Ep # 2 | Risk, Resilience and Rebounding Stronger

Jennifer Jacobs

Jennifer is the detailed planner, travel enthusiast, and proud founder of Explorateur Travel. Travel is changing and more and more, people are seeking culture-rich and authentic experiences. With her experience in the corporate world and a travel obsession, she is eager to make your travel dreams come true! Jennifer loves to eat, take pictures, and most off all, meet people who help her learn about the world! You'll typically find Jennifer with a glass of red wine in her hand and brain-storming up her next trip.



Shantel: Hey everyone we are so excited to have Jen with us, with Explorateur Travel. Jen, welcome to the show.

Jennifer:  Thank you for having me. I'm so happy to be here.

Shantel: Yeah, of course. Just a little bit about Jen and I, so you guys all know, we're friends from college, I've been following her journey, and I'm excited to talk more about what inspired this business venture. So Jen, will you tell the guest a little bit about Explorateur Travel and how you got started?

Jennifer:  Absolutely. It actually started when I planned a trip for my family a few years ago. I had never used a travel agent and it just wasn't something that I wanted to do because I wanted to be able to book myself and plan and just have a really intimate approach to planning for my family and also take the stress out of traveling for my parents. So they had a really concrete plan in place and I realized that there is no service that really provides that intimate approach to itinerary creation and I just thought, this is something that would be so cool to have had, and I love doing this and I love planning and I love helping other people experience the world. So I piloted it for two years and here I am. Dove in and actually traveled for two months to Europe to get some content and just get some inspiration and find restaurants and best places to suggest to clients and here I am a year later, almost.

Shantel: That's amazing. So you plan trips and you travel, that's your day to day life?

Jennifer: Yes. So I plan from A to Z from the point that someone touches down in a new city to the time that they leave and help them find local spots to experience the culture of each city and just enjoy their time to the fullest and find things that they might not have found if they just wandered without a plan.

Shantel:  Neat. So can you tell us all a little bit about how this is different or the guests specifically, how it's different from a traditional travel agent?

Jennifer: Yes, absolutely. So I really wanted this to be a unique approach and an intimate approach to planning instead of just giving someone the typical spots to hit of each city. So I created an ala cart menu where I can plan as much or as little as people want. So if someone just needs to fill in the blanks for two days I can do that, if someone just needs dinner recommendations I can do that, and on the website we have an ala cart menu that you can actually just put into a cart, check out, and if you want to talk about it I set up a consultation. Sometimes people are in more of a hurry and they just need some information quickly, but I try to make it as transactional and as easy as possible. But if it's a really big trip you're already investing in traveling, so I think just a little bit more. The prices are at a very affordable price point so that people don't feel like it's an additional cost onto their travel. And so that you're already going, you're already spending the money, so spend a little bit more and get the most out it as possible.

Shantel: I hate research so I imagine you're solving such a great big pain point for a lot of people that don't even know where to start looking or what sites to go to for recommendations. So you essentially take that off their plate.

Jennifer: Exactly. So we want to remove all of the question marks of travel. Everyone is so busy and when you go on vacation you really want to do exactly that, you want to vacate your life and why add something to your plate that could be a stressor? Like you said, if you don't love the research that's what we're here for. So that essentially, we take a consultative approach. So we're more of a consultant than an agent. Also the product itself while it's information that we're selling, we also put it into an itinerary software and it syncs with your phone so you have access it throughout your trip. So it's really just so automatic and easy for people that are wanting to travel.

Shantel: Yeah, and guys it's amazing and what you didn't touch on yet is that personal approach. So it's nice is yes it syncs to your phone and it's super easy, but you're actually spending so much time and thoughtfulness into what type of travel do they like, do they want to go on bike adventures? I mean, I loved the questionnaire.

Shantel: Can you tell everyone a little bit about that onboard discovery process of yours?

