Ryan DeissCo-Founder & CEO, The Scalable Company

5 CEO Mistakes That (almost) Cost Me Everything #entrepreneur #failure #startup

8 Jul 2026 · 1 min

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1:06

In this solo video, seasoned entrepreneur Ryan Deiss reflects on over 20 years of running businesses, during which he lost everything twice. He distills those painful experiences into five concrete lessons he would give his younger self if he could travel back to his first day as CEO. The lessons cover: (1) building manual, customer‑journey‑aligned scorecards instead of relying on vanity or automated metrics; (2) setting a clear three‑year target and breaking execution into 90‑day sprints rather than vague annual plans; (3) hiring functional leaders who own outcomes instead of “helpers” who merely add busywork; (4) fixing profit margins and cash flow before chasing top‑line revenue growth; and (5) recognizing that a packed calendar does not equal productivity, emphasizing focus over busyness. The video is a candid, instructional narrative aimed at founders and startup leaders seeking to avoid costly strategic missteps.

Chapters

I've run businesses long enough to have owned an office fax machine, and in that 20+ years, I've lost everything not once, uh, but twice. And I picked up some pretty good lessons along the way. So if a time machine dropped me back into my very first day as CEO, here are 5 things that I would do differently. One, I'd build manual scorecards that mirrored and tracked the customer journey. Chasing vanity metrics has cost me a small fortune, and automated scorecards, they just want to gimme false data. Number 2, I'd set a 3-year target and I would execute it in 90-day sprints or chunks. Annual planning is just New Year's resolutions for business owners. Number 3, I'd stop hiring helpers and I'd start hiring functional leaders who can actually own the outcomes. Helpers make you busier, leaders make you wealthier. Number 4, I'd fix my margins before I chased revenue growth. P&Ls lie, cash doesn't, and you need the cash if you wanna grow. Number 5, I'd stop confusing a full calendar with a productive day. Busy Is not a strategy, and busy does not equal productive.