Who Made You the Boss?

In this deeply personal conversation with inspiring Jess Ekstrom, we delve into Jess's journey from relentless optimism to wrestling with imposter syndrome. Listeners will be invited to reflect on their own definitions of success and the balance between ambition and sanity. Jess shares candid stories of her entrepreneurial ventures and the 'false summits' she's encountered along the way, providing a relatable narrative for anyone striving for the next level in their career. Whether discussing devastating setbacks or the quieter moments of gratitude, Jess's experiences encapsulate the essence of redefining success on your own terms. Prepare for a transformative discussion that tackles monumental life changes, such as entering motherhood, battling postpartum challenges, and maintaining a sense of self amidst it all.

What You'll Learn in This Episode:

ABOUT JESS:

Jess Ekstrom is the founder of Headbands of Hope and Mic Drop Workshop, investor in women, 2x best selling author, Forbes Top Rated Speaker and new mom.  Her first brush with success was selling all of her toys on eBay when she was twelve. Since then, Jess and her companies have been featured on Today and Good Morning America and in Seventeen, Vanity Fair, Forbes, and People. More importantly, they've helped millions of women and girls around the world.  She’s the bestselling author of Chasing the Bright Side and Create Your Bright Ideas. Her hobbies include writing, hiking, board games with her husband, playing peekaboo with her baby, and searching for the best breakfast burrito in America.

Connect with Jess:

Website

Instagram

Twitter

Facebook

Resources from this episode:

For more information and to connect with our host, Lindsey Epperly, visit lindseyepperly.com 

Looking to turn your Imposter Syndrome into Inspiration? Grab the workbook here!

Host Lindsey Epperly delves into the origin story of her own imposter syndrome and how it has manifested throughout her career, starting with a personal experience of being made to feel lesser than in high school. Listeners can expect to hear the story of how she turned those insecurities into entrepreneurial strategies to find success.

This episode is for you if you’ve ever wondered:

ABOUT LINDSEY: 

Lindsey Epperly is the CEO of Jetset World Travel, which she has scaled from a one-person operation into a team of over 80 dedicated members, recently recognized on the Inc. 5000 List of fastest growing companies. She has been named to the Forbes Next 1000 List and was most inspired by navigating her industry’s greatest crisis while expecting her first child, a season she affectionately refers to as the “MBA I never wanted.” Lindsey is dedicated to fighting burnout and imposter syndrome while teaching others how to turn obstacles into opportunities on her podcast, Who Made You The Boss? 

Connect with Lindsey:

Instagram

LinkedIn

Resources from this episode:

The workbook that teaches you to turn Imposter Syndrome into Inspiration is available here!

This show delivers entrepreneurship strategies around imposter syndrome, burnout, and mental health. If you’re looking for tips on overcoming obstacles in business from an award-winning female founder who’s passionate about pursuing ambition without sacrificing your self worth, you’re in the right place. 

This podcast provides leaders, creatives and entrepreneurs valuable insights on why mindset matters in business, why failure is important to our self-confidence, and how to redefine our success factors to live a more meaningful life. 

This show is for you if you’ve ever wondered:

For a free resource to help you turn your imposter syndrome into inspiration, visit lindseyepperly.com/resources. 

Season 2 of Who Made You The Boss? launches May 1 and features Kara Goldin, Jess Ekstrom, Margot Bingham, and more. 

Even though we're in between seasons, we're excited to bring you this bonus episode from Lindsey's interview on Teri Holland's Success in Mind podcast. You'll hear how Lindsey has built her business from a single-member team into a thriving empire of over 70 professionals, overcoming tremendous personal and professional struggles along the way. From having her first child while navigating her industry's greatest crisis, to saving her business from the brink of closure and being listed on the Inc. 5000 list, Lindsey Epperly shares her awe-inspiring journey, offering valuable insights and practical tips on how to handle business growth and avoid burnout.

Follow Lindsey: 
Instagram

LinkedIn

Key Takeaways:
- Prioritize your business and make tough decisions during challenging times.
- Recognize the illusion of control and learn to delegate and trust your team.
- Focus on your unique strengths and delegate tasks that others can do.

Make sure to give the Success in Mind podcast some love for allowing us to run this interview by leaving the show a rating and review here!

If you haven't already, click that Follow button for Who Made You The Boss? to make sure you don't miss our Season 2 premiere! 

Lindsey takes us on a genuine - and unbelievable - journey as she navigates an island in lockdown, all during an insurmountable season of imposter syndrome. She candidly shares the impact of both personal and professional hurdles on her mental health and offers her own perspectives on resilience and vulnerability.

What you'll learn from this episode:

- Embrace the Full Story: Lindsey's experience shows the importance of owning our entire narrative – the successes and the struggles. By embracing our whole story, we can free ourselves from imposter syndrome and redefine what it means to be the boss of our own lives.

