Freeing Founders Feeling Their Growth Plateau

The Business Grew Because of You. Now It’s Time for It to Grow Beyond You.

The spark is fading, you’re stuck operating in the weeds, and unclear on the next move.

I help $1M+ business owners elevate their role beyond their current limitations.

helped CEO’s hire outside help, decide to step away, co-founder break

All of it is waiting on one thing… You.

Freeing Founders Feeling Their Growth Plateau

The Business Grew Because of You. Now It’s Time for It to Grow Beyond You.

The spark is fading, you’re stuck operating in the weeds, and unclear on the next move.

I help $1M+ business owners elevate their role beyond their current limitations.

helped CEO’s hire outside help, decide to step away, co-founder break

All of it is waiting on one thing… You.

The Invisible Problem Most Founders Face: Your Success becomes the trap

What once energized you now exhausts you. The role that worked at $1M doesn’t work at $10M, but no one teaches you how to evolve into a new one. The business still runs on your energy, time, and decisions… right as your energy and enthusiasm start to dip and your best ideas are buried under busywork.

Growth has stalled, not because the market has changed, but because you haven’t changed.

  1. The Spark Is Gone.
    You’re no longer energized by your business. The passion that once fueled you feels distant.

  2. Trapped in the Weeds.
    Your calendar is full, but your best ideas are on hold. Day-to-day operations eat your time and focus.

  3. Unclear on the Next Move.
    You’re stuck between options—grow, sell, hire leadership, start over—but none feel right. Decision fatigue sets in.

The Truth About Growth

Your company can’t scale if you stay at the center. The bottleneck isn’t the business, it’s the way you align and act within it.

This is the phase where many founders…

  • Lose their spark.

  • Avoid the next big decisions.

  • Fantasize about burning it all down or starting something new… just to feel alive again.

But you don’t need to start over. You need a new way to lead.

The Shift That’s Required: Stop grinding. Start re-aligning.

Stepping into the right role, the one that aligns your genius with what the business actually needs.

When the founder evolves, the company unlocks:

  • Team alignment.

  • New growth paths.

  • Space for innovation.

  • Freedom to think again.

You've Built a Successful Business…But Now You're Afraid You Might be The Bottleneck. To grow your business, you need to look beyond your business.

The Spark Is Gone.
You’re no longer energized by your business. The passion that once fueled you feels distant.

  1. Trapped in the Weeds.
    Your calendar is full, but your best ideas are on hold. Day-to-day operations eat your time and focus.

  2. Unclear on the Next Move.
    You’re stuck between options—grow, sell, hire leadership, start over—but none feel right. Decision fatigue sets in.

My business doubled without me… is that possible?

Tell me if this sounds familiar...

You're secretly planning your next venture but can't find the courage to share it with your team. You're hiring people half-heartedly, hoping they'll fill gaps you can't even define. Big decisions keep getting pushed down the road. You sense you're creating more chaos than clarity when you step in to act.

When you tried to share your vision, your team couldn't follow…ouch, that felt personal...

You're losing the spark, avoiding conversations about your business, and feeling increasingly disconnected from your founder story.

What if this is a ceiling you can’t break through? Team interactions have shifted from inspiring to stressful. You're tolerating team members you no longer believe in. You've tried cold plunges, saunas, and diet tweaks, but the mental fog persists.

Social interactions that once energized you now drain you, because your identity as a confident, excited founder feels distant. Your business story feels awkward to share, making press and podcasts painful.

You wonder if your business even needs you—maybe it would run fine without your anxious intervention. But you still fill your time with busywork because doing nothing feels scarier.

Your best new ideas seem out of sync with your current business. Deep down, you question whether you're the right person to lead now. You're haunted by the fear of starting over—losing the comfortable lifestyle you've built.

You're losing track, ignoring problems, and failing to make clear decisions. Physical stress and anxiety feel "normal," but your social life suffers. You've stopped connecting with peers because growth—the only thing founders comfortably discuss—has stalled.

You're desperately missing the spark, contemplating tearing it all down just to feel excitement again.

Here's the hard truth:

The success you've created now hinges on whether you're ready to evolve past your current bottleneck…

You.

You don't need more advice, hacks, or quick fixes. You need clarity, alignment, and strategic vision that reconnects you to your deepest purpose and reignites your business.

It's Time to Get Unstuck

Join a private community and proven program specifically designed for founders like you: leaders who've reached success but feel trapped by it. Together, we'll:

  • Restore Your Vision: Clarify exactly what you want next and communicate it confidently to your team.

