Antonio Calabrese – Founder & CEO of

Don’t wait, start now, move quick, fail often, and learn.

Antonio Calabrese is the Founder & CEO of, a platform that connects students with businesses on graphic & web design projects.

Antonio grew up in Rochester, NY, where he remained to pursue his business education from the Rochester Institute of Technology. Upon completing college, Antonio went into sales, working for smaller startups as well as larger organizations such as Groupon, all while starting other businesses on the side. Always having the entrepreneurial itch, Antonio decided to leave corporate sales life to pursue a full time freelance career helping businesses establish their online presence through website development and online marketing.

Two years into freelancing, Antonio thought back on the difficulties of gaining enough traction to provide a full time income on his own. This is when he decided to start Boonle to help beginning freelancers get started by finding relevant work in order to build a portfolio and fine tune skills.

Where did the idea for Boonle come from?

I left corporate life in 2012 to begin a freelancing career, knowingly taking a risk. Other than tinkering with some of my own projects and doing some work for a few one-off clients, I had little experience in web design. Like many new freelancers, the biggest challenge I faced was finding work. Potential clients wanted validation that I was able to successfully complete projects in ways that would help them achieve their goals. When you don’t have a strong portfolio to show, it becomes difficult to prove your worth.

I could have folded my hand and returned to corporate life. But like most freelancers, corporate isn’t what I strive to do, so I needed to find a way to develop a worthy portfolio. I began offering my time to friends, family, and nonprofits to gain additional experience and build a portfolio. Because of my mentality, I was able to quickly refine my skill set and begin marketing myself as a professional. And so Boonle was conceived. I wrote down in great detail my vision of how it would work, how users would interact, and ultimately, how it would help people. I surveyed as many people as I could to help validate the idea, and then I put a plan together to finally build what is now an online platform to connect students with businesses & nonprofits on graphic & web design projects.

What does your typical day look like and how do you make it productive?

Being an early stage startup means that wearing many hats becomes typical on a day-to-day basis. I always begin my day making sure that they are no outstanding support tickets or open conversations with current Boonle users. I then make sure to exercise for 30 – 60 minutes as this helps me focus for the long day ahead. Once I settle in for the day, I look into growth over the past day and week and immediately move to growing our user base. Every day requires me doing what I can to grow Boonle – whether it’s through email, phone calls, or advertising – growth is moving the needle forward.

How do you bring ideas to life?

I work and think through ideas on paper, then bounce my thoughts off of other people who know nothing about it. The original concept for Boonle is still in one of my notebooks and takes up about 3 pages, with details on the idea itself, user interactions, monetization, and more. The site launched with only very minor changes to the original idea.

What’s one trend that really excites you?

Artificial Intelligence. It both excites me and scares me.

What is one habit of yours that makes you more productive as an entrepreneur?

Waking up at 5:30am. I find that waking up early allows me to get a lot of work done while potential distractions are still asleep. If you’re working with others in different parts of the world, waking up early is a necessity in order to maintain efficiency and avoid delayed conversations.

What advice would you give your younger self?

Don’t wait, start now, move quick, fail often, and learn.

Tell us something that’s true that almost nobody agrees with you on?

Change is actually a good thing.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I write down my wins for the day right before bed, every day. This allows me to close out my day focusing on any success that I had and helps to keep mood on the upside. Focusing on what went wrong causes stress and stress can often lead to mistakes and negativity, both of which won’t help you move forward.

What is one strategy that has helped you grow your business? Please explain how.

Putting yourself out there. As scary or uncomfortable as it may seem at times, it’s necessary if you want to inflict change and see growth. Whether it’s meeting new people, giving speeches, creating blog or video content, calling a potential customer by phone – you get the idea. These often nerve-racking tasks can make all of the difference.

What is one failure you had as an entrepreneur, and how did you overcome it?

Getting the product wrong at launch and pressing the same idea for too long. To overcome it, I accepted that my original idea was not right for the market and immediately started collaborating with my team and current userbase to figure out what need to be changed in order to find product-market fit. Advice? Recognize failures early and move quickly to correct them.

What is one business idea that you’re willing to give away to our readers?

I haven’t completely thought this idea through, but a way to handle email “noise”. Sure, I can create filters, unsubscribe, etc., but there has to be a better solution. If there is something already developed, please let me know!

What is the best $100 you recently spent? What and why?

Books on Audible. As much as I’d like to read, I rarely finish reading physical books. With Audible, I’ve listened to more books in the past few months than I’ve actually read in the past 10 years.

What software and web services do you use? What do you love about them?

There are many, but my favorites include Intercom, Slack, and Google Drive. Intercom is an integral part of my business for user interaction, onboarding, and support. Slack helps me to communicate with my team, and Google Drive is used for storage, sharing, and managing content.

What is the one book that you recommend our community should read and why?

The Subtle Art of Not Giving a F**k by Mark Manson. Too often people are held back from doing things, pursuing ideas, or publishing content due to fear of rejection or what other people may think. This book (I listened to it through Audible) is short but engaging.

What is your favorite quote?

“Starting a company is like eating glass staring into the abyss of death. Um, if that sounds appealing, go ahead.” – Elon Musk

Key learnings:

  • Recognize failures and move quickly to recover
  • Don’t fear change.
  • Put yourself out there and get uncomfortable.


Boonle on Twitter:
Boonle on Twitter:
Antonio Calabrese on Twitter: @acalabrese83
Antonio Calabrese on Twitter: