Dave Gerhardt

Dave Gerhardt

These are the best posts from Dave Gerhardt.

58 viral posts with 57,471 likes, 6,694 comments, and 1,487 shares.
10 image posts, 0 carousel posts, 1 video posts, 46 text posts.

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Shoutout to everyone in SaaS going home for thanksgiving trying to explain WHAT THE HELL you do to your family ✌️❤️

At least we have eachother.
Life is too short to work with a CEO who doesn’t get marketing.
Life’s too short to work for a CEO who doesn’t get marketing.

#marketing
Here at my 5 copywriting rules. Written on my phone on the car ride to Vermont over the weekend:

1. Write like you talk. Not like you as a marketer. But you. The real person. The same way you would write an email to your friend to set up a play date with the kids.

2. Write choppy copy. Short sentences work great. Each line should play off of each other. You don’t need to finish every thought in every line.

3. First line, second line. The goal of your first line of copy is to get people to read the first line. The goal of your second line is to get them to write the third, etc. Ex: This is how I write email. Subject line gets you to open. First line gets you to the second, third, fourth, etc. all the way to the CTA. And the PS reinforces the CTA.

4. Loud up with pronouns. You. Me. We. I. Yes. It’s OK to write in the first person. That’s how people talk.

5. Fill your copy with real examples. Not stock photos. Not highly manicured images. But real ones. To let people know you’re real. Upload pictures from your iPhone. Take screenshots of tweets. Those will boost up any email, blog post, or landing page.

#marketing
#copywriting
Here at my 5 copywriting rules // even for B2B

1. Write like you talk. Not like you as a marketer. But you. The real person. The same way you would write an email to your friend to set up a play date with the kids.

2. Write choppy copy. Short sentences work great. Each line should play off of each other. You don’t need to finish every thought in every line.

3. First line, second line. The goal of your first line of copy is to get people to read the first line. The goal of your second line is to get them to write the third, etc. Ex: This is how I write email. Subject line gets you to open. First line gets you to the second, third, fourth, etc. all the way to the CTA. And the PS reinforces the CTA.

4. Loud up with pronouns. You. Me. We. I. Yes. It’s OK to write in the first person. That’s how people talk. Be the GUIDE in your emails. You’re the messenger reaching out on behalf of your company because you can HELP them.

5. Fill your copy with real examples. Not stock photos. Not highly manicured images. But real ones. To let people know you’re real. Upload pictures from your iPhone. Take screenshots of tweets. Those will boost up any email, blog post, or landing page.
Salesforce is a 100+ billion dollar market cap company.

AND THEY ARE STILL STRUGGLING TO TELL PEOPLE WHAT THEY DO.

They are running a massive brand campaign right now to go deeper. People know Salesforce, but the average person doesn't actually know what Salesforce *does.*

I loved hearing that. Because it's a reminder that messaging is HARD and it's never done.

#marketing
I miss when LinkedIn was just people posting:

- PS we're hiring!
- Look at this award we won!
- Come to our webinar tomorrow!
- Have you read our new blog post?

Hey. Channels evolve, and I think LinkedIn has changed for the better. You should get rewarded for interesting content and having something to say -- not just posting links.

#marketing
I've joined Drift as Chief Brand Officer, reporting to David Cancel. The result of a phone call from Elias Torres ⚡️ a few weeks ago.

I'll sharing the full backstory + what I'm working on in my newsletter this week --> join at davegerhardt.com. Usually goes out Weds/Thurs.
Post image by Dave Gerhardt
There are 5 types of customers:

1. Most aware. These are the brand loyalists.

2. Product aware. They know you exist but they haven't bought from you yet.

3. Solution aware. They know there are solutions for their problem, but don't know you’re one of them.

4. Problem aware. They know they have a problem, but don’t know solutions exist.

5. Unaware. They don't realize they have a problem yet.

And they each require different messaging, content, and often strategy.

Another reason why marketing advice so often starts with “it depends.”
You can have a beautiful website and a great logo but no brand.

A brand is not your website. Or your logo. Or a witty tagline. “Building a brand“ doesn't mean “go hire a Creative Director.“

A brand creating a feeling. An attraction. Hey. These people are like me! Or Hey! These people get me.

