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Ramon Ray of Smart Hustle Media: “INSPIRE WITH ENERGY”

INSPIRE WITH ENERGY. Be sure to have an engaging and relatable host to keep the energy up. An emcee, event host or moderator must keep things lively, transition speakers and engage the audience. You might have a relatively boring or not so engaging speaker but having a great host can help uplift the entire event. […]

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INSPIRE WITH ENERGY. Be sure to have an engaging and relatable host to keep the energy up. An emcee, event host or moderator must keep things lively, transition speakers and engage the audience. You might have a relatively boring or not so engaging speaker but having a great host can help uplift the entire event. To host a virtual event requires a different skill set than an in-person event. Either way, I am having fun and so do the attendees and speakers who are providing content.


As a part of our series about “5 Things You Need To Know To Successfully Run a Live Virtual Event”, I had the pleasure of interviewing Ramon Ray, founder of Smart Hustle Media.

As the founder of Smart Hustle media, Ramon Ray inspires and educates small business owners how to grow their small business through events, interviews, podcasts, and online content. The author of four books, including “Celebrity CEO,” about building a community and personal brand, Ramon, is the real deal. Over his extensive career, Ramon has created four businesses and sold two, written thousands of articles, spoken to thousands of business owners, and impacted hundreds of thousands of small business owners and entrepreneurs to help their businesses grow. His clients, many of the world’s leading global brands such as Verizon, NetSuite, Dell, Microsoft, and others hire Ramon for his ability to humanize their brand within the small business space. Attendees of Ramon’s presentations, both in-person and virtual, consistently rate Ramon as one of the most inspiring and motivational speakers they’ve heard. Ramon has shared the stage with Seth Godin, Daymond John, Guy Kawasaki, Simon Sinek, Gary Vaynerchuk, and others. He has interviewed President Obama and joined Ivanka Trump at the Global Entrepreneurship Summit in India. During COVID, Ramon turned his focus to providing small business owners and large brands content through virtual events. From his five-hour Survive and Thrive Conference to his most recent Ramon’s Big Holiday Party, a three-hour event with sponsors such as Microsoft and Zoho, audiences are engaged and wanting more.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a bit about your “childhood backstory”?

I am originally from Ohio. Growing up, I was the kid who needed to understand how and why things worked and know everything about the people who created them. As a child I lit a wall of our house on fire, made a shortwave radio from a Radio Shack electronics kit, and took apart my “talking Teddy Bear” to figure out how it worked. From a young age, I had a technical inquisitiveness and a fierce love of reading. Today, my inquisitive nature has developed into wanting to learn more about the people changing the world and the products and services they are creating. I love people and community, so building a community of passionate people is something I have always gravitated towards.

Can you tell us the story of what led you to this particular career path?

From an early age, I found an interest in the online world. First, it was the Microsoft Flight Simulator, then Prodigy, and then quickly AOL. After that, I discovered even more of the Internet and fell in love with website creation and more. As I got older, I started a blog called SmallBizTechnology.com, which I sold last year. This blog focused on technology for small business owners, and was created to help “regular” small business owners — those who are not technically savvy — learn about what technology they need to boost productivity, save time, save time, increase revenue and boost customer service in their business. While blogging was not popular at the time, this gave me my first taste of the online world and the type of information business owners were looking for. At the same time, I was speaking for free, at local chamber events and associations. As my blog and speaking events grew, Black Enterprise and other publications started to reach out to me to write for them.

Nigel Burton who is now the CEO of Realmax Inc. was Microsoft’s General Manager of Small Business Products, including MSN, and bCentral. Nigel gave me my first interview and other high profile business leaders followed suit. Smallbiztechnology.com grew from a small blog for a community to a media company that educated growing businesses with information on how to strategically use technology as a tool to grow their businesses. I soon learned that while I was educating others through content and events, I was also inspiring them. This early aspect of “tech” and “speaking” gave me the initial steps to be who I am today.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I was at a media event where Bill Gates (founder of Microsoft) and Ted Wait (founder of Gateway Computers) were there to brief the media. I tried to slip Mr. Gates, a handwritten note asking to interview him, however his “handler” took the note and threw it away. I didn’t get the interview, but I also didn’t get discouraged.

