by • October 27, 2011 • Founders, Pitching & sellingComments (4)351

You can’t strategise your way past hard work

Some startup stuff is just hard. Ben Horowitz wrote a terrific post on the product side of this:

Our web server is five times slower. There is no silver bullet that’s going to fix that. No, we are going to have to use a lot of lead bullets.

If you haven’t nailed your core value proposition, you need to put your head down and work hard until you do.

Now let’s talk about customers

Any customer-facing interaction is a rife with silver-bullet-syndrome.

I’ve made every possible variant of this mistake:

Instead of hustling sales, I sought a clever marketing or channel strategy. Instead of finding industry advisors, I did market research on Google. Instead of talking to customers, I watched analytics or sent out a survey.

There are no silver bullets here. An explanation and happy ending are down below, but first watch Gary break it down in this video.

Some stuff is hard

I completely understand why this happens. Customer-facing stuff is hard! It’s initially so painful that you feel like you must be doing something wrong or missing a crucial puzzle piece.

I began my time in sales & customer development roles as a pathologically shy techie. For a long time, I was very bad at my job.

I never would have subjected myself to those first 2 years of agonising sales meetings if I had any alternative apart from firing my friends and squandering the investment we had been trusted with.

I messed up a lot of meetings. Investor meetings, sales meetings, advisor meetings. I’ve ruined so many good leads, I can’t even begin to count. And every one of those mistakes cut deep.

But honestly? That’s okay. There was no other way. Sometimes you just have to power through. What was our alternative?

It gets easier

Two things will improve over time.

First, you’ll get better. Sales and customer development meetings became a pleasure for me once I deeply understood the industry. I had talked to so many companies and experts that I could reliably deliver real insight. You can’t market-research your way to that sort of understanding, but every conversation you have (whether a success or failure) contributes to it.

Second, momentum builds. There’s no magic strategy for landing the first few customers. And annoyingly, lots of case studies mischaracterise luck and circumstance as silver bullets. That leads to a lot of frustration when you try to emulate a non-repeatable strategy. But if you can get up that first stretch, eventually the momentum starts to carry you a bit.

Ten percent

I was drinking a coffee and chatting with a homeless guy the other day while he took a rest from his pitching. I asked him about his success rate.


I asked if it mattered how he pitched it or if certain types of people were better prospects or if he had any strategy and he looked at me like I was an idiot.

It’s 10%. You want a dollar, you ask ten people. You want ten dollars, you ask a hundred people. 10%

Those first 9 people who tell you “no” aren’t an indicator that you need to break out the ideation board. Some things are just plain hard.

Sanity check it with your peers

One of the benefits of hanging out with a community of founders is that they can help you distinguish between situations where something is legitimately hard and situations where you’re just being stupid.

The last thing you want to do is repeatedly sprint into a wall for 6 months.

You don’t need that many people to provide this sort of sanity check. A group of 5 founders meeting for an hour every 2 weeks seems to do the trick.

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4 Responses to You can’t strategise your way past hard work

  1. archie_g says:

    Try the game Rejection Therapy: . When else would you ever pump your fist triumphantly when being rejected? :)

    • robfitz says:

      Haha, yeah, it’s a neat structure. I’ve always felt I get rejected enough professionally. I don’t necessarily need to bring it into my home life as well ;)

  2. Wade says:

    I’m working through a lot of this right now and it reminds me a lot of Steve Blanks Peter Pan syndrome he writes about here:

    Basically, a lot of us just don’t know what we don’t know when we’re first starting out. We’ve got to get our learn our space, become domain experts, and fail a ton.

    Unfortunately, there isn’t any shortcut in sales. If you find one let me know.

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