This post is the first of a series on  “unexpected lessons” learned through my experience as co-founder and CEO of Snapvine, a venture-backed mobile social networking service founded in 2005 and acquired by WhitePages in June of 2008.

In the years just prior to starting Snapvine, I racked up 2 years of debt attending the MIT Sloan School of Management.  School was great, but the costs were hefty:  tuition, travel, the expense of selling a house and moving, the opportunity cost of going without salary for 2 years, the high cost of living in Boston and stress associated with my wife changing jobs twice to follow along.

Thus, 6 months after graduation when I was contemplating leaving my job, the risks felt enormous.  My inner voice was asking:

• What if we go 12 months without pay only to fail to prove out the concept?
• What if we DO prove out the concept but fail to raise money?
• What if we DO raise money, but fail to deliver on the vision?
• What if we DO raise money AND deliver on the vision, but the business model doesn’t pan out?*
• What if we fail and my wife doesn’t let me do startups anymore?**
• What if my MBA classmates get 3 years into a great career while I spend 3 years for ZERO and then I have to crawl back to the corporate world begging for a job, while they are laughing at me?***
  

Chewing on these types of questions was totally unproductive and made me feel shitty.   I’ve come to realize that doing startups is mostly an irrational choice. Just effing do it.

photo credit: divemasterking2000

After I quit my job, incredible people jumped into my world to help.  Before the company even had a name, people like Hadi Partovi, Thomas Reardon, Kirsten Morbeck, Rob Williams, Rich Miner, Jeremiah Robison, Curtis Vredenburg and many others helped shape the product roadmap, recruit early employees, craft a pitch deck and introduce key investors.

The unexpected lesson:  about 4 to 5 months after quitting my job I was already ROI positive in terms of networking, learning and satisfaction.

In just a few months I felt completely confident that if the startup went splat on someone’s windshield, I’d be able to find a more interesting and higher paying job that I had before.  Also, compared to an MBA, doing a startup felt like an amazing deal:  On one hand, an MBA (tuition alone) might run about $85,000 whereas the startup has cost me only $5,000.  The salary was the same ($0) but the learning and networking with the startup was much, much greater than with the MBA.

In retrospect, jumping into the startup led to some immediate and unexpected benefits that, at least for me, far outweighed the forgone salary of my previous job and positioned me better for my future.  Quitting turned out to be a zero risk move.

* Interestingly, this is probably the closest to what actually happened, and things turned out fine
** Even though we’d already had the discussion “if I do 55 startups in a row and they all fail, is that okay?”  Answer: “yes”
*** I’m pretty sure they wouldn’t laugh at me if I ever failed, but I’m hopeful they’d hire me

Related posts:

1. Unexpected Startup Lesson #2: Channel your Inner VC to Understand Startup Valuations
2. Unexpected Startup Lesson #3: Why You Can’t Read a VC
3. Add logs, pour fuel (VC money), light match (beta release day)

I’m heading up to Vancouver tomorrow for the inaugural board meeting of a startup I recently invested in. It will be the entrepreneur’s first ever board meeting.   It made me think about what I’ve learned about conducting good board meetings.

Donuts by VeganWarrior (Flickr)

1) Bring an informed point of view

Startups can be thought of as a never -ending set of decisions and risks.  It’s a big part of the CEO’s job to anticipate the most important ones, think through a set of options and (importantly) prepare a point of view on the matter.  When faced with a dilemma, don’t just say to the board, “okay, we have this issue and need to make a choice.  What should we do?”

Instead, come prepared with what you think are the possible alternatives and your recommended choice — with supporting data to back it up.   Leverage your board and your advisors to come up with the alternates in the days before the meeting, and of course be open to further investigation or even changing course based on the discussion.

2) Be upfront, open and honest

This may be your first startup, but it won’t be your last.   Listen when your stomach starts telling you something is not going well in the business, or there’s something you need help on.  Be up front about it.  There’s no point to hiding anything or glossing over negatives.

Lay everything out and rally people to help solve.  Taking a “we’re on the same team” type approach goes a long way towards building rapport and support.  It’s helpful to have the people who hold the purse strings on your side, especially when the shit hits the fan.

3) Establish a template and stick to it

Much of the structure (product metrics, finances, hiring updates and so forth) doesn’t change – only the contents do.  The same metrics you use to manage the business should be the same metrics you’ll use for the board presentation.  If you’re spending lots of time just pulling the basic board deck data points and formatting things, it’s a sign that your metrics aren’t automated enough or you’re not looking at the right metrics day to day.

4)  Send the materials out in advance

When your board members have a couple of days in advance to review the basics, then you’ll have more time to spend on the most value-added discussion during the meeting.  If you find yourself awake at 2am the night before the board meeting, try blocking some time out well in advance of the next board meeting to finish your prep early.

5)  Serve food to lift spirits

Studies show that eating certain foods can improve one’s mood.  Enough said.

I probably should have posted this all a few days ago.  I’m really craving donuts right now!

Related posts:

1. Crucial first hire: the "do-it-all office admin"
2. Unexpected Startup Lesson #2: Channel your Inner VC to Understand Startup Valuations
3. 3 Things I’ve Learned To Recruit Great Hackers