Founder Problems Podcast

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.  

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.  

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.

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.  

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.  

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      

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.  

In this episode, Lee Zuvanich, Zach Oshinbanjo, and Sarah Schumacher tackle the once in a year task of planning the next one. From Pinterest-level vision boards to X-men and mortar inspired operational plans, we cover three wildly different planning styles that all end up being mostly the same (hint: start with values). Yes, the ubiquitous rocks and pebble illustration is mentioned, but only once.   Mentioned In This Episode: Measure What Matters by John Doerr The 12 Week Year by Brian Moran How You Spend the First Week of 2025 - smschumacher.com Bullet Journaling: What It Is and Why I Do It - 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.  

Zach Oshinbanjo, Lee Zuvanich, and Sarah Schumacher talk about their personal founder journeys and why they decided to start this podcast. Common threads include: an uncanny ability to see problems and an insatiable drive to fix them, how entrepreneurship is an effective tool to create fulfilling careers, and the significance of community for founder support. Mentioned in this Episode: The E-Myth by Michael Gerber Traction by Gino Wickman Kaufmann FastTrac Courses SBDC ElevationLab Course 1 Million Cups KCSourceLink KCSL Resource Navigator   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.

Sarah Schumacher, Lee Zuvanich, and Zach Oshinbanjo each give a summary on what the Founder Problems Podcast is all about.