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

SPONSORS
Wise Agent | wiseagent.com — The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.
Subi | oksubi.com — Your AI transaction genie. From contract to close, your work is my command.
The CE Shop | theceshop.com — Online real estate education designed to fit your schedule and keep your career moving forward.

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.

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.

This episode is for every agent who has ever felt like they started too late, had too little, or questioned whether any of it was worth it.

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
6: Her coaching philosophy: don't tell agents what to do, help them give themselves the work
7: Why she has never sold a single property she has owned, and why she wishes she had bought 30 more during the downturn

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 PARTNERS
1:Wise Agent (wiseagent.com)
2: Subi (oksubi.com)
3: The CE Shop (theceshop.com)

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 Partners:
Wise Agent — wiseagent.com
Subi — oksubi.com
The CE Shop — theceshop.com

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/meganvondeylen

Eric Winegard didn't start his entrepreneurial journey until the age of 40. He was making $500,000 a year as a sales leader, living comfortably — and he walked away from all of it. Today, as CEO and co-founder of Rare Blue Moon Marketing, he runs an 8-figure digital marketing agency serving 300+ clients, built alongside his wife, and powered by an unshakeable belief in reinvention.

In this episode of Outside the Corporate Box, JMan and Jeffrey Scott Stanton sit down with Eric for a raw, unfiltered conversation about what it really takes to leave the corporate world and build something of your own.

What You'll Learn:
1: Why commitment is the elimination of options — not a mindset shift
2: The honest truth about 'burn the boats' and why most people aren't ready
3: How Eric's wife pushed him to think far beyond a $2–3M/year ceiling
4: The biggest hiring mistakes he made early on — and how he fixed them
5: Why wealthy buyers ARE on social media, and how to reach them with Facebook Live
6: What Eric would do if his company disappeared tomorrow (his answer will surprise you)

Guest Bio:
Eric Winegard is the CEO and co-founder of Rare Blue Moon Marketing, a South Florida-based digital marketing agency that has scaled to 8 figures and serves 300+ clients across SEO, paid ads, AI automation, and tech stack consulting. A Navy veteran and former top-performing sales leader, Eric started his entrepreneurial journey at 40 and has been building ever since — with no plans to slow down.

TIMESTAMPS:
00:00 — Teaser
01:05 — Introduction & Welcome
01:49 — Who Is Eric Winegard? 8-Figure Agency, 300+ Clients
02:28 — From Single-Mom Household to Entrepreneurship at 40
03:32 — Why He Finally Believed He Could Be a CEO
06:10 — Military Background: Navy, Structure, and Leadership
08:12 — Building With His Wife: The Real Story
10:15 — From $500K/Year Employee to Just Breaking Even
11:55 — What Rare Blue Moon Marketing Actually Does
13:33 — The Biggest Digital Marketing Mistakes Business Owners Make
15:08 — How to Build a Brand From Zero (Free Advice First)
17:19 — What Really Separates Side Hustlers From CEOs
18:33 — Burning the Boats: The Full Breakdown
20:01 — Should You Keep Your Safety Net or Go All In?
22:34 — Did He Ever Think About Quitting?
26:33 — Biggest Failures & What He'd Change
28:07 — Landing High-Ticket Clients: The Social Media Secret
31:03 — If His Company Disappeared Tomorrow...
34:55 — Knowing Your Weaknesses Makes You a Better CEO
35:45 — Favorite Quote: Pound the Rock
37:34 — Closing & Where to Connect

Connect with Eric:
LinkedIn: https://www.linkedin.com/in/eric-winegard-93892717/
Instagram: https://www.instagram.com/ericwinegardofficial/
Rare Blue Moon Marketing Website: https://rarebluemoon.io/

About Outside the Corporate Box: Real conversations with real leaders who broke the mold and built something better. Hosted by JMan (Jeremias Maneiro) and Jeffrey Scott Stanton.

Subscribe so you never miss a Monday. New episodes every week.