When I started David Shen Ventures, LLC, I originally thought I could advise only or advise and invest. The latter would be a form of watching my investment by helping the startup in a formal fashion. I also thought that in certain cases, I might only advise but not invest.
So far, I have not invested in all of the companies I am involved with. In most of these cases, I just missed the opportunity to invest because I could not get in on the series A, or that opportunity had already passed. But there is the case where I could invest but choose not to.
Originally, I had just started up with entrepreneurs and signed up as advisor whenever the opportunity arose. I had not given much thought to points at which they would get to raise funds, but only to make my involvement formal by completing the paperwork. But now I am wondering about whether I should continue this method of operating or change it.
Why would I not invest but still advise?
One big one now is that I am coming to the end of my allocation of funds for this purpose in my budget. I had originally set aside some money out of my own pocket for angel investing as a means of diversifying my overall portfolio while making a new career out of it. I was planning to stop when I reached the end of that block of money and take stock of my operations and investments to see how I was doing. I near that limit now.
Another reason is that I have, at the time of this posting, 8 companies I am working with. Being an advisor allows me to increase the number of companies I am involved with, but potentially lower my exposure to investment in too many companies that I could effectively watch over as advisor AND be investor in. My model is to not be a passive investor at this point, but be active only (I may change this strategy later). But I do have A.D.D. and love to be involved in more companies than less, so I know I can sign up as advisor in more companies than I could be investor in.
But sometimes, I work with the entrepreneur a bit and just come to a point where I think I can help the company but my funds are better deployed elsewhere. It’s a hard choice to make as you think you can help anyone, but sometimes you can and sometimes you can’t help them in a way to make the company take off on a super positive trajectory.
That doesn’t mean that the company has no chance (in my view) but just means that I can’t help them as much as I’d like to be helping them, whereas for other companies I am adding a tremendous amount of value and seem to be making a huge difference in their trajectories.
So in deploying my own funds, I have to make that hard choice in deploying money in the companies with the maximum trajectories and me helping them. And not everyone is on the same slope of trajectory. It’s a really hard to choice to make.
Recently, there was an unanticipated effect. Because I have decided not to invest, other investors have begun to ask why I have not invested. This is naive in my view, as they just assume I would invest in everything I’m involved in, which is not true.
Seeing as how I may not be able to fully explain my operational model to everyone, this unanticipated effect has me re-thinking about whether I should advise a pre-money company but not invest. I do not want to inadvertently reduce a company’s chances for investment by putting doubt in other investors’ minds about a company’s prospects.
No particular solution comes to mind as of yet, but it is something I am working on more fully now. I may slightly change my operating model with entrepreneurs to not officially sign up as advisor until much later and until a lot of the business and product plan as been set. At this point, I can really evaluate whether I will feel comfortable investing and advising or just not continue my involvement. If I sign up as advisor too soon, then I may get myself in a situation where I am advising but when the first funding round comes, I decide not to invest.