In San Francisco, being an Entrepreneur puts you at the top of the food chain and failing is worn like a badge of honor, so most people can’t wait to jump into a pool full of startup Kool-Aid. Even the non-swimmers.

The problem is they think it’s all about working at coffee shops, raising a lot of money and speaking at conferences. If they get funded, they act like they’ve made a sound career decision, one that led to a promotion. Trouble is, it isn’t true.

Most entrepreneurs are like artists: passionate and starving

I’m not sure when being an entrepreneur turned into a career but it’s a dangerous way to look at it. It’s like waking up one day deciding to become an artist. You don’t decide to become an artist, it comes from a passion to create.

Also, it seems more and more people are starting up for the money (or the hopes of it). Wow, are they misguided. It’s way easier to become an investment banker than to have a successful outcome as a tech start-up. The odds are not in the entrepreneur’s favor.

It’s more than being a risk taker

At the end of the day, it’s not about taking risk. Yep, I said it. Sure there’s risk involved, but it’s not why you start up. For most, it’s about creating something from nothing. I don’t care about money. I don’t care about materials. All I care about is creating something that others use and find valuable. There’s definitely ego involved, any creative act requires it.

It’s who you are … all you know.

How you become an entrepreneur can take many different paths but I’m certainly not working for someone else. At this point, it’s who I am and all I know. Some feel that they can’t do it forever because they have plans on starting a family or can’t sustain the intensity – well I disagree. It’s sustainable if you choose. It doesn’t have to mean risking it all, or working 100 hours a week. It’s more like waves that come and go and if you manage it properly, it’s doable. I can’t see myself doing anything else – building companies is what I love to do.

I’m not writing this to discourage people from starting. I’m hoping people read it in order to help them prepare. Entrepreneurship is definitely not for the faint of heart. It’s certainly not a career move either, it’s something you do for the rest of you life.

P.S.Lately I’ve been writing twice a week at http://maplebutter.com – it’s a blog I started for Canadian founders – be sure to subscribe.

Where will you be July 13th? I’ll be co-hosting the International Startup Festival in Montreal with some of the brightest and smartest minds in the startup world. The startup festival is a two-day conference on the business of startups. It brings together industry veterans and fresh faces, thought leaders and technology giants from around the world, for a series of lean, fast-paced events. It includes startup launches, inspiring keynotes, and deep-dives into hot sectors like mobility, social networking, and gaming.

Apply to pitch your startup!

Phil Telio (Exec. Dir of Startup Festival) and I had a chance to catch up today and talk about why startups need to attend this and what’s to expect (fyi Fireworks!!!).

This event is one of many that are occurring across Canada, and is a big step towards innovation and supporting startups across the country. If you can find me .. beers are on me. Can’t wait to see you all in July!

It’s that time of year again – conference season. Below is a list of events and talks I’ll be giving at each.  So far I’ve got 11 nailed down with a few more being figured out. I love speaking and connecting with amazing people – it’s what fuels me. If you’re going to the event (or want to and need a discount code ;) , or you’re from that city, leave a comment below and be sure to include your twitter username. I would love to connect in person.

InboxLove, Feb 25 in Mountain View

Email and Social Marketing

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LeadsCon 2011, Mar 2 in Las Vegas

Getting Social & Mobile

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1K On The Side w/ Ramit Sethi, Mar 7 (Online)

Marketing Metrics and More

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Mar 3: Berkeley-Columbia Exec MBA Class

Startup Talk

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Social Marketing for Startups, Mar 7 in SF

Social Marketing 202

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The Lean Startup SXSW, Mar 12 in Austin

Lean Product Development: Timely.is Case Study

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Dogpatch, Mar 20 in San Franciso

Activity Streams and Cohort Metrics for Startups

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BigOmaha, May 11-13th in Omaha,

Lean Product Development: Learning is the Killer App

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The Michigan Lean Startup Conf, May 19th in GrandRapids

Lean Product Development: Learning is the Killer App

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Startup Lessons Learn Conf, May 23 in SF

Case Study: Flowtown

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MoSo Conference, June 16 in Saskatoon

Social Marketing: Hustlin’ for ROI

Be sure to leave a comment below if you’re attending any of the events and want to connect in person.

Zack big ollie
As a teenager I was a “skater.” One of those kids who hang out downtown and annoy the pedestrians. Skateboarding is how I spent my teenage years. Was I any good? I like to think so.  Toward the end of my skating days, I almost got my 360 flips down, used to olley the big 5 at Assumption, and even landed some pretty big backside heel flips off the parking garage.

In many ways, spending most of my days skipping class and hanging out with my friends laid a solid foundation for the way I look at business today.

