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Guest Bio: Green Bay Greg leads Dallaire Realty, an independent brokerage in Green Bay, Wisconsin, that he founded in 2011 after getting licensed in 2006. His team of 14 agents and three full-time support staff has averaged 400 to 500 units sold per year over the last decade, with over half of that business coming from past clients and referrals.

Episode Summary: Green Bay Greg joins Tim Donovan to break down how his small but highly productive team built a business that runs circles around industry averages without chasing headcount. He gets candid about time management struggles, his personal accountability philosophy he calls the grenade rule, and why he still believes in phone calls and human follow-up over AI and social media for converting leads.

What's Covered:

• Greg explains his team structure of 14 agents and 3 full time support staff averaging 400 to 500 units sold per year for the last decade, built by saying no far more often than yes to new agents
• He traces his path from playing online Texas Hold'em and partying early in his career to getting serious about real estate after meeting his wife and having a daughter, crediting a tech and computer background passed down from his father
• Greg describes investing heavily in relationship building over the years including a five figure vineyard event for over 500 people, and explains that 51 percent of his business still comes from past client sphere despite his reputation as a technology focused team
• He details his lead generation history starting with an expensive early Boomtown subscription in 2014 that changed his business, plus current diversified sources including Zillow, PPC, organic content, and Facebook, while openly discussing quitting social media using a device called Brick for his own mental health
• Greg lays out his follow up philosophy of calling inbound leads without aggressive ten day pounding campaigns, relying on remarketing and retargeting, and stresses that every call needs a clearly defined next step to increase appointment to closing conversion
• He shares his self accountability rule he calls jumping on the grenade, meaning immediately handling any client issue before it festers, and closes with his magic wand answer of wanting a steady flow of high quality non referral seller leads plus a tactical tip to get organized in a CRM and mine personal contacts for a database

Timestamps:

00:00:47 - Greg's origin story getting licensed in 2006 and playing online poker before taking real estate seriously

00:03:10 - Team structure breakdown, 14 agents, 3 staff, and refusing to be a body count business

00:05:20 - The Seth Godin tribe philosophy and hosting a five figure vineyard event for 500 people

00:08:30 - A day in Greg's life including accountability meetings with Tandan and staying hands on with systems

00:12:37 - Time management honesty, working on heaters, and the grenade rule for accountability

00:15:53 - Boomtown history, becoming a peer coach, and diversified current lead sources

00:20:19 - Quitting social media with the Brick device and discussing mental health in real estate

00:21:51 - Follow up philosophy, avoiding aggressive pounding, and using behavioral retargeting data

00:26:17 - Why accountability and clearly defined next steps drive conversion, citing the 5.6 percent stat

00:30:14 - The magic wand answer, wanting a steady flow of high quality seller leads and yearly market reviews

00:32:16 - Tactical advice for agents wanting to grow, get organized with a CRM and mine your contacts

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Guest Bio: Herman Antonov leads The Antonov Group, an 18-agent real estate team based in Minnetonka, Minnesota. He got his start over a decade ago writing SEO blogs about owner financing and bad-credit home buying before becoming licensed, and today his team closes roughly 200 to 220 transactions a year while he focuses primarily on lead generation.

Episode Summary: Herman Antonov joins Tim Donovan to trace his unusual path into real estate through blogging and Google AdSense, then breaks down how his team generates leads today through multilingual social media campaigns and down payment assistance offers. The conversation covers his follow-up philosophy, tactical advice for brand-new agents and agents looking to scale, and his take on how AI and industry consolidation will reshape real estate over the next five years.

What's Covered:

• Herman explains how he stumbled into real estate around 2010 through WordPress blogs targeting searches like rent-to-own and owner financing after the 2008 crash, eventually getting licensed at his mother's suggestion to serve the leads he was already attracting.
• He details his current team structure of 18 agents producing 12 to 20 deals each for a total of about 200 to 220 transactions annually, and how he has scaled back his own production to focus on lead generation.
• Herman describes a multilingual Instagram and Facebook ad strategy built around Minnesota's 32,000 dollar first-generation homebuyer down payment assistance program, noting that a Ukrainian-language video hit 130,000 views while an identical English version barely moved.
• He shares his follow-up philosophy of getting leads offline as fast as possible, using localized storytelling emails as a drip campaign, and acknowledges that leads still fall through the cracks despite these systems.
• For agents starting from scratch in a new city, Herman recommends joining the brokerage with the most listings, partnering with listing agents to host open houses, and generating free leads through Instagram walkthroughs and Facebook Marketplace posts.
• He outlines his biggest wish for the business, solving appointment setting at scale, contrasting agents given raw lead lists versus agents handed pre-booked appointments, and describes using ChatGPT and ElevenLabs to mass-produce faceless video walkthroughs for Instagram.