Design is a piece of the puzzle -- a big one. But paint doesn't make a brand.

#marketing
You can't help the startup founder who doesn't believe in marketing.

Earlier this week I was in a conversation with a bunch of students at Harvard Business School - all startup founders.

Someone asked how to make the time for marketing + brand building as a busy startup founder.

No one asks how to make time for:

- Hiring
- Finance
- Investors
- Advisors
- Product strategy
- Customer development
- HR

You make time for marketing by committing to it and making it a core part of where you spend your time.

Might not have to be the CEO, but someone - one of the founders - has to be responsible for thinking about marketing.

Unless of course people are just going to magically hear about your business, get to know, like, and trust you, and then buy your product without any marketing :) more power to you
Any website I go to now this is all I think about 🍪
Atomic Habits, cold showers, and waking up before the sun is cool but have you ever started every morning with a screaming 3 year old in your room at 4:58 AM? That’s how I start my day on the path to success ✅

#marketing
#leadership
Don’t build a marketing team.

Build a media company for your niche.

#marketing
I don't want to be a billionaire. I don't really want to have dinner with billionaires.

I don't like traveling for work.

I don't like being away from my family.

I don't like meetings. I don't like networking. I'm not good at small talk.

I'd like to build a small, profitable business.

I'd like to be the anonymous rich guy at all of my kids school events and games and no one knows what I do or how I got there.

That sounds more appealing to me.

***

Follow me here Dave Gerhardt for more wealth building tips.

***

Edit: On the topic of dinner with billionaires ... Unless it was Jay-Z. I would take the dinner with Jay-Z vs. the $500k.
You'll be happier with the design if you write the copy first.
6 signs you might have a brand:

1. People actually wear (and ask for) your swag.

2. People proudly put your stickers on their laptops.

3. People *actually* reply to your marketing emails.

4. People email you for no reason just to say hey I like X thing you said/did.

5. People buy tickets to your event without knowing much about the agenda.

6. People want to meet your marketing team when they come to your office — just to say hi.

REMINDER: Brand is not direct response. It’s hard to measure with a spreadsheet. But it’s not hard to measure with your GUT. You’ll know it when you feel it.

Don’t be afraid to use your gut in marketing today. It’s a lost art.
I think way we train marketers/marketing teams is BROKEN.

We default to train people on technology first. Email. Social media. Landing pages. All the marketing automation stuff. AdWords. Facebook ads, etc.

What we SHOULD be doing is training marketers on PSYCHOLOGY first 🧠🧠🧠🧠

Understand what drives/motivates people -- and *then* layer on the tools & technology.

That's how I'd build the dream marketer.

Go and study:

- Social Psychology
- Cognitive Biases
- Go read: Influence, Thinking Fast & Slow, Predictably Irrational

*PS. I’m OK sharing this advice because I know that 99% of people will not actually go do it 🤷‍♂️ (that’s also how you can differentiate yourself — actually go put in the work & study).

#marketing
90% of the CMO job is hiring.

If you get the team right, everything else is easy.
Marketing is a battle of awareness and perception.

Timeless lesson from the book Positioning.
Post image by Dave Gerhardt
I don't think enough people know that one of the keys to brand awareness is repetition.

Busy people need to hear about you over, and over, and over, and over again (and then through a friend) before they think about your product.

And went most marketing teams want to take 3 months to do a new website. You pick the project but it's usually months.

Marketing is a momentum game. Speed matters. And you'll learn faster too.

#marketing
Who broke LinkedIn. I want a refund.

I have 150,470 followers here.

I wrote a post this morning and it has reached 362 people and 8 likes.

Apparently they changed their algorithm?

This is why you build an audience you own through email and other channels.
The most important tool in marketing today is in the sales team's budget.

It's true. Usually they're the ones that paid for Gong.

I think Gong is the most important tool for marketers in 2020+

It's not about some AI or automation or optimization or tech. It's about listening to the actual words coming out of your customers mouth -- from anywhere.

I haven't been listening to enough customers first-hand, so I put the Gong app on my home screen and listened to Privy calls today as a podcast replacement during my workout, in the car doing errands, and cleaning the house.

Some of the best learnings for website copy/messaging, product marketing, ideas for content, pressure testing your company story/pitch, handling objections all can come from those calls.

