PODCAST · business
Under Contract
by Tim Donovan
Under Contract is a show for real estate agents and team leaders who want to build a real business, not just chase the next transaction. Host Tim Donovan sits down with top-producing agents and brokers across the country to break down exactly how they built what they built. Their lead generation systems, follow-up philosophy, pricing models, team structures, and the turning points that changed everything. No fluff, no recycled advice. Just real numbers, real strategies, and the operational details most agents never get to hear straight from the source. Plus an honest look at where AI actually helps a real estate business, and where it doesn't. New episodes drop regularly. Subscribe if you're serious about scaling.
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25
33 Years in Real Estate: Paul Klenk on Leveling Up, AI Leads, and What Never Changes
Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/ Guest Bio: Paul Klenk is a veteran real estate agent based in Olympia, Washington, with over 33 years of experience in the industry. A former Marine Corps officer, he began his real estate career in a small Minnesota town before relocating to Olympia, where he has built a long-running independent practice under his own name, paulklenk.com. Episode Summary: Paul Klenk joins Under Contract to reflect on more than three decades in real estate, tracing the industry's evolution from press-hard triplicate paperwork to AI-driven lead generation. He shares the mindset and strategic moves that leveled up his business, his philosophy on lead follow-up and referrals, and why he believes AI will reshape the mechanics of the job without ever replacing the human relationship at its core. What's Covered: Paul recounts his path into real estate after five years as a Marine Corps officer, starting with 80 transactions in 18 months in a small Minnesota town with no MLS, no team, and no home inspections.He identifies switching brokerages to surround himself with top-producing peers, plus attending a Brian Buffini systems course, as the key turning points that leveled up his business.Paul lays out his advice for an agent starting from zero in a new city: target agents nearing retirement for referral business and consider buying leads to jumpstart a database, while acknowledging buyer agency shifts have made this harder than in his early years.He breaks down his current client sources, noting roughly half his business comes from past clients and about 30 percent now comes organically from AI search referrals, a trend he attributes to decades of consistent Zillow advertising and owning his own domain name.Paul describes his simple, professional follow-up process for new leads, contrasts aggressive versus relational follow-up styles, and explains his approach to warmly handing off overflow leads to trusted junior agents at a fair referral rate.Asked what he would change with a magic wand, he says new agents should be required to act as their own transaction coordinators for their first two years to force them to learn how to manage a deal, and he closes by predicting AI will streamline listing paperwork while human relationships remain the unchanging core of the business. Timestamps: 00:00:22 - Introducing guest Paul Klenk from Olympia, Washington00:00:43 - Paul's path from the Marine Corps into real estate00:01:24 - Early career in a small Minnesota town with no MLS or transaction coordinators00:03:29 - How real estate has constantly changed over 30-plus years00:07:42 - The turning points that leveled up Paul's business00:10:00 - Leveling up by surrounding himself with top producers and taking a Buffini course00:12:22 - Thought experiment: building a business from scratch in a new city00:15:05 - Discussion of an aggressive $60,000 a month lead-buying strategy00:17:54 - Where Paul's best clients come from today, including past clients00:20:07 - The importance of owning his own domain and online presence00:21:11 - Getting roughly 30 percent of business from AI search referrals00:22:02 - Paul's simple lead follow-up process00:24:14 - Warm handoff strategy and referral fee philosophy when too busy00:25:36 - Magic wand answer: making new agents be their own transaction coordinators00:27:22 - Paul's current use of ChatGPT in his listing business00:29:10 - Predictions for AI's role in real estate five years from now00:30:10 - Why the human relationship in real estate will never change00:31:23 - Where to find Paul Klenk and closing remarks
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24
From Selling a $725K House in 15 Minutes to Running Her Own Brokerage: Jessica Matute's Story
Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/ Guest Bio: Jessica Matute is a broker-owner in Staten Island, New York, running JMP Properties across New York and New Jersey with about 30 agents. A 23-year real estate veteran, she built her own brokerage from the ground up eight years ago, sold her very first listing within 15 minutes on day one in the business, and has since expanded into new construction, land sales, and development. Episode Summary: Jessica Matute joins Tim Donovan to share the story of her unlikely start in real estate, her journey from top-producing agent to broker-owner of her own boutique brokerage, and the philosophy that has guided her for over two decades. She dives into lead generation tactics, why consistent follow-up separates top producers from everyone else, and why she insists on brutal honesty with clients even when it costs her a listing. What's Covered: Jessica recounts selling her very first listing, a $725,000 detached house in Staten Island, within 15 minutes of opening the open house doors, and how that early win convinced her real estate was her calling.She explains her transition from top-producing agent to broker-owner eight years ago, growing from 12 agents on day one to roughly 30 agents today without actively recruiting, relying instead on reputation and a boutique, hands-on office culture.Jessica identifies opening her own brokerage and moving into new construction, land sales, and development as the two biggest turning points that changed the trajectory of her business.She shares her advice for agents starting from scratch in a new market: buy leads to get moving quickly, get involved in the community, learn the area, and prioritize in-person trust-building like door knocking and open houses over texting.Jessica emphasizes radical honesty with sellers, including telling clients uncomfortable truths about pricing and needed renovations even when it costs her the listing, because protecting her credibility and reputation matters more than winning every deal in the short term.She discusses her lead follow-up strategy, a hybrid of immediate contact, handwritten thank-you cards, and paced follow-up calls, and explains why she believes consistency in follow-up is the single biggest lever most agents are missing, plus her measured, skeptical take on using AI for listing descriptions. Timestamps: 00:00:50 - Jessica's origin story: taking a real estate class on a whim01:31 - Selling her first listing, a $725K house, in 15 minutes02:37 - Building her own brokerage: from 12 agents to 30 today05:49 - Turning points: going independent and moving into new construction08:01 - Advice for starting over in a new city with no database11:10 - Why the market shift now rewards agents who actually know their business12:09 - On having uncomfortable conversations and never lying to clients14:26 - Losing a listing over honesty about pricing and renovation needs15:24 - Lead generation strategy: buying leads, door knocking, and postcards19:06 - Why consistent follow-up separates top agents from everyone else22:08 - The magic wand question: consistency as the biggest business fix24:18 - Jessica's take on using AI for listing descriptions25:20 - Predictions for the industry five years from now
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From Maxed Credit Cards to 650 Deals a Year: Patrick Allison's eXp Growth Blueprint
Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/ Guest Bio: Patrick Allison is a team leader at eXp Realty based in Reno, Nevada, who transitioned from a fifth-generation career in the car industry into real estate in 2014. He built his group from a 15-person team into a 75-agent operation spanning five states, with the team on track for roughly 650 transactions and over 350 million dollars in volume this year. Episode Summary: Patrick Allison shares how he scaled his real estate team from 15 to 75 agents across five states by leaning on brokerage collaboration, disciplined follow-up, and a sales-first mindset. He breaks down his philosophy on client acquisition costs, database building, and why he believes AI will never replace the human salesperson in real estate. What's Covered: Patrick explains his path from a fifth-generation car sales background into real estate in 2014, eventually building a 75-agent team across five states doing roughly 650 transactions and over 350 million dollars in volumeHe credits collaboration with other team leads within his eXp network as the single biggest turning point that helped him escape what he calls the messy middle of team growth between 20 and 50 agentsPatrick lays out his advice for agents starting from scratch, arguing that joining a team to reduce upfront financial risk on client acquisition often beats going it alone and going broke on leadsHe discusses his Zillow lead-driven business model, his five pillars of client conversion, and why simply asking for the sale and picking up the phone separates top producers from the 74 percent of agents who close zero transactions in a yearPatrick argues that shows like Million Dollar Listing mislead new agents into underestimating the business fundamentals required to succeed, and that real estate needs to be treated as a career, not a side hustleHe shares his view on AI in real estate, insisting automation can handle logistics like showing requests and drafted texts but will never replace the human ability to sell, and predicts the industry will consolidate into elite solo producers and larger teams Timestamps: 00:00:33 - Patrick's journey from the car industry to real estate in 201400:01:13 - Scaling from a 15-person team to 75 agents in five states00:02:22 - The turning point: collaboration and escaping the messy middle00:04:14 - Advice for agents starting over with no database or reputation00:06:15 - Why client acquisition and follow-up matter more than lead volume00:10:40 - Contrarian take: Million Dollar Listing and the myth of overnight talent00:14:06 - Interest rates, affordability, and the ego problem between agents and lenders00:15:49 - The real challenge: most agents simply do not follow up00:17:08 - AI in real estate and why sales will never be automated00:18:36 - Predictions for the industry five years from now
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Dan DeCapua: The 100-Person Database Strategy That Built a $40M Team
Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/ Guest Bio: Dan DeCapua leads Spotlight Homes, a roughly 10-agent team based in Ann Arbor, Michigan, doing $40-50 million in annual sales. Before real estate, he worked as a stand-up comedian on cruise lines and a tennis pro, and he now teaches new agents his database-building system alongside running his team. Episode Summary: Dan DeCapua shares how a disciplined, deeply personal approach to database building took him from selling $17,500 foreclosures in 2010 to a $40-50 million team business today. He breaks down his exact weekly follow-up cadence, his philosophy on team leadership versus mega-teams, and where he sees AI and human relationships fitting into real estate's future. What's Covered: Dan explains his core strategy of keeping a curated list of just 100 real relationships rather than a bloated database, and using low-cost personal touches like contractor magnets, pet stickers, and personalized keepsakes to build know-like-trust.He details how a new agent in a new city with no sphere should start by getting involved in communities like sports leagues and working renters as a fast, low-barrier way to generate quick paychecks and future referrals.Dan lays out his team's day-by-day operating rhythm, including seller updates on Mondays, new listing hot sheet reviews on Wednesday and Thursday, and dedicating Wednesdays specifically to batch-filming social media content.He argues that many agents waste time chasing outdated tech or over-polished content instead of focusing on consistent human connection and database growth, calling this the trap of looking for an easy button.Dan describes using ChatGPT to prep for a luxury listing appointment, get personality-based coaching on how he communicates, brainstorm client gifts, and soften his own messaging tendencies.Looking ahead, he predicts that despite AI and portals like Zillow, agents who capture and nurture real relationships will always control the business, since buying a home remains a deeply human, trust-based decision. Timestamps: 00:00 - Intro and welcoming Dan DeCapua00:56 - Dan's path from comedy and tennis into real estate02:09 - Starting out during the foreclosure crisis02:52 - Dan's current numbers and team production04:17 - The key turning point: mastering the 100-person database07:53 - How Dan would rebuild his business from scratch in a new city10:01 - Team client acquisition strategy and lead sources12:30 - Fixing weak follow-up with a day-by-day system14:55 - Mapping out a high performer's full week16:33 - Biggest mistake agents make: chasing outdated tech19:02 - What it would take to double the business through recruiting20:19 - Magic wand: fixing recruiting and inspection headaches22:38 - Real-world example of using AI to fix a listing appointment25:53 - What will and won't change in real estate in five years28:23 - Where to find Dan and his team
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21
From Zero Sales to 14-Agent Team: Christina Esala's Real Estate Journey
Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/ Guest Bio: Christina Esala is a real estate team leader in Tucson, Arizona, who has been in the business for 18 years after starting a family real estate venture with her father, a minister who did short sales as a side gig. She now leads a growing team of 14 agents, built her sphere largely through Zillow leads, and is launching a local TV show called Tucson at Home. Episode Summary: Christina Esala shares how she went from zero sales in her first year to building a 14-agent team in Tucson, Arizona, discussing her evolving approach to lead generation, follow-up systems, and team growth. She opens up candidly about her love-hate relationship with Zillow, her cautious embrace of AI tools like ChatGPT, and a bizarre ongoing encounter with a likely AI-powered scam text conversation. What's Covered: Christina explains how she got into real estate through her father, a minister who was overwhelmed doing short sales as a side business, and how she failed to sell a single home in her first year before finding mentors who taught her to buy at auction and flip properties.She describes the current structure of her team, now 14 agents after her father stepped down at 79, and her philosophy of distributing new leads to her team while personally handling her own sphere of past clients.Christina discusses her long, expensive relationship with Zillow as a lead source, comparing it to a monster and the Walmart of real estate, while acknowledging it built her client sphere and emphasizing that consistent follow-up is what actually converts and retains those leads over time.She walks through her CRM strategy, using Follow Up Boss and Lofty side by side, and explains the difference between old school spreadsheet-style tracking and newer AI-driven systems that nurture leads automatically.She shares a strange real-world story about an ongoing text conversation with what she believes is an AI scam bot posing as a home seller, including inconsistent details about a death in the family and suspicious late-night texting patterns, and warns agents to be cautious about phishing attempts targeting realtors.When asked what one problem she would solve with a magic wand, Christina says it would be smoothing out the boom and bust cycles that hurt team morale, and her top advice for agents wanting to grow is to tell everyone they meet that they are a realtor, answer the phone, prioritize in-person connection, and hire an assistant once busy. Timestamps: 00:00:46 - How Christina got into real estate through her father00:01:35 - Zero sales in her first year and turning it around00:02:34 - Team structure today and her father stepping down at 7900:05:41 - Marketing and lead generation through Zillow00:08:53 - Follow-up philosophy and CRM systems (Follow Up Boss vs Lofty)00:12:37 - Her late start with ChatGPT and relationship with AI00:13:50 - Strange ongoing text conversation with a suspected AI scam00:17:40 - Magic wand question: solving team morale during market lulls00:21:45 - Top advice for agents wanting to grow their business00:26:19 - Christina's upcoming TV show, Tucson at Home
