Cold Call Cap

Paid to call strangers who don't want to talk to me. Ex expert network, ex headhunter, now PE deal sourcing. Phone stories, staying on the line, career advice.

[Cold Call Cap @coldcallcap]

Early in my current role I called a tier-one target in the Midwest.

He picked up, was sharp, and spent 20 minutes grilling me.

Who I was. Why him. Why his business.

Never once talking about selling.

Then he said, "You've had 20 minutes and you didn't convince me."

I almost called right back.

Instead I sent a personalized gift tailored to his industry, right to their doorstep.

Tried confirming receipt over phone and email but went nowhere.

Eventually, after establishing the connection, I got a LinkedIn reply:

"Thanks for the gift. Who do I address the check to?"

I said no check. How about another call.

That rapport was enough to get him to meet someone on my team.

Persistence and understanding a Tier 1 target matter. You always treat them differently than your tier twos and tier threes.

[Cold Call Cap @coldcallcap]

The one skill across all three of my career chapters is trust.

In expert networks, Fortune 500 C-suite executives start to feel like friends on the phone after one call.

They laugh, they open up, and the call runs 45 minutes.

In headhunting, it's not just a coffee break at their bank.

We meet in person, grab a beer, build real relationships.

With business owners, especially family-owned services companies in the lower middle market, it starts as rapport on the phone and turns into texting and long conversations.

It's a relationship, not a transaction.

When you build trust, people want to transact.

They want to talk, and they'll listen to you.

[Cold Call Cap @coldcallcap]

@Sam_Rosati @guessworkinvest Sure, but I'd argue the objectives need to be on paper before the LOI, not after. Otherwise you're running what the seller built instead of what you bought it to become.

[Cold Call Cap @coldcallcap]

@HelenGuo_ Agree, many sellers always tell me “don’t email my business email”, “don’t call the front desk”, etc.

I get it.

But what if we presented this sale as a net benefit to them? Better insurance, better benefits, higher wages, and free lunch.

[Cold Call Cap @coldcallcap]

@mhp_guy It’s like courting a girl. You can’t seem desperate.

[Cold Call Cap @coldcallcap]

@blueprintsmb22 Nothing great comes easy

[Cold Call Cap @coldcallcap]

@BoringBiz_ Everyone spends most of their time at their W2, so what’s the solution? Buy someone else’s W2?

[Cold Call Cap @coldcallcap]

@WallStreetOasis In finance, there’s nothing more important than your first internship. No joke. DM me if you want advice, I spent years as a headhunter.

[Cold Call Cap @coldcallcap]

@Codie_Sanchez “We tell people to diversify their investments constantly.
Don’t put all your money in one stock.
Don’t put all your eggs in one basket.”

Yes, however, there’s a lot of noise on X about going all in. Stick to one thing and go for it. Contrary no?

[Cold Call Cap @coldcallcap]

@danmartell Reduce downtime at all costs.

[Cold Call Cap @coldcallcap]

@sweatystartup This is the first page of any management playbook. I’d argue that sometimes the employee shouldn’t have the answer, and as the boss you should. You’re the veteran. But yes, have the employee give their best shot.

[Cold Call Cap @coldcallcap]

@BobbyBizScout Depends on who you’re hiring. Imagine it’s a platform CEO who has scaled a buy and build roll up to $100M+ of annual revenue. It’s probably worth the hire.

[Cold Call Cap @coldcallcap]

If your calls are getting marked as spam during cold outreach your cooked. It’s worth asking owners time to time if they’re seeing it on their end.

[Cold Call Cap @coldcallcap]

@canteatIRR PE, Capital Markets, Consulting, Corproate M&A, Public Equities… literally everything

[Cold Call Cap @coldcallcap]

If you go to a networking event, don’t leave empty handed. Leave with at least 3 business cards.

[Cold Call Cap @coldcallcap]

I pitch why an owner should sell to private equity.

They usually say “not interested”.

Then I ask, "You've never had a magic number in your head?"

Usually they laugh.

Sometimes they give me one.

Then I ask how much revenue they did last year, and they want an NDA, and we go from there.

Some never give a number.

They say they will never sell, they are not sellouts.

That attitude is part of a bigger problem with how the public sees selling to private equity and capitalism itself.

But there is always a deal that can be done, and there is always a number.

[Cold Call Cap @coldcallcap]

@BizScout_ @BobbyBizScout If there’s significant key man risk, you’re not buying a SMB you’re buying a person… which is not the goal ofc. Cheers.

[Cold Call Cap @coldcallcap]

@HelenGuo_ There’s a lot of s*** to sift through!

[Cold Call Cap @coldcallcap]

@mhp_guy I dont sell websites, but I do cold call owners all day. The list is the easy part.

[Cold Call Cap @coldcallcap]

@litcapital We knew this was happening. All those YC AI wrappers are cooked.

[Cold Call Cap @coldcallcap]

@danmartell Isn’t that the whole point?