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

    What’s Your Problem: Insurance Annoyances, Project Management and Creating Fearless Content
    2025/09/10

    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.
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    43 分
  • Let’s Talk Rebranding: Nobody Cares as Much as You Do

    Let’s Talk Rebranding: Nobody Cares as Much as You Do
    2025/08/28
    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 SearchCommon Law TrademarkDribbble.comCoolors Color Palette Generator5 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.
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    1 時間 8 分
  • From Rough Patches to Reality: When to Call It Quits on Your Startup

    From Rough Patches to Reality: When to Call It Quits on Your Startup
    2025/07/30

    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.
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    44 分
  • Summer Break

    Summer Break
    2025/06/18

    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.
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    1分未満
  • What’s Your Problem: Real Talk on Operations, Focus, and Embracing Limitations

    What’s Your Problem: Real Talk on Operations, Focus, and Embracing Limitations
    2025/06/04

    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.
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    25 分
  • All That AI BS: An Infodump of Facts, Fears and Futuristic Predictions

    All That AI BS: An Infodump of Facts, Fears and Futuristic Predictions
    2025/05/21

    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 Fucking 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
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    49 分
  • Don't Quit Your Day Job... Yet

    Don't Quit Your Day Job... Yet
    2025/05/07

    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.
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    40 分
  • Freelancing: A Minimum Viable Business

    Freelancing: A Minimum Viable Business
    2025/04/23

    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.
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    43 分