I first heard of Google Helpouts on July 24th. It made perfect sense seeing that their video product – Hangouts – has been their “silver bullet” of social, it’s only logical. However, it’s not new. What they’re offering (consumer focused / expert video chat) has been tried in the past. In 2006 Skype launched something similar, only to shut it down. Since then there’s been a half dozen startups to enter the market offering something similar to Helpouts. Even eBay has a new service they’re testing in the UK.

All that being said, as someone who has a dog in the fight (i.e. expert network / advice as collaborative consumption), I think there’s some interesting aspects worth discussing.  So here goes.

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Almost a year ago I asked for a favor – a birthday wish – that everyone entrepreneur I know donate 1 hour of their time giving advice to another entrepreneur over the phone. That was the seed that has now grown into Clarity.

Since then we’ve

  • Retooled the product and launched publicly in May
  • Completed over 12,000 calls
  • Connected entrepreneurs from across 47 countries
  • Signed up over 7500+ experts & advisors

And today things continue to grow!

Today I’m super excited to annouce that Clarity has raise $1.6M in a round of funding from some of the best investors from Silicon Valley & across Canada.

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I believe that it takes more than innovation to succeed. It requires a great product experience. Apple definitely set the standard, but many new companies have embraced this trend and the bar has been set higher.

Product design will be a huge differentiator going forward especially when it comes to mobile and consumer applications.

Mobile web, displays and browser technologies have all elevated what’s possible now online and the expectation of our users. They expect more.

.. and I want to give it to them.

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Signup for Clarity

I was born on December 26th, 1979. Today I turned 32, although I still feel like I’m 17. Turning 30 was tough, but the past few years have been the most rewarding times of my life. Last summer I got engaged to a beautiful women and two weeks later we signed a term-sheet to sell Flowtown to Demandforce. Looking back to the successes I’ve had over the years, I realized that it wasn’t my upbringing or education that were critical in my achievements, but in the quality of the advice that I got from some amazing people along the way.

Have you had any of these types of conversations?

That’s why four weeks ago I started a company call Clarity that would enable this activity regardless of someones social status or geographic location. Clarity makes it easy to connect with others looking for advice over the phone. The service is all mobile, is private and secure, has some amazing features that make it fast and delightful.

So for my birthday this year I have one wish.

I’m asking every business owner, community leader and entrepreneur out there to offer one hour of their time – for free or for charity – to give 6 entrepreneurs 10 minutes of advice around their expertise or passion. Each call takes only 10 minutes. All calls are off the record, private (Clarity takes care of connecting both parties) and are filtered for quality.

Here’s how to commit your phone time:
1) Create an account
2) Block out an hour in your calendar January 5
3) On that day, promote your availability on Facebook / Twitter

We’ll be providing updates and instructions leading up to the big day. If at anytime you have questions, don’t hesitate to email me directly, or better yet, call :)

There’s already 300+ of the world best entrepreneurs, venture capitalist and marketers who’ve taken a pledge to give back and I would ask that you consider joining them. It’s only through advice from those who’ve been there before that we truly gain insight into the challenges we face as entrepreneurs.

There’s nothing that would make me happier then to end this day, my birthday, with a 1000+ amazing entrepreneurs giving me the best present I could imagine – their time and advice – for others to enjoy. Please take 10 seconds to sign-up for an event that will certainly move and change their life forever.

Signup here to give me the best birthday present ever.

Remember: It takes a village to raise an entrepreneur.

Man, it feels good to finally get that out!  As most of you know, I’m an open book with most things and keeping this great news private for the past 7 weeks has been extremely hard.

Too many people to thank

First off I want to thank my amazing team – Ethan, David, Assaf and Jerome.  Most people don’t realize that we’re only small team of five. Ethan and I have always believed that a small / talented / focused team could out innovate and execute better then one that’s bloated with sub-par people just to “get things done”. Even when we had 35,000 registered businesses on Flowtown – we made it work. The even cooler part is that everyone on the team is an entrepreneur. Everyone, before joining Flowtown full-time had their own companies or projects on the go, and they we’re willing to put their dreams on hold to be part of the Flowtown story. Today I’m proud to be able to publicly thank them for believing in us and our vision.

