Founder Problems Podcast

Lee Zuvanich, Zach Oshinbanjo, Sarah Schumacher
  • 5.0 (4)
  • ENTREPRENEURSHIP
  • UPDATED BIWEEKLY

Unscripted, anti-hustle conversations with real founders working through real problems. Behind closed doors, founders aren't talking about the highlight reels. Listen in as we help each other–and you–navigate the ups and downs of life as a business owner, whether you're on your 1st startup or your 15th.

  1. 09/10/2025

    What's Your Problem: Insurance Annoyances, Project Management and Creating Fearless Content

    In this episode of the Founder Problems Podcast, Sarah Schumacher, Zach Oshinbanjo, and Lee Zuvanich forget to record the intro, discuss Zach's construction management wins, insurance annoyance, and go down a couple rabbit holes (listing sites and project management). Sarah talks about the struggle to slow down long enough to delegate, and how rebranding never ends, while Lee shares his final fear frontier (making video content) and how the pursuit of perfection can be dangerous. We also share what seems like an obvious-in-hindsight fail for this very podcast business, because this is Founder Problems, after all.   Timestamps: 00:00 Introduction and Podcast Overview 00:58 Meet the Hosts 01:41 Zach's Recent Projects and Wins 03:23 Challenges in Nonprofit Management 11:11 Sarah's PM + Rebranding Journey 14:54 Tax Filing Woes 17:58 Project Management Insights 19:39 Onboarding New Team Members 22:00 Delegation and Documentation Challenges 23:07 Balancing Autonomy and Structure 26:15 Hiring Senior vs. Junior Talent 27:55 Personal and Professional Wins 29:57 Struggles with Content Creation 33:35 Embracing the Cringe 41:34 Final Thoughts and Encouragement   Mentioned In This Episode: Hofstadter's Law Parkinson's Law Decisive by Chip & Dan Heath Zyppy (Agency List) IRS 1065 Partnership Filing EIN (Employer Identification Number) CapCut (Video Editor) NeoCities (Website Maker)   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.

    43 min

  2. 08/28/2025

    Let's Talk Rebranding: Nobody Cares as Much as You Do

    In this extra long episode, Zach Oshinbanjo, Sarah Schumacher, and Lee Zuvanich dive deep and get practical on the art and chaos of rebranding. How do you know it's time to rebrand? Sarah reveals the emotional journey of evolving cyclone press into Tiny Thunder Studio, while Lee talks about pivoting his businesses into an AI startup. Whether you're wondering what to do when someone trademarks 'your' name right out from under you or pondering the right level of investment for a startup brand (not $230,000), this episode provides actionable takeaways for founders. Timestamps: 00:00 Welcome to the Founder Problems Podcast 00:09 Meet the Hosts: Zachary, Sarah, and Lee 00:58 The Importance of Rebranding 01:31 Sarah's Rebranding Journey 03:27 Trademark Issues and Business Names 05:49 Lee's Perspective on Branding 14:29 Zachary's Rebranding Experience 23:23 Choosing the Right Designer 24:07 The Collaboration Process in Branding 28:01 Practical Tips for Effective Rebranding 37:03 Digital and Social Aspects of Rebranding 51:11 Implementing and Launching a New Brand 52:44 Innovative Business Card Ideas 52:56 Ensuring a Successful Launch 53:27 Energy and Branding 57:45 The Importance of Preparation 01:00:09 Personalized Outreach Strategies 01:05:56 Balancing Energy and Strategy 01:06:25 Rebranding Challenges and Strategies 01:07:46 Choosing a New Business Name 01:08:37 Finalizing the New Brand Name 01:32:43 Revisiting the Rebrand Discussion 01:33:13 Trademark Troubles and Business Names 01:34:31 Navigating Trademark Disputes 01:37:02 The Importance of Branding 01:40:58 Creating a Strong Brand Presence 01:41:39 Balancing Cost and Quality in Branding 23:33 The Collaboration Process in Branding 31:07 Practical Tips for Effective Branding 02:07:03 Choosing a Startup Name 02:07:53 Color Palettes and Logos 02:11:08 Rebranding Strategies 02:12:35 Navigating New Markets 40:25 The Importance of Preparation 02:16:05 Personal Touch in Branding 02:32:43 Balancing Energy and Preparation 01:06:25 Final Thoughts and Wrap-Up   Mentioned In This Episode: USPTO Trademark Search Common Law Trademark Dribbble.com Coolors Color Palette Generator 5 Principles of Logo Design Sarah's Rebrand Announcement (see, not stodgy at all!)   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.

