From Stage Fright In High School To A 6 Figure Global Speaking Business

During my sophomore year at Newton South High School, when I was sixteen years old, I was tasked with memorizing a speech on the topic of “affirmative action” and then presenting it to my English class. At my High School, every student is required to give a presentation on a topic of their choice as long as it was approved by the teacher. As an introvert, I was never comfortable speaking in front of any audience size and was sick to my stomach the night before I had to give my speech to a mere twenty-five students. The fear came from a lack of confidence, experience, introversion and that I would be in a position where I could receive a lot of harsh criticism by my peer group. In high school, everyone wanted to fit into social cliques, whereas when you grow up it’s more about discovering who you are and standing out from the crowd. Reflecting back, I remember that I chose the topic of “affirmative action” not because it affected me directly but only on the basis that it was a hot topic in the media back then.

While I remember my speech receiving a passing grade, I avoided any future presentation opportunities because it didn’t come natural to me and so I was uncomfortable with the process. I wouldn’t say that I feared public speaking more than death as most people do in America, but I was certainly afraid of the spotlight. While at EMC, my first job outside of college, I had some public speaking opportunities that seemed to be less painful because I was a subject matter expert on social media and Internet marketing, which gave me confidence in front of an audience.

It wasn’t until I started publishing career advice articles online, when I felt right at home. I used to write ten to twelve articles each week outside of my full-time job at EMC out my passion for helping my generation succeed. The more I read, wrote and experienced, the more excitement I had about getting the word out in new ways. One of my early outlets for helping Millennials with their careers was speaking at colleges in and around Boston. Since I had no track record as a recent college graduate, I landed my first speaking opportunity at Bentley College (now University), my alma mater. I spoke to the Bentley Marketing Association, a student run organization that I used to be on the board of as a junior. While most students who return to speak at colleges do it for fun, I took the opportunity very seriously. I made sure it was filmed (clip here) and I asked for a testimonial from the head of career services to be used as part of my marketing to get future speeches. I still get the chills when I watch my first speech on YouTube and it will remain there to remind me of how far I’ve come, and what’s possible with hard work.

After my first presentation, I tweaked the content based on the feedback, and updated it with new fresh material. From there, I emailed every head of career services at colleges such as Tufts University, Boston College, MIT, Harvard and Emerson. I was given an opportunity to speak at all of these colleges and more, which I’m thankful for now because I was able to practice my presentation, connect with students and build the foundation for a future speaking career. With every speech, I naturally became more confident in my abilities and would continue to build my portfolio showcasing the value I brought to college students.

After publishing my first book, Me 2.0, as well as achieving success with my blog, magazine and other businesses, I was ready to take my speaking career to the next level by turning my hobby into a profession. I had no idea how to actually make money speaking since all of my gigs were pro bono! I asked my fellow speaking community how to actually get paid to speak and they unanimously said that I needed agent representation. I reached out to speakers bureau’s but none would represent me because I wasn’t already making money speaking, a catch 22 that is similar in the publishing world too.

I went back to the drawing board and spoke again at Bentley for no fee. Little did I know that my now close friend Amanda Healy was in the audience this time around. While she didn’t come up to me after my presentation, I received an email when she graduated. She got a marketing job at CA, formerly Computer Associates, and they were looking for a keynote speaker on the topic of “personal branding” because the speaker they originally hired backed out last minute. Of course I agreed but I made one aggressive move that changed my career. I handed the speaking opportunity over to an agency that negotiated a fee of $6,000 with all expenses paid. I couldn’t believe that it was even possible to receive that much money to speak for an hour but it happened and I leveraged it to get representation in my mid-twenties. This taught me a very important lesson in life. Sometimes you need to speak for free for the future potential opportunity to get paid since you never know who in the audience could hire you at a different point in your life when they are in the right position to do so.

After I received a positive testimonial for speaking at CA, I started signing more clients like Time Warner and Symantec. This occurred because I had maintained a strong presence in the media focused on the topic of “personal branding”, which I had evangelized for my generation starting in 2007. I started gaining credibility by speaking at major companies, confidence from continuously speaking and new contacts that supported me later in life.

