You don't get shit you don't ask for

When we were raising money for FlightCaster in Fall 2009, we met with dozens of investors, both VCs and Angels.  Most of them turned us down.  The investors that did put money into FlightCaster provided us a ton of value, both in terms of their capital and all the support/guidance/networking.  

And what about all those investors that had turned us down?  They actually ended up providing a lot of value as well, and that's what this post is about.  I had noticed a funny trend from each one that had turned us down.  They all closed with a variant of this statement:

"If there's ever anything I can ever do to help, please let me know."

At first, it sounded like a standard pleasantry, in the same vein of "I wish you the best of luck." But then, I started thinking about why it was that every investor was saying it.  I realized that there are two forces at work here:

The first is that many investors are genuinely nice guys that do root for entrepreneurs.  Many made it as entrepreneurs and remember the pain and the hustle.  If (and this is an important if) an action is not at odds with their fiduciary duty to their limited partners, most investors will do what they can to support you.  

The second force at work is pure incentives.  Investors know that relationships matter.  An investor that passed on a company may want back in at a later point if that company takes off.  Or she may want to fund a future company of that entrepreneur.  Doing favors without an investment is a cash-free way to prove to the entrepreneur that they have real value to provide in addition to their capital.  

So, back to our story.  I decided to take them up on their offer.  All of them.  I literally contacted every investor that turned us down and asked for a concrete favor.

We had just launched the FlightCaster product and were working hard to meet people in the industry.  My co-founder Evan Konwiser was not yet recognized as the thought leader of the travel industry that he is today.  We had a big conference coming up where every leader of the travel industry would be in attendance.  And we knew no one.

With a few hours on LinkedIn, I was able to see which investors knew someone that knew someone we wanted to meet.  I sent a personalized version of this email to all those investors that offered to help:


Thanks for offering to further support us as we build FlightCaster.

Right now, we're preparing for the PhoCusRight conference next week, the travel industry's largest get together.  We're trying to make some connections with people at the conference.  Can you help us connect with leaders in the Business Travel divisions of Expedia or Orbitz?  Or any other introduction that you feel would help us?

Thanks for the help!



And you know what happened?  A huge number of those investors responded within 48 hours, and most of them were able to help in some way.  And it was the most impressive investors that responded the quickest.  Here's the response I received from Ron Conway the next day (using his classic all caps):


I KNOW THE CEO OF EXPEDIA…send us an email template to send to him



So, yes, we got introduced to the CEO of Expedia because Ron Conway, who had previously passed on investing in us, was willing to help.  Booyah!!  Why did he do it? Because Ron Conway is also one of those guys that is fundamentally rooting for the entrepreneur.  

The other reason he did it?  Because we asked.  You don't get shit you don't ask for.



A few tips on asking for help:


Ask for what you want

This is a common Paul Graham statement to YC companies.  Figure out exactly what you need and just ask for it.  Don't play games, don't posture, don't hint.  Just ask for what you want.


Make your request very concrete

We didn't ask for general advice.  We did our homework and made very specific requests.  It's much easier for people to respond to concrete requests.  Even if they can't provide for that direct request, the specificity of the request helps them find an alternative way to help.


Don't use and abuse

I only wanted to ask these incredibly busy investors for help once or maybe twice.  Obtaining industry introductions was one of the most important necessities of our startup. I made sure to ask for something that they could provide with minimal effort and risk.


Pay it forward

We're all part of the same innovation community.  This whole entrepreneurship thing is hard for everyone, but fortunately, everyone has something to offer.  Don't procrastinate on giving back.


Say thank you

Investors love knowing the outcome.  For both personal and professional reasons, they're interested in long term relationships.  Do your part by keeping them up to date with your successes.  I like to email everyone that helped me immediately prior to something showing up on Techcrunch.  It helps me communicate to them that I appreciate everything they did to be a part of our success.


Give it a shot.  The worst that can happen is that they say no.  And even that's not so bad--investors love knowing that you hustle.  So hustle.




