Founder Problems Podcast

In this episode, the hosts admit that (at the time of recording) it was the first week after school started and everyone's exhausted. Wins center on kids being back in school and the return of quiet workdays; struggles include client flakiness and boundaries, AI making "cheapskates free to be cheapskates," slow business by choice, and frustration with clients going DIY/AI and failing to communicate about budgets or unpaid bills.

Timestamps:

• 00:00 Welcome and Introductions

• 01:02 Wins After School Starts

• 02:09 What Is WWOOF

• 03:34 Reading Between Reviews

• 05:13 Empty Nest and Freedom

• 06:10 Sarah Back to Work Mode

• 07:08 Burnout and AI Websites

• 08:55 Zach Joins READY Program

• 10:43 Workout Routines and Disc Golf

• 15:53 Struggles and Client Boundaries

• 19:16 Foreboding Joy and Stability

• 21:03 Billionaire Talk and Calendly

• 23:28 Google Disruption and Moats

• 26:08 Sarah Struggle Caring Less

• 26:25 Burnout After Two Decades

• 26:41 AI Cheapskates Problem

• 27:24 Why Hosting Builds Trust

• 28:32 Losing A Beloved Client

• 29:55 Payment Silence Vs Honesty

• 31:15 Stricter Client Boundaries

• 35:21 Canva AI Site Reality Check

• 36:47 Building AI Website Package

• 38:26 Humans In The Loop Model

• 43:17 Zach Key Man Bottleneck

• 49:34 Earned Revenue Experiments

• 53:01 Lee Focuses On Startup

• 56:27 R And D And Wrap Up

Links Mentioned In This Episode:

• Organization: WWOOF

• Reddit Thread: Workaway

• Organization: REDI

• Concept: 'Forboding Joy'

• Income Happiness: ("Globally, we find that satiation occurs at $95,000 for life evaluation and $60,000 to $75,000 for emotional well-being.")

• Wikipedia: Tope Awotana

• Podcast: How I Built This: Tope Awotana

• Tool: Tidycal

• Platform: Aptible

• KC Program: ProX

• KC Program: Northland CAPS

• KC Program: Worktern

• Founder Doing everything behind the scenes story: Chattjb

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.

After opening with a recording snafu (because it's funny), the hosts dive into "runaway founder syndrome," describing it as a spectrum where founders can't let the business breathe, micromanage decisions, and constantly rework direction (including late-night idea pivots that exhaust teams). They discuss when it can be beneficial versus when it becomes harmful. Practical takeaways include recognizing the pattern, hiring and delegating appropriately, using a trusted sounding board, not dumping new ideas on the team, focusing on sales/user feedback, and accepting solopreneurship if control is non-negotiable.

Timestamps:

00:00 Audio Fails Cold Open

00:53 Meet the Hosts

01:11 Defining Founder Syndrome

04:16 Why This Topic Matters

05:54 When It Helps Visionaries

13:48 When It Turns Toxic

20:07 Industry Examples Creative Nonprofit

27:46 App Dev Pitfalls and Advice

32:20 Founders Fallacy Product First

33:22 Industry Expertise Debate

34:21 Desperation Built Businesses

36:49 Side Hustles Cut Teeth

37:49 Avoiding Founder Syndrome

43:07 Micromanage Or Delegate

49:54 Founder Syndrome Fixes

54:53 Hiring And Letting Go

01:03:22 Solopreneur Or Scale

01:05:39 Final Mantras Wrap Up

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 Episode 17 of the Founder Problems Podcast, Zachary Oshinbanjo, Sarah Schumacher, and Lee Zuvanich share one win, one struggle, and one thing they're working on. Wins include nonprofit and inbound lead progress, as well as consolidated consulting work. This episode emphasizes community, trust-based referrals and realistic pipelines.

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, Zach Oshinbanjo, and Lee Zuvanich unpack why founders are obsessed with productivity and the whiplash that hits after a break. They debate who benefits, discuss why it's important to define a personal vision of productivity, and emphasize the importance of prioritizing (non-side hustle) hobbies and rest.

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.

We might have stopped publishing, but we didn't stop recording.

The founders with problems have finally built up enough of a backlog to start releasing episodes again, so stay tuned. This is a short excerpt from our first recording in January 2026 where we talk about the vision for this podcast and why we're ditching in-depth editing.

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.