Annie Pestel: The Road Less Traveled

Annie Pestel: The Road Less Traveled

Forget Expectations and Commit to Yourself

Active-Duty Entrepreneur

Annie didn’t waste any time building the foundation for her first company. Immediately after graduating at the top of her class from West Point, Annie began The Brazen Gourmand.

She was able to balance being a start-up founder and a full-time Army officer by taking the pressure off herself. The Brazen Gourmand was simply a creative outlet where she expressed herself through pictures, writing, consulting and design.

As a creative individual in the military, Annie created her company out of necessity. She needed an outlet to express herself. But, by treating it as a hobby, there was no pressure for it to be a business, it was just a fun project to work on during her free time.

Day to Day Life

Despite her entrepreneur experience, Annie’s transition out of the military was still not easy. The sudden freedom after leaving active duty proved to be both a blessing and a curse. The extra time was great for her business, but she also had the self-awareness to recognize that she needed more structured days to reach her full potential. Annie created this structure by scheduling her day into 15 to 30-minute increments. To be more effective, each increment was focused on different parts of her business.

The structure became a source of comfort for Annie. Every day was different, but the structure was always the same. It developed a pattern for her life, relieving the burnout from feeling like she always needs to be working.

In general, Annie has long, but fulfilling days. She works on her business from 7:30 am to 3:30 pm. Then, Annie focuses on specific projects throughout the evening. She said that the days are long, but because her passion is her profession, it doesn’t feel like work.

Annie makes the powerful point that work and life don’t have to be hard. The military might teach people to “Embrace the Suck”, but our work can be easy if we are doing what we love. She cautioned, however, that it still takes time and effort to get to this point. In Annie’s words, “Don’t worry about what you should be doing, do what you want to do.”

Hobby to a Business

Annie didn’t think it was possible to turn her hobby into a sustainable business. She thought she had to follow a predetermined path, but it wasn’t what she wanted. The transitioning course about trade schools and apprenticeships opened her eyes.

The instructors kept asking, “What do you love to do?” Annie realized it was cooking and decided to apply to culinary school. After being accepted, she was thrilled about her exciting new path. A month before she left the Army, however, the culinary school went out of business. The school didn’t work out, but it revealed similar opportunities.

None of them would have been possible, however, without Annie’s initial decision to take the road less traveled. She said, “We need to be honest about what we really want to do, but it takes significantly more courage.”

This courage and persistence sustained Annie through the difficult times. She had to keep telling herself, “You can really do this.” She also had to manage her own expectations. In the beginning, she knows that she wouldn’t have much to show for her leap of faith. It was the start of a long road, but it was worth it for her to follow her passion.

Taking the road less traveled will always create critics. Most military mentors weren’t supportive, but Annie’s Brigade Commander was supportive because of her excitement and confidence. Her family and friends, however, were supportive because she had been pursuing this path for years. As a result, the decision to leave the Army and attend culinary school made sense.

Annie says, “People will hear your passion and they will understand. They can’t ignore conviction and confidence, don’t apologize for following your path.”

Transition Challenges and Resources and Stanford Ignite

After leaving the military, Annie still struggled. She said, “In the beginning, you don’t know what you don’t know.” She had to start from scratch. Fortunately, Annie was humble and hungry, taking advantage of every online resource: Boots to Business, local Small Business Center and soldier for life transition courses. These classes helped her build the basic foundation for her business and opened her eyes to opportunities.

The next step for Annie was to learn from people already on her path. The organization, Million Cups, gave her an opportunity to meet once a week with a group of entrepreneurs. Someone pitched their idea, then everyone provided critical feedback. Another valuable program, The Vet Tech Trek, showed her that veterans can thrive in non-traditional paths and that she was not alone. These courses showed her what could be, but she still didn’t know how to get there. Finally, Annie recommended podcasts. Specifically, she cited the Gimlet podcast that walks through the process of starting a podcast company.

In general, Annie advocated the importance of leaning heavily on the Veteran community. People with similar interests were incredibly supportive, answering all of her “dumb questions” that she wasn’t comfortable asking anyone else.

Stanford Ignite Program

The most influential step in Annie’s personal and professional development was the Stanford Ignite program. It taught her the tools to make her dream a reality, giving her the confidence to find the necessary resources and to ask the right questions.

The Ignite Program is essentially a micro MBA at Stanford. For a month, it consists of full-time classes and project work. Before beginning, everyone pitches an idea for a business. After peer voting, the top 6 or 7 entrepreneurial ideas are incubated throughout the program. In addition to the project, the Ignite Program tries to cover 2 semesters of a business school course every day.

Annie strongly recommends the veteran only Ignite Program. The professors are the same, but they spend more time on finance and less time on leadership because of the veterans’ prior training and experience. Another benefit to the veteran’s program is the cost. Normally, the Stanford Ignite program costs around $15,000. The total cost for the subsidized veteran program, including room and board, is only $2,000.

For Annie, the best part of the Ignite Program was the fellow veterans. Ego, rank, and experience were all checked at the door. The veterans were united in purpose and focus. They had similar mindsets, but different backgrounds and skills that they each brought to the table.

Annie’s idea was selected and refined. Beginning as an online events business, her project transitioned to a group dining reservation system. At the end of the month, one of her mentors asked if she would cancel her flight to stay and work on the project. True to form, Annie didn’t hesitate. She put significant time and effort into the project, but she had the self-awareness to realize that the tech industry was taking her away from her passion for creativity.

Because she was committed to herself, Annie made the incredibly hard decision to walk away from Silicon Valley, leaving behind money and mentors. Her main investor, however, fully supported her, not her idea. Despite Annie’s fears, he had no problem with her pursuing her passion. She had to stand strong to follow her true interests. The self-aware commitment to herself drove her decisions, regardless of the consequences. Annie said, “You have to first fully commit to yourself and to your happiness. No matter how constrained or confined we might be, we can still control our attitude. We can make the most of hard situations.”

Final Takeaway

Annie’s powerful final thought was to commit fully to ourselves and our happiness. She encouraged people to ask themselves, “In a fantasy land, what would I be doing?” Then, strip away any idea of what we think we should be doing.

Because she follows this advice, Annie feels as proud of her work now as she did when she was in the military. In her words, remember that “something other than serving in the military is not a failure. It is another way of serving and it reflects extremely well on the military, it is an example to civilians of the power of military service”

About the Author

Alex Olsen is an officer in the Air Force. After graduating from the U.S. Air Force Academy, he attended the Harvard Kennedy School where he studied business and leadership. Alex currently serves as a resilience trainer for new recruits, teaching tools and tactics to help them reach their full potential.