Ep. 3 - What Sucks About Owning A Business And Listener Submitted Questions

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In this candid Unsexy Businessmen episode, Alex and Aaron strip away the highlight-reel and talk through the real grind of entrepreneurship—finding those first customers, living with uncertainty for months, managing employees (and your own standards), drawing boundaries with clients, and carrying stress on “vacation.” They share early-stage timelines that actually happen, why some clients cost more than they pay, when to fire nicely, and how to hold people accountable without poisoning your culture. Plus: listener questions on “free work” from a big client and handling a distracting employee—complete with scripts, guardrails, and documentation tips you can use today. And Business Advice!

What you’ll learn

• Why the first 6–12 months feel terrible—and how to push through it

• A simple rule for saying “no” to scope creep (without nuking the relationship)

• The “asshole tax,” when to cut clients, and how to do it professionally

• One-on-one frameworks for performance issues (and why to keep names out of it)

• Cash discipline 101: don’t buy the boat—build the buffer

• The mindset shift that makes your second (and third) business less scary

If you’re stuck at the start, drowning in “small tweaks,” or worried about being “too harsh,” this episode gives you the playbook—and a shove—to keep going.

 

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