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.

In this episode of the Founder Problems Podcast, Sarah Schumacher, Lee Zuvanich, and Zach Oshinbanjo navigate the murky waters of differentiating freelancers from entrepreneurs. They explore how freelancing can be a starting point for business-building, the difficulties (and risk) of scaling and delegation. The team also takes a detour into the need for personal branding and networking to avoid 'top hat' gimmicks. Key takeaways include the soul-searching exercise of using personal goals to determine business structure, leveraging personality types for optimal business roles, and starting with a 'minimum viable business' mindset.

Timestamps:

00:56 Defining Freelancers

02:23 Transitioning from Freelancer to Entrepreneur

04:59 Personal Experiences and Definitions

09:24 Challenges and Goals in Business

11:45 Visionaries vs. Integrators

17:27 Scaling and Business Strategies

20:38 The Reality of Freelancing

21:14 Career Pivots and Changing Mindsets

22:06 The Importance of Saying Yes

22:11 Customer Pursuit: Freelance vs. Agency

23:16 Word of Mouth and Marketing Strategies

26:11 Personal Branding and Networking

30:03 Building in Public: Transparency in Business

32:25 Mistakes and Pivots in Business

39:58 Finding Your Zone of Genius

41:58 Conclusion and Final Thoughts

Mentioned In This Episode:

• The E-Myth by Michael Gerber
• Traction by Gino Wickman
• Enneagram
• Myers-Briggs
• Culture Index
• Zone of Genius

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.

In this episode, Zach Oshinbanjo, Lee Zuvanich and Sarah Schumacher share how to turn your biggest facepalms and 'oh-no' moments into stepping stones. From last-minute grant scrambles to learning to cultivate optimism, they dive into personal stories and practical tips on finding the silver lining in every screw-up. They also make a diversion into public speaking tips, and give examples of how to spot red flags in business referencing a certain weird book.

Timestamps:

00:00 Introduction and Hosts Introduction

00:45 Turning Disasters into Opportunities

01:29 Real-Life Examples of Finding Silver Linings

03:22 The Importance of Narrative and Progress

05:30 Survivorship Bias and Resilience

09:21 Personal Stories of Resilience

13:55 Public Speaking and Overcoming Fear

25:42 Recognizing Red Flags in Business

34:03 Final Thoughts and Takeaways

Mentioned In This Episode:

• Opportunity Recognition
• Survivorship Bias
• The 48 Laws of Power by Robert Greene (a reference, not a recommendation…)
• How to Conduct a Premortem

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.