#131 (Great) Pitches Get Riches

Welcoming you back with a conversation I had yesterday after a morning jog with my dog.

The apartment complex where I live was re-paving the parking lot. When the time came, three cars were still in their spots (despite the fact there were signs every ten feet saying to move by 7:00am, but I digress…)

As we were returning from our jog, one of the paving crew asked me, “Do you know these people? If they don’t move these cars within the next half hour, it’s a $300 fine and a tow.”

I answered his question but didn’t let the conversation end there. I asked about the project and cringed at the thought of waking up to a $300 fine. He laughed.

Eventually, he said, “You know, I asked another guy if he knew whose cars they were about fifteen minutes ago, and you should’ve seen the look he gave me. Like I ruined his morning by asking.”

He went on: “It’s crazy. The sun is out, it’s a beautiful day - how are you in that bad a mood that you’re annoyed by a simple question. Life’s too short to be that upset first thing in the morning. I started work at six this morning. I could be in a bad mood, too, but I’m grateful to be outside today.”

That’s what stuck with me: the crew member’s gratitude for the day and life overall. That’s the right perspective.

Obviously, we don’t know what’s going on in the life of the Mystery Annoyed Guy, but for me, no matter what’s going on, no matter how stressed I get at work or with the wedding or anything else that may come, gratitude remains the choice.

I woke up today. Life is short. The day is beautiful.

Take in the beauty and reset…

Flying Into August With…

• The Search Bar: Exploding Topics, Trending Stocks, New AI Tools 📈 💰️🚀

• Say It Better: Get Better at Pitching Yourself 📈 💰️

• Hustle Hub feat. Level Up Your Brain and Become More Consistent 📈 💰️🚀

• OTF Trivia Quote of the Week: 📈 💰️

• August’s 2-DO LIST: Work on Your Pitch & Remember Names 📈 

THE SEARCH BAR 🔎

What’s Trending Heading into August 2025

• Exploding Topics - As always, you can’t go wrong with browsing the site, but to kick off August, let’s take a look back at the hottest July trends. The post begins with a long list of terms / products, but if you scroll past, you’ll get brief descriptions of ten main things to keep an eye on. Absolutely worth a click, whether you’re coming at it from an entrepreneur’s or consumer’s perspective.

• Top Trending Stocks (as of 8/4 at 6:15pm) - The markets had a good day Monday. Here are the top trenders, courtesy of Yahoo Finance (with the markets’ overall growth on the right):

• 10 “New” AI Tools - Instead of our usual apps section, let’s get a jump on next week’s Productivity Edition with ten AI tools launched this year:

(Jake Dawson has over 40K subs, and this particular video has over 14K views since upload.)

HUSTLE HUB 📈

YOUR SUCCESS:

Be Smarter - Anyone who reads OTF is already pretty damn smart, but if you want to be even smarter, here are five steps to take your brain to the next level.

THEIR SUCCESS:

Be Inspired - From side-hustle to super successful, this dude turned a teenage gig into millions!

YOUR SUCCESS:

Be Consistent - Here’s how you can use the “2-Week Rule” to reach your biggest goals.

OTF-Trivia Quote of The Week ✍️ 

Instead of trivia, I wanted to share this quote from one of my all-time favorite books, How To Win Friends and Influence People.

Takeaway?

If you become the person who remembers names, it’ll set you apart in the best way possible.

SAY IT BETTER 💯 

A Creative Framework to Pitch Yourself…To Anyone!

Pitching yourself - elevator-pitch style, who you are, what you do, etc. - is HARD AF! But maybe after digesting a bit of Modern Wisdom, it’ll get easier.

That’s the name of a podcast, by the way, hosted by Chris Williamson. I was listening to an episode the other day with guest Daniel Priestly, a successful entrepreneur in the digital space. Daniel (great name, btw) said something so lethal regarding pitching yourself that I had to share it.

He suggests using this framework.

