Josh Braun

Braun Training

Are you sending lots and lots of cold emails but getting little to no responses?

Wish you could start more conversations with skeptical prospects?  

Wish granted: https://courses.joshbraun.com/p/badass-b2b-growth-guide

Email me: josh@joshbraun.com

Founder

Inside Selling is a podcast about how to sell without selling your soul through the simple acts of caring, being curious and making people smile.  

Listen here - https://joshbraun.com/podcast-episodes/

Host of the Inside Selling Podcast

Basecamp

--Helped Basecamp be even more awesome in the areas of customer success, churn mitigation and growth. 
--Created life-cycle drip email campaigns to convert trials to customers.
--Conducted customer interviews using the Jobs-To-Be-Done framework to increase conversion rates.

Head Of Sales

Jellyvision

--Managed and coached a 7-person sales development team  
--Doubled the number of weekly meetings set by the SDR team in 60 days
--Created and implemented my sales playbook and strategy for the SDR role
--20% growth of net new appointments 11 out of 13 months

VP of Inside Sales

--$2 - $10m in 8 years
--Exceeded my $720,000 annual quota every year
--Prospected for new business using cold emailing, cold calling & “trigger” events & referrals
--Won Fortune 500 accounts including IBM, GEICO, Verizon, McDonald’s, Fidelity, Disney & Aetna
--Created and implemented my prospecting sales playbook for Account Executives
--New and existing client development
--Channel development
--Contract, SOW and business proposals

VP of Business Development

CompassLearning

--Led development of new product lines for K-12 software platform representing $40 million in annual sales
--Planning, staffing and leadership of the K-12 software development organization (60-person team)
--Managed relationships with key third party partners and offshore development centers
--Helped open Austin office and build out an amazing company culture

VP Product Development

ChildU

--$0-$6m ARR in 3 years
--Created and implemented a repeatable sales process
--Helped open the Weston office and build out an awesome company culture
--Acquired by CompassLearning

Head of Growth

Megahedz

--Created and marketed an after school and summer technology camp for kids
--232 students enrolled in 1 year
--90% renewal rate

Palm Beach County School District

--Elementary school teacher
--Teller of stories
--Infused technology into the classroom to engage students

Teacher

Nickelodeon

--Production Assistant on Clarrisa Explains It All
--Created "behind the scenes" video
--Went shopping
--Cut fruit
--Served fruit

Production Assistant

Be the mint scoop in a sea of vanilla sales messages so you can start more conversations with skeptical prospects.

I created the Badass Growth Guide to eliminate commission breath. It gives you the best possible chance of starting conversations with people you don't know. It's a radically honest approach where prospects feel safe telling you the truth because they don't feel "sold" or "manipulated."

💥WHAT YOU GET:
➡️ More conversations with your ideal prospects.

I post weekly content about sales on LinkedIn.  
👍Like the content? Follow me. 👍

❤️I DON'T KISS AND TELL, BUT MY CLIENTS DO ❤️
"In one year, Josh has helped my company grow from 10 enterprise customers to over
200 with brand names like Twitter, Viacom, and Brown University" - Claire Coder, CEO at Aunt Flow

"We’ve got about 40 new meetings out of the training you provided." - Chris Murray, CEO at Oomph Inc.

“I used the email template from your playbook and it worked. I got to the decision-maker in one email and ultimately got the sale.” - Richard P. Perrott, WatchTower

💥NEWSLETTER💥
Join my list to get tips on being a red ❌ is a sea of white circle sales messages. 
https://joshbraun.com/newsletter/

💥WORKSHOPS💥
I facilitate workshops on two things: (1) cold calling + defusing objections (2) cold emailing. Inquire here -joshbraun.com/connect

💥PRODUCTS💥
THE BADASS B2B GROWTH GUIDE
https://courses.joshbraun.com/p/badass-b2b-growth-guide

POKE THE BEAR COLD CALLING METHOD
https://courses.joshbraun.com/p/poke

The Discovery Call Course
https://courses.joshbraun.com/p/discovery

TONGUE TIED SALES OBJECTION FLASHCARDS
Know what to say when prospects put you on the spot.
https://gumroad.com/l/objectionflashcards

💥INSIDE SELLING PODCAST💥
Learn sales tactics and strategies that will help you sell without selling your soul. 
Listen here -https://joshbraun.com/podcast
Learn more at joshbraun.com

Are you sending lots and lots of cold emails but getting little to no responses?

