Latest Episode.
Episode 21: What’s Your Problem: Writing Grants, Wrangling Kids, and the Case for Boring B2B
In this episode we talk side apps, a manga review system, and an awarded grant. Plus: digital calendars, consulting-to-product startup paths, and "boring” B2B.
Listen + Show Notes Past Episodes
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.
Episode 20: How to Run a Business Without Killing Yourself
What’s actually kept the workaholic cohosts healthy(ish): consistent workouts, bullet journaling, and sleep. Plus: what hasn’t worked and practical advice.
Listen + Show Notes Episode 19: What’s Your Problem: Back-to-School Wins, AI Cheapskates, and Key-Man Chaos
In this episode, wins center on kids being back in school; struggles include client flakiness/boundaries, AI making “cheapskates free to be cheapskates,” and more.
Listen + Show Notes Episode 18: Runaway Founder Syndrome
In this episode we discuss “runaway founder syndrome” as a spectrum, when it can be beneficial versus when it becomes harmful, and how to recognize the pattern.
Listen + Show Notes Episode 17: What’s Your Problem?
In Episode 17 we discuss wins, struggles and what we're working on, including: community, trust-based referrals and realistic pipelines.
Listen + Show Notes Episode 16: Productivity Whiplash
We're back, and in this episode we unpack why founders are obsessed with productivity and the whiplash that hits after a break.
Listen + Show Notes Season 3 Update
We might have stopped publishing, but we didn't stop recording. The founders with problems have finally built up a backlog to start releasing episodes again!
Listen + Show Notes Episode 15: What’s Your Problem: Insurance Annoyances, Project Management and Creating Fearless Content
In this episode we forget the intro, discuss insurance, project management, delegation, content creation and pushing past perfection. Plus one of our own fails.
Listen + Show Notes Episode 14: Let’s Talk Rebranding
We dive into the art and chaos of rebranding. How do you know it’s time, what about trademarks, how much should you spend? Listen in for actionable takeaways.
Listen + Show Notes Episode 13: From Rough Patches to Reality: When to Call It Quits on Your Startup
We discuss the challenging decision of whether to shut down a business, Zach shares a recent realization, and we reflect on personal startup experiences.
Listen + Show Notes Episode 12: What’s Your Problem: Real Talk on Operations, Focus, and Embracing Limitations
A new format about our recent founder problems: tedious admin work, the art of saying no, and staying afloat when the world pulls you in twenty directions.
Listen + Show Notes Episode 11: All That AI BS: An Infodump of Facts, Fears and Futuristic Predictions
In this episode we dive into the contentious world of AI, exploring its potential harms (DOOM!) and benefits (being lazy!) as well as how we use it.
Listen + Show Notes EP10: Don’t Quit Your Day Job… Yet
Quit your secure 9-to-5? We examine the pros and cons while totally unable to hide our bias toward entrepreneurship (but do it strategically, please).
Listen + Show Notes EP9: Freelancing: A Minimum Viable Business
In Episode 9, we navigate the murky waters of freelancers vs. entrepreneurs with a detour into personal branding, personal goals, and leveraging personality types.
Listen + Show Notes EP8: Finding Silver Linings: What Doesn’t Kill You Makes You Better at Business (and Public Speaking)
From last-minute grant scrambles to public speaking tips, we dive into personal stories and practical advice on finding the silver lining in every situation.
Listen + Show Notes EP7: Rented vs Owned: The Digital Real Estate Dilemma for Founders
In this episode we discuss rented versus owned digital Internet platforms, because social media accounts are great until they pull the rug out from under you.
Listen + Show Notes EP6: When the Market Says ‘Nice Try, Buddy:’ Finding Product Market Fit
In this episode, we talk about understanding your Total Addressable Market (TAM) and listening to feedback before assuming your next idea is the big one.
Listen + Show Notes EP5: Vetting Cofounders: Why Swiping Right Isn’t Enough
We stress the importance of thorough due diligence for cofounders, with practical tips like working together on a trial basis and ensuring aligned values.
Listen + Show Notes EP4: The Focus Myth: Navigating Multiple Side Hustles, Experimentation and Exploring Interests
In this episode we discuss managing multiple ventures by utilizing systems/natural nerd skills. Plus, advice to our younger selves about choosing a career path.
Listen + Show Notes EP3: When to Quit: Feast or Famine Cycles, Slow Intuition, and Listening to the Market
In this episode, we discuss our experiences with the mental gymnastics behind tough decisions. How do you know when to push through and when to throw in the towel?
Listen + Show Notes EP2: Three Approaches to Annual Planning: Tarot Cards, B.L.U.F.F., and the Pen-to-Spreadsheet Pipeline
We tackle the once in a year task of planning the next one. From Pinterest-level vision boards to X-men analogies, we cover 3 wildly different planning styles.
Listen + Show Notes