After leaving my job to start CloudHealth Technologies, I asked several colleagues I respected in the industry to become advisors for my journey. My first advisor was Jeff McCarthy, a partner at North Bridge Venture Partners, who agreed to let me work from his offices as an Entrepreneur In Residence (EIR). Jeff was quickly followed by others, including my former CEOs, Dan Phillips, and the CTO of my previous company, Greg Arnette. Eventually my board of advisors would grow to include two CEOs, two entrepreneurs, a venture capitalist, and a startup executive. I would meet with these advisors individually, often at coffee shops near their home or work. They gave me much needed advice in the earliest phases of founding a company, filled in gaps in my experience / skill set, made important introductions, and provided much needed collaboration on what can often be a lonely journey in being an entrepreneur. While my advisors came from different backgrounds and experience, they each shared one trait: a sincere interest in my success. They reflect the truth in our industry: if you are willing to reach out and ask for support, there are always people willing to help.
When I look back on my journey, this instinctive approach to forming a board of advisors was quite possibly the difference between my early success and failure. I believe a board of advisors is a powerful technique for anyone going through a professional transformation - whether it is starting a company, changing careers, or just trying to achieve some difficult and long-sought goal. Here are the 6 steps to forming your own board of directors.
Step 1: Define the Purpose of Your Board
The purpose of my board of advisors was to provide me support and advice through the early phases of forming CloudHealth Technologies. As a solo founder, I lacked experience in many of the areas required to start a business - e.g. market analysis, raising capital, business planning, financial planning. To compensate for my skill gaps, I found people with experiences in the areas I was deficient. A successful board of advisors should not be a permanent fixture in your life, but rather a temporary team formed to help you achieve a goal. Once you achieve this goal - in my case, building the MVP, closing the first paying customer, and hiring a CEO - you can thank everyone for their support and dissolve the board.
Step 2: Find the Right People
The right people have the following attributes: (1) bring the knowledge and experience essential to achieving your goal, (2) are invested in your success, (3) are willing to make a commitment of personal time for no expected gain, and (4) are willing to tell you what you don’t want to hear. Advisors can come from many different walks of life. Some will be former colleagues, and others might be new to you and require you recruit them to your team. A successful board of advisors not only brings the knowledge and experiences you need to support achieving a goal, but also should have some diversity in their experiences. For example, I had two CEOs who came from very different experiences and backgrounds, which allowed me to get advice from very different perspectives.
Step 3: Hire Your Advisors
Once you have identified your target advisors, you need to “hire” them. By hire I don’t mean offer them some financial incentive to support you. In fact, a successful advisor should expect to receive nothing in return for being a member of your team (other than the good feeling of supporting a trusted colleague). Instead an offer involves explaining the goal you are trying to achieve, the support you desire from them, and the requested time commitment you are making. For example, I asked most of my advisors for time once or twice a month in which I could update them on the forming business idea and seek their advice on specific topics. Keep in mind the possibility your prospective advisor may say no - e.g. conflict of interest, lack of time. Also, while there is no best practice around the number of advisors to add to your personal board, you should adjust the size based on the scope and complexity of the goal you are trying to achieve.
Step 4: Meet 1x1
The majority of the time, you will be meeting 1x1 with your advisors. While some of these meetings for me would occur over lunch or dinner, more often they occurred at coffee shops. I was always very well caffeinated during this time. The typical structure of a 1x1 meeting would be to start with informal catch up, followed by a review of the progress since our last meeting, and then focusing in on one or two issues on which you need their advice on. For example, the pricing of CloudHealth as a percentage of spend came from a meeting in my EIR cubicle at North Bridge Venture Partners, where I iterated on several approaches to pricing with my advisor. The frequency of meetings is entirely dependent on your needs, but I found a regular cadence of meeting every 2-3 weeks worked well for my purpose. Take careful notes from each meeting, and always follow up with your advisor thanking them for their time.
Step 5: Meet Together
It’s possible your advisors will never meet each other. In fact, I only convened my board of advisors once. I did this when I was at a key inflection point in my early startup journey. I needed help answering two critical questions: (1) do I continue bootstrapping the business or raise venture capital, and (2) am I the CEO or do I need to hire one? To answer these questions, I invited my advisors to an evening meeting at North Bridge Venture Partners that included dinner and drinks. I had prepared a slide deck, and after introductions, we reviewed the progress of the business to date, and engaged in a 2+ hour discussion on the questions. The ability to hear multiple competing views in real-time was helpful in making my decisions. I would highly encourage anyone to consider replicating a similar approach when they reach a key inflecton point in the march toward their goal.
Step 6: Disband When Done
You will either achieve your goal, fail to achieve the goal, identify a new goal, or determine you are no longer interested in pursuing the goal. In any of these scenarios, you will no longer need your advisors. At this point, you should report the conclusion of your work, thank them for their time, and offer to repay the favor if they ever need it. While in some cases your advisors may play a broader role after you achieve your goal - e.g. one became my CEO - it is rare and should not be expected. One good karma story about advisors I like to tell is this: one of my former advisors became an official advisor to the company after we raised venture capital and was provided stock options. After CloudHealth was acquired, he received a payout for his stock. He decided that rather than using the funds for himself, he woudld put it all into starting his company. He then asked me if I would be an advisor. When it comes to boards of advisors, sometimes what goes around comes around.
Could I have started CloudHealth without a board of advisors? Possibly. Would the risk of doing it alone have been higher? Absolutely. Boards of advisors offer professionals a powerful technique to de-risk big challenges they are navigating. To anyone purusing a difficult objective, I ask this simple question: why go it alone when you can do it with a team?