I hope you fail.

Failure has a really bad rap... Why is this?

Actually it starts when we are quite little. Our parents start feeling pressure somewhere around the time we turn 12 months old and the “expectations” start kicking in… Are you walking yet, because your cousin and neighbors are? What about talking? Full sentences or just a few words? Do we actually feel those expectations and that disappointment in our parent’s eyes at these early ages? That’s how early it starts.

From there it only gets worse… Did you make the baseball team? Did you get an “A” on your test? Are you doing all the same after school activities your friends are (music, dance, sports, etc.)… By the time you are applying to college most people have been beaten into submission and don’t bother trying to go for the long-shot school, or the creative degree or choose the offbeat path… Even fewer have the intestinal fortitude to say I’m not going to college, I’m starting a company or sailing the globe or starting a non-profit that changes the world.

Our fear of failure almost insures your life is constrained… So sad!

Winning is very important in life… But failure might be more important.

So, trust me, forget everything you know about winning and start thinking a lot more about failing.

Failure is where you learn and grow It’s when you’ve tried something and it didn’t work and those new emotions become fuel. They push you forward and force you to re-think, re-examine and change. To win in startups, investing, relationships or life you have to take the kind of risks that ultimately expose you to failure and what you do with that failure makes all the difference.

When you start failing a bit, you can start winning big. So don’t be afraid to fail… embrace it as it means you are closer to big things.

Photo credit: chrisgriffith


The Startup Manifesto

Twenty years as an entrepreneur... many companies built, four sold... Lots of mistakes made and lessons learned. This is how I would boil it down to key lessons and things I try to live by...

Here is the text if you want to format it for yourself:
The Startup Manifesto

Risk is your friend. Great people make all the difference. Make sure you can always answer “WHY”. Get up early. Change the scenery, you can work anywhere. Hire people that challenge you, not just those that listen to you. Ask yourself tough questions. Don’t waste time. Spend time on ideas that matter and people who energize you. The 80/20 rule applies to startups as well. Focus. Work harder than your peers, but go to your kids’ play at 2pm on a Wednesday. Be honest and transparent. Don’t hire employees (employees punch clocks), instead find co-pilots who share in the risk and reward. Never stop learning. Cruise control is the worst place to be. Take more pictures. Choose the path less traveled. Track everything. Be scrappy. Remind yourself daily why you are/became an entrepreneur. Make the call. All investors aren’t created equally – so be very selective. Experiment, Experiment, Experiment…. If you get comfortable, change something!

For more on startups visit: maclackey.com

The WALL (or the dip, or the treadmill)

People have given lots of names and visuals as well as provide many analogies about life as an entrepreneur… They do this for good reason. It is difficult to be entrepreneurs so we like to set expectations through things potential entrepreneurs can relate to. Even seasoned entrepreneurs often need the visuals to remind them what they are dealing with. We all need to wrap our minds around something that provides us comfort.

So here’s my visual.

Being an entrepreneur is like “sprinting into the fog”.

I’ve been a “formal” entrepreneur my entire working life and every company I’ve started, every investment I’ve made, company I’ve advised, etc. all share these characteristics…

Let me break them down quickly:

Entrepreneurs are driven. They have a deep desire to do something (make money, fix a problem, change a behavior and so on), and when you have a desire to really do something, significant, you MOVE. You don’t wait for others. You don’t wait for the money to come in or the contract to be finalized. You just go… Doing so means that you are moving at a pace that is sometimes uncomfortable for you, but certainly for others. Entrepreneurs sprint.

Even when you have a clear vision, when you are convicted and know where you are headed, the world around you is foggy… It is often foggy because it’s new. There is no data to prove your thesis or expert to consult or book to read… You are charting new paths and that means things around the edges are hazy and you have to make decisions before the answer is obvious. You have to operate with “some” data and “a little” comfort and as my college roommate often says “ish” (complete-ish, certain-ish, confirmed-ish, etc…). Remember, if it’s clear others can see it too (so being in the fog means you can blaze new trails). Embrace fog.

So here’s the thing… Sprinting into the fog is never about stupid risk and being caviler… it simply means you must embrace operating with incomplete data… it means being 100% ok saying you were wrong, changing directions and navigating turbulence. I often say the single thing that can make an entrepreneur successful is being really good at navigating through change. It’s not about being RIGHT; it’s about taking smart risk, learning quickly and adjusting. Great entrepreneurs are wrong far more than they are right but they are really good at sprinting in the fog.

Photo credit: Figarogirl

Are you asking yourself the tough questions?

Sometimes in life, as we develop a bit of expertise or confidence, we can tend to hit cruise control… It becomes a little bit easier to slide by with less research before meetings, maybe a little more lax on the prep work and so forth… all because we are confident it will go fine, maybe it will even go well. And will my audience even really know I am just cruising?

But what if you took the time to ask yourself the really tough questions about your current performance.

Did I do every bit of research I could to ensure the best outcome?
Did I practice my investor pitch twenty-seven times?
Did I consider all the potential objections and how I would overcome them?
Could I do more?