Jennifer: For sure. So you know some people they want the food and wine approach, some people want really active outdoorsy. For example I just did one that was very hiking oriented, whale watching, wildlife tours, trout snorkeling. Salmon snorkeling, yeah very cool. And then I have others that they just want to wander a city and find the best spots for wine and people watching. So when I do that initial conversation or that questionnaire if someone, they might not have time to actually have a conversation, I have a very thorough questionnaire that goes through what were your favorite memories, and you know past travel experiences and that helps me hone in on what really resonates with them and I go from there and build an itinerary that so custom to them and what it seems like they enjoy and then before we finalize it we run through it together again or I get their feedback via email and make any tweaks that I need to, book any tours that they want booked, and just make it completely custom to the person who's taking that trip.

Shantel:  That's amazing and I imagine you're learning something new every time you're working with a new customer because their travel needs or expectations are a little bit different. Do you feel that way?

Jennifer: Absolutely. Yeah. I think that a huge part of this is taking yourself out of it and really flexing to the client, which I think is actually really fun, it's very challenging for me, from a personal perspective because you want to share what you enjoy with people typically. But that's not always the case, people are not all the same, it's not a one size fits all approach. So it's definitely a constant challenge, a constant learning process, and it's so fun learning about the unique experiences around the world through networking and research and leaning on partners and it does require a lot of outreach to people all over the world and it's just really neat experience because it's a constant evolution.

Shantel: That's really neat. So going into your day to day, because it's a little bit different for every customer are their tools or software that you use to help organize or try to streamline as much as possible to alleviate trying to make it so different for each and every person?

Jennifer: Yeah, absolutely. So with as many clients that we're working with consistently, it would be chaos without an actual organizational process in place. So I love Producteev because it is a free project management software up to a certain amount of users, and I do have an employee and it helps me assign tasks to them and assign tasks to me. I get an email everyday telling me what to do, you can add notes, add documents, anything like that can be all held in that software. Then I also use Travefy, which I just love this. I know there are a lot of itinerary creation websites that can help organize travel, but Travefy has a lot of just aspect that I really enjoy. Like they have mapping, so when you actually pull up your itinerary you can see a map of all of the different locations that the client would be visiting. It has my contact information, it exports to a PDF, and it also is accessible by mobile, it holds all documents. So between the two of those things it's a really good checks and balances system.

Shantel: That's greats. When you were a little girl, always loved to travel I imagine, and plan adventures.


Jennifer: Actually that's really funny that you say that, I did love travel but I had never travel abroad until college and I was very stubborn about the fact that I wanted to study abroad and my mom was very fearful of me studying abroad. Which I get, I mean you just want to protect you kids, I get it. But at the same time I just really wanted to experience something so unique and different and I made it happen.  She said, "Well, I'm not gonna help with that, but if you want to do that you can get a loan," and that's exactly what I did, I did the whole process on my own, I applied for the study abroad program, got in, got the passport, got the visa, and that was actually a really pivotal learning experience to go through all of that from a financial perspective and I think it was a definite growing point, but that study abroad session changed my life and I fell in love with travel, I fell in love with Europe, but moreso I just fell in love with experiencing the world and now I just realize that I want to help other people experience and learn to love other cultures every day of my life.

Shantel: Did you always know you wanted to be an entrepreneur? Did you grow up around other entrepreneurs or when did that pivot moment happen for you?

Jennifer: Yeah, actually my dad owns a 96 year old family business. So my great grandfather started it in 1921 in DeLand, Florida. So I've always been around business owners, because my dad would stay up late nights and work in his office, which was right across from my bedroom and I would see the light in his office until the wee hours of the morning and it just really taught a lot of work ethic and made me realize that there's a lot of pride in owning your own business and a lot of hard work. But he provided for his family and my mom was a dedicated teacher and just a lot of motivation in my family in general, so I quickly learned that I liked to be in leadership positions and this just kind of evolved over time through finding out what I did and didn't want to do in my career.

Shantel: Well, it certainly seemed like he helped you think out of the box and imagine more and flex some of that entrepreneurialism that sometimes doesn't come naturally or is a little scary, could be led with fear sometimes. Did he give you a piece of advice that just absolutely stuck with you or kind of a nugget or information that you think of every day or when you're having a bad day?

