Former CEO of The Hustle and Hampton. Founder coach, advisor, and creator of Hiring OS.
Nov 12, 2026
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4 min read
This week: budgeting for the misses, four execs on planning, Khosla’s if/then playbook, and a book that became an office joke
Nov 5, 2026
5 min read
This week: the piece of annual planning almost every founder skips, a gut check for your 2027 plan, an 80-minute strategy masterclass, and the business bios I’d read before your offsite
Oct 29, 2026
This week: why most SDR agencies flop, Paul Graham’s best question, an AI mind virus, and dueling weathermen
Oct 22, 2026
7 min read
This week: what senior leaders really cost, Buffett’s unusual software bet, who’s winning consumer AI, and skating vs. walking
Oct 15, 2026
This week: the real reasons companies cut, how to rebuild paid ads fast, “hard to do” vs. “hard to get,” and the merch nobody can buy
Oct 8, 2026
This week: the one trait to hire for in the AI era, the right way to talk to customers, Ackman's hospital-room story, and a true-crime page-turner
Oct 1, 2026
This week: what replaces you when you can't be in every meeting, why buyers balk at AI pricing, staying close to the work, and Jensen Huang on AI alarmism
Sep 29, 2026
11 min read
Direction, visibility, accountability, and cadence: the four systems that take over once the company outgrows you.
Sep 24, 2026
This week: the exec-room ritual GM and Meta are missing, what AI can't do in a sales call, and the line about success you'll want to steal
Sep 17, 2026
This week: the three things a bot still can't fake, a 30-minute Zuck profile, and a rule for when to trust AI
Sep 10, 2026
This week: what actually killed Nike, touching grass for brand ideas, one rep's entire bot setup, and how PMF slips away
Sep 3, 2026
This week: the entry-level job is collapsing and why that's your hiring edge, a 20-deal sales gut-check, the great consumer trade-down, and how Ozempic is shrinking the grocery bill
Aug 27, 2026
This week: why the format of your team updates matters more than you think, Lovable's design playbook, Hiten Shah on taste, and LinkedIn's slop button
Aug 20, 2026
This week: how CEOs actually build urgency, Obama's summer list, Buffett's integrity filter, and the job you weren't supposed to take
Aug 13, 2026
This week: what Airtable's fire sale actually means for profitable founders, the internet running out of training data, the hire who hunts pain, and how to price in the AI age.
Aug 6, 2026
This week: the gap between AI knowing you and AI recommending you, the death of the follower, and the WFH data is finally in.
Business
Aug 4, 2026
6 min read
A coach for profitable, founder-owned companies, not venture-backed startups burning toward a Series B.
Aug 3, 2026
8 min read
Most founders reach for a COO to escape operational chaos. That's the wrong reason. When to hire a COO, what it costs, and the ladder to climb first.
Salespeople are professionally good at interviews. That's the trap. The founder's system for hiring a salesperson who can actually sell. Free frameworks.
How to hire employees for a small business when referrals keep failing you: sourcing, the 3-minute video filter, work samples, and scorecards. Free system.
The complete sequence for hiring your first employee: role definition, legal setup, interviews, and offer. No recruiter, no HR department, no guesswork.
Jul 30, 2026
This week: the one habit that fixes accountability, the AI labor piece everyone's talking about, and what USA Hockey can teach you about hiring.
Jul 29, 2026
The 9 common hiring mistakes founders repeat, and the process fix for each. From 20+ years of hiring at Motley Fool, The Hustle, HubSpot, and Hampton. Free system inside.
Jul 23, 2026
This week: the soft close, stop prompting and start looping, how companies quietly lose PMF, and never adding a dud book again.
Jul 16, 2026
This week: the three signals that separate a real finisher from a great talker, plus I'm officially opening up hiring help for your next senior leader.
