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.

In this episode of the Founder Problems Podcast, Sarah Schumacher, Lee Zuvanich, and Zach Oshinbanjo discuss the idea of rented versus owned digital platforms. Because social media accounts are great until they decide to pull the rug out from under you. They break down the pros and cons, sprinkle in a few realistic warnings, and give practical tips on leveraging both types to boost your personal brand. They even discuss why having your own server in your basement is a terrible idea.

Timestamps:

00:00 Introduction to Founder Problems Podcast

00:30 Rented Platforms: Pros and Cons

00:55 Networking and Personal Branding on Social Media

07:40 The Importance of Owned Platforms

08:41 Risks and Strategies for Digital Ownership

14:33 Technical Aspects of Data Transferability

18:51 The Reality of Social Presence Management

19:19 Adapting to Changes in SEO and AI

19:48 Pros and Cons of Self-Hosted Websites

20:15 Marketing Your Website Effectively

20:56 Strategic Use of Social Media

26:29 The Importance of Control and Ownership

34:01 Final Thoughts and Practical Examples

Mentioned In This Episode:

• Stop Building Your Online Presence on Rented Internet Platforms - smschumacher.com
• 5 Reasons GoDaddy Is Terrible And You Should Run Now - cyclonepress.com

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 insightfully honest episode, Lee Zuvanich, Zach Oshinbanjo, and Sarah Schumacher dive into TAM, SAM, and SOM (no, that’s not a delicious soup). They drive home the importance of understanding your Total Addressable Market (TAM) and listening to feedback before assuming your next idea is the big one. Don't spend all your money on ads and accolades before you even know what your market wants.

Timestamps:

00:00 Introduction and Hosts' Backgrounds

00:40 Understanding Market Sizing: TAM, SAM, SOM

04:15 Common Mistakes in Market Entry

06:00 Challenges in Customer Acquisition

08:18 Misidentifying Your Market

17:04 Finding Product-Market Fit

21:26 User Research and Market Validation

22:17 The Beta Tease and Market Missteps

23:00 Testing Product Market Fit

23:10 MVPs and Real-World Testing

24:15 Marketing Challenges and Misconceptions

25:33 Understanding Your Market

28:31 Lifestyle Business vs. Startup

40:20 Effective Communication and Positioning

41:41 Final Thoughts and Takeaways

Mentioned In This Episode:

• Red Ocean
• Just Start - smschumacher.com

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, Lee Zuvanich, Sarah Schumacher, and Zach Oshinbanjo discuss the difficult task of vetting potential co-founders. Sharing personal misadventures and cautionary tales, they stress the importance of thorough due diligence with practical tips like working together on a trial basis, ensuring aligned values, and the critical need for trust and integrity. Spoiler alert: A mutual love for scotch or golden doodles isn't quite enough to seal the deal.

Timestamps:

00:12 Personal Experiences and Perspectives

01:03 The Importance of Due Diligence

01:59 Building Trust and Relationships

02:29 Practical Approaches to Vetting

04:38 Challenges and Ethical Considerations

13:57 Networking and References

15:48 Navigating Skepticism and Synergy

16:54 The Leap of Faith in Business

17:57 Defining Roles and Accountability

19:01 The Importance of Integrity

21:38 Money Matters in Partnerships

25:27 Balancing Passion and Compensation

27:19 Evaluating Potential Partners

30:26 Tools and Tactics for Success

31:18 Wrapping Up: Founder Problems

Mentioned In This Episode:

• Y Combinator Cofounder Matching Platform

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.

Zach Oshinbanjo, Lee Zuvanich, and Sarah Schumacher delve into the myth that a singular focus is necessary for business success. Sharing their eclectic and, frankly, exhausting career paths, they highlight the ability to balance multiple ventures by utilizing systems and leveraging natural nerd skills. They also give advice to their younger selves: underscoring the value of experimenting and following interests, and being ok with being different.

Timestamps:

00:00 Meet the Hosts: Diverse Backgrounds and Expertise

00:47 Debunking the Myth of Singular Focus in Business

01:58 Balancing Multiple Roles and Income Streams

03:30 The Importance of Experimentation and Finding Your Niche

07:36 Turning Hobbies into Income-Generating Ventures

15:23 The Role of Systems and Organization in Managing Multiple Projects

18:54 The Power of Simple Systems

19:56 Managing Energy and Fatigue

21:17 Navigating Professional Challenges with ADHD

22:04 The Journey of Entrepreneurship

24:31 The Importance of Intuition in Business

27:51 Advice for Aspiring Entrepreneurs

30:03 Reflecting on Career Paths and Choices

34:33 Encouragement for Multi-Passionate Individuals

38:10 Final Thoughts and Call to Action

Mentioned In This Episode:

• Ikigai concept
• Unity (game engine)
• USAspending.gov
• SAM.gov
• Getting Things Done by David Allen
• ClickUp
• Readdle Calendar (Zach)
• Fantastical (Sarah)
• Multi-passionate, Multi-hyphenate, Multi-potentialite?

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, Lee Zuvanich, Sarah Schumacher and Zach Oshinbanjo dive deep into the multifaceted decision-making process of knowing when to throw in the towel. Enduring feast and famine business cycles, investor pressure, being too busy to listen... they discuss their own experiences with the mental gymnastics behind tough decisions. Expect insights on how anxiety can be helpful, the importance of intuition, and balancing the thrill of the idea with insights from the real world. Plus, hear why ignoring your mom's business advice might be the best move you'll ever make. If you've ever wonder how other founders differentiate between burnout and strategic pivots, this candid, conversation should be eye-opening.

Timestamps:

00:32 Personal Struggles and Business Cycles

01:48 Advice from Mentors and Entrepreneurs

03:26 Balancing Mental Health and Business

05:52 Trusting Your Intuition

06:18 Defining Success and Risk

07:13 The Role of Anxiety and Intuition

08:24 The Decision to Quit

13:29 Capturing and Evaluating Ideas

22:05 Grieving and Moving On

24:29 Conclusion: The Entrepreneurial Spirit

Mentioned In This Episode:

• Pain x Resistance = Suffering
• Loonshots by Safi Bahcall (Akira Endo and the Heart of Stone – Chapter 2)

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.