Do Fewer Things, Better

Posted by Dharmesh Shah on November 24, 2015 in strategy 21 Comments

I'm going to tell you a secret.  I have a very simple, 4-word strategic plan (devised it a few years ago).

Here it is...


Do fewer things, better.

This has made my life -- and my work, dramatically better.

Here's how I execute on my strategic plan:

1. Decide on what matters the most.

2. Say no to everything else.

3. When something falls in the gray area, re-read #2.

Of course, that's easier to say than do. I fail at it all the time -- but I'm getting better.  Here are some tips learned from years of practice:

1. When making your list, start with a low-level of abstraction.  Resist the temptation to make your list really "high-level".  As an extreme example, one of the things on your priority list shouldn't be "Be successful".  That's so broad, that you'd be able to rationalize almost every activity under the sun.  Try to be specific enough that the number of things that "fit" is a manageable number.  If you find yourself taking on too much (which you probably do), refine your filters and move to a lower-level of abstraction.  I've written an article on this that you might find useful:  "The Power of Focus and The Peril of Myopia".   

2. Forgive yourself for having to say "no" to things not on your "fewer things" list.  Years ago, I wrote a blog post asking public forgiveness , you can see it here at http://MustSayNo.com.  Of all the articles I've ever written, that one has had the most positive impact on my life. 

3. Remember that every time you say "no" to something you might have said "yes" to, it frees up time to focus on the things that matter.  And the more time you spend on the things that matter, the better you get at them.  Let me give you an example:  Let's say you say "no" to some project/request/idea that would have "only" taken a few hours a month, because it didn't make the "few things that matter" list.  And, let's say that one of the things that matter to you is being able to better communicate your message to the world -- via public speaking.  Those few hours you "saved" can be spent on getting your message out. More speaking gigs, more people influenced.  But wait!  That's not all!  Not only are you able to do some more public speaking, because you're going to spend more time on it, you're going to get better at it.  And, because you get better at it, you're going to get more frequent speaking invites.  With larger audiences.  And have more influence once you're on stage.  You're building leverage by getting better and better at the thing that matters.  And, it's amazing how much better you will get, once you decide on only a few things to get better at.

By the way, the reverse of this is true to:  Everytime you say "yes" to something, you're saying "no" to something else.  Often, you're saying "no" to something more important.

4. Fight the FOMO (Fear Of Missing Out) emotion.  It's a killer. We all have it to varying degrees.  This fear that if we don't say "yes" to something, we're going to miss out on some big opportunity, small joy or new connection.  Yes, sometimes you will miss out, but that's OK.  Life goes on.  On average, you will be better off skipping some things, instead of trying to do too much.  

More people fail from a gluttony of good activities than from being starved of them. 

5. Be super-careful with recurring commitments.   If you are going to occasionally say "yes" to things that are not on your "things that matter most" list, be super-careful that they're not a recurring commitment.  A one-time commitment of 4 hours is much less dangerous than a monthly hourly committment.  The way I think about this:  When I say "yes" to a recurring committment, I'm effectively saying "yes' multiple times (for as long as I think I'm going to be in that committment).  Which brings me to the next point...

6. As painful as it is, prune your prior committments. If you are like me (and apologies if you are), you've said yes to a few things that you now sort of regret.  Get yourself out of those.  Be respectful, be, understanding and be fair -- but be disciplined and true to yourself.  And just because you committed to something last year with no real "expiration date" doesn't mean you have to keep doing it forever.  Things change.  On a related note:  For things that don't have an expiration date, remember that it's going to be just as painful to prune later as it is now -- why not give yourself the gift of some time back sooner?

7. Try to solve for outcome, not activity.  Figure out what you want to happen (whether it be a commercial interest or a philanthropic one), and figure out how to best create impact.  Usually, optimal outcomes are not achieved by saying "yes" to a bunch of "good" activities (however well-intentioned).

On the point of philanthropy, you might be wondering: "What about doing good, and giving back?"  

Warning: My opinion here may be controversial for some and feel beknighted and self-serving to others. Sorry.  

