Ep2: VC by Day, Entrepreneur by Night & Weekend — Zero to Point One

I feel like an entire month has gone by since my first post last week. I put in a full week of work at Emergence including flying to Seattle for a diligence trip while continuing to make great progress on Silicon Heroes (T-Minus 10 days to the crowdfunding launch). Of course, I got so little sleep that I came down with a nasty sore throat and fever Sunday. Guess the days of being invincible are behind me.

Last week’s post was inspired by my struggles to execute and the lessons learned from that struggle. This week is more about lessons learned from executing on strengths. So here are the top 5 lessons learned from last week:

Lesson #1: Skip what is easy and focus on what is impactful.

For the past few weeks, I had been creating a list of to do’s in Trello and then ticking them off. I always seemed to get through the majority of the items but a couple of really tough ones would always be there at the end and get punted to the next week. I would always talk myself out of doing the hardest tasks — I would tell myself, “oh that’ll be easier when X is done”. Well, when I really looked at the tasks I wasn’t finishing, they were definitely the hardest tasks but also the ones that had the most leverage for impact.

Most of these difficult tasks required reaching out to someone important — an influencer, a journalist or someone that could potentially help. In all of these cases, I didn’t know the person so that is what made the task hard. That and the very real personal rejection I would feel when they ignored my emails.

So last week I just decided to start leveraging my relationships to reach the people that can really move the needle for Silicon Heroes. Yes, it was a lot of work and most of those emails, calls and meetings did not amount to anything. But, the few success cases (thank goodness I had a couple!) will move the needle much more than taking the easy actions of pushing things out into social media or trying to figure out other hacks for marketing.

Lesson #2: Don’t rely on email, get out and talk to people.

Inside sales teams fall into this trap too. Email is easy. Picking up the phone or meeting face to face is hard. But you know what? When I explain Silicon Heroes to someone in person, they almost always express an interest to help. I think it comes down to two reasons. One, the story becomes interactive and I can focus the conversation on what matters to the other person. Email is one-way communication and the message might be great but not relevant for the receiver. Two, people are busy and emails are easy to delete. It’s hard to ignore a person in a conversation.

The corollary here is that you have to balance time and impact.

Lesson #3: Emotional decisions suck. Make them, move on and don’t look back.

I really struggled with the Kickstarter vs. Indiegogo decision. It sucked a lot of mental cycles and really bogged me down for a couple of days. I have a CEO in my portfolio who has been struggling with a really tough strategic decision for his business and I saw the toll that decision was taking on him. He ultimately made his decision this week and I could see the weight lift right off his shoulders. His courage to make a decision where there is no clear right answer and move forward with conviction helped me in my own much smaller dilemma. These types of emotional decisions can lead to a lot of second guessing and flip flopping. But you just have to make them and move on.

Lesson #4: Time pressure will eventually force you to narrow your focus so stop expanding the scope of possibilities.

I’m a dreamer. I’m at my best when I get carried away with the possibilities of what could be. I think that’s why I like being a VC. However, that character trait is not great when it comes down to crunch time execution. For the past month, I felt like my to do list was growing faster with new ideas than I was able to knock tasks out. A few days ago I just said no more. I triaged my Trello board and discarded everything but the essentials. It felt great and now I know I’m working on what is necessary.

Lesson #5: Be willing to change your plan on a daily basis.

Every day I get some new piece of information that causes me to change course. Maybe it is a person I just met who can help in a way I had not planned. Maybe it is an external vendor that isn’t cooperating. Or maybe it is a marketing strategy that is not performing. You just have to have the mental agility to process new information and tack quickly. I used to be bothered by the sunk costs — hey, I put a lot of energy into X. And now I’m just going to abandon it for Y. Actually, yes, when new information comes up, burn the boats and start moving in the new direction. Of course, it’s easy for me to do this because I’m an army of one so there is I don’t have to convince anyone else.

So there you have it folks. Hope you all enjoyed another week of a VC trying to moonlight as an entrepreneur. Launch day is 10 days away so this next week is going to be a flurry of activity. Thank goodness for cold meds.

Next: Ep3: Unpredictable Revenue

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