Jamie Cornehlsen watched his mutual fund fall from $219 million to $33 million, and he calls it the most expensive education of his life. The business had hit a ceiling, and the fix he eventually found through the Entrepreneurial Operating System (EOS) came down to getting the right people into the right seats.

In this conversation with JMan and Jeffrey Scott Stanton, Jamie traces a problem-solving instinct that started at age eight, when he sold coffee and donuts to drivers stuck in the 1979 gas lines, all the way to his work today helping leadership teams find the answers that are already in the room.

What You'll Learn

• How to find the real bottleneck in your business by asking customers what they are stuck on, the same habit that helped Jamie grow his fund
• Why growth stalls when your team was built for a smaller version of the company, and how to see it before you lose key clients
• How the EOS Identify, Discuss, Solve (IDS) process moves leadership teams past symptoms to the root issue
• What 76 calls to land a single financial advisor taught Jamie about sales and the fear of picking up the phone
• The red flags that tell a business owner they have hit the ceiling
• What to have in place before leaving a credentialed career to build something of your own

About Jamie Cornehlsen

Jamie Cornehlsen is an EOS Implementer who helps business owners and their leadership teams get clear on vision, gain traction, and build healthier teams. A CFA charterholder with an MBA, he started his career in investment banking at Bear Stearns before founding and managing his own mutual fund. He is now based in Rochester, New York, and is writing a book on the EOS Quarterly Conversation.

TIMESTAMPS

00:00 Cold Open
01:48 What EOS Is and What an Implementer Actually Does
03:33 Selling Coffee and Donuts in the 1979 Gas Lines
07:04 Leaving Bear Stearns to Launch a Mutual Fund
08:17 Asking Advisors What They Needed
11:17 The Landscaping Business Lesson
13:50 What the CFA Really Gives You
17:04 Hitting the Ceiling from the Inside
18:44 Right Process Starts with the Right People
19:41 Gino and Floyd Wickman and the Origin of EOS
22:06 IDS and Finding the Root Issue
26:07 The Leap into EOS and the Move to Rochester
29:36 First Client Win: The Dentist Who Got His Life Back
31:39 Learning to Sell and the 76 Call Story
36:34 The Downturn: $219M to $33M
38:40 Is Entrepreneurship Born or Built?
40:35 Crying on the Front Porch
42:11 When a Client Becomes an EOS Implementer
43:40 Connecting People, Purpose and Passion
45:07 Signs You Have Hit the Ceiling
46:13 Advice for Leaving a Credentialed Career
47:02 First Moves with No Network
49:47 Lightning Round
52:17 What Jamie Would Tell His Day One Self
52:38 Jamie's Upcoming Book

Connect with Jamie Cornehlsen

Guest LinkedIn: https://www.linkedin.com/in/jamie-cornehlseneostoronto/
Guest Website: https://implementer.eosworldwide.com/jamie-cornehlsen/

Tip from Jamie: search "EOS Jamie Cornehlsen" to find his EOS Worldwide page.

FOUNDING SPONSORS: 
1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% off

About the Show

Outside the Corporate Box features real conversations with leaders who broke the mold and built something better, hosted by JMan and Jeffrey Scott Stanton. Every Monday, a new guest shares how they reinvented their career and what they learned along the way.

Subscribe and turn on notifications so you never miss a Monday conversation.

Ivan Estrada spent years hiding his Latino heritage and his identity as a gay man from his own real estate clients, convinced it would cost him business in Beverly Hills. Then he found out the opposite was true. In this episode, the Beverly Hills broker and author of Brand with Purpose breaks down how concealment quietly kills trust, and how becoming fully himself is what actually helped him sell $750 million in real estate.

What You'll Learn

1: Why hiding parts of your identity from clients creates a wall that blocks the trust a sale depends on
2: The real sequence behind Ivan's turnaround: authenticity came first, and the success followed
3: How to build a personal brand around fixed values instead of chasing whatever is popular that week
4: Why a strong brand should intentionally repel the wrong-fit clients, not just attract everyone
5: How Ivan uses AI as a creative and marketing multiplier without losing the relationship work that actually closes deals
6: What changed for Ivan once his sales crossed the $750 million mark, and what he is building next

Guest Bio

Ivan Estrada is a Beverly Hills luxury real estate broker with Douglas Elliman, a TEDx speaker, and the author of Brand with Purpose. Before real estate, he was a signed recording artist as a child and later worked as a CPA. Over more than a decade in one of the toughest luxury markets in the country, he has closed more than $750 million in sales and now runs Beige Atlas, his own real estate market report.

