Failure, Depression, and Yoda

About two weeks ago, Tim Ferriss wrote a post called, Some Practical Thoughts on Suicide. It was painful to read, but Tim came forward and told an honest story about his battle with depression.

Coincidentally, I was in the airport coming back from a conference where I gave a talk titled, The Truth About Failure. In preparing for my talk, I was finally able to put thoughts to paper and be honest about my struggle with depression. After reading Tim’s post, I knew my talk wasn’t enough.

Below is my story. If you’re struggling with depression right now, especially if it’s related to failure, know this: everything will be all right.


Isaac Asimov wrote a book called The End of Eternity. It’s a great science fiction novel about a world where time travel is constantly used to change history in order to eliminate catastrophes.

The society Asimov created, called “Eternity,“ essentially rooted out failures. I think this passage is particularly relevant to failure, pain, and depression:

“In ironing out the disasters of Reality, Eternity rules out the triumphs as well. It is in meeting the great tests that mankind can most successfully rise to great heights. Out of danger and restless insecurity comes the force that pushes mankind to newer and loftier conquests.
Can you understand that? Can you understand that in averting the pitfalls and miseries that beset man, Eternity prevents men from finding their own bitter and better solutions, the real solutions that come from conquering difficulty, not avoiding it?”

In December of 2011, I was living in the Short North in Columbus, Ohio. I graduated from Ohio State about seven months earlier and was working for a company called Duet Health.

I spent my college career avoiding classes in favor of side projects like home brewing beer, designing iPhone apps, and learning about what it took to start a company. After less than a year in the workforce I was antsy to start my own thing again.

After a Startup Weekend, a mentor of mine threw an idea out to me. He had been arbitraging Facebook ads, it was working, but he didn’t have time to work on it anymore. He suggested I run with the idea.

It was fairly straightforward: build landing pages for hotly anticipated consumer goods that have yet to be released (the next Call of Duty for example), target that product’s Facebook Page, run ads, and then have links to pre-order the products on each page. We would take an affiliate fee. We would eventually call it LaunchGram.

I convinced a couple friends of mine to join up with me on the side. We got into an accelerator in Columbus that didn’t take any equity at the time, and we started spending a lot more time on the thing. We eventually decided to pack our bags and move the operation to the Bay Area — startup Mecca.

It wasn’t long after we arrived in Mountain View that we realized Facebook ads had gotten more expensive. Our advertising arbitrage opportunity was gone. So here we were in Mountain View without a distribution plan.

We came up with a couple ideas, and one was good enough to get us into 500 Startups right when we were running on fumes. We celebrated getting into 500 Startups in the Fall of 2012, but after two months in the accelerator I knew we were dead.

Not having any money wasn’t as much of a sign of failure to me as it should have been. I spent the better part of the year with a couple hundred dollars in my bank account and several thousand more racked up on credit cards. Up until late November 2012 though, I had found a way to scrape together a bit more cash each month to keep going.

I was pitching a lot of investors on LaunchGram, and I started to find myself agreeing with their conclusions that this business wasn’t either very big or very viable. I had a sick feeling in my stomach every time someone asked me what I did.

I started to lie to people at bars or on the train when they asked me what I did. I didn’t want to talk about my startup, because I knew it didn’t make a ton of sense.

Over Thanksgiving I did a lot of soul searching. Not only was this business not working for a usage standpoint, I didn’t care about the problem.

Did the world really need a better infrastructure for product promotion leading up to a launch? Was that something that would actually make the world better? Was it something I actually wanted to be spending my time on?

No. Looking back, I was lying to myself about being interested in LaunchGram. I came back from Thanksgiving and told my co-founders that we were out of money and the show was over.

We had poured our hearts and souls into this thing, and it was done now. I held my feelings of failure close to my chest leading up to the conversation, and it came as more of a surprise to Zach and Carrie than it should have.


