I Can Fit That In

Confidence isn't something you're born with. It's built one conversation, one courageous ask, and one uncomfortable moment at a time.

In this episode of I Can Fit That In, Erin Coupe sits down with leadership sales trainer, speaker, and communication strategist Klyn Elsbury to explore how persuasion, self-advocacy, and authentic communication shape every area of our lives. Drawing from her experience living with cystic fibrosis and building a career around helping leaders communicate with confidence, Klyn shares why sales isn't about convincing people—it's about creating genuine connection and having the courage to ask for what matters.

What You'll Take Away

- Why confidence is built through action, not by waiting until you feel ready

- How "rejection therapy" can help you become more comfortable asking for what you want

- Why authentic conversations outperform traditional sales tactics every time

- How avoiding difficult conversations creates resentment and holds back personal and professional growth

- Practical ways to strengthen your communication, negotiation, and leadership skills every day

Guest Bio

Klyn Elsbury is a leadership sales trainer, speaker, and communication strategist who helps organizations build trust, strengthen influence, and communicate with confidence. Her work combines real-world sales experience with powerful lessons on courage, resilience, and authentic leadership.

Connect with Klyn:

https://www.linkedin.com/in/klynelsbury

www.leadershipsalestraining.com

Revenue Growth Roadmap  https://sales.leadershipsalestraining.com/sos-714503

https://www.youtube.com/@realklynelsbury

If this conversation inspired you to have the conversations you've been avoiding, subscribe to I Can Fit That In and leave a review to help more leaders discover the show.

Connect with Erin Coupe:

Instagram: @authenticallyec

LinkedIn: Erin Coupe

Chapters

00:43 Meet Klyn Elsbury

01:25 The Story That Shaped Her Life

03:22 From Corporate Sales to Fighting for Survival

05:23 Courage Starts With Asking

07:04 Why People Struggle to Ask for What They Want

11:30 Rejection Therapy and Building Confidence

13:29 Why Selling Feels So Uncomfortable

17:31 Difficult Conversations and Resentment

19:23 Building a Business Through Authenticity

21:14 Confidence Is Built by Winning

23:03 Rituals for Intentional Leadership

25:17 What to Do When You Feel Stuck

26:58 Narrate Your Life Like the Hero

27:56 Where to Connect with Kyln

29:13 Outro

Brad Hargreaves helped build two companies worth over half a billion dollars combined. His biggest regrets aren't the risks he took. They're the quarters he spent grinding on a path he already knew was wrong.

In this episode, Erin sits down with Brad Hargreaves, co-founder of General Assembly and Common and founder of Thesis Driven, a publication exploring innovation across the built world. Brad shares how a pandemic moment at home with his one-year-old changed his entire relationship with ambition, and why he built his current business around the life he wants instead of the other way around. It's a candid conversation about entrepreneurship, reinvention, and what real success looks like when you stop following someone else's playbook.

What You'll Take Away

- Why constraints fuel creativity, and how Brad used a single non-negotiable (being home to put his kids to bed) to shape his entire next business

- How General Assembly went from one New York classroom to training Fortune 500 companies in three years, and why timing mattered more than getting everything right

- Brad's honest answer to anyone who feels stuck on a fixed path, and the one question that tells you whether it's time to reinvent

- The real cost of staying the course when you know it's wrong, and the regret Brad still carries from his venture-backed years

- The mantra Brad has repeated to himself 200 times over 20 years of building companies

More About Brad

Brad Hargreaves is the founder and editor of Thesis Driven, a publication covering innovation in the built world. He previously co-founded General Assembly, a pioneer in skills-based education, and Common, a company reimagining urban housing.

Subscribe to I Can Fit That In so you never miss a conversation on building ambition and alignment into the same life.

Connect with Brad:

💼 LinkedIn: Brad Hargreaves

🌐 Website: thesisdriven.com

📧 Email: [email protected]

Connect with Erin Coupe:

💫 Instagram: @authenticallyec

💼 LinkedIn: Erin Coupe

🌐 Website: ErinCoupe.com

Your brain doesn't care whether it's incoming emails or incoming artillery fire. It's the same brain under pressure either way, and most of us were never taught how to fly it.

Sarah Furness spent 21 years in the military as a combat helicopter pilot before becoming an international keynote speaker and mindfulness coach. In this conversation with Erin, she shares how the tools that kept her steady in a war zone translate directly to boardrooms, inboxes, and everyday stress. From her Practice Scared philosophy to her HABITS method for focus, Sarah makes the case that courage isn't the absence of fear. It's what you build every time you act before you feel ready.