Robert Collier said “always enter the conversation already taking place in the customer's mind.“

Sometimes you just need to go and steal the words of your actual customers.

#marketing
You might not like it, but headlines and 15-30 second clips rule the world. Market accordingly.
There is so much power in the ability to write clearly and concisely.
New Privy website coming.
New Privy book coming.
New Privy bootcamp coming.
New Privy trials up 50% since Jan.

Current size of marketing team: 5

Haven’t seen each other since March 13.

❤️

#marketing
Spoiler alert: Everything in marketing works.

I've done over 300 hours of interviews with CMOs and VPs in B2B marketing. I spent a decade as a marketing leader myself (before officially become a thought leader) and I can tell you this one thing:

Everything in marketing works.

YouTube works. LinkedIn works. Direct mail works. Webinars work. TikTok works. Email works. Events work. PR works. Partnerships work. Heck, even spending $75k with Gartner can work.

But the challenge is figuring out which channels can work for you with the ingredients you have.

You don't always have the product, the features, the timing, the wind at your back, the talent on the team, the budget. But that is the fun part about the job in marketing - you get be the chef, but sometimes there's only two eggs, a slice of bread and an onion left in the fridge. Can you work with that?

The other thing that matters is the strategy. Why are you doing this. What are the goals, what is your POV on it, and how can you pull it off?

Too often we try to do everything - all those channels above - because we think we have to. And the result is another B2B YouTube channel with 30 videos that all have between 17 and 62 views. You'd be better off picking one channel and doing DEEP there and then finding ways to stack those wins into other channels.

This type of thinking has always been a guardrail on the teams I've been on:

- What's in it for me?
- Why should someone open this email?
- Why would someone actually take an hour out of their day and attend your webinar? Would *you* actually go to this webinar?
- Would you respond to that message?
- Would you see that ad and click on it?

And last thing - this is the hardest one. Often times GOOD MARKETING is not good for the company. That's right. It's harder to measure, takes time, not obvious, doesn't have UTM parameters in link; there might not be a direct response call to action. And that's what makes it good and makes it work, but you need to have the patience to trust it - and the ability to stand up in front of the CEO/CFO and articulate the marketing strategy and why you do things the way you do.

What did miss?

PS. If you are reading this and work in marketing, your job is to embrace this. Treat your job like a craft. Have conviction. Don't follow best practices. Use your brain. Be creative. Disrupt things inside of your company and push for a new way of doing things. More important now than ever when everyone has access to the Slop Machine ™️

We write about this stuff weekly at: exitfive.com/newsletter
Everybody wants to tell you how to do it.

And yet most have never done it.
It's 2020. Even if you have the best product, people won't believe it. Everyone is skeptical. Prove it. That's what marketing does. Build trust through content and prove it. 👊

#marketing
Quit your job if you’re not happy. They would lay you off so quick if they needed to. I talk to too many people who are so afraid of how it will look on the resume, what their boss will think - or they will leave after the completion of that big project in Q4. They don’t want to leave the company hanging. Etc. it’s always the same type of thinking.

But let’s be real:

They would lay your ass off so quick if they needed to. They’d feel bad about it. And they’d still do it. Because that’s just business.

There’s never anything wrong with looking out for yourself. That’s all you have anyone - yourself. A company of one. Go and make your new employer happy. They’d be lucky to have you.

I’m subtweeting a few friends that I’ve chatted with over the last two weeks of travel. It’s time to make the jump. There’s never going to be a right time to leave. You’ve got this.
Brand is all that matters right now.

One of the cool things about my job as the owner of Exit Five is I get to talk to CMOs and marketing leaders every week.

And the one place they are investing (and thinking deeply about) that’s not AI is BRAND.

This is: creative, events, mail, swag, out of home, and digging deep to re-connect with customers.

Because in a world where my AI agent is doing all of the research for buying things and presenting me a list of the top 2-3 vendors to pick, the last great differentiator just might be brand.

I picked them because well, I dunno. The AI said they have all the features I want. But I met their team at this event and they had awesome swag. It was a Nike golf hat that I’m actually going to wear.

Or the founder is actually a good person and kind and funny and authentic.

