Dave Gerhardt

Hey I'm Dave Gerhardt. I created Exit Five, which has turned into the top community for B2B marketing professionals. Before starting Exit Five I had a 10 year career in marketing and grew from PR intern to CMO. I even once had hair! My wife says I'm more handsome now though, and she's quite pretty so that means a lot -- but the internet just boxes me in as the typical bald guy tech bro. So oh look, another bald tech guy writing on LinkedIn! whoopty freaking do.

Anyway. Where was I... OH. Receipts! I wanted to talk about receipts, because in a world of fluff and online influencers, I actually have some receipts and I want to tell you about them here because it signals power, credibility, and makes it seem like I'm super rich, so: I used to be pretty good at marketing, and my work as a marketer played a key role (at least I think so) in helping two software companies to successful exits: Drift for $1B+ and Privy for $100M+. I certainly helped the founders make a bunch of money, and I was able to comfortably purchase a brand new Toyota Sienna minivan for my family in 2021.

Today I spend my time working on Exit Five, and it's actually been super fun and given me a bunch of purpose. We're a team of six full-time team members now, and we have a private online community and host in-person events around the world. Plus there's a popular podcast and newsletter for marketers. We reach something like 20 MILLION marketers with our content every year, and we've got a pretty special thing going on. I hope to keep it going. You can learn more about it all at exitfive.com.

I spent most of my life in the Boston area but now live in the woods in Vermont with my wife, two kids, two cats, and one dog.

You can reach me at dave@exitfive.com if you want, but TBD if I reply. Depends on the message. But please don't send me any more swag or books. But if for whatever reason you do want to send me something, I play the ProV1x golf ball and like the low numbers.

PS. Find my podcast “The Dave Gerhardt Show” on Spotify

Founder & CEO

Exit Five is a media company focused on B2B marketing. We help B2B marketers build successful careers through our content and community. Learn more at exitfive.com

The CEO should put the Product team and Marketing team together. 

In lock step. 

To drive momentum and success for the company. 

I see so much about Sales and Marketing. 

Not enough about Product and Marketing. 

There should be a vision. And a roadmap. And regular launches. Some small. Some big. And this becomes the operating system for the company. 

You can CREATE momentum for your company by doing this. Deadlines drive actions. 

These regular launches give Marketing and Sales regular opportunities to talk to new customers. 

The CEO should be in the middle of this.

PS. If this topic lands with you and you're a CMO: we've been running a super secret group for CMOs / VP Marketing doing $25M+ ARR at Exit Five over the last few months and we're now accepting new members. Community is more important now than ever and it's all about who is in the room. We have curated the right room for you. If you want a peer group like this you can apply for a spot here: tinyurl.com/23h2c5eh

Founder: Exit Five. Community Builder. Former CMO. Building the top community for B2B marketers right now at exitfive.com

I didn't want my team to publish this talk. It was too good. Should have only been for the memory of the people that went to Drive this year.

But I'm also a marketer and understand the power of social media and free content, so fine. 

We published my pal Harry Dry's talk from Drive 2025 yesterday, and if you missed it he gave a masterclass in storytelling.

The long lost art of conflict and emotion in the world of AI, PLEASE GO LISTEN TO THIS MAN.

The first line of this clip says it all "You should know so much about your category you could write a book on it."

You're not creating a category to fit into Gartner or G2. You are creating a category because you are literally inventing a new of way of doing things!

That's the opportunity.

I'll put the recording in the comments (audio only)

Founder: Exit Five. The top community for B2B marketers.

Helping 9-5 pros build their Corporate Offramp | Land 1st client in a 1-person business you control

You’ve outgrown your 9–5. 
Now what? 

You’ve built a solid career. Maybe even a great one. But lately… 

The Sunday scaries hit a little harder.
You keep wondering, “Is this really it?”

You don’t hate your job. You’ve just outgrown it. And the money is the only part that serves you. 

You’ve done everything right.
But you still feel boxed in by meetings, org charts, and the constant anxiety of “restructuring.”

You know your skills are worth more – but no one’s shown you how to turn them into something of your own.

You're not trying to blow up your life.
You just want to know it’s possible.

That’s what the ‘Corporate Offramp’ is for.