TIMESTAMPS
00:00 - Cold open: the story you hide might be the story that builds trust
01:30 - Meet Ivan Estrada
02:23 - Signed as a child performer, then a lawsuit ends it at 17
08:06 - USC, finance, and the "safe" fallback plan
11:25 - Choosing to be let go, and the freedom that followed
13:19 - Finding real estate through Million Dollar Listing
24:59 - Breaking into Beverly Hills without the "right" background
27:41 - The turning point: hiding his heritage and identity from clients
34:13 - Brand as a magnet: what it should attract, and what it should repel
42:39 - Using AI to multiply creative output without losing the human touch
48:23 - The real number: $750 million in career sales, and its hidden cost
51:34 - What matters now: legacy, mentorship, and representation
55:09 - Final question and where to find Ivan

Connect with Ivan Estrada
Guest LinkedIn: https://www.linkedin.com/in/ivanestradaproperties/
Website: https://ivanestrada.com/
Instagram: https://www.instagram.com/therealbrandwith/

FOUNDING SPONSORS: 
1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% off

About the Show:

Outside the Corporate Box features founders and professionals who left the expected path to build something of their own, hosted by JMan and Jeffrey Scott Stanton.

New episodes every Monday. Subscribe so you never miss a reinvention story.

Tezeta "Tez" Roro had everything the blueprint promised: the MBA, the six-figure salary, the recognized company name on her badge. She was so proud of that job she wore her badge to the grocery store. Then came 10:00 PM on a corporate campus, nine months pregnant, working through a capital budget crunch, and the moment she realized the structure she had spent 12 years climbing was fundamentally incompatible with the life she was actually trying to live.

What she did next took two and a half years of calculated planning, a Forbes article documenting every step, and the courage to go from a guaranteed salary to 100% commission as a first-gen immigrant with a toddler, a newborn, and a husband consulting out of state three weeks a month. Today Tez is a broker-owner, speaker, and founder of Yourtopia Realty Partners. This is her story.

What You Will Learn:

1: Why the "golden handcuffs" of a six-figure salary are often worth less than they appear once you calculate taxes, commute, stress, and lost time
2: How Tez structured a deliberate two-and-a-half-year exit strategy as a risk-averse introvert with no safety net behind her
3: The difference between mourning a corporate identity and finding confidence in a new one
4: Why she used a six-month maternity leave to test whether she could actually sustain the real estate lifestyle before fully committing
5: Practical financial strategies for leaving corporate when you have a mortgage, kids, and no trust fund
6: What it really means to define success on your own terms, and why middle schoolers gave her a standing ovation

About Tezeta Roro:

Tezeta "Tez" Roro is a broker-owner, speaker, and founder of Yourtopia Realty Partners. A first-generation Ethiopian-American with a biology degree, MBA, and 12 years in corporate operations, Tez documented her exit strategy in Forbes and has since built a brokerage and property management company simultaneously. She speaks nationally on entrepreneurship, real estate, and building a business that aligns with your values.

TIMESTAMPS:
00:00 — Introduction: The parking lot moment
01:00 — Painting the picture: 12 years inside corporate
03:00 — The risk-averse introvert and what that actually means
04:30 — The immigrant path: biology, MCATs, and the pivot to business
07:00 — The cracks appear: parenting inside a corporate structure
10:00 — The RSV hospitalisatio and the conversation that changed everything
14:00 — Nine months pregnant, 10:00 PM, hitting a deer in the parking lot
17:00 — The second maternity leave that became her launch runway
19:00 — "We get married to the top-line salary" -- the real numbers breakdown
22:00 — What to do if you have no partner safety net
24:00 — The rebuild: identity shifts, isolation, and finding the new version
28:00 — Why real estate and the ding-ding moment during her own home purchase
31:00 — The introvert-extrovert misunderstanding and entrepreneurial risk appetite
35:00 — Letting go vs. mourning: how to leave without grief
38:00 — Lightning Round
41:00 — The Last Question: advice for anyone about to bet on themselves

Connect with Tezeta Roro:

LinkedIn: https://www.linkedin.com/in/tezroro/
Forbes Article: https://www.forbes.com/sites/ellevate/2019/07/31/plotting-your-corporate-exit-strategy/

FOUNDING SPONSORS:
1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% off

SUBSCRIBE to Outside the Corporate Box for new episodes every Monday.

