Power of Why with Naomi Haile

Lianne Hannaway is a CPA, financial educator, and wealth coach helping first-generation professional women build wealth without sacrificing values. Creator of the Bridge System™, she has guided over 500 first-gen professionals through her workshops and programs. In this conversation, she explains why standard money advice often leaves out the people you support, and how to plan generosity, protect your freedom, and price your expertise for the life you want.

Connect with Lianne Hannaway

Website → https://www.liannehannaway.com/ 

LinkedIn → https://www.linkedin.com/in/liannehannaway/ 

YouTube → youtube.com/@emotionsplusmath

Connect with Naomi Haile:

Website →⁠ https://www.naomihaile.com/⁠

Sign up to my Newsletter →⁠ https://powerofwhy.kit.com/57ca5180df⁠

Purchase the Purpose Canvas to ensure your dreams have an action plan →⁠ https://naomiahaile.gumroad.com/l/purposecanvas⁠

LOOKING FOR A SPECIFIC GEM?

• 00:00 Welcome and introduction to Lianne Hannaway
• 04:15 Growing up as the daughter of Caribbean immigrants
• 05:44 Working at 11 and learning financial responsibility early
• 10:04 Entering Big Four accounting without knowing the doors existed
• 13:02 Making partner, playing the part, questioning the next ladder
• 16:15 Earning for yourself while carrying family responsibilities
• 17:49 Finding people willing to talk openly about money
• 24:16 Why “pay yourself first” doesn't work for every family
• 25:50 Building the four bridges: security, growth, legacy, freedom
• 28:43 Bringing culture and lived reality into financial planning
• 30:14 Discovering that money is math plus emotions
• 34:49 Why financial stress can persist at a high income
• 37:30 Reframing what it means to be “the first”
• 41:03 Adjusting family support before leaving full-time employment
• 43:28 Expanding the definition of an emergency fund 47:17 Why entrepreneurs need to understand pricing and worth
• 50:54 Building wealth when some of your wealth lives in the business
• 54:04 Demystifying investing through the Tax-Free Savings Account (TFSA)

Ariana Lavelli is a Solutions Engineer at Slack (Salesforce), where she helps small businesses spot the gaps in how they work and match them to the right tech. She holds a bachelor's and master's degree in Accounting (with a minor in Spanish) from Binghamton University, and got her start at KPMG before making the jump to tech. 

The real turning point came in 2023, when Ariana became her mother's primary caregiver after a terminal diagnosis. After her mom passed, Ariana became the family's default executor, which meant she was the one untangling probate, estate admin, and all the family dynamics that grief blows wide open. Unexpectedly, she lost several more people close to her in quick succession, and learned some uncomfortable lessons firsthand and more than once. 

So on the two-year anniversary of her mom's death, Ariana started Light & Ari, a grief and end-of-life support company built to fill that experience gap for others. It's meant to be practical, unglamorous help for grievers and executors, delivered with the same whimsy and warmth her mom always brought to everything.

Right now, Light & Ari is launching an Etsy shop of curated goods for the grief-stricken and the people who love them, with plans to grow into full-service support: legacy planning, document organization, probate guidance, trust funding, estate and home sales, memorial planning, the whole thing. Ariana is building it out of Brooklyn alongside her corporate career, with an eye toward going full-time early next year.

Connect with Ariana Lavelli

Website → ⁠https://thelightandari.com/⁠ 

Etsy Shop → https://www.etsy.com/shop/LightandAriShop

LinkedIn → https://www.linkedin.com/in/arianalavelli/

Email → [email protected]

The Light and Ari Instagram → https://www.instagram.com/thelightandari/ 

Connect with Naomi Haile:

Website → https://www.naomihaile.com/

Sign up to my Newsletter → https://powerofwhy.kit.com/57ca5180df

Purchase the Purpose Canvas to ensure your dreams have an action plan → https://naomiahaile.gumroad.com/l/purposecanvas

LOOKING FOR A SPECIFIC GEM?