Some might call it taste, but that’s incredibly hard to define and we all have different taste. To some, the Olive Garden is the best Italian restaurant in the country. But if I ever brought Matthew Carnevale a bag of leftovers from the Garden I think he resign on the spot.

You know what I’m saying here?

Might be time to dust off the ol Guerilla Marketing playbook.

Stand out. Be different. Find new ways to connect with customers beyond “but did we show up in Perplexity search???”
YOU GUYS. Omg. I can’t believe it. Seriously.

200,000 followers on LinkedIn.

Started from the middle now we here!!!!

I came home today and my wife and kids had these balloons waiting for me because they know nothing means more to me in this world than how many followers I have on LinkedIn.

Thank you for your support over the years!

I’m going to ride this wave for as long as I can before AI takes my job.

I’m getting a lot of praise lately for being so “real” and “authentic” and my “writing style” just feels so “un-hinged” but this is just the cherry on top.

If you believe it, you can achieve it.

Thank you.

Especially to the moderators of LinkedIn Lunatics ❤️🫡
Post image by Dave Gerhardt
Weird growth tactic that is working well for us right now:

Focusing on quality.

We're not doing crazy things with AI. We don't have some secret growth hack or viral loop.

Our business is:

- A newsletter
- A podcast
- Webinars
- Events
- A private community

And I'd say the single biggest lever we've pulled in the last 12 months is a focus on quality.

This means:

- More prep calls with guests and speakers (yes, it works - putting in more effort up front)
- More editing cycles on newsletters and articles
- More prep work on webinar setup, run of show, event logistics
- Better research; deeper understanding of our audience and what people want

In a world where it's become incredibly easy to just blast out and AI generate email to 50,000 people on our list, we're going the opposite direction. Leaning in to everything before publishing. Better research. Better prep. Better guests. Pushing for less fluff and more specifics, real examples, metrics, stories from marketing professionals who actually did the work and had something on the line.

Don't let your lust for Claude get in the way of quality.
I am a huge believer that every touch point in marketing matters (if you want it to):

Things like:

- Replies back to newsletter
- Thank you page after signup
- The email you use to send out a webinar recording
- How you follow-up with guests after a podcast
- Your welcome emails
- Purchase emails, any type of subscription confirmation, renewals .. etc.
- 404 pages

All that stuff really does compound if you care about it.

But it doesn't often lead to a "number" so it's hard to quantify. And it’s not some cool AI workflow.
Your move LinkedIn. I know you all claim to hate X because of this reason or that, but they made the algo much much better over night.

Meanwhile my comment section is a who's who of AI slop.

I pay X ~$130/year subscription and they have an AI (Grok) that would be super useful on LinkedIn if it could search news and content in real-time.

I pay LinkedIn ~$1500/year subscription for Premium plus my company spends I dunno $250k in advertising each year...

I'm ready to be on the advisory board. I was not invited to Cannes this year despite having 201,000 followers here. Let's talk dave@exitfive.com
Post image by Dave Gerhardt
If the job of VP Marketing is to send outbound email and create endless ad variations, then yes.

Please. Replace the VP Marketing with AI.
Spent the last 7 days swimming all day with my kids. We had ice cream every night. Bike rides. Walks on the beach. I’m a 38 year old man but got to be a full blown kid on spring break with my kids.

The perfect reminder of what matters in this world. I didn’t use any Claude tokens this week either.

That’s the post.
That's a wrap. I have no voice and came home with some kind of flu, but after back to back nights of 12 hours of sleep, I'm ready to write my recap post.

My rating: it was a 10/10 week in Vermont with 400 B2B marketers for the annual Drive event from Exit Five.

*Maybe the flu is from shaking 348 of the 400 attendees hands, but it was worth it. I'll be OK.*

I am sure you've seen the flurry of posts here on LinkedIn.

It's not hyperbole: most are calling it the best event that exists for this audience, and we'll run it back here for 2027.

The whole premise of the event is connection.

First COVID sent most marketers jobs remote.

Then AI made it so you don't need to talk to a human.

YOU CAN JUST ONE SHOT THE WEBSITE WITH CLAUDE CODE, BRO WHY DO I NEED TO TALK TO HUMANS!?

But at Drive the room is filled with B2B marketers who are also Moms, Dads, knitters, CrossFitters, whatever the connection is beyond work. There were six people in the WhatsApp group that instantly connection because they had "Chilean spouses" at home. Not kidding. And that's just one example.