Jennifer: Yes, actually. See, it's funny that you said that because I was in high school and I was doing a speech for graduation, because I was class president and I was really struggling to find a topic and my dad loves entrepreneurial motivational speakers, books, the whole gamut, which I do too now. Which is hilarious, I never did growing up, I thought they were very annoying on road trips, but now I totally get it and I'm definitely going to annoy my kids with it. But he had this quote, and I won't be able to even say it, but the whole premise is it's a Zig Ziglar quote on persistence and it's basically that there's nothing more important in the world than persistence. Talent and skill and knowledge all of that is superseded by persistence because if you just keep going and you're resilient in what you want to do and what your vision is, then you can achieve anything. So that whole premise actually has stuck with me and I recently released a journal on failure because of it. For some reason that quote has really impacted my life and how I approach all business.

Shantel: I love that. Can you tell us a little bit more about the journal?


Jennifer: Yeah. I was struggling to find a journal that I really wanted to write in everyday because opening a business as you know has it's obstacles, and there are a lot of positivity journals out there and while I think those are amazing I wanted to really flip the perspective on failure and get the point across that failure is a key ingredient to success, and that success doesn't just come naturally and seamlessly and most people that are successful have seen a lot of failure and the difference between someone who quits and someone who is successful is that they just again were resilient in the face of failure. So I created a daily journal and it's a hundred days of failure and it's called How I Failed Today: A daily journal encouraging risk, resilience, and rebounding stronger, and everyday has a motivational quote and a few questions. Every five days has a deep dive on what failures have really impacted your life and how they've made you more resilient and it's a hundred days because in the fails world they say it takes 99 no's to get to a yes. So by that 100th day you should be feeling pretty solid. Hopefully you've gotten a few yes's along the way.

Shantel: That's amazing. I think that's so powerful, I mean it goes into the every mistake or failure you learn something and you can walk away and say, "Oh well, thank goodness I know that now." So either I don't make that mistake again or don't fail the next time. I think there's a lot of power in that journal and congratulations for launching that.

Jennifer: Thank you. I appreciate it. It was fun to write.

Shantel: Speaking of obstacles and those failures, are you comfortable with sharing one recently or something that comes to mind? Like your biggest mistake so far and what's come out of it?

Jennifer: Sure. I think that's a hard question because I make mistakes all the time, it's just how you handle them. I would say that the biggest mistake is, and this is more in general it's not a specific, it led to a few specifics, but really thinking that I had to know the answers for everything starting my business. Just thinking that when I had a phone call with someone I put a lot of pressure on feeling like I needed to know everything about the location they were talking about instead of reassuring them that maybe I don't know every single thing yet, but I have a lot of partners and I do the research and I can take that off your plate for you. I can't have been everywhere in the word, but no travel agent has, not travel consultant has, and really not too many people have in general. So it's just the reassurance and being comfortable saying, "You know, I'm gonna get back to you on that. Let's me look into that," and just feeling like you have the freedom to say you don't know. And I didn't give myself that freedom in the beginning and really it's a daily struggle obviously, but I'm really trying to do that.

Shantel: I think that's great and it certainly translates I think to starting a business and becoming an entrepreneurs. I used to joke about there's not a guidebook or a manual of how do we do taxes and the finance, all of that. But I think that totally translates into, you don't always have to know all the answers when you're starting something either. That's part of the journey and figuring it out, it's part of the fun.

Jennifer: Yeah, if you wait until it's perfect than someone else has already done it.

Shantel: Very good point.

Jennifer: You might as well jump in and make a few mistakes along the way and get better everyday instead.

Shantel: Absolutely. So as you're learning and growing in your business, what does your day to day look like right now and your new teammate? We'd love to talk about your employee and how you delegated some of those responsibilities.