• 00:00 Welcome and Ariana's story
• 06:00 Growing up in Yonkers and how travel shaped her view of community
• 09:25 Why third places matter, and why they're disappearing
• 10:20 How Ariana turned her own rooftop into a community space
• 13:01 AI, isolation, and the human need for connection
• 16:32 The "reverse centaur": what happens when AI takes the helm
• 20:05 Helping businesses separate AI FOMO from actual need
• 24:36 When grief breaks the optimization mindset
• 27:03 "There's no scorecard to life"
• 32:14 Why "How can I help?" may be the wrong question
• 38:31 The two deaths of a person: physical death and the death of memory
• 42:57 How losing her mother changed Ariana's relationship with work and money
• 46:12 Wills, trusts, healthcare preferences, and legacy conversations
• 55:45 From professional organizing to Light and Ari
• 59:12 Building a concierge for the logistical side of loss
• 1:01:59 The vision: from Etsy shop to a physical third place for grievers

Cali Williams Yost is the Founder and CEO of Flex+Strategy Group (FSG), a futurist, and was called "one of the most sophisticated thinkers" on the transformation of work by The New York Times. In the 90s, Cali graduated from Columbia Business School and began working in banking, at a think tank, and after seeing a large gap in the market, she launched her own consulting practice in 1998.

For nearly three decades, FSG has helped organizations define the optimal operating architecture that drives high performance across places, technology, and time. Cali and her team engage all levels, from the C-Suite to the frontline, to build on what's working, reimagine what's possible, and then make that vision a reality guided by a proven, evidence-based framework.

She has worked with and is trusted by organizations like BDO USA, The Gates Foundation, Columbia University, Stanford University, ConEdison, Memorial Sloan Kettering, and the Singapore Government.

At a moment when many organizations feel they must make consequential decisions about AI and talent reactively, Cali is truly that leader that is looking at the data and helping leaders transform work deliberately. You can find her commentary regularly in the Wall Street Journal, Harvard Business Review, CNBC, NPR, and NBC Nightly News.

Cali is the author of two books on work transformation, “Work+Life; Finding the Fit That’s Right For You” and “Tweak It; Make What Matters to You Happen Every Day”, and is a sought-after keynote speaker for audiences worldwide.

Connect with Cali Williams Yost

LinkedIn → https://www.linkedin.com/in/caliwilliamsyost 

Website → https://flexstrategygroup.com/ 

Instagram → https://www.instagram.com/caliwilliamsyost/ 

FSG Instagram → https://www.instagram.com/flexstrategygroup/

Connect with Naomi Haile:

Website → https://www.naomihaile.com/

Sign up to my Newsletter → https://powerofwhy.kit.com/57ca5180df

Purchase the Purpose Canvas to ensure your dreams have an action plan → https://naomiahaile.gumroad.com/l/purposecanvas

LOOKING FOR A SPECIFIC GEM?

• 00:00 Welcome and introduce Cali Williams Yost and Flex Strategy Group
• 04:39 Growing up with a single mom whose work model didn't fit her life
• 07:31 The bank CEO's "stone cold businessman" line, the moment Cali decided to quit
• 15:03 Starting with the work, not the tool
• 18:04 The return-to-office mistake companies are now repeating with AI
• 21:37 The foundational conditions an organization needs before change will stick
• 24:02 Nobody trains managers — and why that's become unsustainable
• 25:22 The labor demographic shortage nobody's talking about
• 27:37 Reactive layoffs today, a talent cliff in three to four years
• 27:55 Why letting older workers retire wastes irreplaceable domain expertise
• 30:59 Why global companies aren't worried about the labor shortage
• 32:55 The "light bulb" moment that became the concept of work-life fit
• 32:35 Why "balance" puts unfair pressure on young people
• 37:22 The Oprah and Emma Grede moment that proves the point
• 39:13 Resetting the business when her daughter got sick
• 42:44 Redefining success instead of chasing an all-or-nothing standard
• 44:59 Her advice to young people: there's no fixed 50-50 split
• 46:33 Where to start with AI if you don't have a massive budget
• 49:26 Her book got scraped by AI
• 51:32 Making space for fun in the middle of all this change

Bea Arthur built two startups, landed on Shark Tank, and became the first Black female founder accepted into Y Combinator. Then she hit a wall and decided to finally choose herself. So she traded the hustle for a slower life in Mexico City, where she's writing her forthcoming book, “The White Man Within” that reframes every setback along the way as data, not damage.

