The Great Ownership Transfer

The Great
Ownership
Transfer.

Six million businesses. $5 trillion in enterprise value. From SBA-financed acquisitions to $1M–$5M EBITDA lower middle market deals — the largest ownership transition in modern American business history, and most operators will face the hardest phase entirely alone.

The scale of the transfer
6M
small businesses facing ownership transitions as baby boomers retire by 2035
$5T
in enterprise value among viable candidates for sale
12M
jobs that effective transitions could keep in place
$3T
in new household wealth unlocked by closing participation gaps
Source: industry research and SBA data, 2025–2026
Every deal has financial risk
We underwrite the execution risk.
The execution gap

The deal closes.
The execution gap opens.

Six million businesses are changing hands. The financial risk of buying one is well understood. The execution risk — what happens after the deal closes — is not. Advisors disappear. The seller leaves on Day 30. The operator is running a business they have owned for three weeks with no playbook, no peer network, and no one to call.

"The seller left on Day 30. By Day 45 I had discovered three things that weren't in the financials, two key vendor relationships that were personal to him, and a process that only one employee knew how to run — and she was thinking about leaving."

A Five Experts member — post-close operator, Year 1

Well-capitalized acquirers surround every deal with a bench of operators, CFOs, and functional experts — deployed from close through exit to drive the 100-day plan, address key-person risk, and build the value creation roadmap. Most LMM acquirers have none of that.

Five Experts is that infrastructure. Not a marketplace. Not a directory. A coordinated system — the right expert at the right phase, from the first deal search through succession and exit.

Small business owner
What operators face without Five Experts
  • No structured support from close through Phase 5
  • Seller leaves and takes critical knowledge on Day 1
  • Fragmented advisors — nobody coordinating across phases
  • No peer network of operators who have done this before
  • Execution breakdown in Year 1 — loan default, value destruction, or a business that never reaches its potential
  • No coordinated support — advisors who disappear, a seller who leaves, and no one to call

"I spent 18 months preparing and thousands on courses and coaches. I thought I was ready. Then I got to LOI and realized I had no one who knew my deal, my situation, or what I actually needed next. I closed anyway. By Month 3 I was staring at a cash flow problem nobody had warned me about. That's when I found Five Experts."

A Five Experts member — post-close operator, Year 1
Five Experts is named for five phases

Ownership transfer is not a single transaction.
It is a five-phase journey.

Each phase carries distinct risks and needs different expertise. Click any phase to see who helps.

1
Aspiration & Preparation
Before the deal starts
Sample experts
Former searchers, ETA coaches, buy-side brokers, financial planners for search capital.
Five Experts
Get oriented before the search gets serious. Resources, templates, and a free intake call to understand exactly which experts would change your outcome and when.
2
Search & Sourcing
Find the right deal
Sample experts
QoE providers, commercial DD specialists, financial analysts, business valuation experts.
Five Experts
Vetted experts matched to your specific deal — coordinated through your dashboard, not sourced ad hoc.
3
Deal Structure & Financing
Close with confidence
Sample experts
M&A attorneys, SBA lenders, deal structuring advisors, CPAs with M&A experience.
Five Experts
Coordinates SBA structure, LOI terms, and the full capital stack — including introductions to lenders, attorneys, and equity sources.
4
Ownership & Value Creation
The longest phase
Sample experts
Fractional CFOs, growth strategists, operations consultants, HR advisors, former operators in the same sector.
Five Experts
The longest phase. The highest stakes. Five Experts stays through all of it — 100-day plan review, P&L benchmarks, fractional CFO, deal war room, operator peer matching.
5
Succession & Exit
Maximize the return
Sample experts
Exit planners, sell-side bankers, valuation experts, EBITDA optimization consultants, tax advisors.
Five Experts
Every decision post-close affects the eventual multiple. Five Experts is there through the full journey — including when the cycle resets at Phase 1.

* Sample experts shown — network continuously expanding. Engagements are hourly, fractional, interim, or full-time placement.

Small business owner
Phase 4 — the longest phase
Most value is built or destroyed
in the first year of ownership.
Your first expert call is free.
No pitch. No pressure.
Every member gets a free intake call with a member of the Five Experts team — before you commit to anything. Tell us where you are in your search or ownership journey and we will tell you exactly how Five Experts can help.
Book your free intake call →
The member dashboard

Your deal. Your experts.
Coordinated in one place.

FiveExperts
SQ
⬛ Dashboard
📅 Booked Engagements
★ Bookmarked Experts
💡 Suggested Experts
💬 Chat
📚 Value Creation Content
👤 Profile Settings
→ Logout
Dashboard
Welcome to Five Experts
The great ownership transfer is underway — trillions in lower middle market businesses changing hands over the next decade. Five Experts is the coordinated platform built for it.
View Suggested Experts
Booked Engagements
4
Total Appointments
1
Appointments Today
3
Total Upcoming
Upcoming Sessions View All
Fractional CFO · Zoom
Today · 2:00 PM · 60 min
M&A Attorney · Zoom
Thursday · 10:00 AM · 30 min
Deal Structuring Advisor · Zoom
Friday · 1:00 PM · 60 min
Bookmarked Experts View All
SBA
SBA Lending Specialist
Finance · Deal Structure
$275
QoE
QoE Specialist
Accounting · M&A
$300
HR
HR & Retention Expert
People · Post-close
$225
Suggested for you
MA
M&A Attorney
Deal Structuring
$350
LOI terms · SBA structure · Capital stack
Book session
CFO
Fractional CFO
SBA · Cash Flow
$200
SBA compliance · P&L benchmarks
Book session
COO
Fractional COO
Seller Transition
$175
Transition planning · Key-person risk
Book session
Upcoming sessions
Fractional CFO · Zoom
Today · 2:00 PM · 60 min
M&A Attorney · Zoom
Thursday · 10:00 AM · 30 min
Deal Advisor · Zoom
Friday · 1:00 PM · 60 min
Join to access your dashboard →
What operators say

A coordinated system
from first search through exit.