So I did it again. In the early 2000’s, I was at CES, the most influential tech event in the world, owned and produced by the Consumer Technology Association (CTA), and didn’t realize that the media was waiting in the back of the room for Michael Dell to speak or that there was protocol. After his speech, I stood up in front of thousands of people, and asked him some questions. He looked at me, albeit nicely and walked away. Granted it was my mistake not realizing the nuances of that environment, but the lesson to these stories is continue to ask questions as no does not mean never.

Microsoft and Dell became my clients and have been for the past 20 years. In fact, I was asked to open for Michael Dell at the launch of Dell’s new Vostro line of computers for small businesses and have worked with them consistently over the years. These businesses and many others, partner with me as not only do I bring enthusiasm and energy to an event, I also help humanize the brand for others.

To many business owners, brands such Microsoft, Dell and Verizon are large global brands. They may not feel brands of this size, understand the smaller business owner. When I am involved, I help show a business owner that these large global brands understand the plight of the small business owner and they create products and services with them in mind.

When I think about why these businesses hire me, I think back to these instances and what I have learned since then. Today, those big brands I once sought to work with, now come to see how we can work together. I’m blessed, honored and very passionate about what I do and those around me.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I’m a HUGE fan of Seth Godin and love his overall style of always being a storyteller. In addition to launching one of the most popular blogs in the world, he has written 19 best-selling books, including The Dip, Linchpin, Purple Cow, Tribes, and What To Do When It’s Your Turn (And It’s Always Your Turn). Though renowned for his writing and speaking, Seth also founded two companies, Squidoo and Yoyodyne (acquired by Yahoo!). By focusing on everything from effective marketing and leadership, to the spread of ideas, Seth has been able to motivate and inspire countless people around the world.

In 2018, I asked Seth to speak at the 13th Annual Smart Hustle Conference. I watched the room soak up every word and watched him be present for every question. Seth’s latest venture Akimbo is transforming how entrepreneurs, freelancers, creatives, bootstrappers, etc. learn. The Akimbo Workshops are proven, powerful and efficient online communities that help people learn to see. In 2020, I partnered with Akimbo to present the Small Business Essentials Workshop. The experience really reinforced the influence of Seth and also resonated how my content and understanding of small business and the importance of building a community resonates with so many. I learned alot about myself and the students in my workshop. In some ways, it was different from what I had done in the past and in others a natural fit. This is what I look to do for my community, event attendees and the businesses I work with.

Dave Ramsey’s Entre Leadership is another favorite of mine, and is absolutely important for business success. If you don’t know the book, it is filled with everything you ever wanted to know about building and growing a business. So many business owners focus on just the mechanics of their businesses, however, they don’t focus enough on what it means to bring together a team and inspire others. I admire that EntreLeadership brings together business success with a focus on business leadership.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I am not a quote guy but if I had to choose, “Life is a journey,” would be my quote as it keeps me grounded. I feel that life is a constant JOURNEY that is filled with a marathon of new opportunities, people, and serendipity.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. For the benefit of our readers, can you tell us a bit about your experience organizing events in general?

For almost two decades, I’ve been bringing people together via events so they can learn how to grow their business from business leaders who have been in their shoes. Whether I am producing my own events for small business owners or speaking at other’s events, I am naturally inspiring small business owners who want to grow their business by giving them the energy and confidence to step outside their comfort zone.

I have brought thousands of people together through my events. I have produced events including the Small Business Summit and Small Business Influencer Awards to the most recent Smart Hustle Small Biz Summit and Survive and Thrive Summits. I have co-hosted events such as the Wix Small Business Breakfast and have spoken at SXSW, New Media Expo (BlogWorld), Inc 500, OPEN Forum at CES with Guy Kawasaki, Black Enterprise Entrepreneurs Summit, SCORE eBusiness, the United States Small Business Administration “Strategies for Succeeding in Business”, PC Expo, Internet World, SMB Nation and many more. In 2006, I sold the Small Business Summit conference series to Blog World and realized while I would still be creating events, my vision was larger. I wanted to create communities and my events would reside within them.

