Category Archives: digital.forest

Stuff about digital.forest, a company I founded.

Adventures in Fundraising

My first “real” investor pitch for digital.forest was in the lobby of the Seattle Westin hotel in the fall of 1999. There were five of us all huddled around a small coffee table to the side of the hustle and bustle.

My gut was doing somersaults and I was having a severe case of stage fright. I wasn’t sure I was going to be able to make it through this.

It was me, my friend Peter, who I had recruited to be a VP in the company, Michael, our advisor and lead investor who turned into a board member, and two prospective angel investors.

Michael had set up the meeting and had coached and worked with us to develop the pitch deck, which was a PowerPoint presentation that we had printed and handed out.

Taking a deep breath, Peter and I flipped through the presentation, stumbling and groping for purchase, trying to find the way to close an investment. We were sidetracked several times by flipping paper to answer questions. My stomach dropped even further.

Angel 1 was ebullient, loud, engaged, and asked many tough questions. Angel 2 was quiet, subdued, and seemed very distracted, like he wanted to be somewhere else. He didn’t ask many questions.

Angel 1 seemed very interested, but when we did the ask, he declined, saying he wasn’t sure we had our shit straight.

Deflated, and thinking we just crashed and burned, I turned to Angel 2 and timidly asked him. He chucked the presentation onto the table and then said, “Yeah, I’m in for a unit.”

My gut performed another somersault, but in a good way.

How to Motivate Executives, Part 2

Some executive hires will push for a fancy title, usually a step grade above what they were before. If they care that much, you should consider that they may not be the right cultural fit for your company. But if you need their skills and they seem like a decent fit, give them just about any title they want because they’ll be happier, which will make them more invested in doing a good job.

But do bicker about it for a bit to appear like you care and that you’re weighing their qualifications.

Fundraising Tip #1

Only call for money when the market is having a generally up day.

Most angel investors who pay attention to the market will feel richer and be more likely to get that check in because they feel like they’re investing their profit instead of their capital.

Think how you might feel about loaning $50 to a friend if you found a $100 bill in the street. Same psychology.

How to Motivate Executives, Part 1

When the digital.forest offices were located in Bothell, we had a handful of covered parking stalls assigned to the company under the building but, as you can see, most of the parking was out in the lot.

As I recall, we had about six assigned stalls and roughly twenty people on staff at the time.

A new hire, a replacement Vice President of Sales, wandered into my office one morning not long after he started with us and sat down in front of my desk and then proceeded to ask me how he could park under the building.

The unasked question was, “How do I get an assigned parking spot under the building out of the rain?”

“Oh!” I enthusiastically replied, “That’s easy! Show up early, and park in a spot!”

He blinked a few times, then smiled before he sheepishly mumbled something I didn’t quite catch as he leveraged himself up from the chair and then went back to work.