Founder bottlenecks, pricing drift, weak decks? Let’s fix it on Sept 8–11:

3 days to upgrade how you operate, hire, and raise.

If you’re a founder under $3M ARR (or know one who needs to level up) this is for you.

Hey there,

After overwhelmingly positive feedback from my first Elevate CEO Retreat I'm running Cohort #2 in September.

It's a 2.5-day working reset for tech founders and CEOs doing real revenue (typically between $250k and up to $3M ARR) and ready to break through their next ceiling.

It’s where you bring the real shape of your business, open the hood, and upgrade the systems holding you back.

When and Where:

September 8–11, 2025

Saltwater Resort, Surf City, Topsail Island, North Carolina

$1,500: includes accommodation, breakfasts and lunches, welcome drinks, and team event and party.

We cap the room at 10 seats.

Every founder gets deep time on their business.

You won’t get lost in the crowd, and you won’t leave with a generic to-do list.

Apply Here

Who It’s For

This is for the operator who’s outgrown default mode.

You’ve built something real. You’re solving real problems.

You might be hiring, raising, or scaling fast, or just trying to keep pace with what you’ve already built.

But behind the scenes:

You’re still in too many loops. Too much still depends on your energy. And even your team’s running, they're not always in sync.

This retreat is designed for that inflection point.

What We Cover

Day 0 - September 8: Arrival & Orientation

You’ll arrive Monday afternoon, check in to Saltwater Resort, and meet the other cohort members over drinks.

Day 1 - September 9: Foundation & Strategic Clarity

We start by X-raying your business in public.

Every founder gets 20 minutes of live company review.

We'll pinpoint where your model is fragile, your story is fuzzy, or your systems are brittle.

Then we sharpen strategy.

You’ll work through foundational frameworks upgraded for 2025:

Porter’s Five Forces, Core Competency Theory, Blue Ocean Strategy, and apply them directly to your business.

You’ll stop defaulting to hustle and start thinking structurally about growth.

You’ll map your value creation vs. value capture, reassess revenue models, and set a more durable advantage.

It’s “What business are you actually in?” and “What would make this scaleable without you?”

We close the day by addressing the founder bottleneck head-on:

What do you still own that’s slowing the company down?

What systems must replace you?

You’ll build your “Discipline OS".

The operating structure that gets you out of reactive loops and into repeatable leverage.

Then we take it to the water for a team-building event.

You’ll end the day knowing every founder in the room and where they’re strongest.

Day 2 - September 10: Growth, Capital, and Execution

This is where we go deeper into the machine.

We cover the hard operational trenches:

Finance & Capital Strategy

You’ll rebuild your financial backbone: budgeting, cash discipline, forecasting, burn vs. investment logic.
We’ll walk through what great finance systems look like before you hire a CFO.
You’ll also tackle your capital strategy, whether that means equity, grants, venture debt, or bootstrapping with discipline.

Fundraising Readiness

We’ll stress-test your investor posture. If you’re planning to raise in the next 12–18 months, we’ll help you frame your milestone logic, fix weak metrics, sharpen your deck, and run a raise like a process—not a hope.

Team & Culture

You’ll map your leadership team, diagnose organizational debt, and define what “culture as a system” actually means for a business your size. We'll clarify roles, close accountability gaps, and prevent breakdowns at scale.

Marketing & Customer Strategy

We’ll review positioning, channel strategy, and your messaging map. You’ll get sharper on how to communicate value, differentiate in-market, and build brand equity with speed and simplicity.

Family Business & Succession

If you run a family-led company, we’ve built a track that helps navigate legacy, governance, next-gen transitions, and communication inside complex systems.

We close the night with a private team dinner and celebration.

Day 3 - September 11:Leadership & Legacy

Our final day is about zooming out.

You’ll work through leadership traps, strategic posture, and founder blind spots. You’ll leave with a concrete 90-day execution plan, and the habits, metrics, and rhythms to sustain it.

Then we wrap with a talk from Ret. Lt. Gen. Joe Anderson (US Army): on endurance, command, and building high-performance teams under pressure.