In doing this, I have created Smart Hustle Nation, a community of entrepreneurs, business owners and businesses, Everyday I am grateful for what I learned and created at smallbiztechnology.com and all that has transpired after. I love to learn, inspire and teach. Smart Hustle allows me to do that everyday.

Can you tell us a bit about your experience organizing live virtual events? Can you share any interesting stories about them?

I’ve been speaking at online and in-person events for years. I love the use of video and have used it in different forms throughout the years. When the coronavirus pandemic hit in March, it put a grinding halt to physical conferences and events. My life on the road stopped and I realized I needed to find a workaround and create virtual conferences for attendees around the world.

The Survive and Thrive Summit held on April 23, 2020 was the first virtual event I created during the pandemic. The event brought leading brands, experts and entrepreneurs, together to address the challenges brought on by the pandemic. Dell, AT&T, Salesforce, FreshBooks, Yelp, and SCORE along with other experts participated in this multi-hour online conference. Thousands of attendees not only signed up, but showed up. They stayed, chatted and participated. I reached out and surveyed attendees and speakers for feedback. They said they joined and intended to stay for only the first few minutes, but it was so captivating and exciting that they stayed for much longer. It was fast moving and never boring. This reinforced to me that while in person events are vital, virtual conferences are not going away, and they need to be engaging.

In your opinion, what is an example of a company that has done a fantastic job creating live virtual events? What specifically impresses you? What can one do to replicate that?

The ASBDC (America’s Small Business Development Centers) produced a very effective hybrid virtual event. I served as host alongside their president Charles “Tee” Rowe at a hotel and live-streamed the event to thousands around the country. At this three hour virtual conference, the live program included many compelling speakers, special guests and giveaways. Daymond John was one of the key speakers. Needing no introduction in the business world, the Shark Tank star proved why he is a highly sought after branding expert, consultant, author and speaker.

In addition to the live program, ASBDC offered over 100 on-demand, high-quality professional development workshops that were also accessible online. These course offerings were geared towards providing training on the new realities and uncertainties that SBDC advisers and their clients are facing. Some of the workshops discussed marketing, analytics, research, and consulting. I believe the ASBDC, looked at their audience and provided the tools for their members to grow and develop their centers. They created numerous ways to engage and invited their audience to have access to the content for an extended period of time. I have been working with ASBDC for years and found this event really fun to work on with them.

What are the common mistakes you have seen people make when they try to run a live virtual event? What can be done to avoid those errors?

Lack of preparation is one big problem. People think a GOOD live event is just throwing up a Zoom link. This is not the case. To run a live virtual event, you need to prepare. You need professionals to help you produce a quality event where people will want to stay and want to attend again. You need a solid agenda, great speakers with formidable content and meaningful visuals, quality audio and a solid internet connection complimenting the content. It’s also vital that you have help transitioning between speakers and agenda components.

To avoid these errors, I always work with an experienced online event producer who has experience with successful events. These professionals do not need to be expensive or fancy, but their experience is key. Also, be very clear on your goals and objectives for the event. YOU as the organizer, should invest the time to attend other events and ensure you and/or the speakers have good lighting and audio and backgrounds. I am a very open event producer. I ask various members of my team for their thoughts and ideas. I may not always take them, but it’s vital to know what others think.

Which virtual platform have you found to be most effective to be able to bring everyone together virtually?

There’s so many great virtual platforms that work well. Microsoft Teams has an amazing “large event” capacity. Streamyard is also great for doing a quality event on the more economical end of the spectrum. Other event services include Verizon BlueJeans. There’s also many event hosting platforms, HopIn, which recently bought Streamyard, is an example of one that helps with attendee registration and speaker and agenda organization. I have used them all, as they all have different purposes. Test everything out and see what works for your event needs.

Are there any essential tools or software that you think an event organizer needs to know about?

There are so many online event platforms BUT the most important tools an event producer needs to understand is the importance of good lighting, quality audio and a solid internet connection. Without that, your attendees are not focusing on you and your content.

