Interested in starting your own entrepreneurial journey in personal and business development but unsure what to expect? Then read up on our interview with Milo Shapiro, Owner of IMPROVentures and Public Dynamics, located in San Diego, CA, USA.

What's your business, and who are your customers?

Anyone who wants to feel more "Prepared, Polished, and Powerful" when they speak, whether it's a big one-time speech, a program you repeatedly give (like a sales pitch), or someone who gives a different update to their staff weekly...finding comfort and ease in presenting is a learnable skill, and it's way more approachable and fun in coaching than a class setting.

Tell us about yourself

In 2000, after 15 years of computer programming and system analysis, I took a huge leap from the safety of that realm into the world of my passion: sharing the power & lessons of improvisation in the business world. I had seen in my improv classes over the previous ten years how the lessons carried over into everyone’s lives. For me, it made me a creative programmer who could listen better to my clients and negotiate better solutions. At heart, I always was an improviser. Walking away from the security of my last job was probably the most difficult choice of my life, but I’d had too many people tell me that I was missing my calling, and I knew it was true. The time had come to turn my passion for improv and its value into a career.

Initially, my focus was to go back into organizations (having worked within them for so long) to use the power of improv games to convey crucial teamwork skills, like listening, building upon the ideas of others, and creative problem-solving. The result was the TEAMprovising™ course that I’ve been leading ever since, from tiny organizations where all staff attend to sections of large organizations like Southwest Airlines, Union Bank, and the US Navy. So now I was a team builder.

After a couple of years of leading TEAMprovising™, people kept saying, “This is powerful stuff! It’s changing our work environment. It’s even changing how I work with my spouse and my kids. You need to get out and speak to larger groups!” I found the idea intriguing, having done Toastmasters for many years, so I began studying through the National Speakers Association and knew I wanted to speak professionally… eventually.

But life threw me an unexpected twist: In early 2002, I was asked to lead a crowd of professional speakers in some improv games to warm them up for the big multi-speaker event to come. I was nervous about a big crowd, but I agreed. When I stepped onto the stage, the cameraman yelled out, “Remember everyone, no talking for the whole twelve minutes he’s on stage and keep your eyes on him the whole time!” I couldn’t lead them in games like that…and I was already on the stage! So I took a deep breath and made up a 12-minute speech about my life as an improviser…on the spot. I have no idea what I said now, but I remember someone came up to me at the break and asked if I would speak at her Rotary club the next week. And the rest, as they say, is history…leading to years of solo speeches for groups like the Department of Defense, Qualcomm, and Minolta. So now I was a professional speaker.

In late 2002, an improviser that I knew was asked to give a speech at a conference. He wanted to do improv to make business points stick, as I do in TEAMprovising. I explained to him that we’d need to do more than just perform. It would have to have a speech format with games within it. The result: The IMPROVfessionals with our Top Ten Countdowns. Together, we found ten games that lent themselves to ten valid points about management and teamwork.

After speaking briefly about our expertise on each point, we performed the game to prove what we meant. “Whose Line Manager Is It Anyway?” was an instant hit, and we later booked it for Pfizer, Kodak, and others. By changing the topic a little, we developed lists on Sales, Event Planning, and more, just titling these other programs “Laugh In The Fast Lane.” We found that attendees liked the fun management liked the fact it wasn’t JUST fun…there were business lessons in the program that hit home. And I loved that I was blending the entertainer in me with something that would make a difference to the audience. So now I was a professional entertainer.

A number of other speakers began asking me for pointers, which I was flattered to offer, but then something bizarre started to happen: conference attendees started lingering afterward to ask if I would coach them! I’d always gotten high praise for my evaluations in Toastmasters, but I’d never considered it a possible career direction. I approached it cautiously at first, but the growth my new clientele experienced was quickly evident. They kept sharing the excitement in not only conquering fears but discovering stronger results and more interested audiences. I found that coaching in public speaking was something that not only suited me but greatly satisfied me as well — to have such a direct impact on someone’s life and job satisfaction in this area.

Since then, I’ve worked with hundreds of people, including CEOs, business presidents, salespeople, middle managers, authors…even beauty pageant contestants and unemployed job applicants. I’m so proud of the testimonials on this site from these people — and proud of their growth as well. Along the way, I’ve done some duo, trio, and small class training as well, but the one-on-one is still my favorite way. So now I was a speaking coach.

Not surprisingly, clients asked if there were books I could recommend, so I began reading what was out there. Repeatedly, I came to the same conclusion: “I’m bored!” This was a topic I loved, but the books I was finding weren’t any fun to read. The message was clear: Write a book on public speaking from the perspective of someone who speaks professionally, has both an improv and a business background, and has watched a LOT of amateurs and professionals both fail and succeed. The results? “Public Speaking: Get A’s, Not Zzzzzzz’s!” and its sequel, designed specifically for teens.

So now I was an author, too. In fact, since then, I’ve written a fun book of true-life short stories with life lessons (hey, you can only use so many in your speeches) called “The Worst Days Make The BEST Stories…and Other Life Lessons.” I also have a humor book…sort of a novel, but different…that I hope to have available before long. What’s next? I keep thinking, “This is enough!” but life has a way of continuing to surprise me, so who knows?

What's your biggest accomplishment as a business owner?

That 22 years later, and through the Great Recession and COVID killing the speaking business, I'm STILL in business! But to answer it differently, the fact that nothing can take away from the hundreds (thousands if you count keynote audiences) who are more successful and confident in their speaking because of me.

What's one of the hardest things that come with being a business owner?

Feeling like you're never doing enough...or missing the right boat. There's always some opportunity, some avenue, some consultant, some website tweak that could be the golden ticket. But you can't do everything.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. You better LOOOOOOOOOOOOOOOVE it. Because it's gonna be your world now. All the time.
  2. Fail. Seeking perfection will undermine solid B's and great learning on the way to A's.
  3. Be bold. No one remembers someone who softly does what everyone else does.

Is there anything else you'd like to share?

There's a horrible misconception that if you know English and you know your topic, you SHOULD be ready to go speak about it. But there are like 15-20 other steps in between. So people try, fail, and don't want to do it again. Or they go to a class, relieved that they only get 3% of the teacher's attention and don't really improve. We didn't learn to do almost anything else in life while 25 people stared at us. Why do we think we should learn presentation skills that way? Coaching makes the experience all about you, and the learning curve drops tremendously while the effects are astounding.

Where can people find you and your business?

Website: https://miloshapiro.com/
LinkedIn: https://www.linkedin.com/in/MotivationalSpeakerMiloShapiro/

If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

Turn your craft into recurring revenue with Subkit. Start your subscription offering in minutes and supercharge it with growth levers. Get early access here.