It’s my step-by-step system to help high-performing professionals:
→ Package their skills into a client-ready offer
→ Build a simple audience of people ready to work with them
→ Land their first client in 120 days—without quitting their job

You’ll start earning outside your 9–5 and finally take control of what’s next.

This isn’t about quitting tomorrow.
It’s about progress. Building something – before you need it. 
And when you’re ready to start having control over your time. 

What others are saying:

“What really stands out about Brian is his authenticity. And his responsiveness is in a league of its own. His mix of broad entrepreneurial knowledge, specific expertise in areas like LinkedIn strategy, and straight-talking advice puts him at the top of my list.” 
– Melissa, ex-ed tech exec

“I started building while still in my 9-5, and landed my first client within 3 months (..before being let go by my company!).”
– Cassie, former tech manager

Here’s how to get started:

📥 Grab the Free 5-Day Solo Business Blueprint in my Featured section – and get the exact roadmap to land your first client without quitting your job (or even changing your LinkedIn profile). 

🎯 Want a faster path?
Join me for the Fast Track to Freedom Workshop – where I’ll walk you through:

• What to focus on (hint: not your website)
• Where 90% of your effort should go
• How to build an audience (without posting daily)
• The path to your first paid client – in 120 days

🎟 Save your seat: simplemanguide.com/workshop

Your 9–5 got you started.
Your next move is on your terms.

Brian Gallagher

The real risk isn’t leaving your job.

It’s staying just long enough that the comfort…

Becomes overwhelming.

People frame risk as walking away from stability. But stability’s not real. Just ask the people who thought they were ‘safe’ at Amazon or Microsoft.

The real danger is slower. Quieter.

You start caring a little less. You’re no longer motivated by what you're doing. You move through your days on autopilot.

You get lulled into sleep. Unsure what even makes you feel alive anymore.

You let people steal your time with fake urgency and pointless meetings.
You tell yourself you’ll make a move when things calm down.

But that moment never comes.

I remember when it started happening to me. The pay got better. The hours eased up.

On paper, everything looked fine.

But I didn’t like what the years ahead looked like.

I watched people higher up the ladder still asking permission for the simple things — a doctor’s appointment, a softball game, a random Tuesday.

And I knew if I didn’t draw a line, I might never draw one. I’d wait for the next bonus. Then the next. Then the next.

And 20 years later, I’d be so deep in it that walking away would feel impossible.

That’s how comfort works.
It feels just good enough that you stop questioning it.

Comfort doesn’t just keep you in the job.
It keeps you from becoming the person who’d ever leave it.

It’s a slow slide toward a life you never chose.

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In my last role, I was a VP in investment banking.

On paper? Looked great. But in real life… 

Yikes.

I’ll admit – the instant status it gave me when I told people what I did made me feel important. 

But I was constantly stressed. 

If I wasn’t at the office, I was dreading the next email ping from a managing director. 

Why? Because I had no visibility as to how my week would look. 

One minute I had a long weekend train trip planned. And an email ping could mean having to cancel everything. 

Honestly, it was chaos. 
But I kept telling myself it was “worth it.” 

Everyone seemed impressed with my title, so I was on the right path. That’s what I thought. 

Eventually I caved and said yes to something different. 

I started a fitness studio concept with a friend (while still at my job). 

Just a few classes a week. Nothing fancy.
But it was ours. We made the calls.

It didn’t make me rich. And unfortunately, it didn’t become my forever thing. 

But besides being the most fun I’ve ever had ‘working’, it did something else for me: 

It broke the cycle.

And once I got a taste of calling my own shots,
I couldn’t go back.

Now I help other people build something of their own too.

Because I’ve experienced both sides: 

Waking up dreading the work day. 
Waking up excited about what I get to build. 

And know I’m certain on which I’ll keep choosing.

I did a breathwork session last week.
Two words kept repeating.
And they stayed with me all week.

Kindness.
Vulnerability.

Two simple words. But they are the difference between forcing connection and creating real connection.

Kindness reminded me that everyone I talk to is carrying something I cannot see.

Clients. Prospects. Friends. Family members.
People on here scrolling through their day.

When I remember that, I show up better. My coaching is better. My conversations are better. My patience is better.

Vulnerability reminded me that the people I trust most are the ones who let me see the full picture.

Not the “everything is amazing” picture.
The human one.

So I am choosing to bring more of that into how I show up here.

And I will start today.

