Seemed Like a Good Idea

In the very first episode of Seemed Like a Good Idea, I’m thrilled to kick things off with none other than Spencer Rascoff, Co-Founder and former CEO of Zillow and the current Chairman of Pacaso. Spencer’s career has been filled with high-stakes decisions and fascinating lessons, making him the perfect guest to start this journey with.

In this episode, we dive into some of the most important moments in Spencer’s career:

• Why Pacaso had to scale back and implement layoffs after rapid growth
• Zillow’s failed attempt to introduce real estate auctions in the U.S.
• The current state of real estate commissions and the role of the DOJ in shaping the industry
• Insights into the challenges of launching new ventures in the social media and travel spaces

Spencer shares candid reflections on the ups and downs of entrepreneurship, offering valuable lessons for founders and executives alike.

In this episode of Seemed Like a Good Idea, I sit down with Melissa Kwan, Co-Founder and CEO of eWebinar, and a three-time bootstrapped founder with a successful exit under her belt. Melissa shares candid insights from her entrepreneurial journey, revealing the highs, lows, and lessons learned while building innovative products in the SaaS and real estate tech spaces.

• Burning Man & Creativity: Melissa reflects on her annual pilgrimage to Burning Man and how the event inspires her personal and professional life.
• Startup Life: Insights into the reality of being a founder, why most ideas fail, and how Melissa learned to embrace consistency and compounding results over quick wins.
• Affiliate Marketing Gone Wrong: Melissa opens up about spending $130,000 on affiliate marketing and why it didn’t deliver the results she hoped for.
• Remote Work Challenges: Lessons learned from hiring junior employees in a fully remote company and why Melissa now focuses on experienced, self-motivated talent.
• Real Estate Tech Realizations: Why Melissa advises against pursuing real estate tech startups, based on her hard-fought experiences with early ventures.
• Customer Support Breakthroughs: The serendipitous story of hiring a junior developer on a sailboat and how it transformed eWebinar's technical support challenges.

Tune in for an engaging conversation that delves into the realities of entrepreneurship, the importance of adaptability, and the mistakes that shaped Melissa’s journey to success.

In this episode of Seemed Like a Good Idea, I sit down with Scott Kriss, Founder of Kriss Law, one of the largest real estate closing firms in the U.S. With over 20 years in the industry, Scott offers a candid look at his career, the evolution of real estate law, and key lessons learned from economic ups and downs.

Topics Covered:

• Early Days & Growth: Scott shares his journey from law school to founding Kriss Law, expanding nationwide, and the challenges of aggressive business growth.
• Subprime Mortgage Crisis: Insights into the predatory lending practices that led to the 2008 crisis and the regulatory changes that followed.
• Real Estate Industry Today: Scott’s take on the role of buyer’s agents, the importance of legal guidance in transactions, and why he believes agents are crucial for first-time homebuyers.
• Legal & Market Changes: A discussion on recent lawsuits impacting commission structures and the ripple effects of misinformation in the real estate world.
• Investment Lessons: Scott’s experiences in investing, the pitfalls of startups, and his advice on avoiding common investment mistakes.

Tune in for a thought-provoking discussion that covers the real estate industry’s past, present, and future—and the lessons Scott wishes he’d known sooner.