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 important metric to track (trust), and sprinkle in international examples and learnings.

We then shift to the two Power Plays that will shape the portal landscape for years to come: the end-to-end ecosystem and exclusive inventory. We talk about why it’s going to be an absolute grind, the challenge of selling mortgages, why I don’t do all my shopping at Target, and, yet again, why agents are absolutely indispensable.

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, CEO and founder of Aalto, which just didn't work out. With over $50M raised from top tier VC firms, Aalto was a private listing marketplace and then pivoted to a "digital agent" once Clear Cooperation shut down their business. In the end, neither idea worked.

Nick opened up about exactly what didn't work, why, and what he learned through the process. From navigating buyer emotions in real estate to product market fit suction to the three hurdles of fear, these are hard-fought learnings that I think everyone in the space should know!

I'm doing this for two reasons. First, I want to reduce the stigma around talking about failure. Nick didn't fail. He tried and learned, and that should be celebrated. Second, I want to capture and publish these valuable learnings, which are really worth their weight in gold for other would-be proptech entrepreneurs in the space.

Not everything is great all of the time. Sometimes things don't work out. Let's explore why, and get smarter together. Thanks for your vulnerability and openness, Nick.

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 feedback, skepticism as a validator of new ideas, and what he would do differently if he had to do it all over again.

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 flood of part-time agents and industry noise.

2. What’s actually working -- the common threads between the brokerages and agents thriving, including eXp’s recruiting flywheel, Compass’s communications machine, various new business models, and the overlooked importance of emotional value and culture.

3. How we’d build it from scratch -- a focused brokerage designed for the top 20%: lean, selective, efficient, culture-rich, and boringly effective.

The themes that emerge again and again: focus, clarity, culture, recruitment, and communication. If you want to understand where brokerage is heading -- and what it really takes to compete where you can win -- this is for you!

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 really hate (the 7 deadly sins), what makes a great loan officer, and why Garth will never be on my podcast again.

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 deep dive into the business model(s), discuss key challenges and structural issues, and wrap it all up with some timeless lessons learned.

Among other things, we talk about:

• The vision behind the employee-agent model
• Why Redfin never really scaled profitably
• The consumer site everyone loved — but didn’t monetize
• Big bets on rentals and mortgage that didn’t pay off
• And what happens when you try to do everything at once

This is the first long-form podcast I've done. Let me know what you think!

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 match strategy, different vs. better, the art of customer-driven innovation, and how to get big companies to innovate.

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 leads, why brand is so important, and exclusive listings in the Swiss portal landscape.

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 listings, copying with pride, a specific product f*ck up, and moving fast vs. moving perfectly.

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 sources are his dog, his kids, and firefighters.

Here's the research I mention: Scout24: Growing a New Consumer Revenue Stream