⁠Bea Arthur, LMHC⁠ is a Columbia University-trained psychotherapist, award-winning entrepreneur, TEDx speaker, and true pioneer in the field of mental health. Bea has been named an Entrepreneur to Bet On by Newsweek Magazine and one of the 100 Most Inspirational New Yorkers by Bumble.

Bea shared her career as a social worker, where she served addicts in recovery, survivors of domestic violence, and students in the New York City public school system. 

She’s always been passionate about lifting people up and decided to scale this gift in the tech world. In 2011, her career took off at the intersection of psychology and technology, when her first startup Pretty Padded Room competed on ABC’s Shark Tank, which put “online therapy” on the map! In 2014, she became the first African-American female founder accepted by Y Combinator accelerator program.

8 years ago, she launched her second startup called The Difference, which was the very first Alexa Skill for easy access therapy.

Now, she’s a first-time author. Her book “The White Man Within”, where she tells her story,  how she created her own path to success, and how you can too! Bea, welcome to the show.

Connect with Bea Arthur

LinkedIn → ⁠http://www.beaarthurtherapy.com⁠ 

Instagram → ⁠https://www.instagram.com/bbarthur/⁠ 

Book Instagram → ⁠https://www.instagram.com/thewhitemanwithin/⁠ 

Book Website → ⁠https://www.thewhitemanwithin.com/⁠ 

Connect with Naomi Haile:

Website → https://www.naomihaile.com/

Newsletter → https://powerofwhy.kit.com/57ca5180df 

Purchase the Purpose Canvas to bring alive your dreams tomorrow: ⁠https://naomiahaile.gumroad.com/l/purposecanvas⁠ 

LOOKING FOR A SPECIFIC GEM?

00:00 Welcome and introduction to Bea Arthur

06:52 Origin story: Ghanaian immigrant family raised in Houston

07:19 Kicked out of school for "talking back"

09:15 How Bea went from real estate to becoming a therapist

14:48 What made her write the book “The White Man Within” now

14:56 Conforming inside the tech world's unequal rules

18:30 Founder vs. CEO?

21:10 Analyze vs. act

23:18 Bea investing online therapy with Pretty Padded Room

33:09 "Strong Seed, Wrong Soil" and the cost of the wrong environment

35:30 Her actual morning practice

37:36 Why Mexico City lowered her stress and sped up the her book writing process

42:33 "Data, not damage" and her father's story about racism in 1980s Texas

44:39 "This is a station, not the destination"

47:09 Performing less and allowing the messy middle

51:17 Reframing "everything happens for a reason"

53:53 The matriarchy reframe (love instead of suffering)

55:59 Doing more of what makes you happy

55:38 Where to find Bea and her book online

Bea Arthur built two startups, landed on Shark Tank, and became the first Black female founder accepted into Y Combinator. Then she hit a wall and decided to finally choose herself. So she traded the hustle for a slower life in Mexico City, where she's writing her forthcoming book, “The White Man Within” that reframes every setback along the way as data, not damage.

⁠Bea Arthur, LMHC⁠ is a Columbia University-trained psychotherapist, award-winning entrepreneur, TEDx speaker, and true pioneer in the field of mental health. Bea has been named an Entrepreneur to Bet On by Newsweek Magazine and one of the 100 Most Inspirational New Yorkers by Bumble.