Timestamps:

00:00 - Intro and welcoming Herman Antonov

00:30 - How Herman got into real estate through Craigslist and blogging

02:38 - Team size and annual transaction volume today

04:58 - Instagram lead generation strategy overview

05:29 - Ukrainian-language video hits 130,000 views

08:08 - Down payment assistance ad targeting first-generation buyers

09:17 - Follow-up philosophy and drip email strategy

11:08 - Building a business from scratch in a new city

14:06 - Tactical advice: get a showing partner and specialize

17:00 - Magic wand problem: fixing appointment setting

20:06 - Using ChatGPT and ElevenLabs for AI video walkthroughs

23:18 - Predictions for the industry five years out

26:20 - Where to follow Herman and his team

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Guest Bio: Casey McCoy is a real estate team leader with Keller Williams based in Evansville, Indiana, running a five-agent team that has grown roughly 50 percent year over year for the past three years. He got his start in real estate after a rough experience buying his first house at age 20, which led him to get licensed in 2010, and he has since built a business rooted in investment income, relationship-first client acquisition, and early adoption of AI tools.

Episode Summary: Casey McCoy joins Under Contract to share the winding, almost accidental path that led him from a foreclosure-threatened house hack at 20 years old into building a thriving real estate team in Evansville, Indiana. He dives into the mentorship moment that reshaped his entire business model, his relationship-first approach to lead generation and follow-up, and how he is already using AI tools like Claude to build custom real estate technology on the cheap.

What's Covered:

• Casey recounts buying his first house at 20 with three lined-up roommates, only to end up in foreclosure and upside down on the mortgage after a botched roof repair and a market crash, which unexpectedly pushed him into getting his real estate license
• He credits mentor Mike McCarthy with two pivotal lessons that changed his business: hiring help early by asking 'why are you stealing someone else's joy' and building investment income so he never has to pressure a client to transact
• Casey explains his go-to strategy for starting over in a new city with no database, which centers on visiting locally owned coffee shops to get introductions to well-connected community members, plus working expired listings for faster results
• He details his personal lead sources, including ditching business cards entirely to control follow-up timing, a Zillow partnership that converts about one in five leads into referrals, and strategic Thursday open houses paired with 100-door neighborhood knocks
• Casey identifies follow-up in the middle of his funnel as his single biggest current business problem despite explosive top-of-funnel growth, and shares client feedback showing people actually want to be followed up with rather than feeling bothered
• He shares his history experimenting with AI-driven real estate technology, from a $25,000 nine-month platform build in 2014 to recreating similar functionality in a weekend for about $50 using Claude, plus his vision for a client-facing AI assistant trained on his own conversations and local market knowledge

Timestamps:

00:00:39 - How Casey got into real estate after running out of college money

00:03:37 - The roof repair that never happened and led to foreclosure

00:06:03 - Getting licensed with his last $500

00:08:06 - Mentor Mike McCarthy and the turning point conversation

00:10:50 - Why are you stealing someone else's joy, the hiring lesson

00:12:46 - What Casey would do first starting over in a new city

00:17:09 - Why Casey stopped using business cards

00:19:08 - Zillow partnership and referral conversion rates

00:22:14 - Casey's follow-up philosophy and building relationships over transactions

00:26:51 - The one problem Casey would fix with a magic wand: follow-up

00:31:53 - Casey's early AI platform build in 2014 versus rebuilding it in a weekend with Claude

00:36:03 - Using AI-powered seller updates to guide price reduction conversations

00:38:04 - Casey's vision for a personal AI assistant trained on his own client conversations

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Guest Bio: Katherine Kiernan is a third-generation banker turned real estate broker who owns Aspire Realty in the Fargo-Moorhead market spanning North Dakota and Minnesota. After a decade in retail banking and investment management, she got licensed almost by accident while trying to sell her own house, and has since built a 12-year, boutique-style brokerage known for concierge-level client care. She also leads physician relocation tours for a major regional hospital system and runs Aspire alongside her husband, who owns a competing brokerage.

