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10 Things I've Learned in 2013

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Yesware CEO Matthew Bellows shares the ten most important lessons he's learned throughout his career in sales, startups, public companies, and day-to-day life in the modern workplace.

Yesware CEO Matthew Bellows shares the ten most important lessons he's learned throughout his career in sales, startups, public companies, and day-to-day life in the modern workplace.

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  • Introduction:I’m Matthew Bellows, the founder and CEO of Yesware. Yesware is helping hundreds of thousands of salespeople close more deals by adding sales-specific functionality to Gmail.I’ve been in sales for my whole career, both as a sales person and a sales manager. At my own companies, other people’s companies, and at a big publicly traded company. Although that didn’t last too long.On the plane ride out, I had a chance to think about what I’ve been working on recently, and what I’ve learned. I’d like to share with you 10 specific things here. I think they have direct applicability to sales and startups, although not in a “10 tips and tricks” blog post kind of way.
  • #1 - No One Knows What’s Going OnWe are stuck in a relative world – Our perceptions of reality are all completely colored by our past experience, by our current situation, by our surroundings, by everything. And our perceptions of reality change all the time! Depending on how we feel, what we’ve eaten, how much we’ve slept, etc. This image is an example. Which dark grey circle is bigger?The Buddhists say that the present moment has come together because of “Uncountable causes and conditions” The main conditions that cause the right grey circle to be smaller are the big circles around it. But there are lots of other causes and conditions that contribute. Stranger still, physicists have determined by a very complicated process of elimination, that approximately 5/6th of the matter in the universe, and 3/4th of the energy in the universe, is completely and 100% outside the realm of our perception.It’s got to be there in order for the universe to work the way it observably does. But we can’t perceive it! How can we know what’s going on if we can even perceive the vast majority of matter and energy in the universe???!Sure, after 20,000 years of dedicated study by the most intelligent species on the planet, we have a decent understanding of limited systems. Geology. Mathematics. Medicine. Starting companies. But if you question any expert in any of these fields, they can quickly come up with all kinds of things they don’t know about… unanswered questions. Even for simple things like – How to sell things well, how to build a small company, how to manage a baseball team… no one can give you the recipe. How to bake bread, yes. But things involving other people, any period of time longer than a day, anything complicated AT ALL… and we have no firm answer. The systems are just too complex.
  • With the present moment so incredibly rich, complex and mysterious, how can anyone know what’s going to happen in the future?  Lesson #2 is No One Knows What’s Going to HappenSo the situation sounds pretty bad. No one knows what’s really going on, and no one knows what’s going to happen.  The good news, is that we’re all in it together. Even your co-founders. Even your investors. Even the biggest baddest “Master of the Universe” VC has no real idea what’s going on or what’s going to happen. What can we do?Narrow the problem. Focus on what you can affect. Try to figure out your motivations and what makes you happy. That’s what the rest of this talk is about. But don’t forget about the water in which we swim, because it’s the thing that unites us all.  
  • Anyone know what this image is? Any economists in the room?Capitalism is about creating happinessSales is about creating value for both partiesSo the 3rd thing I’ve learned recently is “Start with Helping Someone Else”At Yesware, our Core Purpose, the way that we want to make our living for the next 100 years, is“To Help People Create Value with Every Exchange”The problems with capitalism are all about the options available to people, the environment that people work in, and how the created value gets distributed afterwards. That’s beyond the scope of this talk, but if anyone wants to discuss afterwards, I’m happy to.
  • The 4th thing I’ve learned is “Only Work with Great People”Life is short and uncertainMost of our waking life is spent at work. Spend that time with people who help you be a better person. Smarter, more thoughtful people. People endowed with interestingly different perspectives on life. If you don’t see those qualities in the people around you, first start by asking yourself if you really know those people. Have you given yourself a chance to understand their amazingness?If you are still hating the people you work with, help them help you by telling them about your perceptions. “When you do this, I feel…”When you get sick of that, look for a new job. Or create one yourself. But only work with great people.
  • My 5th lesson is “Work on a Big Problem”This is not for everyone. My first company was a small idea, and we sold it before it could get very big, because we weren’t up to growing a big company. But if you are up for it, working on something demonstrably, clearly, almost inarguably big, is much more fun than working on something small.
  • The 6th Thing I’ve learned recently is “Tell a Very Big Story”For our first two years, we struggled to frame the market for Yesware in a compelling way. I would point to the size of the CRM market, or the estimated number of salespeople in the world. Then I reframed our market story this way… $650 billion in sales commissions last year! 
  • Activity Counts For a Lot But…Sometimes we don’t know what to do. There are so many priorities, metrics, things to learn, activities to undertake, emails to check. How many inboxes of various kinds does everyone have? I recently counted 20 places where people I have some relationship with can leave me a message. You probably have more.  But it’s a lot harder to do nothing than to do something. Have you ever tried doing nothing? I don’t mean accomplishing nothing by watching the World Series (GO SOX!) or reading a blog. I mean actually do nothing. Be bored. Don’t feed your mind for just a bit. Here’s a fun thing to try… next time you are on a plane, unplug your earbuds and look out the window as the plane takes off. Just pay attention to the sound and the view and the feeling in your body. WHY IS THAT SO HARD TO DO?!? We need to have space in our experience to let insights arise. If we are always doing something, nothing simple and pure and beautiful can come up.
  • CEO Bootcamp experienceThe 8th thing I learned is “Everyone Feels Like an Imposter”Everyone harbors some fear that they will get found out as a fraud and will lose everything they’ve worked so hard for. Get Peer Support
  • I’m calling the 9th thing I’ve learned “Push Against the Honesty BarrierAnother way to say “Be Transparent” but it’s a little more difficult.Easy to be honest when the answer makes you look good. Push against the honesty barrier means when you are feeling the reluctance to be honest, push against that and really be honest. At charities they say “Give until it hurts a little” When you are working out they say “Go for the burn”. Same thing here. This is especially hard in sales when there’s a big short term gain right in front of you.But I’m sure it’s the right thing for me to do.  
  • The last item on the list is “I need to keep learning”One big thing I need to learn – how to scale a company from 40 to 400. What are things you need to learn to get where you want to be?That’s probably worth contemplating.
  • Transcript

    • 1. 10 Things I’ve Learned In the last three years more or less about sales, startups, work, and some other stuff
    • 2. 1.
    • 3. 2.
    • 4. 3.
    • 5. 4.
    • 6. 5.
    • 7. 6.
    • 8. 7.
    • 9. 8.
    • 10. 9.
    • 11. 10.
    • 12. In Summary 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. No One Knows What’s Going On No One Knows What’s Going to Happen Start with Helping Someone Else Only Work with Great People Work on a Big Problem Tell a Big Story Activity Counts For a Lot But… Everyone Feels Like an Imposter Push Against the Honesty Barrier We Need to Keep Learning
    • 13. Thanks very much. Contact me anytime: matthew@yesware.com @mbellows