30 days. 5 cities: Boston, DC, Spokane, Nashville, and Orlando. My audit on a month of sales and internal travel: What I Hated: - Being away from my wife - Zero time to sit down for critical thinking - In-person meetings with zero next steps - Sleep deprivation - Feeling disorganized What I Liked: - Team dinners - Face-to-face time with customers - Being in the room with my executive leaders - Google chrome cast - Trying new coffee shops What Actually Made It Worth It (Loved): - Unscripted in-person discovery - Quarterly business reviews & project kick-offs - Multi-threading in real time - Verbal confirmations ($$$) - Pickleball with clients - Claude & Gemini working swimmingly well in the air

The discovery question that your sales manager hates, but I love: "What would help you sleep well at night?" Why it works: Buyers buy peace of mind. They want the confidence that the job will get done—without adding more aggravation to their plate or facing corporate punishment if it goes sideways.

Working with urgency internally is equally as important as working with urgency externally

Texts like this make me smile. Proud of my client for navigating procurement like a sales pro.

If I could undo one career mistake, it’s the years I wasted resenting high performers. Your peers aren't your competition; they're the blueprint and your best future network.

The worst LinkedIn outreach trend right now: "Hey {First Name}," [Blank space] People do this so the mobile preview hides the pitch and forces you to open it. Except everyone uses this trick now. When I see that blank space, I know it's spam and delete it immediately.

The bigger the price tag the bigger the problem

It's make-or-break time for Q4. The best enterprise reps know by week 3 of Q4 if a deal will close or not. Why? Q4 is effectively an 8-week selling window disguised as 13 weeks. Thanksgiving eats up a week, December is a ghost town after the 15th due to holiday PTO, and year-end budgets are all used up by now. Hosting a Deal War Room this Wednesday night. Bring one deal that you think is on the line and I will give you an idea or two to help close it. Free to join. DM if interested and I will share the link.

When a prospect demands uncapped liability on a <$100k deal, that's more than 10x the risk. Most AEs toss it to legal and pray. Wrong. The heavy lifting happens internally through your champion. Coach them to push back so both legal teams can meet in the middle How top reps handle it: 1. Coach your champion first Give them the exact argument to defend standard terms internally before procurement steps in 2. Bring the receipts Show that in 15+ years of enterprise deals, zero catastrophic claims have ever happened. 3. Attack the math Map the exposure directly to contract value 4. Get legal on the phone Bypass email tag and force a direct 1:1 conversation between both legal teams.

Spending thousands flying your team in just to read slide decks is malpractice. This week at our SKO, I ran a persona-led discovery Family Feud challenge. Teams drew a buyer—AP manager, energy director, CSO, treasury, procurement—and had to name the questions they’d actually ask. The top two went head-to-head in a CFO final. The results: - Real debate over the opening question - Live coaching in the moment - Zero glazed-over eyes Reps don't learn from listening. They learn from doing.

Discovery is hard if: • You’re trying to memorize a 20-question script • You can’t name the business outcomes your solution actually drives • You don't do any research on who you're speaking with • You show up empty-handed with zero point of view on their world • You’re desperate to book the demo instead of qualifying the problem • You don't have a case study to back up your conversation • You have zero clue how their industry actually operates

You build the playbooks. You fix their broken systems. You close seven figures of revenue. Then you leave. Access revoked. 0% equity. Zero retained assets. Your employer keeps the enterprise value. You get a polite thank-you and a direct deposit. Working for a company isn’t the mistake. Renting 100% of your intellect without building an asset of your own is. Look at @BrianLaManna. He's crushing quota at Gong—while publicly documenting the work, building a personal brand, and creating Closed Won. He drove massive revenue for his employer and created portable IP that compounds on his own balance sheet. Sell their product 9-to-5. Build your distribution and reputation 24/7. Never leave an organization with just a paycheck. Always own the assets or get left behind.