Only posted once in 3 weeks. I've lurked though. I've contemplated quitting.. It's been 3-4 years of posting on average 2x/day. Here are random thoughts I've had in those 3 weeks: 

- Linkedin is getting weirds, for better or worse
- People are chasing any kind of attention, even negative
- Claude code + Cursor combo can build most things you pay too much for 
- Agencies are hot right now, but unsure about the shelf life 
- GTM tech is screwed
- Things are much bigger than work but being consumed by linkedin makes you feel otherwise
- Babies are resilient (had a massive scare in costa rica resulting in 4 doctor visits & advice to fly home immediately)
- Too many people take things too serious
- Enterprise sales is the place to be for stability - get there immediately
- Consistent hard work will always come out on top 
- People are extremely selfish and it's sad 
- If you're okay with being on camera, create short form content immediately and spread your message on all channels 
- Conflicting to my selfish post - people are also extremely beautiful and nurturing 
- Learning other cultures should be a priority for anyone
- If you don't life weights now and you're 30 (assuming you're physically capable) you'll regret not gaining muscle mass in 5 years 
- I hate the Bears, but they actually have a decent team 


I'm sure I've had a lot more thoughts, but there's a brain dump for you. 

Get ready LinkedIn, I'm coming in hot. 

Best sales content you've ever seen from me is on the way.

Troy Munson

CEO @ Dimmo

5 years ago I bought my first home. 

3 months later, I got a new job. 

I got an offer that was $60K more on my base. 

I took it despite being at 135% of my number at my previous company because of stability and a new mortgage.  

12 months later, I hit 30% of my quota. 

Was selling a large enterprise product to mid market accounts - didn't work well.

Made much less than I would’ve if I stayed at the previous company.

Also, if I stayed the full 4 years at my previous company, my stock would be worth almost 7 figures today.

It's my biggest career regret.

On top of all of that, my mental health was in the drain because of the money and inability to close consistently..

So I looked at companies here: https://lnkd.in/dc2GcVp2 and joined the top rated company at the time. 

In 3 quarters I hit my annual quota and worked with the best people I've ever met. 

I literally had the most fun I've ever had at a job because when I looked at these (https://lnkd.in/dykkEGgc) I made a promise I'd only join a company that:
- had good quota attainment
- a healthy culture
- good product market fit
- and good leadership

do NOT do the same thing I did and leave for money. 

Grass isn't always greener.

Brand partnership • CEO @ Dimmo

The largest deal I closed? $930,000 when I was a Large Enterprise AE at Proofpoint. Customer was in the hospitality industry. Random things to know about the deal: 

- I thought I lost the deal because they went quiet for 2 months
- 15+ people involved on their side
- Executive alignment all the way up to our CRO
- Came from an outbound email 
- Took over 11 months from start to close 
- I got my leadership involved early to increase my chances of winning
- I really leaned in on the people that DIDN'T want our solution and made them neutral OR positive
- They tried to haggle me down to $600k (our competitors price)
- I doubled down on where our competitor couldnt meet their requirements 
- I stalked a Digital Sales Room every single day to see who was doing what
- I texted with my champion and procurement every day at the end
- I closed the deal while drinking a Pina Colada in the Dominican Republic on Dec 30th, about the last day of the year. 
- I bit my nails so short because of how anxious I was 
- I lost sleep many nights over this deal 
- This deal allowed me pay off my cars and student loans
- I learned that you need to slow things down when you're moving too fast
- I told them to stop evaluating us if the competitor was still in the conversation, they doubled down on the evaluation
- When you have a technical win, you barely need to discount. Only discount for time incentives and legal paper incentives. 


There's a lot more random thoughts, but here's what I'm thinking about in this moment.

I didn't want to post about this. 

Because everyone and their mom is. 

But I'm also one of those that switched everything over from ChatGPT to Claude and Gemini. 

Everything. 

Summaries. Analyzing transcripts. Capturing data. Cleaning lists. 

You name it. 

It's simply just better. 

And doesn't gaslight the hell out of you.

I've spent my career closing deals from 50k-$1m (sadly nothing bigger). Here are 4 things you want to get from EVERY first call:

1. What's going on? 
2. Who in the company is saying it needs to change? 
3. What's the cost of not changing? 
4. Why does it need to change now? 

Of course, there are hundreds of questions to get these answers and many other questions to dig deeper. 

But if you can get this info on call one, you'll be able to qualify deals in/out much better and not waste time on chasing air.

Took a much needed break. 

Comeback loading...

Not-so-fun truth about sales below (8 of them)

add your truth in the comments: 


1. Timing is a big part of selling into new logo accounts. If they just went with a competitor two months ago, your timing is off for another ~8 months. Doesn't mean you can't start building a relationship.

2. Your territory and accounts will change frequently. You could lose a top account that you’ve been prospecting into for years only for a new rep to break into it within a month due to your efforts.

3. You can work harder than others and they can still get luckier with inbounds and have a better year than you.

4. Your prospect doesn’t care about you at all. They don’t care if you hit your quota. They don’t care if you lose your job. You’re a stranger until you make an impact.

5. Your territory might suck. You can either complain or double down and do what you can. Control the controllable.

6. Good chance that your quota might not be attainable. Especially true for companies that got tons of funding 2020-‘22. That’s why quota attainment rates are so low right now.

7. Your OTE means nothing if you hit 30%. It’s easy to fall into the “big OTE” trap.

8. You can do everything right and still miss quota. Chances are, management will notice you’re doing the right things. Good management will have your back and help you out.

My 3-year-old called me out for biting my nails.

Right after I told him to stop...

