The Retreat That Transforms Overwhelmed Founders Into Systematic CEOs

Join 10 Founders to Install the CEO Operating System That Scales Without You
Apply for Jan 26-29

The Problem

You've Become the Lid on Your Own Pot

You built something real. Customers who love you. Revenue that would make your 2019 self proud. By every LinkedIn metric, you’re “crushing it.”

But let’s be honest about what “crushing it” actually looks like.

The $500 Bottleneck

You're the CEO who still approves the $500 software purchase because the policy you wrote 2 years ago says anything over $250 needs your sign-off. You're still the bottleneck for decisions your intern could make.

The Endless Edits

Your Head of Marketing sends you copy to review "just real quick." 14 edits later, you wonder why you hired her. But deep down you know that you've trained everyone to run things by you first.

The Dependency Creator

You've made them dependent. These "quick questions" are never quick. Your team has learned to rely on you for every decision, creating a system where nothing moves without your input.

The Founder Closer

Your sales team can close deals, but prospects always want to "hear from the founder." So you jump on calls you shouldn't be on, selling deals your team should close, because saying no feels like leaving money on the table.

The Real Cost

Except you ARE leaving money on the table — all the deals you're not pursuing because you're too busy closing the ones in front of you. Every call you take is an opportunity you're missing.

The Context-Switch Master

The worst part is that you've become good at it. You can context-switch between seven different problems in an hour. You've memorized every system, every customer quirk, every team member's weakness.

The Solution

Your 2.5-Day Transformation

Over 2.5 intensive days, you’ll systematically dismantle the founder habits holding you hostage and install the CEO systems that create compound growth.

Strategic Clarity

Build purpose beyond revenue, pricing anchored to value, and positioning that makes competition irrelevant.

Scale Systems

Design operations that compound without headcount and create metrics that actually drive decisions.

Leadership Architecture

Map leadership gaps, define culture as system, and close accountability holes that leak momentum.

Financial Discipline

Build your CFO-level financial backbone and transform fuzzy stories into systematic proof.

Your Complete CEO Toolkit:
Personal Bottleneck Audit that maps your top 5 time traps
Decision Framework Templates your team runs without you
Weekly CEO Customized Scorecard tracking only metrics that matter
Fundraising Narrative Worksheet that's helped raise multiple 8-figures
Team Meeting Rhythm Playbooks that protect 10+ hours weekly
Direct access to me when you hit critical decisions
90-day Leadership Blueprint

Who is this for?

You're our ideal founder if...

  • You've built real revenue ($250K-$3M ARR)
  • You work 60-80+ hour weeks but have hit a plateau
  • You employ 3-20 people who look to you for every decision
  • You know you're the bottleneck but can't figure out how to extract yourself
  • You're ready to kill the habits that got you here and upgrade into The CEO Who Executes

Save your money if...

  • You're pre-revenue or idea stage
  • You're a lifestyle business owner happy at your current size
  • You're looking for "hacks" instead of fundamental transformation
  • You believe "no one can do it like me" and won't let go of control
  • You want theory and inspiration without the messy work of change

Your 2.5-Day Transformation in Photos​

Your business should work without you. Founder dependency is a liability, not a badge of honor.
David Reeser
The energy in the room was unmatched...every moment was packed with growth, insight and action.
Jennifer Namvar
Surround yourself with motivated like-minded CEOs to bounce ideas off and help with the loneliness of business ownership.
Mark Huff

Your Transformation Timeline​

Day 0
Arrival & Group Reception

Check into Saltwater Resort. Evening drinks overlooking the Atlantic with nine other founders who get it. No pretense. No posturing. Just truth.

Day 1
Foundation & Strategic Clarity
The journey begins here. This opening session is designed to help you unwind, connect, and align before diving into three days of transformation. You’ll meet the Elevate team, your fellow founders, and the support staff who will guide your experience throughout the retreat. Together, we’ll review the agenda, set expectations, and define what success looks like for you this week, both personally and professionally.
Every founder gets 20 minutes in the hot seat. We dissect your business model, identify your top 3 bottlenecks, and pinpoint exactly where you're still playing founder instead of CEO. This isn't comfortable, but it's necessary. We’ll zero-in on precisely what to fix.
Founders leave this session with strategic clarity that transforms how they lead, sell, and scale. You’ll know exactly who you serve, why you win, and how to price your value with confidence. Your business will stand on a foundation of data, differentiation, and discipline — ready to attract capital and deliver consistent results.
Founders leave this session with a clear picture of how to operate on the business, not in it. You’ll have identified your biggest bottleneck, mapped your execution rhythm, and built the first version of your Discipline Engine — the system that replaces heroics with habit.
Some of the best insights happen between sessions. Create bonds and breakthroughs you can't get in a conference room.
Day 2
Growth, Capital & Execution
Founders leave this session seeing the big picture through the lens of capital, discipline, and disruption. They’ll understand how macro trends connect directly to micro decisions: hiring, pricing, capital deployment, and investor communication.
Founders leave this session with the mindset and tools to fund like CEOs — disciplined, data-driven, and investor-ready. They’ll know how to speak the language of capital, build proof before pitch, and design a financial system that earns trust long before they ask for it.
Founders leave this session seeing marketing as a system of alignment, not a megaphone. They’ll know how to communicate with precision, build customer trust early, and translate insight into predictable traction.
Founders leave this session with a practical framework for turning culture into a system, one that scales with clarity, consistency, and purpose. They’ll understand how to balance family and business roles with structure, and how to ensure the organization’s values endure long after their direct involvement.
The Elevation Dinner is your moment to pause, reflect, and celebrate the breakthroughs, friendships, and growth forged over the past few days. Surrounded by fellow founders, investors, and the Elevate team, this evening is about honoring the work you’ve done and the momentum you’ve created. This isn’t just a closing dinner, it’s the symbolic start of your next chapter. Over great food and coastal conversation, you’ll share lessons, laughter, and future plans with the people who now make up your founder circle.
Day 3
Leadership & Legacy
Pull it all together into your personal 90-day transformation plan. Lock in weekly scorecards, monthly strategic blocks, and quarterly planning rhythms. Build accountability that ensures implementation.
Learn endurance, command, and high-performance teams from someone who led thousands in life-or-death situations. Understand what real leadership looks like when stakes are highest.
You leave with frameworks, systems, and nine peers who'll call you on your founder backsliding. More importantly, you leave as an upgraded version of the founder who walked through the door. This is identity reconstruction with immediate implementation.

