The Founder’s Paradox: How to Succeed When Most Founders Fail

Every summer I go on a backpacking trip to the Sierras in California. This year it was to the Emigrant Wilderness, just north of Yosemite. Jagged granite peaks, ice-blue lakes punctuated by ancient windswept trees, open meadows flush with wildflowers — it is an awesome place.

Several close friends typically join me for the trip. And as anyone who has hiked this region knows, it can be very challenging terrain. The weather patterns, even in the summer, can be violent at the higher elevations.

This time we went in from the Kennedy Meadows trailhead off of Highway 108 and cut cross-country at Summit Creek. We camped under Granite Dome at Upper Lewis Lake. There was still deep snow in the northern-facing areas.

Our group included a friend who had left his role as the SVP of product for a major technology company after being there for almost seven years. As part of exploring what he wants to work on next, he had been meeting with CEOs and company founders — more than 50 in the last six months.

I asked my friend what (if any) patterns he noticed among the founders he had spoken to at the companies that he thought were doing exceptionally well.

I was especially interested in my friend’s perspective because of the diverse group he had been meeting with and because I know that he likes to get to the essence of what people and businesses are all about. So there, in this spectacular setting, we talked about what it takes to build meaningful companies when so many founders fail.

My questions were specifically about long-term growth and lasting success for customers and employees. Obviously, I was less interested in companies that were losing hundreds of millions of dollars to make a lot less. Which, unfortunately, seems to be far too common.

This is an important distinction — anyone can start a company and even make a lot of money. Not everyone creates lasting, sustainable value that puts people first.

The following is a compilation based on those conversations and what I have learned over the last 20 years in Silicon Valley, building and serving as CEO for three successful technology companies:

Pursue one goal “First one focus, second one free.” This is a favorite saying of mine. I actually said this just the other day while speaking with a group of industry analysts about how our team at Aha! is able to stay on track. The meaning is really quite simple: Pursue one goal exceptionally well and opportunities will follow. The key is that you must continuously, even obsessively, measure progress — because you can only improve what you measure. The results will tell you whether you are working on what really matters most to achieve that goal.

Codify your values What do you stand for? Knowing your values is important. This is where many founders falter — knowing and doing are two different things. So, you also need to write down and codify those values if you want to build something lasting. This will force you to distill each principle to its very essence and allow you to provide a decision framework for others. It also does something else. Written values are a trusty night guard, always watching. Accountability which will inspire you to stay true even when no one else is looking.

Have sustainable passion Oftentimes, this passion is not solely about the technology or innovation. You need to be excited to work while on vacation. To wake up early and rush to see what is sitting in your email inbox. For the commitment and effort required to be sustainable, you need at least one unbreakable passion that ties you to the business in a deeply personal way. For example, what sustains me is changing how companies build products and changing how a high-growth software company can be built.

Study the errors Success is built on the shoulders of struggle and learning. This is true for all major accomplishments. If you are a first-time founder, you need hyper-awareness of what is not going well. The ability to learn from the low points is particularly important. You do not have the past to lean on. So you cannot fail fast and move on — to rise, you must deeply understand what went wrong.

Work relentlessly Yes, you have a family and friends and hobbies. Of course, your health must come first. But to be successful, you will spend more time working on your business than any of those areas combined. And some aspects of what you did before you were a founder will need to be sacrificed. Working relentlessly is not the same as being passionate. It is more about being disciplined and honest with yourself about how dedicated you will be. This work does not end with the first taste of success — if anything, the drive must intensify. The journey requires unending stamina and big effort.

Support others No one achieves anything in life entirely alone, much less building a successful business. So while founders are often the face of the company, you need support from others who care equally about the vision and how to grow the business. You also need to know when to put others first, when to be demanding or understanding, when to throw praise or take blame. Some of this comes from self-awareness, but it also comes from your values, your passion, your goals, and your ability to learn from the past.

Allow it to define you “Founder” is a unique and special title that sticks with you. The opportunity to see and help build something new is an honor. It should humble you. Feel the magnitude of the opportunity and responsibility and let it fuel you. I am not talking about getting caught up in hype — that is a quick path to self-defeat because hype is not lasting. Embrace the paradoxes you will face every day. Relish the work. Allow it to define you.

So many founders falter and fail — far more than successfully achieve what they thought they could.

Every true wilderness backpacking trip has its own contradictions. The deep conversations and isolation. The beauty and violent storms. The magnificent views and bouldered gulleys.

But for me, it is just another reminder of what happens when we encounter two seeming opposites. Some people simply see the paradox. Others choose to boldly walk off-trail — right through it.

Read more of The Founder’s Paradox.