Episode Summary: Katherine Kiernan joins Tim Donovan to unpack how her banking background shaped a client-first philosophy that treats a $50,000 condo buyer with the same care as a $5 million commercial client. She shares why she deliberately shrank her team instead of scaling it, her rapid-fire but low-pressure lead follow-up system, and how she uses multiple AI tools as a business partner without losing the human touch that built her referral-driven business.

What's Covered:

• Katherine explains her unlikely path into real estate, starting as a third-generation banker at Merrill Lynch and Wells Fargo before a move to Fargo for family reasons led her to get licensed just to sell her own poorly-fitting house
• She discusses the wild interest rate swings she's lived through as an agent, from 3 percent back up to 6 percent almost overnight, and how her finance background lets her educate clients on locking in now and refinancing later rather than waiting for rates to drop
• Katherine lays out her exact game plan for starting over in a brand new city with no database, prioritizing professional networking groups and local business partnerships with funeral homes, divorce attorneys, and estate attorneys over paid leads
• She details the banking-rooted philosophy behind pouring equal marketing resources into every listing regardless of price point, explaining why treating every client like a paycheck kills long-term referral business
• Katherine describes her deliberate decision to shrink Aspire Realty from a larger team model down to three agents and an admin staff so she can refocus fully on client experience instead of recruitment and growth for its own sake
• She breaks down her lead follow-up philosophy of contacting leads within two minutes but never overwhelming them with repeated calls, and shares how she uses multiple AI tools like ChatGPT, Claude, Grok, and Gemini for listing rollouts, financial projections, and unbiased business feedback while keeping human relationships central

Timestamps:

00:53 - How Katherine accidentally got into real estate

05:03 - Living through wild interest rate swings and re-educating clients

10:22 - Building a business from scratch in a brand new city

15:02 - Current team size and structure at Aspire Realty

17:19 - Where her best clients come from and staying visible locally

19:18 - Why she pours equal resources into a $50,000 condo and a $5 million listing

23:59 - Why she shrank her team instead of scaling it

27:04 - Her two-minute lead follow-up philosophy without being pushy

36:03 - Her honest take on AI, its limits, and how she actually uses it

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Guest Bio: Adam Olsen is a Texas real estate broker and team leader who got his license at 18 and closed his first sale within seven months. Over 13 years he built a residential team and a commercial brokerage, the Commercial Professionals, running roughly 350 active residential listings and 130 commercial listings with a staff of about 18 and up to 50 agents.

Episode Summary: Adam Olsen joins Tim Donovan to break down how he grew a real estate business from a single 18-year-old agent into a 40 to 50 agent operation spanning residential and commercial sides. He shares the exact social media stunts that built his following, his lead follow up scripts, and why he refuses to obsess over ROI in an industry where deals can close years after the first inquiry.

What's Covered:

• Adam explains his origin story, getting licensed at 18 after his mother suggested real estate, and closing his first house within seven months before scaling into a Zillow-partnered team.
• He details the current team structure, including a listing coordinator, transaction coordinator, sales manager, full time photographer, marketing assistants, office managers, a builder rep, and around 40 to 50 agents across residential and commercial companies.
• Adam breaks down the social media strategy that changed his trajectory, including community focused business interview videos, sponsoring a local university, bringing in RE-MAX skydivers and a hot air balloon, and giving away Houston Astros World Series tickets that gained 30,000 followers and reached 3.5 million people in three days.
• He walks through his lead follow up process step by step, calling within five minutes, asking about cash versus financing after securing an appointment, and running call, text, email sequences for the first three days before moving to a longer cadence.
• Adam discusses why he believes real estate is nearly impossible to properly measure for ROI since leads can convert months or years later, and why he instead focuses on the simple metric of spend versus revenue on any given lead source.
• He shares his magic wand answer about wanting agents and staff to fully buy into the big picture, plus his concrete advice for agents wanting to level up: hit 50 calls a day and send daily searches, since phone time and searches are what actually generate showings and closings.