The Elevate CEO Experience​

Elevate happens at The Saltwater Resort: a clean, coastal space designed for focus.

Ocean views, fresh salt air, and scenic beach horizons are ideal conditions for your first uninterrupted thought in months.

You’ll have a private room to recharge, a quiet space to work, and shared access to:

  • A saltwater pool
  • Bike / Shibumi rentals for local exploration
  • Covered outdoor common area with seating, games, and ping pong
Plus, it’s just a short walk from downtown Surf City’s best restaurants.

Your $1,500 investment gets you private lodging, expert-led CEO training, and a lifelong network of peers, all built to unlock ROI far beyond the retreat.

For more information on Saltwater Resort, please visit their website https://www.saltwatertopsail.com/

Elevate CEO Teaching Team​

Richard Stroupe

Managing Partner, Cape Fear Ventures
Lead Instructor, Elevate CEO Retreat

Richard Stroupe is a serial entrepreneur, seasoned investor, and leading technologist with a proven track record of turning innovative ideas into thriving, scalable companies.  Over the past two decades, he has founded, built, and successfully exited multiple ventures across technology, defense, and real estate, each time honing the operational discipline, strategic insight, and leadership skills that now define his approach to business.  Driven by a mission to empower the next generation of groundbreaking startups, Richard provides hands-on mentorship to founders, guiding them through the complex and often unpredictable challenges of early-stage growth. 

As Founder and Managing Partner of Cape Fear Ventures, Richard invests in and builds high-potential businesses that combine operational excellence with strategic growth.  Under his leadership, the firm has become known for its ability to identify promising ventures early, provide deep operational support, and position companies for long-term value creation.

Beyond his role as an investor, Richard is deeply committed to leadership development and entrepreneurial education. He has served as a Part-Time Faculty Member at George Washington University and as an Entrepreneur-in-Residence at Georgetown University, where he mentored students, alumni, and emerging founders on how to scale ventures and lead with purpose.  Richard is also the creator of the Elevate CEO Retreat, a transformational program for growth-stage founders, and host of The Amplified CEO Podcast, where he shares actionable insights from top leaders and operators. 

Rita Suggs

Elevate CEO Program Manager

Rita is the Program Manager at Cape Fear Ventures, where she leads strategic initiatives and delivers founder-focused programs designed to help early-stage entrepreneurs turn promising ideas into scalable businesses.  Known for her attention to detail and ability to coordinate complex logistics, she oversees every aspect of program delivery, from venue selection and design to working with facilitators who enrich the Elevate experience for participants.  By collaborating with industry experts and startup coaches, Rita ensures founders gain the tools, strategies, and leadership skills needed to overcome challenges, accelerate growth, and achieve meaningful results.  Partnering closely with service providers, she integrates resources to create programs that are impactful, memorable, and tailored to the unique needs of each cohort.

In addition to her work in venture, Rita is an accomplished real estate professional and a native of coastal North Carolina.  With an MBA in Real Estate Development, she is recognized for her credibility, commitment, and results-driven approach. Balancing both fields, she brings a distinctive perspective that combines strategic thinking, operational excellence, and a deep understanding of people and place, guiding both clients and founders toward long-term success.

Course Schedule

The curriculum is delivered in an intensive, three-day in-person experience designed to spark rapid breakthroughs and drive lasting change. Through a dynamic mix of immersive workshops, strategic peer collaboration, and guided implementation sessions, you’ll gain the tools, frameworks, and confidence to transform the way you lead. Each day builds intentionally on the last, ensuring you leave with not just powerful insights but a clear, actionable roadmap you can immediately apply to accelerate your business.
Date
Fee
Format
Status
Jan 26 – 29, 2026
In Person
$2,000

Accepting Applications

Mar 23 – 26, 2026

In Person

$2,000

Accepting Applications

May 11 – 14, 2026

In Person

$2,000

Accepting Applications

Ready to Transform?​

Application takes 2 minutes. Acceptance within 24 hours.