PODCAST · business
Context with Mike DelPrete
by Mike DelPrete
Conversations with industry leaders about the businesses and technologies changing real estate.
Episodes
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Holy Grail 05: The Carpenter’s Cup
On this episode I chat with Luke Babich, CEO of Clever Real Estate, a referral platform that matches buyers and sellers with agents. Clever has grown profitably, partly by integrating brokerage, title, and mortgage -- the Holy Grail is working. Luke's diagnosis of real estate is simple: too many...
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Holy Grail 04: A Day with Rocket
I hit the road and spend a day with Rocket in Detroit. I want to walk the floors and see the biggest company chasing the Holy Grail for myself. I went in skeptical. Redfin's posting a 50% attach rate since the acquisition and I didn't believe it — they were at 27% before. How? Turns out the magic...
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Holy Grail 03: The Power Buyer Clue
I begin by tracking the number of mortgage loan originators at the big players — which tells me who's really investing in the search for the Grail. Then I sit down with Ryan Dibble, one of the Flyhomes co-founders. Flyhomes is a power buyer that stumbled on the Holy Grail with mortgage attach…
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Holy Grail 02: Surveying the Landscape
My first stop: a conversation with Carey Armstrong, who has glimpsed the Grail! She's been at Zillow, built a mortgage company, and is one of the few people I know who's seen this from every angle. I needed someone I trust to help me map the whole landscape before I start digging into the...
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Holy Grail 01: The Search Begins
I'm starting something new. This is the first episode of an investigative series — The Search for the Holy Grail of Real Estate. I'm going into the field, talking to the smartest people I can find, and piecing the evidence together as I go. In this episode, I lay out what the Holy Grail is, why...
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Jun Choo: Customer Problems First
Jun Choo, Chief Operating Officer of Zillow, and I discuss the launch that agents hated (and the lessons it taught about empathy), why Zillow Home Loans is really a trust business, how Zillow allocates resources, why the 10% revenue share with listing agents on Zillow Preview is such a big deal,...
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Rory Golod: Balance of Power
Rory Golod, President of Growth at Compass International Holdings, and I discuss what it's like to go from 20 agents to 340,000 across 120 countries, why the Rocket/Redfin partnership is about shifting the balance of power back to agents, not holding grudges against former adversaries, what he...
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Guy Gal: Coming Soon Stratagems
Guy Gal, CEO and co-founder of Side, and I discuss why he was one of Zillow Preview's launch partners, the pre-marketing and iBuying parallel, why pre-marketing is a solution searching for a problem, the real problem nobody in the industry wants to address (too many part-time agents), how...
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Deep Dive: The Redfin & Compass Deal
Rocket's Joe Rath and I unpack the recently announced Compass & Redfin partnership, that, among other things, will see Compass's exclusive listings appear on Redfin. We cover the specifics of the deal and the "why" behind it all -- from what Rocket is trying to accomplish, to why Compass, and…
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Emily Girard: MLS Whack-A-Mole
Emily Girard, CEO of Unlock MLS and the Austin Board of Realtors, and I discuss morning dopamine hits, how I ruined her weekend, the Google listings fiasco, why she hates being reactionary, why an MLS exists, why no one can force private listings, the “what’s best for the consumer” fallacy, what...
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Deep Dive: The Portal Wars
From deep inside the world of real estate portals, Scott Bond and I have an intelligent conversation about the past, present, and future of the Portal Wars. We look at the competitive landscape, how we got to today, why it’s trendy to hate Zillow, evaluate Homes.com’s strategy, look at the most...
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What Didn't Work: Aalto
This is the first episode of a new series: What Didn't Work. I'm diving into the real estate companies and ideas that just didn't work out, unpack exactly why, and reveal the key lessons learned -- directly from the entrepreneurs involved. My first guest (who inspired this idea) is Nick Narodny,...
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Austin Allison: Bucking the Status Quo
Austin Allison, CEO and co-founder of Pacaso (and dotloop), and I discuss what makes a real estate startup successful, the advantage of raising money from retail investors, why you need agents on your side, why we’re all resistant to change, surviving the past two years, listening to constructive...