Wish you could start more conversations with skeptical prospects?  

Wish granted: https://academy.joshbraun.com/p/badass-b2b-growth-guide

Email me: josh@joshbraun.com

The most controversial way to start a cold call:

“Hey Rick, it’s Josh Braun, how’s it going?”

Every time I post that line, someone crawls out of the woodwork foaming at the mouth like I just insulted their grandmother.

“NEVER ask how someone’s doing!”
“It’s fake!”
“You’ll get hung up on!”

Relax, Carl. It’s not witchcraft. 

You know who says “how’s it going”?
Humans.
Baristas. 
Neighbors. 
Friends.
People who aren’t trying too hard.

You know who asks for 27 seconds?
Salespeople. 

If “how’s it going” sounds weird coming out of your mouth, don’t say it.
If it sounds natural, say it.

It’s always worked for me because it sounds like how I actually talk.

The secret to a good opener isn’t the script.
It’s sincerity.

If it sounds natural to you, it’ll sound natural to them.

Struggling to book meetings? Getting ghosted? Want to sell without pushing, convincing, or begging? Read this profile.

Five ways I practice patience.

1. When I go to the grocery story I choose the longest line. 
It’s my way of rewiring the urge to rush.

2. When someone’s upset, I resist the impulse to fix it.
I just mirror and name what they’re feeling.

3. When a friend or a child talks about something that doesn’t interest me, I lean in harder.
I listen with curiosity instead of waiting for my turn to speak.

4. When I’m looking for a parking spot, I pick the one furthest away.
It forces me to slow down.
To walk.
To notice the sky, the air, the sound of my steps.
It’s a small rebellion against convenience.
A reminder that life isn’t a race to the front.

5. And when I’m stuck in traffic, I remind myself it’s temporary. The problem isn’t the traffic. It’s my reaction to the traffic. (Read that again). 
I also imagine there’s an accident up ahead and silently hope everyone’s okay.

Patience isn’t trying to calm down.
It’s being present with what is, even when you’d rather be somewhere else.

Morgan Snyder wrote:

“Your LinkedIn headline is NOT the place for your family roster. No one is impressed that you’re a ‘2x Dad.’
I’m sorry. It had to be said. If you’re offended, please unfollow.”

My take?

If being a dad is part of what anchors you, why wouldn’t it belong in your headline?

For some, “2x Dad” isn’t a flex.
It’s a compass.

A way of saying, “This is who I am when the laptop closes.”
A quiet reminder that there’s more to life than pipeline and performance reviews.

LinkedIn isn’t just résumés and revenue.
It’s people.

People with families.
People who make pancakes on Saturdays and wipe tears before Zoom calls.
People whose worth can’t be summed up in a job title.

So if someone wants to write “2x Dad,” “Cat Mom,” or “Loves Coffee” in their headline, I’m all for it. 

That’s not unprofessional.
That’s human.

And the moment we start policing authenticity,
we lose the very thing that makes this platform worth showing up for.

Authenticity doesn’t need an audit.

A salesperson said my name ten times in twenty minutes during a discovery call. 

“Josh, let me tell you why that’s important.”
“I totally get it, Josh.”
“Josh, can I be honest with you?”

By the end, it didn’t feel personal.
It felt… tactical.

Somewhere along the way, people took Dale Carnegie’s line:
“A person’s name is to that person the sweetest sound in any language”,
and turned it into a sales technique.

