Being a startup founder is hard, tough, frustrating and rewarding – possibly all within the space of a nanosecond. And yet, it is like a high none other. I have experienced it in others. And quietly, I have lived it for over six  years. Here are some lessons I learned from my journey. They may not be universal, but these lessons learned have changed me both as a person and as a founder — Om.

We recently wrapped up our strategy offsite, an annual event that brings together the members of our very distributed team – 12 different cities in four different countries – to discuss what our aspirations and ambitions are for the coming year.

It is also a good time to reacquaint members of our growing team with who we are, what we believe and why we do what it is we do. But most importantly, it gives me a chance to reassess myself, both as a founder and as a member of the team. It is an opportunity to hold myself accountable to people who believe in me, my vision and are helping me realize my dreams.

As part of the strategy gathering, Paul Walborsky,who is GigaOM’s chief executive, asked me about the company’s ethos, principles, what I think about us as a group, and the world at large. It is something I talk about often, but mostly with my team members and in one-on-one conversations.

At GigaOm, we are story tellers. And I believe that as story tellers, we should never really be the story. Sure, we can make an occasional appearance, but less is more. It is still hard for me to think of myself as anyone other than a teller of other people’s stories, but some entrepreneur friends have nudged me to share what I have learned as a founder. To tell my story. So here it is: the evolution of me as a founder and how I see myself and the industry continuing to morph in the months, years and hopefully decades to come. I’ve divided it into four parts:

• Starting It Up
• The Founding Principles
• Building, Learning, Evolving, Improving
• Are You Winning As a Founder?

Here is the TL:DR version in case you are pressed for time.

STARTING IT UP

Photo courtesy of Scott Beale of Laughing Squid

I had been writing GigaOM (the blog) since December 2001, but in 2003, I started working on a piece for Business 2.0 called The Rise of a Insta-Company, which theorized that open source, cheap bandwidth and increasingly falling cost of infrastructure would result in companies being built at a dramatically lower cost than ever before.

The more I wrote about the oncoming mobile and broadband revolution, the more obvious it became that the print media was going to fight for attention with cheaper, faster publications. Faster networks meant people would be able to access information anytime, anywhere, on any device. Blogs were part of the shift to a more intimate, frenzied, and on the go media landscape. I knew I had to leave Business 2.0 before the opportunity left me behind. Conversations with some of my fellow bloggers (thanks Rafat and Mike) only convinced me that it was time to jump into the deep-end. Funny, because here I was telling others to start blog-based businesses.

But it was a conversation with Toni Schneider (now CEO of Automattic, the on-demand WordPress service), and a venture partner at True that made it all come together. I remember him asking me: what makes you happier, writing for GigaOM or Business 2.0? The answer was obvious to Toni, but I needed to answer that question for myself. And when I did, other decisions came easy, though telling my boss was not.

By 2005, it became clear that more people were reading GigaOm than they were reading my then employer, Business 2.0. Maybe it was timing (as it was the early days of blogging), or maybe it was because I had something to say. I am still not sure, but the trend was clearly my friend.

Before I started GigaOm (the company) in June 2006, I had never really worked for a startup. The closest I got to having a startup experience was being a member of the founding team of Forbes.com. Sure, I wrote about startups all the time, but my work experience with a classic Silicon Valley-styled startup was non-existent.

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.

In May 2006 when folks from True Ventures gave me the check (with a message on the back saying “go make your dream come true”), 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.

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.

Lesson Learned Be completely honest with oneself and take time to self reflect before making big decisions in life.  

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THE FOUNDING PRINCIPLES

Starting up was a nerve racking experience, mostly because I had no idea what I was doing. However, as a wise man once said, every man (and woman) has to have principles. So should startups. My view is, from the Ten Commandments to the American Constitution, there have always been guiding principles that have survived the test of time, so why shouldn’t there be one for your startup? While it is commonplace to find wisdom about “the process of the startup,” we should not forget the foundational values of a startup and the DNA of the company you are building. The four founding principles guiding GigaOm are:

1. Be self aware of your strengths and weaknesses.
2. Be transparent and honest with those whom you work.
3. Be respectful and decent to others if you want others to be decent and respectful to you.
4. Build a true, peer-to-peer management culture.

These are not stratagems. They are not a mission statement. They are not a vision statement. But they are founding principles. Values that would define us not only as people, but also a living organism called a startup. 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.

Lesson Learned: 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.

Lesson Learned: 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.

Lesson Learned: 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.

While the four founding principles were key in helping figure things out, what I learned over past six-and-a-half years has been equally influential in my thinking, my evolution as a founder and most importantly, as a person.

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BUILD, LEARN, EVOLVE, IMPROVE 

My early believers + that Kevin Rose dude.

Katie, Liz and I put up our virtual shingle at a Starbucks near my apartment. (Ombucks link on Starbucks.) I was so cheap that instead of paying for Starbucks WiFi, I hacked together a solution with help from my friends at Meraki to beam my super-fast broadband (20 Mbps at that time) via WiFi down to the Starbucks from my apartment.

That approach to frugality still continues, by the way. We spend money on things that help in improving the experience of our customers, our readers. The day we lose this focus on readers is the day we have failed as a collective.

This is the view from the Starbucks, my first GigaOm office.

We put roots down at Pier 38, then Pier 1.5, but it was a miserable experience. There were lots of cubicles, which 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.

This led to the decision to move to our current offices in SOMA — a big loft-like space that is completely open. In fact, exactly two people have offices at our company — NYC-based executive editor Ernest Sander, and chief executive Paul Walborsky, and only for face-to-face meetings sake. I know it would be time for me to leave, and that I would have failed our company culture if we started erecting walls between our team members.