I closed my first acquisition in March. By April I was in the deal war room with a fractional CFO who had seen exactly this situation before. That conversation alone was worth ten times the membership.
James R.
First-time acquirer · $2.4M HVAC business · SBA financed
We placed a CEO on a $4M EBITDA deal through Five Experts. The behavioral assessment process surfaced things a standard interview never would. Our operator is now 18 months in and tracking above thesis.
Sarah M.
Independent sponsor · LMM deal, Southeast
I was on my third acquisition and still felt like I was starting from scratch on the people side. The operator peer matching put me in front of someone two years ahead of me in almost exactly the same business. That relationship changed how I approached Year 2.
David K.
Experienced operator · Third acquisition · $3.1M revenue
24hr
Average time to first expert match after upgrading
9
Expert domains — search through exit
5
Phases covered — from first search through succession
$295
Per month — less than one hour of M&A attorney time
Who Five Experts is for

Built for every acquirer.
From first deal to portfolio.

Whether you are closing your first SBA-financed acquisition or deploying capital across a portfolio of $1M–$5M EBITDA businesses — Five Experts is the coordinated execution system built to support every acquirer through every phase of the ownership lifecycle.

01
Searchers & acquirers
From SBA-financed acquisitions to $1M–$5M EBITDA deals — QoE, commercial DD, deal structure, and capital stack navigation — all coordinated through your dashboard. Free to join. Expert matching unlocks when you upgrade.
For searchers
02
Independent sponsors & investors
For independent sponsors deploying capital across LMM deals — behaviorally matched CEO placement, coordinated diligence, and post-close execution infrastructure. Built to protect your multiple from close through exit.
For sponsors
03
Post-close operators
You closed the deal. Now you are running it. 100-day plan review, fractional CFO, P&L benchmarks, deal war room, and curated peer group office hours with operators who have been exactly where you are.
Phase 4 support
Small business
Most firms disappear after close
Five Experts stays through
Phase 5.
Membership

Free to start.
Upgrade when you need execution support at any phase.

Monthly Annual — $2,950/yr 2 months free
Free access
$0/ always
No credit card. No commitment. The platform and resources are yours from day one.
  • Invitations to curated group Zoom sessions
  • 100-day plan template
  • Diligence checklist
  • Resource library
  • 1 free expert intake call
  • Dashboard access
Join free
Add-ons — available to all members
Expert sessions
Billed separately
Growth, marketing, finance, accounting, technology, former searchers. Hourly, fractional, interim, or full-time placement.
Diligence stack
Project rate
Full LOI package — QoE, commercial DD, legal DD, ops assessment. One coordinated engagement.
CEO placement
10% of year-1 salary
Behaviorally matched for execution fit — not sourced from a job board. Assessed before you see a name. Warm introduction once mutual interest is confirmed.
Common questions

Everything you need to know
before you join.

Still have questions? Reach us directly at Growth@FiveExperts.com

Is this just for post-close operators?
No. Five Experts is a coordinated system across all five phases — from the first search through succession and exit. Members join at Phase 1, Phase 2, and Phase 3 as often as they join post-close. The earlier you engage, the better your diligence, structure, and Day 1 readiness.
Is this like a job board or expert marketplace?
No. On a job board or marketplace you search, filter, and hope you pick the right person. Five Experts does not work that way. We learn your situation and tell you who you need. You do not browse a list of experts. We make a purposeful recommendation based on your deal stage, your business type, and what you are actually working through. The difference is between searching for help and having the right help find you.
Is this like an acquisition course or community?
No. A course is something you complete. A community is something you belong to. Five Experts is a coordinated system built to drive execution — the right support, at the right phase, organized around your specific deal from search through exit.
How is Five Experts different from a coach or advisor?
A coach gives you frameworks. An advisor gives you opinions. Five Experts is a coordinated system — vetted operators who have done exactly what you are doing, matched to your specific phase, and coordinated so knowledge transfers between experts as your deal evolves. It is the difference between a map and a team that has walked the path together.
How are experts vetted?
Every expert in the Five Experts network is invited — not self-listed. We vet on domain expertise, LMM experience, and what we call execution fit: whether they have actually done the work, not just advised on it. Candidates go through a review before joining the network.
How quickly will I be matched with an expert?
Within 24 hours of your intake call. Once you upgrade, we schedule a 30-minute call to understand your deal stage, business type, and what you are working through — then make a purposeful introduction with context on both sides. Not an algorithm. A curated match.
What if the match isn't right?
Tell us and we will rematch. Expert matching is not a one-time event — it is an ongoing relationship. If a match does not work for any reason, we make another one at no additional cost.
Can I cancel my membership?
Yes — with 30 days notice by email to Growth@FiveExperts.com. Your membership ends at the close of the billing cycle following your 30-day notice period. Annual memberships are non-refundable but can be cancelled before renewal with 30 days notice.
What does the free tier include?
The free tier is your foundation — Invitations to curated group Zoom sessions, 100-day plan template, diligence checklist, resource library, and one free expert intake call. It is designed to get you oriented and ready. Expert matching and execution support unlock with full membership.

The transfer is coming.
Be ready for it.

6 million businesses are changing hands. Join the coordinated system built to support every operator through every phase.