But here’s the thing:
It only sounds sweet when it’s sincere.
Not when it’s scripted.
Not when it’s used like a seasoning you sprinkle every few sentences to build rapport.

You don’t build rapport by saying someone’s name.
You earn it by understanding them.
By listening.
By caring more about what they’re saying than what you’ll say next.

The sweetest sound isn’t my name.
It’s silence, when someone’s listening.

Why top salespeople leave? 

It’s not the selling.
It’s the sense that the better they do,
the heavier the load becomes.

They carry the team.
They exceed the number.
They create value.

And yet..

The target moves.
The quota climbs.
The finish line disappears.

It’s like handing a monk more water to carry
because he reached the temple faster.

But great sellers aren’t pack mules.
They’re professionals. 

Reward excellence with trust.
With ownership.
With stillness.
With more money. 
Not just another mountain.

Because if every summit becomes a steeper climb,
don’t be surprised when they stop hiking.

Many moons ago, I sent the same cold email to 23 people at VPI Pet Insurance.

All 23 forwarded it to the same person Leo. He was the one responsible for what I was selling.

A few hours later, I got an email from him:
“Any seller who spams my company is blacklisted forever.”

Ouch.

So I did something most people wouldn’t.
I picked up the phone.

He answered.

“Leo, this is Josh with Jellyvision. I’m the guy who thought it was a good idea to send an email blast. I’m calling to apologize.”

Leo paused.
Then he vented.
Then he gave me a masterclass on how to sell to him.

A few months later, VPI became a client.

Sometimes the best way to recover from a bad impression
is to drop the sword and be vulnerable.

When I was younger, “rich” meant:

Supercars.
Shiny watches.
Big homes.
Fancy tile.
Expensive restaurants. 

Now rich means:

Waking up without an alarm. 
Not asking anyone for time off.
Walking slowly.
Swimming in the ocean. 
Cooking a healthy meal at home. 
Spending the day my way.
Reading for the sake of reading.
Playing guitar without an end goal.
Daydreaming.

The older I get, the more I realize … 
the richest days don’t cost a thing.

Here’s a call opener I never heard.

That made me lean forward:

“Hey Josh, this is Riley Jones. You don’t know me. Want to hear something cool?”

I froze.
Smiled.

No begging for 27 seconds.
No “did I catch you at a bad time?”
Just a clear, unexpected question that made my brain light up.

It worked because it opened a gap,
That split-second moment when you know just enough to realize you don’t know the rest.

The brain hates that gap.
It’s why we binge watch shows on Netflix. 
Brains want to close the gap. 
It’s like a mental itch your brain wants to scratch. 
So I stayed on the line.

That’s the power of curiosity.
It’s not just how you close the gap ,
It’s how you open it.

If you want to be a better closer, start by being a better opener.

I once worked for someone who treated Sunday evenings like a warm-up for Monday.

Just as the sky dimmed and dinner hit the table,
my phone would light up.

Subject line:
“Not urgent. For tomorrow.”

But here’s the thing,
once the email lands, tomorrow begins.
You might think it can wait,
but for the person on the other end, it’s already started.

Their body might be on the couch,
but their mind is now at their desk.

It’s the modern version of hearing footsteps outside your tent.

You’re safe, but your system doesn’t know that.

So if you lead people, remember:
Boundaries aren’t just about time.
They’re about rest.

If you want better Mondays,
don’t steal Sundays.

Let your team exhale.

How do you get more comfortable making cold calls?

Not by memorizing a script.
Not by psyching yourself up with pump-up music.
Not by rehearsing clever rebuttals.

You get more comfortable by detaching from the outcome.

The reason cold calls feel so terrifying is because we attach our worth to the answer.

“Yes” feels like validation.
“No” feels like rejection.

But here’s the truth: the person on the other end isn’t judging you as a human being.

