Chapter 13 - How to Leverage Advisors and Investors
DIGITAL COMPANION
Chapter 13
How to Leverage Advisors and Investors
“Search well and be wise, nor believe that self-willed pride will ever be better than good counsel.”
— Aeschylus, ancient Greek playwright
There is no aspiring entrepreneur worth their salt who does not harbor an idea for the ultimate “dream team” of advisors broadly defined: engaged investors in general and trusted Advisory Board members specifically.
But as many a sage has remarked, dreams can become reality only when you wake up and roll up your sleeves. And all too often in my experience, entrepreneurs fail to convert their dreams of a robust circle of external collaborators into a consciously chosen, deliberately managed, and trusted circle that is a true force multiplier.
So I need to dwell on this dimension of your journey as I’ve been fortunate to have several “dream teams” of great external collaborators, particularly at both Bazaarvoice and now at data.world.
It’s hard to say why building a broad support team eludes so many entrepreneurs. There are plenty of studies, books, and legal reviews on how to recruit and manage your Board of Directors. But this is a different subject than that upon which I wrote in Chapter 12, The Importance of Reference Checking. With corporate governance a growing issue and directors’ legal responsibilities evermore complex, the attention is important. Nonetheless, there is not commensurate thought given to the ongoing ways investors and advisors are important members of your extended team once vetted and squarely in your corner. My own view on this is that investors are narrowly seen as the source of capital. And advisors, meanwhile, are too often seen as an image-building tool, the means to bolster the perception of a startup’s competence and expertise. While raising money is obviously essential, and shaping perceptions of your company is critical, this limited outlook misses out on so much potential for your startup.
So if you’re an entrepreneur at the start of your journey, I encourage you to think broadly of your “external” team, and below I’ll also offer some advice on how to manage this team and vigorously communicate with it.
But first, I’ll invite you to imagine three intersecting circles, a Venn diagram akin to the Olympic rings. We’ll call them circles A, B, and C. In circle A, you have your investors. In circle B, you have your advisors. And in circle C, you have overlap: the investors who do function as part of your inner circle and advisors who in some cases choose to become investors.
Let’s start with circle A, your investors. You need their money, to be sure. But ideally, you should be seeking a lot more, including their experience, their domain expertise, their networks, and their insight. A good (and common) example of the wrong kind of investor is physicians. Usually, they are wealthy. Often, they are looking for places to invest. But unless your startup is in the medical space, or you're a “Stage 1” entrepreneur (see Chapter 5, Bootstrap or VC?) with a limited remit of consulting or services, these are not the investors you want to prioritize first. As so-called “passive investors,” they are not going to open doors for you or help you overcome blind spots.
That is to say, you need to be as selective as possible. You need to have empathy for those from whom you raise money. And they, in turn, need to have empathy for you, your vision, and your mission. Sure, investors are not the “man in the arena” in my often quoted phrase of Theodore Roosevelt, and they’re not going to take the arrows, nor experience the thrill of victory in the same way as you. But, they can be very supportive should you choose to treat them as part of your extended team. They are putting their money (if they are angel investors), or their investors’ money (in the case of venture capitalists), into your venture. And you should treat that capital as if it were your own. Part of the thrill of investing is to see the entrepreneur succeed, both changing their life and many other people’s lives in the process. Investors enjoy telling their friends — other investors and family — about the success of your business. The journey is more important than any return they get (although to be clear they don’t want to lose either their money or their investors’ money). The more they help you, the more they live vicariously through you, and their fingerprints will be all over your business. This is called a “helper’s high” by my good friend and CEO coach, Kirk Dando, about whom I’ll have more to say in Chapter 14, Seven Lessons Learned on the Journey from Founder to CEO.
One way to think about investors is that they are on the periphery of the arena and ready to assist you. If you think of a coliseum, imagine that you and your team are the folks “in the arena” (again, a nod to Theodore Roosevelt). The spectators, meanwhile, include many people — the press, industry analysts, as well as current and potential consultants, employees, clients, partners, and investors. Though your current clients are present, I wouldn’t necessarily say they are all in the arena with you (although some of the early adopters most certainly are) — and they deserve frequent communication as well. But let’s stick to investors and advisors in this chapter.
Your investors often have valuable tools for you to leverage in the coliseum, such as their contacts or lessons they’ve learned when they used to be the ones in the arena themselves, or from learning through one of their other investments. This is what venture capitalists call “pattern recognition.” So it is not only smart to be empathetic toward your investors because you want to build a relationship with them, but also because they can really help you. To assume otherwise is either arrogant or ignorant. When I bring up this topic in speeches or when coaching an entrepreneur, I usually get a reaction of, “What a good idea.” This tells me that the primary problem is ignorance — those entrepreneurs just haven’t been educated on this topic, and that is why I emphasize this so strongly. As far as the arrogant, they are usually in for a hard fall.