Outside the Corporate Box is part of J Squared Podcast Productions — a premium media network built for professionals who want more than entertainment.Read the full episode breakdown: https://jmanai.com/she-had-the-mba-the-six-figure-salary-and-was-crying-in-a-parking-lot-at-10-pm-tezeta-roro/

Jackie Phichith spent nearly two decades inside Fortune 500 boardrooms helping McDonald's, Merck, and Pfizer navigate transformation. Then she realized the framework she had been teaching organizations was the same one she needed to apply to herself. What she learned next might change how you think about the career decision you are sitting on right now.

What You'll Learn:

1: Why 70% of enterprise transformations fail and the one thing companies keep cutting that guarantees it
2: The SHINE framework: a 5-step method for moving any team through change without losing people
3: What the Midnight Rambles of Teddy Roosevelt teach us about effective leadership in 2025
4: How to do a quarterly business review on yourself when you're a founder of one
5: Why employee engagement scores are not soft data and what happens when leadership ignores them
6: The identity shift nobody talks about when you leave a corporate title behind

About Jackie Phichith:
Jackie Phichith is a change management strategist, keynote speaker, and founder of Inspiration Your Way. With nearly 20 years inside Fortune 500 companies including McDonald's, Merck, and Pfizer, she has developed the SHINE framework to help leaders and organizations move through transformation without losing their people. She now brings that expertise to a broader stage, working with executives and founders across industries.

TIMESTAMPS:
00:00 — Cold open and episode introduction
01:00 — What 20 years inside Fortune 500 companies actually looked like
03:30 — Why only 27% of employees trust their leaders to guide them through change
07:00 — The real reason companies cut training during transformations
08:30 — The moment Jackie knew she had to step outside the corporate box
13:00 — How staying comfortable becomes the biggest risk
15:00 — The identity shift of going from corporate employee to founder
20:00 — How to protect your focus as a solo founder
24:00 — Running a quarterly business review on yourself
28:00 — The Teddy Roosevelt Midnight Rambles story and what it means for CEOs
31:00 — The organizations that will be left behind by AI and rapid change
38:00 — The SHINE framework explained step by step
44:00 — Lightning Round
46:00 — The Last Question: What would you go back and tell yourself on day one?

Connect with Jackie Phichith
Guest LinkedIn: https://www.linkedin.com/in/jacquelinephichith/

About the Show:
Outside the Corporate Box is a Monday podcast co-hosted by JMan and Jeffrey Scott Stanton. Every episode explores what happens when ambitious professionals step beyond traditional titles and build something on their own terms. Real stories about reinvention, risk, and what it actually takes to bet on yourself.

FOUNDING SPONSORS:
1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% off

SUBSCRIBE to Outside the Corporate Box for new episodes every Monday.

Outside the Corporate Box is part of J Squared Podcast Productions — a premium media network built for professionals who want more than entertainment.Read the full episode breakdown: https://jmanai.com/why-70-of-corporate-transformations-fail-and-what-leaders-can-do-about-it/

Lauren Dunkle Dlugosh was one of the top billing recruiters at her firm in Rochester, regularly placing $550K to $650K in fees annually. She had great colleagues, a strong reputation, and no real reason to leave. And the night before she quit, she slept perfectly.

That is what this conversation is really about. Not the business plan or the LinkedIn announcement. The moment before all of it, when everything felt right even though nothing was certain yet.

What You Will Learn:
1: What a non-solicitation agreement actually means and what it costs you when you walk away from a decade of client relationships
2: Why Lauren named her first year of entrepreneurship grief, and how that honesty made her a better founder and recruiter
3: How the golden handcuffs concept applies beyond recruiting and how to know when the cage is no longer worth it
4: What Lauren's cross-country camper van trip has to do with landing a client after she went independent
5: The one reframe that shifted everything: it was not about what she was running from, it was what she was running toward
6: Why Lauren went from being a doer at her old firm to a creator building her own