They’re simply reacting the noise you’re making. 
Your words and tone. 

It’s not personal.
It’s situational.

When you really see that, the fear loses its grip.

You get comfortable. 

The call isn’t a verdict on who you are.
It’s just a chance to start a conversation.

Some people will lean in.
Most won’t.
And that’s okay.

Because your job isn’t to convince everyone.
It’s to find the few who are open right now.

You’re not closing, you’re opening.
You’re sorting not selling. 

The shift is subtle, but powerful:
Stop seeing calls as battles to win or lose.
Start seeing them as doors you knock on.

Some stay closed.
Some open a crack.
And a few open wide.

Your job is simply to knock. 
Calmly. 
Consistently. 
With humble curiosity. 
Without attachment.

Comfort comes when you realize you don’t control who opens the door. 
You only control the knock.

A seller ask how to overcome “Call me in Q1.”

Here’s my take.

Instead of overcoming, try listening.

“Not now” isn’t a rejection.
It’s information.

You’ve identified the right person.
You’ve opened a line of communication.
Now your job is simple: stay top of mind without being a pest.

This post is an example of staying top of mind. 
One day you might head over to my website and buy. 

People buy for their reasons and on their timeline. 
Trying to “overcome” timing just makes people feel pushed.

I’ve closed so many deals by listening instead of convincing.

Fruit doesn’t ripen faster because it’s the end of Q4.

So plant the seed.
Water it. 
And let it ripen when it’s ready.

The other day, I walked into Hugo Boss

Three steps in: “Can I help you?”
Without thinking: “No thanks. Just looking.”

Truth is, I wasn’t just looking. 

That quick deflection is what I call the Zone of Resistance. It appears the moment you feel sales pressure.

As sellers we trigger it by pushing.
Convincing.
Persuading.
Begging.

Trying too hard to make something happen. 

When people feel pushed, they pull away.

Imagine if the salesperson said this instead when I walked in:

“Business trip?”

I would have said, “Actually no, a wedding.”

A neutral question. 
A guess. 
A different energy.

Elicitation invites correction or conformation instead of defense.

It lets the other person come toward you.

Same thing when cold calling.

“Coffee machines have small spots where bacteria like E. coli and staph can grow, especially the spout and drip tray. How do you usually keep yours clean?”

That question doesn’t sell.
It reveals.
It makes people pause and see something new.

When curiosity arises, resistance fades.

The conversation becomes effortless.

Selling isn’t about convincing.
It’s about creating space for discovering.

To be a better closer, be a better opener.

Some people will tell you they don’t take cold calls.

That’s their path.

No need to resist it.
No need to turn it into an objection to handle.

Pause for two beats.
Unlench. 
Thank them for the moment.
Ask if you can email them. 
Then move on to the next person.

The river doesn’t argue with the rocks.
It simply finds another way around.

Stop what you’re doing.

Pick one prospect who ghosted you. 

Tweak this email and send. 

It has a 100% response rate. 

That’s because no response is a response. 

——

Hi Pete,

It seems like you decided to hit pause on the cold call workshop. Perhaps I dropped the ball somewhere along the way.

I know this is a big ask. Would you be open to sharing some feedback so I can make it more relevant next time? Was it price, timing, my receding hairline?

Whatever the reason, I know you have a lot of options for sales training so thanks for considering me. 
______

The Psychology

1. Empathy and Understanding

By acknowledging that Pete “decided to hit pause,” you show you’re not pressuring or blaming him. This neutral and empathetic framing reduces defensiveness and keeps the door open for future dialogue.

2. Acknowledging potential fault. 

Phrases like “Perhaps I dropped the ball” signal humility and accountability, which make you more approachable. It shows Pete that you’re focused on improving, not just selling. Something people respect and respond to.

3. The Power of a Big Ask

Explicitly saying, “I know this is a big ask,” recognizes that providing feedback takes effort. This transparency often increases the likelihood of compliance because you’ve preempted any resistance.