  • Rebuild Your Team: Stop tolerating mediocrity. Build a committed, aligned, high-performance team.

  • Regain Your Spark: Reignite your natural creativity and passion that fueled your original success.

  • Replace Anxiety with Confidence: Transform uncertainty into strategic clarity and bold action.

You built this business. Now let's free you from becoming its limit.

Ready to find out how?

[Book Your Free Strategy Call Today]

Most founders hit a hard-to-talk-about dip in enthusiasm right after their business takes off.

Most Coaches focus on Solving Problems. I Focus on Evolving People to unlock business growth.

I help leaders design the structure and strategy that gets them out of the weeds and fully in their zone of genius.

Strategic Decisions (Exit & Transition) • Hiring Outside CEO/Executives •

  • What role have you avoided fully stepping into?

  • Which meetings on your calendar actually need you versus your title?

  • If the company doubled next year, would that excite or exhaust you?

  • When was the last time you spent a full day thinking about the future instead of fighting the present?

Many entrepreneurs and business owners have found enough success to grow, but they still do everything themselves—project management, customer service, sales—for years. It feels normal to actively operate every part of your business.

However, this kind of thinking creates a plateau in your growth and keeps your business small-time. You’re starting to realize the stuff that drives the business forward isn’t what they’re best at personally want to be doing anymore. They’ve outgrown the role they created for themselves.

‘Do I dig deeper? Or do I build something new?

Do I evolve into a different role?

I help founders like that figure out their next best step – the move that creates the most value for the company and gives them the most freedom, energy, and upside.

Sometimes that means restructuring leadership, sometimes it means repositioning the company entirely, and sometimes it means stepping out of the operator seat altogether.

What Got You Here Won’t Get You There

For Founders & Entrepreneurs Who’ve Built Success—But Now Feel Stuck.

You did it. You created what you set out to build. The business works. But now?

You’re not excited the way you used to be. The spark is missing. Your role feels more like a burden than a place of brilliance.

You find yourself:

  • Dreaming about the next thing—but afraid to say it out loud.

  • Hiring halfway, holding back from real commitments.

  • Planning endlessly, yet avoiding the hard decisions.

  • Feeling like your best ideas don’t align with what the business "needs."

  • Tolerating roles, meetings, and tasks that drain you instead of energizing you.

Deep down, you wonder:

  • "Am I still the right person to lead this?"

  • "What if making a change breaks what I’ve built?"

  • "Was my success a fluke? Could lightning really strike twice?"

You’re not alone.

The truth is, most founders hit this exact phase. The company grew because of you—but now it depends too much on you. The very thing that made your business successful is the thing holding it back from scaling further.

When Your Business Needs to Evolve—But So Do You

This is for the founder who:

  • Has created success but lost the personal inspiration that once fueled it.

  • Wants a clear growth path that aligns the business with their zone of genius—not just their calendar.

  • Knows it’s time to change roles, to step out of the weeds and into leadership that inspires again.

And yet struggles with:

  • Uncertainty about the right next steps.

  • Fear of breaking what’s working by making a change.

  • Feeling trapped in the success they built.

It’s Not About More Hustle—It’s About the Right Role

What if your business could double—without you at the center of everything?

What if stepping back could unlock growth instead of stalling it?

This coaching work is designed to meet you exactly where you are:

  • Help you reconnect to your own vision, your deepest inspiration.

  • Diagnose the patterns keeping you stuck.

  • Redesign your role and reset your strategy for the next chapter.

  • Guide you through the hard but necessary changes—so the business expands without running on your exhaustion.

You don’t need to start over. You need to evolve.

Let’s Find Your Next Role—the One That Lights You Up Again

[Schedule a Free Strategy Call] and discover how to step into the next version of your business—and yourself.

Hey, I’m David Sherry. I guide founders through personal and professional evolution — so they can unlock their next chapter, create again with energy and clarity, and build success that’s aligned with who they’re becoming.

Exec Coach to $20M+ brands, Investors, Multi-Business Owners and Highly Influential Digital Solopreneurs. I also founded Death to Stock which I now advise.

JACOB PETERS, 3X FOUNDER & CEO SUPERPOWER.COM

"David helps me see the forest through the trees.

It's like he’s seen every personal and founder hardship I've gone through before and always has great frameworks for dealing with these things."

