Cultivating the Entrepreneur Within: From Candy Trades to AI-Powered Newsletters

We often hear tales of small businesses becoming billion-dollar empires overnight. In reality, most entrepreneurial journeys are marathons, not sprints. In fact, they’re built on countless small steps, each representing a lesson learned and a skill honed.

Imagine someone who sold candy in their childhood and used that entrepreneurial spirit to launch a thriving business specializing in AI-powered newsletters. Despite their differences, it encapsulates the spirit of entrepreneurship: spotting opportunities, adjusting to change, making connections, and looking forward.

It might sound like a fictional story, but it’s Joe Stolte’s real-life story.

As an entrepreneur with a proven track record (think Inc. 500 and five successful tech companies), Joe isn’t afraid to innovate. As CEO of Daily.ai, he has led exits like Lottery.com’s $526M IPO and GrowFlow’s $62.5M acquisition.

For busy thought leaders and brands, Daily.ai makes email marketing easier. With only five minutes a week, you can create newsletters with 40-60% open rates without writing a single word. Moreover, Daily.ai creates newsletters for philanthropists like Joe Polish and Peter Diamandis across 20 industries every week.

Even if you weren’t always an entrepreneur, Joe is here to share advice on how to find success by cultivating the entrepreneur within.

Developing an Entrepreneurial Drive from a Young Age

Early signs of entrepreneurial spirit are often seen in childhood. Joe’s journey exemplifies this. Joe’s story illustrates how relentless drive and resourcefulness define successful entrepreneurs, from trading candy for lunch items to mowing lawns to buy the things he wanted. 

In addition to achieving financial success, his journey involves learning, growing, and turning failures into stepping stones.

Persistence: The Fuel for Every Dream

As Joe knows all too well, success is rarely a smooth ride. However, his motto is “Never give up.” 

According to him, about one out of every twenty individuals chooses to become entrepreneurs. Navigating the inevitable challenges requires a unique combination of resourcefulness, grit, and unwavering persistence.

Learning from the Ashes: Rallysong and Beyond

Like any entrepreneur, Joe has faced setbacks. For example, one of his first startups, Rallysong, ultimately failed due to obstacles. 

Despite this, Joe doesn’t shy away from failure. It provided him with valuable insight into raising capital, particularly the intricacies of the process. As a result, this knowledge becomes a stepping stone for future endeavors.

From Startup Grind to Corporate Climb: Lessons from the Trenches

Joe’s journey doesn’t follow a straight line. During his career, he has gained valuable experience working at established companies such as Lottery.com. Despite this, his desire to create and build his own vision remained. When his long-term goals weren’t aligned with his corporate position, he wasn’t afraid to leave.

As a result of this spirit of exploration, he was appointed Chief Revenue Officer at a rapidly growing company. During his tenure as CEO, the company grew from $900,000 to $8 million in annual recurring revenue. In the end, Joe’s skills and leadership led the company to be acquired for a remarkable $62.5 million.

Having the Guts to Say, “This Isn’t for Me” and Pivot

Joe emphasizes the importance of being courageous, saying, “This isn’t for me,” and pivoting as necessary. It is important to recognize when a situation is not right in order to achieve long-term success and fulfillment. 

As he navigates the complexities of his career, Joe attributes his success to his mentors’ guidance and his faith.

Innovating in AI Before the Era of ChatGPT

Today, Joe Stolte is CEO of Daily.ai, a company that builds high-performance email newsletters for small businesses and thought leaders. During his time selling GrowFlow, a compliance software product, he identified a significant gap in the market. 

During his time with GrowFlow, Joe saw firsthand the challenges small businesses faced when creating engaging email marketing content. As AI tools for content creation emerged, he noticed that they often failed to deliver the results businesses needed, such as opens, clicks, leads, and sales. To address these needs effectively, Joe developed Daily.ai, which combines AI with human expertise.

The Daily.ai Solution: AI + Human Expertise

Daily.ai curates high-quality content from trusted sources by combining AI technology with human expertise. Each subscriber’s content is then personalized to ensure relevance and engagement. Unlike other AI tools, Daily.ai provides “future-forward positive content” that avoids clickbait and negative news. As a result, this strategy not only engages audiences but also builds a positive image of the brand.

The Perspective Engine: Where Data Meets Personalization

With its proprietary “Perspective Engine,” Daily.ai goes beyond simple demographics to understand subscriber behavior and preferences. In addition to ensuring seamless alignment with brand voice, data-driven content ensures industry-leading open rates. 

I can vouch for this myself. The open rate for Lifestyle Investor Insider is impressive, with a 65-70% open rate, proving Daily.ai’s effectiveness.

Beyond the AI Algorithm: The Human Touch

Even in the age of artificial intelligence, Joe emphasizes the importance of human meaning-making. He mentions Dan Sullivan’s observation that people assign meaning to events, and Daily.ai empowers businesses to shape those meanings through positive content. Consequently, Daily.ai cultivates loyalty and engagement between businesses and their audiences.

Conclusion: Igniting the Entrepreneurial Spirit

An unwavering entrepreneurial spirit is the key to Joe Stolte’s success. He has gone from childhood barters to leading a company at the forefront of AI-powered marketing. His journey serves as a powerful reminder that anyone can cultivate the skills and courage needed to pursue their dreams. Keep in mind: never underestimate the power of persistence, and embrace learning from others.

Key Takeaways:

• Early hustle. From an early age, Joe showed entrepreneurial spirit, trading candy and mowing lawns to acquire what he wanted.
• Persistence is key. Entrepreneurship requires a “never-give-up” attitude, a crucial trait.
• Learning from failure. Despite the failure of his first startup, Rallysong, he learned valuable lessons about raising money.
• Corporate experience. Despite working for established companies like Lottery.com, Joe remained determined to build his own vision.
• Leadership & growth. In a short period of time, he led a company to explosive growth, resulting in a $62.5 million acquisition.
• Knowing when to pivot. Even if a situation seems successful, Joe emphasizes the importance of recognizing when it isn’t right for you.
• Innovation in AI. He identified a gap in email marketing – a need for engaging content that does not require a lot of effort to create. It led to the development of Daily.ai, a tool that uses artificial intelligence to deliver email newsletters.
• The perspective engine. With this technology, subscriber behavior and preferences are understood beyond demographics, ensuring industry-leading open rates.
• Human touch matters. By creating positive content, Daily.ai enables businesses to cultivate loyalty and engagement.

Featured Image Credit: cottonbro studio ; Pexels, Thank You!