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I’ve been an entrepreneur since 2011, starting a private walking tour company before switching to trip planning in 2016. With technology being an ever-changing adventure, it’s been a balance between keeping content current and fresh in an industry where you’re not walking down Main Street USA in the Magic Kingdom every morning.


Episode #064: The Ups and Downs of Being an Entrepreneur

  • Fun fact: Went to 7 elementary schools in 7 years. His dad worked for Walmart and would set up stores in new cities. Dustin’s entrepreneurial skills come from this.

  • Entrepreneurs typically start a new business while working a job. It begins with a side hustle. The unknown is exciting and keeps things interesting as you navigate to see where the business can go.

  • You have to have an initial idea that excites you and you then you work to fulfill that goal and build something. Then how do you fulfill this? This could be with a website, podcast or IG account. Stepping stones and goals and checklist lifestyle. 

  • In the beginning, starting an entrepreneurial project is about catch-up. You have so many ideas that getting them onto the screen and published can’t happen soon enough.

  • Because of the amount of work to do, your mind is constantly focused on more ideas and more content. This can affect friendships and relationships, to the extent of bringing notepads with you to a dinner or having every conversation be about cupcakes or the latest piece of merchandise.

  • Routines are important, but not binding.

  • There’s always more to do, which means that you live through a checklist lifestyle.

  • Know whether you’re an introvert or extrovert will help you decide if you should do networking events, which can be high stress.

  • Creating sources of creativity when you’re living an online lifestyle, such as podcasts.

  • Put yourself in your happy-place, because loneliness can be compounded by daily stresses and things like seasonal effective disorder…where the weather and number of hours of sunlight can bring you down.

  • The big focus of this topic isn’t just loneliness, it’s about levels of trust. As an entrepreneur, do you share what you’re working on for fear of someone stealing your idea? Do you put out a piece of content that’s original, just knowing that by the time you wake up the next morning, the topic will be stolen and rewritten by hundreds of bloggers in “their own voice” so it’s not copyright infringement.

  • The last piece of this is how to work with other creators without focusing on your own business. Folks love to talk about themselves, which allows you the opportunity to help out folks who you may have seen as competition…and then they will turn into the best of friends because you are caring about their adventure through entrepreneurial journey without asking for anything in return.

  • You get good at fixing or helping to strategize on other people’s businesses because you have to think out of the box all the time in your world.

  • It’s easy to get depleted easily because you are constantly hustling to make businesses work and get it up and running and often worked on your own. Distract yourself so you are required to take a break from a new business idea.

  • Being so focused on your business can hurt your relationships, friendships, etc, because you have to devote yourself to it much more than the traditional 9-5 jobs and there are sacrifices you have to make. 

  • It’s important to have a mentor to talk about all things business. Then you can bounce ideas around with, help keep you accountable and challenge you.

  • Every season isn’t for creating. Remember there are cycles for everything and there are times that you should not be creating. Use this time to re-engage with friends and other relationships.

  • Don’t read the comments! (Skip others feedback/comments online)

  • The entrepreneurial journey will have its ups and downs. But the best of your friends won’t judge you on one decision or another. Have fun with it and know this is life and if you make mistakes, own up to it and have fun with it.

  • Quote by Dustin: “Chapters are being written everyday.”

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