Timestamps:

00:00:38 - Adam's origin story and getting licensed at 18

02:34 - What the team looks like today, roughly 18 staff and 40 to 50 agents

06:00 - The social media turning point that changed his trajectory

08:37 - Giving away Houston Astros World Series tickets for massive reach

12:25 - Other lead generation channels: Zillow, open houses, 24/7 answering service

14:34 - Going heavy into AI and buying a supercomputer for the office

20:16 - Step by step lead follow up process and scripts

23:07 - Why real estate is nearly impossible to properly ROI

28:04 - The magic wand question about fixing the business

31:18 - One specific action agents should start this week: 50 calls a day

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Guest Bio: Kris Caldwell leads the Apollo Group at eXp Realty across the Denver and Chicago markets, with his Colorado team on pace to help over a thousand families and cross roughly $600 million in volume this year. He got his start in private banking and corporate fitness management before pivoting into real estate in 2015, eventually building a repeat-and-referral driven team through disciplined coaching and relationship-first systems.

Episode Summary: Kris Caldwell shares the winding path that took him from JPMorgan Chase and 24 Hour Fitness into real estate, and the credit-card gamble that launched his production career. He unpacks how his Denver and Chicago teams generate hundreds of leads a month, why he still spends 10 percent of his time in production, and the identity-driven coaching philosophy that has him aiming for a billion-dollar team.

What's Covered:

• Kris recounts his unconventional path into real estate, moving from private banking in Chicago to a district manager role at 24 Hour Fitness before a friend recruited him into a Colorado real estate brokerage in 2015.
• He credits his marriage as the real turning point in his career, explaining that choosing to build the business together with his wife rather than alone became his core competitive advantage through the hard seasons.
• Kris details his lead generation stack, including Zillow, Google Pay-Per-Click, Ylopo, and an AI tool called Radar AI, which together produce 500 to 700 leads a month for his agents, supplemented by large-scale referral events like a Rockies tailgate, a Navy SEALs charity golf event, and a Denver Zoo Lights night that drew 3,000 past clients.
• He shares the story of taking out a $30,000 credit card to fund $5,000 a month in leads when he first started, treating it as a bet on himself that led to closing 10 contracts his first year without ever being mistaken for a rookie agent.
• Kris explains his follow-up philosophy, describing himself as a 'black hole' that clients can't escape once captured, built on a rule of following up with kindness forever rather than pressure or scarcity.
• He closes with tactical advice for agents wanting to scale, arguing that calendar discipline is the single biggest predictor of production, and that agents must protect personal time just as fiercely as client time to sustain long-term endurance.

Timestamps:

00:00:23 - Introducing Kris Caldwell of eXp's Apollo Group

00:04:50 - The real turning point: choosing his wife every time

00:07:01 - How the business is structured today and his 90/10 time split

00:09:10 - Doubling down on high-touch in an AI-driven industry

00:11:20 - Staying in production and the 'guy in a hole' story

00:11:56 - Team size, $600 million goal, and the billion-dollar vision

00:14:21 - Rebuilding from scratch: the $30,000 credit card bet

00:19:58 - Lead generation stack and referral events explained

00:22:59 - The 'black hole' follow-up philosophy and following up with kindness

00:28:40 - Magic wand answer: getting people to believe in themselves

00:31:14 - Calendar discipline as the key to scaling production

00:35:26 - Where to find Kris and the meaning behind Apollo Group

Guest Bio: Jim Bim is a veteran real estate agent based in Columbia, Maryland, with over 43 years in the business. He runs a lean, family-based operation with his two sons—no large team, no bought leads—closing 225-250 homes per year. Early in his career he was mentored by a top local realtor, a builder, and a developer, and later found his true style after discovering Mike Ferry's aggressive, high-contact approach to prospecting.

Episode Summary: Jim Bim joins Under Contract to explain why he's spent four decades avoiding Zillow leads, teams, and shortcuts in favor of pure, high-volume phone prospecting. He shares how getting comfortable with rejection—fast and often—became the foundation of his entire business philosophy, and why he thinks most agents fail because they refuse to see themselves as salespeople.

What's Covered:

• How Jim got his start 43 years ago through his mother and three mentors who taught him the realtor, builder, and developer sides of the business
• Why switching from Tommy Hopkins' sales style to Mike Ferry's aggressive approach in 1989 was the single biggest turning point in his career
• His blunt advice for brand-new agents starting from zero: get comfortable with rejection by getting as much of it as fast as possible
• Why he and his two sons prospect 12-15 hours a day by phone and refuse to buy leads from platforms like Zillow
• His contrarian take that agents can't build a sustainable business on past clients alone, and why most realtors fail because they don't accept they're in a direct sales business
• His honest reflection on being "stuck" at 200-250 transactions for three years, and why he won't sacrifice profit margin or client service just to scale
• His skepticism about AI replacing realtors, and the danger of clients treating AI-generated advice as gospel