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Fired Her Whole Team at 41 Weeks Pregnant: Megan Walters on Building Small and Mighty
Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/Guest Bio: Megan Walters is a real estate agent and team leader in Columbia, Missouri, running the House Walters team with eXp Realty. In nine years she has built a small, listing-heavy team on track to close roughly $50 million and 150 units this year, and she also runs the Seven Figure Real Estate Academy teaching agents her lead generation and follow-up systems.Episode Summary: Megan Walters joins Under Contract to share how she went from managing college bars in Columbia, Missouri to running a lean, highly profitable real estate team. She walks through her scrappy no-money lead generation tactics as a new agent, why she intentionally downsized her team while 41 weeks pregnant, and how consistency in social media and personalized follow-up now drive nearly all of her business. She closes with candid thoughts on profitability over volume and how she uses different AI tools across her business.What's Covered:Megan explains her accidental entry into real estate after failing the loan officer exam three times by one point and getting recruited by a local broker while managing two college barsShe details firing her entire team at 41 weeks pregnant and rebuilding a small and mighty team with one agent, now prioritizing character and professionalism over raw productionMegan breaks down her original no-budget lead generation strategy of hand delivering personalized FSBO and expired listing packets instead of cold calling, plus posting on social media daily for over eight yearsShe describes her current follow-up philosophy built around Realvolve CRM workflows, personalized texts, and frequent voice memos so past clients and leads can hear tone and authenticityMegan shares that it took about two years of consistent social media posting before her sphere and local market began trusting her enough to actually hire herShe discusses her advice for agents wanting to grow, emphasizing profit and loss statements and prioritizing profitability over sales volume, and outlines how she uses Claude, ChatGPT, and Gemini for course building, hyper local listing video scripts, and SEOTimestamps:00:00:23 - Introducing guest Megan Walters from Columbia, Missouri00:03:04 - Why Megan keeps her team small and mighty00:05:29 - Turning point of firing her team at 41 weeks pregnant00:05:48 - How COVID reshaped her business mindset00:07:26 - Rebuilding in a new market with FSBO and expired listing packets00:11:02 - Shout out to her Seven Figure Real Estate Academy course00:12:19 - Current lead sources including Google Ads and social media00:17:34 - Follow-up philosophy using Realvolve CRM and personalized outreach00:19:46 - Why she relies heavily on voice memos with clients00:21:20 - Magic wand answer about CRM adoption on her team00:23:53 - Advice on tracking profit and loss over pure sales volume00:26:04 - How she uses Claude, ChatGPT, and Gemini in her business
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Green Bay Greg on the Grenade Rule, 51% Past-Client Sales, and Why He Still Cold Calls at 42
Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/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 agentsHe 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 fatherGreg 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 teamHe 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 healthGreg 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 conversionHe 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 databaseTimestamps:00:00:47 - Greg's origin story getting licensed in 2006 and playing online poker before taking real estate seriously00:03:10 - Team structure breakdown, 14 agents, 3 staff, and refusing to be a body count business00:05:20 - The Seth Godin tribe philosophy and hosting a five figure vineyard event for 500 people00:08:30 - A day in Greg's life including accountability meetings with Tandan and staying hands on with systems00:12:37 - Time management honesty, working on heaters, and the grenade rule for accountability00:15:53 - Boomtown history, becoming a peer coach, and diversified current lead sources00:20:19 - Quitting social media with the Brick device and discussing mental health in real estate00:21:51 - Follow up philosophy, avoiding aggressive pounding, and using behavioral retargeting data00:26:17 - Why accountability and clearly defined next steps drive conversion, citing the 5.6 percent stat00:30:14 - The magic wand answer, wanting a steady flow of high quality seller leads and yearly market reviews00:32:16 - Tactical advice for agents wanting to grow, get organized with a CRM and mine your contacts
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Herman Antonov: Why He'd Rather Book 3 Appointments Than Chase 100 Leads
Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/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 Antonov00:30 - How Herman got into real estate through Craigslist and blogging02:38 - Team size and annual transaction volume today04:58 - Instagram lead generation strategy overview05:29 - Ukrainian-language video hits 130,000 views08:08 - Down payment assistance ad targeting first-generation buyers09:17 - Follow-up philosophy and drip email strategy11:08 - Building a business from scratch in a new city14:06 - Tactical advice: get a showing partner and specialize17:00 - Magic wand problem: fixing appointment setting20:06 - Using ChatGPT and ElevenLabs for AI video walkthroughs23:18 - Predictions for the industry five years out26:20 - Where to follow Herman and his team
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Why This Top Agent Threw Away His Business Cards (And Other Counterintuitive Moves)
Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/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 licenseHe 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 transactCasey 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 resultsHe 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 knocksCasey 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 botheredHe 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 knowledgeTimestamps:00:00:39 - How Casey got into real estate after running out of college money00:03:37 - The roof repair that never happened and led to foreclosure00:06:03 - Getting licensed with his last $50000:08:06 - Mentor Mike McCarthy and the turning point conversation00:10:50 - Why are you stealing someone else's joy, the hiring lesson00:12:46 - What Casey would do first starting over in a new city00:17:09 - Why Casey stopped using business cards00:19:08 - Zillow partnership and referral conversion rates00:22:14 - Casey's follow-up philosophy and building relationships over transactions00:26:51 - The one problem Casey would fix with a magic wand: follow-up00:31:53 - Casey's early AI platform build in 2014 versus rebuilding it in a weekend with Claude00:36:03 - Using AI-powered seller updates to guide price reduction conversations00:38:04 - Casey's vision for a personal AI assistant trained on his own client conversations
