Posts
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Slack is the Only Tool Where Losing Information is a Feature
Slack isn't broken. It's doing exactly what it was designed to do: let information disappear. The problem is you're storing permanent knowledge in a tool built to be ephemeral. Specialized tools hold specialized data. Your company brain holds everything that needs to be findable. Slack holds nothing. On purpose. If it needs to exist tomorrow, it doesn't belong in Slack.
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I Hired Smart People and Trained Them to Stop Thinking
The one you hired for their expertise stopped bringing ideas. The one who used to push back now just waits for direction. You didn't yell at anyone. You didn't shut anyone down. But somewhere along the way, you trained your team to stop thinking—and you didn't even notice you were doing it.
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You're Not Busy. You're Just Doing AI's Job.
Everyone's worried about AI taking jobs. They're asking the wrong question. Most of what we call work — synthesis, comparison, formatting, gathering data from six places — isn't thinking. It's assembly. And we've been doing it with the most expensive tool in the company: our brains. AI didn't take my investor reports or financial prep. It freed me from work that was never meant for a human in the first place.
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I Haven't Written a Line of Code in 25 Years. I Just Built 6 Apps.
I haven't touched code in 25 years. I just built six production apps that replaced subscriptions, cut hours of weekly work, and kept our dev team focused on the platform. The excuse that you're not technical just expired.
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Heroes Can't Scale
Our CEO became the lead sales person. Our CPO codes features himself. I've done deliveries when we were underwater. Every one of us has been the hero. And it's killing us. This isn't ego. It's passion. And passion without lanes is chaos. Heroes can't scale. Cogs can.
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We've Run Five Offsites. Here's What We Got Wrong
It took us five offsites to figure it out. Too much agenda. No strategy before. Momentum that evaporates the day you leave. This time we kept the team two extra days after the sessions ended. Just working together. It built culture and solved follow-through in one move.
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I Asked for a Bowl Once
I asked a hotel staff member for a larger bowl. He brought me one. The next morning it was already at my seat. Every morning after that, same thing. Nobody asked. He just remembered. That's customer service. The small thing that costs nothing but signals everything.
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Deferral
Founders defer pay, vacations, health, family, friendships. Everything. In the hopes it eventually works out. But the deferral rarely gets repaid. Fail, and you lose it all. Succeed, and you become an executive managing what you built. Either way, you become the thing you left.
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Hiring is lazy
We hired a team to manage routes, assign bonuses, and call couriers. It worked so well that leadership had no idea. We thought the system was running. It wasn't. People were running it. By the time we realized, the manual process was baked into our DNA.
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Chasing Everything Means Catching Nothing
Growth is slow, so we chase the next opportunity. But growth is slow because we never commit long enough to see if the plan works. The distraction causes the problem that justifies more distraction. We have to protect the plan long enough to know if it actually works.
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Every Merchant We Rushed to Launch, We Launched Twice
We wanted a merchant live in two weeks. Their team wasn't ready, so we built around them. They launched. It broke. Now we maintain that feature forever. Every shortcut we took to close faster became work we owned forever. The fix is patience.
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You're Broke. Stop Acting Like You're Not.
I've been at zero. Put my own money in to cover payroll. So I know the mistake most founders make when they get there: they keep operating like nothing changed. When you're broke, there's only one question: does this put money in the bank this week?
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We Finished Our 2026 Plan Two Weeks Ago. It's Already Wrong. Here's Why That's Fine.
Two weeks ago, I shared our 2026 plan. Six Canadian cities. Clear targets. The next day, an enterprise customer asked us to open seven American cities. Our CEO is in Denver right now. The goal doesn't change. The path just got a lot more interesting.
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Don't nickel and dime
Team members. Investors. Advisors. The Board. Everyone suggests ways to squeeze more from existing customers. Subscriptions. Surcharges. Box size fees. Every idea makes sense on a spreadsheet. We keep saying no. The discipline isn't saying no once. It's saying no every quarter when someone new brings the same idea with different math.
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How Long to Stay Confused at Scale
We spent $20K a month on marketing. Got 700 downloads. Ten deliveries. Seven customers. My cofounder wanted to kill it. I wanted data. Here's how we structured the uncertainty instead of pretending we knew the answer.