First off, if you have the ability to give back, you should do so.  No doubt.  But the question is, how do you optimimize for outcome?  

Let me explain with a personal example.  I'm an entrepreneur.  Have been for most of my professional career.  I LOVE STARTUPS. THEY BRING ME GREAT JOY. I'm one of the co-founders of HubSpot (NYSE:HUBS).  I'm also a big fan of Boston and want to see the Boston startup ecosystem grow and thrive.

But a few years ago, I decided to dramatically limit the time I spend directly helping entrepreneurs and the Boston ecosystem.

Why would I do this?  Isn't that selfish?  Yes, I guess it is.

I'm a big, big believer in leverage and scale.  I like to spend my calories in ways that deliver the greatest impact and the best outcomes.  I'm actually quite geeked out on that idea. 

The reason I made this decision was that I felt the best way for me to help the startup ecosystem -- was to use my time to help make HubSpot a super-successful company.  The by-product of that success will be much greater than what I'd get if I were just directly trying to help a handful of startups.  

 So far, HubSpot has had some modest success.  We are a publicly traded now and have 1,000+ people working at the company.  We have many that have "graduated" HubSpot and gone off to start their own companies or join other teams.  We've also made a bunch of people money (several of whom are channeling some of that back into to the ecosystem by way of angel investing). We've improved Boston's "brand" as being a place where big tech companies can still be built (which helps pull in more capital, talent and interest).  All in, I'd say we're a net positive.

But, fact remains that instead of being a mentor/advisor/mensch -- I've sort of been a schmuck when it comes to where I spend my time.  My money is a different matter -- I've made 60+ angel investments.  But, I've been fiercely protecting of my time and I've said "no" to just about everything. And remember, I LOVE STARTUPS.  I love helping them.  I love the thrill, joy and fulfillment.  But, I said "no" anyways.  And, I may be rationalizing here -- but I think I've likely done more for the ecosystem than if I had simply gone to more events, tried to pick a handful of startups to be an advisor/mentor for, etc.  

This section got much longer than I planned for it to be.  I have a whole other article in draft-mode titled "The Surgeon In The Soup Kitchen".  I'll give you the abridged message of that post:

Don't favor what feels the most good.  Favor what does the most good.  

Thankfully, blogging is a high-leverage activity.  And, since I'm using HubSpot to write/promote/track this article, it helps HubSpot too.  So, I can rationalize this into my "fewer things" list.

Cheers, and best wishes with your "fewer things". 



Read More

5 Mistakes Every Startup Founder SHOULD Make

Posted by Dharmesh Shah on June 2, 2014 in guest strategy 11 Comments

“It’s fine to celebrate success but it is more important to heed the lessons of failure” - Bill Gates

Much digital ink has been spilled trying to caution startup entrepreneurs against making mistakes. Type "mistakes entrepreneurs make" into Google and you'll find thousands of articles, sternly forewarning against the most prevalent pitfalls and errors that stand between you and your startup's success.

But wait a second. How many times have you heard "We learn from our mistakes"? As an entrepreneur and investor, I've definitely made some doosies - and if my experience is any indication, not only do we learn from our mistakes, but we learn much more from our mistakes then from our successes.wrong-decision

Then why try so desperately to avoid them? Call me contrarian, but I'd argue that well-positioned mistakes can be quite worthwhile, and should even be encouraged.

So here's an initial list of mistakes that you SHOULD make as a startup founder. Mistakes that are bound to happen anyway. Mistakes you will learn so much from that you'd best make them as early in your entrepreneurial journey as possible. I've also included some recommendations about what to do after you make each mistake.

1. Get Screwed

It's inevitable. Someone - your partner, co-founder, employee, investor, or any other character in your unfolding plot - will mess you over. Someone will break your trust, violate a verbal or even written agreement, cut your compensation, or try to steal your equity or destroy your whole company (or all of the above, if you're me). Someone will do something stupid to scuttle your grand plan.