I was pretty lost after this. I didn’t think I was good at anything, and I didn’t know what I wanted to do. I had done some design, I had done some sales, I had done some product management, but I didn’t have enough experience in any of these to land a good job. I wasn’t even trying to find a job for a little while.

There was this vacuum in my life; I had nothing to fill the vacuum LaunchGram’s failure had created. I couldn’t come to terms with the idea of not running my own thing anymore.

Worst of all, I didn’t have any friends I could relate to with all of this. Carrie, Zach, and I remained friends, but things sucked for a while. I blamed myself for letting them down, and to a degree I still do.

Along my journey of building LaunchGram, I periodically sent out update emails to people who had helped me out along the way. It was a list of family, friends, investors, and people whose input I valued. When I decided to shut down LaunchGram, I sent an email out to this list.

The email reached one of my co-founder’s family members before they had a chance to tell them what had happened. Another screw up — damn. I didn’t even know how to fail.

Several great things came from that email though.

About fifteen minutes after I sent that email, an acquaintance named Joël — someone I had only ever met twice — called me. I didn’t even have his phone number.

The first thing he said to me was, “Are you okay?” I was both appreciative of the call and confused. My failure was still fresh… but I was still in denial of how hard the next few months would be. I thanked him for the call and assured him I was okay.

I wasn’t okay. When I saw my friends, I told them things were great — I was finding the next thing! That, of course, was a big ol’ pinocchio lie. I stayed home, played video games, half-heartedly searched for a job, and was trying to teach myself CSS. I needed do build something.

There were days I sat in front of my text-editor all day, making progress, feeling strong.

The next day I would interview, fail to find anything compelling, and feel hollow.

A mentor mine named Christian Long also responded to my email. He still lives here in Columbus. He said:

“As Yoda reminds: ”Do or do not. There is no try.“ But — just as importantly — he only tells Luke, a Jedi in training. That’s the key. 
BE humble now.
As you are.
Be passionate.
As you’ve elected to be.
Be willing to trust the way forward.
Again, as you are.”

“Do or do not. There is no try.” This email meant so much to me. I wasn’t looking for sympathy, and this was not that. It was support; it was encouragement.

It helped me realize that failure is something that happens when you set out on adventures.

I pictured Luke on Dagobah with Yoda. I knew the path ahead of me wouldn’t be easy, but Christian helped me see that there was a path ahead.

One night in January of 2013, I had less than $20 to my name. An entrepreneur named Dan Martell had invited me to a dinner with 10+ other founders, and I deluded myself into thinking I belonged there. It was my last hurrah before I packed my shit up and asked my Mom and Dad if I could come back home.

I spent $7 on the Caltrain to get to San Francisco from Mountain View. My friend Danielle Morrill happened to be at this dinner. Everyone at dinner was ordering ~$30 dinners (standard fare), but I didn’t have $30. I ordered a beer and manufactured some self-confidence.

After dinner, Danielle approached me and asked me if I was all right. I told her that I was great, but she noticed I only ordered a single beer and didn’t eat at an event where people were feasting and having a blast.

That’s usually my queue to have more than a single beer.

Danielle called me out, “You’re broke aren’t you?”

I’m not sure how you respond to that, but I’m pretty sure I just eloquently said, “ugghghghhghg blarghhhhhhhh yeaaaaaaah I’m broke.”

I was legitimately planning my quiet escape plan from California. That night, Danielle and Kevin cooked me one of the most meaningful meals of my life: grilled cheese, tomato soup, and a couple cold beers.

At the time, I wasn’t even comfortable telling my co-founders, Zach and Carrie, how terrified and depressed I was.

Danielle and Kevin didn’t offer me a job that night, but they did loan me some confidence to get back on my feet. Danielle did something pretty great that night. Instead of assuming I’d go get a job at a startup or move home, Danielle asked me what I was going to start next.

I thought I was a failure as a founder, but Danielle believed I’d just start something else.

Before this dinner, I thought I would be calling my Dad the next morning to explain to him how I needed to move back in with them for the first time in five years because I failed and was broke.

