Ashley Bloom talks startup lessons, the investment mindset and futurism with the prolific entrepreneur, Dan Martell.

Feeling weary just before midnight, I was met by the steely gaze of Dan Martell, a proud Canadian, husband, and father of two young boys. He’s a five-time tech startup co-founder (two failed and formative, two successful acquisitions), frequent investor and 500 Startups mentor, with all his current focus on Clarity, a platform for paid business advice via phone calls.

Within a few minutes it’s as though I’ve downed a long black or two, buoyed by Dan’s high energy and very Canadian earnestness.

His biggest two lessons from failed startup number one (Maritime Vacation) and two (New Brunswick Host):

  1. He picked too small a market (Canada only, and the very specific niche of cottage vacations that was limited to a market of 300). The action step: Think bigger than your neighborhood, street and city.
  2. He picked a commoditized industry (web hosting) in which the margins are tiny, many customers demand service 24/7, and servers can break down at any time. The action step: Build a differentiated service/product (not a commodity) that cannot be easily replicated, or there will always be someone willing to do it cheaper than you.

Startup Truth Bombs and the investment mindset

Dan explains that since the DNA of the founding team is found in every aspect of a company, what matters more than oft-touted product-market fit is product-founder fit.

Why did you start Clarity?

When I started Clarity, I never thought there was a better idea that had such alignment with who I was as an individual, that I cared more about, as well as a business that could have a big impact… you see it in all the great companies, where the person had deep domain experience, a passion for the customer, and they couldn’t help but start a business to try and solve the problem… the bad examples are completely the opposite, where somebody shows up with a spreadsheet and says… “here’s the opportunity.”

What aspect of running a business is where you shine most?

My default state is trying to find the hardest, biggest problems in the business and solving them. Three months is the longest I can spend on one thing. That’s it. That’s my timeline… Once it’s figured out, I’ll build the team around it to execute. If it’s fundraising, I get it done is six weeks. After three months if it hasn’t made progress then either the problem’s not important, the people around the room are the wrong people, or something changes.

That question right there: ‘What do you want your day to look like?’ is way more important than how much money do you want in the bank. Because some people have $100M in the bank and their day is just totally fucked with back-to-back meetings. They’ve created this nest of bullshit that they have to be involved in. And they’re not happy, and they don’t know how to go back from it… Most people should start off saying ‘In 10 years, what do I want my day to look like?’ not how much money do I want to have.

Is your current business always your Everest? Can you see over the horizon?

I don’t imagine the next thing. To me, there’s enough opportunity in Clarity to be a $10B company… We’re going to be doing a big push into organisations with Clarity for Organizations, which we’ve already tested at 15 companies, where they’re deploying it to their employees. You can imagine the future of learning at companies and corporations. It’s for Millennials. People want self-directed learning. They don’t want to take a course. They want to talk to people who have experience that can give them context.

What’s ripe for investing now?

Anything I find interesting, I just invest in. I’m super bullish around Bitcoin, 3D Printing, Drones and Wearables.  I meet entrepreneurs through Clarity, which is great, since we have some of the smartest entrepreneurs in the world. I don’t need to build the companies anymore to feel like I’m still around and participating in these really disruptive technologies. I’ve done 33 investments, almost 34 now. The cool part is that it allows me to be interested in the new and innovative, but also continue the absolutely content focus on building Clarity into a big company.

Finding clarity and mentorship 

Your blog alludes to being on medication and having a wild upbringing, can you share more about this?

When I grew up, I had a pretty crazy lifestyle. I call it a colorful upbringing. The truth is, I just needed to find something to do that wasn’t illegal. No matter what it was, I was gonna go all the way with it.

This year I’ve already spoken to a dozen groups of kids that are in that kind of scenario. About 13-14 years old, to let them know that what they’re doing… the focus is wrong, but who they are and their skills are absolutely necessary and important and they’ve just gotta channel them.

Perhaps their talent is there, but not in the form of our current education system?

They are talented. That’s the funny part. I know. If I want anything in life… If I want money, I want love, I want relationships – all that stuff. You got to  put it out there first. To me, spending time with these troublemakers is paying it forward. I just can’t have it in my life unless I give it away.

Where would you be today without those sorts of mentors?

I wouldn’t be here, I’d be dead. That’s a guarantee. You can talk to anyone in my family. It’s really the power of the 15-minute conversation… [just like the] moment when someone pulled me aside and said to me, “This really isn’t for you,” and it was the first time in my whole life (at 16) that somebody said that. Even if it’s just the parents or the kids… anytime I’ve just gotten up and shared my story, I know one person out of 100 will change their direction. Because, what’s really important in all this and ties into Clarity is the messenger is more important than the message.

So you have two people go up and say the exact same talk. Me, who has gone through it, and somebody else who read the book. The guy who read the book, people are going to dismiss. Me, they’re going to listen…

So I know my responsibility as somebody who has gone through that specific scenario is to pay it forward, because it’s a very small amount of time that I believe can have a huge impact. So I’d be an idiot not to do it, plus I feel like the only reason I was ever given the opportunity to do this is because I was supposed to give it back.

There’s a great book called ‘Now Discover Your Strengths’. You know, stop trying to be great at things you’re not good at, but instead mitigate them so you’re not crippling yourself, but figure out the things you’re really great at and passionate about and double-down on those. That  was a turning point for me.

Futurism and technology

What do you see will change in tech and business as another ~2 billion people get on the Internet in the next five years?

Knowledge workers losing their jobs to marketplace freelancers. See article Five Reasons Half of You Will Be Freelancers in 2020.

Do you believe in Ray Kurzweil’s (futurist, inventor and Google director of engineering) assertion that a technological singularity will occur?

The biggest concern I have is around AI and how that plays out. When you have computers building other computers (seeing this already with 3D printers), then it’s really about the computers. With the advent of quantum computing coming online within the next 5-10 years, then AI will be a major issue.

What are the most exciting few companies in the world (besides yours) right now?

Less companies, more technologies:

About our writer // Ashley Bloom is a humanoid ball of stardust residing in Melbourne, Australia. One who enjoys writing, expansive living and multifaceted learning. Follow him on Twitter @AshtrayBroom.