Want to go deeper? Join me next Thursday, October 29 at 9 AM Pacific for Annual Planning That Drives Execution. Apply to join: us02web.zoom.us/meeting/regi… All Techstars founders, mentors and partners are welcome!

Join founders and leadership teams from our venture partner network next Thursday for Annual Planning That Drives Execution. Annual planning should create more than a plan. Join me next Thursday, Oct. 29 at 9 AM Pacific for Annual Planning That Drives Execution: a practical workshop on turning priorities into coordinated action. Register: us02web.zoom.us/meeting/regi…

Companies are quick to calculate the cost of unused capacity. They’re much slower to calculate the cost of having none. When everyone is booked solid, the smallest surprise becomes an organizational delay. Efficiency without adaptability is expensive.

The expensive board surprise isn't missing a number. It's discovering that people inside the company saw the warning signs weeks earlier, but nothing changed. The real failure wasn't reporting. It was the organization's inability to turn intelligence into action.

Execution drift doesn’t always come from a lack of effort or accountability. It happens when decisions are delayed, priorities compete, and teams move independently. Great teams don’t just make plans. They build the ability to make decisions and execute together.

Called it?

Does anyone know a company that does cold outreach and generates leads for other businesses? For the life of me, I can’t seem to find one. 🫠

Big congratulations to Greg Castle @gpcastle12 and the Anorak Ventures @AnorakVentures team on Fund III. I’ve appreciated having Greg as part of the collective and finding opportunities for our work to intersect. This clip from Tech Scenes captures how he thinks about investing upstream in the technologies and infrastructure everything else depends on. Excited to see what Anorak backs next. 🚀

So many teams raising capital, are they execution ready?

Financial planning is not organizational planning. Finance tells you what the business needs to produce. Organizational planning determines how the organization will actually produce it. The best plans iterate between the two until priorities, resources, assumptions and numbers become one cohesive plan.

Execution is everything.

Skipping your QBR is an expensive way to save a few hours. Before committing another 90 days of time, talent and capital, ask: What worked? What didn’t? What changed? What will we do differently? Strong teams learn, adapt, plan and act together. That’s how you reduce Execution Drift.

Just out here de-risking portfolios.

AI agents will expose fuzzy decision rights faster than any org chart. Humans can compensate with judgment and relationships. Agents need explicit context: what they can see, change, decide, and escalate. AI won’t fix organizational ambiguity. It will make it visible.

If every problem still needs the CEO to decide what happens next, you don’t have distributed ownership. You have distributed observation and centralized execution. That can work for a while. Then complexity wins.

There is a path forward. The CEO Bottleneck: How to delegate without losing visibility. medium.com/@LeadbyChange/the…

You want a high-performing team. But have you actually decided to become one? Annual planning is a natural moment to make that choice. Not just what you’ll achieve. How you’ll operate together to achieve it. High performance starts with intention. Then you build the rhythm.

Looking forward to the session. ✨