Where else can you be surrounded by people who actually get what you do for a living?

How do you get 400 people to a remote location in Vermont where there's no direct flights and the hotel is 1 hour from the nearest airport?

That's the power of community, and I'm convinced we need it now more than ever.

All of the credit in the world goes to the Exit Five team here. For the level of detail that goes into an event of this scale (making sure there's everything from WiFi to Oatmilk) but also the 12+ hour days that Anna, Ben, Marisa, Maria, Paige, Matt, Sheery put in on-site last week.

But the most flowers need to go Dan Murphy + Allison Saxon. That's the E5 events team, and they've been working on this one since Drive 2025 ended.

They deserve the credit; I just get to hold the mic.

Somehow they raised the bar once again. No outside agency or help in sight.

I met so many amazing people this week at Drive and re-connected with friends from over the years.

It really does go well beyond B2B marketing, bro.

Now back to my MacBook Pro and co-working space trying to chase this feeling until next year...

PS.

Events are very hard. Anyone who has put on an event for 20 or 200 or 2,000 people knows this. From the food choices to the run of show to the speakers, programming, lodging, recording sessions, how long the breaks should be - it is a true test in figuring out how to make everyone happy and you can never do it all.

We get great feedback every year and work to make each event better. We're doing an event in NYC next month, and our Leadership Retreat in March - we already have ideas and notes based on Drive last week, and I know Drive Year 4 will be better than 1,2,3 because of our ability to constantly improve. That's always the goal.


The Exit Five office is closed Monday, we'll be back open on Tuesday.
Post image by Dave Gerhardt
I feel empty inside.

That's what it is. It has finally hit me.

There is something soul sucking about being on video calls all day.

When I hang around people in-person there is a certain energy. I leave hanging out with friends, neighbors, parents with a GOOD feeling.

I am just a hopeless little knowledge worker in my house in Vermont talking into my MacBook Pro all day and there's no way we were meant to work this way.

Last week a few of the Exit Five team was in town and in a 45 minute car ride to the venue (we were seeing a space for our event) we solved like ... seven problems. And had some laughs.

Note: I also love being home, being around my kids, super lucky for the flexibility. But I am human can hold two different thoughts in my head at once.

I wish I was around the team more!! Playing music in the office. Getting around a whiteboard to draw something out quick.

Just sitting here in between meetings 2:55 PM ET going straight to LinkedIn to pour my heart out...
How To Run a Calm Marketing Organization (aka Why You Should Run Marketing Like The Product Team)

feat. Maria Scheifler

1. Stop saying yes to everything and build a backlog.

A backlog is just a prioritized list of work. Every campaign, every project, every random ask from sales sits in one place, ranked in order.

Most marketing teams operate from a mix of Slack messages, slide decks, Asana lists nobody updates, and whatever the CEO mentioned in standup last Tuesday. And then they wonder why everything feels chaotic.

Maria's point: when the head of sales walks over and says "we need a one-pager for this deal by Friday," your answer isn't yes and it isn't no. It's "we'll put it on the backlog and prioritize it against everything else we have going on."

2. Plan in two-week sprints, not annual marketing plans.

The annual marketing plan is mostly a fiction we all agree to participate in. Use it as your guiding principle for goals (but beyond that it's nearly impossible to plan for). You build it in November. By February, two competitors have launched something new, you lost your top sales rep, your CEO has a fresh idea from a podcast HE NEEDS YOU TO IMPLEMENT NOW… and half the plan is irrelevant.

Maria's argument: you still need a real strategy on a page. Goals, revenue targets, the big plays for the year. But the actual work should be planned in two-week chunks. Commit to what you're shipping in the next two weeks. Do a quick daily standup (10 minutes, what I did yesterday, what I'm doing today, what's blocked). Review the work at the end of the sprint and invite stakeholders in. Then do a retro.

She told me about running sprint reviews at her last public company. Twelve people, one hour, everyone presents what they shipped. Recorded. Shared across the org. Suddenly the "what does marketing actually do?" question stops getting asked. The receipts are right there in Slack.