Thank you to all the outstanding individuals that didn't invest in FlightCaster but still went out of their way to support us:


Stewart Alsop and Gilman Louie of Alsap Louie

Jon Callaghan of True Ventures

Ron Conway, David Lee, Kevin Carter, and Topher Conway of SV Angel

Brad Feld and Shawn Broderick of TechStars

Jeff Clavier of Softtech VC

Steve Anderson of Baseline

Micheal Dearing of Harrison Metal

Mike Maples of Floodgate

Jonathan Ebinger of Blue Run Ventures

Angus Davis

Pooj Preena

George Pierce of Venture Catalyst

Sam Landman and Michael Yang of Comcast Ventures

Peter Ziebelman of Palo Alto Ventures 

David Shen

Sharam Fouladgar-Mercer of Shasta Ventures

and many more...




Find discussion of this post on Hacker News 

I'm Jason Freedman.  I co-founded FlightCaster.  
You should follow me on Twitter: @JasonFreedman.
You can send me a Linkedin request or become my bff on Facebook





26 responses

Having worked with several startups (and with one going through the funding process as we speak), I can relate to your thoughts. Sometimes the closing remarks do seem a little gratuitous, but for the most part I think angels and VCs do have a vested interest in you, your team and your idea. Otherwise, they wouldn't be in business!

I think your "pay it forward" point is really key. There have been times that I have passed on introductions to other startups to VCs even though I have no direct involvement with them. Some have generated some interest, others not. But the VCs that I've dealt with seem to be genuinely appreciative of the "heads up". You never know when that one snowflake in the blizzard may be a superstar.


In our culture they say: "A baby that doesn't cry, doesn't get any milk".


I can only ask then if you wouldn't mind checking out a conversation I had with Jason Fried -
Hey - great article, very informative. Please forgive this small correction, but when referring to a person in your text, the pronoun is 'who' (or 'whom', if an object), rather than 'that'.
Very nice.I believe that if your idea is good ,you will find some investor sooner or later.If someone is not investing in you,it does not mean that he is treating you as a failure.May be he is not that skilled in your area.
So true, "a closed mouth doesn't get fed"! I think you really hit home on the asking for specifics part. Many people ask for help but leave it vague ans say things like anything you could do would be great. People (esp. busy investors) don't have time for that. They are looking for specifics. Be precise and to the point and you are more likely to get a response.
Also known as, "Shy don't get shit" and "The squeaky wheel gets the grease". But you're right about the manner you do it in cause an annoyingly squeaky wheel can get the whole car donated.

I needed the reminder... reminders.

Having retired from the mind reading business I sometimes forget that others do not have this power either.

Thanks again.

Dear Mr. Freedman,

Right now I'm preparing for lunch, which I'm hoping will be either a Dominoes or Pizza Hut Meat Lover's pie. Could you contribute financially to this effort? I do accept PayPal.

Thank you!

John Reeves

Brilliant, simple, and so true.
The key bit that is important is "be concrete in what you ask for" - and make it easy. "here is a massive powerpoint deck, can you pass it on?" is not concrete and easy... "I wanted to contact X because she is the leader in Y and we have something that could really benefit her. Could you connect us?" starts to be much easier to act on.
Jason, thanks for sharing these experiences. Great reminder that most people want to help and pay it forward.
It's the whole "if you want money, ask for advice; if you want advice, ask for money" played out here. Nicely done.
Good stuff. Sounds familiar. "You do not have, because you do not ask."
Amazing post! we are going on July 5th to Silicon Valley looking for raising capital for our StartUp. We need introductions! If you have any advice would be great!! i will tell about you in the book! :)
here my email> dponce(at)
This is great Jason, thanks. I really believe this too and glad you gave us some concrete examples from your experience.
This is a great read and very motivating. We are in the infancy stage of a start-up and are looking to raise capital. I never thought to continue to network with people that deny your capital requests. That is really good advice. After all, if I were in their shoes I would like to help out other entrepreneurs, even if I couldn't give them money. Thanks again.
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