11 massive startup lessons Om Malik learned building an online news empire

Six years ago, Om Malik decided to leave his position at a magazine to build an online news startup. The startup would become GigaOM, which today is one of the web’s most frequented destinations for tech news and in-depth analysis.

Before founding GigaOM, which has now grown to a staff of writers in 12 cities in four different countries, Malik faced inner turmoil — as most entrepreneurs do — about which direction to pursue in life. At the time, he was writing for Business 2.0, the monthly magazine co-founded by renowned entrepreneur Chris Anderson (editor-in-chief of Wired until 2012). By 2005 however, it became clear that GigaOM, his personal blog at the time, had grown to serve a larger readership than that of Business 2.0.

When Toni Schneider, now CEO of Automattic and a venture partner at True Ventures, posed the question: “what makes you happier, writing for GigaOM or Business 2.0?”, Malik answered by leaping. Looking back, it was the right decision as Business 2.0 failed to make sufficient profit and was shut down in 2007. But, at time, the leap was a treacherous one.

Malik had very little startup experience. Before founding GigaOM in June 2006, the closest he got to having a startup experience was being a member of the founding team of Forbes.com. “So from day one, my knowledge about how to do a startup was zero. There weren’t any blog posts, no cheat sheets and no hands-on guides. The idea of a distributed startup built on a tiny seed investment was novel at that time,” writes Malik.

In May 2006, True Ventures decided to fund GigaOM, and so began Malik’s roller coaster ride. “I went into a panic mode. There were many sleepless nights and countless cigarettes. I remember sitting down in the balcony of my apartment and looking into the night, taking stock of my life so far. I thought about things I had done right and things I had done wrong. What I had learned and why,” writes Malik.

Fast forward six years and GigaOM has become one of the most recognised online media empires. Malik recently summed up the lessons learned he learned, and we decided to condense it into capsule form. Enjoy.

Be honest with yourself and take time to self reflect before making big decisions in life.

I often tell others – if you walk looking back, you are going to fall flat on your face. So perhaps this was the scariest thing I had to do. I don’t think we as busy professionals and Internet junkies know how to sit still and self-reflect. It is because perhaps we don’t want to get lost in the byways of the past.

Those nights of self-reflection during the early startup phase exposed me to a lot of my own demons and made me realize how little I knew. The biggest outcome of that conversation was the realization that companies and startups are essentially a reflection of a founder. If a founder doesn’t realize that, then it is going to be extremely difficult to build a long-term business.

Be transparent, be honest and be as clear about both good and bad news.

Do that, and people will trust you. They will fight for you.

That became the core founding principle of GigaOM. When I was growing up, my grandparents and parents always said: if you treat people with respect and decency they will treat you in the same way. And those who don’t, well, you don’t have to deal with them. It has served me well pretty much all my life.

Be respectful, be decent to people and you will get that in return.

Whether it is readers, peers, or people who do business with us, it doesn’t matter. It seemed like a good founding principle for our company.

Working as a reporter for various publications I knew first hand that newsrooms are cesspool of politics, driven by individual ambition. Companies are often brought to their knees by hierarchies and behind closed-door ideology that is commonplace in traditional business world.

Build a peer review mentoring culture.

It will help avoid politics and at the same time, makes everyone proud of each other’s success. It also helps weed out the weak links without much management interference.

Spend money on things that help improve the experience of your customers.

Malik tells the story of how GigaOM started out of a local Starbucks near his apartment. Instead of paying for Starbucks WiFi, Malik, with the help of some friends, hacked together a solution that would extend the range of his high-speed internet connection to reach the coffee shop.

It’s an approach to frugality that still permeates GigaOM. Money is spent first on things that would benefit the customer experience, the readers.

Openness is not just a word, it is a state of mind.

You need to have a truly flat organization and in order to build an open-minded and cohesive team that laughs together, works together and learns to deal with adversity together.

GigaOM’s first offices had cubicles, which Malik says “destroyed a lot of camaraderie in the company”. “No one was talking to each other, the energy in the office hit a low point, and most importantly, it felt like work,” he writes.

The current GigaOM offices is an open-plan loft-like space.

It is good to know what you’re good at, what you suck at, and when you need help.

The toll of juggling work, learning to run a business on the fly, and constant need to update the blog, combined with serious bad habits — a two to three-pack-a-day smoking habit, crazy eating schedule and lack of exercise — created a perfect storm that resulted in me falling sick. It was my body telling me I needed help, and I needed it fast.

The decision to switch out of the chief executive’s role in early 2008 was preceded by one of those conversations with myself. What was the role I wanted to play at the company? Why I wanted to do what I wanted to do, and most importantly, what we wanted to achieve as a startup and as a business. That conversation ended with two decisions. The first decision was pretty simple, actually.

So, I went to the board (me and Jon Callaghan), and said that I was going to fire myself and bring in someone better. Instead, I wanted to focus on what I knew best — product and editorial strategy. This marriage of my wild enthusiasm with Paul’s pragmatism turned out to be just what the doctor ordered.

Find the essence of your company’s culture, core strengths and your way of thinking.

GigaOM found its rhythm when it learned that its strength lies in writing analysis and context pieces, with blog sensibilities. It also found an interesting way of charging for content without the use of a traditional paywall.

The identification of “DNA” allowed us to look at various business decisions through that specific lens. It made it clear that we don’t have to do what others do. Instead, we play our own game at our own speed, leveraging our innate strengths. We would need to take a step back from the page views-based growth and monetization approach that had plagued most major media companies. We had to find an alternative way to make money.

And because we had configured our company’s DNA, our new CEO suggested that perhaps we should think in terms of charging for content. I didn’t think it would make sense to put a firewall on what he had been offering for free. Paul said to me, “so why not build something new?” And boom, just like that, we were working on GigaOM Pro research offering.

In the early stages, Malik chose to start niche publications outside of GigaOM, but he found it “diffused the attention and intellectual energy” of the team. “It caused unwanted anxiety all around. All those sites used up our meager resources — monetary, design, engineering and intellectual,” he writes.

You have to walk before you run.

As a founder, you often don’t understand the gulf between your vision of the future and the reality in which a business exists. It is important to find the right balance between the two.

Shun consensus.

Don’t be shy about making difficult decisions. If you have conviction, zig when everyone is zagging. After all, the worst that can happen is that you fail. If you don’t try, you don’t fail. You don’t fail, you don’t learn. You don’t learn, you will have failed anyway.

People who believe in you also want to succeed.

They will work better if you encourage them, not micromanage them. Empower them to win.

Overcoming micromanaging and empowering the team to thrive is the foundation of a founder’s lasting success. It doesn’t matter when, but eventually as companies grow, a founder cannot make every decision, read every email, follow every thread of conversation and interview every new hire. What is important, is to build a culture that allows everyone to make decisions like you.

Image: Olivier Ezratty (via Wikimedia Commons)