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Set the pace
A customer wanted us in six cities. So we opened six cities. Here's what a year of bleeding taught us about the difference between following and pace-setting.Retry
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Fast Software: Build What You Need, When You Need It
Building custom software for your exact needs is now faster and cheaper than subscribing to platforms built for everyone. Generic software is dying because you can build exactly what you need in days, not months—and keep it only as long as it's useful.
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10X Forces You to Stop Bullshitting Yourself
When you're trying to double revenue, every initiative looks promising. You can chase 50 different opportunities and convince yourself they all make sense. You'll waste months testing marginal improvements while your core business stays mediocre
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AI is just another layer, not the destination
AI isn't a destination but a service layer that will fade into the background of how business works.
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With AI it's the question, not the answer
With AI and operations, your answer will only be as good as your own experience.
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5 biggest mistakes I've made as a startup founder
No one is perfect and at the pace that startups operate at, mistakes happen often. What makes startups completely unique is that mistakes often mean progress, they mean you are testing the boundaries, trying new things.
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Making it manual
Senior team updates are important. Strike that. Senior team updates are VERY important. Something of this importance should not be left to automation.
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Dilution
There is a cost of doing business -- any business -- and that cost always comes in the form of dilution.
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The Entrepreneur Mindset
I've never really thought about what "being" an entrepreneur means. I figured it was pretty simple -- you are one or your aren't.
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Startups are hard to keep moving forward
Being a leader of a startup -- especially in any operations role -- is one of the hardest things to do properly in business.
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Challenge your team
The most important thing that leads to startup success (even more-so than luck, timing, hard work and persistence) is solving a problem in a different way from competitors.
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What's in your control
There are two business types: one you control and one that controls you. A co-founder who survived the pandemic and thrived by managing conservative cashflow and growing from profit shares insights. Unlike many overly reliant on investments, he prioritized sustainable, self-sufficient growth, illustrating the essence of true business control.
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Reasons NOT to join a startup
Startups are different beasts. If you've never been a part of one, it's really hard to explain just how unique and challenging it is to be part of one during its early stages. I've seen so many people think they want to be involved in a startup only to have the reality punch them in the face when they get what they want.
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Don't hate the VC
It's really easy to fall into the trap of hating on VCs if you are a startup looking for funding.
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The Founders bluff
When I started my first "real" company in the early days of the Internet era I was traveling with my immediate family to visit my mother in Bangladesh. I remember distinctly the fear I had but it wasn't about flying or malaria or anything related to the actual journey. It was what my answer was going to be when someone asked me "what do you do for a living?"
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Nurture vs Nature
This is a slight departure but for good reason. Both my kids graduated from high school today with a flourish.
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Get aligned
Co-founders need to be aligned. Unified. Clear on objectives. To have a voice.
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The best laid plans
Startups, by their nature, are designed to be an uncontainable, uncontrollable and unstructured mess.
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Should you say yes?
How often do you say "yes" to customer requests?
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The Startup Culture
Lots has been written about the importance of company culture and how to encourage it to develop and flourish in the right way.
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What do you do for a living?
This is the hardest question to answer for founders.
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Politics is a dirty word
As the US and potentially Canada gear up for elections, the ideological divisions are obviously quite deep. Each side feels that theirs is the righteous one and their party alone is the one that speaks the truth.
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From anarchy to...less anarchy?
"Just f@cking do it."
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Identity
Title or outcome.
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High effort or none at all
What gives a startup the highest chance for success?
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Embrace the silence
Great interviewers know that silence is a tool. They don't feel the need to fill the space left by a question or an answer. They soak in it and keep their mouths shut.
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Is your story better than your product?
"We need you to remove your product right away. It is hurting our business."
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You can't aim to sell
It is every startup team's hope -- that they are building something that puts them in front of someone else that wants to buy their company.
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THE decision-making framework
Some of us have a hard time making decisions. Period. We like to analyze options until we've backed ourselves into a corner and all of them have expired.
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The secret to scaling is stopping
Why myself and my co-founders of a delivery company spent months doing deliveries ourselves, and how that's the opposite of what most scaling advice tells you.
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Your Situation Room
After the disastrous Bay of Pigs invasion in 1961 -- attributed to a lack of up-to-date information -- President Kennedy ordered the creation of the Situation Room in the basement of the White House. Its sole purpose was to bring together the right people and information at the right time, mostly during a crisis, to make the most right decision available.
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How patient is too patient
How much patience should you have with employees in an early stage startup?
