Porch Swing Podcast

Clayton Collins, CEO of HousingWire, joins Justin Benson, George Laughton, and guest host Kala Laos, CEO of Zoodealio, to talk about leaving investment banking for entrepreneurship, how he used a search fund to acquire HousingWire, and how his leadership style has evolved over 10 years.

He also covers running a remote team, keeping a growing company from becoming bureaucratic, what surprised him about real estate’s coaching culture, and the 2021 moment that taught him to trust his team.

🔔 Subscribe to Porch Swing Podcast today: https://youtube.com/@porchswingpod?sub_confirmation=1

Resources:
https://hwmedia.com/

⏰ Timestamps:

00:00–01:27 HousingWire CEO Clayton Collins pulls up a seat on the porch

03:22 Warren Buffett’s folksy image was a strategy

04:00 From investment banker to entrepreneur

06:26 Search funds: The entrepreneur path for people without the big idea

07:15 How Collins found HousingWire

09:13 The one question that built his investor network

13:23 “Have a bias toward action.”

15:25 Munger’s rule and how Collins’ experience was different

16:55 What Collins would tell young entrepreneurs today (that he wished he’d known)

20:52 Kala: “What didn’t you know that quickly uncovered once you stepped in?”

23:23 The CEO’s hardest question: How do I change as the business changes?

24:16 His first big bet as a leader: Hiring a sales leader

25:05 How his leadership style has changed from 2016 to 2026

28:19 What surprised him most about the real estate industry

34:20 Missing his first RealTrends event for his son’s birth

39:08 What Collins would look for in a chief of staff

48:41 What Collins would warn his 2016 self about

51:14 Is 4 million sales the new baseline?

53:30 “Hard markets forge careers and they forge great companies.”

55:27 Beyond family, the people Collins wants to thank for the life he’s built

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✅ Stay Connected With Us

👉 Connect with Justin Benson: https://www.instagram.com/justinbenson/

👉 Connect with George Laughton: https://www.instagram.com/georgelaughton/

👉 Connect with Kala Laos: https://www.instagram.com/kalalaos/

👉 Connect with Clayton Collins: https://www.instagram.com/housingclayton/

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BAM PARTNERS

𝐒𝐡𝐢𝐥𝐨 is the intuitive AI assistant built for high-performing real estate teams that listens, coaches, and guides your agents in real time so they can close with confidence → https://shilo.ai/

#entrepreneurship #realestatecoaching #investors

James Dwiggins, President of NextHome, joins Justin Benson and George Laughton to discuss why he sold NextHome to eXp, his fear the MLS won't survive five years, why he calls private listings an abomination, why most proptech won't survive AI, and why agents pick the broker before the brand.

🔔 Subscribe to Porch Swing Podcast today: https://youtube.com/@porchswingpod?sub_confirmation=1

James Dwiggins' Podcast, Real Estate Insiders Unfiltered: https://www.youtube.com/@RealEstateInsidersUnfiltered

⏰ Timestamps:

00:00–01:38 Intro

05:00 “Always say the things you don’t think you can say.”

06:23 How James Dwiggins got to where he is as President of NextHome

12:15 Why the use of a real estate agent is at an all-time high

19:24 The 1st thing Dwiggins & his business partner created: virtual tours

20:33 The founder’s curse: too far ahead in a late-adopting industry

23:28 There’s no key to success. “The question is what are you willing to give up to get there.”

27:15 Why most proptech companies won’t survive (and what separates those that will)

31:20 Messy middle moments and what Dwiggins learned from them

33:55 “The hardest part as a founder is knowing when to make a tough call.”

34:47 The $20K payroll loan that taught him "Your word is everything"

37:33 The problem with leadership: “the leader doesn’t know when to get out of the way.”

40:12 Stretched to the brink in 2024: Why Dwiggins spoke out knowing he’d be sued

44:44 “If the MLS goes down, the whole system fails.”

46:32 NextHome’s acquisition by eXp and why private listings are “an abomination”

50:03 Why Dwiggins fears the MLS won’t survive the next five years

53:00 “Agents choose the broker first. They choose the brand second.”

56:48 People (outside family) Dwiggins wants to thank for the life he built.