TIMESTAMPS:
00:00 — Introduction & The Hook
00:42 — Guest Introduction: Lauren Dunkle Dlugosh
01:10 — Life Before Relay: The Rochester Firm
04:22 — The Slow Burn: When Fine Stops Being Enough
05:11 — AI in Recruiting: What Lauren Wanted to Build
10:20 — Non-Solicitation Agreements Explained
12:50 — Golden Handcuffs: The Cost of Comfort
15:16 — Life With Intention: The Camper Van Trip
17:03 — The Loneliness Nobody Talks About in Year One
21:05 — Grieving a Life You Actually Loved
24:43 — Stopping Waiting for Permission
27:48 — Lightning Round
33:25 — The Last Question: What Would You Tell Yourself on Day One?
34:07 — Outro

About Lauren Dunkle Dlugosh:
Lauren Dunkle Dlugosh is the Founder and CEO of Relay Recruiting, an executive and professional search firm based in Rochester, New York. With nearly a decade of experience recruiting across nonprofit, higher education, manufacturing, energy, and the C-suite, she built her reputation as a top billing recruiter before launching independently. Her work combines deep relationship-based search with a forward-thinking approach to AI and workflow efficiency.

Connect with Lauren Dunkle Dlugosh
Guest LinkedIn: https://www.linkedin.com/in/laurendunkle/
Website: https://www.relayrecruiting.com/

FOUNDING SPONSORS:
1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% off

SUBSCRIBE to Outside the Corporate Box for new episodes every Monday.

Outside the Corporate Box is part of J Squared Podcast Productions — a premium media network built for professionals who want more than entertainment.Read the full episode breakdown: https://jmanai.com/leaving-corporate-to-build-relay-recruiting-lauren-dunkle-dlugoshs-story/

Donna Baker spent 30 years climbing the corporate ladder as an executive assistant — all the way to one of the highest-paid roles in Los Angeles. She was brilliant, organized, and on the verge of becoming a paper millionaire through stock options at an internet incubator.

Then the Nasdaq crashed in 2000, and within seven months she had no job and no stock.

At 50 years old, she got into real estate with zero clients, zero guaranteed income, and zero experience in sales. In seven months, she was the #1 agent in her office. She has held that title every year for 25 years.

In this episode of Outside the Corporate Box, Donna sits down with JMan and Jeffrey to talk about what it actually feels like when the floor falls out, why her corporate background was her biggest competitive advantage, and what she wishes someone had told her at 49.

What We Cover:
1: How Donna turned 30 years of corporate experience into a real estate competitive advantage
2: The emotional reality of being laid off when you were at the top of your game
3: Why she built a website and started direct mail marketing before she had a single client
4: The floor time strategy that turned cold foot traffic into loyal buyers
5: How she pivoted her brand from 'historic home specialist' to 'mobile homes to mansions'
6: Why she believes entrepreneurship is in the blood — and the pushback she gets for saying it
7: The litmus test she'd give anyone thinking about leaving the corporate world
8: What it means to be 75, covered in tattoos, with purple hair, and still dominating her market

Chapters:
[00:00] Cold open — Donna's story in 60 seconds
[01:00] Welcome + full guest introduction
[02:00] Growing up wanting to be a secretary — career beginnings in the 1960s-70s
[05:00] The Staten Island insurance broker who changed everything — her first true mentor
[09:00] From Bell + Howell to direct mail marketing — how each job stacked her skills
[13:00] Climbing to the internet incubator — and why she said yes to the dot-com world
[15:00] The Nasdaq crash, the lost stock options, and the silence that followed
[17:00] A car ride through Bakersfield — the moment real estate entered the picture
[20:00] Getting licensed, getting hired before the license arrived, and closing in month three
[25:00] Her first commission reinvested into a green termite flyer — and how it worked
[29:00] Number one agent in seven months — the floor time and CRM strategy behind it
[37:00] 51 transactions in a year, building a team, and knowing when to hire help
[40:00] Is entrepreneurship nature or nurture? JMan pushes back
[48:00] Lightning round — myths, secret sauce, and what she'd tell herself at 49
[51:00] 75 years old, purple hair, tattoos, and still closing — why her brand works
[55:00] AI, technology, and why refusing to learn it is the real career killer
[57:00] Where to find Donna + closing thoughts

Guest Bio:

Donna Baker is a top-producing REALTOR and co-founder of the Ammon + Baker team at JohnHart Real Estate in Monrovia, California. She has ranked number one in every office she has worked in for 25 consecutive years.

Before real estate, Donna spent three decades as an executive assistant to presidents and CEOs across Southern California's most technical industries — including Bell + Howell and an engineering software firm with nearly 900 employees. She was among the highest-paid EAs in Los Angeles until the Nasdaq crash ended her career overnight.