Accept the inevitable, steady yourself now for the oncoming blow, and just hope it doesn't hurt too much or cause too much damage. A startup is usually an odd mix of people (idea people, tech people, investors and others) thrown together by fate and circumstance in pursuit of a distant, moving target. As clearly as you think you see that target and the path and steps toward it, somebody else will see that path differently or may have a different set of scruples or incentives. That will create friction, and depending on the power balance between everyone involved, can result in someone - maybe you - getting screwed.

Post-Mistake Action: You're thinking, "Why is getting screwed my 'mistake?' I didn't do anything wrong." Look in the mirror. Upon reflection, you'll likely find that what enabled your misfortune was something you did or didn't do. The screwer-screwee relationship requires at least two people, and there are two sides to every story. Even if you clearly weren't "at fault" - you encountered a terrible, crooked person who did you in - you still need to ask yourself how you allowed yourself to do business with that person. Was the person's action foreseeable? Did you do your due diligence on your partner/employee/investor? What did you do or not do that exposed you? As George W. Bush famously said: "Fool me once, shame on you. Fool me twice… shame on…. we can't get fooled again!" (cue The Who). Having been burned once, you'll be much more careful in the future about compromising your principles or allowing yourself to do business with people who may take advantage of you later on.

2. Seek Revenge

This is an adjunct to the above mistake. Once bitten, your natural impulse may be to bite back. You've lost something - tangible, emotional, some future upside or all of the above - and you want to deny the perpetrator those same things or at least the satisfaction of having caused you that loss. You've been wronged, and your reflexive urge is to right the wrong by wronging back.

Go ahead, try it once. I predict that not only won't you be successful, but most likely nothing will happen at all, or worse, it will bounce back at you. If you got screwed, that probably indicates you don't have the leverage, power or ability to exact meaningful revenge anyway. You'll just feel immature, cheap and dirty and the lingering recollection of that bad feeling probably will be enough to prevent you from playing the revenge card again.

Post-Mistake Action: Look forward, not back. The objective of the startup game is to win, and two losses don't equal a win. Rather than dwell on the past, "Revenge it Forward." Your best revenge is going to be your own success. Use what happened to you as an additional driving force, a motivator to prove to yourself, the person who messed you over, and the world, that not only do you deserve better, but that you can achieve better.

3. Tell People Your Venture is in "Stealth Mode"

It's natural to want to keep your cards close to your vest. Perhaps you're afraid someone will steal your idea, or you lack confidence that you've developed it well enough to convincingly describe it to others. The tech industry has even provided you the gift of a cool-sounding cover: "Stealth Mode," which makes you sound more like a covert spy shrouded in secrecy than an unsure rookie plagued by insecurity.

Saying you're in "Stealth Mode" is almost certainly a mistake, for many reasons. First of all it can easily be interpreted as either pompousness or insecurity, which is bad for your credibility. You're also signaling that you don't trust that person, creating a negative feeling that will likely persist even after you're able to elaborate later on. Most importantly, though, you are missing out on potentially invaluable opportunities to use your own network to shape, develop and advance your product or venture. Every person you know, meet or speak with can be a key to your venture's ultimate success.

Post-Mistake Action: Switch to "Get Out There" Mode. You never know who may be a potential customer or investor for your awesome new product, or more likely, who may know someone who could be a customer or investor. There are ways to plant the seeds of curiosity, to scout out a territory, to indicate what market you are targeting, without giving away the store. As Steve Blank advocates, it's critical for the founder to "get out of the building" (physically or virtually) as early as possible, and to start getting feedback from live people very early on and keep iterating based on feedback. By keeping everything a closely-guarded state secret, you are squandering opportunities to connect with people who might ultimately help you achieve Product/Market Fit, partner with you or invest in your venture. Come up with a "teaser" line that tells people enough about what you're working on and who you're targeting to pique their interest, generate confirmation of market problems and pain points, and generate future interest or relevant contacts.

When I founded EverMinder I was happy to discuss it with just about anyone long before it was fully developed. I got great feedback that led me to our first three angel investors, all via referral, all before we launched.

