A year after being “let go”
I recently crossed the 1-year mark after PeopleKeep asked me to resign as CEO. I feel great. My body’s healthy. My mind’s clear. And I’m ready to go.
To those of you who’ve subscribed to this website over the last year, I’m sorry for not writing many articles so far. I promised you I would. I thought I’d write more, but I wasn’t ready. I spent most of this time reading and thinking about what’s next.
The question of “what’s next” was harder to answer than I expected. To make matters worse, I received conflicting advice on how to approach the answer. On one side, people told me not to worry too much about it and to “jump back into the saddle”. On the other, people told me to take as much time off as I could afford. I chose the latter.
During my time off, I explored three primary pathways:
Joining a later-staged company led by a CEO I could respect and learn from. The primary driver here was to learn how to be a better leader and manager.
Finding a new CEO job at an earlier-stage company. I’m confident I could succeed in this environment based on my past experience.
Going out on my own. This has been my dream all along, but I’ve never felt “ready”.
I spoke with CEOs about option 1. I talked to investors about option 2. And I sought advice from entrepreneurs on option 3.
So, what’s next?
I decided to go with option 3—going out on my own. I made the decision on a ski lift when my friend Brian Poger was visiting Park City this year. Brian listened to me explain the three pathways I was considering. Then, he looked at me and said, "Rick. I can’t imagine you doing anything other than going out on your own for any reason but fear.”
That was all I needed to hear.
As CEO, I learned the negative power of fear-based decision-making firsthand. It’s a topic I plan to unpack further in future articles. The minute Brian called out my fear, I knew option 3 was the way to go.
So, I’m going out on my own. I’ll be on my own as long as I can afford it and as long as my marriage will allow it. 😉
My friend, Tyler King, and I had a recent conversation on privilege. Tyler told me he thinks too many privileged people fail to take advantage of their privilege. They let it sit there unused.
I’m going to cash my privilege in.
At the very best, I’ll figure out how to sustain my family’s lifestyle on my own. At the very worst, I’ll go get a job and try again later.
What this looks like right now
Right now, I'm all over the place (in a good way). I've started a holding company with my wife, Sable. It’s called LegUp Ventures and exists to incubate ideas and turn them into businesses. So far, I've started a few ventures:
RickLindquist.com (this website). This is where I plan to research, write (more on this below), and consult. Right now, I'm researching emotions and leadership. My goal is to turn the research into something publishable down the road. I do not have an active consulting client, but I expect to take on a new client after the new year.
GroupCurrent. This is a professional services business I started with my friend, David Bieber in Park City. It provides outsourced management for member-based groups and communities. Once we generate enough cash flow, we should be able to build a software platform.
Startup to Last. This is a weekly podcast I started with Tyler King (my former partner in the early days of Zane Benefits). Both of us are founder CEOs. We discuss topics around what it takes to build software companies that can last.
LegUp Health. I plan to launch something in the consumer health insurance space. I see so much opportunity here.
I expect one or more of these will take off, and I will double down on focus. I’d appreciate any advice or support you’re willing to provide.
What writing you can expect moving forward
I plan to write about what experts have spent lifetimes and careers figuring out. I read hundreds of books and articles every year. My plan is to turn this reading into useful tidbits you can use today.
My ideal reader is someone like myself: an intellectually curious person. Current readers include students, entrepreneurs, CEOs, leaders, coaches, and more. What do they all have in common? A passion for learning and increasing their capabilities every week.
Here’s what you can expect from me moving forward:
A focus on useful, long lasting information. ♾️
An 8th grade reading level or below. (I wrote this article at a 3rd-grade reading level.) 🧠
Articles posted every week. 📝
Notes from the books, articles and podcasts I’m consuming posted every week. 📚
A weekly newsletter every Sunday with: 📰
A quick update on what I’m working on.
Any new articles I’ve written.
Any new notes I’ve posted.
A few recommended content pieces from around the web.
A special thank you
This year-long transition was harder than I could have imagined. I could not have done it without the people mentioned in this article: Sable, Brian, David, and Tyler. I give special thanks to each of you. And thank you to everyone who has supported me during this transition. 🙏