Jon Hershman

Building a consulting business in real time. Advising series A-C startups on business develop & finance. 15x marathon runner.

[Jon Hershman @jonhershman]

What does a great @SlackHQ community look like (10k+ members)? Is anyone in a community they love and what makes it so great?

[Jon Hershman @jonhershman]

@david_perell, it comes down to risk appetite. There is none.

Attend any business conference in Chicago and the panelists will promote re-investing in the entrepreneurs, real estate, and organizations in the city.

In reality, the investors here don’t have the same risk appetite as managers on the coasts. Forcing any promising talent we do have to relocate and raise capital elsewhere.

It’s an endless cycle of Chicago rooted talent building amazing companies on the coasts.

No case studies. No mentors. No exciting, growing companies to work for.

[David Perell @david_perell]

Why isn't Chicago a more prominent place?

Big city, beautiful architecture, top-tier sports teams, a solid subway system, and one of the world's biggest airports. People called it Second City for years. The Chicago Bulls were absolutely dominant during the 90s, and three of the 2000s biggest names (Kanye, Obama, and Oprah) rose to fame there as well.

But the cultural spotlight has moved away from Chicago. I hear about cities like LA, SF, NYC, Miami, Dallas, Austin, and even Nashville much more.

There's got to be a good story here, and I'm curious to hear it.

[Jon Hershman @jonhershman]

Multiple calls with founders this week, and I keep getting asked to do the same thing.

Run the whole launch.

New product, new market, from zero.

And when I dig into what they actually need, it's never one thing.

It's sales, because someone has to get on calls with real customers.

It's finance, because someone has to set the price and hold the line in the negotiation.

It's ops, because someone has to turn a scramble into a cadence that repeats.

Most companies now call this work go to market.

What they're really saying is the work won't sit in one department, and they need someone who doesn't need it to.

Every company is messy. Every launch is messy.

The founders who see that clearly stop looking for a specialist and start looking for someone sharp across all of it.

So when a founder asks me to run the whole thing, I already know what they're really asking for.

[Jon Hershman @jonhershman]

"Head of Sales" is two different jobs.

Most founders hire the wrong one.

Early stage, no brand, no product-market fit, the job is strategy. Where to play, how to win. You learn it by running outbound yourself and sitting on every customer call until the pattern shows up.

Later, with a brand and a product that sells, the job flips to operations. Build the pipeline and the process that move deals without you in the room.

One rewards invention. The other rewards discipline.

Drop a great operator into a pre-PMF company and they'll build process around a motion nobody has proven. Drop a strategist into a scaled one and they'll reinvent what already works.

Most people can't stomach the early version. The blank page, the months of no. It's also the most exciting seat in the building.

The mistake isn't a bad hire. It's the right person for the wrong stage.

[Jon Hershman @jonhershman]

Closing is hard. Closing the wrong customer is worse.

Picture the monster quarter everyone celebrates, and then the two quarters spent quietly nursing deals that never should've signed.

That's the part nobody says out loud. A close that doesn't stick is a loan against next quarter, and here's the interest: your team burns its hours saving an account instead of hunting new ones, and when it churns anyway you have to re-close that revenue just to stand still.

You didn't grow. You paid to stay in place.

And it almost always traces back to one thing. Not the pitch, not the demo. Who you let into the pipeline to begin with.

Screen harder for fit up front, and the same effort finally stacks instead of resetting.

Closing is hard. Closing the right customer is everything.

[Jon Hershman @jonhershman]

I run sales for several AI products, mostly into industries that still buy software by the seat.

The hard part was never the demo. It's getting a buyer to stop grading AI like it's one more SaaS tool.

SaaS plugs in and waits. You buy the license, learn the features, build the workarounds when it doesn't fit.

AI runs the other way. It connects your systems instead of sitting next to them. It learns the business without an engineering roadmap, and it gets sharper the more you use it.

Once someone feels that difference, the questions change. They stop asking the price per seat and start asking what it could run for them.

Accounting. Support. Operations. The back office stops being headcount.

What's left is the part that was always theirs. The audience, the funnel, the strategy.

That's the pitch I get to make every week. Still the sharpest selling I've done in years.

[Jon Hershman @jonhershman]

The best companies I work with know exactly who their customer is.

Then they take the meeting with someone who isn't.

Most teams pick a lane and guard it. Narrow the niche, aim the marketing, ignore everything else. That focus is right. It's also how you miss the customer sitting one degree off your target.

The teams that win treat the ICP as a hypothesis, not a verdict.

They market to the narrow niche. But when a warm intro comes in slightly outside it, they say yes. Not radically outside. Slightly. Close enough that a real conversation teaches them something.

That's how you find true demand. Commit hard enough to have a target, stay loose enough to notice when the target is actually next door.

Know exactly who your customer is. Then take the meeting with someone who isn't.

[Jon Hershman @jonhershman]

@packyM And ring the liberty bell after. @KingJames

[Jon Hershman @jonhershman]

I've been running sales for a handful of AI companies. Almost none of the deals were won on the AI itself.

Five things I've picked up:

1. AI is table stakes now. Every competitor pitches it. Nobody's impressed.

2. The best AI is invisible. No integration, no onboarding, it just does the job like a person would.

3. Build it to grow with their team so they're not hiring to keep up.

4. Price it under what a full-time hire costs. Under the competition. Easy yes.

5. Pick up the phone. Being responsive still wins deals the tech can't.

Funny thing about selling AI. You still need humans to close the deal.