Timestamps:

00:00 - Intro and guest introduction

00:32 - How Jim got into real estate 43 years ago

01:26 - Today's business: family model, 225-250 homes a year

02:01 - Turning points: early mentors and discovering Mike Ferry

04:01 - Starting from scratch: "get comfortable with rejection"

05:36 - Where clients come from: the power of the phone

07:11 - Follow-up philosophy: Zillow leads vs. expireds and FSBOs

09:24 - Outworking the competition and staying ethical

10:21 - Contrarian belief: past clients alone won't sustain a business

12:41 - Time management, discipline, and reverse-engineering income goals

14:17 - The challenge of doubling business after plateauing at 250 transactions

17:04 - Biggest industry pain point: agent skill gaps and transaction friction

18:03 - Jim's honest take on AI in real estate

20:58 - Seven-year industry cycles: what will and won't change

23:15 - Where to find Jim Bim and Go Winning Edge

Guest Bio

Colleen Bechtel leads Advantage Home Team out of Casa Grande, Arizona, a market between Phoenix and Tucson. She got into real estate in 1991 after her mother-in-law, a managing broker before Keller Williams ever existed in Arizona, offered to pay for her real estate schooling. What started as a single-agent business became a team in 2005-2006 after reading The Millionaire Real Estate Agent and watching people organically start asking to join her. When the 2008 recession hit and her market's average sale price collapsed to $68,000, Colleen pivoted hard into bank-owned foreclosures and became a HUD Local Listing Broker, building the systems-driven operation that still runs her business today. Thirty-five years in, she leads a team built on a 16-year-old database, a family business that now includes her son, and a simple standard she credits for most of her success: she answers the phone.

Show Notes

Tim sits down with Colleen Bechtel, a 35-year Casa Grande, Arizona broker who has survived and adapted through more real estate cycles than almost anyone else featured on the show. Colleen's team was born out of necessity during the 2008 recession. Faced with a market where homes were selling for $68,000, she went deep into REO and HUD foreclosure listings, and the operational discipline that market demanded became the systems her team still runs on today.

The most memorable thread in the conversation is Colleen's follow-up philosophy. Her team runs an aggressive "10 days of pain" CRM sequence, but the tactic that stands out is what she does when a lead goes cold after 5 or 6 unanswered attempts: instead of giving up, she sends one more message, not a pitch, but a genuine "hey, I'm getting worried, are you okay?" It works because it gives the lead a graceful way back into the conversation instead of the awkwardness of admitting they've been avoiding her calls. Colleen also shares the sales philosophy she learned from her brother, a small business owner who told her he doesn't take a salesperson seriously until they've called him 3, 4, or 5 times, because that persistence is proof they actually believe in what they're selling.

The conversation closes on AI, where Colleen and her business partner split responsibilities: she handles the marketing and AI-search visibility side (she's already fielding calls from people who found her by asking ChatGPT who the best realtor in Casa Grande is), while her partner owns the deeper systems integration. Colleen's take on the future of the industry is direct: more consolidation, a shrinking agent population, and teams that win by removing geographic constraints, but the trust-based, human guide role of a real estate agent isn't going anywhere.

In this episode:

• Getting into real estate in 1991 after her mother-in-law's offer to pay for school
• Building her first team organically in 2005-2006 after reading The Millionaire Real Estate Agent
• Surviving the 2008 recession by pivoting hard into REO and HUD foreclosure listings
• The $68,000 average sale price that defined her market in 2010
• Why that recession forced her team to build the systems they still use today
• Colleen's blueprint for starting over in a new city: open houses, 5-6 days a week
• The "10 days of pain" CRM follow-up sequence her team runs on every new lead
• The "are you okay?" tactic for re-engaging leads after 5-6 unanswered attempts
• Her brother's sales philosophy: he doesn't take a caller seriously until attempt 3, 4, or 5
• Running a 16-year-old database where sphere of influence and past clients are still the #1 and #2 lead sources
• The boundaries she still holds today: no calls before 8am, after 9pm, or before noon on Sundays
• Why she believes geography is the biggest constraint on team growth, and what she'd change
• Fielding calls from people who found her through ChatGPT search results
• The "your grandma" reframe: why an agent's job shifted from finding houses to navigating the process
• Her prediction: more brokerage consolidation, a shrinking agent population, and teams dominating the next 5 years