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When talking to a founder or early employee in an early stage startup I always start by asking “What do you guys do?” After that, I follow up with “What do you personally do in the startup?” When they answer, I like to mentally categorize it in one of two buckets: selling or building. If the person provides a long answer without much clarity, I’ll make my question more specific and say, “Do you sell or build?”

One of the goals with this line of questioning is to get the person to focus on selling and/or  building. Too often, I hear that people focus on things like strategic direction, managing an advisory board, etc. Those are important occasional things, but shouldn’t be the day-to-day focus of a few person startup. Once product / market fit is achieved, more team members are brought on, and there’s room for specialization, it makes sense to branch out. Until then, almost all of the effort should be either selling or building.

What else? What are your thoughts on simplifying the seed stage startup experience as either selling or building?

There’s a Hype Cycle is a methodology invented by Gartner about technologies whereby expectations start out in grand fashion only to fall off sharply into the trough of disillusionment. Then, slowly, over time the visibility and impact grow creating tremendously productivity and value. Entrepreneurs follow a similar path on the personal level when building a new company.

Over the last week I’ve talked with two different entrepreneurs that were in the trough of disillusionment. Of course, they didn’t volunteer to me that they were in the trough of disillusionment. Instead, they said that they were down because they’d been pushing hard on their new startup for the past year and haven’t seen the results they expected. Worse, results on the revenue side were almost none existent. With the advent of the New Year, and the typical reflection time, more stress is self-inflicted around achieving success.

Here are a few thoughts on the trough of disillusionment:

• Startups always have highs and low lows, so attempt to keep perspective
• Business models like the Software-as-a-Service / cloud model are beautiful, but the time to build a customer acquisition machine is often excruciatingly long
• Everything takes twice as long and costs twice as much as expected, so plan accordingly
• Gut checks are critical throughout, and sometimes the right move is to keep moving forward and sometimes the right move is to give up

The next time things are going poorly, think about the trough of disillusionment and figure out where things stand. Much like Seth Godin’s The Dip, sometimes things get worse before they get better.

What else? What are some other thoughts on the trough of disillusionment for entrepreneurs?

Several years ago a friend of mine came back from an EO University and was raving about a session he attended where they built a one year person development plan. Naturally, I love these kind of things and asked him for all the details. The idea is straightforward, as expected, but incorporates numerical goals as well as specific habits. Most of the time people think of one year goals as “I want to make X dollars and lose Y pounds.” This methodology is useful because it incorporates those goals as well as more specific habits desired (e.g. I want a healthy marriage so one habit is having a date night once a week).

Here’s the plan template:

• Professional
  – Category, 2014 Achievements, Habits
  – e.g. My Startup, $1,000,000 in revenue, attend one entrepreneur event/month
  – e.g. My Income, $100,000, 50 cold calls/day
• Family
  – Category, 2014 Achievements, Habits
  – e.g. Spouse, Good marriage, Date night/week
  – e.g. Child, Healthy relationship, One adventure/bi-weekly
  – e.g. Vacations, Out of town, One week/quarter
• Community
  – Category, 2014 Achievements, Habits
  – e.g. Non-profit board, Donate time, Two hours/month
  – e.g. Donations, Give $1,000, One meeting/month
• Personal
  – Category, 2014 Achievements, Habits
  – e.g. Weight, 175 pounds, Run 10 miles/week
  – e.g. Learning, Reading, One book/month
  – e.g. Fun, Attend a sporting event, One event/quarter

So, dust off those recent New Year’s Resolutions and add habits to go along with the goals, as well as break things out into professional, family, community, and personal.

What else? What are your thoughts on a one year personal development plan?

If you like to run, it’s easy to keep track of your time when running a 5k or 10k, so you can continually strive to set a new personal best — it’s human nature to want to improve and get better. Of course, this applies to the entrepreneur world as well. After a big success, the goal is to surpass it with the next venture. But, what if the bar is set extremely high? How do you measure success?

Here are a few thoughts on the challenge of surpassing a previous success:

• Think about the journey more than the destination
• Success comes in many forms like creating jobs, being challenged, building relationships, achieving goals, etc
• Limits and guidelines should be set around personal capital invested, amount of risk desired, etc
• Legacies come in many different forms and doing one thing well repeatedly isn’t required

Surpassing a previous best is a real challenge that is rarely achieved in the entrepreneurial world. Regardless, as long as the game is fun, it should be played.

What else? What are some other thoughts on the challenge of surpassing a previous success?