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Why This North Dakota Broker Refuses to Chase Growth (And Sells $50K Condos Like Mansions)
Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/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 houseShe 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 dropKatherine 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 leadsShe 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 businessKatherine 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 sakeShe 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 centralTimestamps:00:53 - How Katherine accidentally got into real estate05:03 - Living through wild interest rate swings and re-educating clients10:22 - Building a business from scratch in a brand new city15:02 - Current team size and structure at Aspire Realty17:19 - Where her best clients come from and staying visible locally19:18 - Why she pours equal resources into a $50,000 condo and a $5 million listing23:59 - Why she shrank her team instead of scaling it27:04 - Her two-minute lead follow-up philosophy without being pushy36:03 - Her honest take on AI, its limits, and how she actually uses it
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15
Adam Olsen: Licensed at 18, Built a 40-Agent Team by Betting Big on Facebook
Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/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 1802:34 - What the team looks like today, roughly 18 staff and 40 to 50 agents06:00 - The social media turning point that changed his trajectory08:37 - Giving away Houston Astros World Series tickets for massive reach12:25 - Other lead generation channels: Zillow, open houses, 24/7 answering service14:34 - Going heavy into AI and buying a supercomputer for the office20:16 - Step by step lead follow up process and scripts23:07 - Why real estate is nearly impossible to properly ROI28:04 - The magic wand question about fixing the business31:18 - One specific action agents should start this week: 50 calls a day
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Why This eXp Team Leader Bet $30,000 on a Credit Card to Break Into Real Estate
Want the the best insights from this episode and more in bite-sized nuggets? Signup for our free newsletter at undercontractnotes.comGuest 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 Group00:04:50 - The real turning point: choosing his wife every time00:07:01 - How the business is structured today and his 90/10 time split00:09:10 - Doubling down on high-touch in an AI-driven industry00:11:20 - Staying in production and the 'guy in a hole' story00:11:56 - Team size, $600 million goal, and the billion-dollar vision00:14:21 - Rebuilding from scratch: the $30,000 credit card bet00:19:58 - Lead generation stack and referral events explained00:22:59 - The 'black hole' follow-up philosophy and following up with kindness00:28:40 - Magic wand answer: getting people to believe in themselves00:31:14 - Calendar discipline as the key to scaling production00:35:26 - Where to find Kris and the meaning behind Apollo Group
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13
"Get Comfortable With Rejection": How Jim Bim Sells 250 Homes a Year Without a Team or a Single Bought Lead
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 businessWhy switching from Tommy Hopkins' sales style to Mike Ferry's aggressive approach in 1989 was the single biggest turning point in his careerHis blunt advice for brand-new agents starting from zero: get comfortable with rejection by getting as much of it as fast as possibleWhy he and his two sons prospect 12-15 hours a day by phone and refuse to buy leads from platforms like ZillowHis 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 businessHis 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 scaleHis skepticism about AI replacing realtors, and the danger of clients treating AI-generated advice as gospelTimestamps:00:00 - Intro and guest introduction00:32 - How Jim got into real estate 43 years ago01:26 - Today's business: family model, 225-250 homes a year02:01 - Turning points: early mentors and discovering Mike Ferry04:01 - Starting from scratch: "get comfortable with rejection"05:36 - Where clients come from: the power of the phone07:11 - Follow-up philosophy: Zillow leads vs. expireds and FSBOs09:24 - Outworking the competition and staying ethical10:21 - Contrarian belief: past clients alone won't sustain a business12:41 - Time management, discipline, and reverse-engineering income goals14:17 - The challenge of doubling business after plateauing at 250 transactions17:04 - Biggest industry pain point: agent skill gaps and transaction friction18:03 - Jim's honest take on AI in real estate20:58 - Seven-year industry cycles: what will and won't change23:15 - Where to find Jim Bim and Go Winning Edge
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12
$68,000 Homes and a 16-Year-Old Database: Colleen Bechtel on Surviving Every Cycle in Real Estate
Guest BioColleen 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 NotesTim 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 schoolBuilding her first team organically in 2005-2006 after reading The Millionaire Real Estate AgentSurviving the 2008 recession by pivoting hard into REO and HUD foreclosure listingsThe $68,000 average sale price that defined her market in 2010Why that recession forced her team to build the systems they still use todayColleen's blueprint for starting over in a new city: open houses, 5-6 days a weekThe "10 days of pain" CRM follow-up sequence her team runs on every new leadThe "are you okay?" tactic for re-engaging leads after 5-6 unanswered attemptsHer brother's sales philosophy: he doesn't take a caller seriously until attempt 3, 4, or 5Running a 16-year-old database where sphere of influence and past clients are still the #1 and #2 lead sourcesThe boundaries she still holds today: no calls before 8am, after 9pm, or before noon on SundaysWhy she believes geography is the biggest constraint on team growth, and what she'd changeFielding calls from people who found her through ChatGPT search resultsThe "your grandma" reframe: why an agent's job shifted from finding houses to navigating the processHer prediction: more brokerage consolidation, a shrinking agent population, and teams dominating the next 5 years
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11
700 Transactions Wasn't Enough: Why Rene Bartum Walked Away and Rebuilt With 5 Agents
Guest BioRene Bartum leads Next Steps Group, an eXp mega team based in Ocala, Florida. Before real estate, he worked as a teaching golf pro in Fort Myers, moved into B2B office equipment sales in Orlando, and eventually founded a marketing agency called Connectar, working with celebrity makeup artists. After starting a family and deciding he wanted his time back, he talked his way into a job at a local real estate school, working up from marketing director to GM before finally getting licensed in Q4 2022. He built his first team to over 700 transactions and 70+ agents, then walked away from it in January 2026 over a culture problem he says he failed to catch soon enough. Eight months later, Next Steps Group has scaled back to 30+ agents across 32 zip codes, with Rene positioning the team as one of the few Zillow Preferred Partners in Central Florida.Show NotesTim sits down with Rene Bartum, an Ocala, Florida team leader whose path into real estate ran through a golf course, a B2B sales floor, and a marketing agency built around celebrity makeup artists before he ever got licensed. Rene's rise since Q4 2022 has been fast by any measure, but the most interesting part of his story isn't the growth, it's the moment he walked away from it. After building a team to 700+ transactions and 70+ agents, Rene says he failed to notice that culture, morals, and values matter more than volume. In January 2026, he left that brokerage and restarted Next Steps Group with just 5 agents. Eight months later, the team has scaled back past 30 agents.The conversation goes deep on the AI infrastructure Rene has built to