Don’t Get Sick Of Telling Your Story

The Boulder TechStars program is in week three and the intensity level is high. The TechStars office is across the hall from ours at Foundry Group and it’s wild to see the level of activity ramp up during the three months that TechStars Boulder is in session.

I’m trying a new thing this program and doing a weekly CEO-only meeting. I’ve been trying to figure out a new way to engage with each program other than mentoring a team or two, and have been looking for a high leverage activity that I could do remotely for all of the other programs. My current experiment is an hour a week with all of the CEOs in a completely confidential meeting, but a peer meeting so each of them gets to talk about what they are struggling with to help solve each other’s problems as well as learn from each other.

We’ve done two of these meetings in Boulder and I love it so far. I’ll run this experiment for the whole program, learn from it, and iterate. If it works, I’ll scale it across all the programs.

Yesterday I also finished up my first set of 1:1 meetings with all of the teams. In my 1:1 meetings, I try to keep them very short – 15 minutes – and focus on what is “top of mind“. I learn more from this and can help more precisely than if I spent 30 minutes getting a generic pitch, which will likely change dramatically anyway through the course of TechStars. So each of these top of mind drills is “up to 5 minutes telling me about your company” and “10 minutes talking about whatever is top of mind.”

By the third week, I notice what I call “pitch fatigue” setting in. I think every entrepreneur should have several short pitches that they can give anytime, in any context, on demand.

  • 15 seconds: Three sentences – very tight “get me interested in you” overview.
  • 60 seconds: What do you you, who do you do it to, why do I care?
  • 5 minutes: Lead with the 60 seconds, then go deeper.
  • 15 minutes: Full high level pitch
  • 30 minutes: Extended presentation that has more details

Bt week three, the teams are still fighting through getting the 15 second and 60 second pitch nailed. That’s fine, but there’s emotional exhaustion in even trying for some of them. The founders have said some set of words so many times that they are tired. The emotion of what they are doing is out of the pitch. Their enthusiasm is muted – not for the business, but for describing it.

Recently I was on the receiving end of a description from an entrepreneur, who has a great idea that I love, that had the emotional impact a TSA inspection at the airport. He was going through the motions with almost zero emotional content. At the end of it, I said one sentence – “Don’t get sick of telling your story.” I then went deeper on what I meant.

He responded by email later that day:

Thanks for articulating what was going on in my head. I think I was getting burnt out from telling the same story to so many mentors. I need to stay focused and stick with the story that worked well the first 40 meetings. I also need to be careful that the lack of “freshness” doesn’t affect how passionate and energetic I come across. Timing for this realization couldn’t be better given our upcoming fundraising trip.

I’ve done an enormous amount of pitching and fundraising over the years. When we raised our first Foundry Group fund in 2007, I did 90 meetings in three months before we got our first investor commitment. By meeting 87, after hearing no a lot (we got about 30 no’s out of the first 90 meetings before we got a yes) I was definitely had pitch fatigue. But every time I told it, I brought the same level of intensity, emotion, optimism, and belief that I did the first time I told it. Today, six years later, when I describe what we are doing and why we are doing it, and why you should care, I’m just as focused on getting the message across as I ever have been. And I never get tired of telling our story.

  • katzgrau

    This sound lame, but on the flip side, telling your story to *customers* with literally no emotion tends to portray you as stable, mature, trustworthy, if you’re dealing with the same kind of customer as me (been around 30+ years, mostly 9-5ers, owner isn’t involved in the day to day).

    I know that sounds ridiculous, but I’ve actually had a lot of success selling my service to bigger organizations by being dry and unexciting. And despite being so early stage that even I wouldn’t do business with me, they take me pretty seriously — at least more seriously than when I had injected my real enthusiasm for the company.

    • Catson

      @katzgrau:disqus you are confusing the puppy enthusiasm of a young founder (or worse fake enthusiasm of a bad salesman) with assured/mature enthusiasm of knowing how to walk the talk

      • katzgrau

        Well, I wouldn’t say it’s “confusion.” I’m saying that older, non-founder buyers are more receptive to someone who sounds like he knows what he’s doing, and has been doing it so long the enthusiasm has been beat out of him. I’m drawing that based on my own experience in b2b sales and growing my company.

        I don’t make the meeting boring, I’m just very matter-of-fact for these types. I portray: Go with me, and you won’t have any issues. I’ve seen it all.

    • My guess is that we are defining “emotion” differently. You are likely substantive, clear, and direct. I doubt you come across as bored and detached. If that’s the case, I’d bet we are saying the same thing.

