If Guilded Had Existed 20 Years Ago, I May Have Never Learned to Code

Even before we invested, I’ve been enamored with Guilded — a platform to find, manage and challenge online gaming teams. Chiefly, they have done a brilliant job building something people love by engaging directly and authentically with gaming communities on Reddit. In addition, they’re building the very software I wish I’d had all those years ago when I had more time to game, let alone enough time to run a gaming team!

Quake II helped me learn to code. It wasn’t long after I started playing that I noticed [clan] tags next to some — usually the best — player’s names. I needed to be in a Quake II clan. After trying a few different teams, I inevitably needed to start my own. This gave me an excuse to learn HTML so I could build and maintain our team’s website. That prepared me pretty well for my career in tech.

Believe it or not, it took two decades for the Guilded team to come along and build a solution that integrated all of the fundamental things a gaming team needs into one service including a calendar, forums, website builder and wikis.

Guilded is helping manage the top professional gaming franchises — it can definitely handle your gaming team.

Just yesterday, the team at Guilded rolled out a major product update with some of the top esports franchises on board. As an early stage investor, we make our living making big bets on founders when the product and traction are often still nascent. At the time we invested, there was already a strong signal that this team was making something people love because Eli, the founder and CEO, was building the product right along with his audience on Reddit.

With a community on Reddit for every game, there was no better place to start finding users. Fittingly, Eli approached building the product similar to how we approached building Reddit: by talking to our users — on Reddit. Eli’s been doing this since he launched, which was not only beneficial for him but also a gift for the community he was a part of and wanted to build something for.

What are you waiting for? Talk to your customers.

Too many founders are concerned with getting it perfect for a Hollywood-style launch. Build something that’s good enough to solve a problem, get it out to some of the people who need it most and talk to them. I’d have to offer people free coffee around Davis Square in Medford, Massachusetts to get them to sit down with me and try Reddit in order to learn what they thought and see how they used the product. That was 2005.

But even when things went badly (e.g., the site would go down for a few hours), we’d never think of banning the top post on the site, which inevitably was about how dumb we were. Rather, we got in the comments and explained what went wrong and how we were going to improve. People really respected that. It’s fitting that learning how to build a website for my videogame team led me to build Reddit, which has now helped Eli build a website to manage these teams for the community on Reddit.

When you’re getting started, being an engaged founder within your community of earliest adopters carries real weight, especially if it’s a community product. It shows them you give a damn, which builds loyalty, (because you’ll need that when you inevitably misstep). And it gets you close to your core customers, who you’ll need to make the right decisions about product and the business.

Zero Lives Remaining - Reflecting on the last 10 years since losing my mom

LIVES REMAINING: 0

System of a Down blaring on my stereo, I scrawled this on my bedroom wall at some point in my angsty teens. I noticed I’d always played video games better when I was on my last life. Back when video games were hard, you’d get a finite number of lives before it was game over and there was nothing like being on that last life to sharpen your focus.

I didn’t realize at the time just how important that idea would become to me, but it hit me within the first few months of founding Reddit. I’ve written about what transpired, but only recently have I started talking about the effect that losing my mother — after a three year long battle with brain cancer — had on me.

Last week was the 10-year anniversary of her passing. I called my dad like I do every year on this day and we caught up, shared memories, and remembered her. A lot has changed in the last year; she would have been so happy at my wedding. (We had it on her birthday.) Mom would be giving my wife’s mom some serious competition for Junior’s biggest fan. She’d also be really happy for me to be back working alongside Garry Tan at Initialized.


This seemed like a good time for reflection. As entrepreneurs, we are all so busy “crushing it” that physical health, let alone mental health, is an afterthought for most founders. It took me years to realize that the way I was feeling— when working on Reddit was the only therapy I had — was depression.

It was a thick fog that always lingered, muting good feelings and amplifying bad feelings. It showed up just before my mom was diagnosed, because my then-girlfriend had a serious accident while studying abroad; and it settled in for the next few years. I don’t recall when it went away, but it was sometime after mom passed. I felt lighter again. Someone turned the volume back up on life.

I haven’t felt it in a long time and I’m grateful for it, but it doesn’t take losing a loved one to feel this way, especially with the pressures of entrepreneurship. When you’re struggling, talk to someone. It can be a professional, a family member, or even a stranger can be helpful in getting you into a better headspace (that’s one reason why we invested in 7cups).

We’re all a work in progress.

Executives Need Coaches, Too

I only got an executive coach three years ago and it’s easily been one of the most valuable investments I’ve made in myself professionally, and personally. We often push founders to executive coaches and consistently check-in with them in good times and bad to make sure they’re taking care of themselves.