support that growth: a custom-built platform called ALM Trainer that role-plays new agents against 60 different AI personas before they ever talk to a real lead, an AI nurture system that runs a strict 7-30-30 follow-up rule against a 50,000-lead database, and an AI contract writer currently in development to catch compliance mistakes before they cost a new agent their EMD. Rene is candid about why Zillow remains his highest-converting, highest-credibility lead source, and closes with a philosophy that runs through the whole conversation: it's not what you can do, it's what you will do.In this episode:From teaching golf, to B2B sales, to a celebrity-makeup-artist marketing agency, to real estateWorking his way from marketing director to GM at a real estate school before getting licensedBuilding a team to 700+ transactions and 70+ agents, then walking away over a culture failureRestarting Next Steps Group in January 2026 with 5 agents, scaling past 30 in 8 monthsALM Trainer: the custom AI role-play software Rene built to onboard agents fasterWhy Zillow remains his highest-intent, highest-converting lead sourceThe AI nurture system running a strict 7-30-30 rule against a 50,000-lead databaseThe 5-minute response standard, and what happens when an agent misses itBuilding an AI contract writer to protect new agents from costly compliance mistakes"Is it harder to make the call, or harder to tell your wife you can't pay the mortgage?"Why Rene doesn't want to sell real estate for the rest of his life, and what he's building insteadHis prediction: title and mortgage get streamlined, but the human connection in real estate never goes away
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10
My Biggest Lead Source Is AI: Darren Tackett on Winning the Search Game Before Everyone Else Catches Up
Guest BioDarren Tackett leads the Tackett Team at eXp Realty in Scottsdale, Arizona, after 30 years in the business. He started in real estate almost by accident — a pre-med track that didn't pan out, six months selling cars, and a college roommate's decision to get licensed that nudged him to do the same. Four years into a coaching program called The Core taught him the financial discipline he was missing (including recovering from an IRS tax lien), and set him on the path to eXp. When his original business partner and team leader passed away unexpectedly during COVID, Darren inherited leadership of the team overnight — and has since grown it from roughly 11 to nearly 35 agents, scaling from about $100M in production in his first year at eXp to a projected $250-280M this year.Show NotesTim sits down with Darren Tackett, a 30-year Scottsdale real estate veteran who built one of eXp's top-performing teams after being thrust into leadership following his business partner's sudden death during COVID. Darren is refreshingly candid about how much of his growth has come from simply refusing to operate in isolation — networking aggressively with other top-producing teams under a philosophy he calls "rip off and duplicate": if something's working for someone else, ask them how they did it, and use it.The conversation covers Darren's deliberately loose management style — he doesn't hold agents accountable day-to-day, instead helping each one find the lead-gen channel that actually fits their personality, whether that's open houses, cold calling, or pure digital. On lead generation, Darren makes a sharp distinction: his team skips Zillow Flex entirely (he compares Flex teams to industrial tuna boats scooping up a shrinking supply of buyer leads) in favor of alliances with nearly every other seller-lead company on the market. But the most striking thread is AI — Darren says his single biggest personal lead source right now is people finding him through ChatGPT and Grok searches for "top North Scottsdale Realtor," and he's spent the last six months investing heavily in AEO (answer engine optimization) to defend that position before it becomes common knowledge. He's also used AI internally to duplicate roughly 80% of his team's software stack, cutting overhead and app fatigue for his agents. The episode closes with Darren's blunt prediction: the agent population needs to shrink, and it will — but the agents who remain will be more professional, not fewer in value.In this episode:From a failed pre-med track and six months selling cars to 30 years in real estateThe coaching program (The Core) that fixed his financial discipline — including recovering from an IRS tax lienInheriting team leadership overnight after his partner's sudden death during COVIDThe "rip off and duplicate" philosophy behind scaling to nearly 35 agents in 3.5 yearsWhy Darren gives agents total autonomy to find their own lead-gen laneWhy his team skips Zillow Flex entirely — the "tuna fishing boat" comparisonHis #1 personal lead source right now: people finding him through AI searchInvesting in AEO before it becomes common knowledge among competitorsUsing AI to duplicate 80% of his team's software stack and cut overheadHis follow-up system: FollowUp Boss automations plus a "7-8 days of pain" call cadenceWhy Darren still has agents do their own follow-up instead of outsourcing to an ISAThe one thing Darren wishes AI could take off his plate: monitoring lead conversionWhat would need to be true to double the business — and the recruiting lesson that took years to acceptWhy Darren still tells agents to start with cold calling expireds and canceled listingsHis prediction: fewer agents in 5 years, but a higher bar of professionalism
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9
Flexibility Comes at a Cost: Jase Leonard's Time-Blocking Blueprint for 228 Deals a Year
Guest BioJase Leonard leads HousingAroundAZ, a real estate team based in Chandler, Arizona, in the Phoenix metro market. Before real estate, he built and directed a corporate call center — and walked away from the job rather than lay off half his staff. His first six months in real estate produced exactly one transaction, and his wife gave him one final shot to make it work. Eleven years later, Jase runs a 14-agent team that closed 228 transactions last year, built on a foundation of expired and canceled listings, pre-foreclosure and probate outreach, and one of only 23 Zillow Flex partnerships in the Phoenix metro area.Show NotesTim sits down with Jase Leonard, an 11-year real estate veteran and team leader in Chandler, Arizona, who came into the business with a strong sales background from running corporate call centers — and still nearly quit in his first six months. Jase is candid about what it actually took to turn things around: watching and emulating agents who were already succeeding (specifically Joshua Smith), leaning hard into the one lead source that fit his strengths (expired and canceled listings), and slowly building the discipline his wife's ultimatum forced him toward.The conversation is packed with tactical detail: Jase's "stool of the chair" philosophy on lead generation (3-4 sources, never fewer, never chasing more than you can master), his team's "War Report" system that scores every agent's weekly money-making activities, and his exact follow-up philosophy — including the specific, permission-based language he uses to justify calling a lead six times without it feeling pushy. He also gets into how his team diversified beyond expireds into pre-foreclosure and probate outreach as DNC regulations made cold-calling harder, and how Zillow's lead-referral partnership became an unexpected lifeline during COVID.On AI, Jase describes something few other guests have mentioned: building a custom Claude skill that generates an AI-created CMA specifically to preempt tech-savvy sellers who've already run their own numbers through Gemini or ChatGPT before the listing appointment even starts. The episode closes with his take on what can't be taught — strive — and his prediction that agents will increasingly resemble lawyers: less about search, more about advice, negotiation, and guiding people through a process AI still can't fully see behind the curtain of.In this episode:From building corporate call centers to walking away rather than laying off staffOne transaction in his first six months — and his wife's "one more chance" ultimatumLearning the business by emulating agents like Joshua Smith on podcasts and YouTubeBuilding a career on expired and canceled listings — and why it still worksThe "stool of the chair": why you need 3-4 lead sources, never fewer, rarely moreHow DNC regulations pushed his team toward pre-foreclosure and probate outreachBecoming one of only 23 Zillow Flex teams in the Phoenix metro areaThe War Report: scoring every agent's weekly money-making activitiesTime-blocking as the antidote to "flexibility comes at a cost"Jase's follow-up philosophy: 14-15 touches, task-based, and the permission to "blow them up"Why he built a custom AI-powered CMA to preempt sellers who've already Googled their priceThe one thing Jase says he can't teach: striveWhy he believes agents will start to resemble lawyers — advisors, not searchers