• Name

• Same

• Fame

• Aim

• Game

Let’s look at these real quick before passing it off to our resident Professor (who’s been teaching rhetoric for more than a decade).

• Name: I’m confident you got this one 🤣

• Same: How can you put what you do in a way that people understand? It can be a comparison to something obvious or simply an explanation that allows everyone to be on the same page.

• Fame: What makes you unique? Any big numbers? Awards? A milestone-level of experience? Essentially any detail that raises you up from whatever to WOW.

• Aim: What are you working toward in the short term? Think about the next 90 days. People are curious and want to know the tea. Share something.

• Game: What’s the long game? Where are you heading in the next 3-5 years?

To bring this home, here’s a sample that I just whipped up:

• My name is Dan Healy. I am an underwriter for a global insurance company. I’ve been there for ten years. I’ve worked in New York City, LA, and now New Jersey. I also write a newsletter called On The Fly, where I talk about the intersection of business and communication. I’ve researched, written, and published for the last 131 weeks straight. I’m aiming to grow the newsletter to 5,000 subscribers by 2026. Over the next few years, I plan to grow my online presence and foster a community of people who want more for themselves. I am also working on creating digital products to help professionals future-proof their skills in business.

Prof Mike, you’re up…

I’ll start by saying I like the framework. I think Daniel P. is onto something.

Now, about Daniel H’s sample pitch…I think it’s solid. Let’s break it down:

Name: Yes, that’s your name. So far, so good.

Same: I like the use of the word “global” there. The “insurance company” part is what everyone can understand (do people know what underwriters do?), but the “global” takes it up a notch.

Fame: I think “milestone-level experience” is always good. Persuasion requires establishing credibility, and experience is great for that. However, I don’t find the list of cities / states all that interesting, especially because NY and NJ are pretty much the same market. Three different countries? Sure. But NY / LA is kinda cliche to me (no offense).

A big key here is choosing the right detail, and that requires knowing your audience and basing your choice on them.

Writing OTF qualifies as interesting, I think, though reasonable minds may disagree. The detail that got my attention was “131 weeks straight.” You could’ve worded this other ways - over two years, for one - but that number stands out. Nicely done.

Aim: Would people need to know how many subs you already have to truly understand your aim? Getting to 5,000 over the next four months is a lot different if you’re at 38 compared to 3,800.

The goal here is to sell yourself, which means you want to share info (at every stage of the framework) that lets people draw positive conclusions about you. They can’t draw any conclusion without current subs because they won’t know if your goal is ambitious or manageable, underwhelming or reasonable, etc.

Game: If you were my student, I’d advise you to be MUCH more specific. This is your last chance to leave an impression. Don’t blow it by being vague.

First thing I’d do is adjust the language of “I plan to” to sound more assertive and confident, and then I’d follow with specific details to make your vision clear. “Grow my online presence” on what platforms? “Foster a community of people who want more for themselves.” What does that even mean, and is this the same point as the “online presence” or something different? “Working on creating digital products” — “working on” sounds like you’re not really doing it, and what sorts of digital products?

Specificity would make this more memorable and make YOU seem more impressive.

Heard, Prof, heard.

2-DO LIST 💡 

AUGUST 2025

1. Practice Your Pitch - I challenge you to do this in under ten sentences. It won’t take long, and it’s a fun exercise!
   

2. Remember Names - That quote from earlier rings so true for me. I meet a lot of people, and I’ll admit, I forget names at times. I’m going to make a conscious effort moving forward to remember them, and I challenge you to do the same. If you need a trick to make it easier, here you go.

Before You Go!

Thanks again for joining us! Next week, we’ll be back with August’s Productivity Issue.

For new subscribers, these editions tend to focus on AI and how we can use it to our advantage both personally and professionally. But there’s always a sprinkle of good old-fashioned productivity hacks, too.

As always, see you next Tuesday 🤝 

Find Dan on LinkedIn

You are now On The Fly & In The Know.