———

✅ Stay Connected With Us —

👉 Connect with Justin Benson: https://www.instagram.com/justinbenson/

👉 Connect with George Laughton: https://www.instagram.com/georgelaughton/

👉 Connect with James Dwiggins: https://www.instagram.com/james.dwiggins/

———

🔔 Subscribe to the BAM YouTube channel: https://tinyurl.com/aatxhaka

📩 Subscribe to BAM Newsletter: https://newsletters.nowbam.com/bam-daily

🧐 Check out BAM: https://nowbam.com/

BAM PARTNERS

𝐒𝐡𝐢𝐥𝐨 is the intuitive AI assistant built for high-performing real estate teams that listens, coaches, and guides your agents in real time so they can close with confidence → https://shilo.ai/

#JamesDwiggins #realestate #proptech

Leo Pareja, Chief Executive Officer at eXp Realty, joins Justin Benson, George Laughton and Lindsay Fricks to discuss his journey from tech entrepreneur to real estate CEO, why great leaders learn to love solving problems, and how adversity shapes confidence. They also unpack redefining success beyond building a bigger company and managing time, family and the demands of leadership.

🔔 Subscribe to Porch Swing Podcast today: https://youtube.com/@porchswingpod?sub_confirmation=1

———

✅ STAY CONNECTED WITH US

👉 Connect with Justin Benson: https://www.instagram.com/justinbenson/

👉 Connect with George Laughton: https://www.instagram.com/georgelaughton/

👉 Connect with Lindsay Fricks: https://www.instagram.com/lindsay.fricks/

👉 Connect with Leo Pareja: https://www.instagram.com/leopareja/

———

🔔 Subscribe to the BAM YouTube channel: https://tinyurl.com/aatxhaka

📩 Subscribe to BAM Newsletter: https://newsletters.nowbam.com/bam-daily

🧐 Check out BAM: https://nowbam.com/

BAM PARTNERS

𝐒𝐡𝐢𝐥𝐨 is the intuitive AI assistant built for high-performing real estate teams that listens, coaches and guides your agents in real time so they can close with confidence → https://shilo.ai/

#LeoPareja #eXp #RealEstate

In the debut episode of Porch Swing, Tom Ferry joins Justin Benson, George Laughton, and Lindsay Fricks for an honest talk about ambition, fear, protecting your mind like an athlete protects their body, and why constraint tends to create the biggest breakthroughs.

🔔 Subscribe to Porch Swing Podcast today: https://youtube.com/@porchswingpod?sub_confirmation=1

⏰ Timestamps:

03:16 The Biochemistry Degree Nobody Saw Coming
07:36 Why Your Mind Is the Only Tool You Actually Have
12:18 The Conversation That Changed Tom Ferry’s Career
18:36 Munger's Paradox: Never Underestimate the Man Who Overestimates Himself
26:47 The "Brutal Public A** Kicking" Every Ambitious Person Needs
37:51 The Defensive Reaction That Kills Ambitious People's Growth
47:31 Jim Carrey's Commencement Line on Letting Go of Outcomes
59:58 The Inman Rant on AI Being Wrong All the Time (and Why That's Fine)
01:03:22 You Can't Just Be a Door Opener Anymore

———

✅ Stay Connected With Us —

👉 Connect with Justin Benson: https://www.instagram.com/justinbenson/

👉 Connect with George Laughton: https://www.instagram.com/georgelaughton/

👉 Connect with Lindsay Fricks: https://www.instagram.com/lindsay.fricks/

👉 Connect with Tom Ferry: https://www.instagram.com/tomferry/

———

🔔 Subscribe to the BAM YouTube channel: https://tinyurl.com/aatxhaka

📩 Subscribe to BAM Newsletter: https://newsletters.nowbam.com/bam-daily

🧐 Check out BAM: https://nowbam.com/

BAM PARTNERS

𝐒𝐡𝐢𝐥𝐨 is the intuitive AI assistant built for high-performing real estate teams that listens, coaches, and guides your agents in real time so they can close with confidence → https://shilo.ai/

#TomFerry #RealEstateCoaching #RealEstatePodcast