population due to mass tourism

We offer a tangible solution. The way we tackle the exodus, by focusing on keeping the Venetians in Venice by supporting the local businesses, is easy to grasp and people understand that they can actually help and make a difference,

We know our stakeholders. Our founding team has a deep first-person understanding of all our stakeholders' experience.

We design for people. All our content and tools are conceived with the users in mind.  Our approach is focused on people empowerment, user-friendliness, customer satisfaction, and impact.

We create impact. Every one of our articles, information, and travel tools are designed to improve, directly, the quality of the experience of the travelers and positively impact the local community. 

We create circularity.  We make it easy and highly rewarding for the people who use our platform and the people who work with us to make the right choices and to be driven to continue doing so. Each of the positive decisions they make has a positive impact on not only themselves but also others, ultimately encouraging all stakeholders to repeat the right behavior leading to a wonderful virtuous circle.

We are authentic and approachable. We do what we do because we care and we know that we cannot do it alone. This is something we consistently communicate, and we make a point to make it easy for people to feel close to us and reach out.

 What has been your most effective marketing strategy to grow your business? 

Getting online on social media early on and making our voice and identity unique and clear since the beginning has definitely been important to bring us where we are today. 

Being authentic and seeing marketing as a way to bring our message to more people to increase awareness and impact is key.  

I see marketing as a service to our cause and our audience. The message we spread, the message they receive should be useful to them each time. It should be an opportunity for them to learn or feel something. I am convinced that when people believe you, enjoy your voice and feel close to you and your cause they are more likely to get on board, support you economically and even champion you.

What's your best piece of advice for aspiring and new entrepreneurs? 

Know your why, be true to yourself and your values and stay focused. Do not let anyone deter you from trying. Do not let anything stop you or corrupt you. Be driven by what you have to accomplish and confident that people who need it will welcome it with happiness and even champion you. 

Off course, the road is full of obstacles, but it is also what makes it enjoyable. Each new challenge is a unique opportunity for learning and growth, a new opportunity to define who you are as an entrepreneur and a human being. 

Venezia Autentica is still a startup, but I've learned so much from it already, about work and myself. What felt like the end of the world a year ago is something which I barely notice now, something I am detached from but gives me the right boost of energy to accomplish more. The thing I love about entrepreneurship too is that no matter what your venture will end up being, successful or not, no one will ever be able to strip you from what you've learned and who you've become.

What's your favorite app, blog, and book? Why?

I use many apps and I couldn't do without them. It's a tough choice, but I'd probably say Evernote. I use the paid version, and it is well worth the money. I love being able to record interviews with the business owners we work with or walking meetings with the app or just screenshot full articles to read them later.

Favorite book? This is a tough one. One book I'm reading now which I thoroughly enjoy is 'Heal Me' by Julia Buckley. It is not a business book but a memoir written by a brilliant British female journalist in her 30's and telling her struggle with chronic pain and her search for a cure. She travels the world in search of the person who will heal her, trying desperately to get her life back, to stop being in pain when her local healthcare system failed her. Her story brings many important topics on the table. She's courageous and vulnerable. Her voice is self-aware, witty and unapologetic. An absolute must-read.

I don't really have a favorite blog. I change the blogs I read like I change socks. It all depends on my interest or question of the moment. I find myself often landing on Medium as the variety of their writers equals only the diversity of the topics you can see discussed on the platform.

What's your favorite business tool or resource? Why?

My favorite business resources are currently Quora and Twitter. 

The first one because it allows you to learn just about everything related to business, and beyond, as so many experts, experienced entrepreneurs and leaders take some of their time to share incredible insights on the platform. 

I also love Twitter as it makes keeping up with the latest niche news in tech for example easy.

Who is your business role model? Why? 

Pope Francis!  He's not exactly in business, but I believe he's an excellent role model because of his ability to be fearless and use his voice and position to challenge the status quo while leading one of the oldest, most conservative and probably least agile institution in the world.

Did you know that there is a startup accelerator at the Vatican, now?

Speaking of innovation, I admire Elon Musk for his genius and audacity and for steering the world towards a greater and more sustainable future while at the same time remaining conscious of our limits and trying to push boundaries as much as he tries to protect us from our very nature.