  • Paraic Hegarty

    I think that Brad’s point, and that of @katzgrau:disqus are actually the same. You need to sync on an emotional level with your audience. Mentors, angels, vc’s etc. want to be enthusiastic about your business and want to see that same enthusiasm in you. Quite often a corporate audience has no enthusiasm left 😉 and dislikes seeing it in you!

  • screendoor

    This reminds me a little of the Dick Costolo speech, that got a lot of press a few weeks ago, about how his comedy improv experience helps him to be a better CEO. Pitching is partly performance, and that’s not a bad thing. Part of CEOing is bringing energy to the endeavor every day, including the days when the game has beaten you down some. How do stage actors manage to do what they do every single night? A little bit of that same ability to turn it on when the lights come up is a good thing. And that’s not inauthentic. It’s showing the passion that you have but that might not be on the surface that day.

  • Rule #1 of marketing.

    When you think that everyone knows, you are always wrong.

    In fact, when you start to think everyone has heard it, you are just getting started.

  • rnschmidt

    Do you have a good example of each of those pitches you’re recommending we know cold?

    • There are some on

  • Catson

    As I was reading the “sick telling your story” line, a visual popped up in my head: think of how musicians must feel having to perform the same song over and over and over and remain genuine in their empathy. Unless you are merely a crowd-pleaser, you can always go back to the reason/purpose/belief that made you write it in the first place.

  • I’d also add that for the short pitches, it’s incredibly important to say the same thing over, and over and over again. It’s easy to get seduced by nuances and different variants, but that dilutes the message. A mentor once told me “As CEO, you’ve literally got to say the same shit over, and over, and over again – don’t get tempted to switch it up – that’ll just hurt your traction in the marketplace.” And of course, your job is to BRING IT every single time.

    And only 30 nos? That’s pretty good compared to the 126 I received. 😉 You should blog more about the fundraising process with LPs. I don’t think VCs talk about those dynamics enough.

    • Maybe I’ll do some more posts on VC fundraising, especially around our first fund. I realize I haven’t written much on that.

  • Albert Hartman

    Enthusiasm – if you can’t impress yourself, it’s hard to impress someone else. Solution is to be constantly doing hard impressive things and aiming high.

  • Good advice. Broadway actors do the same show almost every day, sometimes for years on end, and have to do it with energy every time. Yul Brynner did *The King and I* over 4000 times in his life. If they can do it, so can you.

  • The artist’s voice

    Great focus. Your story in the words that feel right to you always comes across as genuine. And I say a story, a pitch is less you and harder for the listener to engage with. Tell your story, always interesting.

  • If investors know what it is to get pitch fatigue, then why care about the level of enthusiasm? Why not let the idea, team and progress speak for itself?

    I come from advertising. I was a creative for 10 years, rising to creative director at one of the world’s top agencies. I know what it means to put emotion in a message, nor do I question its power. But my favorite work through the years has been my most understated. When I found an insight so powerful that it didn’t need a joke or jingle, and it could be told simply, without fanfare.

    • I don’t think “emotion” and “understated” are in conflict with each other. I’m a very level presenter – I’m not effusive or overly promotional. I have little fanfare in my life or in much of my work. I endeavor to be deeply substantive. But I’m engaged, present, and in the moment.

      I don’t expect people to conform to how I do it, but rather what is natural to them. But when someone is presenting and is “bored” or “fatigued” it’s pretty obvious to me.

  • another option: get them to pitch each others’ biz, and hear it from someone else.

    or, have them pitch their competitor’s biz. that is always interesting to hear them attack their own pitch.

    lastly, have them improv a completely diff business — we play a game called half-baked dot com where the participant has to pitch a random 2-word combination.

    just gotta keep it fresh 🙂


    • that last idea sounds amazingly fun.

    • Yup. Part of the practice fun is to learn how to present other stuff, and to hear how people present your stuff. I’ll often give my version of it back to the entrepreneur pitching me when I think I can dramatically improve what they are doing.

    • One of the problems I see is that, even with the 15 second pitch, you need multiple versions to match the styles/backgrounds of the investor types. Agree?

      • Yup! It’s worth having a few different short versions.

  • Fayez

    There is a related thing that happened to me in the current TechStars class. After week one, I was repeating the same pitch that worked well with high enthusiasm for the next few weeks. I have been doing improv regularly for over three years so there were a few exercises that I used to keep the energy levels high.