Jennifer: Yeah. So it really flexes everyday because that deep dive conversation that I have with clients, a lot of the times they're not available until after hours because they want to get into a comfortable setting and talk through or grab their significant other or their friends that they're traveling with. So a lot of the time that's late in the evening, and I'm comfortable with that because I can flex my schedule. I'm really a fan of the concept of designing your life for how you want to live, and I think that's the whole point of being and entrepreneur is you have the freedom to design a life that you really enjoy. So I don't have a structure per se on my daily routine, and maybe that is something that I can work on. But I like the fact that it allows me to travel and flex around other people's schedule, and then sit down when I feel that creativity hit me because forcing the creative mindset a lot of the time is a struggle and it doesn't revolve around the eight to five and you can have a really great idea at 9 PM at night and just power through something. But as far as the actual structure that is necessary for a business, that is where the Producteev and the Travefy keep me on track. So as long as I'm hitting those bullets on a daily basis, those things are very important and I do have my fabulous employee who I can just send her a text, send her an email, and she actually has a full time job and does this in her evening hours. So it's very convenient too because by the time I'm wrapping calls with clients I can then send those tasks over to her and she'll get those done in the evening and be ready for the morning.

Shantel: I love what you said about designing your life, and I would love to unpack that a little bit more. So I'm struggling with this balance, that's an interesting word, and we're gonna have to chat about that too, but it's tough I think sometimes, at least for me, to turn off the business. And I feel like you've done that and you're creating this lifestyle that you're flexing your passions and what are your thoughts on balance and how do you find that medium of kind of having some quiet time that you can do other things? Or right now is it just grind, grind, grind, and all you think about is the business?

Jennifer: I think balance is a funny thing. There are days where I'm like, "Balance. What's that?" But I recently I've seen a lot of people say and memes and you see on technology these fun quotes, but I recently saw, "Busy is not a status," and that really hit me. Like, you're right. Just saying that I'm busy, why do we get so caught up in that busy means we're being productive? That doesn't necessarily mean we're being productive, so if you don't feel productive step away and give yourself the room to breathe, go for a walk. I have a seven year old black lab who is pretty much my best friend, so I go on a walk with him and just have a glass of wine and reset and give myself a few moments to breathe. If I really need a reset, travel, but then again a lot of my travel right now is work. So I think it's also defining what's traveling for pleasure, what's traveling for fun, and really making kind of a hard line on that. Which, you're still learning even if you're traveling for fun. But I really think it goes back to busy isn't a status, let yourself have that moment and just give your brain time to process and rest because you're not doing anyone any favors by pushing yourself to the limit. You're not doing your clients a favor, you're not doing your relationships a favor, so do yourself a favor and just focus on you, focus on your wellness, whatever that means for you. It means something different for everyone.

Shantel: Have you had to schedule in that time to kind of take a break or are you really diligent about just not overbooking your day to day?

Jennifer: I am not diligent in that. I have recently made myself schedule wine dates or dinner with friends just to get out of the house because if I'm near my computer I gravitate towards doing something, so the wonderful world of working remotely I think a lot of people can relate to that. But it's just making sure you're holding yourself accountable and if that means that you need to put time in place, that's perfect. If it means that you just need to recognize and be really intuitive with yourself and be aware of it, if it means you need to meditate for 10 minutes a day, then just take that time and schedule it however you need to.

Shantel: Well thanks for sharing. That was certainly helpful for me, I think it's a nice reminder. Oftentimes to hear from someone else that it is okay to breathe and take a break and even if it means you have to put something on your calendar that says go on a walk, that is necessary sometimes.

Jennifer: Yeah, sometimes those get ignored. But you're not alone in that. So you can find the assurance that not everyone has it figured out, including me.

Shantel: Well thanks again for sharing that. Is there anything that you wish you would have known when you first started the company?


Jennifer: Oh, man. That book that you hypothetically just mentioned about having like a map for entrepreneurs that would be amazing. Just knowing, I think, when to hire someone, at what threshold, what point, what financial point, figuring out pricing. Those two thing, the finances are not my love, my love is helping people experience the world. So having a little bit more insight onto that, and maybe planning a little bit more in that instead of thinking it would all pan out, which it has luckily, but I think that's something that a lot of people shy away from because numbers are scary and it can be very awakening, but it's a necessary evil. So if numbers aren't your thing just tackle it and get it over with, and that's something that I really had to do and wish I would have known, Pricing structure, but that's an evolution everyday as well.

