Free Business Topics in Chicago

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Now the speaker will contact you in the next few days to coordinate details.

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  How to Have Effective Hard Conversations

  Tim Reynolds, Co-Founder, Clover Lane Partners, LLC

  Most of us dislike confrontation. As a result, we often feel a primal urge to avoid it at almost any cost. But there are real costs to be paid. Avoidance damages relationships, hurts productivity, and undermines leadership authority and the ability to develop and mentor others. And avoidance is all too common and often ends up in terminations that go horribly wrong or broken relationships leaving all involved dispirited. MORE >

  This practical, hands on workshop will provide both the training on how to overcome avoidance and the how to have an effective difficult conversation that will benefit everyone involved.

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  5 Secrets of Businesses That Actually Thrive (Not Just Survive)

  Amanda Wittenborn, Owner, Amanda Creation Inc.

  Why do some businesses seem to grow with ease while others constantly struggle to stay afloat?
  In this uplifting and practical keynote, Amanda Wittenborn, founder of a multi-million-dollar creative brand, reveals the five hidden factors that separate thriving entrepreneurs from the ones just trying to get by. MORE >

  After losing her business twice—and rebuilding stronger each time—Amanda discovered that lasting success isn’t about luck, trends, or working harder. It’s about mastering five timeless principles that every thriving business has in common.

  With her signature blend of real-world honesty and contagious optimism, Amanda helps audiences uncover what’s really holding them back and shows them how to create momentum, confidence, and clarity in their business again.

  Attendees will learn how to:
  ✅ Identify and focus on the work that actually drives growth
  ✅ Harness mindset and energy as tools for strategic success
  ✅ Build simple systems that support (not suffocate) creativity
  ✅ Stay grounded and resilient when plans fall apart
  ✅ Lead with purpose, authenticity, and joy

  Whether you’re an entrepreneur, creative, or leader in transition, this talk will inspire you to stop surviving—and start truly thriving.

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  Fail, Pivot, Rise: The Real Story Behind a 7-Figure Comeback

  Amanda Wittenborn, Owner, Amanda Creation Inc.

  What if losing everything was the best thing that ever happened to you?
  After being banned from Etsy and watching her thriving business collapse during COVID, Amanda Wittenborn could’ve quit. Instead, she rebuilt—twice—each time stronger and more aligned than before. MORE >

  In this raw, inspiring keynote, Amanda shares the real behind-the-scenes of losing, pivoting, and rising again to build a multi-million-dollar brand.
  You’ll learn how to:

  Turn failure into fuel for growth

  Recognize the signs it’s time to pivot

  Rebuild your confidence (and your business) when everything crumbles

  Audiences leave fired up, hopeful, and ready to turn any challenge into a comeback story of their own.

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  Your Superpower Advantage: The Mindset Shift That Built a 7-Figure Business

  Amanda Wittenborn, Owner, Amanda Creation Inc.

  What if the key to your next level of success isn’t outside of you—but already inside?
  In this energetic, interactive talk, 7-figure entrepreneur Amanda Wittenborn helps audiences uncover the hidden strengths that make them magnetic to success. She reveals how she built her multi-million-dollar brand not by following trends or strategies—but by amplifying her natural gifts and trusting her own creative power. MORE >

  Attendees will walk away knowing how to:

  Identify their unique “superpower” that no competitor can replicate

  Reframe self-doubt into confidence and clarity

  Use authenticity as a growth strategy in business and life

  Perfect for entrepreneurs, women in business, or creative professionals ready to stop blending in and start standing out.

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  Cash Flow is King: Why Profit Doesn’t Always Mean You’re in Control

  Mark Knaack, Business Development Director, Guardian Chamber

  Every business owner has heard the phrase “cash is king,” but too many discover the truth the hard way — when they run out of cash even though their business looks profitable on paper. Profit is an accounting result, but cash flow is what keeps the doors open, employees paid, and opportunities funded. MORE >

  At Guardian Chamber, we teach owners how to take control of their financial story by understanding where their money really goes, building systems to smooth out cash flow, and using credit as a safety net—not a crutch. Because when you have clarity on your cash, you gain both control and the confidence to scale.

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  The Hidden Value Driver: How Business Credit Builds Company Worth

  Mark Knaack, Business Development Director, Guardian Chamber

  Most business owners think of credit only as a way to borrow money, but the truth is, strong business credit is a hidden driver of company value. When banks, investors, and even potential buyers look at your business, they’re not just reviewing your financial statements — they’re evaluating your ability to access and manage capital without leaning on personal guarantees. MORE >

  A business with established credit is seen as more fundable, less risky, and ultimately more valuable. At Guardian Chamber, we show owners how building credit isn’t just about getting loans — it’s about creating leverage, increasing valuation, and giving you more control over your company’s growth and future.

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  Stories that Connect: Building Empathy Through Personal Narrative

  Leilani Garrett, Principal Storyteller / Founder, Be More Human

  In this 90-minute interactive experience, Leilani guides participants through the process of writing and sharing their personal stories. The result? Deeper trust, increased empathy, and real connection between colleagues who usually only talk in metrics. Ideal for leadership retreats, ERG activations, or culture-building experiences, this workshop makes space for brave reflection and meaningful dialogue—and leaves teams more human than they were before. MORE >

  This is more than a workshop—it’s a reset.

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  Building Collective Success: Empathy. Storytelling. & Change.

  Leilani Garrett, Principal Storyteller / Founder, Be More Human

  In a time when workplace connection is at an all-time low and culture-building feels more buzzword than blueprint, Leilani offers something different: a keynote that makes people feel—and think. Her signature talk, Building Collective Success: Empathy. Storytelling. & Change, challenges audiences to rethink the way we define leadership, performance, and culture. MORE >

  Through personal narrative, pop culture references, humor, and hard data, Leilani shows how story-driven empathy isn't just a “nice-to-have”—it’s a business imperative. Expect aha moments, audience participation, and a masterclass in communication that sticks long after the standing ovation.

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  Connecting People and Purpose: Rethinking Employee Engagement

  Anthony Bolden and Charles Cammack, Co-founders, BridgeWork LLC

  What if employee engagement isn’t about perks or productivity but about authentic investment? In this interactive session, we walk through the BridgeWork Framework to explore how people-centered workplaces are built when employees feel seen, supported, and connected to purpose. Participants will reflect on what they carry into the workplace, both personally and professionally, and how that shapes their contributions. Together, we’ll examine what it means to invest in work at a shallow or deep level and offer practical tools for building cultures where people thrive. Whether you’re leading a team or just finding your footing, this talk offers a fresh path forward that connects who we are with how we work. MORE >

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  Generation Z (Zoomers) in the Workplace

  Mary Erlain, President, Peak Development Strategies

  The workplace has undergone a profound transformation in recent years, driven by two seismic shifts: the pandemic and the generational turnover in the workforce. MORE >

  Time has seemed to fly by, bringing with it a wave of change that many of us barely registered. A new generation has quietly entered the workplace, but have we truly acknowledged their arrival?

  For many, the answer is no—and for a good reason. Gen Z stepped into their professional roles during a time of unprecedented disruption. Remote work and virtual meetings on platforms like Zoom replaced traditional onboarding experiences, making their entry less noticeable but no less impactful.

  Their influence on organizations has been significant, though often misunderstood. This book, The Zoomers: Our Next Generational Wave in the Workplace, aims to change that. It offers an insightful and constructive perspective on Gen Z, challenging stereotypes and providing a deeper understanding of their values, behaviors, and expectations.

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