1. Focus On Your Passions

Winchester Skate park pool Judi O

Ask my parents and they’ll tell you I loved skateboarding and hanging out with my friends – maybe too much. There were times I’d jump on my bike to head 10 kilometers for a 2 hour session with some friends. And oh, the times when I’d get a new board! I’d even sleep with it next to me just so when I woke up I could see it was real and that I wasn’t just dreaming.

Passion is a powerful force. If you’re in a business you’re absolutely passionate about – the work, the long days and nights get easier. With passion, persistence never wavers and even on the darkest days – and they will come – you’ll be able to plow forward.

I’ve been fortunate to do only what I’m passionate about since turning 19. So what am I telling you? Find something that fires your passions and the money will come.

2. Take Risk and Go Big!

Unity Day

There were countless times while skating when I was confronted by a new set of stairs or drop and someone would ask “Hey, Dan – are you going to do it?”

As I got more skilled and more confident, “YES!” became my go-to answer, even if I was scared shitless.

Don’t underestimate me when I say shitless. I’m talking deep-down dread in the bones scared, like if I don’t pull this off I’m going to be hurting bad. But you know what? More times than not, it worked out. Maybe I didn’t always land well or land at all, but I didn’t wind up in the hospital and, on a few occasions, I actually pulled it off. Nothing feels better.

Like going for the big land, entrepreneurship is about risk. The bigger the risk, the bigger the reward. What skateboarding taught me was not to sell myself short – we’re all capable of bigger and better. Of course, on some days you will come up short, but if you get up and try again, you may just land it – and it’s on that day that all the other falls and fails that came before will feel worth it.

3. It’s All In Your Mind

Lost In Thought

Push, push, push, setup and go … you’re in the air, you flick the board and BAM! You miss the grip and come up short, crashing hard. You get back up, brush yourself off, stop, look at the terrain and visualize how it should be done. You close your eyes and try to “feel” how it should feel, picturing your landing being executed perfectly.

That’s how great skateboarders do it. Guess what? Business is no different. Even today, I stop, take out paper and sketch things – situations, environments, outcomes – and try to visualize the outcomes I want. Whatever that may be – a happy customer, positive reviews, someone saying “yes”, or a building full of amazing and talented people creating a huge amazing company.

Ten years later, even though I still bear the scars, I’m doing it the same way.

4. Show Some Style

Style

Landing the trick was one thing. Looking good at it was another. Some skaters I used to ride with had great technical skills, but lacked style. It reminded me of watching a robot skate. Impressive, but lacking soul.

Contrast that with a skater who can ollie, but ollie with style and that’s a skater who makes you stop and stare. In business, there are thousands of ways to make pure cash, but in my mind, you need to have style, too. It’s about how you did it and how people around you felt. Adding style to the way you do business will make the world stop and stare – and it feels great when they do.

5. Progress And Progression

Parkour Team

Nothing progressed my skills more as a young skater than just hanging out with the older, more talented skateboarders. They took me under their wing, showed me things I never thought were possible, and most importantly, encouraged me along. There were moments when my landing even the simplest trick was a reason to celebrate – for me and them – It was all about progression!

As long as your business is progressing, no matter where you start, it’s a reason to celebrate. I’m still reminded of that when I meet a first time entrepreneur who’s launched a new business, raised funding, or made a key hire. I get stoked for them, even if it’s a little progress, just like my skating mentors did for me.
Life teaches us good lessons when we pay attention. I still enjoy learning how things work (or don’t) to see which ideas are worth emulating for my own business. Skateboarding was my launching pad and I’m forever grateful that my parents supported me, even when their better judgement might have told them otherwise.

What sport, industry or situation have you drawn inspiration from for your business?

Foot in mouth

Here’s a lesson in how to put your foot in your mouth – email your start-up friends and tell them that no one is doing anything to create a community in Canada.  That was me today in a Maple Butter update. I choose the wrong words and lacked context to make a point. Canada has some amazing groups – like Startup North, Sprouter, StartupCampLaunchParty, NextMontreal, StartupDrinks, DemoCamp only to name a few - working hard to build this community.  I know when I’ve made a mistake.  I’m sorry.

There's a pool party at sunset - everyone mark your chair with a towel

January 1st is a great day to look back and reflect on what you’ve accomplished.  As I think about my time, and how I’ve spent it, I’ve realized there’s some good habits I’ve created that have given me the most leverage.  Here’s a few ideas on how you can get more time back, and keep your new years resolutions in 2011!