  • 2,000+

    CEO & Executive Sessions

  • $1M-25M+

    Avg. Revenue

  • 50+

    Startups & Lifestyle Businesses

I WORK AS A PARTNER WITH FOUNDERS OF BUSINESSES LIKE

SEEQ PROTEIN

KINN JEWLERY

GOODONYA HYDRATION

SPREZZA

BACKDROP BUILD

MAKERPAD (EXITED)

DEATH TO STOCK

SUPERPOWER

GOLDEN

LAST CRUMB

SUNFLOWER

TRUFFL

PARTY ROUND

BRANDED NATIVE

SEEQ PROTEIN • KINN JEWLERY • GOODONYA HYDRATION • SPREZZA • BACKDROP BUILD • MAKERPAD (EXITED) • DEATH TO STOCK • SUPERPOWER • GOLDEN • LAST CRUMB • SUNFLOWER • TRUFFL • PARTY ROUND • BRANDED NATIVE

Matthew Jung, CEO Last Crumb, Venture Fund Partner, Owner of GOODONYA organic.

David doesn’t just tell you what to do, he helps you unlock who you are.

I’ve been working with David for years now; first as a Founder, CEO, and now as an Investor and multi-business owner.”

Free E-book

Stuck in the weeds of your business? Here’s what to do when you’re doing it all yourself and bottlenecking growth

Many entrepreneurs and business owners have found enough success to grow, but they still do everything themselves—project management, customer service, sales—for years. It feels normal to actively operate every part of your business. But this kind of thinking creates a plateau in your growth and keeps your business small-time.

Get over the hump of learning to delegate with examples of people who’ve done it, mindset shifts, and actionable templates.

Meet Your New Partner.

Maybe you’ve got co-founders, a team, investors, friends, a therapist, and family… none of which can totally understand the unique challenges your are facing.

Founders & CEO’s hire me as part business partner, part-confidant, and fully present strategist to customize and tailor recommendations with your best interests in mind. I’m here to help you and your business be great.*

*Based on whatever great means for you.

My Bio:

Hey, I’m David Sherry. I founded and bootstrapped a visual trend company called Death to Stock which is used by brands like Spotify, Squarespace, Bumble, and BBDO.

Starting in Columbus, OH, and working remotely since 2013, I built a 500k subscriber newsletter, hosted events around the country, and hired artists around the world from Thailand to Berlin, Auckland, and Miami. In 2016 I moved to Santa Monica, California, and in 2019 I brought on an NZ-based partner to buy of majority stake in the business which I now sit in on as an advisor.

As a coach, strategist, and advisor, I’ve worked to help 50+ founders and CEOs from viral E-commerce companies to disruptive fintechs, crypto, to private equity fund partners, and lifestyle business owners transform their business and their lifestyle.

Check out Death to Stock

JENNIE YOON, FOUNDER & CEO KINN JEWELRY

“He truly understands the challenges and what it's like being a founder.

Together we not only pinpointed the source of a given issue, but he led me to find a path to a solution.

Let’s Get Down to Business 

So you may have co-founders, a team, investors, or a therapist…But none of them know what all of the daily highs and lows are like when you’re fully responsible for your business’s success or failure.

I’ll provide perspective through challenges, point out blindspots, help you with major decisions, and help you clarify where your biggest growth opportunity might be.

  • David helps create an environment that can move as fast or as slow as needed to focus on the right conversations without bringing his own perspective or bias into the process. His work is as a sherpa helping create the space for me to work out concepts and connect the dots.

  • "Since I started working with David, my revenues have increased about 50% and I’ve taken the time I spent on the business down 30%, which I never thought would be possible.

    He's so good at helping you think through your work, do it intelligently, and helping me arrive at insights or conclusions on my own.

  • “He (David) truly understands the challenges and what it's like being a founder.

    Together we not only pinpointed the source of a given issue, but he led me to find a path to a solution.

    Telling my personal story and my brand's narrative with clarity and confidence was why I first sought out David as a coach.

    What I found instead is something much greater than what I'd anticipated—feeling empowered as a founder, allowing me to lean into my intuition.

    David created a space for me where I could be utterly honest, without any filters. “

  • "He’s the reason my company still exists + is bigger than ever even though I haven’t worked on it full-time in years.

    He coached me and improved my business in countless ways, super thoughtful in business and life."escription

Ben Zaver, FOUNDER of SEEQ

His approach has been incredibly impactful in helping me grow both personally and professionally.

After I hired a CEO to run the business, I transitioned to working with David more on my personal growth.”

ADRIAN ALFIERI, FOUNDER OF VERBATIM

“There's a big difference between pinging your founder friends and having someone dedicated to your business.

David became much more than a coach. He became a right-hand person who was part of the business, which is really rare.”