And so we built our company.

In the early days, my belief was that blogs (or as I called them micro-pubs back in 2002) would grow really fast and it would allow me to aggregate large subsets of audiences around specific niches.

I decided to launch WebWorkerDaily in 2006, because it was obvious to me that distributed work was an eventuality we could not escape and soon, will live in an on-demand world that would extend from music, to movies, to work related software. I was also pretty convinced that we would live in a world where online video would be pervasive and so we started NewTeeVee in 2007. I was also convinced that the cambrian explosion in startups would mean there would need to be a place for startup founders to exchange wisdom and knowledge with each other. We started FoundRead. And then we started Earth2Tech.

It turned out that in all those cases, I was a few years too early. The new brands essentially diffused the attention and intellectual energy of our team. It caused unwanted anxiety all around. All those sites used up our meager resources — monetary, design, engineering and intellectual.

The niche audiences were slower to develop, and advertising support never really showed up. As a result, we had handful of blogs that garnered a passionate audience, but none that was not big enough to become a business. It doesn’t matter that in the long term, I was eventually proved right, because the cost of being too early was too high. And I don’t mean in monetary terms.

I got away with launching those sub-brands/blogs was because of my history as a blogger. Everyone went along with my decisions because they made logical sense, even though I clearly needed to stop drinking my own brew of wild optimism.

And so we learned.

The toll of juggling work, learning to run a business on the fly, and constantly 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.

• I sucked at the day-to-day business stuff.
• I found it hard to deal with advertising related stuff.
• I found it difficult to recruit the right people outside of the editorial team.
• I wanted to write.
• I never wanted to put the company and its future in jeopardy because of my own shortcomings,  physical and otherwise.

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.

And we evolved.

Since then, we have consolidated our efforts into building a single brand with a handful of sub-brands and I am glad we did. There are no sub-teams, just one brand to nurture under a unified message and mission.

As broadband became faster, the speed of publishing would get faster. It was clear as day, even back then, that in our ever-faster, post-Twitter world, the only way to differentiate ourselves would be to focus on our core strengths — analysis and context, but with blog sensibilities.

It had been a mantra that I had been unknowingly sharing with our slowly growing team of writers, but wasn’t putting into practice before I fell sick. However, a life changing event is a good time to pay attention to oneself. It helped the ideology to take root within our company at a much deeper level.

My always-positive friend Jennifer Reuting puts it well when she says “if life gives you lemons, make a mimosa.” While it was a time of great adversity, both for me, our tiny startup and our still-forming team, it was also the luckiest break. We had found our company’s DNA.

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.

And we improved.

Lesson Learned: 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.

Lesson Learned: It is good to know what you as a founder are good at, what you suck at, and when you need help. And sometimes that means replacing yourself as the CEO.

Lesson Learned: Work hard to find the essence of your company’s culture, core strengths and your way of thinking.

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If life gives you barbed wire, figure out a way to make wine

ARE YOU WINNING AS A FOUNDER?

The success of business can be measured through many metrics — page views, revenues, profits, the number of employees, or an exit (either through a private or through a public sale). But there isn’t really a scorecard for a founder. You don’t really know if you are winning, losing, succeeding, or failing. It is actually pretty much all of those, all within the firing of a synapse. The success of a founder, as far as I am concerned, is measured in intangibles.

From the day I started till very recently (aka December 31, 2012), I can literally count the days when I have slept solid eight hours. Let’s just face it: you need 48 hours in a day to do everything you need to do, so sleep is hardly a luxury a founder can afford. Considering you have a tiny team, you don’t have much choice but to do anything and everything.

That early experience actually conditions founders to be in an always-on, always-working mode, even as the company grows big. It also turns us into micro-managers. I know I was one, constantly meddling and pushing and not trusting the decisions made by the team. My micromanaging wasn’t a conscious effort – it just is a behavioral tic. Just like my brain was programmed to smoke every few minutes, the meddling had become an ingrained behavior.

As a founder, that constant micro-managing is the single worst thing you can do to your startups. If you don’t let people on your team try new things, you curb their enthusiasm and slowly impede the startup spirit. I still get up in pre-dawn and pepper editorial team with dozens of pieces I have read that I think they should read. (I know, even I would roll my eyes if I got those.) Product team gets a dozen new features and an equal number of tweaks every second day. Our CEO gets new business ideas and our editor in chief hears from me when I find something wrong.

Yes, those emails and message are annoying and disruptive, but I also believe it is the role of the founder to push the creative boundaries and capabilities of the team. The trick is in finding ways to be constructive and not destructive and disruptive. Now, I am working hard on only sending and sharing ideas that help the individual team members succeed in what they do. It is my one resolution for 2013: less annoying emails. Some day, I will overcome this founder’s dilemma.

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.

Scary? You bet it is, because you become less important as a founder. Our ego doesn’t allow us to deal with such reality. But that is the real metric of success as far as I am concerned. If the first ten members of the team understand the company DNA, then they are going to help build the future team based on that core value proposition. If your DNA is peer-to-peer intelligence sharing and mentioning, then you can be assured of longer-term talent development. That is the ultimate victory for the founder.

I had one of those moments this past week at our offsite. I spent time with a lot of our team members. None of them were hired by me, and instead they were picked up through a peer-review-hire process. They felt right – just like the first few. I smiled to myself. I can now just focus on writing and mentoring.

Lesson Learned: 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.

Lesson Learned: 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.

Lesson Learned: People who believe in you also want to succeed. They will work better if you encourage them, not micromanage them. Empower them to win.

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Thanks to my friends Arjun, Hiten and Kristy  for encouraging me to write this post.