Co-Founder and COO of Go Charlie.Ai, Brennan Woodruff, knows how important family is. Ensuring that your family is aware of the risks that come along with entrepreneurship is a necessary step when looking to start your own business. 

From learning through connecting with customers, to the importance of patience, to being mentioned in the Wall Street Journal, Brennan has incredible nuggets of gold to share through his entrepreneurial story.

What are three things every Entrepreneur should know?

Brennan’s first two points when discussing the things every entrepreneur should know were simple. The first being that everything is going to take longer than you expect – even when you plan for the added time! Secondly, Brennan mentioned that you’ll learn more in two minutes of conversation with your customers than you would in months of ongoing market research. 

The last point Brennan highlighted with somewhat of a deeper explanation. If you’re in a long-term committed relationship, if you’re married, have a family, even if you simply have a dog – it’s really important that you let them know what you intend to do. 

Tell them about your decision to become an entrepreneur. Help them be prepared for and understand the financial risk and time commitment you’ll be taking on. Starting your own business comes with a lot of responsibility and it will certainly impact your day-to-day life and your relationships. 

Being honest and open with your loved ones about the implications of this decision is crucial.

What problem does your business solve and who are its customers?

Brennan let us in on a little secret: the business he co-founded, Go Charlie.Ai, actually began as an AI puppy model! Although kidding, if you take a look at their website you’ll see that it essentially is an AI puppy. However, rather than being a pet, it’s a digital marketing assistant. 

The idea stemmed from their knowledge that businesses need to have an online presence – particularly after the pandemic. Nowadays, it is nearly impossible to conduct business without having a digital presence, unless you already possess a well-known and established brand like Lamborghini, for example. 

Initially, Brennan and his team of co-founders’ goal was to develop a tool that would act as your marketing and content creation companion. Whether it’s designing your webpage, building your website, managing your social media presence, or optimizing your SEO to increase brand awareness, Charlie aimed to simplify these tasks using artificial intelligence (AI). 

By simply inputting a small amount of information on your business, like a puppy being trained, Charlie will learn and grow with you as you interact with it. The more you collaborate with Charlie, the more effective it will be in assisting you. 

Go Charlie.Ai is an AI tool for anyone who has a brand, product, or service that they’d like to market online.

What inspired you to become an Entrepreneur and would you do it again?

Brennan shared honest concern that his answer would come across as egotistical, however, the pivotal moment that inspired Brennan to become an entrepreneur occurred when he was at SoftBank Vision Fund. He noticed that all aspects of the business that intrigued him happened at the portfolio company level and he wasn’t terribly passionate about finance. 

Although he was making money and living a certain lifestyle because of it, he began to realize that he wanted to make an impact and connect more with customers. With this knowledge in mind, he joined a program called “The Morning Brew Accelerator,” which has now rebranded to “The Morning Group Newsletter.”

The program was focused on building a modern media company through newsletters and Brennan was assigned to a team of entrepreneurs who had already started their own companies where he found himself outperforming them. 

It brought Brennan to the realization that starting his own venture wouldn’t be as difficult as he thought – he had the necessary skills, he just needed the right idea and space to work in. Initially, this led him to consider creating a music NFT company initially, but ultimately he decided to dive into generative AI. 

Brennan saw generative AI as one of the most groundbreaking technological shifts that could enable significant advancements in various fields and he was both inspired and confident enough to go for it. 

When asked if he would do it again, Brennan mentioned his intention to live a life with little regret, stating that “wishful thinking is definitely an easy poison to drink.” Although entrepreneurship can be an isolating journey sometimes, the high notes he experiences as a result of his entrepreneurship are far beyond some of his most impactful moments so he absolutely would do it again.

If someone had given you a million dollars when you first started your business, what would you have done differently?

Brennan believes that if they had a million dollars right from the start, their learning experience would have been different. He expanded by saying that he doesn’t think that having a million dollars upfront would have necessarily made things better for them. Rather, it would have changed the game entirely for them this year. 

If they had that kind of funding, they would likely have invested it in developing artificial intelligence technology and probably hiring a second-in-command for Brennan sooner.

Additionally, they would have brought on another software engineer to assist them in building their products. 

Having only one developer creates certain challenges because they have to handle both the back-end and front-end development which slows down the process of gathering customer feedback and launching new products that cater to their needs.

Essentially, the cycle of building and improving products based on customer feedback would have been much longer which would, in turn, impact their ability to deliver cost-effective solutions to their customers.

What is your proudest accomplishment as an Entrepreneur?

The accomplishment that fills Brennan with the most pride was not a singular occurrence, but rather a series of happenings in October of last year when his business had probably the greatest week that any startup of their stage could have. 

In this week, Go Charlie.Ai was mentioned in the Wall Street Journal as a Generative AI company to watch. They were also accepted to be on a billboard for free in Times Square which was followed by their revenue, doubling and tripling in the days that followed. 

To be specific, Brennan’s proudest entrepreneurial moment was when his mom looked upon his company’s billboard in Times Square with tears in her eyes. Savings customers’ money is always great, Brennan clarified, but they’re just something incredibly special about seeing tears of joy in your mother’s eyes.

What big goals are you looking to achieve?

In terms of ambitions, Brennan has set his sights on reaching one million users. He sees this milestone as a significant accomplishment that shows genuine interest and engagement from a substantial user base. 

Another aspiration Brennan shared is providing a memorable experience for his team by organizing a trip to Greece at the end of July. With two of his co-founders being Greek, this opportunity to travel together will be a testament to their success as well as an opportunity to bond. 

Lastly, Brennan expresses his ambition to release a multimodal model, showcasing the team’s expertise and innovation. As a small four-person startup building advanced technology, this achievement would signify that they have made the right bets and investments in their team’s capabilities within the industry.

For those in the tech industry, working with AI, or simply looking to start their own business: Brennan has a whole host of invaluable wisdom to share. 

Are you an entrepreneur with your own wisdom and stories to share? Get in touch with us, we’d love to share it with you!