Hey, 👋 Scott from The Sales Mastermind here.

Today’s edition only takes 3 minutes.

"Founders who sell" are universally excited to become "founders who lead sellers". But that transition is often harder than learning to sell in the first place.

Today we’ll cover:

• Storytime
• Sales Management is Different
• Sales Meetings
• The Larry

Storytime

I work with a founder who is an elite seller; he has closed millions of dollars' worth of deals.

His company is now big enough that it needs a founder-leader rather than the best salesperson.

To that end, we hired a seller in late 2025, and deals are closing. It's working, mostly.

Like all good leaders, the founder wants to support his seller by attending as many sales meetings as he can, lending the weight and gravitas of the company's "top dog" being available for clients.

But he often finds himself in conflict with his seller as to:

• Who is leading the meeting? and
• Who is controlling the emotional flow?

For example, during a meeting nominally led by the seller, the founder presented pricing. Normally, the founder would use a moment of silence to let the price hang in the air and force the buyer to speak next. But the seller jumped in right after the number was said and ruined the moment.

The founder is a self-described "control freak" and knows he is holding the company back by not allowing the seller the autonomy he needs.

Ultimately, the founder wants to relinquish control so his seller can learn, grow, and close deals on his own.

So, on this week's coaching call, we agreed that the founder would flip his role.

He is going to stop trying to lead sales meetings or control the emotional flow. He is going to stop being the expert.

He is going to become "The Larry".

Sales Management is Different

All early-stage businesses have three core teams.

• "Operations" or "Product" are the team that creates the product and/or does the work
• "Administration" are the team that keeps the business running, doing things like accounting, HR, etc
• Revenue are the team that finds interested buyers and turns that interest into paying customers.

And Revenue is the only team that operates as a pure chaos system, especially in early-stage businesses.

Meaning that the work of each other's team is, for the most part, linear and clear. For example:

• The Administrative team either keeps the accounting up to date or does not.
• The Operations team either completes the project or does not.
• But the Revenue team may do everything right and not close the deal. Or do everything wrong, but the deal closes anyway.

And if the Revenue team fails to generate enough money, the whole business collapses.

Therefore, founders struggle to become sales managers, even when they hire great sellers, because the risk is so high and the outcome is so chaotic.

Sales Meetings

When founders finally get around to hiring sellers, they need to learn to manage them rather than fight them, as if the founder were still an individual contributor competing for commission.

During sales meetings, that means playing the role of "The Larry", named for Oracle CEO Larry Ellison.

In Greek history, Oracles were revered individuals who had a direct line to the gods.

And importantly, they remained in sacred locations, far from most people, waiting for specific requests or questions before conducting divine readings.

The most famous was the Oracle at Delphi. If you've seen the movie "300," this is who King Leonidas visits for advice.

The Larry

The Larry is a modern-day Oracle:

• They join sales meetings but, after introductions, remain silent until called upon
• When called upon, The Larry gives direct, succinct, and positive answers
• The Larry never promises anything that might appear to undermine the seller
• The Larry never jumps in to correct the seller
• The Larry is a supporting and not the main act

Being The Larry is hard at first, just like a parent watching their child learn to ride a bicycle, the founder has to let their seller fall over a few times.

But The Larry is the only way to become the founder a growing business needs, instead of stunting your business's growth by remaining the only one who can close deals.

Being The Larry allows the founder to maintain authority and support their sales team through their presence. Meaning they will soon reduce the time they invest in closing new deals, since they have a competent sales team that works without them.

Until next week,
Scott Cowley

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