A Slice of Humble Pie

Photo by Irina on Unsplash

This may come as a shock to you, but I sometimes have a bit of an ego problem. Yes, yes, I know. Hard to believe the guy who likes to hear himself talk so much he puts it into written word and blasts it off to the interwebs on a weekly basis has an ego problem.

Point is, I think I am awesome.

And I think that this is generally a good thing. But sometimes it is a bad thing.

Following?

I have a lot of self-confidence. I truly believe that I can achieve anything I set my mind to. I am someone that likes to throw himself head first into whatever roadblocks or hurdles life puts in my way. I am a big believer in the idea that if you don’t like something that is going on in your life, stop making excuses for it and take the necessary steps to change it.

I think this confidence is good. But sometimes it’s bad.

Sometimes I can get a little bit ahead of my skiis and fall down too much on the side of “better to ask for forgiveness than permission.” This approach works well in some settings, and significantly less so in others. One of my biggest weaknesses, my tendency to de-value the accomplishments of others, stems directly from this overconfidence and the related insecurities it can cause.

Another way that this confidence can sometimes manifest itself is through eagerness to take on more. I am supremely confident in my ability to upskill and do what I need to take on more and more, but sometimes this can be at odds with my choice of career.

Venture capital is not a fire-from-the-hip industry. Or at least, I believe that it is not when done well.

VC is an apprenticeship industry. It takes time to learn the craft. Sometimes that is hard for me to remember. I want to do more and take on more responsibility and have opinions on every company and every sector. But I have been doing this for less than a year. And I have a lot still to learn.

This week I got a reminder of that after hearing more experienced investors than myself talk about board governance. What a huge responsibility it is and all the perils that responsibility entails if its gravity is not appreciated.

After hearing about their trials and tribulations on various boards throughout their career, it really struck me how much more I have to learn.

I am so excited to be in this industry.

I love working with entrepreneurs and helping them build great companies.

But it is important to keep in mind that I don’t know everything. That this industry is a craft and like all crafts it requires reps and experience before you can become a master. Rome was not built with enthusiasm alone.

I write this post not because I am discouraged. Quite the opposite actually.

When I think about how relatively inexperienced I am and how much I still have to learn, I am not demoralized.

I am not daunted.

I am not intimidated or frustrated.

Instead, I am excited to get back to work and keep learning. To keep beating on my craft.

I think that is a pretty good sign.

Board to Death

Photo by Drew Beamer on Unsplash

The world of Venture Capital is very different than it appears from the outside. I have been surprised by many things since becoming an investor, but none more so, than the difficulties surrounding boards. From the outside looking in, boards appear simple. Incentives are aligned. Everyone wants what is best for the company. Experience and expertise are leveraged to make the company the best it can be.

If only it were that simple.

Properly managing boards as an entrepreneur is a dance. Defer to them too much and you will lose the magic that made board members want to support you in the first place. Don’t heed them enough and you will make avoidable mistakes and miss out on opportunities.

The biggest mistake I see entrepreneurs make in respect towards their boards is that they think about their boards with the wrong mindset. The second you grow mistrustful of your board and start thinking of them as antagonists trying to put up hurdles in the way of your company, the chances your company is going to become successful with you at the helm plummets to almost zero.

Alright, Erik chill out. Classic Berg exaggeration.

No I am serious. A toxic board relationship is THAT deadly. It may not happen that day. Or that month. But eventually allowing the relationship between you and the board to fester will come back to bite either you or the company. Or both.

I believe the best metaphor for a well run board is to think of the board as your boss. Because that is exactly what they are. The keys to a healthy relationship with a board are the same as with a healthy relationship with your boss.

Communication

As with most relationships in life, the most important thing when managing a board is communication. Regularly update your board (even, and especially, outside of official board meetings) on your successes, failures, and any ways that they can help. I maintain that investor updates are one of the highest leverage activities any entrepreneur can do. Keep your board in the loop with what is going on with your company and they will be able to leverage their experience to help you make the best possible decisions. Note that I am not saying to do whatever your board tells you to. If they knew what was best for your business in every possible scenario, they would’ve started your company themselves. Rely on your intuition. It got you this far. But your board has many lifetime’s worth of additional experience than you do. Use it. Take it into account and leverage it to make the best possible decisions. To do otherwise is simply foolish.

Coaching

Just like all good bosses, boards have a responsibility to develop the CEO. Most startup entrepreneurs have not built a business before. Those that have, in all likelihood, have done so in a different sector or space. The board has a responsibility to coach and mentor the CEO to be the best that they can be. This means giving your CEO the tools they require to be successful. Equip them with resources and connect them with mentors who have been successful in this space before. A board’s fundamental job is to protect the interests of a company and its employees. The best way to do this is by making sure that the CEO performs at their absolute peak. If you as a board member believe your duty is to provide oversight without nourishment, advice without mentorship, you are neglecting your responsibilities to the company.

Accountability

Communication is a two way street. Yes, the impetus lies squarely at the feet of the entrepreneur, but at the end of the day, they will only feel empowered to bring everything to the attention of the board if the board knows how to give appropriate levels of feedback. Successful boards design structures where they can hold their CEOs accountable in a constructive way. I think Fred Wilson has the best approach for ensuring that feedback loops are tight and honest. Entrepreneurs, don’t get defensive when the board gives you feedback. Every single one of their incentives is aligned with the success of the company. So are yours. Remember that they trying to help you make the company the best that it can possibly be.

From the outside looking in, no one will know how healthy your company is. You can survive with a bad board relationship for a little while. But, if you are consistently neglecting your relationship with your board, eventually it will blow up in your face. The key is to leverage their experience and remember that they are on your side.