4. Humor to Disarm

Injecting humor with “my receding hairline” makes the message feel lighthearted and human. Humor can break tension, encourage connection, and make people feel more comfortable responding honestly.

5. Gratitude

Reinforces positive feelings about you and your professionalism.

6. Future Focus

Asking for feedback “soI can make it more relevant next time” is a forward-looking request. The subtext is there’s no pressure to make a decision now.

Here’s how I know a salesperson is an amateur.

It’s one tell.

They talk more than they listen.

It’s not because they’re arrogant.
It’s because they’re afraid.

Afraid of silence.
Afraid of losing control.
Afraid that if they don’t sound smart, they won’t sound valuable.

So they fill every pause with proof.
Stats.
Stories.
Slides.
They try to earn trust through words.

Prospect: “Reps feel off balance when they hear objections.”
Seller: “I hear that all the time. You remind me of a client who had a similar issue. After taking our training…”

The problem?
If you’re convincing, you’re losing.

Why?

Trust doesn’t come from convincing.
It comes from understanding.

When you talk too much, you send a signal: “My interests matter more than yours.”

When you listen, you send a different one: “Your interests come first.”

Listening sounds like this: 

Prospect: “Reps feel off balance when they hear objections.”
Seller: “What’s your theory on why that is?”
Prospect: “Well, for starters…”

That’s the moment people open up and tell you the truth.

No truth, no trust.
No trust, no transaction.

Remember:
People don’t buy because they understand you.
They buy because you understand them.

Ready?

You’re working a conference booth.

Someone walks up and asks,
“So, what do you do?”

You launch into your polished elevator pitch.

“We’re an AI-powered platform that streamlines operational efficiency by…”

Their eyes glaze over.
They nod politely.

And slink away before you can scan their badge.

Now contrast that with this:

They ask,
“What do you do?”

And you say:
“To make this relevant for you, do you mind if I ask a couple of questions first?”

Now they’re talking.
About their role.
Their project.
Their pain.
Their curiosity.

And you?
You’re not pitching.
You’re learning.
You’re listening.

People don’t buy because they understand you.

They buy because you understand them.

I asked this question on LinkedIn:

“What is something that salespeople do that really annoys you?”

Here are some responses:

1. When a salesperson says, "That's a {good/great/terrific} question,” after every single question.Yuck.

2. Being inauthentic, like we are already friends when we don’t know each other.

3. When they ask questions like a census taker.

4. Trying to get someone on their timeline instead of aligning with it.

5. Listening to pitch rather than understanding the context of where the person stands today.

6. An avalanche of pushy follow-up emails & calls which are most annoying.

7. Aggressive follow-ups despite being told a “no” with valid reasons.

8. Opening with “So where are you based?” or “What's the weather like?"

9. When they try to recap or summarize what I've said but they're off base and don't provide the opportunity for me to clarify - just keep moving on with their talk track.

10. Don't do what they say they are going to do.

11. Attempting to create urgency.

12. Can’t give a demo or pricing without running me through some extra steps. that’s when I know that I am in *their* selling process, vs them meeting me in *my* buying process.

13. Being afraid to say the following when I ask a question they don’t have a confident answer for “I am unsure, can I get back to you on that”

14. Bump this to the top emails. I wish they would bump it down. 

15. “Just checking in.”

16. Being too excited!!! I'm thinking 'dude no need to be too excited.

17. Asking questions, getting insightful answers - but still going through their whole sales pitch without taking into account whatever I said before.

18. Pitching in the DMs.

19. When they hide information and don’t straight up answer questions but instead try to ‘qualify me’

20. “What keeps you up at night?”

21. “What is the biggest issue you fight on a daily/weekly basis?”

