How to describe what you're working on vs. who you are

This past week marked year 4 of the Creative Startups accelerator in Albuquerque. 

I went through the very first year of the program in 2014 with a local news startup, and although I'd already worked in and around startups (including a rapidly growing venture backed company in San Francisco), the experience provided a ton of knowledge about what it's like to build a business model in the early stages.

One thing that stuck with me: the toughest problem a founder faces in the early going mimics something we all face as individuals...what is your company? And who is it for? 

Whether you're growing / building / experimenting as a company or as an individual, that's a central question, more broadly phrased as: Who are you? And who are you for? 

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Doing the work is more important than celebrating entrepreneurship

There’s a great phrase that a friend of mine from Boulder uses often. 

She calls it “doing the work.”

It’s one of those things that seems obvious, but isn’t well understood by startups or founders. 

Sometimes that’s because of ego and/or too high a degree of self-awareness, and sometimes it’s simply because “doing the work” can be a slow, painful process without much worth celebrating. 

Doing the work isn’t about appearances, it’s about the value actually delivered or created. 

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Letting people fail

If you’re anywhere near the startup ecosystem, you’ll consistently hear the mantra of “fail fast.” 

Personally, I’d rather focus on the outcome, which is / should be about learning fast. But failure does teach us…and if we’re paying attention it gives us information that we can take further than the specific moment or situation. 

What gets less attention is the importance of letting other people fail, and that’s a shame because it’s a critical skill that isn’t well understood or talked about enough. 

Mentoring / advising, for example, has a lot of moments like these. Good mentors understand that you can’t control a situation, nor can you save someone from themselves. 

It’s useful to break that moment down, because where people need to fail and learn from that failure can be subtle. 

As a mentor it often looks something like this for me: 

  • Big problem or set of complexities, entrepreneur recognizes they exist and tells me about them
  • I clarify what’s happening to make sure I understand, then try to help them frame their own understanding
  • Here’s the important moment: Entrepreneur looks at me and says or implies outright “this sucks / I don’t know what to do / this is really hard and/or complex”
  • Even if you’re a good mentor (friend, boss, etc) it can be easy to skip right to “ok here’s how you fix it” or “why don’t you try X.” 
  • In reality, what needs to happen in that moment is that the entrepreneur (friend, family member, employee) has to recognize the structure around the problem they’re having, and you can’t make them do that. 

This can happen in a personal or professional context. The key is to understand that there is a choice involved.

If you are the person working through the problem or set of complexities, sometimes it means realizing you are in a bad piece of structure that you need to get out of. Sometimes it means recognizing that you’ve created some or a lot of that structure. Often it is both. 

If you are the person helping or advising, this process can be uncomfortable. The person may ask you directly to do something that you don’t feel will help them. Or you may care about the person and their growth, and want to make sure they don’t experience hardship or pain. 

Here are a few questions that help me avoid skipping steps, and prompt the entrepreneur to do their own work. 

  • “That sounds intense — how would you like to structure our time so I can be of help?” *suggests that they should ask for / define what help they need
  • “How are you thinking about approaching the problem?”
  • “What do you think needs to happen for you to work on it?”
  • “Is there a general beginning / middle / end that you see for solving this?”
  • “What information do you think you need to solve this problem and/or where do you go to get that?”

I’m speaking mostly here about entrepreneurship, but you can apply this approach to most situations, including co-workers, family, friends, significant other, etc. 

Letting someone fail can be one of the most graceful and compassionate things you do, and if you’ve created a supportive work environment, friendship, relationship, etc. they’ll learn fast and be on their way to greater things. 


The emotional state of an entrepreneur

Entrepreneurship is largely about belief.

Sometimes that belief is what keeps us going, but it can also lead to dangerous territory — like listening mostly to people who think the same things we do, or shelving deeper feelings for years only to find out later that they are subconsciously undermining our best work. 

A common mantra in the startup ecosystem (besides hustle, scale, and growth) is that you should test your assumptions. There are different approaches to testing, including the well known lean startup method that Eric Ries advocates for. It’s a concept that’s also well covered by Steve Blank, Seth Godin, and an array of designers, technologists and thinkers. 

With the exception of Seth, most of the time the language / framework for testing assumptions is focused on developing & designing a product or learning from customers, and rightfully so. As soon as an idea gets out of your head, into the real world, and beyond a small circle of people… that’s when challenging your assumptions becomes critical. 

But there’s another, slightly different way of thinking about it: you’re testing what you believe to be true, not only about your product but about yourself. 

Nowhere is this more evident than in how we avoid, deal with, process, or even embrace our emotional state in times of turmoil, whether it happens quickly or over a long period of time.

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On the importance of frameworks

I’ve never seen a business plan that looked like a business. 

I’m not sure exactly why this is, but it probably has something to do with the fact that in the early stage of any company there are a lot of variables, and things that seem to mean one thing can easily turn out to mean something else entirely. Sort of a particle / wave duality principle, but for startups.

(A high number of people who sign up for a product trial, for example, might not be a positive sign if none of them stick around once their two weeks is up — possibly indicating that your inbound growth levers need tweaking). 

For many entrepreneurs and startups, frameworks occupy a critical space — the one that arrives after “I have a bunch of ideas” but before “here’s the full plan to take over the world.”

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