In this episode of the Founder Problems Podcast, Zach Oshinbanjo, Sarah Schumacher, and Lee Zuvanich discuss whether to quit your secure 9-to-5 for your startup idea. They examine the pros and cons of maintaining a day job while exploring side ventures, highlighting the importance of stability and a gradual transition while totally unable to hide their bias toward entrepreneurship (but do it strategically, please).

Timestamps

00:00 Introduction to the Founder Problems Podcast

00:20 Meet the Hosts: Zach, Sarah, and Lee

00:56 Defining the Day Job

01:10 The Positives of Keeping Your Day Job

02:23 Balancing a Day Job and a Side Hustle

06:06 The Glamour and Reality of Startups

08:37 Transitioning from Day Job to Full-Time Startup

13:17 Navigating Multiple Roles and Responsibilities

17:57 Managing Time and Outsourcing Tasks

20:45 Balancing Full-Time Work and Freelance Gigs

21:17 Too Old for All-Nighters

21:52 Navigating Pitch Competitions and Job Interviews

23:04 Disclosing Side Hustles to Employers

25:59 The Digital-First Lifestyle

27:02 The Comfort of a W2 Job

29:02 Entrepreneurial Challenges and Personalities

30:24 Juggling Multiple Responsibilities

34:26 Deciding Between Day Jobs and Startups

40:40 Concluding Thoughts on Founders' Dilemmas

Founder Problems is a podcast by and for real-world, fed-up founders. Three entrepreneurs in the messy middle share hot takes, actionable steps, and resources to navigate the challenges of running a business—no promises of 10x growth or swooning investors. Every founder’s journey is different, so take what works and make it your own.

Learn more at founderproblems.com.