When you’re evaluating a business or an industry you don’t know well, the biggest risk isn’t what you see.
It’s what you don’t.
That’s why one of the most effective ways to reduce risk is to talk to people who’ve already lived inside the business you’re considering.
This is quick playbook you can use to do exactly that.
Why Industry Experts Matter
Financials tell you what has happened.
Listings tell you what the seller wants you to see.
Industry experts tell you what actually matters.
People who have built, run, or advised businesses in a space can help you spot:
- Hidden risks you wouldn’t know to ask about
- Operational realities that don’t show up in spreadsheets
- Where first-time owners typically get surprised
- What separates good businesses from landmines
This is how professional investors de-risk decisions. Most individual buyers don’t do it. They should.
Step 1: Identify the Right People
You’re not looking for generic advisors. You’re looking for insiders with scar tissue.
Prioritize:
- Former owners who built and sold businesses in the industry
- Retired or semi-retired executives from similar companies
- Industry consultants who work with businesses like the one you’re evaluating
Former insiders are often the most candid. They have nothing to sell and no incentive to sugarcoat reality.
Where to find them:
- Industry associations and past conference speakers
- Trade publications and quoted experts
- LinkedIn searches focused on prior roles, not current titles
- Simple online searches for authors, speakers, or commentators in the space
Step 2: Make the Ask
Cold outreach feels uncomfortable. That’s normal.
The goal isn’t to be clever. It’s to be respectful and clear.
Strong outreach does three things:
- Acknowledges their experience
- States exactly what you’re trying to learn
- Makes the ask small and reasonable
A simple approach works best:
“Hi [Name],
I’m exploring the purchase of a business in [industry] and came across your background at [company]. I’d really value your perspective and would be grateful for 20–30 minutes to ask a few questions. I’m early in the process and trying to understand what matters most.”
One important note: don’t lead with money. Paying turns goodwill into a transaction and often lowers the quality of the conversation.
Step 3: Run a Great Call
Once someone says yes, treat the conversation seriously.
Structure matters.
- Start with light rapport. Show you did your homework.
- Set expectations for the call. What you hope to learn and how long it will take.
- Give brief context. Two minutes max on what you’re exploring.
- Ask focused questions. One topic at a time.
- Listen more than you talk.
Before you hang up, always ask:
“Is there anyone else you think I should talk to?”
This is how one good conversation turns into five better ones.
Step 4: Follow Up and Stay Connected
Send a thank-you note. Reference something specific you found helpful.
If the conversation was valuable, keep them lightly updated as you progress. These relationships often turn into mentors, referral sources, or long-term advisors.
The Bigger Point
You don’t need perfect certainty to move forward.
You need fewer blind spots.
The knowledge is out there. The only real barriers are the willingness to do the work and the courage to ask.
Used well, this approach can dramatically reduce risk before you invest time, money, or identity into a business.