Strategy

Let’s Fix Startup Board Meetings: 5 Sections To Flow

By | Leadership, Startups, Strategy | No Comments

Few things can shatter a founder’s confidence quicker than a poorly managed board meeting.

At best…

… you’ll get glossed over stares and “checked out” investors who secretly hate you for wasting their time.

At worst…

… you’ll accidentally knock over the first domino in getting kicked out of your own company.

Pay special attention to Step #4 in this week’s video to make sure that never happens. Read More

5 Simple But Powerful Ways to Lower SaaS Customer Churn

By | Growth Engine, Startups, Strategy | 4 Comments

Has a customer ever punched you in the face?

No?

Has it ever felt like that?

Every time I’ve had a customer sign-up, stick around for a few months, and cancel (aka churn) it sure feels that way.

It doesn’t matter how long I’ve been building businesses, nothing frustrates me more than having a customer that I spent a ton of time, energy and money attracting, leave because we missed the mark.

What’s different about my approach is that I take 110% accountability for customers churning. Read More

The 5 Parts of Every Business

By | Leadership, Startups, Strategy | 2 Comments

Do you remember the first time you had someone buy something from you?

For me it was when I convinced a bunch of bed & breakfast owners in Atlantic Canada to send me cash in the mail to have their property published online.

Still not sure if that was legal.

Suspect cash collection methods aside…

What they didn’t know is that I was a 17 year old kid with no formal “business.” Read More

The Ikea Effect: How To Use a Simple Analogy To Hire Your Next C-Level

By | Leadership, Startups, Strategy | 4 Comments

One of my favourite questions to ask someone is “Who’s the best [CMO/CTO/VP of Sales] you know?”

I don’t care if they already have a job… I just want their name.

Actually, I prefer if they’re already working because it allows me to build a relationship with them without the pressure.

My approach once I have a name is to reach out with a big, real-world challenge that I can get their advice on…

… usually the first contact lasts 15 minutes.

I’m just looking to establish a connection.

From there, I follow up and keep the conversation going and work them through my process for hiring.

But what if you don’t know anyone to ask? Read More

The 5 Growth Indicators Required To Build The Perfect Software Business

By | Growth Engine, Startups, Strategy | 5 Comments

Every startup wants to grow fast.

And while there’s value in modelling the tactics and strategies that have fueled the rapid success of companies they look up to…

There’s even MORE value in identifying the core, underlying principles that serve as the backbone for that success.

Over the years, I’ve identified 5 core elements behind the perfect software business.

I learned one of them directly from Jason Fried @ Basecamp.com when I visited Chicago to take his workshop over 10 years ago.

Another from guys like Mike McDerment @ Freshbooks.com, and Ben Chesnut @ MailChimp.com, both early mentors of mine who inspired a lot of the work I create at Flowtown.

In today’s world you see companies like Slack.com, and Intercom.com (disclosure: I’m an investor) shooting for the moon and you wonder:

“How did they do it?” Read More

3 Key Principles To Building a Software Company With No Money

By | Sales, Startups, Strategy | No Comments

Can you build a thriving software business without writing code?

Can you generate real revenues without having anything built?

The answer is yes, and I personally believe that it’s the only way to do it.

A couple weeks ago I was in San Francisco hosting my Sales Pipeline Intensive event for my SaaS Academy clients, and one of the speakers John (founder of five9.com, $1.2B saas company) echoed a similar sentiment…

It was funny because we hadn’t connected prior to his talk.

So I did some research on his latest company JetBridge.com, and it mentioned all the different areas they were innovating sales using AI/Machine Learning, and when he comes up, he just smiled and said “oh, all that’s bullshit” ???? Read More

How Startups Should Map Their Content Marketing Strategy To The Buyer’s Journey

By | Marketing, Startups, Strategy | 2 Comments

Wow, did I ever butcher this joke.

“The CEO, CFO, and Marketing Manager walk into the bar…”

You can watch the video below to see how I killed my stand-up career before it even started…

…but here’s what I was trying to convey.

Depending on WHO you are, you probably have a different need for the same outcome (i.e. a drink).

When I was building my startup Flowtown, we had customers who bought our product at $20/month, some at $200/month and even a few at $2K/month!

Were they the same? Yes and no. Read More

Where to find a code-cranking unicorn (aka CTO)

By | Leadership, Startups, Strategy | One Comment

Steve Jobs (Apple) had Steve Wozniak.
Mark Zuckerberg (Facebook) had Dustin Moskovitz.
Bill Gates (Microsoft) had Paul Allen.

Even though they could all code themselves, the greatest business leaders of our generation, all had a technical co-founder by their side.

Why?

They knew they’d need help building the actual product as their focus shifted to growing the business.

I had the same experience in my companies.

How did they find these people?

How did they convince them to join them in their vision? Read More

Why I had to crush a 15 year old’s dream (I’m not sorry)

By | Growth Engine, Startups, Strategy | 2 Comments

A few months ago I had lunch with a bunch of highschool aged entrepreneurs to give them feedback on their idea.

They were planning on building an energy generating play park for kids.

Now, I don’t mean to come off as a direct poo-pooer of dreams…

… but after 15 minutes of listening to their pitch I decided to ask some questions that I knew were going to shatter their excitement.

  1. Have you figured out the average time a kid plays on a play park?
  2. If they did play with your version of a swing, how much energy would it generate?
  3. Does that amount generate a sizable amount of energy?
  4. What’s the added cost to build a swing your way vs. the existing way?
  5. Does the assumed energy production cover the additional cost?

Read More

The 3 Activities of the SaaS Sales Process

By | Sales, Startups, Strategy | No Comments

What would it feel like hiring 150 sales people for your company in 6 months?

That’s the question I asked Scot, the founder of Classy, a few months ago.

Their story is EPIC!

I’ll fast track his answer… essentially, he started out for many years being the primary salesperson, then hired around him, but remained inseparable from that process.

After years of hustling and grinding he eventually hired his first VP of Sales.

I still remember our first advisory board meeting and how excited I got about their new plans to scale sales.

How did he do it? Read More

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