I am going through a breakup.

It has been difficult, but being around family, and keeping my schedule full, helps.
Movement helps. And so does work.

And during that breathwork session, something small set me off, and I realized how much I had been holding.

And yes, for a bit, I pulled back on some things while I got my footing again (work included).

But this experience is giving me something important.

A deeper appreciation for how much our personal lives shape the way we show up in our work.

A deeper understanding of what my clients feel when they are trying to build something while holding the rest of their life together.

And a deeper commitment to lead with kindness and vulnerability in every part of my life. Not just my business.

I want the people who follow my work to feel that they are seen, not judged.

And I want them to know that building a solo business is not separate from real life. It happens inside real life.

Work does not happen in a vacuum. Life does not pause while you build something meaningful. 

Who you are matters just as much (if not more) as what you do.

That breathwork session reminded me of that.

And it marked a change how I plan to show up here moving forward.

My brother’s dog, Norman, always helps too :)

There’s a point where learning stops helping — and starts hiding you. Brad was there too…

He’d been reading, thinking, and planning for months, but none of this got him any closer to his goals. 

Until he decided to stop collecting information and start building momentum.

One small shift – a few simple strategies, some accountability, and the courage to share his ideas publicly – changed everything.

The moment that started it all? He hit publish.

From there, things opened up fast.
Conversations he’d never had before.

And new confidence hammered home the realization that he didn’t have to get it perfect to make progress.

That confidence led to real connections, online and in real life.

Soon, Brad was turning his interest in health and leadership into work that actually paid him.

In fact, he’s earned income from three separate and distinct businesses he’s started. 

And now, if a layoff ever came, he wouldn’t panic. He’d have options. And the proof that he can create his own.

You don’t need more ideas. Or more knowledge. You need a first step.

If you’re ready, send me a note and I’ll share what that could look like for you.

The most motivated I’ve ever felt in my work didn’t come after a big win or a big paycheck.

It came on an ordinary morning in New York, with a plan, a coffee, and a blank page.

I remember the first time that feeling hit me.

I’d just gathered feedback on my first product – a simple ebook on slimming down in 30 days. I knew what to fix. The best days were still ahead.

I’d wake up, head to Gregory’s Coffee on 31st and 6th, order a cold brew (jet fuel!), and get creating.

It was the first thing I sold completely on my own. No extra work to deliver.

And when that first email pinged – a stranger had bought my book while I was sitting on my couch reading – I’ll never forget it.

It wasn’t about the size of the sale. It was about the shift it created.

I found the thing that I’d wake up early to build. And I had the plan to do it. 

Finding that bridge is a massive turning point. 

That’s when the work becomes exciting.
That’s when building something of your own becomes the most motivating thing you’ve ever done.

That’s when you stop being an employee in your own career. 

And start being the CEO of it.

At some point, you stop saying you’ll figure it out later – and realize you’ve been circling the same thought for years:

I want to start my own thing, but I don’t know where to begin.

And then the questions start to pile up: 

What would I even do?
How do I start without risking what I’ve built?
What if I fail and regret it?

So, you wait. I see it all the time.

People reach out, we talk about what their next move could look like, and then they disappear. A year later, sometimes more, they come back – same job, same questions, same stuck feeling.

Sure, they saved money by waiting. But they lost something more valuable. 

Time.

Until one day, they look up and realize a decade has gone by in a job they knew stopped fitting years ago.

I get it. I was there too. 

At first, there’s doubt.

You scroll through other people’s posts, quietly wondering if you could ever do what they’re doing. You change jobs, hoping a new title will make it feel different. It doesn’t.

Then comes curiosity.

You start exploring what your skills are really worth. You tinker with ideas. Maybe you even earn a little money on the side. Enough to prove it’s possible.

After that, something subtle changes.

You stop asking if you’re capable and start noticing opportunities everywhere.

People ask for your help. You begin to realize your job isn’t your identity anymore. It’s just your funding.

Eventually, confidence replaces doubt.

Your one-person business starts bringing in real income. You feel in control again.

And one morning, you sit down at your laptop and think, this is my life now.

That’s when you understand: you had it in you all along. 

You just needed a plan.

If you’re somewhere between doubt and confidence, the live workshop starts in a few hours – a free working session to map your first steps toward your off-ramp.

