How to Ask for Startup Advice – Part 2

In Part 1 I covered some basic guidelines for getting good startup advice.  These are a few additional tips.

Forget “Startup Gurus” – Ask Smart People for Advice

Nobody knows nothin.
Mark Andreesen, at a speech I heard him give in 2001.

Listen to a micropodcast about “startup gurus” on Soundcloud.

When I first started in entrepreneurship I tried to get meetings with the “go-to” guys in Washington, DC.  Two weeks of trying to get intros to Steve Case and I got nowhere.  In those 2 weeks I could have been asking others for equally good advice.

The startup entertainment industry promotes some entrepreneurs as “start-up gurus”. There is no such thing as a startup guru – the world is way, way too complex and changing too fast. 1

Some are really smart guys.  Some have been uber-successful.  Some are just good at self-promotion. It doesn’t matter.

Forget the gurus. You’ll be able to get advice from 10 smart people in the time it will take you to get their attention. Remember that novices often give better advice anyway because they don’t suffer from the curse of knowledge.

Outside of Silicon Valley?  Few Local Startup Advisers?

Use your unique geography as a way to connect with lots of people

Listen to a micropodcast about smaller startup markets on SoundCloud.

If you live outside of a startup hub (New York, Silicon Valley, etc.) there may not be many people in your hometime who want to help startups.  You’re going to have to meet people in other communities to get advice.  Fortunately, you can turn this liability into an asset.  I did it in Washington, DC 5 years ago – when it was definitely NOT a startup hub.  Today anyone can do it.

A few nights ago I got a startup help call scheduled with an entrepreneur from Pakistan. Unfortunately he had to cancel and I was a little bummed.  I hope he reschedules.  Why? I’ve never talked to an entrepreneur in Pakistan. I actually don’t even know anyone in Pakistan. What I do know is that sometime in my lifetime some entrepreneur from Pakistan is going to be 1000x more successful than me.

dave mc

Dave McClure

The world is getting smaller.  Talent is increasingly becoming the scarcest resource in the world. In 2012 Dave McClure must have racked up 10 million frequent-flyer miles (seriously, the guy is everywhere). Why? He doesn’t want 500 Startups.  He wants the best 500 Startups and he’s willing to come to your city to get them.

Regardless of how small your startup community is, become “a someone” in your startup community. Help organize meetups, blog about your market. Reach out to other meetups organizers worldwide.  Host a party for Dave McClure at your house when he comes into town.

You’ll then be in a great position to ask for advice from other entrepreneurs around the world. Trust me, people will want to talk to you because you are connected in your community. I’ve done all these things (even hosting Dave at my house).  It works.

Save Yourself Time & Potential Rejection – First Know Advisers Motivations

People give startup advice for different reasons. Occasionally people just want to feel important, but mostly they want to make difference. Just know their goals.  Some examples.

Gabriel Weinberg

Gabriel Weinberg has a great diagram on when to ask for startup advice. I don’t know Gabriel, but my guess – and it is a guess – is that his goal is impact, particularly on the Philly startup community as a mentor and investor.

By asking people to go through several steps before asking for advice he is trying to maximize the marginal impact of his time.  Based on his reputation, it seems to be working. This is a perfectly laudable goal. It just isn’t my goal.


I care about impacting you. You the person. I’m going to do my best to give you my undivided focused attention during the brief time we have together and help you as best as I can. I want you to leave the meeting feeling like I made a small but positive difference in your life.

I think you’ll get the best out of our time if you have 1-2 questions and know your major business challenges. But I’m happy to help you figure out how to spell “startup” if you ask me.

I block out time to meet startups because I want to meet you, because by asking me questions you help me write better blog posts. If you’ve got a question, no doubt someone else has it too. I hope you won’t waste hours searching Quora and Google for a question I can answer in 5 minutes.  I care enough that I’m deliberately making it easy for you to schedule time with me.

Maybe someday I’ll hire you. Or you’ll hire me. Or you’ll retweet one of my blog posts. Or you’ll buy one of my products or tell your rich Uncle Tony to invest in my company.

If you know why someone wants to give advice you’ll be in a better position to meet them on their terms.

Understand Investor Mindset – Then Ask Questions They Can Answer

Listen to a micropodcast about asking investors for advice on Soundcloud.

I’m not talking about people who have already invested in your startup. I’m talking about an investor you just met, particularly one who doesn’t come from an operational background.

I meet entrepreneurs recently who only seek advice from investors.  In my experience, investors are excellent at understanding startup challenges from the macro level but less effective at the micro level.  

When I worked in VC I was a terrible advisor to any company that wasn’t in our portfolio. I saw so many failures and deals that I felt like nothing would work. I was so bombarded by inbound pitches that I started every meeting trying to figure out why an idea wouldn’t work just to get through the day. I viewed everything through the lens of our investing objectives and thus spent all day long casting judgment – that was the job. People would ask me for advice but I just wasn’t in a good situation to provide what most people really need – focused encouragement.  Bootstrappers were “lifestyle companies”.

Investors tend to make quick judgments.  They may have limited experience at the very early concept stages and can forget how easy it is for us to take harsh feedback personally.  Obviously this is a huge generalization based on my limited experience.

What investors can do really well is tell you what is and isn’t working because they see so many companies. They’re the most likely to know what models have failed, what models are working.

Questions?  Just grab a slot during my startup help time and I’ll be glad to help you.

  1. Although some deserve our admiration because they’re making a truly unique contribution to the field – Eric Ries, Steve Blank, Brad Feld, for instance. They’re just smart enough to be humble and curious and not call themselves gurus.
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