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A Smart Bear

Software business strategy, SaaS metrics, bootstrapping wisdom, and entrepreneurial frameworks from WP Engine founder on building profitable tech companies

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What is the value of one hour of a startup founder's time?
July 19th, 2026•longform.asmartbear.com
Lost confidence
June 21st, 2026•longform.asmartbear.com
Worrying is self-fulfilling; what to do instead
May 24th, 2026•longform.asmartbear.com
How to hire people who are better than you
April 19th, 2026•longform.asmartbear.com
Maybe not so much with the "optimization"
March 22nd, 2026•longform.asmartbear.com
Strategic choices: When both options are good
February 22nd, 2026•longform.asmartbear.com
A compass is not a map
January 25th, 2026•longform.asmartbear.com
Creating space
January 4th, 2026•longform.asmartbear.com
Scaling by "delegation" isn't good enough
December 7th, 2025•longform.asmartbear.com
Mission, Vision, poTAYto, poTAHto
November 9th, 2025•longform.asmartbear.com
When being an "expert" is harmful
September 28th, 2025•longform.asmartbear.com
Your target market isn't demographic
September 7th, 2025•longform.asmartbear.com
Yes, but who said they'd actually BUY the damn thing?
August 17th, 2025•longform.asmartbear.com
Max MRR: Your growth ceiling
July 27th, 2025•longform.asmartbear.com
Specificity: A weapon of mass effectiveness
July 13th, 2025•longform.asmartbear.com
Ruthless prioritization while the dog pees on the floor
June 22nd, 2025•longform.asmartbear.com
Bootstrapped CPC rule of thumb: ARPU/25
June 8th, 2025•longform.asmartbear.com
More or less
June 1st, 2025•longform.asmartbear.com
Rude Q&A: The constructive devil's advocate
May 25th, 2025•longform.asmartbear.com
When customers buy your competitor's product… and then buy yours
May 18th, 2025•longform.asmartbear.com