Back in 2024, I was driving home from Wilmington to Virginia, flipping through podcasts, bored stiff. I landed on Mel Robbins.

She was talking about her husband and how he'd reinvented himself in semi-retirement by starting a retreat out in California.

Flying guys in, spending a few days together, working through problems around a campfire.

Then it clicked: I already had the three ingredients that most people spend years trying to assemble:

1) A venue I controlled (Saltwater Resort + event space)

2) A repeatable set of founder problems I’d already solved dozens of times (systems, delegation, pricing, fundraising, exit timing)

3) Real credibility from having done it myself (2 exits + 50+ investments)

I had portfolio companies I was already advising on the phone, one founder at a time, walking them through the same problems over and over.

What if I could compress 6 months of 1:1 calls into a 72-hour offsite?

I had the venue. I had the content. I had the case studies.

I just hadn't put it together yet.

On paper, everything was fine as-is.

I was investing, staying close to founders, and doing work I enjoy through my VC shop Cape Fear Ventures

Still, I kept coming back to the same thought: what if I could help in a more concentrated way than one call at a time?

After you sell companies and shift into the advisory side, you start noticing that virtually every founder you talk to is stuck on the same handful of problems.

Pricing. Capital strategy. How to raise and from whom. Distribution and marketing that doesn't depend on the founder's personal network. How to talk about the product in a way that sells without them in the room. Hiring and setting the culture.

These problems show up at $200K and they're still there at $3M.

The details change, of course, but the categories don't.

I started building the curriculum from my own experience — two software companies built and sold, one real estate business turned around, executive education at Harvard, and pattern recognition from investing in 50-plus early-stage companies.

After three cohorts it’s now expanded to a 2.5-day program with two full days of sessions, evening activities, guest speakers, and a keynote send-off.

I capped the cohort at 10 founders because I wanted the room small enough that nobody could hide during the hot seat reviews, but also so everyone got real 1:1 time and the room stayed intimate enough for real connections to form.

The Format

The hot seat reviews are where it starts.

Each founder gets 15 minutes and diagnostic questions designed to expose the real constraints:

• What keeps slipping to next month?
  
• Where overdelivery is draining margins?
  
• Which processes have never been written down?
  
• What would collapse if the founder went offline for two weeks?

From there, the curriculum moves through operator bottlenecks and delegation frameworks, financial systems and capital strategy, customer discovery and development, team culture, and a 90-day execution plan.

Every session pulls from real case studies — portfolio companies and investments where I watched a specific decision play out.

Many are situations I was involved in, where I can tell you exactly what went wrong and exactly what worked.

What Three Cohorts Taught Me

Cohort 1 was proof of concept.

Could I actually hold a room for two and a half days and deliver something founders couldn't get from a generic conference?

The answer came back 5 out of 5 across the board.

But what caught me off guard was the emotion.

Founders showed up thinking it was about content. What they walked away with was closer to an identity shift.

Cohort 2 was refinement. Tighter curriculum, better pacing, sharper diagnostic questions.

Cohort 3 proved something I'd suspected but couldn't confirm. We had companies ranging from pre-revenue to $3M ARR, and the curriculum worked for every one of them.

The constraint was the same at every stage: the founder built the business, and now the founder was the thing preventing it from growing.

Every cohort we bring in operators who've led under real pressure:

• Exited founder Chris Hornbecker
• Retired three-star general Joe Anderson
• Former Navy SEAL turned tech leader Andrew Sridhar.

All shared powerful stories and frameworks that map directly to what founders face every week.

We also started bringing alumni back.

Founders from Cohort 1 returned for updated sessions on macro trends, AI developments, financial strategy. They got new material. New founders got peer validation from people who'd already made the transition from Founder to CEO.

A curious part I didn't plan for: the unstructured time matters as much as the sessions.

Beers at sunset in Surf City. Dinner on the water at Wrightsville Beach. Founders talking shop without an agenda, comparing notes on AI tools and hiring mistakes and cash flow problems they're too buried to think about during a normal week.

Getting founders physically away from their business triggers a different kind of thinking.

They stop reacting and start seeing the God’s-Eye View.

And it's amazing what comes up once you have that distance between you, your inbox, and the same problems you're looping on autopilot.

The Retreat Is Becoming a System

That's how you build anything that lasts. You don't declare it finished. You pressure-test it, listen, and make it better.

We document what works, cut what doesn't, and improve the program after every cohort, which is exactly what we teach founders to build inside their own companies.

There's something about putting people in a room together, with founders at different stages, facing the same constraints, learning from each other's problems, that a phone call can't replicate.

I started this because a podcast gave me an idea on a long drive home.

Three cohorts later, it's become the thing I wish I'd had when I was building my first company at 25 with no playbook, no systems, and nobody to call.

Cohort #4 is forming for June 1-4.

Same structure: 2.5 days at Saltwater Resort in Surf City, North Carolina.

Early June is when the island hits its stride — warm water, long evenings, uncrowded beaches before the peak tourist season rolls in.

Between sessions, founders are on jet skis, eating dinner looking out on the water, watching the sunset with a beer in hand.

The setting is one of the most powerful aspects of the retreat. When your phone stops buzzing and you're staring at the horizon instead of a screen, the problems you've been too close to suddenly become obvious.

Three days here does something a weekend offsite in a Marriott conference hall never will.

If you’re an early-stage founder who’s maxed out and hit a plateau - you can find more details about Elevate here- or shoot me a reply to this email.

Speak soon,

Richard