Join us here → https://lnkd.in/dbBue_6h

I had an eye-opening call with someone last week. 

It made me realize what a job interview really is… 

It’s an audition for your own career. 

The person on the call said: 
“I’m done. I never want to go through another interview again.”

They’re tired of pretending and of being told no by people who never really saw them.

The anxiety. The prep. The “hope you get lucky.”

The rounds of interviews where you give your best self, only to get ghosted, rejected, or land in a role nothing like what you were promised.

You’re totally auditioning. And I remember that feeling well.

Always second-guessing and doubting myself. 
Wondering if one wrong answer or one bored hiring manager was going to cost me the life I was hoping for.

That’s why twenty years without a job interview feels like a milestone.

It’s not just freedom from a boss, but freedom from depending on someone else – for them to reply, to notice, to choose you.

You start moving on your own terms again.

Building your own business gives you a different kind of safety. The kind that comes when you stop waiting to be chosen.

That moment when you realize you’re done interviewing is quiet, but it changes everything.

If you’re there now, I’ve put something together that might help:

Free workshop tomorrow → https://lnkd.in/dbBue_6h

And just maybe – you’ve already had your last job interview.

“It’s been four months and I still feel stuck.”
Someone told me this the other day.
Here’s what many underestimate when starting out: 

Just how easy it is to waste time trying to figure everything out on your own. 

And when building while still employed, it’s not helpful to see 15 different paths. All promising places to start, but unsure as to which is most viable. Which leads to revenue fastest. Which has the least speed bumps. 

So what do I see most people do? 

Dabble. Start researching. Build a website. 
Try one thing, then second-guess themselves and switch. 

And four months go by. Then six. Then a year. 

And somewhere quietly in the background, they’re thinking:
“I thought I’d be further along by now.”

Time spent stuck doesn’t just slow you down.
It starts to convince you maybe you weren’t meant for this.

You can figure it out alone. Lots of people do. 
But it usually takes them 18–24 months of guessing, circling, rebuilding, and trying to reverse-engineer the right sequence.

Or…

You get help. You get a map. You talk to someone who’s already walked the road.
And you collapse that timeline down to a fraction of what it would’ve been.

Some of my clients have signed their first client in less time than most people spend thinking about how to start.

Most people don’t fail.
They just run out of time and energy they didn’t know they were burning.

So if you’re four months in and still stuck, nothing’s wrong with you.

You’re most likely trying to navigate a process in the dark that someone could’ve lit up in a single conversation.

The question is no longer:

Can you do it alone?

It’s:

How much is the extra 12–18 months worth to you?

The hard part isn’t choosing.
It’s what happens before that: 

The limbo.

You go back and forth, trying to anticipate what you’ll lose with each option. You imagine every scenario, weigh every angle, and start thinking in circles.

Eventually, the pressure of not deciding becomes heavier than the decision itself.

And in the middle of all that, it’s easy to lose sight of what you might gain – not just from the path you choose, but from the clear vision and calm that comes after you choose it.

Once the decision is made, things get lighter. You can focus again. You’re no longer trying to live in two futures at once. You can stop running through pros and cons and finally begin shaping a plan around the direction you picked.

Starting a business is like this for a lot of people.

They think about it for months. Sometimes years. They wait for perfect timing, or a sign. They watch others do it but tell themselves they’re not quite ready.

What could be a season of momentum turns into a season of idleness. Moving – but not really going anywhere. 

Either way, you’re expending energy.

One way, you’re using it to your advantage.
The other – it just drains you. While nothing changes in your life.

And the longer you wait, the heavier it gets.

If you’ve been struggling to figure out the right next steps, and feel like you’ve just been swirling around in uncertainty… 

I’m hosting a free, live workshop this Tuesday to help lay out the roadmap for you. 

It’s for the ones who feel the pull to build something real – but also value the stability they’ve worked hard for.

We’ll cover:
• How to craft your elevator pitch
• Who to help, and how to reach them
• What to do first to land your first client

Join us here: https://lnkd.in/dbBue_6h

taplio

The Battle

Dave Gerhardt

Brian Gallagher

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taplio

The Battle

Dave Gerhardt

Brian Gallagher

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Dave Gerhardt's LinkedIn Performance

Performance ScoreBrian Gallagher's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreDave Gerhardt's LinkedIn Performance