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Deep Dive: Building the Brokerage of the Future
If I were to start a real estate brokerage today, what would it look like? In this long-form conversation, I sit down with Austin broker-owner Eric Bramlett to answer that question. We cover: 1. What’s broken in brokerage today -- from “masses of asses” recruiting and misaligned incentives to the...
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Garth Graham: The 7 Deadly Sins of Mortgage
Garth Graham, Senior Partner at Stratmor Group, and I chat about the biggest problem in mortgage, the cost of origination ($12k), optimizing the consumer experience, being worse than you think, spending bad money after good, the loan officer compensation issue, training AI models, what consumers...
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Deep Dive: The Redfin Post-Mortem
Let’s try something new. I’m joined by Carey Armstrong for a deep dive on Redfin — the business, the model, and the legacy. With Redfin’s acquisition by Rocket, one chapter closes and another begins, so let’s see what we can learn. Over an hour and forty minutes, we unpack Redfin’s history, do a...
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Varun Krishna: How Do I Get You A Loan
Varun Krishna, CEO of Rocket, and I discuss when to pick up your phone in the morning, being a newcomer to the housing industry, what he wishes he knew when he joined Rocket, the industry’s adversarial dynamic, AI as the removal of experience, why he got the top job, structuring the org chart to...
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Levent Künzi: Aiming for #1 in Switzerland
Levent Künzi, CEO at Switzerland’s Properti, and I discuss disruption and data limitations in European markets, sustainable growth, going against the grain of an end-to-end ecosystem, moving faster with more focus, international inspiration, permanently improving yourself, generating seller…
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Lisa Farrar: The Hemnet Strategy
Lisa Farrar, COO at Sweden’s leading real estate portal Hemnet, and I discuss starting your day with a forest run and swim, the importance of clarity in strategy, Hemnet’s top KPIs, balancing demands of different customer groups, partnering with agents, balancing a portal’s role in exclusive...
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Lukas Rose: Exclusive Inventory in Europe
Lukas Rose, CEO of Germany’s ProperBird, and I discuss the exclusive inventory power dynamics across Europe, how it encourages competition, the U.S. being the exception and not the rule, how to monetize home seekers, why tech adoption is so slow, killing new ideas, and why an agent’s top lead...
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Rory Golod: Executing Like Hell
Rory Golod, president of Growth and Communications at Compass, and I discuss his 10 year journey at Compass, focus as a luxury, building boring products, being a lightening rod in the industry, companies as confusion machines, the inventory strategy and its momentum, outworking your competitors…
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Justin Messer: Hand-to-Hand Combat in Mortgage
With $7.3B in mortgage origination volume in 2024, Justin Messer, CEO of Prosperity Home Mortgage, and I discuss being affiliated with Berkshire Hathaway, why attach rates top out at 25%, where tech is having an impact, why being on the road is a winning formula, powering a 15 minute…
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Steve Sanders: The Real Estate Branding Masterclass
Steve Sanders, with deep brand and marketing experience from working with Zillow and Pacaso (and fellow CU Boulder professor), and I chat about key learnings from iBuyer consumer research, the power and limits of Zillow’s brand, the importance of differentiation, which iBuyer is getting it right,...
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Damian Eales: Focus, Focus, Focus
Damian Eales, CEO of realtor.com, and I talk about the necessity of disciplined focus, the origin of the flat white, turning negatives into opportunities, partnering with your closest competitor, leveraging News Corp assets, doing the right things in the down cycle, why everything starts with...
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Mike DelPrete: Ask Me Anything
Joe Rath interviews me! We discuss trends in real estate tech, what’s surprised me, the impact of AI, the best product not winning, great ways to incinerate millions of dollars, the only thing that matters to portals, the “perfect house” fallacy, the decreasing value of a lead, psychological...
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Sean Soderstrom: Actual Solutions for Actual Problems
Sean Soderstrom, CEO and co-founder of Courted, and I discuss goat yoga, working in a sauna, motivation vs. inspiration, predicting agent migration, solving actual problems, strategic mistakes, unbundling the brokerage business model, recruiting innovation at Compass, the value of the Hub, making...
