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The article, "Startup School: Lessons Learned & Learning Lessons", originally appeared on Medium, and has been republished below with permission.

This fall, I will be mentoring a group of startups for Y-Combinator’s Startup School. It would take forever to capture everything, so instead I wanted to share a small bit of what I have seen it takes to “start up a startup” (h/t and Guy Kawasaki).

Here’s an excerpt from the welcome letter I sent my group.

*  *  *

Every founder has their own unique point of view on what matters most, when it matters, and how to address those things. If you’ll indulge me, I’ll quickly share my point of view on those matters so you can 1) see how I see things 2) understand how I can best help.

Where Are You Now?

Startups evolve over time, making it hard to compare one to the next. The biggest mistake we make, however, is assuming we’re further along than we really are. There’s “shipped” and then there’s Shipped.

I tend to group startups into a few specific categories:

  • Ideation — this is the phase where you’re recruiting your team, where you’re starting to align on shared experiences and frustrations, and sketching out problems you’d like to solve and how to solve them
  • Exploration — this is the phase where you’ve loosely decided on a problem that you believe is worth solving, understand who has the problem or are the person with the problem, and have notions of ways to solve the problem
  • Execution — this is the phase where you understand the problem with depth and breadth and, more importantly, the solution that creates the most value in the shortest timeframe
  • Expansion — this is the phase where your solution has proven valuable and the most important thing is adding as many customers as possible

What Matters Most

It can seem like everything matters, but the truth is that there are just a few that matter.

  • People — there are 2 key kinds of people that matter most — your team and your customers. It’s easy to believe that it’s all about the customers, but you require a team to service those customers in a successful, scalable way.
  • Priorities — what we do and the order we do things is the next most important thing in a startup — you can’t do everything so you must choose wisely and constantly adjust. Others often refer to this as execution.
  • Product — don’t fall in love with what you’re making, fall in love with the problem you’re solving. Iterate solutions, not features and ship them frequently. Your product isn’t just the core you ship, but how you talk about it, sell it, and support it.
  • Profits — at some point, revenue will be important to your business (it may even be possible up front) and it needs to be paid its due consideration. Understanding how to build a sustainable business requires mastering the first 3 Ps.

When It Matters

Much like everything doesn’t matter, most things don’t matter until much later than we think. If experience has taught me anything, it’s that the stage of a startup overwhelmingly dictates what’s most important.

  • Ideation + People — when we’re ideating we benefit from diverse opinions and domain expertise. The more smart, experienced individuals we can collaborate and interrogate the better.
  • Exploration + Priorities — smart people generate lots of ideas, almost too many. Without learning how to prioritize these motivations and concepts, we’ll drown in options.
  • Execution + Product — as loose notions become firm features, our company’s value and narrative become equally important. With a moving product, the rest of the company essentials (sales, support, success) all start to come into focus.
  • Expansion + Profits — we often mistake our first customers for our final customers, but usually they’re far apart. Growing a business forces us to think about what’s coming next, who’s there, and where we want to be

Of course, everything will repeat and likely accelerate and decelerate at unpredictable rates and intervals, so buckle up!

How To Address What Matters

There are countless ways to build towards both success and failure — and neither is really knowable until you crash upon it. That said, there are some tried and true things I know most be paid attention to.

  • Communication — be open, be clear, be repetitive. It’s super easy to assume that everyone is on the same page and most likely, we’re not.
  • Process — they’re important and should be as light as possible for as long as possible. The best processes emerge from your work itself.
  • Validation — if you’re afraid to hear the answer, you likely have a problem. Validate as much as you can to the confidence level you’re mildly uncomfortable with.
  • Negotiation — learning how to handle challenges and reach unity while achieving your goals is going to be super critical. The world is full of No’s, take them on head first.
  • Prioritization — Figure out the inputs you need to make decisions as quickly as possible. This process need not be exhaustive, nor final… but it must exist. See a theme forming here :)

is a serial entrepreneur and product strategist. A reformed designer and developer, he writes on his experiences as a founder, strategist, and father on the regular. Connect with him on LinkedIn, follow on Facebook, or say hi on Twitter. He is also a Mentor for the East Bay Founder Institute.

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