Finally, the work that Ellen Mac Arthur does with her foundation to accelerate the transition to a circular economy is, I believe, outstanding and of great importance.  It is a bold move and an ambitious cause. I applaud her undertaking, and I am convinced of the importance of her work while very glad that the person leading the way towards such a significant shift is a woman.

What do you have planned for the next six months? 

In the next six months, we aim to continue testing our model and make the right adjustments to our strategy and products, assess the impact of our first year in business, nail down our customer acquisition, increase our reach and sales and raise funds.

I firmly believe that to be a successful social business, to be able to make a significant difference, the most important thing that we need to achieve is to have a robust business model, be sustainable and able to grow.

How can our readers connect with you? 

You can follow our work with Venezia Autentica on

Twitter: @veneziaautentic

Instagram: @veneziaautentica 



and connect with me on:

Twitter: @duflotvaleria 


Q&A with Trip Chandler


Inspired by ship chandlers who supply provisions and services upon arrival at port, from staples to specialty items, Trip Chandler supplies the everyday to the extraordinary to visitors and residents of Houston. Founded by Dana DuTerroil and Joni Fincham in 2015, Trip Chandler offers a combined background of experience in the fields of writing, editing, and marketing.

Dana, a Houston native, served as the book editor for Texas Lawyer, a division of ALM Media, and had a lengthy career as a staff attorney with the Louisiana Supreme Court.

Joni, a Houston transplant, has used her MBA and marketing skills working with small non-profits and start-ups to create and execute both internal and external strategic communication plans.

1. Can you tell our readers about your backgrounds? 

Dana: I grew up in Houston and later lived in New Orleans as a student and then a lawyer. I've always loved doing research and writing whether it's the law or travel. I learned my tour guide skills from just living in New Orleans because there are so many tourists wandering around asking for advice! 

Joni: Houston was my fourth move in 8 years, so I had learned a thing or two about exploring new cities and finding your niche. When the opportunity arose to partner with Dana to combine my city exploration expertise and my business background, I jumped at the chance. It's been an exciting adventure helping other fall in love with Houston.

 2). What inspired you to start your business?

Our love for travel and the city we both now call home inspired us to help others do the same because we have so many new residents who move here for work as well as business travelers. 

3). Where is your business based?

We are based in Houston.

4). How did you start your business? What were the first steps you took?

We brainstormed a lot and we came up with a clear idea of our business. We also met with an accountant to determine which type of business would be best for us. Taking care of the practical stuff first made it easier to focus on the fun side! 

5). What has been the most effective way of raising awareness for your business?

Meeting with people face to face - from concierges in hotels to the staff at the Greater Houston Convention and Visitor's Bureau. A in-person meeting is really crucial when you run a business based on personalization. It helps us generate positive word-of-mouth and referrals.

6). What have been your biggest challenges and how did you overcome them?

Mastering the ever-changing social media algorithms! Talking to other business owners and getting their advice has helped us figure out the system (and commiserate!).

7). How do you stay focused?

After every project, we discuss what worked and what we could do better and record our personal notes so we can use that for the next client. 

8). How do you differentiate your business from the competition?

Our level of personalization really sets apart from other tours that focus only on highlights or what they like to show people. We really want people to learn about the city through what they like to do. Additionally, our services are versatile and flexible - we write about the city and create personalized guides for people to use on their own or we can go with them. 

 9). What has been your most effective marketing strategy to grow your business?

Word of mouth and partnering with other Houston bloggers on a blog series has helped us with exposure.

10). What's your best piece of advice for aspiring and new entrepreneurs?

Hang out with other entrepreneurs! Running your own business can be isolating so it's important to talk to others - it can really help you get through a rough patch.

11). What's your favorite app, blog, and book? Why?

Google Maps is pretty indispensable for us because it makes it easy for us to map out a tour route. We have lots of local Houston blogs that we love, but for the business side of things the blog at Duct Tape Marketing has lots of great tips for small businesses. "Steal Like an Artist" by Austin Kleon is an inspiring quick read about creativity.

12). What's your favorite business tool or resource? Why?

