Annual reflection - 2019
This week on the Startup to Last podcast, my co-host Tyler and I reflected on 2019 and looked forward to 2020. I’ve listed some of the questions we walked through along with my answers.
Reflection is a powerful tool. I found these questions both challenging and inspiring.
What's something that happened in your personal life in 2019 that you think is noteworthy?
This was a tough one. In the last 15 months, a lot has changed. I got married. And I had to leave the company I led for more than a decade.
The most important thing that happened to me in 2019 was having the opportunity to take a sabbatical. The six-plus months off allowed me to explore and clarify a few things.
I explored who I want to be as a person.
I clarified what I wanted for my marriage.
And, I was able to decide on a next step for work, launching LegUp Ventures.
I don’t think a lot of people get the opportunity to self-reflect like this in their thirties. I found it invaluable and I recommend it if you can figure out how to finance it. There's never a good time, but you won't regret it.
We're about to enter 2020, what were things like in 2010?
In 2009, I was living in Park City and working at Zane Benefits, which is now called PeopleKeep. Tyler, who was my coworker and roommate at the time, left Zane Benefits to start Less Annoying CRM. Tyler leaving forced me to take on more leadership responsibility at Zane Benefits. I took full ownership of the product and the direction of the business.
In 2010, healthcare was a huge topic. 2010 was the year the Affordable Care Act became law. It was an exciting time for Zane Benefits, which we had been bootstrapping for a couple years. We expected the Affordable Care Act to make us grow like crazy. And of course the exact opposite ended up happening. But, I remember it being an exciting time. It was when I first became interested in politics and understanding new legislature.
One thing I've learned over the last decade is to focus on getting better every day instead of the big win. Don't get too high. Don't get too low. Focus on continuous improvement.
When luck happens in a bad way, you're prepared for it. And if luck happens in a good way, you'll be in a position to take advantage of it.
How about 2019? What do you feel has changed over the last year?
In 2019, I had to figure out my next professional step. I evaluated a few different routes.
I looked into running another company that was in a bad situation. I thought this might allow me to be a “turnaround CEO” like I was at Zane Benefits / PeopleKeep.
I looked into joining a later stage company run by a CEO I respected.
And finally, I considered starting my own entrepreneurial journey.
It took me several months to get to the point where I was like, "Oh, I'm going to start my own company. And I'm going to do that as long as I can afford to do it. And if I can't, I'll go get a job."
The phrase that sticks with me from 2019 is “cashing in my privilege”. It became a theme for me. I have a lot of privilege. Some of it I was born with. And some of it I’ve produced over the last 15 years. I decided it’s time to cash it in.
I founded LegUp Ventures in May, and I've launched four ventures since. One is GroupCurrent, which provides community management for member-based groups. Another is RickLindquist.com, which fuels my research, writing, and consulting work. A third is Startup to Last, which is a podcast about building profitable companies that can last. And then there's LegUp Health, which is the most recent venture, and might be the last that I'll launch for a while.
What's something you want to pat yourself on the back for in 2019?
GroupCurrent stands out.
GroupCurrent took on its first client in June 2019. And the client, PandoLabs, was a turnaround.
PandoLabs’ original business model hadn't worked. To make matters worse, PandoLabs had recently been through another business model cycle that wasn't working.
It was a tough situation. There was a limited budget and an immediate need for a sustainable business model. It was a risky first client.
But my partner and I were both passionate about the problem. And we felt good about our ability to solve it. So we ended up taking PandoLabs on.
GroupCurrent converted PandoLabs to a member-based community in July. PandoLabs now has over 150 members and 10 partners who pay a monthly or annual fee to be a part of the community.
It’s been good. It's enabled my partner and I to have some cash flow through GroupCurrent. And it's solved a personal problem for both of us.
Before PandoLabs, entrepreneurs in the Park City area had trouble connecting. We've transformed PandoLabs into a place where local entrepreneurs can meet each other.
What's something that was disappointing about 2019?
It was my first year of marriage with Sable. I got fired in October 2018, we got married a week later, then I started doing the sabbatical thing.
And then I decided I was going to be an entrepreneur, which starts out at zero cash flow.
I was changing ideas left and right. The four ventures I've got going on right now are only four ideas of the hundreds I've contemplated.
Sable was supportive and patient with me. But I was not patient with her as she made the effort to follow along.
I bet many entrepreneurs who get married expect their spouse to know how to deal with constant change. In entrepreneurship, change is the constant. Change is progress. Change is learning. But that's new to someone who hasn't been around the entrepreneurial process a lot in their career.
So there's been an adjustment for Sable, and I could have made that adjustment easier for her.
Let's move on to 2020. Do you have a personal goal for 2020?
I want to be in a situation by the end of this year where Sable and I are ready to start trying to have kids.
It’s the selfish questions we need to answer before we decide to bring a dependent being into our lives.
What does this mean for us as individuals? What does it mean for our marriage? And are we ready for this?
Before we set more goals, what do you want the theme of 2020 to be?
If I had to pick a phrase, it would be steady continuous improvement. I want 2020 to be the year of continued calm growth.
How about the flip side? What are you most worried about? What's keeping you up at night?
I have some constraints on my willingness to continue with LegUp Ventures.
I don't want our household to experience negative cash flow. And I don't want LegUp Ventures to take third party funding. This means LegUp Ventures has to generate cash.
So I've got a plan to replace my PeopleKeep income over three years by doubling my income each year. That would make LegUp Ventures sustainable.
The question that keeps me up at night is: how am I going to generate enough cash to sustain LegUp Ventures?
Cash is king.
What are three goals for 2020?
My three goals are:
Play more every week
Increase LegUp Ventures monthly distribution revenue to $10K+
Start trying to have kids
First, I want to play more every week. I have a boring exercise routine I do most days. But I'm not doing the things I would call “play”. I'm not playing basketball every week like I used to. I’m not playing soccer every week like I used to. I used to coach wrestling, but I don't do that anymore. In 2020, I want to play more.
Second, I want to grow LegUp Ventures monthly recurring distribution revenue to $10K+. Distribution revenue refers to revenue produced by the four existing ventures. We're halfway there. So I need to double LegUp's distribution revenue in 2020.
Third, I want to start trying to have kids. I’ll leave it at that. : )