3. Start finishing, stop starting.

Most marketing teams have 8, 10, 12 projects in motion at any given time. None close to done. Everyone is busy. Nothing ships. Or the stuff that ships doesn't move the needle.

Maria's lesson: start finishing things before you start new things. Kinda like how I make my kids clean up the kitchen before starting a new activity in the playroom.

Example: right now at Exit Five, our big campaign is selling tickets to Drive 2026. There's a ton of work that goes into that and the instinct is to wait until it's all ready before launching. Instead: what's the minimum viable thing you can ship right now that delivers value? We've sold 200 tickets and the full speaker lineup isn't even announced yet. Shrink it to the smallest thing you could ship and start getting feedback out in the wild.

If you work in B2B marketing and want a resource to help you with your job that's not an AI, get our weekly newsletter here:

https://lnkd.in/eG_RiSET
Post image by Dave Gerhardt
How do you get employees to write content on LinkedIn?

What tool do you use?

How do you incentivize them?

You can use a tool to get people to share copy and schedule posts and track impressions.

You can incentivize them

(Dan Murphy had this idea the Exit Five team is running right now called The Clout Cup you may be seeing everyone on the team posting lately over the last 8 weeks).

But I know the secret formula. It comes down to this:

Do people like their jobs? Are they having fun at work, learning, growing, feeling like a part of the team, winning together, and proud of the company they are at?

If so, they are approximately 37x* more likely to share content on social media. Because they are genuine, proud supporters of that company. I saw this at Drift. Everyone asked how we got everyone to post. We didn't get them to do anything, they wanted to. So when we asked more people to do it, they did it. And had fun doing so.

I'm seeing this again now at Exit Five... people are proud of the work they are doing here and having fun being on this team, so it's not "cringey" to post and share stuff on LinkedIn.

Have a great product / company / culture.

Employees will share and spread the word on social media.

That's the best marketing you could do.

*37x is my stat, completely made up. But I am a feel player and I'm confident in this number. Not approved by Gartner, Forrester, or Sirius Decisions.
Here's how to do great marketing for any company in any industry.

I've recorded nearly 400 conversations with VPs CMOs and subject matter experts all around B2B marketing the last 4 years working on Exit Five.

That's something like 24,000 minutes spent talking with people who earn their living and have made careers in this industry.

Want to know the number one lesson I've learned?

This is not hyperbole.

The number one thing I have learned is that there is no playbook.


There is no recipe. Despite what you read online about how this person took this one company from $0 to $100M in revenue, or how Canva did this or Figma did that or Loom did this without a sales team or HubSpot had this thing with churn early on.

There is no playbook because (gulp) everything works. LinkedIn works. TikTok works. Direct mail works. Events work. Outbound works.

But also everything doesn't work - for the same company that thought Dreamforce was great and worth the $50k for a booth, another company said it was a huge waste of money.

For one company that said going up market and shifting to enterprise was the right move, another one didn't get the formula right and couldn't make it work.

There is so much nuance in marketing because you're relying on so many factors you don't control: the market, competition, budget, who you can hire (ex: everyone says "hire A players" but what if you can't? what if no one knows who you are, you don't have a big budget to pay top dollars for the former Salesforce exec. How can you compete with the talent Anthropic is paying for right now?) Each industry has a different core buyer and that changes what might "work" in marketing to them.

Some industries have different rules/laws/regulations/.

You get the point...

So the best thing you can do (based on my 400+ conversations is this):

Realize this is the job in marketing. And this is what makes it fun.

As Jay-Z said: put me anywhere on God's green earth, I could triple my worth.

Take that approach to marketing. Whatever the ingredients you're giving me - I will make it work. And I know that it will be different at each company and industry. But the game is finding some of the overlap, being able to pattern match. Understand people and how they make decisions. And being able to think outside of the box and not rely on a playbook.

Take each company, product, industry on it's own and figure out how to reach and influence people there.

That is how you can do good marketing for any company, in and industry.
I’m old enough to remember having to use my brain at work!

I know. AI is this amazingly productive technology. But man so much of what makes for great marketing (and business) comes from a feeling, a vibe, taste, intuition, gut.

And maybe I’m using it on the wrong settings but my ChatGPT and Claude are kinda big dorks in those areas.

Don’t forget the power of thinking for yourself.

