For founders entering a new chapter

AI Advisory for
Independent Founders

I help independent founders build the next version of their business with AI. We work through what could change, choose the opportunities worth pursuing, and give the team a practical way to move forward.

David Sherry seated with a book in a bright studio

From my work advising founders

Last CrumbKinnVerbatimGolden PodcastsGOODONYA
“David became much more than a coach. He became a right-hand person who was part of the business, which is really rare.”
Adrian AlfieriFounder, Verbatim
More founder perspectives ↗

From my work advising founders

Good work is personal.

“My revenues have increased about 50% and I’ve taken the time I spent on the business down 30%. He’s so good at helping you arrive at insights on your own.”
Christian BenderGolden Podcasts
“He’s the reason my company still exists and is bigger than ever, even though I haven’t worked on it full-time in years.”
Jordi HaysCapital & Branded Native
“David became much more than a coach — a right-hand person who was part of the business. That’s really rare.”
Adrian AlfieriVerbatim
“David doesn’t just tell you what to do. He helps you unlock who you are.”
Matthew JungLast Crumb · GOODONYA

You have a business that works.
You’re deciding what comes next.

A new offer or direction.

Could AI make a new product or service possible, or change something already on your roadmap? We’ll weigh the opportunity and choose a useful first test before you commit.

Room to grow without adding complexity.

Could AI help your team handle more customers, or change the role you need to hire for? We’ll look at where the business is stretched and what’s worth testing next.

A company that needs less of you.

Too much still runs through you. We’ll identify one part of the work where your knowledge or decisions are a bottleneck, and explore how AI could help your team take ownership.

Bring your next chapter to a Vision Session.

Tell me what you want the business to become and the decision you’re facing. We’ll work through where AI could help and identify a practical next step.

Request a free 45-minute Vision Session ↗

How we work together

Understand what’s possible.
See what comes next.

We work from your goals and the realities of your business. You build your understanding of AI, choose where to use it, and give your team a clear place to start.

Connected circuit boards suspended against a pale background
  1. 01

    Vision

    See what AI makes possible for your company.

  2. 02

    Roadmap

    Choose what to change and what to build next.

  3. 03

    AI fluency

    Learn enough to lead your team through the change.

  4. 04

    Putting it to work

    Test a new way of working and learn from it.

See the approach in practice ↗
David Sherry working on a laptop beside a window

I bootstrapped Death to Stock, grew it to 500,000 subscribers, and eventually handed the reins to a new CEO.

More about David ↗

Work directly with David

I’ve built a company.
Now I help founders
rethink theirs.

Two 60-minute sessions each month, directly with me.

I’m a thought partner as you learn to lead with AI. Together, we rethink your roadmap, decide where AI can take on work, and make a plan your team can test. As the tools change, we look at what matters for your company.

I guide the work
Build your AI fluency, choose priorities, and review what you’re learning.
Your team puts it into practice
Try the changes, keep human review where it matters, and bring back what you learn.

Hands-on implementation is scoped separately.

Book a 45 min Vision Session ↗

From The Elevator

The AI-Native Company

Notes on AI, building companies, and the decisions behind the work.

Read & subscribe ↗

Ready to rethink
what comes next?

Bring what you’re building and where you feel stuck.
We’ll find one change worth exploring.

Book a 45 min Vision Session ↗