10 Years in Startupland

10 years.

It's safe to say that a single year at a startup is equivalent to several at a big company, and I've got to be real with you, I feel it. Since my very first startup in 2007, in a basement (cliché, I know), I've been on the grind. Nonstop. That's the nature of choosing the startup path. Nothing comes easy.

From basements to boardrooms. From 2 person companies to 250. From Seattle, to Silicon Valley, to New York. It's been a road. I've started two, joined four and advised dozens. Some have been successful, some haven't. That's the nature of the beast.

When I first started out, I spoke so loudly about all the many things I knew to be true from my first company. If you followed me on Twitter back in 2008, you saw. Then you keep going. And what you thought was true, well, wasn't. That's why I try to avoid blanket advice these days. Instead, I only try to only make recommendations based on patterns I've seen. If I've learned anything, it's that nothing is absolute in startupland.

But there are patterns. Lessons that seem to repeat themselves over and over again. That's the point of this post, to digest and regurgitate those patterns into something of value. And selfishly, for me to reflect. Couldn't think of a better topic to kick my blogging hiatus.


You Can Build A Successful Company Anywhere

There's an emphasis on physically being in Silicon Valley. Rightfully so, it's the birthplace of the startup. But Silicon Valley is home to much more; bad actors, high cost of living and a ton of distraction. The concentration of capital and founders can be helpful, sure, but it's not critical. A great technology company can be built from anywhere. Look around. Amazon in Seattle. MailChimp in Atlanta. Tumblr in New York. Snapchat in LA. Location is an excuse and will increasingly become more of an excuse as the web and capital markets become more distributed. As a rough example, my first startup was built in a little town called Bellingham, WA. We raised money, got covered by TechCrunch (more important back then) and built a real business that still exists today. That was in 2007. Today, there are startup hubs in nearly every city around the globe. There's nothing magical about Silicon Valley, as much as the world may tell you so. You can build your startup anywhere.

Momentum And Growth Are Everything

There are two fundamental truths of a successful startup. Great product and great growth. Nothing else matters. The thing that makes creating a successful startup so difficult is that these things are not given, they're earned. Each day you have to create momentum from nothing. Great product is well documented, so I'll focus on the latter. Growth dictates everything. Without it, raising money, hiring top-tier people and getting to a successful exit is impossible. I'll dig into more on how to create growth in a future post, but for now, my best advice is this: Pick a single metric, track it maniacally and work to improve it each day. Create momentum in the metric that matters for your business (eventually this will become revenue, but likely not at first). Nothing else matters as much as this.

Value Stock Options, But Only So Much

I've had stock in every company I've been a part of. Thus far, only one of those companies have produced an actual return for me out of that holding. Others are still "too early to tell," but the point is that, well, stock options are tough. Odds are, that as an employee, your stock options will be worth nothing or very little. Good primer on that math here. There are exceptions to that of course, in unicorn-like exits. But for the most part, this will prove to be true. That doesn't mean that you should ignore stock options or shouldn't negotiate your fair share, but don't over-index on them. They should never replace salary. Ever. Options are icing on the cake, not the cake itself.

Optimize For Learning, Not Titles

The true value of starting or joining a startup is the knowledge you gain, simple as that. Just as the amount of work at a startup is condensed, as is the knowledge you can gain. That's why I recommend that every person works for or starts a startup at the beginning of their career. Knowledge gain is the most important thing early on. Don't obsess on your title. Just try to get your hands in as many things as possible. This process helps you understand what you're best at and what you enjoy doing most. And at a startup, there's no bureaucratic barriers or red tape. Only a blank canvas.

The Role Of Luck Is Very Real

I don't want to understate the importance of hard work, it's a key differentiator, but the role of luck in startupland is very real. I can name at least 3 instances where I turned down a job at a company that went on to a massive exit. I look around at dozens of my peers that are worth many millions of dollars. Luck isn't the only reason, but it's part of it. It's easy to get caught up in the success that you miss out on or the success that surrounds you. This is the burden of dealing with ambition. And this industry complicates that burden more than any other, especially at a young age. Learn from that luck, but don't dwell on it. Heads down. Stay focused. Ignore the noise.

Pick Your Venture Capital Carefully

When I first started, I thought the goal was to raise money. Turns out, it's not. Shocker. Venture is a necessary (in some cases) evil. The goal of a startup is to build a real business. Venture is simply a vehicle to help you do that, but it comes with a price. Not just in equity, but in the type of business you're required to build. The venture game is built on exits and multiples. When you take venture capital, you commit to this and a board of investors that may have a different vision than you. I'm not recommending that you avoid venture, but be aware of the baggage that comes with it. Bootstrap as long as possible and take money only when it's necessary to reach your next phase of growth.

Find The GP (Good People)

This is true in any industry. But as the spotlight has shifted to startupland, the ratio of good people has declined. Be aware of that. Weed out the people that don't have a moral base. Things get hard in startups. People show their true colors when things get hard. Pick the people that you trust.

Take Your Swing

Finally, take your swing. There's two ideal moves in startupland. The first is to join a rocket ship, a company that is young but growing quickly. This provides the best opportunity to grow in your career. The thing you're optimizing for here is knowledge and professional growth. The second move is starting a company of your own. There's no other way to control your own destiny. Being an employee at a startup is one of the most thankless jobs you can have. Once you feel like you've got the knowledge you need to take a swing, take it. That's when the real fun begins.


I'll save the verbose closing and say that these 10 years have been irreplaceable. Ups and downs, highs and lows. They've aged me (ha), but have taught me an incredible amount about this business and more importantly, myself. There's no better place to spend your time than in startupland.

Here's to 10 more. Come build.

Hi there, I'm Andrew. Welcome to my blog. I'm an entrepreneur that loves the process of building and scaling startup companies.

This is where I share my journey and lessons learned, feel free to follow along. Read more →

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