What You'll Take Away

- Why your brain responds to everyday stress the same way it responds to combat, and how to work with that instead of against it

- What Practice Scared means and how treating every day as a rehearsal builds real confidence without waiting to feel ready

- The "fly the aircraft" technique pilots use to pull their attention back to the one thing that matters when everything goes wrong

- Why multitasking is a myth, and how unitasking helps you do more by doing less

- The military debrief habit that turns every experience into self-trust, so your instincts get sharper with every rep

Chapters

0:00 Welcome and meet Sarah Furness

1:40 Incoming emails vs. incoming artillery fire: how the brain handles pressure

3:02 21 years in the military as a combat helicopter pilot

4:01 What deploying to a war zone is really like

6:18 The Practice Scared philosophy: train hard, fight easy

9:43 Distraction, mindfulness, and learning to "fly the aircraft"

12:07 Why we're addicted to busyness and what we're avoiding

14:57 Unitasking and the HABITS method

17:48 Control vs. composure: staying grounded when things go sideways

19:22 How courage and fear work together

22:03 Building self-trust through the debrief habit

24:23 Confidence is built, not born

27:02 Where to find Sarah

More About Sarah Furness

Sarah Furness is a former combat helicopter pilot turned international keynote speaker and mindfulness coach. She is the creator of the HABITS method and the Practice Scared philosophy, helping leaders perform with courage and composure in high-pressure environments.

If this conversation gave you a new way to think about pressure, subscribe to I Can Fit That In so you never miss an episode like this one.

Connect with Sarah:

 💫 Instagram: @wellbeitcoach

💼 LinkedIn: Sarah Furness

🌐 Website: SarahFurness.com

Connect with Erin Coupe:

💫 Instagram: @authenticallyec

💼 LinkedIn: Erin Coupe

🌐 Website: ErinCoupe.com

Andy Schoonover's daughter needed a simple ear procedure. He had insurance and did everything right. But the insurer called it "not medically necessary" and sent him a bill for $8,000 anyway. That was the last check he ever wrote them. So he built an alternative for 30,000 families instead.

Andy Schoonover is the founder and CEO of CrowdHealth, a community-based alternative to traditional health insurance that has helped over 30,000 families pay for healthcare directly, without deductibles, without networks, and without handing their money to a company with every incentive to deny their claims. Erin is a CrowdHealth member herself, and this conversation goes well beyond the pitch. She and Andy dig into why the traditional insurance model is broken beyond repair, what it actually takes to disrupt a $6 trillion industry, and why true agency over your health and your finances starts with being willing to do things differently than everyone around you.

What You'll Take Away

- How CrowdHealth works and why 30,000 families are paying a fraction of what traditional insurance costs them each month

- What actually happens if you go to the ER without traditional insurance, and why it's far less scary than you think

- Why the best doctors in the country are quietly moving to cash pay only, and what that means for how you access care

- How Andy navigated death threats, online attacks, and self-doubt while taking on one of the most entrenched industries in America

- Why Andy believes health insurance is in a death spiral, and what a post-insurance healthcare landscape could actually look like

More About Andy

Andy Schoonover is the founder and CEO of CrowdHealth, a community-funded alternative to traditional health insurance serving over 30,000 members across the country. He is a second-time healthcare entrepreneur whose mission is to give families the tools, the community, and the agency to take real ownership of their health.

Ready to Make the Switch?

Try CrowdHealth and stop outsourcing your healthcare decisions to a system that wasn't built for you. Subscribe to I Can Fit That In so you never miss a conversation like this one.

Listeners and viewers can try CrowdHealth for just $99 per member per month for their first three months. Use promo code COUPE at joincrowdhealth.com to get started.

Connect with Andy:

💼LinkedIn: Andy Schoonover

🌐Website: joincrowdhealth.com (Promo Code: COUPE)

Connect with Erin Coupe: 

💫 Instagram: @authenticallyec 

💼 LinkedIn: Erin Coupe 

🌐 Website: ErinCoupe.com

#healthinsurance #crowdhealth #healthcarereform #entrepreneurship #businesspodcast

Your intuition isn't something you have to find — it's something you learn to trust. In this episode, Erin Coupe sits down with transformational leader and New York Times bestselling author Christy Whitman to explore how energy, intuition, and intentional thinking shape the way we lead, live, and create meaningful results.

Christy shares her journey from feeling unfulfilled despite checking all the boxes of success to becoming a globally recognized teacher of energy mastery, manifestation, and personal transformation. Together, Erin and Christy unpack how leaders, entrepreneurs, and high achievers can identify limiting beliefs, protect their energy, and strengthen their connection to intuition to make better decisions in both business and life.