Instead, I called my Dad the next day and asked him to stake me for two more months in the Bay Area. I told him that I believed that I could figure something out in two months — starting something new, getting a job a startup, anything. My Dad staked me.

In twenty four hours, two people I looked up to for mentorship on this crazy ride as a founder chose to take a bet on me.

About a week later, I was depressed again. Before this time in my life, I used the word “depressed” pretty lightly. Now I think I understand what it means to actually be depressed. I let my friends down, I wasn’t good at anything, I was down on everything. I started crying at silly things. I knew something was wrong and that I needed to get back on my horse, but I didn’t know how.

I was taking the Caltrain into San Francisco from Mountain View a lot, and for those of you who don’t know, somebody jumps in front of the train at least once a month. I was on the train three months in a row when this happened. The train stops and you’re stuck for an extra thirty minutes to an hour. One time, after the train started to pull away, I was looking out the window and saw the aftermath.

I saw the bodybag…only a few yards from the Palo Alto Caltrain station. I already wasn’t having a good day, but I started to wonder who these people were. I wondered if I would be one of those people in a few months if I didn’t get my life figured out.

I never got past that point. I never seriously considered physically destroying myself, but just thinking about it terrified me. I had to get control over my life.

See, running my own company, whether it’s going well or not, was like a really good drug, and I was going through withdrawal. There was a void in my life that I just couldn’t fill no matter how hard I tried. It was like someone important in my life had died and I couldn’t bear their absence. Except in this case, the person was part of me. I was nearing the end of my two months, and moving to suburban Philadelphia was looking more and more real every day.

I started to understand why Joël called me and asked me if I was okay. 
Over the next month and a half, I got a couple great opportunities, but nothing really spoke to me. I felt like I’d be making the same mistake I made when I started a company and didn’t care about the problem.

One thing was for sure — being on Dagobah sucked.

Then one morning, Danielle texted me saying she’d like to “buy my company.” I didn’t know what that really meant, but I drove up to San Francisco immediately to get coffee with her.

We talked about how LaunchGram and Referly could be a good fit together, but I knew that Danielle was losing faith in Referly. We talked about other startup ideas, and she offered me a sum of money to come join her and Kevin.

What I would do wasn’t clear, but I knew that I respected these people, and working with them could not be bad. I took the deal.

Two weeks later, Danielle and Kevin decided to let everyone go at Referly, but they asked me to stay to help create the next thing. Danielle had raised $1.2M for Referly, and we had about half of that left… to do basically whatever we wanted. While Danielle wasn’t “closing the company down,” she was giving up a product she had worked tirelessly on for more than a year. I saw her going through the same things I had gone through, just on a four-month delayed schedule.

We didn’t know what we were doing for a while, and figuring out what to do is a different story. Through the early days of what would become Mattermark, I still felt like shit. Sometimes I wondered whether I was a washed up entrepreneur screwing around with two other washed up entrepreneurs.

Maybe that was true, but as we settled on something interesting to work on, I started to feel a whole lot better.

Getting above “pre-LaunchGram parity,” though took me almost two years, but I did get back on my feet. I got more than back on my feet. Whether I “beat depression” or just plain got back on my horse, I ended up humbled and unafraid.

Tim Ferriss said, “If we let the storms pass and choose to reflect, we come out better than ever.”

It echoes Asimov’s, “Out of danger and restless insecurity comes the force that pushes mankind to newer and loftier conquests.”

People will tell you that failure is a risk you take when you set out on an adventure, but what they don’t tell you is that failure can be a gift. It is a rewarding experience despite how painful it can be.

About a year later, when I got an email from a founder that looked a lot like the one I sent when I closed my company down, I understood. I gave him a call just like Joël had called me. I got his voicemail, so instead I opted to send him an email.

I said, “As Yoda reminds: “Do or do not. There is no try.” But — just as importantly — he only tells Luke, a Jedi in training. That’s the key.“