Bea shared her career as a social worker, where she served addicts in recovery, survivors of domestic violence, and students in the New York City public school system. 

She’s always been passionate about lifting people up and decided to scale this gift in the tech world. In 2011, her career took off at the intersection of psychology and technology, when her first startup Pretty Padded Room competed on ABC’s Shark Tank, which put “online therapy” on the map! In 2014, she became the first African-American female founder accepted by Y Combinator accelerator program.

8 years ago, she launched her second startup called The Difference, which was the very first Alexa Skill for easy access therapy.

Now, she’s a first-time author. Her book “The White Man Within”, where she tells her story,  how she created her own path to success, and how you can too! Bea, welcome to the show.

Connect with Bea Arthur

LinkedIn → ⁠http://www.beaarthurtherapy.com⁠ 

Instagram → ⁠https://www.instagram.com/bbarthur/⁠ 

Book Instagram → ⁠https://www.instagram.com/thewhitemanwithin/⁠ 

Book Website → ⁠https://www.thewhitemanwithin.com/⁠ 

Connect with Naomi Haile:

Website → https://www.naomihaile.com/

Newsletter → https://powerofwhy.kit.com/57ca5180df 

Purchase the Purpose Canvas to bring alive your dreams tomorrow: ⁠https://naomiahaile.gumroad.com/l/purposecanvas⁠ 

LOOKING FOR A SPECIFIC GEM?

00:00 Welcome and introduction to Bea Arthur

06:52 Origin story: Ghanaian immigrant family raised in Houston

07:19 Kicked out of school for "talking back"

09:15 How Bea went from real estate to becoming a therapist

14:48 What made her write the book “The White Man Within” now

14:56 Conforming inside the tech world's unequal rules

18:30 Founder vs. CEO?

21:10 Analyze vs. act

23:18 Bea investing online therapy with Pretty Padded Room

33:09 "Strong Seed, Wrong Soil" and the cost of the wrong environment

35:30 Her actual morning practice

37:36 Why Mexico City lowered her stress and sped up the her book writing process

42:33 "Data, not damage" and her father's story about racism in 1980s Texas

44:39 "This is a station, not the destination"

47:09 Performing less and allowing the messy middle

51:17 Reframing "everything happens for a reason"

53:53 The matriarchy reframe (love instead of suffering)

55:59 Doing more of what makes you happy

55:38 Where to find Bea and her book online

Bea Arthur built two startups, landed on Shark Tank, and became the first Black female founder accepted into Y Combinator. Then she hit a wall and decided to finally choose herself. So she traded the hustle for a slower life in Mexico City, where she's writing her forthcoming book, “The White Man Within” that reframes every setback along the way as data, not damage.

Bea Arthur, LMHC is a Columbia University-trained psychotherapist, award-winning entrepreneur, TEDx speaker, and true pioneer in the field of mental health. Bea has been named an Entrepreneur to Bet On by Newsweek Magazine and one of the 100 Most Inspirational New Yorkers by Bumble.

Bea shared her career as a social worker, where she served addicts in recovery, survivors of domestic violence, and students in the New York City public school system. 

She’s always been passionate about lifting people up and decided to scale this gift in the tech world. In 2011, her career took off at the intersection of psychology and technology, when her first startup Pretty Padded Room competed on ABC’s Shark Tank, which put “online therapy” on the map! In 2014, she became the first African-American female founder accepted by Y Combinator accelerator program.

8 years ago, she launched her second startup called The Difference, which was the very first Alexa Skill for easy access therapy.

Now, she’s a first-time author. Her book “The White Man Within”, where she tells her story,  how she created her own path to success, and how you can too! Bea, welcome to the show.

Connect with Bea Arthur

LinkedIn → http://www.beaarthurtherapy.com 

Instagram → https://www.instagram.com/bbarthur/ 

Book Instagram → https://www.instagram.com/thewhitemanwithin/ 

Book Website → https://www.thewhitemanwithin.com/ 

Connect with Naomi Haile:

Website → https://www.naomihaile.com/

Newsletter → https://powerofwhy.kit.com/57ca5180df 

Purchase the Purpose Canvas to bring alive your dreams tomorrow: https://naomiahaile.gumroad.com/l/purposecanvas 

LOOKING FOR A SPECIFIC GEM?

