Thank you.

Before I dig in for the week, I just want to thank you for subscribing to my weekly notes and for those of you who have reached out directly afterwards, a special thanks. I didn’t know when I started back writing how important The Grind would become in my life, but you are my most cherished community, and I appreciate the time you give me when you let me into your inbox each week. So thanks.

There are no right answers, just different paths

Did you watch Bandersnatch when it came out? If so, pretty cool, huh?

A great throwback to the old Choose Your Own Adventure books from the 80s.

In case somehow you don’t know what these are, they are an interactive Netflix movie and series of books (respectively) where you are faced with decisions to make, and depending on the choices you make, the path your story takes (sometimes) changes.

I’m in the tail end of a process of making some choices about my career, none of which will change my associations with my businesses, but will rather change the way that I work with my businesses. As I’m making these changes, I’ve been reflecting on just how I got here, what matters to me, and what I’ve learned from previous choices I’ve made.

One value, from a business perspective, has really emerged across the key decisions I’ve made. I have consistently valued long-term value creation over near-term value extraction.

I have seen others take a much different approach, and in a lot of ways I really envy them. They have accumulated more cash than I have over the last ten years. I’ve chosen to forego that in exchange for building a body of experience, a personal brand as a creative entrepreneur, and equity value in the companies I’ve founded.

There are no right answers here. There are, however, always tradeoffs.

For the last ten years, my take home earnings from salary have basically been flat. Starting with my role as CTO at Moontoast in 2009, I have not made more money annually in salary, on average, for a decade. I’m still driving a 2008 Nissan Rogue with a huge dent in the side (part of my oldest son learning how to drive). I did buy a home but that was with the proceeds of the sale of a company that I founded, so… still.

I’ve received a few job offers over the last ten years, and I’m sure had I really pursued the job market I would have doubled or maybe even tripled my take home salary. I don’t think that’s at all out of the realm of possibility.

I never chose that path, because it always felt like if I did, I would be losing a part of my identity.

I would have lost the ability to create on my own terms, and that would never have been worth a new car, new clothes or even paying off my children’s college education up front. My personal values on work say that my ability to create on my own terms is the most important quality in my life for me to retain.

Everyone has to decide for themselves what their values are, and then allow their values to drive their decisions rather than external, material items.

As a result of my values driving my decisions in business, I’ve consistently taken my compensation in early stage deals I’ve participated in as equity. Without disclosing (or jinxing) my holding’s value, early indications are that I’ve exceeded (and will continue to exceed) the multiple on salary I would have accumulated having gone the other path. But that doesn’t mean I chose the right path.

There is no “right” path.

I just chose the path that aligned with my values, and that I was most committed to and excited about. While I can wonder about other adventures I may have taken, my decisions in business to date are without regret, and I don’t spend time thinking “what if…”

But now, my focus on near term cash versus long term holdings is starting to change. My car is going to break down soon 🙂 And I have a few more things that I’d like to do, including investing in more companies…

Ten plus years in as an entrepreneur, and the idea of being an employee in a company I don’t own seems near impossible. So the answer to more cash is not go get a job. What I have now that I didn’t have ten years ago is a credible brand. A résumé of founding successful things. Too many things for one to chalk it up to luck.

As I’m experiencing this new found desire to increase take home cash, I’m finding that while my values haven’t changed, my options have. I have new options in my Choose Your Own Adventure book that didn’t exist ten years ago when I started. Now I can adhere to my values of maintaining my right to create on my terms AND prioritize cash flow. I’ve earned that through a decade of not taking the higher salary, opting for the equity (that’s vested) and putting in the work.

And here is the point of this note.

In my years of working, the people that I have seen (first hand) wield the most power in their own lives and in negotiations are those with optionality. I had never even heard that word until I was on the losing end of a big negotiation and the winning party used it. Losing often results in great learning.

When you make decisions in your Choose Your Own Adventure book, among the many outcomes you seek, consider optionality among the most important of them. Over time, optionality becomes significant leverage in any situation you find yourself in. Your business decisions (and most decisions in life) will always have tradeoffs. As you think about those tradeoffs, think two, three and four steps ahead about where this path might take you and what optionality it will afford you. You are unlikely to get it exactly right, but even starting today to think about optionality can create new paths that weren’t previously available to you.

We have the power to choose. Don’t give that away to anyone.

Leave a Comment