The Key to Success in Business is Continuous Learning: Serial Entrepreneur Anthony Chiaravalloti on Building Multiple Businesses

Anthony Chiaravalloti
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Embarking on an entrepreneurial journey requires courage, determination, and a passion for creating something meaningful. In this interview, we sat down with Anthony Chiaravalloti, a 30-something entrepreneur in Toronto who made the leap into entrepreneurship at a pivotal moment in his career. 

With a passion for learning, an eye for emerging trends and a thirst for knowledge, Anthony has built multiple businesses, faced failures, and learned valuable lessons along the way. From his experiences, we gain insights into the challenges and rewards of entrepreneurship, the importance of continuous learning, the power of embracing content, and the inevitable impact of artificial intelligence on businesses and founders.

The decision to leap into entrepreneurship

While working at TD Bank for five years in his early 20s, Anthony thought banking would be his path in life. As a top sales producer in the quarter, he was invited to a presentation by investor and Dragon’s Den dragon Kevin O’Leary with a small group of TD Wealth advisors. As a recent university graduate, Anthony asked Kevin for advice for someone in his position. O’Leary told him that the fact that he was in the room is a good sign and that the bank would give him a good life — but his advice was that if he wanted to become truly wealthy and make a big impact, he should become an entrepreneur. Anthony took this advice seriously.

At this time, many companies were starting to adopt social media and digital media more and more, so Anthony saw an opportunity to be part of the digital revolution. That weekend, Anthony determined that before turning 30, he would like to be an entrepreneur — so he thought, “Why wait” and decided to start then, building while he was young.

Now at 31, he runs multiple businesses, including creative performance agency King Street Media and content house CreatorClub.

Entrepreneurial Failure and Learnings 

Anthony experienced his first failure in entrepreneurship with Cornucopia Labs, a retirement planning and mortgage application AI tool which Anthony self-funded and started from zero with a small team. While the market timing was right, they did not launch quickly enough.

“Starting a company that provides a new solution is an uphill battle because it requires educating your target audience on how your innovative product works and is needed — it’s not for the faint of heart,” Anthony shares, reflecting on his experience

The lesson from this experience is that launching quickly is key, as represented by this classic Reid Hoffman quote: “If you’re not embarrassed by the first version of your product, you’ve launched too late.”

Lifelong learner

In the third year of his studies at York University, Anthony took a motor learning course about how humans learn and master their crafts.The professor taught him that it takes anywhere from 8-12 years to master a craft.

“If you are 20 years old, you have the opportunity to master 4-6 crafts in your lifetime — however, too many people spend their life mastering one craft, or pivoting too often and not mastering anything.”

Learning this had Anthony determined to master multiple things throughout his life. 

Continuous learning while building

When asked about what he does to keep continuously learning while busy building his businesses, Anthony shared:

“I spend a ridiculous amount of money on coaches, personal trainers, therapists, teachers, courses and books,” Anthony shared, adding that he has invested over $2,500 in his Audible and physical book library alone.

Anthony’s advice for busy entrepreneurs is to spend 10 minutes a day learning — listen to audiobooks while cooking, cleaning and brushing your teeth; it adds up. 

“Spending money is a great motivator,” Anthony learned from a well known Warren Buffett concept, “if you pay a coach, trainer or teacher, you are more likely to see it through and do it.”

Entrepreneurship is worthwhile

According to Anthony, entrepreneurship is not worthwhile for 95% of the people in society.

“It’s stressful, mentally and physically painful, and requires sacrifices that have no guarantee of paying off. A lot of the time entrepreneurs don’t make more money than they would at a normal 9-5 full-time job — yet I still love it. There are other benefits besides just the money, that makes the ups and downs worth it.”

In entrepreneurship, like sports, you can try your absolute hardest and still fail. “That’s the sad truth that most people don’t tell you about getting into business,” Anthony shares.

The best part of being an entrepreneur

Anthony believes the best part of entrepreneurship is building a community of people you choose.

“Unlike when you get a job and are given a team to work with, in entrepreneurship you can build your own community of people — which includes clients and customers you serve, and the employees you hire and also serve as a leader.”

Anthony referenced the Steve Jobs Stanford commencement speech: “Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do.” 

Anthony believes that loving what you do comes down to who you do it with and who you do it for — and that being able to control that is the best part of entrepreneurship.

Running a marketing agency and a financial practice 

Through his days interning at startups, Anthony fell in love with working with entrepreneurs as “they’re generally passionate and interesting people”, so he wanted to find a way to work with entrepreneurs more often. “The best way to do this was to provide a service that helps entrepreneurs succeed”, Anthony shared, and that is why he launched his agency, King Street Media.

Anthony took the same approach with his financial consulting practice. The company started off serving a more broad clientele but evolved into fractional CFO consulting and corporate tax planning consulting practice for founders and businesses specifically. 

“Part of becoming an entrepreneur is freedom — yet many entrepreneurs become slaves to their company. My consulting practice is all about helping entrepreneurs structure their business so they can be free.”

Anthony shares that this starts with having a proper north star and goal-planning, setting up the right systems, putting the right people in the right place, having finances in order and then developing a scalable customer acquisition strategy.

Now is the time for brands and entrepreneurs to embrace content

As media platforms that sell advertising become more widely used, the cost of reaching an audience is increasing. If done well, it is now more cost-effective to create content and build a brand with fans to grow organically than it is to solely run ads.

“This, combined with the rise of the creator economy, is why my team and I built CreatorClub — making the content creation process easier for founders and marketing teams, saving them time and money,” Anthony explained.

What the AI revolution will mean for businesses and founders

While Anthony notes the AI revolution will start slow, he believes it will progressively start to be part of everything in life until “if you’re not using it, you’re not relevant anymore — just as we saw the adoption curve happen in the 90’s with the Internet, during the 2000s with cell phones, and during the 2010s with social media.” 

For today’s businesses that have not fully adopted social media, Anthony predicts that if they do not evolve and make the leap to AI, “they will continuously shrink, lose money and go out of business.”

Connect with Anthony 

Anthony Chiaravalloti on Linkedin

King Street Media — Creative Performance Agency

Podcast: What They Did Not Teach You in School — Spotify + YouTube

CreatorClub —


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