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8
Don't Hire Another You: Roxanne Humes on Building a Team Like a Band
Guest BioRoxanne Humes is a real estate agent and team leader with Coldwell Banker in the Pittsburgh area. Before real estate, she spent years as a buyer for May Company (Filene's in Boston, then Kaufmann's in Pittsburgh), and later helped grow a wholesale apparel company to $40M in revenue — until the 2009 financial crisis, tied to the owner's real estate investments, ended that chapter. At 42, with her husband's blessing and her father-in-law's nudge, she got her real estate license and started over from zero, with no local network and no built-in client base. Fifteen years later, she leads a team of roughly 12 agents alongside her business partner Chris Ellison and regional VP John Perry, pacing to close in on 200 team sales this year while personally handling 50-60 units of her own.Show NotesTim sits down with Roxanne Humes, a Pittsburgh-area Coldwell Banker agent whose path into real estate started with a layoff, a career in fashion buying and wholesale apparel, and a blunt question to her husband: what do we do now? She got her real estate license at 42, was written off by nearly every broker she interviewed with for having no local friends-and-family network, and built her business anyway — first through relentless open houses and professional photography (a rarity in her market at the time), and eventually into a team built on a philosophy she compares to a band: nobody needs to be the lead singer, everyone just needs to want to make good music together.Roxanne walks through her three-question hiring filter (are you nice, are you actually nice, and are you interested in growth), why she brought on a business partner instead of "hiring another her," and where she believes most agents leak business — not from lack of leads, but from failing to categorize and follow up with leads by urgency. She's candid about not being the most tech-forward person on her team, but she's become genuinely dependent on AI for listing descriptions and reverse-prospecting the MLS, cutting tasks that used to take over an hour down to minutes. The conversation closes with a sharp insight from her partner Chris on why buyer-side commission is headed toward full decoupling — and Roxanne's take on why the 2020 industry lawsuit was actually the best thing to happen to the profession.In this episode:Roxanne's path from fashion buyer to a $40M wholesale apparel business — to starting over at 42Getting written off by brokers for having zero friends-and-family networkThe early differentiator: professional photography when no one else in her market was doing itHer three-question hiring filter: are you nice, are you actually nice, and are you growth-mindedThe band analogy: why she doesn't need agents who want to be the lead singerWhy "don't hire another you" was the advice that shaped her partnership with Chris EllisonRoxanne's A/B/C lead framework — and why most leaked opportunities are a follow-up problem, not a lead problem"We think about them 24/7. They think about us once — when they want to buy or sell."How AI cut her listing description process from 90 minutes to a fewReverse-prospecting the MLS: a 15-minute task now down to 1 minuteWhy her partner Chris believes buyer-side commission is headed toward full decouplingWhy Roxanne thinks the 2020 industry lawsuit was the best thing that happened to real estateReinventing herself at 42 — and finding work that finally felt meaningful
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7
We're Not Saving People in the ER: How Richard Berman Sells 150 Homes a Year Without Losing His Evenings
Guest BioRichard Berman is a real estate agent with RenoSparksHomes.com in Reno, Nevada. He got into real estate eight years ago after a mentor showed him his GCI and Richard asked, on the spot, how to get his license — leaving a $140K/year B2B sales job in the process. His first year netted just $14,000 after expenses. Eight years later, he closed 120 transactions last year and is on pace for roughly 150 this year — with a lean team of himself, one buyer's agent, and three full-time assistants, no additional agents under him. He's built his business on a rigid, professional's schedule and a hard rule: after 7pm, the business day is over.Show NotesTim sits down with Richard Berman, a Reno, Nevada agent doing what most agents chase but rarely achieve: 150 transactions a year, run by a team of four, without sacrificing his evenings or his marriage. Richard traces it back to an early lesson from his mentor Alan, who caught him doing handyman-level tasks on a listing and asked him point blank: "Is that how much your time's worth?" From that moment, Richard organized his entire business around a small number of money-making activities — prospecting, lead follow-up, appointments, and negotiation — and delegated everything else, starting with hiring his own wife as his first assistant.The conversation goes deep on Richard's follow-up philosophy (motivation and timeframe decide everything — the 3-3-3 method for hot leads, quarterly touches for everyone else), his original vendor-partnership strategy for building a database from zero, and the FAQ system he built by simply writing down every repeated question he ever got asked. But the most memorable thread is boundaries: Richard runs his business on a fixed schedule, tells clients upfront exactly when he's unavailable, and lives by his mentor's warning — "we're not saving people in the ER." Nothing he does after 7pm moves the needle, so he doesn't do it.In this episode:The "Wolf of Wall Street" moment that got Richard into real estateHis brutal first year: $58K gross, $14K net — and the decision to keep goingThe handyman lesson: "is that how much your time's worth?"The handful of activities that actually generate money — and why everything else should be delegatedWhy Richard hired before he "needed" to, based on self-belief in his business planHis original database-building strategy: cold-calling small local vendors for coffee, not big companiesRichard's follow-up philosophy: motivation and timeframe over "the hot lead"The 3-3-3 method for high-motivation leads, quarterly touches for long-term nurturesWhy Richard tells clients his exact hours upfront — and why almost no one objects"We're not saving people in the ER" — the boundary that protects his marriage and his eveningsThe FAQ system that eliminated dozens of repeat questions before they're even askedWhat would need to be true operationally to double his business in 2 yearsWhere AI genuinely helps (transaction management, more human-sounding follow-up) — and where his own system still falls short
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6
Throw the Party, Own the Market: Chip Hodgkins' One-to-Many Playbook