1. Structure Your Day

The best advice I ever received was to create positive habits.  Simple, yes – but powerful.  For me, that means doing certain types of work, and in a certain way, at specific times of the day.  Overtime I’ve learned that starting the morning figuring out my big rocks, and moving those forward have the highest value for me.  Also, paperwork and creating “work products” are best done in the morning or at night – with the afternoons spent talking and collaborating with others – its keeps the energy flowing.  Having this structure means you can quickly understand where a task fits and know what you can realistically get done.

2. Ask For Help

There’s no reason to go in it alone.  If you know there’s someone out there than can get you moving along faster or in a smarter way, you’re best to ask for help. Even if you have to pay them – this can provide huge leverage and accountability.  I’ve had a virtual assistant for 5+ years now and have hired many consultants, trainers and specialist for various projects – if chosen correctly, it can be money well spent.

3. Have Them Follow Up

When people send an email or call and say, “hey, I’ll be in town next month – we should connect”, the best way to respond is to ask them to follow up a couple days beforehand.  This keeps your calendar clean and puts the follow up action on their plate, not yours.  It’s only fair.

4. Politely Say No

The great part about being in a startup and having some many great people in the community as supporters is that you’ll frequently get asked to participate in something; conference, demo, business development deal, etc.  however, these can be a huge time commitment.  The best way to approach something is to say no by default, until otherwise given reasons where the alignment with your new years resolutions make sense.  Yes, I know, sometimes you’re doing someone a favor, and you should help out – but I’m taling in general.  Respect your time – it’s easier to say no to something up front, then commit and back out at the last minute cause you’re getting pulled from your team. (I’ve had to do this, it sucks).

5. Share With Others

The best way to hold yourself accountable is to tell the world what you’re planning to accomplish. This way, you’ll have positive peer pressure implemented and it will certainly help you keep that commitment with yourself and others.

6. Leverage Your Health

If you’re trying to implement a time management process and you eat like crap, then I think you’ve got it backwards.  Most tasks or projects require energy, not time management – and if you’re not healthy, especially eating really bad lunches – only to go into a comatose for the whole afternoon – then you’re missing the point.  You need to have your health – energy is the biggest leverage for getting anything done. Think about it.

7. Learn To Communicate

If you’re trying to get anything done in life, it’ll probably require some level of collaboration.  The ability to communicate your ideas and vision is crucial in getting anything done.  It’s why I learned how to use OmniGraffle to create product mockups (also LOVE Balsamiq) and decided to blog more this year.  The biggest gain in productivity are simple ideas with huge impact communicated with clarity.  Invest the time in learning a new application to help with this, even if it’s only excel or powerpoint.

8. Less is More

Instead of making a list of 10 things you want to get done this year, why not choose 1?  What single goal, that if you accomplished, would have the highest impact on your life.  Do that.  Don’t “try” and do 10 at a time.  Pick one, say no to the desire to do too much, and you’ll likely get it done. Having 10 things half tried and not completed won’t make you feel good.

“.. most people overestimate what they can accomplish in a year – and underestimate what they can achieve in a decade!” ~ Tony Robbins

9. Bring People Together
This is a super high value tip.  If people are constantly asking you for 15 minutes to pick your brain, or want to meetup – it’s actually best to bring 3-5 of those people together with you and connect them all together.  Not only will it add tremendous value to their ideas and conversations, you can kill 2 birds with one stone and actually get way more out of the interactions.

Bonus: JFDI

You can google the definition of JFDI, but I’m sure you can figure it out.  At the end of the day, take the first smallest step.  Action always trumps thinking about it – there’s so much more you learn when you actually do.  Get rid of the knowing, doing gap in your life and you’ll be amazed by what you can get done.

Got any other tips? Love to hear from you in the comments below.

Here’s to a kick ass 2011!

Entering the Forest Alone

Photo – Entering the Forest Alone

If I wasn’t doing my startup in San Francisco, here’s some random thoughts on how I would do it in another city – most likely in my home town of Moncton, NB.

1. Start.  Build something. Launch. #JFDI

2. Ping friends on Skype and ask them to full screen share and do ad-hoc user testing.

3. Sit down once a week, in person ( you need to see their pupils dilate ) with potential customers to learn about their reality and problems.  Go to their office, see how they work and watch them try and use your application.  #Humbling.

4. Spend at least 50% of your day writing code and fixing things that you learned from your in person meetings. #Iterate

5. Read books (not blogs) on psychology, marketing and persuasion.

6. Build an admin dashboard that monitors high-level conversions (visitors, signups, activation, upgrades) and customer activities (essentially a “news feed“) so you can learn.

7. Once a week I would call (not email) someone brilliant who lives in the valley to get their advice on a specific marketing or product idea.  Call it getting the “pulse” of whats working and whats not.

