Welcome back!

The new and improved On The Fly is here! I started this edition bright and early on Saturday 8/29.

Anyway, the last 3 months have been absolutely INSANE.

And I feel like the game hasn’t started until now.

IT’S NOT ME… IT’S YOU

While this edition focuses on me, it's really about you because I believe a lot of people who start a company, gatekeep.

It often seems when building a company, not enough is shared of what’s going on behind the scenes to give you insights into how it all works, or what’s going well and what’s sucking or really anything to help you in your aspirations and endeavours.

Quick reminder if you missed the email 2 weeks ago: this is a space for aspiring and current entrepreneurs — and if that's not your speed but you're still curious, please stick around, I'd love to have you!! I'll be sharing the good and the ugly of building a company as a one-man show, so you can use my lessons as guardrails for whatever you're building.

With this week’s edition, I’m sharing the raw & unfiltered pros and cons of ~3 months into starting my own thing.

Time for take off!

THE CONS (SO FAR)

“Alexa: play the first 20 seconds of Glamorous by Fergie”

Not having bi-weeklies just sucks. Not sure how else to put it.

Consistently receiving X amount of dollars every two weeks felt so comforting in hindsight and I felt superhuman. Go out to dinner randomly? Sure why not. Drive north and travel for 3 days, let's go do it. You don't realize how helpful it is to know you can spend $$ b/c you know you're getting more in a week or two.

But now that I don’t have this luxury, the saying is so true as I write this: you don’t know what you got til it’s gone.

Emergency Fun(d)?

While I’ve gotten used to not receiving those precious checks, what also sucks is taking money out of my emergency fund for the last 3 months.

Like me and my wife planned out what amount we needed to hit in order for me to make the jump. We got 98% there and then I was like okay screw it, I’m doing this.

Side note if you're sitting there waiting to hit your own number: I'm not sure you ever feel 100% ready. 98% was enough for me and I'd do it again.

But having the money bleed out from the account stings more than when me and my wife get bit by these green-headed flies that swarm around our neighborhood when we go for a walk during the day.

The sting should simmer as I get clients and the business grows, but seeing the bleed out hasn’t been ideal for the eye.

Hmmmnn, what else sucks…btw I’m not a cynical person, I’m just being real with you.

Alllllllllllll Byyyyyyy Myyyyyyyself 🎶

This is a big one. The people I don’t work with anymore.

I work with my wife and my dog. I won’t say they suck lol, but when you first start as a one-man show like I am, you don’t have someone always working with you like I had in the office.

A thing I didn’t take for granted in my corporate career, but quickly realized how important it is for your psyche – working with people is a damn good thing. Like just to be able to talk with someone on the floor is underrated. It’s healthy for you.

It can’t just be you and your AI at work you know? And when you lose out on the random jokes, happy hour memories or venting about some dumb company email that went out, it really makes you appreciate the importance of working with other people on a daily basis.

Health Insurance > The NY Jets

Last but not least, health insurance, this sucks more than the NY Jets at the moment (and I’m a Jet fan).

My health insurance was roughly $163 a month when I worked at Chubb. So call it $80 per bi-weekly. I elected COBRA when I left the company and now I pay $789 per month to continue the same dental, vision, and medical I had until 2028. This amount stings [maybe] more than both the emergency fund bleed and those damn flies.

But it’s all good, it’s what it is. Some business owners don't pay for health insurance which [to each their own] is just dumb, but I felt obligated – I mean I worked in the industry for 10 years, it wouldn’t look good if I tried to dodge this expense.

I’m giving you context because starting your own business isn’t pretty early on, but I’m confident things will turn. You just have to trust the process.

Now, let’s turn the tide.

THE PROS BABY, THE PROS!

No moe sunday scaries

There’s this feeling where you wake up and say holy sh!t, it's literally up to me to figure out what to do and how to do it and for some odd reason that jacks me up. I guess I’m lucky in that sense, but there’s nothing I’d rather be doing than going after it on my own terms.

Weight on shoulders = see ya!

I started this newsletter and put out other content 3 years ago alongside my career.

There was always this subtle feeling of being filtered because I’d feel this weird feeling of judgement or think that senior management is like, okay what’s this guy actually trying to do with what he’s working on and sharing publicly online???

Now that I’m on my own, that feeling is so far removed where there is this giant weight off my shoulders and I can really express who I am and how I want to work.

Planet Fitness = My social outing

My wife and I have been making the effort to go to our local Planet Fitness 4-5 times a week and it’s actually been really fun. Starting to get my macho strength back.

It’s nice to see what’s become some familiar faces behind the desk each morning and my wife and I have really pushed each other to new fitness goals.

Plus, not having to commute a total of 3 hours a day has allowed me to focus more on my physical health and my diet, which has been a dang good feeling.

Btw — paying $15 a month helps the budget b/c you know, the emergency fund is bleeding.

Building everything in Claude has been game-changing.

I will get more into this in future editions, but the entire company is built in Claude. The workflows I have set up helps me save so much time it’s truly wild.

For example: you must create what’s called a “context file” that you upload into Claude for example. This context file should explain everything about the project you’re working on. If it is not clearly defined, you will be wasting so much time using the tool. I’ll dive deeper into this another day.

I’m not some tech guy either, like I worked in insurance for 10 years. I learned everything by doing and I’m highly confident you can too. I’m excited to share how I got here so you can take what you see fit and run with it!!

Thank you from the bottom of my heart for your support! I value it deeply and I can’t stress that enough.

If even one person gains inspiration from what I have to say within this newsletter, then I’ll consider that a W.

Doors always open to ask questions…PLEASE feel free to DM or email me anything, even if it’s to learn a quick tip about AI or talk about whether this will finally be the year the Jets turn it around and win the Super Bowl.

See you next Tuesday.

To building together,

Dan

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