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An Entrepreneur’s Guide to Starting and Managing an Unconventional Business

Executive Summary

Tamara Jacobi chose the jungle over Goldman Sachs after graduating college.

  • She and her family purchased 5 acres of tropical paradise near San Pancho, Mexico in 2005.
  • Jacobi pursued her passion by starting a business around it, and shares the steps it took to become successful.
  • She says any business, especially an unconventional one, needs a business plan and support from mentors or coaches.

On a cold day in February 2007, as I skied down the Middlebury Snow Bowl in my cap and gown, I had a decision to make. In one hand, a prestigious diploma, a ticket to a traditional career. In the other hand, a freshly printed eco-lodge business plan. As I floated through the powdery snow, the tug-of-war that had lingered within me came to an abrupt halt as clarity struck. I realized that this was no longer just a business plan for my father’s dream. The eco-lodge had become my dream—our dream. The jungle, my family, and Wildpreneurship beckoned. Inspiration pulled me away from Wall Street and the concrete jungle and toward the real jungle and Tailwind Jungle Lodge.

What is Wild Entrepreneurship? 

Being a Wildpreneur is about living consciously and designing your life path. You don’t necessarily have to create your own business.

Why “wild” entrepreneurs? We are far from conventional! As we blaze our own trails, we define success as a quality of life and richness of experience beyond dollar signs.

You, too, may be following an uncharted entrepreneurial road—starting a business, living wild, free, purposefully, out-of-the-box, tuned into your heart, and aligned with your values, whether you want to podcast from an Airstream, create an adventure company in the mountains, make organic cupcakes, open a daycare center, or become a life coach.

Perhaps you’re a corporate burnout, retiree, or recent graduate, the following steps support you as you blaze your own trail from the daydreaming stage to success.

6 Steps to Starting a Business and Pursuing a Passion 

Step 1: Choose Your Own Adventure

Remember the Choose Your Own Adventure kids’ books, where you got to assume the role of the protagonist and make choices that determined the outcome of the plot? This is your real-life opportunity to design your life adventure. As you stand at the bottom of this mountain of potential, this is no longer a fairy tale—decisions now will affect the direction of your life.

Start by brainstorming ideas and possibilities to determine the terrain, vehicle, and schedule that suit you the best. Eventually you will stumble on your home run, but first, spend time on the daydreaming stage.

Once you’ve chosen your adventure, pick a catchy name. We began as Tailwind Outdoor and evolved into the Tailwind Jungle Lodge. A name can say so much about a business. For us, shifting our name allowed for a much more appropriate description of who and what our business had become. What will you call your wild business? Choose wisely; you’ll be saying it a lot.

Step 2: Research

Before you hit the trail, do your homework. In this modern world, we have endless resources at our fingertips. Explore other wild businesses with a similar theme to yours and google your idea. As you design your adventure, you don’t have to reinvent the wheel. Use the wheels that already exist and add your own twist. It’s absolutely OK to imitate before you innovate. What you are doing will ultimately be unique as you infuse your own style and personality into your business.

Research Categories:

  • Fellow Wildpreneurs: Have other adventurers done something similar? Leaders in your field are an excellent source of guidance and wisdom.
  • Industry: Familiarize yourself with your field—research trends, major players, risks, and sales data.
  • Ideal Customer/Target Market (Your Tribe): Research demographics, geographic location, profile, how needs are or are not being met.
  • Products and Services: Research what you will be offering. How will it be developed, produced, created, offered, and/or distributed?
  • Operations and Management: How will you structure and manage your business? How have others done so?
  • Feedback: Engage your fellow Wildpreneurs; they may be your best evaluators. Given their own adventures, they are likely open to seeing the potential in unusual possibilities and will give you honest, useful, and objective feedback. Find your devil’s advocate.
  • Social Media and Email: Test the waters by sending out an email or posting your proposed adventure on the social media platform of your choice. Poll your existing network to gauge interest and guide your research.

Step 3: Support: “Find Your Yoda”

“Find your Yoda,” says brew master and successful entrepreneur Jim Koch in Quench Your Own Thirst. He recommends finding “the very best person in the world” to mentor you and help you achieve your best.

“Prior to getting started, I wish I would have known the importance of mentorship,” Founder of Zen Girl Chronicles, Mandy Burnstein said. “During a yoga-teacher training, I was ‘assigned’ a mentor who ended up being the absolute perfect fit for me. I learned (and am still learning) so much from this amazing woman, twenty-five years older than me, more than three decades of experience in my industry. What a gift that was, being paired with her.”