Chances are you aren’t even close…

Can/should you take your foot off the gas sometimes? Absolutely.
Will honestly asking these questions change the arc of your life? Absolutely.

Being the best at something…. I mean being truly great and achieving breakout success means constantly looking in the mirror and asking yourself what more you could do (and then doing it).

Ask yourself a few more tough questions this year…

10 Ways to Light-up your startup

Entrepreneurs are always busy trying to run their companies... from answering the phone to taking out the trash... So sometimes we all need to remember what matters and what moves the needle.

Here are 10 things I think you should consider... Go light it up.

1. Taking risks is the #1 priority.

2. Re-read #1.

3. Momentum is your friend. You often have to "create it” with activity and effort. Don’t expect to “go viral”... work so hard that it just happens.

4. There needs to be a formula (MK was 1000 doors, $20,000 per door… Facebooks is expose each person to 7 friends within 10 days). Formulas drive tactics and strategy.

5. Don’t do anything big until you believe in your product… when you do, get it out in influential hands immediately, and often.

6. To make a great product you have to invest, try new things, test things, break things, fix things and repeat. This is a never ending process and you have to commit to it.

7. You (founders) are the best salesmen. Be vocal, be accessible… Be everywhere.

8. Work with only the best people. Be picky. (Hire slow and fire fast)

9. I love the saying that you are the average of the 5 people you spend the most time with… WOW, be picky about that for sure.

10. Your gut is often good, but test it, look at the data everyday and don’t have too much ego to change directions or say you were wrong… Winning is more important than saying “I knew I was right”… Just win!

Photo credit: herval

Why should I meet you? Or care?

I’ve been traveling a great deal lately and as it happens, when I travel, emails pile up quicker. Important emails from family, things I need to read, emails from my team and then quite a few “hey, I’d love to pick your brain OR do you have time for coffee” type emails.

Look, we all do it and I’m certainly no celebrity or global dignitary, but what I AM is extremely focused (or at least I try hard to be) and very busy. So here’s the issue… If I don’t know you, or you are a friend of a friend or an ex-classmate, that does not (unfortunately) mean I have the ability to prioritize a “coffee” with you.

Sound crass? Consider that 99% of startups fail. Consider that there are only 24 hours a day and I am a very committed father and husband who also wants to move the needle in both business and philanthropy… while never missing a Donuts with Dad or Indoor Soccer Match… that takes about 25 hours a day. I’m all about making it matter.

So here’s the point… When you email someone you probably have a good idea to run by them… Maybe an opportunity you believe they’ll benefit from or something really rare, cool, unique, etc… So you have to tell them. Be very specific and start with the WHY… why should they care? Why should they take the meeting? Why should they invest, leave their job, fly to your city, join your board, etc…

There is also sometimes a “gap” between what is meaningful to people… To some people $1000 is a fortune, to others it’s not worth a phone call (it’s all relative). Realize a seasoned entrepreneur may want/expect founder level equity to advise you or sit on your board (they have a reputation that carries big value, and is risky for them)… So do some homework and try to have a point of view on what moves the needle for them (sometimes it’s money, sometimes it’s equity… maybe it’s free technology, support of a favorite charity or an opportunity for their child… just make it matter).

So here’s my formula:

1. Tell them “what” in one sentence
2. Tell them WHY they should/would consider it
3. Give them actionable next steps
4. Suggest a time-frame
5. Thank them.

Quick example:
Mac, We’ve done our homework on you and believe you would make a perfect addition to the Acme.com, Inc. board of advisors.

We would be willing to make it worth your time by providing founder level equity in a startup that seems to fit your interests and also give you free use of our technology services (plenty of details to follow, but wanted you to know we are serious).

If this sounds interesting, please review our video (here) and our attached presentation. I think you will find it compelling and will agree there is a great fit. I would like to meet next week (how about Tuesday for lunch) to provide you a demo, and answer any questions you may have. Would that work?

Thanks for your time and consideration. Our board has already approved our adding you, should you decide to proceed with us. Looking forward to it.
Joe Smith

When I get that kind of email (which I rarely do), I react. I may be interested, but either way I am so impressed and appreciative of the research, approach and more than anything the thoughtfulness that allows me to make decisions quickly vs. GUESS at what they may want or even more, guess as to why I should be interested.

Make your emails count.

Photo credit: by epSos.de

Own your future... Be relevant

The world has changed (and will continue to evolve)… Where you went to school doesn’t matter. Your advanced degree? Not so much. Oh, you were top of your class, well I’m sure there are research departments in relevant companies, run by dropouts, that could use you… Am I anti-education? No way, I’m pro startup and pro-risk taking. I’m saying how you apply yourself is what matters…

So what drives the future now? Three things:


The world is full of smart people. They all may look like a bit like you. Good grades, check. Played sports, check. Civil service, check. So how to you achieve great things… How do you do something that matters and do it at scale… Or how do you get in the program you want or college you want… All great questions and the answer is generally the same.

