Welcome Ashley Cheeks, Our New Educator at Pitch Investors Live

Ashley Cheeks is no stranger to entrepreneurship. She’s used to getting rounds of interviews with bankers and investors and cold-calling prospects. It’s no surprise that while searching “entrepreneurship” on Facebook, that she came across PITCH Investors Live. “I tried this avenue for finding investors to add more value to entrepreneurs,” says the Houston, Texas, mother-of-two. “When I saw investor and marketer Jason Stone taking a pitch, I knew this was better than Shark Tank.”

Cheeks is not a business broker, rather a business plan consultant and educator, who advises companies at PITCH Investors Live on how to do their best during their pitch session. On learning about the process, she said, “It drives me insane when entrepreneurs feel that they are not capable” and advises that “when they are aware of their capabilities, they can build empires.”

Cheeks has built her own successful consulting empire with Written Success, but the path to her own freedom came with its hurdles. “People told me I couldn’t do it, run my own business. I have a young family, a child with special needs to take care of. Once I proved myself, everyone jumped on board”, she shared. It took an MBA and two years of developing her business before jumping into entrepreneurship full time. “I love the freedom,” says Cheeks, who is writing a book on the practices of building a solid business plan and pitching to investors.

PITCH Investors Live writer Alice Hlidkova, interviewed Cheeks to get her perspective on the business of pitching and on her new role on the team as an educator.

1. How did you learn about PITCH Investors Live?

“I am constantly searching … new ways for my clients to find funding. Recently PITCH came up on my radar, and once I learned more about their mission and method, I realized they were exactly what many entrepreneurs are looking for as a solution. I quickly became excited to start offering them as a great option for some of my clients who are on the hunt for the right investor.”

2. Tell us about your role.

“I collaborate with PITCH by providing pitch consultations for entrepreneurs who are scheduled to pitch to investors on the PITCH Investors Live platform. I also provide free trainings and educational resources about tips for pitching to investors.”

3. Can you tell me about your entrepreneurial journey?

“I worked for several corporations, including Fluor and GE, as a Proposals Manager. My job was to support the sales team in getting them ready for client pitches, and prepare written business proposals that would attract revenue for the company. Meanwhile, just as a side hustle, I freelanced for large consulting firms where I provided strategic business plans. I later founded Written Success in 2009 where I could support clients 1-on-1, as a part time business at first. That business morphed into a company that provides entrepreneurs with help developing business plans, preparing for investor meetings, and getting them positioned to secure funding for their business.”

“In January 2016, I made the decision to leave my full time job with GE and focus on growing Written Success. It was terrifying, but I have no regrets.

4. What best practices did you develop to train startup founders to pitch investors ?

“There are three things that I consider as best practices when it comes to training entrepreneurs for pitching. First, baselining their business knowledge is key. How well they know their business and how they would answer key questions is the primary goal when getting started. How an entrepreneur can speak to his or her business basics can make or break their funding potential, and part of my job is to help them uncover specific numbers and information bits that they’ll need to have handy before the pitch.

The second practice is to raise their awareness on key things to avoid during the pitch. This can include body language, use of certain phrases, and other things that add to their impression on investors. An entrepreneurs’ literal speech is only a small piece of the overall communication, and helping them prepare to be an excellent communicator with their face, body, and tone are helpful in preparing them for the best pitch possible.

The third best practice is more related to the mind game entrepreneurs play with themselves. The thing I focus on is their biggest mental blocks in a pitch. Usually, entrepreneurs have a fear or two that can become a problem during the pitch. Sometimes that fear is about looking unprepared or fearing they’ll come off as lacking in business-savvy. Sometimes that fear is about revealing too much proprietary information during the pitch, or of being talked into negotiating too much equity away. Sometimes it is fear of exposing something personal unintentionally or being judged for something during the pitch. Whatever that fear, it is important to recognize it and work together to mitigate it so that the entrepreneur can feel confident about their impending pitch.”

5. What are top three challenges startups face when communicating with investors.

“Usually, startups in particular have a few common challenges. The first, no matter their background, education, or experience, is that they have fear that they will be seen as unintelligent or non-business minded. This fear almost always impacts the way they would naturally respond to an investor. Instead of giving direct answers, they can often botch their own pitch by trying to appear more knowledgeable, instead of being genuine and honest. This facade can be distracting to investors and taint the entire pitch in a negative way.

The second challenge is about focus. When entrepreneurs pitch, they often struggle with how much to share about their business. This applies both forward and backward. When they focus too much on the variety of plans they have for the business, or the different directions the business can go, then they can lose investors by giving the impression there is no clear singular strategy for the business. Likewise, it’s easy for entrepreneurs to focus backwards by expounding too much on the journey to date, instead of explaining plans for the future. Both of these are a result of lack of balance and focus during a pitch.

The third challenge startups face is more obvious — not knowing their own business inside and out. Not that one person needs to know 100% about every detail of the business, but everyone on the pitching team needs to be able to collectively speak to the most important aspects of the business. Usually entrepreneurs underestimate the areas of weakness in their own business strategy, their numbers assumptions, and their general market. Strengthening awareness in these areas and being prepared to communicate intelligently on these points can make the difference in getting funded or losing an opportunity.”

6. Tell me about you… Why do you do what you do?

“I love helping founders to find the resources they need to continue their dream. Those once-in-a-lifetime moments where the money needed is “right there” via an investor,

or the perfect partner is one pitch away — entrepreneurs deserve to be prepared for that. An entrepreneur is one good pitch from changing their entire course if they can just get their pitch right when the opportunity presents itself.

That moment when a client calls to say they nailed their pitch, got their investor onboard, and their business is about to take off — that is the most rewarding part of it all. That’s the moment where their life and business is literally changing and taking a new path, and I am filled by helping to make that possible.”

7. What is next for you on your life and business journey?

“As a Business Plan Consultant, I’ve learned a lot and have broken a couple of traditional rules about how to write a business plan and how to prepare for an investor pitch. I’m taking those non-traditional things that have led to high funding rates and strategy clarity for entrepreneurs and am writing a book that will be released in Q1 2019.

I’ll also be growing the Written Success team and will be expanding the business. Short term, that is next for me professionally.

Regarding my life journey, increasing presentness and balance is always the goal. My husband and I share passions for being parents of a young son and daughter, as well as building the other businesses we have together. It leads to a constant rhythm of forward momentum, but I try to stay mindful and enjoy the moment. My goal is to become more masterful at being present.”

Although Cheeks has her path carved for her, she stays busy. There is much work to be done, reflects Cheeks who understands the importance of “baselining” or building a business from scratch, and communicating the right information to investors. “There is that voice of doubt, that plays with you. You think what you say may come off as unintelligent to investors and you are terrified to express your failures,” she says, indicating that communicating setbacks to investors in a positive way is a powerful tool.

Beyond mentorship and empowerment, Cheeks focuses on capital raising and shares a tip: “Figure out where is the money hiding. The money is there, and don’t let the investor scare you.” She adds that getting to the point is key, and adding visuals to marketing materials creates engagement. “Business planning has antiquated rules,” says Cheeks, who finds leisure in breaking traditional rules with intention. “At the end of the day, we are people who are communicating their desires, needs, and dreams.”