[Jon Hershman @jonhershman]

The most skilled salespeople aren't at the companies you've heard of.

At a brand-name company, the hard part is already done. The market knows you. The messaging is tested. The price holds. Your job is to execute a playbook someone else wrote.

Early stage, there is no playbook. You're figuring out where the buyers actually live, what language moves them, what price earns a yes. You build the hypothesis, design the experiment, iterate, then do it again on a fraction of the budget.

One job is execution. The other is invention.

That's why a top rep from a famous logo can stall the moment the playbook disappears, and why the operator who can build one from nothing is the rarer, sharper hire.

The most skilled salespeople are the ones writing the playbook, not running it. Usually at a company you've never heard of.

[Jon Hershman @jonhershman]

@thesamparr Barry is full of wisdom. Really enjoyed my conversation with him when we met.

[Jon Hershman @jonhershman]

@obj all I need is a chance. I promise it will be one of the best business decisions you will ever make.

[Jon Hershman @jonhershman]

Here's what I'm creating with TempoBD.

An agency that steps into any company and owns the revenue.

Most agencies hand you advice and walk. We take the whole thing.

On sales, we own the process end to end. We learn the market, find the customers, build the outbound, get on the calls, and push deals through the pipeline until they close.

On marketing, we own the engine. We write the copy, build the campaigns, and run the calendar so the whole thing moves with rhythm instead of randomness.

One team, accountable for the number. Not a vendor you manage. A partner who carries it.

We're early, but it's landing. Last B2B client closed 3 deals in the first 60 days.

That's the whole idea. Own the revenue, earn the trust, do it again.

That's what I'm creating with TempoBD.

[Jon Hershman @jonhershman]

I’m working on the go to market strategy for some pretty awesome companies right now.

Here’s what I’m seeing with AI.

No one is buying “AI solutions.”

Most buyers assume they can get the same output you promise by prompting ChatGPT themselves.

If your pitch is “we use AI,” you sound like everyone else.

What people actually buy is this:

More revenue.
Lower costs.
Faster turnaround.
Better accuracy.
Less manual work.

The companies winning are not talking about AI.

They are quietly using it everywhere.
Sharper ads.
Better copy.
Cleaner models.
Smarter targeting.
Tighter operations.

Then they sell the outcome.

We reduce your CAC.
We increase conversion.
We cut processing time in half.
We find customers your team is missing.

AI is the engine.

Performance is the product.

If the customer can’t feel the difference in their P&L, they do not care how you built it.

[Jon Hershman @jonhershman]

The single most important thing on a founder’s mind is how to reach and retain customers.

It’s the most talked-about part of go-to-market.

And yet what I see online is endless selling of “perfect” cold email sequences, ad funnels, and automation hacks designed to blast as many people as possible.

The truth is AI is about to make cold outreach even harder.

Everyone’s inbox is flooded with “personalized” messages.
Ads look the same.
Language sounds the same.

You’re not competing for attention.
You’re competing to be a needle in a much larger haystack.

The advantage is shifting back to relationships.

Warm introductions will carry a premium.
In-person conversations will outperform click-through rates.
Early GTM will reward trust over tactics.

When you launch a product or enter a new market, you don’t need millions of customers.

You need a handful of loyal advocates.

And those are far easier to earn through real human connection than through another automated campaign.

[Jon Hershman @jonhershman]

I posted online every day for two years, then in April 2025 I abruptly stopped.

But just because I stopped publishing, doesn't mean I stopped writing.

Since that time, my business has evolved.

Serving new clients and performing new functions.

I'm still learning what content converts, but for better or for worst, writing online is necessary for any entrepreneur.

I'm leaving opportunity on the table.

So the goal for 2026 - write and share more.

I got big things in the works, I think people will enjoy reading about it.

Happy New Year!

[Jon Hershman @jonhershman]

Traditional medicine is established to treat the disease.

Longevity & wellness intends to treat the patient.

There is no silver bullet, and much of the treatment can be tied to lifestyle.

That's why there are so many new concepts and businesses focused on fitness, nutrition, and sleep.

Because healthy, daily habits can be medicine for the right patient.

I am diving into all the business side of the industry and will be posting about it more frequently.

[Jon Hershman @jonhershman]

The challenge with the longevity industry?

You don't know who to believe.

Everyone and everything is backed by "deep science",

results are hard to quantify,

or show up much later in life.

The unfortunate truth: customers don't have the patience for unusable data, or unquantifiable results.

So in order to compete in this space, you have to create short term wins, progress charts, performance improvements.

Without sacrificing long term goals.

Not too many industries out there that can say the same.

[Jon Hershman @jonhershman]

People like to bucket "health & wellness" with "longevity" but they aren't the same.

You can be healthy: have a normal blood pressure, resting heart rate, etc.

But that doesn’t mean you are at optimal health.

The longevity movement is all about optimizing your health.

Going from a healthy state that checks boxes to an optimized one that increases healthspan.

Both are important and serve a purpose.

But when looking at companies in this space,

It’s important to distinguish between the two.

Very different customers.

[Jon Hershman @jonhershman]

Healthy doesn't mean optimal.

People like to bucket "health & wellness" with "longevity" but they aren't the same.

You can be healthy: have a normal blood pressure, resting heart rate, etc.

But are you optimizing your health?

The longevity movement is all about optimizing your health.

Going from a healthy state to an optimal one.

Both are important and serve a purpose.

But when looking at companies in this space,

It’s important to distinguish between the two.