An online event has different dynamics than an in-person event. I am an expert in hosting both online and virtual events — two different levels of “mojo” are needed. Having a variety of speakers who can clearly communicate and are not boring, is really important. Someone may be great in person but not very engaging virtually.

Ok. Thank you for all that. (Here is the main question of our discussion.?) An in-person event can have a certain electricity or energy. How do you create an engaging and memorable event when everyone is separated and in their own homes? What are the “Five Things You Need To Know To Successfully Run a Live Virtual Event” and why? (Please share a story or example for each.)

  1. INSPIRE WITH ENERGY. Be sure to have an engaging and relatable host to keep the energy up. An emcee, event host or moderator must keep things lively, transition speakers and engage the audience. You might have a relatively boring or not so engaging speaker but having a great host can help uplift the entire event. To host a virtual event requires a different skill set than an in-person event. Either way, I am having fun and so do the attendees and speakers who are providing content.
  2. PRODUCTION VALUE IS KEY: The video experience is a fundamental part of a successful event. You must be professional as the days of being sloppy are over. Make sure your speakers have good lighting and microphones, have well-considered backdrops and know how to look at the camera lens and not the screen. Be sure your speakers are experienced and know how to avoid shadows, reflective glasses or distracting clothing. Make sure your guests’ mics are set to be muted when appropriate. Lastly, be sure to use technology that enables you to have their names in the lower third. These small differences will uplift the entire event.
  3. THE AUDIENCE MUST BE PART OF THE ACTION: Engage your audience so that they are active members of the event. Use the chat function liberally. Ask questions, Don’t create a situation where people are simply staring at a screen — get them involved — using the chat function is one way to do that. The SmartHustle community or members of SmartHustle Nation are experienced business owners who don’t have a lot of time. If they are choosing to spend even a moment at an event I am part of, I must give them the ability to participate and be engaged. Nothing is worse than wasted time.
  4. FLOW AND RUN OF SHOW MATTERS:Rehearse the event as though you were live and in person. Follow your scripts and run time. Break up the agenda. ONE long boring event is “deadly” people will drop off so fast. Have short components with engaging speakers.
  5. PEOPLE LIKE THINGS: People like receiving things. When I host an event, whether they are receiving a signed book, tactics to grow their business or my favorite socks, it’s important that my audience receives something meaningful. They need more than one “thing” to take away from the experience.In December, I hosted a holiday party for three hours. I gave away my books, socks, and a DELL computer. Half way through the event, I was getting emails from other speakers offering up their services. I didn’t ask, but they were having fun watching my attendees get excited about winning things. While the winner of the DELL computer was so happyFINAF, the winners of the socks and books were equally excited. They felt included and saw the benefit of spending time at my event.

Let’s imagine that someone reading this interview has an idea for a live virtual event that they would like to develop. What are the first few steps that you would recommend that they take?

The first steps you should take when thinking of hosting your live virtual event is take a pen and paper and map out the FLOW of the event, noting the experience you want people to FEEL before AND after the event is over. This is the mission and vision of your event. It’s critical. Everything is then developed from this first step.

Super. We are nearly done. Here are our final questions. You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I’d love to inspire a movement called, “I’ll Wear Your Shoes,”and just purchased the URL. This is where we have open dialog with people we disagree with, LISTEN to their point of view, consider how they feel, how they grew up, and what they’ve experienced in life, to give us a perspective of THEIR view of life. I strongly believe in empathy and always try to wear other’s shoes, hoping they will try to wear mine. There are a few people who I work with who I know will always “wear my shoes” when we discuss uncomfortable topics. I hope that this movement will develop as time goes by and become second nature for so many.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

I would love to have a private lunch or breakfast with the Senior Vice President of programming at CNBC, CNN, ABC, NBC, Fox, etc.. I would love to learn more about the type of experts they look to work with. And of course, I would like them to consider having me host a new show about small business. Another person would be Tyler Perry. I appreciate the opportunity to interview him and see how I could possibly help him and add value to his world!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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