If you've ever questioned whether you're listening to fear or intuition, this conversation offers a practical framework for recognizing the difference and creating more alignment in your daily life.

What you'll take away:

- How to tell the difference between intuition and fear-based thinking

- Why your words directly influence your energy and decision-making

- A simple way to move from a scarcity mindset into a more abundant state

- How meditation creates space for clearer intuition and stronger self-leadershipWhy manifestation isn't wishful thinking, but intentional focus paired with action

About Christy Whitman:

Christy Whitman is a two-time New York Times bestselling author, transformational leader, energy healer, and channel for The Council. For more than 25 years, she's helped entrepreneurs, coaches, and leaders align their energy, release limiting beliefs, and create lives filled with abundance and purpose.

Subscribe to I Can Fit That In and leave a review if this episode resonated with you. Your support helps us bring more meaningful conversations about leadership, intentional living, and personal growth to a wider audience.

Connect with Host Erin Coupe

💫Instagram: @authenticallyec

💼 LinkedIn: Erin Coupe

🌐 Website: ErinCoupe.com

Kersten Weber Tatarelis has led billion-dollar healthcare transformations. She could not stop her mother's dementia. This episode is about what happens when the most capable person in the room can't fix what matters most.

Kersten Weber Tatarelis spent more than two decades leading billion-dollar clinical and operational transformations across the country's largest health systems. She knows how to solve complex problems at scale. What she couldn't solve was watching her mother disappear to dementia while raising four kids and running enterprise teams. In this episode of I Can Fit That In, Kersten and Erin get honest about the sandwich generation, the specific pressure women in leadership face when elder care collides with career, and what it actually takes to stop running on empty when the people you love need you most.

What You'll Take Away

- Why women disproportionately carry the weight of elder care and what that costs them professionally, emotionally, and physically

- The early conversations to have with aging parents while they can still tell you what they want, and why most people wait too long

- How Kersten learned to set boundaries around caregiving visits so she could show up present instead of resentful

- What most organizations are still missing when it comes to supporting employees through elder care demands

- Why owning your caregiving story, especially in a job search, is more powerful than hiding it behind words like "sabbatical"

More About Kersten

Kersten Weber Tatarelis is a nationally recognized healthcare executive with more than 20 years leading large-scale clinical and operational transformation across major health systems. She is also a mother of four and a primary caregiver for her mother, who is living with an atypical form of dementia.

This one is worth sharing. If someone in your life is holding everything together right now, send this episode their way. And if you haven't subscribed yet, now's a good time.

Connect with Kersten:

💼 LinkedIn: Kersten Weber Tatarelis

Connect with Erin Coupe: 

💫 Instagram: @authenticallyec 

💼 LinkedIn: Erin Coupe 

🌐 Website: ErinCoupe.com

#sandwichgeneration #leadershipcoaching #womeninbusiness #caregiving #businesspodcast

Everyone celebrates the exit. Nobody talks about what it costs you to get there. Riggs Kubiak built and sold a $50M construction tech company, and he's here to tell you what the highlight reel left out.

In this episode of I Can Fit That In, Erin sits down with Riggs Kubiak, entrepreneur, investor, and author of the new book Earned, a raw behind-the-scenes look at what it actually takes to build something meaningful. Riggs founded Honest Buildings, scaled it to 120 employees, raised over $50 million in venture capital, and sold it to Procore, which later went public on the New York Stock Exchange. This conversation isn't a success story in the traditional sense. Erin and Riggs dig into the emotional realities of entrepreneurship, the burnout, the self-doubt, the identity questions that most founders are too afraid to say out loud. If you're building something, leading a team, or standing at the edge of a big leap, this one is for you.

What You'll Take Away

Why you can't outwork your way through every stage of building a business, and what actually moves the needle when hard work alone isn't enough

How to recognize when your drive to perform is crossing into burnout territory, even when you think you're fine

Why the inner critic shows up loudest at the highest levels, and how naming it changes your relationship with it

What Riggs wishes he'd known about protecting his identity, relationships, and wellbeing while scaling a company

How vulnerability in leadership isn't weakness. It's the thing that gives other people permission to be honest too

More About Riggs

Riggs Kubiak is the founder of Honest Buildings, acquired by Procore Technologies, and the author of Earned, a founder's guide to the stages, mistakes, and real growth that entrepreneurship demands. He now invests in and advises early-stage founders.