- Letting Go of Control: The episode highlights the difficulty in relinquishing control and embracing the cracks in our lives. It's a reminder that sometimes the breaking and reconstructing are where we find our strength and resilience.

- Hope and Redemption: Even in the midst of uncertainty and hardship, holding onto hope and choosing to rise is a powerful act of resilience. Lindsey's journey exemplifies how the worst experiences can lead to growth, redemption, and the beauty of putting the pieces back together.

ABOUT LINDSEY: 

Lindsey Epperly is the founder and CEO of Jetset World Travel, a modern travel agency dedicated to service, innovation and gratitude. Lindsey’s decade-long journey in the world of business started as a one-person operation built by attending bridal shows alongside her college courses that she and her business partner have transformed into a company of 70 mission-driven team members. Lindsey’s passion for entrepreneurship, as well as her outspokenness on battling burnout and imposter syndrome, have led her to earning a spot on the 2021 Forbes Next 1000, along with speaking and writing opportunities about turning obstacles into opportunities. She is currently studying under New York Times bestselling author Bob Goff to produce a book about the illusion of control.

Connect With Lindsey:

Website

Instagram

LinkedIn

Visit lindseyepperly.com for more about Who Made You the Boss?

Demir and Carey Bentley, the power couple behind Lifehack Method and authors of "Winning the Week: How to Plan a Successful Week Every Week,” dive into their strategies to gain radical clarity in your life and business. From the moment they first faced the opportunity to redefine their lifestyle in light of Demir's health crisis to their rise as productivity gurus advocating for work-life harmony, the Bentleys share candidly about their transition from traditional corporate America to a life of intentional design and freedom. Listen in as they discuss their unique approach to productivity, blending lifestyle design with actionable strategies for optimizing time.

What You'll Learn in This Episode

- How to take the emotion out of your priorities for a more effective system on balancing time and joy

- What it means to monitor the supply and demand of time management

- The test you can give yourself to determine if you’ve won the week

- Techniques to mitigate risks in entrepreneurship and the value of resilience in a volatile business environment

- How to determine what success looks like in your life and business

ABOUT DEMIR & CAREY:

Demir and Carey Bentley are the husband and wife team behind Lifehack Method, the productivity and lifestyle design company for high performing individuals who want to bring sanity back in their lives.

They’re WSJ Bestselling authors of Winning The Week: How To Plan A Successful Week, Every Week. Their work has been featured in ABC News, Forbes, Inc, Entrepreneur, Bloomberg, WSJ, HuffPo, and on podcasts like Entrepreneurs on Fire, Forbes 30 Under 30, Amy Porterfield's Online Marketing Made Easy, and The ONE Thing.

Carey and Demir live internationally with their two daughters. Their primary home base is Medellin, Colombia.

Follow Demir and Carey:

- Website

- Instagram

- Facebook

- YouTube

- Winning The Week: How to Plan a Successful Week Every Week, by Demir & Carey Bentley

Explore the intricate dance of identity, control, and personal evolution in this conversation with Darrah Brustein. As a lifestyle business expert, Darrah’s focused efforts have led her to found 5 businesses and collaborate with visionaries like Deepak Chopra. Today’s conversation uncovers the challenges of knowing when to walk away and the triumphs of building a life that genuinely aligns with one’s values. Darrah also shares her unique insights into borrowed confidence and the invaluable role of feedback in personal growth. This episode promises a candid look at striking a balance between pleasing others and preserving self—all through the lens of becoming the boss of one's own life.

What you'll learn in this episode:

- How your intuition influences when to quit and when to continue

- Why borrowed confidence can immediately uplevel the way you show up in life

- How to build a lifestyle business by aligning your values to your work

- How to recognize and move past the nature of people pleasing

- How to embrace the dual nature of feedback and integrate it for growth 

ABOUT DARRAH:

Darrah Brustein is a 5x founder, author, and coach. She helps overwhelmed business owners and entrepreneurial-minded executives access the freedom, flexibility, and impact they desire. 

After spending 10 years over-working and burning out while building a credit card processing company into 38 states and a networking events company for over 30,000 people (which she later sold), she learned the wrong way to do it, and then discovered that there was a better way.

A prolific writer and interviewer, she's worked with Shaq, Deepak Chopra, Seth Godin, Bobbi Brown, Jillian Michaels, Adam Grant, Robert Herjavec, Nastia Liukin, Cam Newton, and the list goes on as well as brands like Chase, Visa, Toyota and FedEx.

Her motto: “Design your life, build a career to fund it, and a network to support it" has inspired millions to reach higher and dream bigger. 