She earned her real estate license at 50 with no sales experience and closed her first two transactions within a month. A self-taught technologist, she built her own website before listing her first property.

A Monrovia resident for the past forty years, Donna served as Historic Preservation Commissioner, earned the Chamber Citizen of the Year Award, and traveled to Thailand to build homes through the Carter Work Project. She specializes in residential properties across the San Gabriel Valley, with a passion for historic and vintage homes.

At 75, Donna Baker is still the one to beat.

Connect with Donna Baker:
Website: ammonandbaker.com
Linkedin: https://www.linkedin.com/in/donnabaker
Instagram: @realtordonna
Facebook: facebook.com/4SaleByDonna

FOUNDING SPONSORS:
1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% off

SUBSCRIBE to Outside the Corporate Box for new episodes every Monday.

Outside the Corporate Box is part of J Squared Podcast Productions — a premium media network built for professionals who want more than entertainment.Read the full episode breakdown: https://jmanai.com/laid-off-at-50-1-agent-at-51-donna-baker-on-reinventing-after-the-floor-falls-out/

Most episodes of Outside the Corporate Box feature guests who stepped away from someone else's structure to build their own thing. This one is different.

This week, JMan and Jeffrey Scott Stanton turn the mic on themselves.

For over a decade, Jeffrey was the Executive Vice President of Learning and Development at Douglas Elliman Real Estate, shaping the careers of 6,000 to 7,000 agents across one of the most recognized luxury brands in the country. JMan built his reputation as a national trainer inside that same ecosystem. Their professional identity was inseparable from the institution.

Then the floor disappeared.

In this founders episode, both hosts share what it actually felt like when that chapter ended, not the polished version, but the gut-punch version. They talk through the grief, the loneliness when the phone stops ringing, the strange moment when you realize some of those industry friends were never really friends. And then they get into what happened next.

This is an honest conversation about what it costs to go all-in on a company identity, and what it requires to rebuild yourself on the other side.

"I woke up every morning saying, this is what I love doing. And then when that stops, either by choice or if it is taken away from you, that hurts." — Jeffrey Scott Stanton

Topics covered in this episode:
1: What it means when your work becomes your entire identity
2: The visceral emotional experience of losing a role you loved
3: Why the phone going quiet is one of the hardest parts
4: Learning who your real friends are when the title is gone
5: Why comfort is the most addictive thing in the world
6: How pressure builds diamonds, and why some people need it to perform
7: What discipline means when you are building something for yourself
8: The one thing both hosts would tell themselves five years ago

This is the episode that started the whole conversation. If you have been sitting on the edge of something, watching the writing on the wall, or just trying to figure out what comes next after a major disruption, this one is for you.

Timestamps
00:00 - ElevenLabs intro and show open
00:12 - Jeffrey describes his decade at Douglas Elliman and what that professional identity meant
02:43 - JMan reflects on being pulled into the corporate box from an entrepreneurial background
06:32 - The week before everything changed: what both expected for the next five years
07:57 - The moment: gut punch, betrayal, grief, and the silence that followed
11:19 - Business is personal: working through the stages of loss after leaving a role
13:20 - The phone goes quiet: the part nobody talks about when you leave a job
15:21 - Identity and title: how you find out who your real friends are
16:08 - Burn the boats: why having no other option can be the greatest accelerator
19:34 - Pressure builds diamonds: performing best when there is no safety net
21:26 - Discipline beats everything: what entrepreneurship actually requires
23:08 - The message for the listener: the person with one foot in each world
25:13 - Would you go back? Do you wish it never happened?
28:05 - The Last Question: what would you tell yourself five years ago
29:27 - JMan closes: doing what you love, serving people, and doing it anywhere
30:41 - Outro, sponsor close, and call to action

Connect with the Hosts
JMan (Jeremias Maneiro): LinkedIn: https://www.linkedin.com/in/jmansells/
Jeffrey Scott Stanton: LinkedIn: https://www.linkedin.com/in/jeffreyscottstanton/

FOUNDING SPONSORS:
1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% off

SUBSCRIBE to Outside the Corporate Box for new episodes every Monday.