When it comes to circle B, your Board of Advisors, most of the same lessons apply. You can just substitute investors with advisors above. Both are compensated to help you — investors through ownership of some of your equity and advisors through stock option grants that they can exercise at a later period of time. A key difference, however, is that Advisory Board members are often less familiar with you, and you’re less likely to have worked together or interacted before. So many of the lessons we discussed in Chapter 11, The Proven Way to Hire Well, are relevant here. You should scrutinize, vet, and research the backgrounds of Advisory Board members before engaging them. Examples of the advisors I have brought in because they were the most strategic include investor and podcaster Mike Maples, Jr., VC and philanthropist Josh Kopelman, serially successful Wharton entrepreneur Steve Katz, Performics Founder Jamie Crouthamel, Fyrfly Venture Partners Co-founder and long-time angel investor Julie Maples, entrepreneur and angel investor Ralph Mack, and one-time Google executive and VC Satya Patel. Many of my advisors have been recruited with a more specific purpose, such as marketing know-how (particularly at Bazaarvoice with its marketing-oriented solutions) or experience in getting into a new industry (like financial services) or geography (like Europe).
As far as managing Advisory Boards, I tend to invite a subset of Advisors to an occasional Advisory Board meeting (usually every six months). To invite all of my advisors to a regular meeting risks it becoming unwieldy. This would mean, in my case, having something like 60 people in the room and little commonality in terms of the way they could help the company. Some companies avoid this by keeping the Advisory Board small. But limiting membership is a problem in its own right because some advisors you add for very specific purposes. Keep in mind that this should be a diverse group, really a collective of many sub-groups with different kinds of expertise that you will need to draw upon selectively.
In circle C is where the two groups overlap, as they should. The best way I can illustrate the fact that the lines in my imaginary Venn diagram are highly porous is with the story of my friend Dean Allemang, who has been a data.world advisor, investor, and is now an employee as well.
In our realm of data and digital technology, Dean is a powerhouse. Not only does he have a doctorate in artificial intelligence, but he is also the author of the seminal 2008 book, the Semantic Web for the Working Ontologist. The book, now in its third edition, uses the life of William Shakespeare to explore the application of the concept-connecting “semantic web.” Before we even publicly launched data.world, we sought out Dean for his counsel, and particularly his validation of the ideas and concepts we were bringing together under the flag of our new company in 2015. I and my three co-founders spent almost two days with Dean, brainstorming, shaping, and refining our plans for the company. Needless to say, Dean became one of our first Advisory Board members. Later, Dean decided to become an investor and took an equity stake in data.world. Then, in the summer of 2021, he decided to join us full-time. He is now our Principal Solutions Architect and an invaluable member of data.world’s executive team.
So, you say, “This is all interesting, but how do I manage such a disparate, dispersed, and loosely connected team?” The answer is an unusual communication practice with our investors and advisors. I treat them as I would want to be treated if I were in their shoes. It’s the Golden Rule in action.
So ask yourself: “If this were my money, what kind of updates would I want? ” My guess is you would want to always know how the business is doing and how you could help the business — and therefore help your investment. And this applies to all advisors as well so they get the same emails I send investors.
This is with the caveat that your communications will become constrained by insider trading regulation once you file to go public. As I did with Bazaarvoice in 2012, you should be as broad and transparent as possible with investors and advisors about the state of the business.
In the past, I’ve routinely written as many as three emails a week to this group. Now, I am religious about sending a detailed data.world update to all of this extended team every Monday. My updates included new client wins, major client launches, big up-sells, new executive hires, new marketing campaigns, challenges that we needed help with (such as a client contract renewal or a blocker at a client that was preventing them from properly adopting our nascent solution), new product launches, etc. For example at Bazaarvoice, I would send an update of a major client win, such as OpenTable, and get an email response from one of our investors who was friends with the CEO. Then instead of being a low-level sale, we now had high-level adoption to help drive further use of our solutions. This was especially important because our solutions needed to be evangelized to educate the client on business practices they should change as a result of having access to online word of mouth from their most valuable stakeholders — their customers — for the first time in their history. This is where the Bazaarvoice mission statement of “changing the world, one authentic conversation at a time” came from.
To reach a lot of investors simultaneously, the most efficient method is email. But then once they respond, the most efficient method is to call them, such as in the OpenTable example. When I call (or now videoconference) them, the investor and I usually get into some tangential conversations and I find other ways that they can help us. In other words, calling fosters a better relationship. Because I email updates frequently, constantly fostering the relationship, it creates a virtuous circle where I get more out of our relationship, and — importantly — they do too.
Now, to be honest, I share the advice in this chapter frequently, but few follow it. The better entrepreneurial performers usually do. As for me, I’ve lived this since the beginning of data.world and before that at Bazaarvoice. As a result, I have a very active and engaged data.world Advisory Board and investor base. And all of our employees receive these as well. That way everyone is on the same page, having the same information about our progress and challenges.
As I expressed in Chapter 2, The Paralyzing Fear of Getting Started, it is often lonely at the top. But it’s a lot less so when you’ve surrounded yourself with competence, insight, and experience in the form of those you choose as investors and advisors. Today, at data.world our investors include Shasta Ventures, Tech Pioneers Fund, Jim Breyer, Arthur Patterson, Pat Ryan, Mike Maples Jr., and even four of our customers (Associated Press, Workday, Prologis, and Vopak). Our Advisory Board, meanwhile, includes DJ Patil, Adam Grant, Kelly Wright, Kirk Dando (my CEO coach), Bob Campbell (who wrote the Afterword for this book), and 60 other very prominent and amazing people.
Select your external team members wisely, and you’ll be in and have a wise company. This is the external team that may well make a huge difference between failure and success.
“No man is so foolish but he may sometimes give another good counsel, and no man so wise that he may not easily err if he takes no other counsel than his own. He that is taught only by himself has a fool for a master.”
— Hunter S. Thompson, Author and journalist