    1h 8m

  3. 07/30/2025

    From Rough Patches to Reality: When to Call It Quits on Your Startup

    In this episode of Founder Problems, hosts Zach Oshinbanjo, Lee Zuvanich, and Sarah Schumacher discuss the challenging decision of whether to shut down or pivot a business. Zach shares a recent realization, and they all reflect on their personal startup experiences, emphasizing the significance of community support, understanding opportunity costs, the role of luck, and maintaining a balance between perseverance and practicality. Zach offers advice on the logistical aspects of closing a business, offering insights on how to move forward effectively.   Timestamps: 00:00 Welcome to Founder Problems 00:12 Meet the Hosts 00:51 Season Two Kickoff 01:19 The Reality of Failure 02:28 Balancing Multiple Ventures 03:28 The Importance of Adaptability 05:55 Economic Challenges and Business Longevity 07:15 The Role of Investors 17:38 The Value of Community Support 18:58 Opportunity Cost and Decision Making 23:01 Recognizing When to Pivot 25:10 Navigating Career Pivots 25:46 The Myth of Overnight Success 26:14 Quitting vs. Starting Anew 28:14 The Emotional Toll of Shutting Down 30:55 Learning from Failure 36:40 The Importance of Proper Closure 38:58 Embracing New Beginnings 40:15 Reflecting on the Journey 43:21 Celebrating Endings and New Starts   Mentioned in this Episode: 36 Hours of Pain Pipeline Entrepreneurs Boddle Learning on Startland News Betty Rae's Ice Cream in Kansas City Shatto Milk Company in Kansas City   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.

    44 min

  4. 06/18/2025 · BONUS

    Summer Break

    Just a quick note to say we're taking a short summer break and will return in July.   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.

    28 sec

  5. 06/04/2025

    What's Your Problem: Real Talk on Operations, Focus, and Embracing Limitations

    In this episode, Sarah Schumacher, Zach Oshinbanjo (and joining later, Lee Zuvanich) experiment with a new format about our own, recent founder problems: tedious admin work, the art of saying no, and staying afloat when founder brain pulls you in twenty directions. We discuss Sarah's quest for operational efficiency, Zach's strategic life overhaul, and Lee's struggle with octopus-esque multitasking, in hopes it will provide you with useful tips on leveraging technology, refining your focus, and being a pragmatic pessimist (or at least some commiseration).   Timestamps 00:00 Introduction to 'What's Your Problem?' 00:38 Sarah's Week: Enhancing Operations 02:11 Zach's Week: Finding Focus 11:04 Lee's Week: Juggling Responsibilities 20:10 Takeaways and Final Thoughts   Mentioned In This Episode: The Focus Myth Episode Zapier   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.

    25 min

  6. 05/21/2025

    All That AI BS: An Infodump of Facts, Fears and Futuristic Predictions

    In this episode of the Founder Problems Podcast, hosts Lee Zuvanich, Sarah Schumacher, and Zach Oshinbanjo dive into the contentious world of AI. They explore its potential harms (DOOM!) and benefits (being lazy!), including environmental impacts, corporate responsibility, and practical applications in both personal and professional settings. The conversation also touches on the importance of developing your own style and being intentional with AI use. Timestamps: 00:00 Introduction to AI Discussion 01:12 Fears and Concerns About AI 03:54 Environmental Impact 06:13 Corporate Responsibility 11:21 Positive Aspects 21:10 Personal and Professional Uses of AI 25:59 AI in Image Editing 26:25 AI for Coding and Snippets 27:03 AI in Personal and Work Life 27:32 Custom Chat Bots and Automation 28:39 Vibe Coding 30:46 The Importance of Learning Fundamentals 33:59 The Future of AI in Creative Fields 39:49 AI's Ubiquity and Ethical Considerations 45:01 Intentional Use of AI 47:06 Final Thoughts and Takeaways   Mentioned In This Episode: Boston Dynamics Robot (Video) Figure Robot (Video) Cerebras Generative AI: How will it affect future jobs and workflows? (McKinsey) "I Will F*****g Piledrive You If You Mention AI Again" - Ludic (one of Sarah's favorite writers on the Internet) Sarah's AI Newsletter Series: OK Fine, I'll Talk About AI [Part 1] How I Use AI [Part 2] The Philosophical Baggage of AI [Part 3] Tools: Perplexity Otter Reclaim Fathom.video ChatGPT Custom GPT Claude Projects ClickUp AI

    49 min

  7. 05/07/2025

    Don't Quit Your Day Job... Yet

    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.

    40 min

  8. 04/23/2025

    Freelancing: A Minimum Viable Business

    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.

    43 min
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About

Unscripted, anti-hustle conversations with real founders working through real problems. Behind closed doors, founders aren't talking about the highlight reels. Listen in as we help each other–and you–navigate the ups and downs of life as a business owner, whether you're on your 1st startup or your 15th.

Information

  • Creator
    Lee Zuvanich, Zach Oshinbanjo, Sarah Schumacher
  • Years Active
    2024 - 2025
  • Episodes
    17
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    Founder Problems Podcast