Outside the Corporate Box is part of J Squared Podcast Productions — a premium media network built for professionals who want more than entertainment.Read the full episode breakdown: https://jmanai.com/we-were-the-corporate-box-jman-and-jeffrey-get-honest-about-the-day-everything-changed/

She started at the front desk of a small-town brokerage in 2005, took a pay cut to do it, and had no idea she'd still be there 20 years later — as co-broker owner.

Lindsay Hart is a licensed REALTOR and Co-Broker Owner at RE/MAX in Ithaca, New York, and the host of the podcast Under Contract Taking Backup. In this episode, Lindsay joins JMan and Jeffrey Scott Stanton on Outside the Corporate Box to talk about the slow, unsexy path from office admin to brokerage partner — and why that path built her in ways no shortcut ever could.

She breaks down what really made her leave a steady paycheck (it wasn't confidence, it was her husband and a savings account), how she built Hart & Homes from a solo act to a six-person team by accident, and the one philosophy that runs every decision she makes inside the brokerage.

She also gets honest about fake-extortion, bad reviews, confrontation, COVID killing her brokerage launch, and what she tells herself when business gets slow.

If you've ever wondered whether the slow path is the right one — this one's for you.

CHAPTERS:

00:00 – Cold Open
07:00 – Before Real Estate: Ithaca, Waitressing, and the Table That Changed Everything
13:00 – Learning the Hard Way: Subcontractors, Taxes, and Crying in Front of a CPA
17:00 – Sold on Real Estate: The Day a Broker Asked Her for a Job
24:00 – Starting From the Bottom Up: What the Front Desk Teaches You
31:00 – Why She Actually Left the Steady Paycheck
36:00 – Bad Reviews, Extortion, and the Art of Not Addressing Everything
43:00 – Building Hart & Homes: A Team That Found Her
47:00 – Relationships Before Business: The Philosophy That Runs Everything
52:00 – From Team Leader to Co-Broker Owner — and Then COVID
01:02:00 – What Centers Her When Things Get Slow
01:07:00 – The Last Question: What Would You Tell Yourself on Day One?

GUEST:
Lindsay Hart is a licensed REALTOR and Co-Broker Owner at RE/MAX in Ithaca, New York. She has spent two decades building her business from the ground up — starting as an office administrator in 2005, earning her license in 2007, launching her team Hart & Homes in 2017, and becoming co-broker owner alongside Melissa Miller in 2020. She is also the co-host of Under Contract Taking Backup, a podcast covering real estate, taxes, and life as a working agent.

Find Lindsay:
Website: LindsayHartRealtor.com
Linkedin: https://www.linkedin.com/in/lindsayhart/
Radio Show: Knock Knock Property Talk — WHCU 607 News Talk Radio, Saturdays at 9:30 AM

FOUNDING SPONSORS:

1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% off

SUBSCRIBE to Outside the Corporate Box for new episodes every Monday.

Outside the Corporate Box is part of J Squared Podcast Productions — a premium media network built for professionals who want more than entertainment.Read the full episode breakdown: https://jmanai.com/from-admin-to-co-broker-owner-lindsay-hart-on-relationships-risk-and-real-estate-reinvention/

She walked away from a tech career, raised her kids while working weekends for a builder, and built her real estate business with doorknob bags and laundromat flyers because she had no marketing budget. Twenty-nine years later, Carrie J. Little is a managing broker in Illinois and Florida, a national speaker, bestselling author, and one of the most trusted educators in real estate technology.

In this conversation with JMan and Jeffrey Scott Stanton on Outside the Corporate Box, Carrie pulls back the curtain on the parts of her journey she has never shared publicly, including a pre-foreclosure during her divorce in 2008, returning to corporate work at McDonald's East Coast Real Estate division just to keep the lights on, and the 12-month exit plan she built before anyone knew she was leaving her brokerage.

What You Will Learn in This Episode:

1: How Carrie got into tech through her identical twin sister and accidentally landed in real estate via a builder's model home
2: The "renting is hazardous to your wealth" flyer strategy that built her entire first client base with zero marketing budget
3: Why she says the smartest, brokest agents are the ones who won't pull the trigger on anything
4: How she nearly lost her home in 2008 and what her step-by-step approach to navigating pre-foreclosure looked like from the inside
5: The 12-month exit strategy she quietly built before leaving her franchise brokerage and opening her own