After several years, I decided to change topics and focus on Millennials in the workplace since I was inspired to become a leader and supporter of my generation throughout their career lifecycle (a mission that you’ll see at the top of this website). One of my interns back then ended up interning at American Program Bureau, one of the largest speaking bureau’s that rejected me when one of their current speakers tried to bring me in. She was working directly under Josh White, who is younger than me and is now the head of sales. There’s not enough space in this article to describe how valuable and supportive Josh has been in my speaking career. I call him “the super agent” or “a kind version of Ari Gold from Entourage” when I describe him to others. We had dinner in Boston’s North End and I told him about my ambitions and he immediately latched onto them and signed me.

From there, I started speaking at major conferences, larger companies and now globally, which I couldn’t have even dreamed of when I first started. My fees kept going up and the audience size also grew, yet it didn’t make me more nervous because I had so much preparation. Last year, I was one of three American speakers to present at Brazil’s book festival. My face was on a billboard and the Portuguese edition of my second book, Promote Yourself, was right next to me. It really made me appreciate where I’ve been and I felt like anything was possible once the event was over.

This past September was not only a major milestone but it was a true breaking point for me in my life. It was my one hundredth speaking gig and I was asked to fill in for another speaker at The CEO Talent Summit in Dallas. It wasn’t a major milestone in audience size but it was one in terms of who was in the audience. There were CEOs of major companies like Deloitte, JC Penny and Rackspace, as well as billionaires like Ken Fisher. I rose to the occasion and delivered the best presentation of my career and was even rated higher than one of my mentors, Dan Pink (I had the advantage because he had to speak in a barn while CEOs were chowing down on world class Dallas BBQ food!). My presentation was different than usual as I had told stories on the spot and made jokes naturally without hesitation. I felt so comfortable in front of this high profile crowd that I truly believe you could throw anyone in front of me and I wouldn’t get nervous now. What’s even more fascinating is that this event gave me more confidence in my personal life and I’m much more spontaneous and open than I’ve ever been.

Most recently, a truly remarkable thing happened. Back in 2013, right before Promote Yourself came out, I spoke to one thousand people at The SHRM Annual Conference in Chicago. I submitted this year to speak again and received an email a few weeks ago notifying me that they accepted my application. I checked the website and it turns out that they put me in a “MEGA SESSION”, which means I’ll be speaking to about 3,500 in one room come next June in Washington DC. This tells me that I received good feedback from my presentation in 2013 and that my topic of “Millennial leadership” was big enough for this size session. I’m still in awe of how far I’ve come with my speaking career and appreciate each agent, each company, each school, and every conference organizer that gave a shy introvert from Newton, Massachusetts a chance.

My Top 4 Pieces of Advice For Future Speakers

1. Pick a topic you’re passionate about. As you read earlier in my story, I wasn’t passionate about the topic of “affirmative action” in high school so I wasn’t excited to talk about it in front of a class. When I started talking about the workplace, careers, personal branding and Millennials, it was much easier for me because I had a message and the right audience to communicate it to. When you’re passionate about a topic, you naturally want to become an expert in it and when you’re an expert, you naturally become confident – it’s not forced!

2. Practice makes perfect. It might sound cliche but we all start off as beginners in our own professions until we practice enough to become better. The more presentations I gave, the easier speaking became. I kept asking for feedback after my presentations and incorporated that feedback into future presentations. The more I spoke, the easier it became and when I had larger audiences, or ones where the audience was more high level (executives), it compounded. Even the greatest basketball players in the world, like Michael Jordan, had to practice everyday in order to achieve their iconic status (even with natural talent).

3. Emulate speakers you respect. I find that the more you watch other people speak, the more you can emulate them and become better at your own craft. Aside from sitting in on the presentations of some of the best speakers at conferences I was also speaking at, I would watch YouTube clips constantly. For instance, some of the speakers that I try to emulate are Tom Peters, Marcus Buckingham, and Dan Pink. The more you watch them, the more you can pick up on their hand gestures, eye contact, presence and content delivery. A few common practices you can gather from their presentations are that they tell stories, make the audience laugh, use data and are outspoken on the topics they care about.

4. Become a great marketer. I once asked my agent what conference organizers were looking for when hiring a speaker and he told me what’s most important in the following order: 1) Name recognition 2) Topic relevancy 3) Quality of speaker. If you aren’t getting your name out there, then they won’t find you and you won’t get hired. Furthermore, if you want to get paid the “big money”, then your name has to be able to sell tickets for conferences or they won’t be able to justify hiring you. My advice is to speak for free in order to build a video reel, gather testimonials and become a better speaker, while producing content online around a relevant topic. This way, you are building the assets required to be a paid speaker, while getting your name out into the public so conference organizers can find you.