    Then one night while we were all out with the TechStars class, one of the fellow founders re-iterated my pitch word-for-word. Then about five or six of the other CEOs did the same thing and said that I had burned the pitch into their heads (it was receiver’s fatigue). However, instead of reinforcing my pitch, this ended up giving me instant fatigue the next time IF (and only if) i pitched in front of them. The next time I would pitch to a group in front of the other founders, it just felt weird and was never the same. I struggled for about a week but had to force myself to not get sick of the story and recover from it.

    • If you are good at improv, change it up a little when you give it to people who you see regularly. When we were pitching Foundry Group the first time, my partner Ryan and I did most of the presentations. We each had sections that we could go riff on. I’d occasionally head off on a space jam and Ryan would have to pull me back to earth.

  • “we got about 30 no’s out of the first 90 meetings before we got a yes)”

    I love when these little bits get shared. People often hear about the successes and see the positive but miss the long, rough road people take to get there. Google’s “first 17 VC’s said no” also comes to mind.

    Thanks for sharing Brad.

    • its really hard to hear no so often ..although I have a certain level of respect for people who come out and say no quickly.

  • very important to also practice and be genuinely enthusiastic even when outside of these pitching events. Our CEO at Influitive, Mark Organ, is genuinely enthusiastic throughout the day at the office. I think this serves to also keep people’s spirits up and I am certain that it helps him carry this demeanour when talking with investors, other entrepreneurs and potential prospects during live events.

  • Good insight, going through the process personally and also advising clients during their capital raises, I have seen this many times where they are so excited about their product/service/company thinking it is the best thing in history, only to get upset when they can’t raise money. It is more than just having a good idea for a product or service, you have to communicate it effectively to the right people, be realistic about bring it to market and scaling/commercialization, and get ready to be rejected many times.

  • I’ve been recently working with a few startups on their positioning & messaging, and it’s been interesting to see how small iterations can turn a dull statement into a more meaningful and exciting one. An outsider’s perspective always offers a fresh look, like when you say that you replay it to them in your own words.

    Couple of common lessons to share:

    1. Startups tend to have a “product mindset” that permeates their initial pitches. Rather, I tell them to switch early on to a “customer value” instead. Forget the product, said Peter Drucker. “It’s the customer who determines what a business is.” So, as a startup, don’t tell me what your product does or will do. Tell me how it will change the lives of the customer/user instead. What the customer considers value is never the product, but it’s what the product does for them, and that is something to be excited about. (I expand on this concept in my last blog

    2. The fewer the # of the words, the more precise and meaningful they should be. I would start with your 60-second step first, refine it, then go up and down the length stack, after. You need the 60 seconds to flush the value proposition completely. Choose your words carefully because words move people, but they can also cause indifference. Not all words have meanings just because the dictionary says so. In marketing, the meanings are in the people using the words.

    If you take the analogy of the sugar bowl as the container, and the sugar as the meaning, you fill the words (container) with meaning (sugar). If you add sugar to a leaky bowl, you won’t get anywhere. So, if you try to add meaning to a leaky word, that won’t work. Better to discard the leaky word and use another one. Brad, I suspect you can spot a leaky word right away and ask them to adjust it, because leaky words lower the credibility of the message. I have a full blog post on Positioning here:

  • The best way my partner and I have found to reduce pitch fatigue is to try and turn it into more a conversation than a pitch as early as possible. The most effective way to do that has been to get a question in there early on and base the rest of your pitch on their response. They’re engaged, you’re getting to improv a bit, and you’re catering the pitch to their use case. For example, we would ask “when was the last time you sold something online?” If it was recently, we talk about how they did it and the pros and cons of that method. If not, we find out why they don’t sell online often and what could change that.

  • Mike Post

    Thanks Brad. We can probably draw from comedians and musicians here too – how do they deal with fatigue from telling the same jokes or playing the same song, 100’s or even 1000’s of times?

    Ultimately I think we can find inspiration from making it “click” with the person you’re telling it to. When they go “ahh”, and you can see the connection in their eyes, that’s what drives me through the repetition of a pitch.

  • Yep. Absolutely hear you. I’ve run a boutique services business for 18 years here in nyc. You constantly meet new people, in the elevator to the office, at lunches, meetups, conferences, and social gatherings. So the opportunity to tell your story occurs over and over. The hardest part in operations is coming up with the analogy that clicks for people, so they get it. And yes, then telling it in a way that sounds like you love what you do.



  • What a unexampled because of share your viewpoint. Your content is packed with perceptive information and is well balanced with many professionals and cons. Kudos.

  • Good insight Brad. Thanks for sharing.

  • Justin Custer

    I needed to hear this. Thanks for the encouragement!

  • Kelly Peeler

    Really great post! If you’re tired of your pitch, everyone else will be too!