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Pull the future forward
Adult Mayflies live for 2 days. They spend a year as larvae, burst onto the scene with the sole purpose of mating and then, 2 days later, dead.
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Real VCs make decisions and move on
The all-too-common knock against venture capitalists is that they never make up their mind. They lead founders on, always asking for more proof points only to disappear or finally say no months too late.
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How startups can save $100,000
Early days in startup life feels like David Allen's GTD on amphetamines.
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Fighting Fiefdoms
This happens all too often in early stage companies.
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Options in tandem
The answer will be no.
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Earn your views
I love the simplicity of this statement: Earn your views. Views can mean something different to everyone but it's the "earn" part that hits for me.
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The alignment meeting
Remember that old adage that to assume makes an ass out of you and me? That's cute but in startups, assumptions derail initiatives and kill momentum. Nothing cute about that.
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I've actually spent my last penny
The story of the Christmas I wrote a cheque I couldn't cash — and what it taught me about the difference between "tight" and "broke."
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When do you add an operations lead
This is a question that not enough founders ask. The simple answer is right now.
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Why you aren't growing
This is a quick reminder of the simple principles that govern startup business life.
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Kill the (be)cause
Most of the challenges of building a business are a direct result of ignoring the "because".
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The lost art of resilience
Nobody explains resilience better than Rocky.
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The Bravado Bullshit
There is no part of a startup that is easy.
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Fighting overwhelm
Sometimes it's not doing too little that hurts a startup. It's doing too much at the same time.
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My worst meeting
It still haunts me.
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Digging holes
For a long time I didn't really understand what hard work is. Most young people don't but it's really not their fault.
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Distractions.
Running a start up is full-frontal. Things come at you from everywhere.
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Positioning.
It nearly broke us.
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Your mission
Business is self-serving and this is the problem.
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A simple price to pay
We tried dynamic pricing. It made perfect sense on paper. Here's why we killed it.
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Manual Productivity
New productivity app? I've tried it.
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The Urgent vs The Important
This is the biggest stumbling block for early stage companies
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The Founder Origin Story
Tobi was trying to sell snowboards online but couldn't find an adequate e-commerce platform = Shopify Travis and Garrett were trying to hail a cab in Paris and wondered why it couldn't be done with...
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Fast twitch + Slow twitch
Startups are a series of back-to-back marathons.
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Assume it's no
Raising any kind of investment outside of friends and family is one of the hardest things to do as a founder.
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Mad startup operating skills
In startups, operating discipline is a muscle but versatility is a skill.
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Fix your first impressions
Why customers decide to buy from your company is not a mystery anymore.
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Business actualization is bullshit
There is no "end", just a start and a whole lot of grey.
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The perilous plight of the fundraising CEO
There comes a point where the hunt for funding, the very air that startups need, will suffocate and stall the startup.
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Are you polishing a turd?
The ultimate test of a founder is to take the red pill.
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You are born with it
When I was 12 I was 5 years into magician lessons.
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Convenient for who?
If it's easy for you it will be hard for your customer.
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Don't aim. Execute
Zefram Cochrane is the first human to create a warp drive.
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The lens
I hadn't been to my optometrist since before the pandemic -- close to 5 years.
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Who you shouldn't hire first
As a founder of an early stage startup you just feel lucky when someone says they want to work with you on your idea.
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WHO are you building for?
How do you sell a house?
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You have my permission to micro manage
Founders, repeat after me: "It's ok to micro manage".
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The paradox of speed
Speed kills...but only if you aren't running a startup
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There's no coaching in startups
There are 2 cardinal rules in life: There is no crying in baseball and there is no coaching in startups.
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A single idea
There is nothing more powerful than a founder with one idea.
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Here's the rub of the funded startup
I don't mean they are in bankruptcy, I mean that early stage funded startups are always marching towards bankruptcy -- starting the first minute after that last raise.
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Nail your first metrics
When I was at Lyft the company was already a unicorn on its way to an IPO.
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The Hard truth about raising capital
The simple truth is that raising money for your startup is one of the hardest things you will ever do and it will take longer than you think.
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Take the right advice
I have sought and taken advice from so many people for so many different milestones over a lifetime of being an entrepreneur and a parent.
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Money DOES buy happiness
This lament is only ever spoken by someone who has money.