Why I’m excited

We found a place where we have 10x more resources to execute on a shared vision to improve marketing for small businesses all over the world. Demandforce has thousands of customers in several verticals and delivers millions of marketing messages a month. Our technology has already started to be integrated into their platform and our team is currently working on new and innovative ways to push the marketing envelope.

Two amazing people

All that being said I need to mention two amazing people, Renee and Ethan. Last August I became the luckiest guy on earth when Renee said yes! She’s been so supportive as we’ve been heads down on building out the company. Secondly, I want to thank Ethan for being an amazing co-founder and a best friend. Two weeks after getting engaged, I got a call from Ethan letting me know that paperwork was finalized with Demandforce. That was easily the best month of my life.

So what’s next?

Why do people love to ask me that question? The answer is who knows. I’ve been working with the executive team at Demandforce for the past few weeks and I’m really impressed. They’ve created an awesome company and I’m getting an opportunity to learn new and interesting things. Regardless of what the future holds, you can rest assured that whatever I do next – it will leave a dent on the world. Anything less is not worth getting out of bed for.

About Demandforce

Founded in 2003, Demandforce helps small businesses thrive in the Internet economy. The Demandforce D3 software-as-a-service application is used by thousands of customers to grow revenue, keep clients coming back, and manage operations more effectively. Demandforce’s flagship product, Demandforce D3, connects Demandforce clients to over 72 million consumers via email communications, text messaging and online services. Demandforce has achieved 24 quarters of over 80% year-over-year quarterly growth and is led by a management team with over a decade of experience developing and delivering web-based applications that drive real, tangible business value. Demandforce, Inc. is headquartered in San Francisco, CA. To learn more visit www.demandforce.com.

Down the Rabbit Hole and Back Again: The Story of Flowtown

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.

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


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?

Next week Ethan and I will be speaking at Berkeley to the MBA class that Steve Blank and Eric Ries created around Customer Development (CD) and Lean Startup.

Am I nervous? Heck yeah! Steve’s the God Father of CD and known for being brutally honest. All we can do is tell our story with as much passion and honesty as possible.

If you’re new to Customer Development or Lean Startup, be sure to read Steve Blanks blog, or his book: Four Steps to the Epiphany.

Last month in Boston I got to speak with a groups of statrups about Customer Development and the best feedback I got was “get straight to the stories, don’t focus on the mechanics … tell us what YOU did it – not how to do it.”. So with that feedback fresh in my mind, our talk next week will be 100% story based.

The 7 personal stories on Customer Development / Lean Startup I’ll be talking about:

  1. Customer Developement (CD) is freakin’ hard.
  2. Focus on the problem, not the solution.
  3. Don’t solve problems you’re not passionate about.
  4. Being good at sales is a bad thing.
  5. You need thick skin to do it right.
  6. Stop geeking out on the numbers.
  7. Pivoting to perfection (again, problem not solution)

Interested in stopping by? Learn how here.

Are you implementing Customer Development / Lean Startup processes in your startup? If so, what have you learned?

As a startup advisor and angel investor, one of the first things I try and teach every entrepreneur, is the importance of keeping advisors and investors in the loop.  With that in mind, I’ve created an email template that you should consider using.

Benefits of sending update emails

  • Have you’re advisers solve problems for you
  • No surprises, surprises are bad
  • Let your advisers celebrate your successes
  • Good news will go farther [lets us promote you!]

Best format and frequency

  • Put your most important challenges at the top
  • Short and sweet
  • Make it “Skimable” [bullets!]
  • Every 3 weeks (or if there’s any major issues news).

Other Tips


+ Top 3 Challenges
+ Metrics
+ Whats New / In The News

> Top 3 Challenges
1. Getting Press
2. Hiring Biz Dev
3. Building Sales Team

> Metrics
1. Revenue / Target
2. Return Usage / Retention

> Whats New / In The News
1. [Source] – [Title] [Shortend URL]
2. Hired Rails Programmer (@username)
3. New Customer – Fortune 500 company