4. Believe that "If You Build It They Will Come"

The problem with the movie "Field of Dreams" is that it planted the phrase "If you build it, they will come" firmly into the common parlance and specifically, into the heads of countless, impressionable startup founders. The popularity of the phrase (and its confirmation in the movie, when Costner builds "it" and "they" magically come) leads some founders to believe, and predict to investors, that they, too, need only to build their amazing new thingy, and the users will come running until the rest looks like a hockey stick.

The problem is that as opposed to ghostly baseball players in Hollywood movies, I can assure you that if you just build "it", "they" will almost certainly not come. In startup theory the "coming" of "they" is called "Market Pull" which almost never happens by itself, even among early adopters. Market Pull needs to follow an intense and iterative period of product design, customer development, Product/Market Fit and hands-on "Technology Push" into the target market, which only if successful begets the glorious Market Pull. You'll have to work hard to make the market notice and care, and probably personally engage your early users individually, and that's fine. If you've hit Product/Market Fit squarely, "they" will eventually come, but only after you've very actively recruited and engaged your early adopters.

Post-Mistake Action: Stop believing stupid movies. If you've quoted "if you build it they will come" then you don't understand enough about Technology Push and Market Pull, customer development, and developing your Minimum Desirable Product. Instead of watching movies, read. A lot. You need to learn about these concepts by immersing yourself in the writings of Steve Blank, Sean Ellis, Andrew Chen, this very blog, and the other great proponents of effective product and customer development, and get up to speed fast.

(Ok, if you're still looking to be inspired by a movie, then watch The Pursuit of Happyness. Listening to voices in a cornfield will get you nowhere. Perseverance in the face of adversity, hustle, understanding and caring passionately about your product and customers, and relentlessly pursuing your goals will give you a shot to win.)

5. "My Favorite Mistake"

This mistake is probably my favorite because, like the Sheryl Crow song, it's complicated. It's the mistake I continue to commit most frequently.

My favorite founder mistake is not appropriately balancing confidence and humility. There's a yin/yang relationship between the two and as you pilot your rocketship forward, you will occasionally find that you’ve leaned too hard to one side or the other.

As a startup founder you need to have a healthy dose of self-confidence. Ok, maybe an unhealthy dose. An overdose. You need to passionately believe that your solution is The Next Big Thing. But overconfidence can be extremely dangerous, for many reasons. It can be misinterpreted by others as arrogance, which can cause damaging interpersonal consequences. If overconfidence morphs into false confidence, It can cloud your vision or your analysis. A great founder must have just as healthy a dose of humility, an understanding of his or her relatively small place in the world. But being too humble can hold you and your venture back….

A great Talmudic sage once wrote "Every person should have two pockets, each with a reminder note that he should refer to in the appropriate circumstance. In one pocket should be a note with the phrase: 'The world was created just for me.' In the other pocket should be a note that reads: 'I am like the duct of the earth.' "

(Five bucks says that's the first time Sheryl Crow and a Talmudic sage were mentioned together.)

Post-Mistake Action: Unfortunately I don't have a clear "post-mistake" recipe for this one. Managing your self-confidence and humility is a push-and-pull balance exercise that you have to keep performing, every day. It's up to you to gauge each circumstances and determine which reminder note applies.

Now that I'm an early-stage investor, I meet with entrepreneurs eager to convince me that they (and their ventures) are awesome. That's great. But I don't want entrepreneurs to sugar-coat their backgrounds. I expect and want them to tell me about their mistakes and failures. I want to hear what they've learned (and also that they've made those mistakes already on someone else's nickel, not mine). A good entrepreneur wants to talk about their mistakes as well as their successes, and a good investor wants to hear about those mistake and lessons without penalizing the pitch.

It's cliché, but nobody's perfect. You're not perfect. Mistakes will happen, and you will make your share. Expect them, embrace them, and analyze them, as those mistakes and the lessons learned will become important, lasting building blocks in your personal development and the development of your company.

So get out there, make some mistakes, learn from them…. And win.

This was a guest post by Ben Wiener (@BeninJLM). Ben is a startup founder and is Managing Partner of Jumpspeed Ventures, a Jerusalem-based micro-fund that invests in early-stage startups.

Read More