The Startup Cheat-Sheet

So, you want to do a startup.

You have an awesome idea, you and your cofounders have the tech and design chops to start building it, and you have the guts to leave behind your day jobs to make it happen. Kudos to your entrepreneurial spirit!

The one thing I’ve learned about starting startups is that they force you to always be learning. You might be a super-smart engineer, ace designer, or distinguished MBA grad, but no matter how fluent you are in your craft, in startup land you will find yourself in uncharted territory daily.

You’ll have to raise money, navigate legal contracts, dig into inbound and outbound marketing, track the right metrics, get into an accelerator, run a crowdfunding campaign.

In other words, you’ll constantly be doing things that you’ve never done before.

That’s why I’m writing this series. As a founder, I’ve had to learn things on the fly that I knew nothing about before (and know “just enough” about now). Along the way, I’ve leaned heavily on mentors and blog posts and Google searches to fill in my knowledge gaps.

But it would have saved days of my time if I’d had some entrepreneurial cliff notes to consult now and again. Hence my name for this series: The Startup Cheat-Sheet.

AKA How to Hack Your Way through Silicon Valley

But I don’t want to oversell these humble back-of-the-napkin tips. I’m not going to tell you how to come up with a great startup idea, or how to build a great product, or how to achieve a $100 million exit.

You’re the only person who can figure those things out. And my credentials to be dispensing advice are almost non-existent — I haven’t been to business school or had a blockbuster exit — but like you, I’m a tech person doing a startup. I’m simply here as your peer to talk shop, compare notes, and hopefully save you a bit of time when it comes to the more mundane aspects of starting and running a business.

How To Start a Startup

Here’s what I’m hoping to cover in this series:

  1. How to Incorporate Your Company
  2. How to Close Your First Investor
  3. How to Create a Winning Pitch Deck
  4. How to Hire Employees & Advisors
  5. How to Get Into an Accelerator
  6. How to Run a Crowdfunding Campaign
  7. How to Track the Right Metrics
  8. How to do Cohort Analysis
  9. How to do Inbound Marketing
  10. How to do Outbound Marketing

What other topics would you like addressed? Leave a comment below. If it’s something I know anything about, I’ll consider writing a post.

That’s me pitching at our 500 Startups “demo day”.

How I Started Up

Now that I’ve introduced the series, I suppose I should introduce myself. I began running my first business as a college freshman in Kentucky circa 2004 — an unassuming web agency that I started with my roommate, Andy Fowler.

We made websites for local and regional businesses, set them up with our homemade content management system, and charged them monthly for CMS access (SaaS!) and hosting. We cut our teeth as designers and developers, learned the basics of running a small business, and paid our bills through college.

After graduating I took a job in London working as a UX designer for an enterprise content management company. A year later, I had two startup opportunities that I couldn’t pass up, and ended up becoming the lead designer for a customer relationship management startup called Nutshell, while also cofounding an enterprise search startup in London named Twigkit.

I split my time between the two startups for a year and a half (not easy!), but after helping launch version 1.0 of Nutshell, I stepped away to devote my focus to Twigkit. There we created a platform of user interface components for rapidly building search-based applications and licensed our software to large organizations such as Thomson-Reuters, Qualcomm, BASF, Vodafone, The Financial Times, ITV, Rolls-Royce, and others.

During my five-year tenure there we bootstrapped the company (i.e. funded the business through organic sales rather than raising outside capital), and it was eventually acquired.

I then moved back to the U.S. (first to Seattle, then to San Francisco) in early 2015 to start, a coffee marketplace that enables individuals and offices to discover and subscribe to coffees from artisanal roasters.

I teamed up with coffee pro Emily McIntyre, and over the past two years we’ve run a Kickstarter campaign, raised angel investment, hired employees and advisors, launched our platform, learned a lot about running and growing a two-sided marketplace, went through the 500 Startups accelerator program, and much more.

Most of my cliff notes will be based on these last couple of years.