Guest BioChip Hodgkins is the broker/owner of Hodgkins Homes in Syracuse, New York, leading a 10-agent team with a database of over 123,000 contacts. A serial entrepreneur who built and sold roughly 14 businesses — including scaling a bearings company from $350M to $720M before selling to Emerson Electric — Chip "retired" at 40, only to be pushed into real estate by his wife days later. He closed his first two listings within 48 hours of getting licensed and finished his first year ranked #3 in RE/MAX New York State. 26 years later, he's built a business on leverage: one-to-many webinars, celebrity radio and TV endorsements (including Glenn Beck and Barbara Corcoran), and a relentless personal brand built on showing up everywhere in Syracuse.Show NotesTim sits down with Chip Hodgkins, a serial entrepreneur turned Syracuse real estate powerhouse, for one of the most colorful founder stories the show has featured yet. Chip walks through his path from selling a $350M-to-$720M bearings company to Emerson Electric, "retiring" at 40, and getting pushed into real estate by his wife within days — closing a $700,000 listing in his first 48 hours in a market where the average deal was $160,000.The conversation centers on leverage. Chip breaks down his one-to-many philosophy: running live Thursday-night webinars that turned $350 in Facebook ad spend into 8 real conversations (and multiple five-figure commissions), and his signature move — calling up restaurants before they open and throwing invite-only parties for 120-150 people, covering the bar himself, in exchange for pure word-of-mouth positioning as "the guy who gets you into places before they open." He's also candid about the two moments that each doubled his business: getting endorsed on-air by Glenn Beck, then later by Barbara Corcoran.But Chip is just as clear about the limits of leverage — he doesn't skip one-on-one relationships, citing "never eat alone" as a core philosophy and explaining why his highest-value referrals still come from individual coffee catch-ups, not big events. The conversation closes with Chip's team's follow-up standard (90 seconds, not 10 minutes), where AI genuinely helps (follow-up, not cold outbound), and a cautionary story about accidentally texting someone on New York's Do Not Call list.In this episode:From a $350M-to-$720M bearings company sale to "retiring" at 40 — and getting real estate within daysClosing a $700K listing in his first 48 hours in a $160K-average marketFinishing his first year as the #3 agent in RE/MAX New York StateThe one-to-many webinar system: $350 in ad spend, 45 attendees, 11 appointmentsChip's signature move: throwing invite-only pre-opening parties for local restaurantsWhy two celebrity endorsements (Glenn Beck, then Barbara Corcoran) each doubled his businessWhy "never eat alone" still matters even with a 123,000-person databaseHis team's follow-up standard: 90 seconds, not 10 minutes — and what happens if you miss itWhere AI is genuinely valuable (follow-up) versus where Chip won't touch it (cold outbound)A cautionary tale about AI, Do Not Call lists, and New York State compliance
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5
Med School to $41M: Ali Keys on Delegation, Consistency, and Building a Real Estate Brand
Guest BioAli Keys is the broker/owner of Got Keyed Realty, serving Dearborn and the greater Southeast Michigan area. He was studying to become a doctor when limited finances forced him to step away from medical school — a decision one of his professors warned him he'd regret. Instead, Ali closed three sale-by-owner deals in his first 30 days in real estate and never looked back. Over a decade later, he's trained hundreds of agents and built a business that jumped from $12.5M to $41M in production in a single year after one pivotal hire.Show NotesTim sits down with Ali Keys, broker/owner of Got Keyed Realty in Dearborn, Michigan, for a conversation that starts in medical school and ends with one of the most dramatic growth numbers featured on the show so far. Ali walks through the moment he almost became a doctor instead of a realtor, and the blunt exchange with his professor that still echoes years later — "if you leave now, you're never coming back." He left anyway.The heart of the conversation is delegation. Ali spent years doing everything himself — showings, offers, negotiations — until he hired a director of operations who asked him one question in their first five minutes together: "How can I help you?" That hire took his business from $12.5M to $41M in a single year. From there, Ali breaks down his three-part framework for keeping leads from going cold (consistency, follow-up, and value), the specific, non-generic ways his team follows up with clients, and why he believes AI's real value in real estate is entirely on the back end — never replacing the human relationship at the front.In this episode:Why Ali left medical school despite his professor's warning — and never looked backClosing 3 sale-by-owner deals in his first 30 days in the businessThe delegation moment that took his business from $12.5M to $41M in a yearWhy "how can I help you" was the question that told Ali he'd found the right hireAli's blueprint for starting over in a new city with no database or reputationThe "recycle approach" to lead generation — no paid leads, fully organicAli's 3-part framework for retention: consistency, follow-up, and valueSpecific, real follow-up tactics that don't feel like a sales pitch (the door-knocking example)Why Ali believes "AI won't take your job — people who use AI well will take your job"Where AI actually creates value: the back end, never the client relationshipWhy the human touch in real estate isn't going away, even as consumers get smarter with AI
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4
If You Don't Answer Your Phone, Somebody Else Will: Sondra Hernandez on Responsiveness in Real Estate
Sondra Hernandez is the broker/owner of Cobblestone Realty Partners in Enid, Oklahoma, with 23 years in the business. She spent two decades running an accounting department before a friend nudged her into real estate — a career she says she's never once looked back from. Sondra built a multilingual brokerage (three languages spoken in her office) and a business defined by one non-negotiable standard: she responds to clients in 10 to 15 minutes, every time, from 8am to 8pm.Show NotesTim sits down with Sondra Hernandez, a 23-year real estate veteran and broker/owner out of Enid, Oklahoma, for a conversation about the one thing she believes separates her business from everyone else's: she actually responds. Not eventually — in 10 to 15 minutes, whether it's a call, text, or email, seven days a week. Her take is simple and a little blunt: if you're a realtor and you don't answer your phone, somebody else will.Sondra walks through the turning point that took her from selling $20-30K homes working 15-hour days to a fundamentally different price point — not by working harder, but by advertising differently. She talks candidly about why she deliberately built a multilingual office, why she's not afraid of hard conversations with buyers, sellers, banks, or lenders, and why she ditched every automated lead-nurture program she ever bought in favor of a personal spreadsheet system. The conversation closes with her take on where AI actually helps (branding and advertising) and her conviction that no amount of technology will ever replace the human relationships at the center of real estate.In this episode:The advertising shift that took Sondra from $20-30K homes to $150K+ — without working more hoursWhy "I respond" is Sondra's entire competitive differentiatorHer actual standard: 10-15 minute response time, 8am to 8pm, every dayWhy she built a multilingual brokerage — and the disservice she believes agents do by not offering itWhy she walked away from every paid lead-nurture program she ever boughtHer personal, spreadsheet-based follow-up system — and why she avoids automationSondra's two-part advice for any agent wanting to grow: treat it like a career, and educate yourself constantlyWhere AI actually helps her business (branding and advertising) — and where she won't hand over controlWhat she believes NAR will lose in the next 5-10 years, and why she expects a national MLSWhy she believes the human relationship in real estate can never fully be replaced
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The $300-an-Hour Filter: How Jayson Burtch Built a Southwest Florida Real Estate Empire
