In starting out a self-funded company, I didn’t just get a board by virtue of taking on an investor, but I still found that I really wanted a way to get feedback and advice from more experienced people I know and trust.

To that end, I started asking friends and colleagues if they’d be willing to receive a weekly progress report from me, and occasionally field a few questions. Having worked with a number of generous and savvy people, I quickly got about two dozen people on my list.

Starting from my first week “on the job”, I sent an email to this group roughly¹ once a week detailing how things were going.  This email has three broad sections:

• A narrative description of the big issue(s) I dealt with that week. This might be describing some engineering issue, a new feature, or how some recent customer interviews went.  If applicable, it contained pictures and/or videos of recent progress.
• A bullet points list in three sections: what I accomplished, what I’m still working on, and what’s next
• An evaluation of my own emotional state (optimistic? disheartened? frustrated? elated?) and a brief outline of why and how I got that way.

Including the center section was especially helpful as it forced me to get very clear about past/present/future each week.  It also gave me an impetus to really complete things so I can include them in the accomplishments section, and thereby gives me a sense of accountability.

When I sent these emails out, I almost always got back a few responses which range from actual solutions to issues I was having, to simple words of encouragement (which were still much appreciated!).

¹ except when nothing much had happened, and I was just working through the same plan as the previous week