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Tamir Poleg: The Agent Value Equation
Tamir Poleg, co-founder and CEO of Real, and I discuss work days beginning at 3pm, how agents are underserved, growing from 800 to 22,000 agents in four years, what he would do as CEO of an incumbent, how everyone failed with tech, the one stop shop graveyard, replacing 90% of agent tasks with…
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Wendy Forsythe: Just Do It
Wendy Forsythe, CMO at eXp Realty, and I discuss why the industry is so slow to change, tech that’s moving the needle, the last mile solution, what agents really want, the power of scale, international network effects, how to talk to human beings, corporate bingo, and rate the job performance of...
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Jeremy Wacksman: The Tech to Power the Industry
Jeremy Wacksman, CEO of Zillow, and I talk about taking big swings, celebrating failure through learning, constructive feedback from customers, why clear cooperation is such a big deal, extending the Zillow brand, the changing value of a lead, solving the last mile problem, making less people…
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Mark McLaughlin: Come And Get It
Mark McLaughlin, interim president at Compass, and I discuss the 9x Pacific Union turnaround, downsizing until someone screams, either growing your market share or slowly going out of business, the hardest part of getting acquired, brainstorming without financial constraints, his greatest...
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Chris Heller: Immutable Laws of Real Estate
Chris Heller, president of Movoto and former CEO of Keller Williams, and I talk about the importance of making decisions fast, learning from mistakes, how consumer behavior is changing, agent natural selection, operating in an industry without logic, building real relationships, and there being…
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Gene Millman: The MLS Breakdown
Gene Millman, most recently the CEO of REcolorado, and I discuss the nuts and bolts of MLSs, if they are still relevant in 2024, consolidation, reinvention, how to run an MLS like a business, why disruptors need MLSs, their top threat, the biggest tech pain point, and the critical importance of...
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Greg Schwartz: Growth is in Our Control
Greg Schwartz, CEO of Tomo and former Zillow president, and I discuss cold showers, the durable real estate agent model, what's changing fast and slow, turning the lights off, why portal traffic isn't real, the birth of Tomo on a train platform in Tokyo, making mistakes quickly, and Greg's goat...
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Hari Krishnan: Proptech in Southeast Asia
Hari Krishnan, CEO of Southeast Asia's PropertyGuru, and I discuss the demographics of emerging markets, an emerging middle class fueling housing growth, the benefits and challenges of operating in multiple markets, building trust and transparency, SE Asia's data opportunity, responding to AI's...
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Court Cunningham: From Growth to Profitability
Court Cunningham, CEO of Orchard, and I discuss sunrises, the job of a CEO, six years of learnings, the land of 1,000 edge cases, wasteful spending, knowing what not to do, being too good to be true, the Orchard pitch to agents, why the salaried agent model doesn't work, being impaled on CAC,...
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Megan Meyer Toolson: The Opendoor Equation
Megan Meyer Toolson, Opendoor's President of Sell Direct & Services, and I talk about the typical Opendoor customer, the trust equation, celebrating progress, navigating a changing market, early arrogance, the $2 trillion question, rationally slow adoption, learning from customers, Opendoor's...
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Leo Pareja: Time, Luck, and Outliers
Leo Pareja, Chief Strategy Officer at eXp Realty, and I discuss time compression, why the industry is slow to change, busting NAR settlement hype, buyer agents not going away, treating your buyers like your sellers, the rise of the super team, pain killers vs. vitamins, and never being qualified.
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Tim Heyl: The Power Pivot
Tim Heyl, founder and CEO of Homeward, and I discuss morning clarity, eating the frog first, making 1,000 calls/day, magically attracting sellers, not moving too fast, hacking "buy before you sell," making hard decisions fast, what it would take for Homeward to fail, and giving more power to the...
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Jeremy Hofmann: Start With Strategy
Jeremy Hofmann, Zillow's CFO, and I discuss making agents more efficient, Zillow's core insight, being a great coach, parenting advice, agents as the last mile, Zestimates, the super app vision, current AI applications, operational discipline, the key Zillow Offers learning, and my annoying...