8. Once every 2 weeks I would host a call with 3 other amazing Entrepreneurs and ask them about their top challenges, try and help out and keep in touch.

9. Run paid ads ($10 / day) to a landing page application so you can have a consistent amount of signups everyday to learn and iterate.

10. Survey your users in cohorts and try and understand why they signed up, what problem they thought you were solving and the greatest benefit they received from your application.

11. Keep the team small (2-3 people) and insure they are all extremely talented (only hire A+).

12. No government programs or grants.  They distract you.

13. Read TechCrunch, Eric Ries, Steve Blank, Dave McClure, Marc Suster & Chris Dixon

14. Follow everyone on Twitter from this list

15. Only hang out with entrepreneurs (any industry will do).

Anything you would add?

Quotes from the video:

  • When you want to succeed, as bad as you want to breath, then you will be successful
  • When you get to a point, that you want to be successful – as bad as you want to breath – then you will be successful
  • Most of you don’t want success as much as you want to sleep.
  • “Sleep is for those people who are broke” 50 Cent (video)
  • You will never be success until you don’t need a dime to do what you do

What message did you like most from this video? (leave a comment below)

Do you really need to move to the valley?  I get asked this question a lot.  The better question should be – Why should you move?  Two years ago, on this day (Sep 1st) I boarded a plane destined to San Francisco with nothing more than a suitcase and a mountain bike.  I had no plan. I didn’t know anyone.  All I knew is that I wanted to be where all the action was.

Here are the reasons why.

To Play a Bigger Game

This is powerful, so read it slow.

“Are your goals worthy of your life?”

That was the question that got stuck in my head the summer of 2008.  Essentially, was I thinking big enough? Was I playing a big enough game?  Even though I wasn’t sure what I wanted to do next, I knew I would figure it out and go big.

The great thing about San Francisco is you’re ALLOWED to think big. HUGE. Be Crazy!???

Imagine that.

Actually, if you don’t – people will question you on it. Why aren’t you going after a huge market? It’s the same energy / time, isn’t it?

The reality is, people here are playing big games and if you want to belong, you need to do the same.

It’s been quite liberating actually.

Scare Yourself Every Once In A While

If you don’t do something everyday that scares you, then you’re probably not pushing yourself far enough.

Here’s a simple exercise: Every time you buy something today, ask for a discount. Yep, everytime.  How do you feel? Scary right? Well, after a while – it goes away and you’ve grown as a person.

When I moved, I made myself a promise that I would continue to do so.  It’s gotten to the point now, that if I’m asked to do something, or go somewhere’s where I’m like “???? What, How, What do I say, etc” – I say YES by default.

Eventually I figure it out.

Yes, sometimes I fall flat on my face .. but overall I’m way ahead and probably learned the most about myself and the situation in those moments.

Moving to San Francisco was scary, but it was also one of the best decisions I’ve made in my life.

Getting Advice From The Right People

Here’s a real simple question.  ”What % of your conversations (or friends) are related to your startup / passions?”.  Since I’ve move to San Francisco – I would say for me, it’s easily 85%.  When I was in Moncton, NB (Canada), more like 5-10%!?

It’s not only the conversations, it’s the people.

I have a belief that you should ONLY seek advice from someone who’s DONE what you’re trying to accomplish.

That’s a huge idea if you think about it.

The beauty of this city is there’s an endless list of people who’ve already paved the road for you. It’s like everyones paying it forward.  It’s a beautiful thing.

If you can drink from the fire hose, the information and experience is here.  It’s intense and fun all at the same time, so be sure to set some time aside to actually DO. :-)

(I would’ve love to list everyone who’s given me advice and pushed me forward over the past 2 years, but it would be huge.  If you got my email – you’re one of them.  Just wanted to say thanks!!)

Feeling Alive Everyday

When people ask how I like San Francisco, I always say “… out of 10, it’s like an 11″.  Honestly, it’s like they created a city around all my passions (startups, running, great food and snowboarding).

This city is full of amazing opportunities to experience the most ridiculous things in the world.

I remember one day I came out of my apartment and there was a group of 50+ people standing there not wearing any pants?!  I guess I didn’t get the memo re: Don’t Wear Pants Day.  Everything from Facebook F8 event to Bay to Breakers, this city will make you feel alive!

So What’s Next?

With things moving quickly at Flowtown, I don’t see myself doing much else.  I’m the type of guy that once I bite into something, I don’t let go.  Will I travel, yes.  Will I continue to advise startups, of course.

All I know is that I feel absolutely fulfilled right now, and want to keep that feeling.

So, with that – thanks for being a reader, supporter and friend.

If were friends, met in person, or even exchanged tweets, please leave a comment .. would love to hear from you.

Thank you.