00:00 Welcome and introduction to Bea Arthur

06:52 Origin story: Ghanaian immigrant family raised in Houston

07:19 Kicked out of school for "talking back"

09:15 How Bea went from real estate to becoming a therapist

14:48 What made her write the book “The White Man Within” now

14:56 Conforming inside the tech world's unequal rules

18:30 Founder vs. CEO?

21:10 Analyze vs. act

23:18 Bea investing online therapy with Pretty Padded Room

33:09 "Strong Seed, Wrong Soil" and the cost of the wrong environment

35:30 Her actual morning practice

37:36 Why Mexico City lowered her stress and sped up the her book writing process

42:33 "Data, not damage" and her father's story about racism in 1980s Texas

44:39 "This is a station, not the destination"

47:09 Performing less and allowing the messy middle

51:17 Reframing "everything happens for a reason"

53:53 The matriarchy reframe (love instead of suffering)

55:59 Doing more of what makes you happy

55:38 Where to find Bea and her book online

According to Upwork, 76.4 million Americans are part of the freelance workforce, which grew from 57 million in 2019. And by 2027? This number is expected to rise to over 50% of the U.S. workforce.

Angela Frank is a fractional CMO, growth marketing advisor, and founder of The Growth Directive, a marketing consultancy that helps founders build clear, sustainable marketing strategies that support long-term growth. With a track record of generating over $60 million in revenue for startups and scaling brands, Angela brings a rare combination of in-house operator experience and scrappy entrepreneurial instinct to companies she works with.

Angela's path to consulting was anything but linear. She grew up in a small town in northern Minnesota and the first in her family to pursue a four-year college degree.

She started her first Etsy shop as a sophomore in college, ran a thriving e-commerce business during the pandemic, then pivoted into corporate marketing roles before eventually negotiating her way into a fractional arrangement with her employer.

As you will learn, she proposed they use the money saved to invest in another marketing channel. And for her, she used that freed up time to build her consulting practice. She officially went full-time in her business in 2022.

Angela is the award-winning author of Your Marketing Ecosystem: How Brands Can Market Less and Sell More, which teaches founders and consultants how to build connected marketing systems that drive results without complexity. She also hosts The Growth Pod, a podcast where she shares practical insights on marketing strategy, consulting, and business building.

Her current focus is helping experienced operators and marketers turn their expertise into structured, profitable consulting practices.

Connect with Angela

• LinkedIn: Angela Frank
• Website: The Growth Directive
• Book: Your Marketing Ecosystem: How Brands Can Market Less and Sell More
• Instagram: @angelafrankofficial
• Threads: @angelafrankofficial

Connect with Naomi

• Website: www.naomihaile.com
• LinkedIn: Naomi Haile
• Instagram: @naomiahaile
• YouTube: Naomi Haile
  

Marie Lewis is the founder and CEO of Royal Assistants, an operations-focused executive support company built to help founders lead with clarity and structure. Her journey into business began with service. She was raised in a faith-centered household, she spent years in administrative leadership across church and corporate environments before becoming the person people relied on to bring order to organizations and systems.

Marie started working independently in 2015, taking her first paid role setting up systems for her church, and has spent the decade since building Royal Assistants from a solo virtual assistance practice into a full operations and systems design company with a team behind her. She has hired and released more than 100 people from her business over the years as she refined who she works with and how she delivers what she calls "the royal experience" — a client journey built on intentionality, transparency, and excellence.

Born in Jamaica, Marie's family relocated to New York, where she watched her parents build their own businesses, her father moving from carpentry into full-time ministry and then construction, and her mother building a career as a seamstress before becoming an executive house cleaner. Marie now lives in Atlanta with her husband and their daughter, where she runs Royal Assistants and shares tutorials and systems, including her SuiteDash system, with her audience on YouTube.

