Nonprofits · EDO & ESOs · Startups

AI Strategy &
Executive Leadership
Built for Your World.

High Fives helps nonprofits, ecosystem builders, and startups cut through the AI noise and put it to work — with senior operating experience in the room, from strategy to implementation to fractional executive leadership.

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Smarter. Faster. Saner. Together.

Who I Work With

Three Sectors.
One Conviction.

AI advice is everywhere. Advice from someone who has actually worked inside your world is rare. I've led, built, and advised across all three of these sectors — and it shows in every engagement.

01 — Non-profits

More Mission.
Less Administrative Drain.

Your mission can't wait for a bigger budget or more staff. AI helps you stretch every hour and every dollar — without losing the human touch that makes your work matter.

Active in this sector

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02 — EDO & ESOs

More Founders Served.
Better Impact Stories Told.

You can't clone yourself to support every founder in your pipeline. AI multiplies your reach, sharpens your programming, and tells a clearer impact story to funders.

Active in this sector

Proximity Global · Soon
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03 — Startups

Real AI Leverage.
Without the Runway Risk.

You don't have time to evaluate every AI tool on the market. Get a clear-eyed playbook for where AI actually moves the needle — without the $50K consulting invoice.

Active in this sector

Explore this vertical →
Non-profits

Your Mission Is Urgent.
Let AI Handle
the Rest.

Most AI consultants talk about efficiency. I talk about mission. There's a difference — and if you've spent time in the nonprofit world, you feel it immediately.

The goal isn't to automate your work. It's to free up more of your time for the work only humans can do: building trust, serving clients, and driving change.

  • → Cut grant writing prep time without losing your authentic voice
  • → Automate donor communication while keeping relationships personal
  • → Build AI-powered program reporting that impresses funders
  • → Train staff to use AI tools confidently — not fearfully
  • → Develop an AI policy your board can understand and approve

Active Work in This Sector

  • Donate Equity ↗ CEO  ·  donateequity.com A platform connecting donors of privately held equity and stock with nonprofits ready to receive it — opening a new asset class for mission-driven giving.
  • Thumbprint Consulting ↗ President  ·  Proximity Matters Provides grant assistance and capacity-building support to nonprofits — helping organizations find, apply for, and manage funding with greater confidence.
  • Thumbprint Curriculum ↗ Project Lead  ·  Proximity Matters AI literacy curriculum initiative developing accessible training for nonprofit staff, including the AI for Long-Term Care (AI4LTC) program.
Talk to Larry About Your Org →

Common Starting Points

  • Grant writing & funder reporting workflows
  • Donor stewardship & email communication
  • Program data summarization & impact storytelling
  • Staff AI literacy training & workshops
  • AI acceptable use policy development
  • AI readiness assessment & roadmap
EDO & ESOs

You Can't Clone Yourself.
AI Can Multiply
Your Impact.

I've run an entrepreneurial support organization. I know what it's like to have 80 companies in your pipeline and one person on intake. AI doesn't replace the relationships — it makes them possible at scale.

Whether you're an accelerator, a SBDC, a chamber, or a regional EDO, High Fives helps you use AI to serve more founders better and tell a clearer story to your funders.

Most EDOs and ESOs are structured as nonprofits — but the work is different, the funders are different, and the mindset is different. This vertical is built around that distinction.

  • → Streamline founder intake, triage, and routing workflows
  • → Build AI-assisted mentor matching and resource recommendations
  • → Create automated impact reporting pipelines for economic funders
  • → Train your programming team to integrate AI into cohort delivery
  • → Develop AI tools for ecosystem mapping and gap analysis

Active Work in This Sector

  • Donate Equity ↗ CEO  ·  donateequity.com A platform for donating privately held equity and stock to nonprofits — a tool ecosystem builders can put in front of founders who want giving built into their cap table early.
  • Thumbprint Curriculum ↗ President  ·  Proximity Matters Developing AI role-based curriculum specifically designed for EDO and ESO staff — practical training that maps to the real workflows of ecosystem builders.
  • DealVue ↗ Strategic Advisor An AI-powered deal room that prepares founders for serious investors — a tool accelerators and ESOs can put in front of the investor-ready companies in their pipeline.
  • Proximity Global Partner  ·  Coming Soon A new venture in this space under the Proximity Matters umbrella — details to come.
Talk to Larry About Your Ecosystem →

Common Starting Points

  • Founder intake & pipeline management
  • Ecosystem mapping & resource indexing
  • Economic impact reporting automation
  • AI-enhanced programming & curriculum
  • Mentor & resource matching systems
  • Outreach & founder communications
Startups

Your AI Playbook.
Without the
$50K Invoice.

