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.