The biggest early mistake this entrepreneur made

Hi everyone. This week, a new Thought Liters went live. I featured Jordan Herbert, founder of DealMate. Topics below — here’s the vid if you’re interested:

This episode was a little different as we opted for a flight of local craft as opposed to a single featured pour. Because hey, if this is supposed to emulate Hot Ones, it’s gotta at least look and feel similar, right??

We “poured” over the following topics:

• Jordan’s journey to founding DealMate, including the early days of his come-up in traditional sales (cars and Cutco)

• How to thoughtfully balance running a business and being there for your family (helpful for any new parent)

• Jordan’s biggest early mistake in entrepreneurship (more on that below)

• How to stay resilient in the face of sour business

• Advice for the entrepreneurs of tomorrow

(If you’ve read this far, thank you + I’d really love to know what you thought of the episode. Feedback is something I’m kinda lacking right now and I’d rather build this show based on what people actually want!)

During the show, I asked Jordan to talk about an early mistake he made in his career, and his learnings from it (in a segment I might continue called “I Remember My First Beer”). Jordan’s answer was surprising — in short, he answered me with a quote:

We all know the phrase “the grass is always greener on the other side” — the situations of others often seem better than your own. Jordan reflects on that phrase as the root of every early big mistake he made in his career, including entrepreneurship. In exchange, he offered the above corollary to suggest that the best situations appear where you put in the time and effort.

Look, I’m a self-admitted grass watcher. I’m guilty of it all the time — I watch my fellow Harvard grads rake in huge funding rounds, exits, and senior titles, and lament my seemingly relatively shitty little content operation. Not that I need Jordan to tell me that’s a mistake — but it was a poignant reminder to appreciate my own grass, and just keep watering it. Someday it’ll flourish.

(Maybe you can relate, in your own life?)

I continue to appreciate each of you for following along with this journey. We’re still at the point where I know every subscriber to this list personally, so please know that I see you!!

That being said: now that we’re at the bottom of this email, I can be straight with the 10 or so people who have actually read this far.

Bruh, this s*** is hard to do. The episode from this week? I timed out every step of the process in getting it done. 34 hours and 12 minutes of completely focused time — time actively recording or editing. The episode from two weeks ago took 30 hours and 18 minutes. The input is outrageous — I’m just hoping it eventually catches on, because right now I feel like I’m building an ark for a flood that may never come. Fingers crossed, we’ll laugh about it someday.

In the meantime, here’s some other s*** to look at:

ICYMI, the last Thought Liters from two weeks ago: How to Build Your Personal Board of Advisors (just launched) 

The ongoing master plan for this whole thing: the master plan (for now) 

Love,

Adam