22. Make recommendations based on literally no discovery.

23. Endorsing me for things.

24. Making assumptions.

25. Call twice in a row to get through my do not disturb setting on my phone.

26. When they ask the same question ten different ways because the first 9 times they asked I didn’t express enough pain.

27. Bad targeting. I get so many messages assuming my job is something totally different than what it is.

28. That "robotic" mechanical tone of voice, spilling out everything without stopping.

29. Trying to pretend that they're not trying to sell me something.

30. Bashing competitors.

Every salesperson has two wolves inside them. 

Only one helps you grow.

A Cherokee elder once told his grandson,
“There are two wolves inside of me.”

“One is angry, frustrated, and full of blame.
The other is calm, curious, and full of strength.”

The boy asked, “Which wolf wins?”

The elder said,
“The one you feed.”

Sales is full of moments that test which wolf you feed.

When a prospect ghosts you,
you can feed the Victim Wolf that takes it personally.
Or feed the Student Wolf that knows silence is part of the process.

When your manager doesn’t train you,
you can feed the Victim Wolf that complains.
Or feed the Student Wolf that trains itself anyway.

When you miss quota,
you can feed the Victim Wolf that blames bad luck or your territory. 
Or feed the Student Wolf that studies what could be improved.

When your post views have gone down, 
you can feed the Victim Wolf and blames the algorithm.
Or feed the Student Wolf and continue getting better at writing. 

You can feed the Victim Wolf and be miserable and powerless. 
Or you can feed the Student Wolf and be unstoppable. 

Because once you stop feeding the Victim Wolf,
nothing can throw you off balance. 

Feed the Student Wolf
and you won’t just sell more
You’ll be a lot happier too.

You choose who which wolf to feed. 
Choose wisely.

Everyone’s talking about what’s changing in sales.

AI SDRs.
ChatGPT-generated cold emails.
Personalization at scale.

But Jeff Bezos once said something that completely changed how I think:

“I very frequently get the question: ‘What’s going to change in the next 10 years?’
I almost never get the question: ‘What’s not going to change?’
You can build a business strategy around the things that are stable in time.”

That applies to sales too.

Here are five things that won’t change:

1. People will always avoid pressure
No one likes being pushed.
The harder you push, the harder they pull away.

2. People will always buy from those they trust
Trust takes time.
It’s built through tone, presence, and respect.

3. People will always struggle to see their own blind spots
The best sellers aren’t just problem askers.
They’re problem finders.
They’re mirrors.

4. People will always want to feel in control
Even if you guide the conversation,
they need to feel like the decision is theirs.
Autonomy is a basic human need.

5. People want to feel understood
People don’t buy because they understand you.
They buy because you understand them.

The tools will change.
The tech will evolve.
But humans won’t.

The best sales strategies aren’t built around what’s trending.
They’re built around what’s timeless.

Thanks, Jeff.

The best cold call I ever received was from 🤿 Kendra Warlow.  

At the time, she was an SDR at Gravy.

See if you can spot why the call worked so well 👇

⸻

Kendra: “Hi Josh, this is Kendra with Gravy. Sorry about the background noise. I’m calling from the Starbucks drive-thru. How’s it going?”

Me: “Good. What are you ordering?”

Kendra: “Vanilla latte. What’s your go-to?”

Me: “Not a coffee drinker. What can I do for you?”

Kendra: “I was looking at your courses. Are you recovering failed and declined credit card payments yourself, or are you using an external recovery team?”

Me: “I don’t think I have failed payments. I use Stripe.”

Kendra: “So you frequently log into Stripe to check the failed credit card payment report?”

Me: “I actually don’t. Not sure what that even is.”

Kendra: “If you’d like, I can email you instructions on how to check if you have failed payments in Stripe. If you do, perhaps we can chat.”

Me: “Sure.”

⸻

A few minutes later, I got an email with instructions.

Turns out, I didn’t have failed payments.

But if I ever do, I know exactly who to call.

So what was it about that call that made me lower my guard?

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