How to Help Startups

It’s been seven years since I started my first company.  My successes over that course have had a great deal to do with the generosity and wisdom of the startup community, particularly in Seattle – countless meetings, meetups, blog posts, backchannels, and a mind boggling number of cups of coffee.  Since the very beginning, I’ve been thinking about the question in the title – what’s the best way for me to pay it forward, and really help the startup community?

I’ve always known that the greatest way to help startups is by building a great startup.  Success breeds success, injecting talent and cash in to the ecosystem.  It rejuvenates the optimism and bank accounts of investors and startup employees alike.  It begets positive press, which begets optimism.  It demonstrates to people that success is possible, and shows them a way to achieve it.

But I wanted to help more.  For karmic reasons – to pay back the people who helped me – and for selfish reasons, in that I love helping companies succeed.  It’s just incredibly, deeply, personally rewarding.  So each week I average about five to ten meetings with startup founders or executives, and usually do one speaking engagement for a large group as well.  But how to make the most of that time?

Here are the principles I’ve found so far when trying to help startups.

Lots of People

Try to find opportunities to help as many companies as possible, at once.  Like mentoring for great organizations (I love Techstars and Founders’ Institute).  There’s an opportunity to help a lot of companies at once.  Further, you get to have a bunch of short conversations to get an idea of what they’re up to, and dive deep with a few companies that are a great fit.

Help Companies That Help Themselves

The greatest impact on the startup ecosystem is helping companies that have already demonstrated commitment and traction.  If someone’s working a day job and wants advice “about startups”, that conversation is less likely to result in a successful company. By comparison, in a conversation with someone who’s committed fulltime and trying to add a cofounder, or negotiating terms with an angel, or stuck on their B-round financing there’s a real opportunity to make a difference at a powerful inflection point.  The further down the funnel the startup is, the lower the chance that good advice will be rendered moot by one of the many random quirks that strike down entrepreneurs, sending them back to the clutches of Big Companies.

Time Management

Being short and blunt sucks.  It’s uncomfortable to skip small talk.  But when a startup needs help and time is constrained, talking about a founders’ kids or hobbies is time that either comes out of their help, or out of helping someone else.  For me, the former is better than the latter, and I schedule most startups for 30 minute meetings.  I personally hate the rushed agenda, but it’s usually enough time for me to be able to try to provide some help.

If You’re Not An Expert, Shut Up

I sat next to a guy on a panel who was pontificating to startup founders about qualities to look for in a cofounder.  The speaker was a former consultant who mostly invests in real estate and restaurants. WTF.  It’s easy to have an opinion, but if there’s no experience behind it, just explain that it’s not an area of expertise and move on to a new topic.  I’ve sometimes had to drive this home. “Why are you asking me how to marketing your social network when I’ve never done it before either?  Let’s focus on questions I’m actually qualified to answer for you.”


It’s hard to be direct with people you don’t know very well – at least, I find it so.  And being direct is just a thin grey line away from being an asshole.  But nobody wins if the conversation just goose-steps around, and 30 minutes isn’t enough time to be soft and circumspect.  These my three favorite phrases when time is short:

  • “How can I help?”  This is my favorite phrase.  If there’s a succinct answer, everyone benefits.
  • “Sorry, but I can’t.” At least one of the things a company asks for are probably not possible.  But if the requests are out on the table up front, everyone can focus on the “yes”es instead of the “no”s.
  • “Here’s my reaction to what you just said.”  Sharing a quick gut-take reaction is crucial to companies that are trying to polish their presentation – after the 25th pitch, details and nuance get ground down.  The pitch is an art form, and a tight feedback loop is crucial to improvement.

Help People Help Others

This is the last principle, and a new one.  It may not be popular.  We’ll see.

As a part of my effort to make a difference in the broadest way possible, I’ve signed a contract with O’Reilly to publish a book about startups.  I’m ridiculously excited about this because it’s the ultimate application of the “Lots of people” principle. Part of this book is going to be illustrating problems with stories from real startups.  And that’s hard, because most entrepreneurs are pretty tight lipped about what they’re up to.

So from here on out, I’m going to be asking one important thing from companies that want to meet with me to get advice: let me use the contents of our conversations and emails to help other startups by writing about them.  If there’s something that must remain confidential – for example, a trade secret, or the name of a sensitive party in a negotiation – that’s fine.  But I think the startup community suffers from a little too much secrecy, so I’m going to prioritize helping companies that are willing to ‘pay it forward’ over companies that are not.

So that’s my new thing.  Continue to help people, and ask that they allow me to use their situation for my book, so together we can help even more people.

What Do You Think?

I don’t normally solicit comments, but I’d really like to hear reactions to this in the comments below.  Am I asking too much, that startups be willing to share with the world?  Is there a principle missing? Are there better ways to help?


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