Founders get buried in AI hype. New tools every week. Breathless posts everywhere. Zero clarity on what actually moves the needle for a company at your stage.

High Fives cuts through it. We figure out where AI creates real leverage — in your operations, product, GTM, and team — and build toward it without blowing your runway.

  • → AI opportunity mapping — find the highest-ROI starting points for your stage
  • → Operational AI implementation: tools that save hours, not just minutes
  • → AI-powered customer research and market discovery
  • → Content and marketing workflows that scale without scaling headcount
  • → Articulate your AI strategy clearly before investors ask

Active Work in This Sector

  • DealVue ↗ Strategic Advisor DealVue is an AI-powered deal room for founders raising Seed through Series B — it prepares, scores, and shares investor-ready data rooms, with Clara AI stress-testing pitch decks before any VC does. Serving as a strategic advisor to the founding team on growth, positioning, and go-to-market.
  • High Fives Founder  ·  AI Strategy & Fractional CXO Consulting The consulting practice itself — AI strategy plus fractional executive leadership, for startups that need senior operating experience in the room without a full-time hire.

Building in the Louisville region? Amplify — the Greater Louisville and Lincoln Trail startup support organization — is a strong first stop for local founders. Larry led Amplify through June 2026; High Fives does not represent it.

Talk to Larry About Your Startup →

Common Starting Points

  • AI opportunity assessment & roadmap
  • Ops automation (CRM, comms, admin)
  • AI-powered customer & market research
  • Content & marketing workflow systems
  • AI pitch & investor narrative prep
  • Team AI literacy & tool adoption
How I Work

Consulting That
Actually Fits Your World

No 200-page reports that live in a drawer. No jargon-heavy decks. Clear strategy, practical implementation, and the support to make it stick.

01

AI Readiness Assessment

A clear-eyed look at where you are, where the real opportunities are, and what's worth doing first. Delivered as an actionable roadmap — not a report you'll never open.

02

Workshops & Training

Half-day and full-day sessions for teams, boards, and cohorts. Interactive, practical, tailored to your sector — not generic tech training with your logo on it.

03

Implementation Support

Strategy is nothing without execution. Hands-on help building and rolling out your first AI workflows — with your team, not for your team.

04

Fractional AI & CXO Advisor

Ongoing strategic partnership — monthly or quarterly. AI roadmap leadership plus senior executive support across strategy and operations, without the full-time hire.

How it works

01

Discovery Call

30 minutes. We talk about where you are, what's slowing you down, and where AI could realistically help. Free, no pitch.

02

Assessment

I go deeper into your operations, team, and goals. You get a clear picture of where to start and why.

03

Strategy & Roadmap

A prioritized action plan built around your budget, team capacity, and actual goals — not what's trendy.

04

Build & Sustain

We implement together, train your team, and build the capacity to keep growing without always needing outside help.

Larry Horn, founder of High Fives, standing arms crossed in a navy suit against a stone wall
About Larry Horn

Built From
the Inside Out.

"Most AI advice is built for Silicon Valley. The organizations I work with are building something more important."

Most AI consultants have read about your world. I've lived in it.

As a longtime startup ecosystem leader, I've spent years working alongside nonprofits, economic development organizations, and early-stage founders. I know what it's like to make big decisions with limited resources, small teams, and real stakes.

High Fives is how I put that experience to work — AI strategy, hands-on implementation, and fractional executive leadership for mission-driven organizations and builders who need senior operating experience in the room, not just advice from the sidelines.

Current & Active Ventures

CEO

Donate Equity

Equity & stock donation platform for nonprofits

President

Proximity Matters

Parent of:

Strategic Advisor

DealVue

Strategy & GTM advisory for early-stage startup

Founder

High Fives

AI & fractional CXO consulting · Smarter. Faster. Saner. Together.

Board & Civic Roles

  • Actors Theatre of Louisville Executive Committee · Chair, Nomination & Governance
  • VOA Mid-States Chair, Board Nomination Committee
  • InBIA Board of Directors
  • University of Louisville College of Business Advisory Board
Get Started

Ready to Make
AI Work for You?

Start with a free 30-minute discovery call. We'll talk about where you are, where you want to go, and whether High Fives is the right fit to help you get there.

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l@high5s.co  ·  high5s.co  ·  Louisville, KY — and everywhere.