How to Ask for Startup Advice – Part 1

Summary:  Asking for startup advice is a skill, one that I haven’t always been very good at.  If you ask for lots of advice constantly, know your top 1-2 business challenges, ask 1-2 specific questions each time, and ignore a lot of what you hear you’ll be on the right track.  Listen to me discuss this post on Soundcloud.

I did some online searching before writing this blog post to see what others are saying about this topic. I was surprised that I couldn’t find a lot, and much of what I found I disagreed with.

I’m now helping  several entrepreneurs a week through my startup help office hours. While I’m happy to meet and help any entrepreneur (more on why in Part 2 of this post), some people are just better at asking for advice than others so they get more out of our time.  Here’s how you can get the most out of startup advice.

Ask for Advice Constantly from A Lot of People

My first piece of advice is to ask for it constantly from lots of people.  Asking for startup advice is a skill, it takes practice.  I’m still really struggling with it.

I didn’t do this for most of my career and now really regret it. I guess it just comes with being an engineer – I’ve always viewed the hard work of solving my own problems as part of the journey.  While this may be true for technical skills, I think this mentality really works against us as entrepreneurs.  I’ve tried to get better at asking for advice and now try to do it constantly for a few reasons.

First – unlike many technical challenges – there often isn’t a solution.  Any major business problem requires a lot of input, a lot of judgement, and often requires multiple steps to solve.  Can’t find Customers to Develop?  Maybe you’re in the wrong market.  Maybe a new tactic will help build better relationships.   Maybe you’re not asking for introductions efficiently.  Maybe the problem is a combination of all three, but regardless I guarantee you’re not going to figure it out by asking any one person for advice.  Or looking on Google or Quora.  These situations are way too complicated.

Second, startup advice is to entrepreneurs what golf is to sales guys – a way to build relationships. I love going to startup meetups and events but nothing makes a personal connection like helping each other.  By asking me advice you’re giving me an opportunity to meet you and see how you think. By asking you for advice I can demonstrate that I respect you.

Know Your Top 1-2 Business Challenges

We’ve all got an unending number of startup challenges. I try to do my best to know my top 1-2 every day. That way when I meet someone and have just a few minutes I can ask for advice.

Perhaps you’ve got too many challenges and can’t pick the top 1-2. Since you can’t execute on more than 1-2, you actually do know your #1 challenge: identifying and prioritizing your risks.

Ask 1-2 Specific Questions and Plan for ~20 Minutes

I don’t think email works very well for startup advice.  Or Twitter.  Or anything other than two people talking to each other, so I try to meet people face-to-face or over Skype, ideally during my startup help office hours.

A 30-minute coffee/Skype meeting has about ~20 minutes of productive advice time. The remaining 10 mins is critical (and fun!) relationship building, what some people call “small talk”.  In 20 minutes we can only cover 1-2 issues in any meaningful depth. Remember that we can have another meeting later.

Be focused.  You’ll get a lot out of it and you’ll impress people.

Ignore a Lot of Advice

There is value in hearing people’s perspectives but you certainly don’t have to take anyone’s advice. If you’re asking a lot of people for advice you’ll go insane trying to take 80% of it.

Advice isn’t fact – it is opinion. I do my best to help, but sometimes I’m just plain wrong.

More in How to Ask for Startup Advice – Part 2

Follow these 4 points and you’ll get the most out of startup advice. You’ll also start to really enjoy it. In Part 2 of this post I’ll cover:

  • Why understanding the advisor’s goals is important.
  • Why living outside of Silicon Valley or another startup hub can be an asset.
  • Why you should skip the startup gurus.

Photo Credit:  dhammza


  1. Masha Kubyshina February 19, 2013 at 7:08 am #

    Kevin, this is a great post! Also, I really enjoyed our conversation with you during your office hours. Thank you once again.

    • kevindewalt February 19, 2013 at 7:33 am #

      Anytime Masha, the pleasure was all mine.

I read EVERY comment and want to hear from you