Words may inspire, but only action creates change.
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Connect with us and others on their journeys.
Who we are.
Simon Optimism Press

Your People

These are challenging times, so taking care of each other really matters.

We’ve put together a selection of dynamic live online classes, virtual workshops and keynotes to help you help your people feel more inspired, safe and fulfilled.

You can create your own experience with our amazing team of master trainers and speakers.

Let's start something!

Design Your Experience

Choose one or mix and match

Keynotes & Workshops

Inspire your people with Simon’s message. One of Simon’s master trainers will deliver an inspiring talk or an interactive workshop.

Find Your

Interactive workshops to help your organization, team, founder or executive find their WHY led by one of Simon's master trainers.

Live Online

Learn leadership and life skills in our virtual classroom. Host a private class or let your people choose what they want to learn.

Keynotes & Workshops

Start at $15,000 each

  • 30-90 min talk with optional Q&A
  • Includes a pre-engagement call with your master trainer to better understand your needs
  • Unlimited participants
  • 90-120 min interactive session with break out rooms
  • Includes a pre-engagement call with your master trainer to better understand your needs
  • Max 300 participants

Find WHY

Any person or organization can explain WHAT they do, some can explain HOW they are different or better than their peers, but very few can clearly articulate WHY. The WHY is not about money or profit — those are results. The WHY is the thing that inspires us and inspires those around us. Learn how the WHY can act as a filter for our every thought, action and behavior, giving us an alternative perspective on our organizations, careers and lives.

Founder's WHY

one-on-one session

  • For a company founder or executive to find their personal WHY
  • 120 min

Start with WHY


  • For individuals on a team or an organization to find their WHY
  • Max 100 people
  • 120 min - 180 min

Organization & Team WHY


  • For organizations or teams to find their collective WHY
  • Max 25 people
  • 2 x 180 min sessions

Online Classes

Choose from a variety of live online classes to help with team building and personal and professional growth. Topics include everything from storytelling and improv to culture building and inclusive leadership.

Host a Private Class

Just like renting out a private dining room at your favorite restaurant, you can host a private live online class for your team. Choose the class, date and time and we’ll make it happen.

Take a Class

Want to join one of our live online classes with your team? Enroll 10-30 people and get inspired, together.

Virtual Gift Bags

Looking for a way to say thank you to your team? Give your team members the freedom to choose the classes they want to take by purchasing a ticket pack.

(or as many as you need)

Take care of yourself.
Take care of each other.



    Leaders Eat Last

    with one of Simon's master trainers

    Imagine a world where everyone wakes up inspired, feels trusted and valued during the day, and ends the day fulfilled by the work that they do. This is not a crazy, idealized notion. We will talk about how trusting relationships are built—the kind of relationships that can withstand the inevitable pressures and dangers all organizations face and how choosing to protect our people before our numbers can actually inspire them to take care of the numbers in the long term.


    The Infinite Game

    with one of Simon's master trainers

    We are all players in finite and infinite games, in our work and in our lives. We will distinguish the difference between the two and focus on the five essential practices that are required to lead in an infinite game: Just Cause, Trusting Teams, Worthy Rivals, Existential Flexibility and the Courage to Lead. Explore the power of how embracing an infinite mindset can help you, your team and organization thrive in an ever changing world.


    Build Trusting Teams

    with former Navy SEAL and author, Rich Diviney

    Teams are in all facets of organizations, business and life. Trust is vital to a team’s success, but how do we actually put it into practice? Building on Simon’s books, The Infinite Game and Leaders Eat Last, and of former Navy SEAL Commander and author, Rich Diviney’s work on optimal performance, we explore the necessary components to build trust. You’ll leave with practical and actionable steps that will yield sustainable long term results for your leadership and with your team.


    Build Relationships

    with entrepreneur and author, Kristen Hadeed

    We often hear that we have to leave our “personal stuff” at the door when we come to work. While there must be boundaries, why do we make people feel as if they have to be someone else at work instead of who they really are? Authenticity and vulnerability in our working relationships produce loyal, committed and more engaged people. Led by entrepreneur and author, Kristen Hadeed, your team will learn how better communication helps build genuine relationships so that you can accomplish more together.


    Deliver & Accept
    Feedback Effectively

    with entrepreneur and author, Kristen Hadeed

    We’ve all had situations where we want to give a colleague feedback about their performance or behavior and we do everything in our power to avoid it. Giving and receiving feedback is like a muscle we need to train. While feedback conversations can be hard, they’re often the most rewarding and important conversations we can have to help each other and our performance grow. Learn how to provide feedback in a way that inspires positive change with Kristen Hadeed, author of Permission to Screw Up.