If this episode resonated, subscribe so you never miss a conversation that goes beyond the surface. And if you know a founder, leader, or professional who needs to hear this, share it with them.

Connect with Riggs:

💼 Linkedin: RiggsKubiak

Twitter: riggskubiak

Connect with Erin Coupe:

💫 Instagram: @authenticallyec 

💼 LinkedIn: Erin Coupe 

🌐 Website: ErinCoupe.com

#entrepreneurship #leadershipcoaching #businesspodcast #founders #womeninbusiness

What if the life you're meant to live is already inside you, waiting to be uncovered?

In this inspiring conversation, Erin Coupe sits down with author, keynote speaker, and emotional intelligence practitioner Tara Renze to explore the message that transformed her life: "Be who you came to be." Sparked by a letter from her grandmother to her newborn son, Tara shares how that simple phrase became a lifelong mission of self-discovery, authenticity, and purpose.

Together, Erin and Tara discuss emotional intelligence, self-leadership, personal growth, workplace culture, and why fulfillment comes from becoming more of who you truly are, not achieving more. They also unpack Tara's powerful concept of Butterfly Goals and how taking one imperfect step can create extraordinary change.

Key Takeaways:

- Why self-leadership is the foundation of great leadership

- How Butterfly Goals help you reconnect with purpose and joy

- The role emotional intelligence plays in fulfillment and success

- Why perfectionism keeps people stuck How one imperfect step can change everything

If you've been feeling stuck, unfulfilled, or disconnected from your next chapter, this conversation is your reminder that becoming who you came to be is a lifelong journey worth taking.

Connect with Host Erin Coupe

💫Instagram: ⁠⁠@authenticallyec⁠⁠

💼 LinkedIn: ⁠⁠Erin Coupe⁠⁠

🌐 Website: ⁠⁠ErinCoupe.com

Connect with Tara:

https://www.tararenze.com

https://www.instagram.com/tararenze/?hl=en

When life feels uncertain, most people freeze. Meredith Elliott Powell learned how to move forward anyway.

In this episode of I Can Fit That In, Erin Coupe sits down with business growth strategist, keynote speaker, and bestselling author Meredith Elliott Powell to unpack what it really takes to navigate disruption, uncertainty, and change without losing momentum. From career pivots and economic instability to burnout, leadership pressure, and personal setbacks, Meredith shares how resilience is built in real time.

Together, Erin and Meredith explore why mindset alone is not enough, how rigid goals can actually hold people back, and why “moving the needle” matters more than chasing perfection in today’s unpredictable world.

Key takeaways from this episode:

- How to reframe disruption as opportunity

- Why resilience requires action, not just optimism

- The mindset shift that helps people keep going during uncertainty

- How leaders and entrepreneurs can avoid burnout while staying focused

If you’ve been feeling overwhelmed, stuck, or unsure of your next move, this conversation will help you reconnect with clarity, confidence, and possibility.

Tune in and discover how uncertainty might actually become your greatest advantage.

Connect with Host Erin Coupe

💫Instagram: ⁠@authenticallyec⁠

💼 LinkedIn: ⁠Erin Coupe⁠

🌐 Website: ⁠ErinCoupe.com

What if the future of work is not about doing more, but becoming more human?

In this episode of I Can Fit That In, Erin Coupe sits down with workplace expert, bestselling author, and Work Forward CEO Brian Elliott for a powerful conversation about leadership, burnout, AI, team dynamics, and what truly drives sustainable performance in today’s evolving workplace.

Drawing from decades of experience at companies like Google and Slack, Brian shares why curiosity is the leadership skill that matters most, how hustle culture continues to damage performance, and why the strongest teams are built on trust, clarity, and human connection.

Together, Erin and Brian unpack the tension between flexibility and accountability, the hidden cognitive cost of AI, and how leaders can create healthier, more sustainable ways of working without sacrificing results.

In this episode, you’ll learn:

- Why AI is increasing cognitive overload for many teams

- The leadership mindset that creates trust and engagement

- How sustainable performance actually improves business outcomes

- Why empathy and team connection matter more than ever

- The shift from productivity obsession to meaningful impact

If you’ve been questioning the way we work, lead, and define success, this conversation will leave you feeling both grounded and hopeful.

Connect with Brian Elliott on LinkedIn and through his work with Charter and Work Forward.

Connect with Host Erin Coupe

💫Instagram: ⁠@authenticallyec⁠

💼 LinkedIn: ⁠Erin Coupe⁠

🌐 Website: ⁠ErinCoupe.com

Connect with Brian

https://www.linkedin.com/in/belliott/