Playing the Right Games

Leaving good startups and starting over

Starting over forces you to confront who you actually are when the customers, title, momentum, and routine disappear.

I’m currently in week three of a mini-sabbatical after voluntarily stepping down from previous venture and no longer being on the founding team after three years.

There is no bad blood, no drama, they’re going to crush it without me.

I started to feel nudges to shift and work on something new.

Not because the mission stopped mattering, but because I’ve reached a stage where I need to become more unapologetically fierce about the problems I see in the world. I’ve gained deep conviction on how I want to lead, what kinds of people I want to build with, and the kinds of games I actually want to spend the next decade playing.

Living in this new reality has been both liberating and painful.

I saw this 1963 self-portrait by photographer René Maltête and it struck me as an illustration to what I’m going through right now myself

Learning Under Others

Thankful I spent most of my twenties learning under other founders, investors, and pastoral leaders.

It taught me humility, discernment, and how much pressure leadership actually carries. People glamorize startups constantly online, but if you’ve been close enough to founders or been one you realize how much silent suffering exists underneath the surface. Especially when your businesses struggle to make payroll, you’re getting sued, your family life is in turmoil.

There is an unmatched anxiety and uncertainty that comes with that.

Over the years I’ve gained a sobering depth of the weight when making decisions that affect other people’s livelihoods. I meet a lot of 20 year-old CEOs now with confidence and huge ambitions. Part of me genuinely admires it and another part of me realizes confidence without formation will come with its own set of challenges.

Life happens and we will all get punched in the face. Stay humble and be kind :)

As I step into my thirties, I still don’t have everything figured out. I’ve evolved a bit but I have a stronger grasp on what kinds of people, culture, engineering style, and problems energize me.

Performative Harmony

One thing I’ve been reflecting on heavily during this transition is how easy it is to spend years playing games you were never actually designed to play.

Some people are optimizing for status, approval, safety, relevance, or wealth at any cost. If you aren’t careful, you wake up one day realizing you built your entire life around incentives you never intended to choose or your family never even asked for.

I think that’s why so many successful people quietly feel empty because they abandoned themselves and their boundaries somewhere along the way in pursuit of vanity.

For what does it profit a man to gain the whole world and forfeit his soul?

- Mark 8:36 NLT

For a long time with my early startups I tried, I minimized parts of myself to maintain harmony in rooms. I avoided conflict in certain leadership situations because I wanted to preserve peace, preserve relationships, preserve momentum.

An important lesson is conflict avoidance does not create peace it builds quiet resentment. That unspoken resentment then turns into quiet disengagement and eventually numbness.

That’s a agonizing place to build a venture from.

Truth: Courageous clarity is kinder than performative harmony.

Grieving

What nobody really talks about during founder transitions is the grief.

Not just grieving the company itself, the laughs with your team, but grieving the rhythm of your life around it. You don’t realize how much your nervous system wrapped itself around building the thing until the thing is suddenly gone from your calendar.

This break has forced me to slow down enough to notice parts of myself I had neglected which isn’t that surprising.

A new form of self-care has been just going to cafes without my laptop and just choosing to sit there. I’ve also deeply admired spending time with people who have completely different worldviews than me and its helped widen my imagination a bit more.

Market Matters

Building in the Christian and spiritual space for the last 8-ish years has also taught me a ton. Every market has its “influencers” and economics.

Underneath it all you have to remember human nature no matter how missional your idea is not everything is meant to be a business, not everything needs an app, and sometimes you cannot change human nature.

I share commentary in these posts where I talk about Idea Mazes and Do we need another app?

To be clear I’m nowhere near abandoning my faith or bitter with the church I hope it doesn’t read that way.

Moving On

One of the questions I’ve got asked is: “How do you know when it’s time to pivot or move on?”

Honestly, I think it’s deeply personal and circumstantial. There are two areas.. plenty more that drive a decision but most commonly I dissect this with economics and learning.

1. Economics: Does your venture make sustainable profit or have cash flow? Can you survive as a business long enough to get PMF? Can you provide for your family?
   

2. Learning: Are you growing in your skills? Are you delegating so you can focus on bigger only you can solve problems in the business? Do you experience challenge in the work you are doing? What might God be up to?

I think what became apparent for me was asking the question have I learned what I was meant to learn here? Equally important if I leave could this empower the next hire to come in with freshness + experience to take this further than I could?

That’s a difficult thing for founders to admit since our pride and greed becomes the ceiling on a company’s potential.

We’re stewards nothing is truly ours as much as we like to think it is.

What Comes Next?

Right now, I’m having fun catch ups with friends and advising some friends on their startups.

Personally, I know this next chapter has to be built with a new rhythm and I’m not talking about balance just a new way of working. I’ll be ready to tackle the next thing when it makes sense but I think restarting can feel terrifying. I’m truly surrendered about whatever God might have in store and just going to take it one small step at a time.

To the old co-founders our paths will cross again love you dudes and thanks for the crazy and generous 3 years that changed my life. Then to all the crew that truly helped me along the way as of recent in terms of guidance or just the casual chats I am beyond thankful.

The best is yet to come