6 Founder Paradoxes- Challenges to Manage, Not Problems to Solve
One of many challenges involved with being a startup founder is holding two things of a weight at the same time. Some would call it a non-dualist mindset, thinking in terms not in either/or in both/and. There are predictable paradoxes the founders must hold at the same time- it’s one of the reasons that it can be helpful to have a cofounder because while many people are good at holding both sides of some of these paradoxes, it’s quite hard to hold them all. Importantly, the way in which a founder holds these paradoxes, or doesn’t, is another big contribution to the ultimate culture of the company. How they are managing these paradoxes can sit in the blind spots of founders. Only in an organization where it is acceptable to talk about the leader(s)’s shortcomings will any inability to hold both at the same time be part of the conversation. And yet, the company needs to hold both. Take your eye off of any one of them for too long, and the company falters or fails.
To further the conversation, here is some language to talk about these common dynamics:
Challenge #1 — Humility and Confidence: Strong Beliefs Loosely Held
From the very beginning, founders have to walk a very tight rope between projecting confidence that they know where they’re going and that the thing they’re building will work and being humble and open enough to get feedback and learnings about how and where they are wrong. The founder who is so confident they don’t ask questions or listen to their customers generally fails to build the thing the market and their customers want or they fall into a predictable trap that mentors or investors told them about but they weren’t open enough to listen. On the other hand, we have lots of good things to say about humility in this world, but we can also be too humble. The leader that doesn’t have an opinion and can’t express the vision for the company doesn’t serve the people they are trying to lead. Additionally, investors are not interested in investing in someone who doesn’t have confidence in the direction they’re heading. I’ve heard this mindset called, “strong beliefs loosely held”. That means- project confidence in the thing you believe is true today, and at the same time be ready to change it tomorrow when new data or learnings become available that update your beliefs or opinions.
Challenge #2 — Optimism and Reality: The Reality Distortion Field
There aren’t a lot of rational reasons to start a new company given their historical failure rate. One of the reasons I love founders is because they are full of optimism about why their business will work despite the odds that they’re wrong and it won’t. Founders have to be the ones to hold onto the deep believe that the company will work, and yet they can’t be so delusional as to live in a world different from the one occupied by their customers and by the market as a whole. Call it a “reality distortion field”- as in the ability to see the world around you as it is and yet believe in the possibility of the thing that you’re creating. The founder that sees too much reality stumbles on more despair and hopelessness than they can manage and gives up. The founder who is too optimistic fails to make backup plans or engage in productive paranoia or adjust when things don’t work out as they inevitably don’t startups. Founders have to hold both.
Challenge #3 — Focus on Daily Work and Focus on the Vision: Entrepreneurial Vertigo
Founders have to be able to zoom in and out of their own businesses. They have to be able to see what is needed today and this week, but also where they’re going in a year or 10 years. Call it “entrepreneurial vertigo”, as in the whiplash of going between the minutia of the business and the tactical to-do lists to the largest topics the business faces and back again. It could happen in back-to-back meetings. Say your 9 o’clock call is with an investor talking about what the business can become in five years and your 10 o’clock meeting is about the press announcement happening tomorrow for a new product. The founder who can only think about the long-term vision fails to execute and stays in a dream-like world full of possibilities but lacking in reality. The founder who is too focused on execution and the short term fails to see the bigger picture, misses important changes in the market, and doesn’t inspire others with a larger mission. Forest AND trees. Zoom in. Zoom out. Try not to get too dizzy.
Challenge #4 — Control and Letting Go: The Developmental Dilemma
Founders have many decisions to make about when to keep control and when to let go. There are always more things to do then there is time to do them. Good founders know that they have to let go of some things in order to focus and have some control over the things that are most important. The founder who overcorrects on trying to control everything doesn’t make as much progress on the right things and becomes a bottleneck for making all the decisions. Founders who let go of everything also fail to provide enough focus for others to have the freedom to do their work and still be in alignment with the goals of the company. As the company grows, the founder has to let go enough so that others can learn and even fail, but not fail so much that they quit or destroy the company, but enough to take risks and ultimately grow. It’s like a parent who has to let their child fall in order for them to learn to run, but that parent doesn’t want them to fall near a set of stairs. Let go, let others learn, be ok with some bumps and bruises but have a net to keep from big falls. It’s tricky.
Challenge #5 — Chaos and Order: Navigating a Chaordic System
Building a company requires some amount of discipline and structure. Without setting some goals for where you want to go with your business, the wandering might be too far and too wide to get somewhere before you run out of time, energy or money. Even entrepreneurs who had no idea what business they wanted to build started with some boundaries around the process, and the ones that arrive somewhere had a process for investigating different business ideas. At the same time, startups can suffer from too much process, especially in the beginning when the need for experimentation and discovery is so high. Even experiments can benefit from structure (just ask a scientist), but every so often it’s important to “just try stuff”. Managing this paradox requires “just enough process” for the stage the business is at, that means navigating between having rigor and discipline and being open to how else thing might get done or get figured out. You need some of both. Entrepreneurs don’t have the time and energy to be methodical about EVERYTHING, they need to get clear on the things that most require a process for the company to be successful, and remain more flexible about the rest.
Challenge #6— Soft Stuff and Hard Stuff: When Rubber Meets Road
The hard stuff is all the tangible, measurable things in a business. Cash in the bank, measurable goals, KPIs (key performance indicators), customer support tickets, units sold, profits. It’s not easy to build a business that “works” by the numbers- one that makes more money than it spends or is projected to with invested capital. But it’s only half the business. The other half is the the soft stuff- the human side. Businesses are human organizations, which means they come with hopes, dreams, emotions, stories, egos, burdens, and so much more. Managing the human side of the company, the soft stuff, is at least as hard as the hard stuff, regardless of the size of the company. As a single founder, try managing accountability, perspective and ego. Add a cofounder and alignment and values are added. Build a team of even a few people and suddenly focus, prioritization, motivation and skillful communication are required. While the number of people added to the company grows linearly, the number of relationships within the company grows exponentially and creates a complex system. Impacting one person impacts the whole system, and suddenly founders realize that the “soft” stuff is actually the hard stuff.