The future belongs to the brave. The people who don’t wait for the perfect time or for the investment to come in. They don’t worry about pedigree or recommendations. The brave “own” their future… They own it by taking risks where others sit idly by. The get up two hours earlier than their peers. They do it NOW, not when all the stars align.

This is not self-help psycho-babble… this is real life. The people who run the most relevant companies in the world today are college drop-outs. The cures to cancer are more likely to be discovered by rogue scientist and independent thinkers who are outside the paradigm of current research.

Wake up and realize that you are just as capable as those you read about… If you have drive, and you go RISK-ON, focusing on things that matter then you can own a big future…

And come see me, we hire, partner with and invest in people like you all day long.

I heard a great quote recently from @Chamath (of Social + Capital and Facebook fame) about bankers… he said “Bankers are smart enough to be greedy, but not smart enough to be relevant”… Don’t be a banker (or insert plenty of other professions here), be relevant!

Photo credit: leetlegreenman

Ready, Fire… Repeat.

I get great responses when I blog or tweet about RISK…. You know why? Because deep down we all know we need to be taking risks. It is instinctual. It is part of our DNA. Amazing things (be that new lands or new lifesaving drugs) are rarely discovered walking a conventional path or waiting for orders. Sometimes you have to take action with the info you have, and then adjust mid-stream. This is an important part of taking calculated risks.

I recently posted about my trip to Normandy and Pont du Hoc (where on D-Day the Rangers scaled treacherous seas, then sheer 100 ft walls and took out German instillations). It is an amazing case study in taking calculated risks and taking action without full data. The American military had great intelligence about the geography and specific terrain but their compasses were off as they approached France, putting them 30+ minutes late for their landing and thereby taking away the element of surprise, and creating the need for many “real time” decisions once on land (it’s an amazing story you should read sometime)…

Anyway, just like battlefield strategy startups need to do their homework… You need to know your competitive marketplace. You need to know your customers. You have to research your technology platforms and spend ample time building the best team you can find… but at some point you just have to GO… you have to launch and then you have to react to the market before you have all the answers and data you need to ensure success.

Companies (my companies at least) rarely start and end with the same business plan. To me a great entrepreneur is someone who navigates through turbulence and chaos very well… and in the process they adjust strategies that take them closer to their market and their goals.

Too much time planning and you may miss your market opportunity.
Too much research and you may paralyze on data and decisions.
Too much thinking and too little doing is academic, not action.

So, do your homework, plot your strategy THEN TAKE ACTION… As my mom used to tell me, “there isn’t always a neon sign to light your way… sometimes you have to just have faith”…

So get “some” data, and then go build something amazing.

Photo credit: FunGi

Swing for the fences

I just spent the past few days in San Francisco participating in some great dialog about venture capital, startups, future oriented technology and so forth. I spent time one on one and in a group setting with a billionaire, a number of very smart venture capitalists, entrepreneurs, amazing startup CEOs, etc. A strong group for sure.

Here’s the take-away: take more risk!

Yes, you have heard me say it before and will likely hear it again. Risk is not a bad thing. As a matter of fact it is “not” taking risk that is so scary.

Do you know who VC’s invest in? They back people who want to change the world, create new markets, disrupt the status quo, and solve major problems. Those activities are not done by conservative cubicle dwellers or latter climbers...

Wait, what if you agree, you take a bit of risk and uh oh, YOU FAIL… then what?

I'll tell you... you are now MORE likely to raise a bigger venture round next time. You are more likely to get hired by another startup or see bigger career opportunities. Why, well, the answer is basically that those who take risks win. Smart people value the experience you have gained, the lessons learned and the fact that you were swinging for the fences on something that mattered. You stand out in a crowd.

My good friend (a successful entrepreneur turned talented VC) said it like this: “we want to back the guy who takes a big swing trying to do something amazing and fails… what we don’t want is the guy who builds a nice cash flowing small business and is happy with it… that isn’t interesting to us”.

So, gut-check… Are you taking enough risk?

Photo credit: curtis palmer

Dilution... sharing your precious equity

I am often asked about dilution. It’s a key question for most every entrepreneur who plans to go beyond a sole proprietorship. If you are bringing on investors, partners or employees you will likely face the question (can I have equity)…

I have a very clear view on the subject. Dilution is a bad word. Dilution implies you are losing something. I never GIVE anything away. I don’t “dilute” my companies or myself… I expand. I grow. I upgrade. I push the limits… And in that process I also “align interests” by sharing some of my prized equity for their networks, intellectual brilliance, work effort, products or ideas. But they are never gifts. Never.

If you want to change the world or just dominate the local pizza marketplace you might want to use your equity to incent others to jump in with you and help you achieve your dreams.

And yes, I’m a smaller piece of a bigger guy all day long…. So, although others may tell you that you are “diluting” yourself, remind them (and yourself) this isn’t dilution, you are trading equity for rocket fuel.

Photo credit: mrwynd