Guest BioJayson Burtch leads a top-producing real estate team in Southwest Florida, expanding up the state's west coast into St. Pete, Sarasota, and Naples. He got his start in real estate at 18 after inheriting exposure to real estate investing through his grandfather's rental portfolio, but the real turning point came a decade later — a coaching program in 2012 that took his business from reactive and market-dependent to fully systematized. Since then, Jayson's business has roughly doubled every two to three years, built on a combination of relentless work ethic, diversified lead generation, and — more recently — AI-driven database reactivation.Show NotesTim sits down with Jayson Burtch, a Southwest Florida team leader who's spent over a decade turning raw hustle into a systematized, scaling business. Jayson doesn't sugarcoat what it took — by his own account, his team is regularly working north of 70 hours a week, and his philosophy is blunt: "nobody works harder, I won't be outworked." But underneath the grind is a business built on real systems, starting with a 2012 coaching experience Jayson calls the single most educational year of his career.The conversation covers how Jayson's lead generation philosophy evolved from pure cold-calling to a diversified mix (still 60-65% past clients and sphere of influence, even with heavy paid lead spend), why he holds his team accountable with a hard "5 conversations before new leads get turned on" rule, and how AI is reshaping both his marketing (the shift from SEO to AEO) and his team's ability to reactivate the massive graveyard of old database leads that would otherwise convert with a competitor. Jayson also gets candid about what surprised even him about his own business — the chaos behind the curtain, and just how many hours it actually takes.In this episode:How a $400/month tool called Zillow first changed Jayson's approach to lead gen back in 2012Why "nobody outworks me" is Jayson's actual operating philosophy, not just a taglineThe coaching program Jayson calls the most pivotal moment of his careerJayson's follow-up accountability system: 5 real conversations before agents get new leadsWhy 60-65% of his business is still past clients and sphere of influence, despite heavy paid ad spendThe "$300-an-hour job" filter Jayson uses to evaluate whether he's actually working like it mattersHow AI is helping Jayson's team re-engage old leads that would otherwise convert with someone elseThe shift from SEO to AEO (answer engine optimization) as more buyers start their search with AIWhy Jayson believes the agent population will shrink 65% in the next 5-7 years — but agents themselves aren't going anywhereJayson's advice to his younger self: get properly educated, and don't listen to negativity about coaching
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Social Media Won't Build Your Business... Here's What Actually Does
Guest BioBen Nemec is a real estate agent and team leader in Huntsville, Alabama, running Team Nemec / Huntsville Homes For You. He got his start in real estate after his mother-in-law, a longtime Huntsville agent, brought him on as a partner following an unconventional path through hospitality management, nonprofit sports sponsorships, and a near-miss Coast Guard officer application. Thirteen years later, Ben leads a team built on referral-driven business, disciplined database follow-up, and a firm conviction that relationships — not platforms — are what actually grow a real estate business long-term.Show NotesTim sits down with Ben Nemec, a 13-year real estate veteran and team leader out of Huntsville, Alabama, for a conversation that pushes back hard against one of the industry's most repeated assumptions: that social media is the engine of growth. Ben's take is blunt — it's a facet you have to lean into, but it will not bring you long-term success. What does? The relationships you build, how you treat people, and the job you do for your clients, compounded over years, not months.Ben walks through his own unconventional path into the business, the moment he realized real estate has no overnight success stories, and the specific systems — signed calls, open houses, database touches — that have quietly outperformed paid leads for his team for over a decade. He also opens up about the boundaries he had to learn the hard way to protect his family, and gives a clear-eyed take on where AI actually fits into a relationship-driven business.In this episode:Why Ben believes social media "will not bring you long-term success" — and what he tells his team insteadBen's unconventional path into real estate — hospitality school, the Orange Bowl, and a near-miss Coast Guard officer applicationWhy there's no such thing as overnight success in real estate ("a slow burn, month after month, year after year")Ben's actual lead generation philosophy: sphere of influence, signed calls, and open houses over paid leadsThe #1 way agents leak opportunities they already have (and it's not lead volume)Why Ben credits his CRM (Brivity) for keeping follow-up from falling through the cracksThe moment that changed how Ben protects his time with family — and why he got emotional telling itHow Ben's team uses Claude Cowork — and where he still won't let AI near a client relationshipBen's advice for any agent wanting to grow in the next 12 monthsLooking 5 years ahead: what changes in real estate, and what never will
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Why This Indiana Broker Charges 1% and Still Sells 100+ Homes a Year
Guest BioDrew Wyant is a real estate agent and broker/owner in Columbus, Indiana, running a 1% Lists franchise that now spans nearly the entire state. After leaving a 10-year healthcare career and getting licensed in 2021, Drew built his business from 11 sales in his first year to 130+ in a single year as an individual agent — while also growing a team of 23+ agents managing roughly 100 active listings and 75 pendings at any given time. His full-service, 1% commission model has become his core differentiator in a market of 1.8 million+ competing agents.Show NotesTim sits down with Drew Wyant, a 1% Lists broker/owner out of Columbus, Indiana, who went from cold-calling For Sale By Owners in his first year to running a 23-agent team covering the whole state. Drew breaks down the pivot that changed everything — realizing he was already netting 1% on relocation deals and deciding to just charge that upfront — plus his philosophy on follow-up, referrals as "compound interest," and where AI actually belongs in a real estate business (hint: not between you and the client).In this episode:How Drew went from 11 sales his first year to 130+ in his best yearThe relocation-fee insight that led him to launch a 1% commission modelWhy "good customer service" is not a unique value propositionHis actual follow-up cadence (7-8+ touches before a lead converts)Running a 23-agent brokerage while staying personally active in salesWhere AI helps (compliance, paperwork, transaction coordination) vs. where it hurts (client relationships)The "flywheel" argument for prioritizing deal volume over margin early onOne piece of advice Drew would give himself on day one
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ABOUT THIS SHOW
Under Contract is a show for real estate agents and team leaders who want to build a real business, not just chase the next transaction. Host Tim Donovan sits down with top-producing agents and brokers across the country to break down exactly how they built what they built. Their lead generation systems, follow-up philosophy, pricing models, team structures, and the turning points that changed everything. No fluff, no recycled advice. Just real numbers, real strategies, and the operational details most agents never get to hear straight from the source. Plus an honest look at where AI actually helps a real estate business, and where it doesn't. New episodes drop regularly. Subscribe if you're serious about scaling.
HOSTED BY
Tim Donovan
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