“Surround Yourself with Experts” The 5 Lessons I Learned Being a 20 Something Founder

I had the pleasure of interviewing Michele DiLisio, Founder of PACK, a remote work and travel company for entrepreneurs and freelancers in…

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I had the pleasure of interviewing Michele DiLisio, Founder of PACK, a remote work and travel company for entrepreneurs and freelancers in search of a supportive community and a global perspective. PACK launched its first month-long retreat in Bali, Indonesia in 2017 and after just three retreats has been featured in publications such as Forbes with alumni hailing from 15 countries.

Jean: Thank you so much for doing this with us! What is your “backstory” of how you become a founder?

I don’t have the typical “startup” backstory. I graduated from Arcadia University with a Bachelor’s in English, I worked for a law firm, managed a restaurant, and landed a job at a small agency handling travel and logistics for high-profile clients. After a year in my position, I convinced my boss to allow me to move from Philadelphia to Lake Tahoe and work remotely, an idea they were less than thrilled about (and a favor they never let me forget). Working remotely granted me some flexibility, but it was a thankless job and I found it increasingly difficult to wake up and dread the workday ahead. After a few more moves around the country, I decided to spend a month in Bali with a brand new company that promised the ability to work and travel with a community of like-minded professionals. Overall my experience was eye-opening, but I’m a meticulous planner by nature and I felt the logistics, facilitation of activities, and social climate were lacking (they essentially dropped us in a foreign country for 30 days and left us to our own devices). A few of my fellow participants suggested this type of experience was right up my alley, and I shrugged them off, but a year later when I was faced with more difficult clients and an unbearable amount of job dissatisfaction, I realized now was my chance to start something of my own. I had ideas about what needed to be different, I had the logistical skills, and I was young, unattached, and hungry. I booked a meeting with the best business contact I had, asked for advice on where to begin, and (to my shock) left with enough money to get us started and see if we could make this work.

Jean: What do you think makes your company stand out? Can you share a story?

There are three unique aspects to our program that I’ve worked very hard to create and maintain:

  • Our Community: Growing up I didn’t have a lot of friends. I always felt lonely and I valued different things from my peers. When I traveled with other remote work companies, I found that although my values matched more with their communities, there were vicious cliques, an elitist vibe, and an inauthentic attitude that made me feel even more alone. I interview each participant myself to make sure we accept those who are ready to be open-minded, respectful, and accepting of their fellow travelers. When you join us, you are immediately accepted as you are. This is a safe space, a judgment-free zone, and a place where you can learn, grow, and be inspired by our differences. This attitude of inclusion regardless of nationality, background, socioeconomic status, etc. is increasingly rare in our world and I like to think we are doing our part to nurture it just a little bit.
  • Our Logistics: This may not be the sexiest aspect of a company to sell, but it makes a world of a difference. We pick everyone up at the airport when they arrive, we make sure our apartments and coworking spaces are safe, comfortable, and well-appointed, and we have two facilitators on the ground at all times to deal with the inevitable travel issue. No one is ever on their own in a strange city, and we take great pride in our ability manage logistics so you don’t have to. This allows our participants to be productive the minute they step off the plane, and feel comfortable in their home for the month.
  • Our Impact: Travel is great, but it was never enough for me to just take a group of professionals to a location to explore. The rise of the “look at me” traveler has always been a bitter pill for me to swallow. I wanted us to do more. That’s why we always make an effort to connect with the local communities on a personal and professional level by lending our skills to budding businesses, young entrepreneurs, and even animal welfare projects. It’s absolutely imperative that we leave these locations better than we found them. It not only benefits these communities, but it makes us better humans.

We aren’t the first or the biggest remote work and travel company out there, and that’s okay with me. I firmly believe it’s more important to focus on the participant experience, the quality of the product, and to grow slowly. Being a small company allows us to apply a personal touch to our experience that the larger companies can’t offer. I have attended every retreat we’ve run since we launched, I organize all the housing, coworking, side trips, and programming while we’re in a location. It’s a big undertaking, but I believe in what we’re building.

Jean: Are you working on any exciting projects now?