Every good adventurer needs support from the get go. While friends and family are crucial, tapping into the wisdom of a good coach or mentor is another key ingredient to success. When it comes to mentorship and coaching, there are many forms (casual, formal, paid, etc.). Be mindful of whom you choose. A paid mentor or coach will charge a price for these services (this typically makes the commitment more serious and professional for both the teacher and the student, whereas an unpaid mentor or coach will be more informal and relaxed). The type of support you need will depend on your personal needs—career transitions, strategic thinking, accelerating change, goal setting, accountability, and so on. Having an accountability buddy is another great support system.

Step 4: Specialize and Simplify

Choose one summit instead of an entire mountain range.

Many people don’t specialize because they’re worried about limiting themselves. However, if you specialize—hone in on your tribe and niche—you give yourself a chance to go deep, get creative and become a master of your trade.

For example, if you’re creating a restaurant, start by defining the type of food you plan to serve (Thai, Indian, Tex-Mex, etc.), and then specialize by identifying a few excellent dishes. This will reinforce your reputation for quality and attract hungry customers, whereas loading the menu with mediocre options may leave tables empty.

Start small and simple, then grow from there. Avoid “lazy simple,” embrace “profoundly simple.” No short cuts, just smart design. Don’t hesitate to hire on help if you need it! Your business will suffer if you spread yourself too thin. With smart design in mind, build your business on quality whenever possible.

Step 5: Barter

To generate brand awareness of your business, you’ll likely need help. You might realize that you need to bolster your marketing efforts with a website and logo or you may need resources that are not immediately available to you.

Trading is one of my favorite perks of Wildpreneurship. We have traded stays at the lodge for work on our website, photos, promo videos, organic veggies, clothing from local galleries and more. These trades have led to new relationships and beautiful synergies between wild businesses. How, what, and with whom can you barter? Note: If you’re a natural giver, beware, not everyone is as giving as you are—be cautious and make sure that trades feel fair and expectations are clear.

Step 6: Map and Compass

Just as a map and compass would keep you pointed in the right direction, a business plan will give you clarity, guidance, and direction. What is your ultimate destination? This map will give you a tangible plan to share with others (particularly important if you’re planning to work with partners) as well as a clear platform for discussion and springboard for the work that lies ahead. Need some guidance?

Try the “Nutshell Business Plan” worksheet to get started →

If your business plan doesn’t feel right the first time, don’t rush it! Procrastination may actually be beneficial here. The tendency to delay could help Wildpreneurs build businesses that last. If you have the gift of time, try being a mindful tortoise instead of a speedy hare. Remember that every good plan is accompanied by a backup plan in case of emergency. Should all fail, it’s good to protect yourself. You might even create a bailout plan, too. For example, if for some reason, you are unable to continue running your wild business, could someone step into your shoes, or would it be possible to sell the business?

Think of your wild business as a sum of smaller parts that work gracefully together. With these essential tips and tricks, you’ll be well prepared for the adventure ahead.

Adapted with permission from Wildpreneurs: A Practical Guide to Pursuing Your Passion as a Business by Tamari Jacobi, copyright Tamari Jacobi.

Bring It Home

A couple of years ago, I worked for a local marketing company that specialized in helping luxury car services with their marketing strategies. About four times a year, we would host live “bootcamps,” which 10-20 limousine operators attended to learn about various parts of the sales and marketing process. In every session, we covered business plans. Whether your business is merely an idea or it has been in operation for a decade, it’s never a waste of time to outline your goals for the future.

The lesson I learned from participating in these bootcamps was to plan and prepare even if when you’re trying to create something new or investing in something that has rarely been done before. Had I not seen the light flicker in limo business owners’ eyes every time they walked away with a plan for starting a business on its next phase of growth, I’m not sure I would fully understand its value today. How does having a plan in place make you feel when you’re embarking on a new challenge, like starting a business? Comment below with one benefit you’ve experienced from preparation. ~ HarperCollins Leadership Essentials

Tamara Jacobi

Known as "The Jungle Girl", Tamara Jacobi is the founder of the Tailwind Jungle Lodge and author of Wildpreneurs (HarperCollins Leadership, Feb. 2020)--a guidebook for turning passion into business.

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