Founder Problems Podcast

Founder Problems Podcast
Podcast Description
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.
Podcast Insights
Content Themes
The podcast explores various themes related to the entrepreneurship journey, including personal struggles with mental health, decision-making processes for quitting, and different annual planning methods. Episodes feature discussions like those on knowing when to quit based on business cycles, balancing mental health alongside professional demands, and unique approaches to annual planning such as tarot cards and operational methods.

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.
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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