6M
small businesses facing ownership transitions as baby boomers retire by 2035
The Acquisition Operating System
The Great Ownership Transfer.
Six million businesses. $5 trillion in enterprise value. The largest ownership transition in modern American history, and most operators will face the hardest phase alone. Five Experts is the coordinated system built for all five phases.
No credit card. Join the community and get started free.
Your command center
Your whole deal, run in one place.
A working dashboard that organizes the entire acquisition lifecycle around where you are, so you always know what comes next and who to call.
The live member dashboard: the five-phase journey with your current phase, experts matched to it, the free intake call, and search metrics in one view.
The execution gap
The deal closes. The execution gap opens.
The financial risk of buying a business is well understood. The execution risk, what happens after close, is not.
01The knowledge walks
The seller leaves on Day 30, taking vendor relationships, process knowledge, and history with him.
02The advisors scatter
The deal team disappears at close. Nobody coordinates what comes next, phase to phase.
03The room goes quiet
No peer network of operators who have done this before. No one to call when it gets hard.
04Year 1 decides
Execution breaks down in the first year, and value is destroyed instead of built.
Well-capitalized acquirers close with a bench behind them. Five Experts is that bench for the lower middle market.
The scale of the transfer
$5T
in enterprise value among viable candidates for sale
12M
jobs that effective transitions could keep in place
92%
of U.S. small business exits end in closure, not a sale
Source: McKinsey Institute for Economic Mobility, 2026
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. Select a phase to see who helps.
Your peer set
Experts have done it. Peers are running the same play.
Your experts are private and one to one, people who have been through it and know what is coming. Your community is a different kind of value: a curated room of operators at your exact phase, running the same play in real time. Candid, specific, and high-signal, from people in it with you. Joining is free, and the room is organized by phase, so you are alongside people working through exactly what you are. Start there.
Members get a live calendar of group sessions, expert office hours, phase cohorts, and expert AMAs. See what's on and register once you're inside.
Inside the Five Experts community: phase spaces, live sessions, and the room organized around your journey.
Why members choose us
Why our members
Why our members
choose Five Experts.
- 01You are preparing for or actively pursuing an acquisition, typically $1M to $5M in EBITDA, or already operating one.
Phase 01 starts before your first deal, and the system runs through succession. - 02You intend to lead the business you acquire, in the operator’s seat or as its sponsor.
Phase 04 is built for the first 100 days: a weekly cash rhythm, key-person risk, and CEO placement when the plan calls for one. - 03You treat the search like a discipline, with criteria you can say no with.
Phase 02 turns sourcing into a funnel, and the Deal War Room puts real deals in front of peers who have been there. - 04You want experts and peers in the work with you, at every phase from preparation through exit.
30+ expert categories, a member community, and live monthly sessions, all in one command center. - 05You want a coordinated system and a partner for the whole journey, not a vendor for one step.
One system carries the search, the close, the operating years, and the exit, and it is already in place when the next deal begins.
Underwriting deals rather than operating them? Explore sponsor membership.
Membership
Free to start. Full membership supports the whole deal.
Monthly, or annual at $2,950/yr with two months free.
Free access
$0 / always
No credit card. No commitment.
Get oriented, meet the room, and see how Five Experts works.
- The Phase 01 (Aspiration & Preparation) community space, free & open
- Invitations to curated group sessions
- 100-day plan template
- Diligence checklist
- Resource library
- One free expert intake call
- Dashboard access
Full membership
$295 / month
$2,950 billed annually · two months free
The full operating system for your acquisition, organized around your phase. Not everything applies to where you are today, and that's the point. What matters most changes as your deal evolves.
- The command center: pipeline, funnel, outreach CRM, vault, financing tracker
- Experts, coordinated: matching, booking, chat, LOI & deal review (expert engagement)
- Peers & community: phase cohorts and members-only spaces
- Live sessions: group sessions, expert AMAs, learning by phase
- Playbook & content: 100-day plan review, value creation playbooks, exit readiness
The command center
- Deal pipeline: every active deal tracked through stages, from sourcing to NDA, LOI, diligence, and close
- Task board and broker CRM
- Search metrics: a full acquisition funnel from companies identified through close, with outreach logging and conversion rates that show where your funnel is leaking
- Seller outreach: a proprietary sourcing CRM to track every owner you contact directly, with status, follow-ups, notes, response rates, and bulk CSV import
- Document vault
- Financing: a live capital stack tracker and a 14-point SBA readiness checklist
Experts, coordinated
- Coordinated expert matching, booking, and in-platform chat
- Connections to SBA lenders and M&A attorneys, plus guidance on structuring your capital stack
- LOI and deal review with written feedback (an expert engagement, billed at the expert’s rate)
Peers & community
- Members-only community spaces for every phase
- Phase cohorts, small peer groups at your stage
- Operator peer matching, running the same play as you
Live sessions
- Group sessions for the whole network
- Expert office hours across all domains
- Phase cohort sessions
- Expert AMA (ask me anything) sessions
Playbook & content
- 100-day plan review with written feedback
- Value creation playbooks, saved in your dashboard
- Acquisition readiness guide and deal evaluation framework
- Performance tracking against your own plan
- Exit readiness tracking
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.
From our members
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. 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 surfaced things a standard interview never would. Our operator is 18 months in and tracking above thesis.
Sarah M.
Independent sponsor · LMM deal, Southeast
On my third acquisition I 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 the same business.
David K.
Experienced operator · Third acquisition · $3.1M revenue
Who it's for
Built for every acquirer. From first deal to portfolio.
01
Searchers & acquirers
From SBA-financed acquisitions to $1M–$5M EBITDA deals. Sourcing, diligence, deal structure, and the capital stack, all coordinated through your dashboard. Free to join.
For searchers →
02
Independent sponsors
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’re running it. 100-day plan review, fractional CFO, performance against your own plan, and a peer cohort of operators who have been exactly here.
Phase 4 support →
Common questions
Everything you need to know before you join.
Is this just experts, or is there a community too?
Both, and they're different on purpose. Your experts are private and one to one, you don't crowdsource your legal question from a forum. Your community is a curated room of people at your exact phase: peers living the same deal, organized into cohorts by where you are. Phase 01 is free and open to every member.
Is this like a job board or expert marketplace?
No. On a marketplace you search, filter, and hope you pick the right person. We learn your situation and tell you who you need, based on your deal stage, your business type, and what you're actually working through. The difference is between searching for help and having the right help find you.
How does expert matching work?
Once you upgrade, we schedule a 30-minute call to understand your deal, then make a purposeful introduction with context on both sides. A curated match, made by people who know your deal.
What does the free tier include?
The Phase 01 (Aspiration & Preparation) community space, invitations to curated group sessions, the 100-day plan template, the diligence checklist, the resource library, one free expert intake call, and dashboard access. It's designed to get you oriented and into the room. Expert matching and execution support unlock with full membership.
Can I cancel my membership?
Yes, with 30 days notice by email to Team@FiveExperts.com. Your membership ends at the close of the billing cycle following your notice. Annual memberships are non-refundable but can be cancelled before renewal with 30 days notice.
The transfer is coming. Be ready for it.
Six million businesses are changing hands. Join the coordinated system built to support every operator through every phase.