She describes her guiding philosophy as one of radical transparency: she does not believe in gatekeeping knowledge, and treats every client relationship as an opportunity to build trust through consistency and care.

Connect with Marie

• Website: Royal Executive Assistants

• LinkedIn: Royal Executive Assistants LLC

• YouTube: @TheRoyalAssistant

• Instagram: @royalassistants

Connect with Naomi

• Website: www.naomihaile.com

• LinkedIn: Naomi Haile

• Instagram: @naomiahaile
• YouTube: @naomiahaile

Soji James is a New York based strength and kettlebell coach, meditation teacher, breathwork facilitator and the founder of the Metta Club. The Metta Club is a mindfulness-based community built around making that inner work feel practical and human.

His practice is built on a conviction most of the fitness industry ignores: that the body and the inner life are not separate projects, and that the people most in need of stillness are usually the ones moving too fast to notice.

Soji grew up in the Bronx, raised by a mother who told him consistently that the pen was always his to hold - that he had the power to write his own story. He found strength training in college at SUNY New Paltz, where he studied biology and played basketball.

During one of the most challenging seasons of his life, meditation and breathwork became the survival tools that helped him through it. After losing his father unexpectedly to a heart attack at 52, and discovering he had no framework to process the grief. That experience reshaped his understanding of what his clients actually need, and what he had needed long before he knew to ask for it

All of his experiences are the foundation of everything he teaches. Soji believes most of us were taught how to go hard, but not how to be still. And his whole philosophy is that you don't have to choose. You can be driven and grounded. You can chase big goals and still know how to pause.

He launched his coaching practice 13 years ago. Today, he works with clients across the country, ranging from executives, surgeons, founders, and parents, and he also leads breathwork and meditation sessions inside companies and organizations.

Connect with Soji

• The Metta Club: www.sojijames.com
• Website: www.sojijames.com
• Instagram: @soji.james1

Connect with Naomi

• Website: www.naomihaile.com
• LinkedIn: Naomi Haile
• Instagram: @naomiahaile
• Twitter: @naomiathaile
• YouTube: Naomi Haile
  

"When you're picking up heavy weights in life and you make the decision to face that weight, there is a confidence that you build." - Almeta Brown

Almeta Brown is a strength coach, therapist in training, and wellness practitioner. Her work lives at the intersection of trauma-informed care, nervous system regulation, and sustainable strength building.

Her approach begins with a question that reorients the entire conversation around health and performance. Not how much the body can endure — but what it means to feel safe, strong, and supported in your own body.

Through trauma-informed strength training, Almeta helps her clients build physical muscle alongside something less often named: resilience, self-trust, and capacity. Everything she teaches comes from her own experience, including competing in bodybuilding shows, which grounds her practice in something beyond theory. Her framework is rooted in the values of intentionality, rest, love, service, community, and health as a lifelong practice — inviting people to slow down, reconnect with themselves, and build systems that work with their bodies and lives rather than against them.

A central thread in her work is redefining what health looks like, particularly within Black communities, and restoring rest to its rightful place as a tool for regulation and sustenance — not a reward earned after exhaustion. She believes the way we care for our bodies mirrors the way we care for our lives and our communities.

As a therapist in training, Almeta brings a treatment-plan mindset to every client relationship. Through an integrated wellness framework that blends strength training, coaching, and mental health–informed support, she works with clients to build personalized plans grounded in both physical and psychological needs — helping them develop capacity not just in their bodies, but in every area of their lives.

Connect with Almeta

• LinkedIn: Almeta Brown
• Website: www.mindandbodymoves.com
• Instagram: @MindAndBodyMoves

Connect with Naomi

• Website: www.naomihaile.com
• LinkedIn: Naomi Haile
• Instagram: @naomiahaile
• YouTube: Naomi Haile