We couldn't run our business without Google Drive. It's pretty basic, but we can share all our documents quickly and easily. Plus, it allows us to work virtually, so it's no big deal for one of us to spend a week at the beach!

13). Who is your business role model? Why?

We find motivation and guidance from other women who have made the leap into running their own small business. We're huge fans of the Radio Cherry Bombe podcast because the interviews of women in the food industry are so inspiring. They all start with a dream just like us and just go for it. Hearing their struggles and successes is like a daily pep talk to keep at it.

14). What do you have planned for the next six months?

Focusing on set tours of iconic Houston destinations like NASA and downtown Houston with a Trip Chandler twist!

15). How can our readers connect with you?

Our website

Twitter: @TripChandler

Instagram: @tripchandler


Q&A with Travel Expert & Entrepreneur, Lisa Pagotto

Throughout the last few months, I've interviewed dozens of female entrepreneurs but none in the travel and tourism space until I connected with Lisa Pagotto of Here's is what she had to say. 

Please tell our readers about your background.

I started my career in the travel and tourism industry in 2003, straight out of high school. After completing travel college, I entered into the industry as a retail travel consultant. Over the next few years, I worked my way through various roles trying to find my ‘fit’. I moved into wholesale, worked on the road as a tour leader for several years before being offered a position to start up a new arm of an existing business to see if there was a hunger in the marketplace for private customized tours. It was very much a trial and error role – I was advised if it didn’t take off, I wouldn’t have a job in 6 months.

I ummed and ahhed about taking the role as it meant a significant pay cut but took the chance that I could really create something and make it my own. Within two years, I had turned that ‘new arm’ of the business into a $2.2m sector of the company and was promoted to be National Sales Manager. I was 24 at the time and suddenly found I was managing 7 sales managers across Australia and New Zealand. I was in the role only six months before the parent company folded and we all lost our jobs.

From there, I was employed by another tour company to start a new brand for them. I spent the next 12 months constructing and contracting 400 new tours, as well as launching the brand and getting it producing revenue. Whilst doing this, I was also looking after the national sales and marketing for two other tourings owned by this same company. It was at this moment where I had my light bulb moment. I had literally spent the past few years building brands and business for someone else. This is when I started Crooked Compass on the side - building it up and getting it right whilst I was still working full time. There were still significant gaps in my knowledge and experience so I searched for a more strategic role which I successfully landed.

I convinced my husband that my business idea was so good that we should sell our house so I could really make it happen; so that I would have funding behind me to get it off the ground, surprisingly and not surprisingly, he said yes and within two weeks our house was up for sale. We gave up everything – our house, our lifestyle, and my salary. After some time in the strategic world, it was time to take the plunge and I moved into Crooked Compass full time and have never looked back.

Why did you start your business?

I started the business because I saw an opportunity in the marketplace for showcasing emerging destinations and lesser-known side of common destinations. I saw a niche for an experiential travel product that was outside the norm and this paired perfectly with the moving trend of personalization that has been coming for some time. The style of travel I personally do is all about discovering and sharing the unheard of and when I saw others wanted to do what I do but couldn’t find a way to execute and make this happen, that’s when I saw the need for my expertise.

What market does your business serve?

Crooked Compass caters to those who are well traveled, those who have been there, done that and are seeking something more rewarding from their travels. We cater for the 40-70-year-old travelers who have a little more time and money and those who are seeking a deeper level and educational element to their style of travel.

What's the largest challenge you've encountered as a business owner?

The largest challenge is definitely managing cash flow.

What's your best piece of business advice?

My best piece of advice is that starting your own business is tough. We’ve all heard the saying ‘keep emotions and business separate’ but when it is your startup or your baby that you have given everything up for, emotions do come into play, and often this is hard to manage in the early days.

If you are passionate about what you do, people cannot help but be intrigued and want to listen and help. Passion and ambition are addictive. Surround yourself with people who you want to be like.

How do you like to relax?

Believe it or not, by traveling! But when that isn’t possible, I do like to read – usually books about travel or weird far-flung destinations that I may be able to create some sort of amazing travel product in.

Connect with Lisa on: