What My First Startup Taught Me: Knowing When to Let Go, and Advice to My Younger Self

Originally published in 2019 as three Medium posts. Combined and lightly updated in October 2026.

My first startup taught me more than an education ever could. I learned about myself, about venture capital and entrepreneurship, and about what it takes to build a profitable, defensible product. I also learned that starting a business is hard, and that knowing when to stop can be harder.

This is the story of the day I knew it was time to move on from MoPix, what I learned about letting go, and the advice I wish I could have given my pre-startup self.

The day I knew it was time to move on

As a third culture kid who grew up in Senegal, Nepal and Indonesia, it was only fitting that the end of my startup arrived on an airplane. I was flying home to Los Angeles from Portland, dejected, overwhelmed, and with barely any money left in our startup bank account.

Staring out the window, I had a panic attack. I had been trying to be the duck that glides calmly on the surface while kicking like crazy underneath. In reality I was close to rock bottom, overwhelmed by stress, and grabbing for anything that might help.

I had run out of runway. I had hidden much of our financial situation from my fiancée (now my wife). I couldn't pay my bills, I had spent the money set aside for our next wedding deposit, and my credit cards were close to maxed out.

From the outside, what to do when you run out of runway looks like an easy decision. Anyone who has been through it knows the emotional turmoil. That's the paradox of startup life: the passion it takes to start a business is often the thing that keeps you from letting go. You believe in the idea so much that you risk comfortable jobs and savings to chase it.

Randy Pausch said, "Brick walls are there to show you how badly you want something." Plenty of founders thrive on busting through those walls like the Kool-Aid Man. I know I did.

What we got right

MoPix started as an idea to create a Criterion Collection-style app experience for independent filmmakers. It grew into a digital video distribution system with more than 2,300 titles, one of the largest libraries of independent film online. Filmmakers could sell movies for less than the cost of a DVD, earn higher margins, and give viewers downloads to any device with all the special features of a Blu-ray.

We bounced back from tough situations more than once: disastrous hiring decisions, lawsuits, demanding clients. I remember with real fondness how the team came together to get things done. We had a few heroic moments too. We sold the vision before we had a product by using the Transcendent Man app. We were a finalist in the SXSW Accelerator pitch competition when we badly needed a win. And we acquired the Film Baby business from CD Baby.

Why it didn't work

In the end, with modest sales, an exhausted team and the money running out, it was time to let go. The core lesson: disruption in film wasn't a distribution problem. It was a content problem. Content attracts the audience; distribution gets the word out. Hollywood is a high-touch business, and we were trying to run a low-touch one that gave filmmakers an automated process with limited support. We were mercenary entrepreneurs in a missionary business.

How to know when to let go of your startup

There is no easy way to move on. If you're in a similar spot, you're probably wrestling with the same questions. Can you extend your runway? Can you close a new investor or customer? Does the company still bring you joy? Do your investors believe in you? Do you believe in yourself? How do you talk to your team, your co-founders and your family? It can feel lonely until you finally admit to yourself that the venture has failed and start the process of moving on.

I believe you know it's time when you've run out of emotional runway, not just financial runway. A startup dies when the founders give up, not when the money dries up. It isn't about proving others wrong or recouping what you invested. It's about recognizing that you're burnt out, your team is burnt out, and customers aren't buying in a way that will reach the goals you set. When you're honest with yourself, it becomes clear it's time to hit reset.

On that flight from PDX to LAX, I recognized that my passion and drive to lead MoPix were gone. Two days later I wrote to my co-founder and started the process of moving on.

Moving on from a failed startup

Moving on is a process. Focus on what you can learn. Embrace that there are no mistakes, only wasted opportunities, and use the experience to build resolve and resilience. Astro Teller, who leads Alphabet's X moonshot factory, argues that failure should be valued as much as success.

The greatest people in history have had failures. Celebrate like Michael Jordan coming back for a second three-peat. Once you do, you'll feel the weight lift from your shoulders. Then it's on to the next one.

With MoPix we had a chance to pioneer a new category. The market took longer to develop than we could wait. But the lessons of persistence, determination and boldness have stayed with me ever since.

Advice to my pre-startup self

Dear Ryan, you will fail. Failure is not the end.

• Ask if this is what you really want. Do you have the energy, drive and determination to start? You'll need courage, persistence and passion.
• Pick your co-founders very carefully. A company's DNA is set by its founders.
• Skip the self-promotion game. Focus on building the product toward achievable milestones.
• Stack small wins. Companies succeed through long strings of small wins and good small decisions.
• Build momentum. If things go well, the money will come.
• Never stop pursuing alternatives. Be ready to adapt.
• Stay curious. You don't know it all. Ask a lot of questions.
• Hiring will be one of the hardest parts of the job. Land remarkable people with intellect, street smarts and a get-it-done factor.
• Lead, don't dictate. Put people at the center. It's not the work we remember with fondness, it's the group that came together to get it done.
• Be honest with yourself. In a startup, honesty about your situation is the most efficient way to run the company.
• Learn to tell stories. The world makes room for passionate people who can inspire others.
• Respect startup time. You'll need to do more with less. Prioritize growth, but keep perspective.
• Overcommunicate early with your spouse, your team, your investors, everyone. Startup life is hard on relationships.
• Take care of yourself. Make exercise a routine, and learn to unplug.
• Reflect before you resolve. You'll accomplish more of what you want.

And don't be embarrassed by your failures. They're life lessons.

Founder resources I still return to

I used to keep a long startup toolkit of links. These are the ones that have held up best:

• Do Things That Don't Scale by Paul Graham
• Startup Playbook by Sam Altman
• The Days Are Long But the Decades Are Short by Sam Altman
• The Struggle by Ben Horowitz
• How Superhuman Built an Engine to Find Product/Market Fit by Rahul Vohra
• Y Combinator Startup Library

For the full archive, see Stoner's Startup Toolkit on Medium.

Building something?

I've been a founder, an operator and, since 2016, an angel investor. If you're a founder working through a hard call, I'm happy to compare notes. Get in touch.