Hey, A-A-Ron here! Welcome to this (typically) twice-a-month startup newsletter. In each write-up, I tackle questions about building products, financial planning, growth, and raising capital! Today we dive into -

(un)conventional Update:

I’m reactivating YouTube, LinkedIn, and more!

It’s been a long time coming… but I’m back online with regular content! The goal is simple: create an ongoing stream of high-quality educational content available on various platforms to reach founders of all industries and business models. I’m excited about the future, and I hope these posts and videos can benefit other founders with the lessons I’ve learned from building and advising startups for the last 5+ years.

To kick off this endeavor, I will be focusing on YouTube, LinkedIn, Instagram, and TikTok for as long as it sticks around. I’m also in the process of updating our Skool community (an update on that is coming next month!), which will offer a more direct line to me, plus access to resources and other startup education.

Opinion:

Most Founders Are Too Confident

I know how it sounds, but hear me out! I promise it comes from a place of love… and reality. I work with founders of all stages, and I’ve had the bittersweet experience of seeing immense successes and really tough failures. And both sides of the coin have lessons we can learn from.

Something I learned early on that still persists to this day is that founders who approach their business with a sense of “humble confidence” tend to make the most progress. “Humble confidence” loosely translates to: be confident when you’ve earned confidence, and until then, be humble.

The purest examples are founders who believe their product is exactly what the market needs and it’s easily going to be worth $1 billion so they want to raise a 7-figure pre-seed capital round. These are the same founders who have neglected to do even 10 worthwhile customer interviews, haven’t incorporated their company because it “costs a lot of money,” and don’t ask their friends and family for early capital because they fear turning the relationship sour if it fails.

Let’s call it Schrodinger’s Confidence - a founder is only confident until they have to put that confidence on the line. If you test for confidence, there is none… and if you don’t test for it, they still have it.

The way to overcome this is not going to come as a surprise to anyone: you have to do the work. It’s hard to lack confidence when you’ve spoken to hundreds of potential customers or have consistent waitlist sign-ups coming in due to your organic sales and marketing efforts.

I want to encourage as many of these real founders as possible because the world needs more people willing to do the work. So, if you know a founder who’s being a little too confident lately versus what they can actually support, encourage them to get to work and do the things that will allow both them and their business to flourish.

Notable News

Cool Tool:

The Best To-Do List Ever (Category: Operations)

Managing operations is a pain. As someone with ADHD, I feel like I’m especially frustrated with this area of owning a business because of the volume of never-ending, daily tasks.

A few years back, I had a major breakthrough in this department when I was chatting with another founder late into the night at a coworking space. We started talking about what tools we were using to manage our businesses, and he recommended I check out Todoist. He said it was the best to-do list he’d ever used and would be surprised if I felt differently.

5 years later and he’s still right. If you’re tired of losing your written list or have your to-do lists scattered everywhere, I’d recommend checking Todoist out. Hopefully it helps you get more done, too!

That’s It For Today!

Consulting || Resources || Community

Written By Aaron @(un)conventional Team