When is the right time to jump into entrepreneurship? In this episode, host Marcus Arredondo talks with Tyler Kastelberg, a former Wall Street pro turned real estate entrepreneur. Tyler opens up about how personal struggles and financial goals led him to create Bullpen, a thriving real estate consulting company. He also shares how overcoming challenges, including his stutter, helped shape his leadership style. Whether you’re considering starting something new or dealing with obstacles, this conversation provides honest advice on staying solid and welcoming change.

Tyler was born and raised in Richmond, VA and now lives in San Francisco with his wife and two children. His lifelong stutter has created valuable resilience that has been used to get through engineering school, work in investment banking, and ultimately, leave the nest to build Bullpen.

Episode highlights:
[0:00] Intro
[2:13] Tyler Kastelberg background and early career choices
[6:05] The challenge of competition in real estate and expressing
[10:13] Pivoting into consulting, scaling the business, and launch of Bullpen
[14:50] Raising capital and lessons learned from failure
[19:37] Resilience in entrepreneurship and personal challenges with a stutter
[27:24] The role of writing and the importance of vulnerability in building connections
[33:11] Iterating the Bullpen business model and attracting institutional clients
[40:07] Navigating tough economic times and mentorship
[43:43] Advice for younger self and reflections on entrepreneurship
[47:52] Resources for personal and professional growth
[50:33] Outro