Wing It and Win! Workshop
TAMPA PUBLIC WORKSHOP
Speak with confidence. Think on your feet. Connect with just about anyone.
The most fun personal development workshop in the world is back in Tampa!
Wing It & Win combines Improv-based games, practical insights from neuroscience, lively discussions, and plenty of actual practice. You’ll become more comfortable speaking up, responding in the moment, meeting new people, and trusting yourself when you don’t know exactly what to say.
No acting experience is needed. Nobody has to be funny. Nobody gets put on the spot.
Does Any of This Sound Familiar?
Maybe you’re naturally shy or quiet. Maybe you’re perfectly comfortable once you know people, but those first few minutes feel awkward.
Perhaps you own a business and want to be better at networking, speaking, interviewing, selling your ideas, or connecting with clients. Maybe you’re in Toastmasters and want to become more comfortable speaking without preparing every word in advance.
Or perhaps you’ve seen Toby speak somewhere, thought, “That looks both useful and ridiculous,” and decided you wanted more of it.
People come to Wing It & Win for different reasons. Most want to feel more confident, more connected, and less trapped inside their own heads when a conversation or situation does not go according to plan.
What Happens in the Workshop?
You’ll take part in short, structured Improv games and activities that help you practice listening, responding, adapting, remembering, and communicating without trying to plan everything beforehand.
We start simple and build gradually. Most activities happen in pairs, small groups, or with everyone participating together. You will not be dragged onto a stage, expected to perform, or asked to entertain the room.
There will be laughter. But nobody is the joke.
After many of the activities, we’ll talk briefly about what happened and how the same skills show up in conversations, meetings, presentations, networking, relationships, and ordinary moments when your brain suddenly decides it has never encountered another human being before.
People change by experiencing a different response under pressure, understanding what happened, and practicing it enough to use later. That is what we will be doing, although it feels considerably more fun than that sentence makes it sound.
What Will You Get Better At?
You’ll practice how to:
- Feel confident in almost any situation, even when you don’t know what will happen next.
- Talk more comfortably with individuals, small groups, or an entire room.
- Think on your feet without mentally rehearsing every possible answer.
- Listen and respond to what someone is actually saying.
- Access your memory in a different way, making names, ideas, and the words you need easier to find.
- Speak up, offer ideas, and commit fully instead of editing yourself into silence.
- Recover when you stumble, say the wrong thing, or temporarily lose your train of thought.
- Meet new people and have better conversations without feeling like you are “networking.”
You won’t suddenly become a different person. You’ll become more comfortable trusting the person you already are.
You Do Not Have to Be an Improvisor
You don’t need to be an actor, comedian, performer, or extrovert. You do not even need to want to become one.
Improv is simply the tool we use. The real skills are listening, connecting, responding, adapting, remembering, speaking confidently, and staying useful when you do not have a prepared answer.
Quiet people are welcome. Awkward people are welcome. Experienced speakers and business owners are welcome. People who are unsure whether they will be comfortable are especially welcome.
Why Toby?
I’ve taught Improv with the Bay Area Improv Theatre and at the Patel Conservatory at the Straz Center for the Performing Arts. I’ve also started businesses, worked for Fortune 500 companies, run a nonprofit theater group, and spent years helping people communicate, collaborate, present, and think on their feet.
I understand how these skills can help you in business. I also know how much being shy, quiet, uncomfortable, or afraid to speak in groups can limit what you do and which opportunities you pursue.
My experience in Improv, business, personal development, and neuroscience has helped me create a workshop that is useful without feeling like school, challenging without being intimidating, and exceptionally fun without becoming pointless silliness.
You’re in good hands.
The Whens, Whys, and Wherefores…
Dates: Four Saturdays beginning September 12, 2026
Time: 10 a.m. until 1 p.m.
Location: West Tampa
Price: $347 for four weeks
Space is limited because the workshop works best when everyone has room to participate, connect, and receive individual attention.
Register now because this workshop will change your life!
Ready to Wing It & Win?
Four Saturdays. A small group.
A much more capable version of you.
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