Shantel: How did you know when it was the right time to hire your first employee? Or how did you end up figuring that out?

Jennifer: When I was approaching burn out. And I was recognizing that I wasn't strong in every area, and I think you as an entrepreneur I wanted to be able to do it all and being aware and having self awareness to recognize points of weakness was really important. So getting on paper what I enjoy doing, what I was strong at doing, and what was necessary for me to do as the business owner, but then kind of taking the leftovers, putting them in a pile, and saying "Okay, am I comfortable with hiring someone that can do these things?" And I was. I have luckily hired someone who I trust very much and we work together very easily and communication is seamless and we don't have to communicate all the time, which is also awesome and she just kind of predicts what I need and what the business needs and comes to me with great ideas and it's impossible to expect one person to have all of these out of the box ideas and I think there's power in numbers. So trusting that someone else may have a great idea is really important, I think, in growing a business.

Shantel: Yeah, I love what you mentioned about putting your strengths and what you love doing in a bucket and then what you could pass off in another because I'm sure that provided some clarity of, yes I cannot wait to pass off XYZ to free up more time for the things that I love. Is there one thing that's still on your plate today that you can't wait to pass off to either your next hire or your first accountant? Or what does that look like or what is that one task for you right now?

Jennifer: You just nailed it, an accountant. So just anyone to actually sit down and evaluate what is the most beneficial, lucrative where to channel energy. I think a lot of the time I was spinning wheels on things that might not have been the best investment of my time and just realizing where the return is is really important. I think that's a gradual progression in any new business, and if it's not I feel very alone in that. But I feel confident that other feel the same way.

Shantel: Yeah, I handled QuickBooks and invoicing for the first two years of the business, we've recently starting working with Andy over at Accel Financial Services, I'll send you the link if you'd like, but their team's amazing with projections and just analyzing the number and it's like, "How do they know?" But they're great and I'm excited for you when you are ready to pass it off, because it's a good relief for sure.

Jennifer: Thank you, and I think it's a reality check too. It helps you really just be more strategic in your business instead of thinking that something is beneficial and then realizing that you spent a lot of energy in a place that's not giving you the maximum return.


Shantel: Certainly. All right, two more questions for you Jen. Favorite tool, techniques, anything you're loving books, podcasts, what are some cool software pieces or things that we can pass on to the listeners?

Jennifer: Okay, I am a podcast junkie. I love podcasts and whenever I'm on a road trip I just stock up on podcasts. I love The School of Greatness by Lewis Howes. I love Women, Work, and Worth, and anything else that pops up as a similarity to those. Then I have of course some recreational ones, but those are ones that get my creative juices flowing and I find myself needing a pad next to me and dancing the line of trying not to write things down while I'm driving. But it really helps bring me back to that creative place and start thinking on a really strategic level and hearing other peoples success and hearing their failures, it just helps you feel normal and like you're doing something for a reason and that success is out there and keep going and every milestone is something to be celebrates. So I really like those two podcasts a lot.

Shantel: Well I love that and I probably wouldn't be a very good friend if I didn't follow up by saying whenever you're on a road trip please be safe and do not write and drive and text and drive, but those are great.

Jennifer: Okay, I'll do audio notes from now on.

Shantel: Love that. What is next on the horizon for you? Any fun projects or customer projects you're working on that are really exciting?

Jennifer: Well I do want to plan my next trip, so that's in the works and I'm actually up for any fun ideas that anyone wants to throw my way. I'm really tempted by some South America trips, so that's on the horizon it's just budgeting that, finding the best places that will be the next spot that people will really be reaching out to me about. And I may actually be writing another book in the future, and this would be more of an actual book, not as much a journal, but on the same lines of the whole resilience concept. So that's just a little brain child of mine that I've got going on and that'll be down the road, not anytime soon, but the wheels are turning.

Shantel: I can't wait to follow along on social media to see the trip and then of course read the books and guys I cannot vouch for Jen and her team enough, you're traveling you should definitely use their services. It's amazing and it takes the headache out of trying to figure out where to go!