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Sam Sawyer: New School Model, Old School Value
Sam Sawyer, founder and CEO of Pinnacle Realty Advisors, and I take time from the Hub event to chat about his subscription-based brokerage, the commission split gray area, selling his last company to Compass, building a brokerage app store, having a new school model with old school value, being a...
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Joe Rath: The Mother of All Metrics
Joe Rath, Redfin's Senior Director of Brokerage Ops and Head of Industry Relations, and I chat about coffee subscriptions, the mother of all metrics, thinking small, the power of consistency, 100% tech adoption, the "your listing, your lead" counterfactual, the industry's most effective…
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Lacey Conway: Learning from Disruptors
Lacey Conway, CEO of Latter & Blum, and I discuss New Orleans coffee, incumbents going extinct, calculated gambles, acquiring a challenger brand, MLS innovation, power steering & lane assist, the fiefdoms of the status quo, and what she's learned from listening to this podcast.
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Scott Trench: Power of Mom-and-Pop Investors
Scott Trench, CEO of BiggerPockets, and I bust myths about the U.S. rental market and the prevalence of institutional investors, dig into the minds of 17 million mom-and-pop investors, and discuss dance parties, opportunity through inefficiency, investor demographics, why tech isn't adopted,...
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Chris Kelly: The Brokerage Pretzel
Chris Kelly, EVP at HomeServices of America, and I discuss the challenge of incumbency, why attaching mortgage is hard, Homes.com vs. Zillow, how NAR can improve, leading with transparency, the benefits of not being a tech company, why real estate is like farming, and the unintended consequences…
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Orly & MDP: The Real Estate Innovation Hub
Orly and I discuss the upcoming Real Estate Innovation Hub, a new event I'm hosting in Boulder, CO. As an attendee, Orly discusses why she applied, the benefit of collaborating with nine other industry leaders, which business challenges she wants to unpack, the intersection of tech + humanity…
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David Mele: Compete Where You Can Win
David Mele, president of Homes.com, and I discuss Dunkin Donuts coffee, post-acquisition growth, lead gen hell, the 97% opportunity, innovator's dilemma, exclusive content, strategic clarity, what's in Andy's head, and what he would do if he were Zillow's CEO.
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Dan Duffy: Ground the Static
Dan Duffy, CEO of United Real Estate Group, and I discuss United's quiet growth story, agent migration, fancy-pants MBAs, M&A breakage, the 3 attributes of a successful partner, cultural incongruity, CEO scar tissue, positive disruption, founder equity, Calvinball, and minding the value gap.
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Glenn Sanford: Building the Future
Glenn Sanford, CEO and founder of eXp Realty, and I discuss morning rituals, the push/pull of a down market, where ideas originate, game-changing tech, going against conventional wisdom, the power of pure-plays, overcoming a crisis of confidence, the sell-side pivot, and how to screw anything up.
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Robert Reffkin: Coffee, Compass, and Culture
Robert Reffkin, CEO and founder of Compass, and I discuss caffeination strategies, connectivity > productivity, how Compass became #1, learnings about building tech, 3 things agents care about most, what makes smart people stupid, sending messages back in time, and culture as a competitive...
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Steve Capezza: Lessons Learned across Real Estate
Steve “Capz” Capezza, president at Side and former SVP at Zillow, and I discuss brokerage learnings, the inertia of community, agent power, picking a funnel, full-contact leadership, what’s fueling Side’s best year, the future of brokerage, and the most impactful piece of tech in real estate.
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ABOUT THIS SHOW
Conversations with industry leaders about the businesses and technologies changing real estate.
HOSTED BY
Mike DelPrete
CATEGORIES
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How many episodes does Context with Mike DelPrete have?
Context with Mike DelPrete currently has 58 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Context with Mike DelPrete about?
Conversations with industry leaders about the businesses and technologies changing real estate.
How often does Context with Mike DelPrete release new episodes?
Context with Mike DelPrete has 58 episodes. Check the episode list to see recent publication dates and frequency.
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Who hosts Context with Mike DelPrete?
Context with Mike DelPrete is created and hosted by Mike DelPrete.
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