That's when I realized kids are sponges. 

So we talk about the importance of being intentional around your kids on today's episode of TDIT. We also talk about:

- Parenting four boys (ages 5, 7, 10, 12)
- Managing chaotic mornings with multiple kids
- Marriage requiring active work vs. complacency
- Feeling behind in fitness, family, and work simultaneously
- Kids holding parents accountable for their behavior
- Using inadequacy as fuel for motivation
- Breaking negative patterns from your own upbringing
- Keeping a private journal to document moments with kids

Go give it a listen: 
Apple: https://lnkd.in/dgvVBuTi
Spotify: https://lnkd.in/dngAnKpe
Watch: https://lnkd.in/dWXGgGCR

me: I have a headache 

ChatGPT: “Troy, that's amazing! Having a headache means that you still have a heartbeat and that you're still breathing, which is a beautiful thing to experience! What an amazing time for you. I'm really proud of you for being able to speak up about it and having the courage to let me know”…

I don’t want to put you on blast.. 

But if you’re a sales leader / revenue leader that is unhappy with your current contact database / sales engagement tool. 

DM me. 

We don’t need to hop on a call. 

I’ve done over 50+ one-hour tech stack reviews to where I can tell you the best alternative immediately. 

Just tell me what you use, the main problem, and I’ll point you to the best solution. 

That’s it. 

Zero strings attached. 

See you in the messages 👋

I feel behind in my fitness. 

Behind with my family. 

Behind with my work. 

Every. Single. Day.

That's what Brendan Hufford told me when I asked where he feels like he's falling short.

And honestly? 

Same.

Brendan joined us on the TDIT podcast to talk about:
- Managing life with 4 boys
- How to work on your marriage
- Feeling of always feeling behind
- Breaking negative patterns from upbringing
- Keeping a private dad journal
- Single mom's work ethic impact
- Teacher to tech career transition
- Therapy changing perspective on drive

This convo got deep. 

In a good way. 

Listen: 
Apple: https://lnkd.in/dgvVBuTi
Spotify: https://lnkd.in/dngAnKpe
Watch: https://lnkd.in/dWXGgGCR

I've done enterprise prospecting training for 14 companies. Here's one tactic that works like a charm: 

ps - this works REALLY well for a bottoms up approach.

For starters, this message (pictured) was targeting information security titles - a title not typically talked about on LinkedIn. 

So, if your company has ANYTHING of value, position it as a "nice to have". No pitch, no nothing. 

For example: 
- A sales tool that has a bench mark of cold call openers
- A marketing tool that has a report on ad spend
- An IT tool that has an article on saving cloud costs 

Use that to start a conversation. 

Examples: 
1. Sales Tool: "Hey Troy, not sure if you're ramping up cold calling but can I send you over the 3 cold call openers that have been working well for me?"

2. Marketing Tool: "Hey Troy, see you're running a handful of LinkedIn ads, can I share the the highest performing picture format we're seeing for Cybersecurity companies?" 

3. IT Cloud Tool: "Hey Troy, mind if I share an article on the 10 ways you can reduce cloud spend in 1 hour?" 

When they respond you can do two things: 

1. Send them the information, then follow up the next day. 
2. Ask for a bit more details. 

More details example: 
Marketing Tool: "Great, let me send it over, what else should I send over that can help with your LinkedIn ads? I've got many helpful resources"

Them: "Have anything on optimizing campaigns?" 

**THIS IS A PAIN POINT - THEIR ADS AREN'T PERFORMING AS WELL AS THEY'D LIKE. WASTING SPEND & NOT GENERATING ENOUGH PIPE**

Anywho, not sure if this was helpful at all. 

But give it a shot.

I’ve built 4 startups and sold 2. Raised $800k+ for one of them. It's easier than ever to do this now. Here's 7 steps to get going:
 
Step 1: Talk about the problem everywhere
- Before you build anything, start talking about the idea. 
- Post about the problem on LinkedIn, Twitter, Reddit.. wherever your audience lives.
- If people aren't engaging with the problem, they won't pay for the solution.

ps - publicly build on TikTok/Reels. Tell a story in every video. Chances of virality are actually pretty good. 

Step 2: Build your ICP list
- Create a spreadsheet of every potential customer.
- Be specific: job titles, companies, industries.
- Use free trials of tools to find their emails and phone numbers.

This is your goldmine / north star.

Step 3: Turn your idea into reality in hours
- I use Replit for all things re: building an idea
- It's not 2024 anymore, you can use AI assisted tools like Replit to build an MVP
- Spend a few hours making it demo-worthy.
- Something real > something perfect.

Step 4: Set up a landing page
- Create a simple page that explains the problem and collects emails.
- Use Carrd, Webflow, or even a Google Form.
- Every warm lead from your outreach should land here.
- This is your early waitlist.

Funnel everyone to this landing page from all socials.

Step 5: Start outbound immediately
- Email your ICP list with clear, problem-focused copy.
- No fluff. Just: "Here's the problem. Here's the solution. Want to see it?"
- Pay for one month of a contact database if you need to scale fast.
- Book meetings.

Step 6: Charge from day one
- Your first customers must pay. Even if it's $50. Even if it's imperfect. Free users don't give real feedback. Paying customers do.

Revenue = validation.

Step 7: Use traction to raise capital

Now you have:
- Paying customers
- A waitlist
- A (kind of) working product
- Proof of demand

This is what angels and VCs want to see.

You're not pitching an idea anymore, you're pitching momentum.

Just like that, you've now started a company.

If you’re reading this, chances are 2026 should be your year of under thinking.

taplio

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