How Does One Advise So Many Companies at One Time?

Often I get asked by entrepreneurs to become advisor to their company and they take a look at my companies page and they wonder how I can handle so many companies at one time. Where does Dave find the time? Do the companies actually get enough support from me given that I am advising so many?
It’s actually not so hard. Here’s how:
1. I’ve found that advisor time commitment varies greatly from company to company. Some entrepreneurs use me as traditional advisors are used, which is to meet up once every month or quarter and give me an update and go through their plans and get my feedback. If all my companies were like this, I could definitely advise a ton more.
Others call or email me whenever they need something. I have many hours in the day and definitely can field calls or answer emails. Sometimes they ask for a site review or recommendations. This takes longer, but blocking out a few hours to do that isn’t a problem.
Some have wanted meetings weekly for a while. The weekly meetings never last though; entrepreneurs are pretty busy and they get going on something and they don’t have time to meet up any more. Or they learn enough or have firmed up plans enough to keep them going for a while and then they don’t need my constant interaction.
2. Perhaps the greatest time commitment is just thinking about each company daily. I often have at least one (or more) of my companies swirling in my brain and I try to record any ideas down asap. If I am in front of my Mac, I’ll open an email and just record the ideas in that; also, I have a small moleskin notebook that I carry around with me constantly to jot down ideas. Once I get all my ideas down, I check it over, do some rewrites, insert additional ideas that come to me on the fly, and then send it to the entrepreneur.
I like to get into the mode of a single company and its product and try to immerse myself in the product as a user, and the experience of needing/wanting that product. That enables me to really get into what I would want, and also what others could want in that product and where improvements can be made.
I multitask on this throughout each day, but sometimes I take some focused time and do this too.
Still, once a company receives these ideas and acts on them, they usually don’t need further time from me for a while.
3. Another task I do for my startups is connecting them with potential partners and sources of capital (although definitely I do not bill myself as a fund raiser). This requires me to network a lot with both old and newly met folks. Thus hour long coffees and lunches are the norm and these take time out of my week.
Also, I write a lot of emails introducing my companies to these partners as well. Thinking about which partner to send the company to and also sending the email does take up time, but not all that much.
4. My favorite thing to say about advisor time commitment is that almost all companies need the most time at the beginning of our advisor relationship. There is a big spike in time and thinking from my side and also in interactions and then somewhere between 2 and 6 months later, that time drops to near zero, with little peaks of time to do emails and check-ins.
The rationale behind this is that the company is supposed to learn everything I tell them. They finalize their plans with my input and feedback. They take this knowledge and are off and running building their product. They don’t need my interaction so much after this time because they have what they need from me.
This is one of my main goals: To transfer knowledge from my brain to theirs so that they don’t need me any more. If I do this successfully, they should be able to function for a long period of time without my input. Over time, my goal over the term of my advisorship is to help them find resources that would manage what I help them with day to day. This is finding and hiring a great full time design resource and great product management resource. It can also mean finding/hiring a great sales program person as well, to help them monetize their advertising programs.
I’ve been advising for about 2 years now, so many of the companies on my companies page are off and running without further need of my help.
4a. One thing that I have consistently observed is that if my time requirements spikes again after the initial peak, the company is in trouble…so I keep watch for this and hopefully help prevent this from happening.
5. OK OK I admit it. Even working like the above, I still can get pretty busy in the short term. In fact there was a time when I thought I was overextending myself due to the pace of advisorship signups. So now I am very aware of the pace of companies I advise and have slowed down dramatically based on my current support load.
6. Next, I tell people I shouldn’t be put on critical path for anything. It’s not what advisors do anyways.
A lot of people ask me to be advisor, but really want me to do the design of their site for them. If they want this, they should either outsource their design or find a designer to hire full time, and not try to turn an advisor into a fake full time person. I think this is especially true in product design; in order to do a great job, you have to be immersed 24/7 with the product and team. It’s hard to jump in and out or do it on the side.
If I’m not on critical path, that reduces time commitments from 24/7 to something much, much less and less frequent.
As advisor, I always tell people that I shouldn’t be expected to be put on critical path for anything because we’re both going to end up being disappointed and frustrated. Very bad!
7. Last, I love being involved in many things. It helps keep my interest level up and allows me to see the entire world of internet startups across the board, which is an advantage. I purposely try to get involved across a myriad of projects, across a range of areas.
It takes me out of being myopic into one thing, and allows me to help my startups by being broad in my thinking and not get too trapped into the details of one project. While this is important from an execution point of view, it doesn’t help when you’re helping to plan the strategies of these startups by not looking outward and seeing where the trends of the industry are going. Often I bring the broader view to my startups because they don’t have time to look at it themselves. They’re often too busy to do that. On the other hand, I want them to spend all their time executing and not get distracted.
I’ve really come to love advising startups. The connection with smart, energetic people working on cool new things is really great, and I enjoy helping broaden their vision and give them the help and knowledge they need to be successful.