In the next few months we are working on new partnerships with entrepreneurs and experts in their fields to launch shorter retreats (10–14 days) where participants can live in exciting new locations while also growing their professional portfolio and learn new skills while surrounded by their peers. We are also going to be launching a new type of retreat where we spend more time giving back in a real way (up to 2 weeks per trip spent volunteering and mentoring with locals, refugees, and animal welfare groups). Both are very exciting — I am always looking for new ways to grow professionally, personally, and have a bigger impact on the world.

Jean: Do you have a favorite book that made a deep impact on your life? Can you share a story?

I recently read Rescue Road by Peter Zheutlin, which tells the story of the volunteers who work tirelessly rescuing, caring for, and transporting dogs who would otherwise be euthanized from the southern United States on what they call the “Last Hope Highway” to their forever homes. If you know me, you know I love dogs more than almost anything, and this book inspired me, brought me to tears of joy and grief, and shook me to the core. Not only is the cause noble, but the biggest lesson I took away was how devoted these people are to their cause. This is the story of true passion and devotion to an often exhausting, difficult, and neverending vocation. Although the story is about animal rescue, the message is clear: if you love what you do, if you believe in your cause, the struggle is always worth it. When I quit my 9–5 in favor of an unreliable paycheck and a business that would demand more of me than I ever imagined, this was the feeling I was chasing.

Jean: What are your “5 Lessons I Learned as a Twentysomething Founder” and why? Please share a story or example for each.

Surround yourself with experts.

I’m great at managing logistics, putting out fires, and creating community, but I don’t have a business degree. There were (and still are) aspects to running a startup that are a mystery to me, and I knew early on that it made far more sense to surround myself with others who had those skills and who had spent years learning from their mistakes, than to bang my head against my desk attempting to get it right. You can’t do it all, no matter how much you’d like to. The only way to succeed is to ask for help and ask for it often.

Be kind to yourself.

Running a startup is a difficult, demanding, and never-ending task. Although it’s crucial to work hard and put in the hours, it’s just as important to allow yourself a break and stay fit, sane, and healthy. I had a tendency to overwork myself when I was in school, and I’m not much different now. One of the most important things my mom used to tell me was that there is nothing more important than eating and sleeping. Imagine how much more inspired and productive you could be if you get enough sleep and you’re not living on fast food and diet coke!

Celebrate the small victories.

When you’re working around the clock, battling marketing, paying the bills, and managing the infinite details of a startup, it’s easy to get caught up in the struggle and overlook the positives. Did you have a great call with a client? Did someone mention they heard of your company from a friend? Did you learn something new? Awesome! Not everyone has what it takes to start something from scratch and pour their heart and soul into it, and it’s absolutely necessary to your morale (and sanity) to recognize what you’re doing right, even if it seems like everything is difficult and the bank account is always in the negative.

Never stop learning.

I read 5–10 books at once. I listen to podcasts, read articles, ask questions constantly, and always assume I know less than those around me. The most dangerous thing you can do in business is assume you know it all. I guarantee that someone sitting across from you in the coffee shop has some kernel of knowledge you can apply to running your business better. I’ll be the first to admit I don’t know what I’m doing and the small amount of success we’ve experienced so far has not been luck — it’s largely been because of the input, knowledge, and help we’ve had from countless members of our community and network.

Chase meaning, not monetary success.

Ask yourself why you’re doing this. If the answer is money, quit now. I know it sounds crazy, but all the most successful business people did not begin this journey because they were chasing a paycheck. They believed in something: an idea, a product, a vocation, etc. Success is not guaranteed (failure is more likely), the road is long, and gone are the days of a reliable income. A lot of startups get caught up in growth and profits. Sure, one of the goals is to make money, but I have always thought it was more important to be sure we had a great product we believed in, even if it meant our profit margin was next to nothing and we’ll never make a million dollars. If a fat paycheck was all I cared about, I would have stayed in my reliable, bill-paying desk job.

Jean: Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

Sophia Amoruso of Nasty Gal. The story of starting a business with no experience but a whole lot of passion resonates with me. I have often felt that I started my company because I felt I had to — I couldn’t bring myself to do anything else, and I desperately needed to believe in what I was building. Nasty Gal and #GirlBoss are now so much more than vintage clothing — the community is inspiring women, sharing ideas, and making an impact, all of which I am constantly trying to do with PACK.

— Published on June 27, 2018

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