Follow Darrah:

- Website

- Instagram

- Linkedin

Mentioned in this episode:

- "The Dip" by Seth Godin

- Diving Deep with Deepak and Darrah video series

- Life Design and Discovery Lab: Darrah’s coaching program that guides clients in aligning their lives with their core values

- Darrah’s 9 Questions to Ask Your Network to Find Your Path

The multi-talented Allisyn Snyder tackles personal and professional growth, creative collaborations, and maintaining balance in life and relationships in this week’s episode of Who Made You The Boss? With Lindsey Epperly. Throughout the discussion, Allisyn shares her journey from an actor known for her YouTube persona Astrid Clover to a writer and director, co-founding Watch the Footage (WTF) Productions with her husband, Dylan Snyder. Lindsey and Allisyn dive into setting boundaries, the impact of morning routines, and filtering the noise of social media, all wrapped in an exchange filled with humor, vulnerability, and wisdom. 

What You'll Learn in This Episode:

- The importance of supportive partnerships

- How to foster curiosity and authenticity in your journey

- Why a daily routine grounded in writing and meditation is pivotal to your mental wellbeing

- The fun new trick of birdwatching meditation - who knew?!

- How to navigate industry changes within creative fields, especially during unforeseen circumstances and world upheavals

ABOUT ALLISYN:

Allisyn Snyder, a native of Los Angeles, embarked on her entertainment career at the age of 4 as Allisyn Arm. Notable TV appearances in shows like Friends, Strong Medicine, Judging Amy, and Still Standing marked her early success. Landing a series regular role in Disney Channel's Sonny With A Chance at 11, she later starred in its spin-off, So Random!, showcasing her diverse talents. Iconic for her role as Heather Wilmore in NBC's A.P. Bio, Allisyn transitioned to cinematography studies at Glendale CC at 15. Writing sketches for AwesomenessTV at 17, she co-created the YouTube personality Astrid Clover, releasing over 350 episodes. In 2016, she ventured into film production with Watch The Footage Productions. Beyond her creative pursuits, Allisyn is a skilled trapeze artist, aerial silks performer, kickboxer, and certified scuba diver, with a lifelong passion for art.

Follow Allisyn:

- Website

- Instagram

- Twitter

- Facebook

- Tik Tok 

Mentioned in This Episode:

- "The Artist's Way" by Julia Cameron

- Consider This by Chuck Palahniuk's Books

- Watch the Footage (WTF) Productions

Voice coach and author Samara Bay unpacks the nuances of voice bias and its effects on personal and professional leadership. Delving into Samara's unique experiences, both in Hollywood as a distinguished dialect coach and as an individual who has grappled with her own voice challenges, this conversation is a journey through the insecurities that come with public speaking, the social constructs around power and voice, and the importance of embracing diversity in communication. 

What you'll learn in this episode:

- What voice bias is and how we overcome stigmas

- Why we need a new sound of power - and how your voice can contribute

- How we can raise the next generation to accept and embraced varied communication styles

- What’s at stake when we don’t understand society’s standards around voice and leadership

- How to gain confidence in your business and yourself by embracing your voice’s thumbprint: your idiolect 

ABOUT SAMARA:

Samara Bay is the author of the 2023 Penguin Random House bestseller PERMISSION TO SPEAK: How to Change What Power Sounds Like, Starting with You. Behind the scenes, she coaches everyone from Hollywood celebrities to rising leaders in business & politics and high school girls ready for a new kind of leadership. She speaks and runs trainings around the world on the new sound of power—a question-everything unlearning about what speaking in public is all about. 

Follow Samara:

Website

Instagram

LinkedIn

YouTube

Twitter

Jacqui Gifford, Travel and Leisure's Editor in Chief, reveals her approach to effective leadership, the evolving trends in travel, and the broader implications of sustainability on the world at large. From insights into maintaining a harmonious work-life balance to tackling the pervasive challenges that women often encounter in modern workplaces, this discussion delves into themes that resonate with many professionals today. Learn more about Jacqui’s journey of balancing motherhood in the ever on-the-go travel industry, and the underlying thread of optimism and resilience that has defined her career journey, especially during the travel industry's most trying times.

What You'll Learn in this Episode:

- Jacqui’s no-nonsense leadership philosophy that led Travel+Leisure through a global pandemic

- How the travel industry’s focus on sustainability can impact future generations

- Why mothering in fast-paced careers like travel and media is so darn hard 

- Techniques to master communication in an era of overwhelming digital correspondence

- That wellness travel is here to stay – and so is recognizing the limits of your life

ABOUT JACQUI:

As the editor-in-chief of Travel + Leisure, Jacqui Gifford is always on the next plane. She constantly scouts for new hotels, shops, and restaurants to give readers the latest news and trends, and frequently appears as an expert guest on television networks, including NBC, CBS, ABC, CNBC, and MSNBC. A graduate of Princeton University with a bachelor's degree in English, Jacqui was born in Japan and raised in Saudi Arabia, Qatar, and Philadelphia, Pennsylvania. She has traveled the world extensively and lives in New York City with her husband and son. Her passions include sustainability, luxury, wellness, multigenerational travel, and more.

Follow Jacqui & Travel + Leisure: 

- Website

- Instagram

- Twitter

- Tik Tok

Additional References and Links:

World Economic Forum Article