7 lessons learned scaling up

, 1,101 words

I was asked to write a short piece for Fortune magazine on what I wish I'd known before I started my businesses. That got me thinking of the seven lessons that have meant the most to me on my entrepreneurial journey. Here's what I wrote:

Starting a couple of my own companies over the years has set me on a challenging, but deeply rewarding journey, and I’ve learned a handful of hard-won lessons along the way. Advice for entrepreneurs is often reduced to absolute statements and black-and-white “do’s” and “don’ts,” but I’ve found the truth is more nuanced. Some fundamentals — such as values — are critical, yet often overlooked. Here are the lessons that have meant the most to me on my entrepreneurial journey:

  1. Advice can be unhelpful. There are thousands of incredible books and blogs on the many aspects of building a business, and while it can be tempting to shortcut learning on your own by asking other entrepreneurs what to do, their advice might not always fit. Developing core competencies — such as one’s ability to learn — is more valuable in the long run.

    A number of large companies have programs offering advice from their staff directly to startups. But might working at a large company be a negative qualifier for advising entrepreneurs on starting up? Processes that work well in one company may not work in another, especially one that’s at a different stage. I have found value in seeking out stories of others’ experiences, as well as sharing my own, rather than looking for explicit answers.

  2. Entrepreneurs aren’t a different breed. I’m not an “intuitive maverick,” born with “the entrepreneur gene.” Like many business owners I’ve met, I used to think that entrepreneurship was for other people. I thought that business owners were domineering personalities. (Perhaps I watched too much TV.) I believe that many future entrepreneurs don’t yet know their own potential.

  3. Focus is one of the hardest disciplines. As a founder, the role one must carry out in a company changes as the company grows. One of the best phrases I’ve read on the subject was the value of working “on” rather than “in” the business. At the start, it can be important to work on delivery, but to grow to the next stage, an entrepreneur typically has to focus on the business itself. Jim Collins’ book Good to Great illustrates a number of these on-the-business characteristics.

    Entrepreneurship has gained increasing profile over recent decades and has come to be celebrated as something of a lifestyle. It is hard not to be distracted by the fear of missing out (“FOMO”) created by well-publicized entrepreneurs. Is one in the glitziest members’ clubs, raising investment from the most popular firms, and connected to the splashiest founders? As with time spent chasing competitors, time spent getting into a scene is time lost from building a product and a business. That’s the goal not to miss out on.

  4. Values—surfaced well—are a huge help to building an organisation. Fairly early on in the journey of building Reincubate, we took the entire team abroad on a company holiday and spent an afternoon coming up with company values. This feel-­good session produced a set of platitudes which were quickly forgotten. It was only upon reading Verne Harnish’s Mastering the Rockefeller Habits that I came to truly understand the power and utility of core values.

    I surfaced what mattered most to me in the business, and worked to understand and communicate more readily why I was building it. This led to a refocused set of values, which have been instrumental in decision-­making around strategy, product, recruitment, and operations. That book has been one of the most valuable inputs for the business.

  5. Relationships with non­competing peers can be incredibly valuable. Entrepreneurship is a lonely journey, and it isn’t always easy to find perspective when faced with a new problem. Entrepreneurs can be beset with challenges around finance, management, strategy, and morale. Family, partners, or friends are rarely neutral, qualified, and non-judgemental, and they’re often eager to advise or tell one exactly what to do. Advice is easy to give without accountability, especially on loaded topics.

    I was fortunate to find the nonprofit learning group, the Entrepreneurs’ Organization (EO). From EO, I gained a forum of peers who I now share my ups and downs with, learn from, and benchmark performance against. For me, this has been both a critical release and a valuable source of learning and inspiration.

  6. Big, unprovable product investments tend to go wrong. I spent over $1 million trying to build a company that failed. I didn’t test its ability to monetize early enough. Even simpler missteps — such as replacing an important website all at once with little testing, rather than bit by bit — can cost valuable time and can set back a company’s progress. My most commercially successful projects have always sprung from the back of simple prototypes, assembled in a few days.

  7. Getting a perfect “fit” with each new hire is impossible. The Dunning-­Kruger effect describes a cognitive bias where individuals lack the skills to understand that they are out of their depth. Addressing this too late is unfair to the employee, their colleagues, and the company, so it’s important to tackle it. Ben Horowitz’s book, The Hard Thing about Hard Things, has a number of insightful reflections on getting this right.

    I’ve learned two useful techniques to follow as the team grows. The first is to award new hires with as much trust as possible and as rapidly as possible. Rather than giving them simple tasks, I set more challenging ones and expect them to deliver in their first week. This gives them a sense of autonomy and mastery (two of the three attributes illustrated in Dan Pink’s book, Drive) and gives a real demonstration as to the current limit of their capabilities. The second technique is a simple reflection at each stage as they progress: Would I hire that person again, knowing what I know now?

Aside from these, there have been many other important lessons for me, and I am sure there are more to come. That promise of future learning — and the challenges that will come with it — is one of the most exciting parts of entrepreneurship. I’m looking forward to that learning, and to sharing my experiences with others where I can help them in turn.