I Helped Build 5 Companies before 34 and This is The #1 Mistake First time Founders Make

The debate was deadlocked. Three members of my team at Kanary—the platform I’d built for brands to buy digital ad space—agreed with me, and three didn’t. It was 2013, and I’d spent the last year building Kanary as the company’s founder and CEO.

I was trying to break the deadlock, deciding whether we should pursue a new targeting function or not, when I looked down at my phone: I had 47 notifications from Amazon Web Services. Our load balancers were failing. I had forgotten to schedule an infrastructure review to handle new client volume. 

I’d been so busy trying to retain control over every decision made at Kanary, that I’d let key responsibilities slip. 

In that moment, I broke a cardinal rule I’ve always strived to follow: You can’t control everything yourself. As your company scales, you have to delegate responsibility, and empower your team. You have to let go.

But, that rule is hard not to break. In fact, it’s the No. 1 mistake most first time founders make, without even realizing it.

In addition to founding Kanary, which was acquired in 2014, I’ve worked at four other startups, as a founder, a co-founder, a CMO, a CPO, and all functions in between. In 2015, I became CMO at Smarkets, a betting platform that I helped grow to over $2 billion in transactions per year in less than 12 months, and later CPO at Lyst, a fashion marketplace with over 75 million customers.

Today, I’m a co-founder of Rho Business Banking, offering digital business banking for SMB’s, and an angel investor in early stage technology companies. 

Over my career, I’ve met, worked with, and counseled countless founders. And although the industries, verticals, and market segments vary, I’ve seen it all too often: Even experienced founders struggle to let go.

Naturally, there is a strong pull to retain control over every decision made at your company—even as it scales to dozens and hundreds of employees.

For me, success as a manager, leader and founder, comes not through the ability to control and oversee every function, but the ability to empower your team to make the right decisions in your absence.

The best founders actively seek to share and distribute responsibility, and spend their time creating systems to ensure teams are set up to succeed at handling those responsibilities.

And while putting your company, your success, and your reputation, in the hands of others can be terrifying, it is the only way to build a company that will survive the growing pains of scale.

So how do you do it? I have three pieces of advice to help get you started.

1. Start with a single task

At Kanary, I developed a system to practice letting go. I would identify a task that was incredibly important, but universally understood, without too many unknowns, and hand it over to someone. I’d make sure it was a mission-critical task with high stakes—no chickening out—but nothing too nebulous or ambiguous.

Then, I would purposefully schedule a meeting for something pretty far out on the roadmap, or simply take a walk—whatever it took to avoid meddling in the details, and utilize my new found time to hone a forward, long term focus.

Whether the task was executed correctly or not, it gave me an opportunity to practice my role as a manager, rather than an operator. Instead of doing the job myself and living with the outcome, I would sit down with the employee who executed the task, and seek to understand the outcome.

What worked? What didn’t? How could I set them up to perform better on the task the next time? 

Then, answering those questions became my full-time job.

In the early days of a startup, your job is to do everything. But as your company scales, your job shifts to becoming a propellant for your team. Practice letting go of tasks as you hire your first five employees onward.

2. Encourage self-management

As your company scales to dozens of employees, you’ll need to implement a more robust system of governance and culture. In a modern startup today—which is likely geographically distributed, lean and non-hierarchical—one of the most successful systems of governance to build is one that encourages self-management.

I first learned how to build a culture of self-management among startup employees during my time at Smarkets.

Jason Trost, the founder and CEO of Smarkets, religiously practiced “self-management,” something that I have since brought with me into every other organization I’ve helped develop.  Not only did Jason encourage me to take responsibility as I wished, and shape my own role as his partner and chief marketing officer, he implemented the same leadership strategy across the whole company. There were no managers. 

The team invested heavily to implement a system of self-management, encouraging employees to work as a distributed team of individuals, able to make decisions for themselves, rather than ask permission from superiors. 

The steps to build this type of culture are relatively simple, but all consuming—you have to commit 100 percent.

First, you need to make sure the level of trust among members of your teams is extremely high. Would you loan your car to anyone you work with? Would you give them your credit card? If not, you need to take steps to increase the trust until you can confidently answer ‘Yes.’  Trust is the basic binding component in self-management, and if it’s absent at any time, you’ll put your business at great risk. In order to increase trust, continue delegating high stakes tasks to other people, and build a process around sharing feedback. 

Next, take multiple days out of the quarter to get the entire company in a room. The goal is to drive consensus around your company’s purpose, and get everyone on board. The process should be collaborative, and not a top-down recitation of instructions.

As everyone contributes, and feels heard, the process will start to bind the team together. Team members will feel more ownership about the direction of the business. This can be challenging, as a chorus of differing opinions can emerge, but that’s okay.

Spend time working through the feedback and opinions your team members share, until you can confidently say your purpose is established, and everyone agrees to it. 

Successfully following these two steps will give you a superpower: The ability to let your employees work on problems as they see fit. Sharing that freedom should result in multiple people working on the same challenges from different perspectives, dramatically increasing the chances you solve those challenges. It will increase your velocity, and you’ll be able to execute faster, and stay ahead of the competition.

At Smarkets, the results spoke for themselves: I joined at 17 employees, and by the time I left we had over 100 people. We went from trading £1 billion over the company’s seven year history, to £2 billion per year in 2016.

3. Solidify your mission

When headcount approaches hundreds of people, you will simply not have enough bandwidth for one-on-one time with every employee. At that stage, you have to double down on creating a strong culture to make sure each employee is operating at peak performance.

In order to best retain focus across your organization, crafting a simple, understandable mission statement is paramount. At Lyst, our mission was understood across product, design, PR, marketing; the entire company. Lyst’s mission was: Help customers find and buy the fashion they want, at the right size and right price.

That mission became a litmus test to determine if your work was contributing to the company’s overall success. You could ask yourself, “Is this project helping people find and buy the fashion they want at the right size and price?” If the answer was no, you could quickly change course. The mission was so clear it became ingrained in everything we did.

As your company scales, writing a clear mission statement to provide structure and cohesion across teams becomes one of the greatest single responsibilities of a founder. It drives PNL. It drives employee satisfaction. And ultimately, it drives how well you serve your customers. 

If you can’t clearly communicate a mission to your team, how can you possibly serve hundreds, thousands, or millions of customers? A clear mission statement is critical to keep all of your employees focused, and empowered to make the right decisions.

Today, at Rho Business Banking, I strive to implement all of these strategies, along with my co-founder Everett Cook. We operate in an open, transparent framework that enables us to scale fast and serve our clients even faster.  We start with trust, reinforce it with delegation to encourage self-management, and maintain a clear mission statement at all times: Helping clients reach their full potential through best-in-class business banking.

Empowering your team members to take on greater responsibility can be daunting. But with a bit of practice, a culture of self-empowerment and cohesion around a driving mission, you’ll be on your way to scaling a business built to last the test of time.

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