Hand writing a note. Sending a one off video. Do something that doesn’t fit neatly into a spreadsheet.

That’s where all the good stuff happens.

PS. Yes, I’m turning into a boomer. But Claude was down yesterday and our team was freaking out and I came down from my Tower and yelled at everyone get off my lawn!!!
You know what is incredibly hard to do? Run a great business.

I don't think I appreciated it until starting my company, but I look at every business differently now - from the breakfast place down the street to ordering a new piece of gym equipment to an enterprise cyber security company.

It is freaking HARD to hire the right people, train, build a culture, find product market fit, set the right expectations, be able to service customers in the right way, handle feedback, change the menu, raise prices, keep the lights on, organize the books, figure out how to pay and get paid, taxes IT IS A LOT and then you have to find ways to stay relevant with AI, stay up to speed on AI, all the things.

To build a reliable product/service is no small feat.

And I think my business is relatively simple and easy to operate.

Much respect to the Founders and Business Owners.

The past 4 years running Exit Five has shed light on so many things I did not see before.

It's kind of like being a parent. Once you have a kid you realize why your parents did things the way they did.
When all the comments are AI…
And all the reviews about your product are good
The images are perfect
There’s not a flaw in sight …
What happens?

How do you do marketing in that world? Who do you believe and trust?

I open up Uber Eats (not here in Vermont because it doesn’t work here, but when I’m in a city) and the restaurant photos and food pics are all stock images.

That’s not what the food looks like. I want the real pictures. I want to know it’s real.

Unless you believe (and think life will be better) if AI does all of our buying and thinking?

There will always be a place for realness. For trust. For authenticity.

Use it to your advantage.
One thing I learned over the last three years: it is way more fun to win as a team.

When you're solo, who do you celebrate with?

I was on LinkedIn for years pumping the benefits of being a solopreneur.

I was my own boss! The hours were great! The flexibility! No drama! I can solve any problem myself!

But what I missed (and didn't realize until Dan joined and we starting building a team at Exit Five) was being around other people.

I think we were meant to work together, to collaborate, to solve problems together.

To not have to figure out the answer to everything ... alone.

To be able to work through challenges and get new ideas from other people.

But also because it's fun to do the work together and be able to make jokes, be silly, having a culture, inside jokes ... and doing it our way not some corporate way.

Working on Exit Five has helped me see that there is not one way to do it. Just because they do it that way at Salesforce or some PE Guy says you need to sweat this benchmark or this ratio.

It's also incredibly rewarding to see teammates make a name for themselves at Exit Five and get money, status, and future career opportunities from being part of this team.

That's the part I did not expect at all.

So yes. Guilty. I changed my mind. It's great to be on a team.

Take that Claude.
I spent the entire weekend in Claude Code.

As a 38 year old man. With a wife. Kids. Lots of things going on.

But I spent the entire weekend in Claude Code.

Now, my wife is pissed. Says I was not present all weekend.

My kids - they were home, but I just ignored them and hid on my laptop in the other room.

But at the least the Exit Five webinar emails will now be 5x more efficient to create!

Marketing, baby.
OK. I've been feeling super burnt out lately.

Not with work, but with AI.

I know it's incredible. But I am burnt out.

Too much time in all the AI tools. Too much time scrolling social media seeing the FOMO about this new skill vs that.

Gemini. ChatGPT. Codex. Claude. Claude Code. Claude Cowork. Cursor. How to automate your entire life. Why are you not doing this yet? How inefficient am I not mastering all these tools to run my life? My business?

And then the best thing happened.

One of my favorite artists J. Cole put out his "final" album The Falloff and this week he's been driving around his hometown in a Honda Civic and selling CDs out of the trunk.

In a world of fakes (or worse, your previous former favorite rapper hanging out on Epstein Island) this guy continues to be a breath of fresh air because he is real.

J Cole is actually famous for his lack of "flexing" - imagine that. He's not into fancy cars, jewelry, living a lavish live. He likes to make music, workout, play basketball, and connect with people on a real level. Hanging out at the mall in his hometown.

In a world where male role models seem to be ... vanishing by the month. I like this guy! This is a good trend!

Now I'm just wondering: how is everyone even going to play the CDs they are buying?? Who has a working CD player? Maybe that's why he kept the Honda Civic around...

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