And why shouldn’t executives have coaches? The greatest athletes in the world all have coaches. They’re the only professionals who have real, quantifiable, undeniable wins and losses. The rest of us are bullshitting each other by ‘keeping score’ using revenue numbers, headcount, or valuations — athletes actually win or lose every day they go into work.

I’d argue every profession, especially if you’re trying to be the best, should have some form of coaching. And that makes me bullish on a company like Torch, providing those services at scale. One day, it will seem absurd to be an executive, or even a manger, and not have a coach — as absurd as it’d be to see a basketball team take the court without their coaches courtside.

You’re going to need to keep growing as a leader and getting outside perspective and guidance is a natural part of the process. Take care of yourself because you’re not getting uploaded to the cloud anytime soon. And when things do get hard, which they will, you especially need to prioritize your well-being.

Take Ownership Of Your Most Valuable Asset

Yourself. That starts with exercise and wellness for your body and your mind. I waited until I was going to be a father to start taking this seriously. That was idiotic. Moderate the garbage you’re putting into your body and commit yourself to a healthy routine — you don’t need any equipment to do a wide range of bodyweight exercises or go for a run. Founders especially will forget this because we’re so busy out-grinding one another.

Your environment has an outsized effect on your outcomes. It’s not just the people you surround yourself with (remember: you’re the average of your five closest friends) but also the places where you spend your time. Your work, your home, that amazing spot where you finally use some of your vacation time… get yourself out of situations and away from people who are not making you better. You only need an internet connection to change your perspective in a minute (see the community at r/getmotivated).

Our time is all going to be up at some point and when you’re (hopefully) looking back on it, the people and experiences you have in your life will be what you cherish or regret. I know because I saw it firsthand and getting that privilege at 22 meant I could live those years of boundless energy and optimism with some of the wisdom of someone much older.

You’ve got one life remaining, don’t squander it.

Alexis, Fully Initialized

Today, I’m very excited to return to Initialized Capital as a full-time General Partner alongside my longtime friend and collaborator Garry Tan.

Here’s a little history first. Initialized launched in 2011. Before that, Garry and I were having success as angel investors and founders kept telling us we were providing more value than other much better funded investors.

Before long, we’d raised $7 million for our first Initialized fund, which made seed investments into startups like Instacart and Coinbase. We were on to something.

Since then, we have grown to manage more than $250 million, which is invested in companies that are now worth more than $20 billion (including six unicorns, or startups that are worth over one billion dollars). We’ve recruited a remarkable team of partners, and built a ton of software to scale all of the traditionally high-touch, and less scalable parts of the venture business to better serve our founders.

We want to be the first check and we want to do the work — we aspire to be the kind of investors we wish we’d had when we were founders. And after more than three years of serving back at Reddit, my first “baby” is in a much better place and has a great team in place.

Now I’m back at Initialized with even bigger ambitions than when we started. As a new father of a five-month-old little girl, I want to make sure the world she inherits is as great as possible. This depends on the entrepreneurs of today and tomorrow building companies that truly matter.

Photo credit: Chuck Revell

Taking Care of Your Health While Running A Startup

The first time Zachariah Reitano founded a startup, he went through the Y Combinator program and found himself rushing back and forth between New York City and the Bay Area while struggling to get the company up and running.

“We fell into the stereotype of young founders who felt they needed to stay up all night. We often pulled all-nighters unnecessarily,” he said. “Sleep is not a gas tank. You can’t run it to empty and sleep all day on Saturday.”

He pushed so hard toward exhaustion that he walked into a hospital and literally fell asleep — only to be revived by getting an IV plugged in.

“That was a definite wake-up call.”

This time with his next company Roman, he’s doing things differently. It’s a common experience we see at Initialized Capital — that second-time or serial founders become more disciplined about the way that they manage their health and well-being while running a company.

How charging for our product originally hurt — but ultimately saved — our startup

Five years ago, my co-founder Claire McDonnell and I founded True Link Financial, and did two things that that were totally unorthodox for the time.

First, we didn’t build a startup for teenagers.

We built it for seniors. (We’re a financial services firm that offers debit and Visa cards and investments management for aging Americans.)

Secondly, we charged our customers actual, real money for what we had built.

This was not common practice at the time. Around 2012, we and a whole cohort of other startups — Simple, Plastc, Swyp, Coin, Final, Stratos, Clinkle, and others — were getting card-issuing companies off the ground.¹ We also launched a Visa card — but our goal was to protect older folks from fraud, a $36 billion problem that affects millions of Americans, including my grandmother. Our cards would automatically decline scammy transactions so seniors like my grandmother would be able to still carry a credit card, preserve their independence, and spend their own money — and in order to decline the transactions we had to become the issuer of the card.²