Three conditions you should have before saying Yes

Plus! Packy McCormick brings us up to speed with all things venture capital and AI

Before you say “Yes”

Three conditions you should have before saying Yes to going anywhere:

1. Fast-forward.

Picture the thing you're about to say yes to is tonight instead of three months from now...would you be excited to go or would you wish it wasn't on your calendar? If you're not excited to do it now, you definitely won't be when the day arrives. That day is going to sneak up on you, hang over your head like a black cloud, keep you from saying yes to something else. Don't commit without running through this thought exercise.

2. Set boundaries in advance.

For example: "Yes, I will appear on the panel but I WILL NOT do a pre-panel conference call two weeks before and exchange dozens of emails with participants while they try to arrange a time for it. I show up and participate or I don't. You handle the planning." The lightest lift is agreeing to a fireside chat (you interview me), the heaviest lift is creating a slide presentation custom for the event (we'd like you to speak about topics A, B, and C). Don't say yes without establishing what you are and are not willing to do. If you think you have writers block now, imagine having a homework assignment due for someone else's event that you don't even care about. You will stare at a blank Power Point doc for hours.

3. You're not doing anyone a favor by doing them a favor.

There are only two reasons to participate in anything you're invited to: Either they're paying you or it's a fun experience to network, learn, gain exposure, establish industry cred, etc. The worst reason to do something is "to be nice." You might mean well, but your demeanor is going to reflect your lack of interest. And then you're not really helping the person you want to help after all. Be nice and say no. There's someone else out there that would love the opportunity, let the inviter work a little harder to find the right invitee.

I've done everything and been everywhere there is to go in this business. Learn from what I wish I had known over the last fifteen years. And then, when you finally do say yes to something, go out there and demolish everyone in sight.

Talking AI at Betterment this June

Having said all that, I do love to speak and meet people at events. I don’t get to do as much of this as I used to but I wanted to tell you about something I am doing in June for the Museum of American Finance.

The Museum is putting on an event live at Betterment HQ to host a discussion on AI and what it might mean for the future of asset management and financial advice. I will be moderating a panel of experts who will be sharing their thoughts on the subject. I was honored to be invited to this, if it were tonight I would definitely be excited to go 🙂 

If you’d like to register or learn more, go to 

AI and Finance Event Invitation.pdf169.73 KB • PDF File

Packy’s Back!

Our friend Packy McCormick is back for the first time since 2022 and we had a lot to catch up on. The YouTube episode is above or you can listen to it wherever fine podcasts are played, link here to find it everywhere.

Solving a Mystery

Nick Colas and Jessica Rabe of DataTrek Research joined me for an unraveling of one of Wall Street’s oldest mysteries: Why do analysts systematically and routinely overestimate the annual earnings for the stock market but underestimate company earnings each quarter?

It’s kind of weird but this phenomenon persists year after year. We get to the bottom of it. Plus, a conversation about the recent spate of new 52-week highs around the world and a look at the long-term effect of “Sell in May” on a portfolio.

Nick and Jessica are amazing on this episode, it’s such a privilege to bring their insights to you on our channel. I hope you like it:

Ok, that’s all for now. I want to wish you an awesome weekend, talk soon - Josh