Timestamps
00:00 — Cold open and sponsor intro
01:00 — Guest intro: Who is Carrie J. Little
02:00 — The tech career origin story: from Sears to NEC Technologies via her identical twin
06:30 — How editing television for a megachurch in the 90s shaped her skill set
07:00 — The builder model home job that pulled her into real estate
10:00 — Getting licensed in 2001 with one goal: $60,000 a year and summers at the pool
12:00 — Closing three deals before 9/11 and what "hustle" actually looked like
15:00 — Family, twins, and why her sister's house deal taught her to lead with referrals
17:00 — Where the teaching instinct comes from and why she coaches differently
22:00 — Every life experience is a professional asset (yes, including McDonald's)
27:00 — How she marketed with zero budget: doorknob bags, laundromat flyers, and Bible study groups
31:00 — Becoming a broker owner: the 12-month exit plan nobody saw coming
35:00 — Going from 2 agents to 50 and learning to lead through standards, not control
38:00 — How she runs her business today: printing checklists, structured days, and ADHD ownership
39:00 — The coaching philosophy: give yourself the work or hope for it
42:00 — The Deeper Cut: almost losing her house to pre-foreclosure in 2008
47:00 — The personal sacrifice she would do differently if she could go back
49:00 — One thing she would tell her younger self: buy property, every time
51:00 — The Last Question: advice for anyone about to bet on themselves
52:00 — Where to find Carrie + outro

Carrie J. Little is a managing broker in Illinois and Florida, founder of Smart Girl Media, national real estate speaker, and bestselling author. With nearly 30 years in the industry, she is one of the most trusted voices in real estate technology and education.

Where to Find Carrie:
Website: https://www.smartgirlmedia.com/
Linkedin: https://www.linkedin.com/in/carriejolittle/

FOUNDING SPONSORS:

1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% offRead the full episode breakdown: https://jmanai.com/she-almost-lost-it-all-how-carrie-j-little-built-29-years-of-real-estate-success-from-nothing/

Megan VonDeylen got into real estate in 2008 during the market crash. She built her business over ten years, reached the top of her brokerage, then walked away because her family needed her. She went back into corporate, turned around departments faster than anyone expected, got passed over anyway, and then walked away again.

The second time she returned to real estate, she made one decision that changed everything: she was going to do it as herself.

No cardigans. No slipping into the persona her first broker told her to wear. Ball cap, boots, tattoos, and the kind of honest client communication that comes from someone who isn't spending energy managing their image.

In this episode, Megan and the hosts talk through what it actually costs to rebuild something from scratch, why imposter syndrome hits hardest when you're most qualified, how she built a veteran-focused niche out of personal experience rather than marketing strategy, and why she's still working through the ceiling she built for herself inside her own brokerage.

This is not a highlight reel conversation. This is what building looks like in the middle of it.

Chapters:
00:00 — Intro & Sponsor Welcome
00:41 — Megan's Origin Story: Real Estate in 2008
03:38 — The First Exit: Corporate, PTSD, and Stability
09:46 — The Second Corporate Run: Materials Management & Glass Ceilings
14:36 — Coming Back: Who She Was vs. Who She Became
19:07 — Results as Security: Leading from Shared Success
22:27 — Why She Left Corporate the Second Time
26:35 — Veteran Real Estate & Serving Those Who Served
34:27 — The Real Cost of Building a Business
36:29 — Imposter Syndrome, Self-Imposed Ceilings & Growing the Brokerage
45:28 — The Last Question: What She Would Tell Herself on Day One
46:17 — Where to Find Megan

FOUNDING SPONSORS:

1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% off

Outside the Corporate Box airs every Monday on all major podcast platforms and YouTube. Share this episode with someone who is in the middle of their own reinvention moment.

Guest Bio:
Megan VonDeylen is the broker and owner of Stone Realty Group in Michigan, a real estate educator, and a specialist in veteran homeownership. She entered real estate in 2008, built her career through two departures and two returns, and launched her own brokerage after nearly two decades in the industry. She holds a degree in accounting and a degree in finance and business management, both earned while simultaneously selling real estate, raising three children, and managing her household through her husband's combat PTSD. She mentored multiple agents to six-figure GCI in their first year and one to seven-figure GCI within five years. She is also a co-founder of a youth rodeo operation and an active advocate for veteran homeownership.

Connect with Megan: https://meganvondeylen.com/
Linkedin: https://www.linkedin.com/in/meganvondeylenRead the full episode breakdown: https://jmanai.com/she-left-real-estate-twice-the-second-time-she-did-it-her-way-megan-vondeylen/