Three years ago Farhan, David and I started Helpful to build the next generation of enterprise mobile products using AI. We focused on hard problems in fast growing companies for which there was a big market and no existing solution. Our small and awesome team built and launched three amazing products:

A Community for Dialog

Today Farhan Thawar, David Pardy and our team launched Dialog. It’s an experiment, and here is why…

Dialog is a community dedicated to live, spoken conversation online.

Social media has become toxic. Trolls, bots, and harsh comments polarize and destroy our ability to listen to and learn from each other.

We started Dialog as a passion project to create a space for intelligent, empathetic conversation. We know we can’t fix everything toxic on the internet. But we can create some different.

By Daniel Debow with David Pardy

Do you care about engagement?

Engagement is a fancy word for getting people to give a 💩. When people give a 💩 it triggers discretionary effort. Teams become proactive. People go above and beyond. The team knows what to do, how to do it, and they care enough to do it without being explicitly compelled. Engagement also has hidden benefits — alignment, strong bonds between employees, and simply having more fun through day-to-day operations and execution.

Great managers know that engaging their team is the highest-value action they can take.

Over the last 18…

Written by Daniel Debow and David Pardy

There’s an extremely long, drawn-out engagement crisis underway. It’s been happening for decades.

Disengagement is like a virus that spreads to all parts of the company — from the individual employee, to the team, the department, the customer, and ultimately net profit. It’s costing America hundreds of billions annually. Only 33% of American workers are actively engaged. 85% of executives agree that something must be done it.

The kicker? Nothing I’m saying is new. Businesses have been throwing mountains of money at this crisis but yesterday’s tactics just aren’t working. Given the global…

The anti-diversity manifesto written by a Google engineer and Uber’s sexual harassment probe have sparked needed discussions about sex-based discrimination and harassment in the technology industry. In the midst of this, I’m quietly hearing many well-intentioned men say they feel unfairly stereotyped as sexual harassers and abusers. “It’s a manhunt,” they say. They confide that they “get the issue”, but are “afraid of what I can say or do now.” These well-meaning men feel they are not complicit in the patriarchy and treat women with respect. Now, they say they feel victimized, ostracized, and singled out. …

Written by Daniel Debow & David Pardy

Smart young people (aka GPSGs — read more here) approach me for career advice a lot. Some ask how to become an entrepreneur, an angel investor, or even a VC (which I have never been). These 20-somethings are looking for something that can’t be found: a “path” to the career they want. This is an unfortunate myth. Any honest advisor will say that you can’t plan from that far out. You have to stumble into it.

This lesson sunk in when I was a co-founder at Rypple. At the time, I was trying…

This is a story about how to iterate your company’s high-level positioning to inspire customers and prospects as your company grows. I also cover how to piss people off to your advantage. Read on.

Before diving into tactics, let’s have another short refresher on Geoff Moore’s masterful depiction of The Big Scary Chasm (from Crossing the Chasm). Geoff’s insight was that different groups of people have different attitudes toward adopting technology, so you should market to them differently. Innovators want something visionary. Early Adopters want a competitive advantage from tech. The Early Majority wants pragmatic business results validated by customers…

People endlessly compare business to sports or war. These analogies have never really resonated for me. I’m not much of an athlete. And thankfully, I’ve never been to war. Instead, I relate to music. And I think that the creation of music has some great lessons for teams in business.

I love improvisational forms of music, like jazz, in which artists create unique interpretations on the spot. Musicians can seemingly read each other’s minds as they adapt and synchronously respond to each other.

Through my experience as a co-owner and bassist at The Root Down Studio, I found out that…

What makes you happy in life? Do you think buying a new thing makes you happy?

According to research from San Francisco State University, the answer is “no.” The study found that people who invest in experiences, rather than stuff, are happier.

Sure, you’ll enjoy the thrill of anticipation before you purchase a new gadget. But once the anticipation fades, you won’t be any happier. In fact, you might feel stressed when you see your next credit card statement.

Meanwhile, your life experiences — whether you invest in travel, a hobby, or fun times with friends — will make you…

A couple of years ago I gave a talk in Halifax at Startup Empire called Killing It with Vision. Even though it’s been years, people still ask me about it. So, I thought I’d write a few posts to expand on the ideas I presented, around what vision is, and how you can use it to sell product and build your company.

Let me start by defining vision. Your vision is a simple, inspiring story about the future. I want to emphasize the word inspiring. I don’t mean the kind of inspiration that just makes someone say, “I feel good.”…

daniel debow

Dad of 4, CEO of, ex-Salesforce SVP, founding team at Rypple & Workbrain, angel investor, bass player, adjunct prof @UofTLaw and curious person.

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