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Don't wait for hindsight
When I was twelve I discovered a life-changing album in Nebraska, Springsteen's 6th studio release sandwiched in between The River and Born in the USA.
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Speculation kills startups
High growth companies need to move quickly.
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Execute to execute
There are two givens operating any business: You get what you can afford and what got you here, won't get you there.
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Time under tension
There are 2 incredibly tough aspects of starting and running a business and they are both related to time under tension.
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Don't get fat
Scaling a company does not only mean revenue growth or geographic expansion or hiring or automation.
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You are a team not a family
To build a startup has no equal when it comes to pressure, strategy, proper execution and hiring (not recruiting -- hiring).
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Focus.
Profound change happens in a startup one dollar at a time and it is a founders job to make sure that stays in focus.
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Did I repeat myself? Did I repeat myself?
Nobody makes a purchase after 1 call.
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How to get a startup into orbit
The best advice I've ever read about starting a company is to not over-engineer the offering.
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Find a hole then fill it.
Product market fit is hard but so is building a business. You need to simplify and start looking for a hole to fill.
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To lead is not to own
When a startup moves to scale up, the biggest blocker happens to be the people that actually made that happen.
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You SHOULD cry over spilled blueberries
On March 17, 1845 the elastic band was patented by Stephen Perry.
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The law of balance in a startup
Balance in a startup has nothing to do with work or life.
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What's your death date?
Do you know when you are going to die?
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You CAN'T do it alone
His wife was a week away from giving birth, she was unemployed and I had to lay him off because I didn't see the obvious.
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Startups are NOT businesses
There is a misconception that you work FOR a startup.
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Tech layoffs and baseball
Why are we ok with massive technology layoffs? It doesn't happen in baseball, why should it happen in tech?
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Seizing momentum
For early stage companies, momentum is necessary. Without it you can't get off the ground but once you have it, you need to use it wisely.
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The Fast No
Getting a "fast no" is one of the most important things an entrepreneur can do to move a business forward. Here's why.
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Close the loop
Pandemic supply-chain issues aside, closing the loop is the ENTIRE goal of e-commerce: To enable customers to find and purchase product.
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Office...schmoffice...
Companies are waking up to the realization that they can be built with remote employees and that having a work from home first mentality can help it succeed
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Be unique or be gone
We’ve all heard the story of Billy Bean by now.
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Privacy vs Utility
We give away our privacy too easily and for little value. Consumers need to start thinking about how they provide their data and the return they get from it
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The REAL Innovators Dilemma
The real innovator's dilemma is not about disruptive technologies it is about the criticism that those entrepreneurs face building something new.
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Get one idea
It seems as though I am always consuming content.
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Fight for your people
Attracting top talent for your company is hard so why don't more companies put that much effort into keeping that talent when it arrives?
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A guy like me
Having someone that has experience building and growing a business is invaluable if you haven't done it before. The right experience at the right time helps
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Never confuse movement and action
Motion and action are completely different. One moves you around in circles, the other moves you along to your goal. Don't confuse them!
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How to operate in the new COVID-19 world
There are 5 considerations that need to be taken into consideration when operating a business during and after a pandemic.
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Fighting to not lose
I’ve had a number of conversations over the last couple of weeks during this pandemic about fighting to win versus fighting to not lose.
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A little clarity please
The biggest business killer is a lack of clarity. Leadership needs to define the direction for the company and let people execute on it or it will fail.
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You need to have a reading strategy
Successful people read books but you have to have a reading strategy in order to consume the right content in the right way.
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The four horsemen coming from the apocalypse
There are four trends that will be the defining economic movers during the recovery from COVID-19 and each will be more powerful when used together.
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Be the first to scale
Too much focus is on finding an innovative and unique idea. Companies should focus on executing on scale instead of finding the perfect idea.
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You need multiple streams
There comes a time for every business to decide to grow their line of products. Great companies take this challenge head on. The others fail.
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The Post-COVID downtown
When we emerge from self-isolation due to the COVID-19 pandemic, our downtown core will look drastically different due to work from home and unemployment.
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How to mentor right
Finding a mentor can be the most rewarding thing your can do. Learning from someone that has the experience you seek accelerates your growth.
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From hustler to operator
There comes a time in a business when it has to stop hustling and start operating. This may mean letting go the people that helped get the company started.
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Find the wedge
To simplify your business you need to figure out what the first step is in your grand vision to be able to execute on. FInd your wedge.
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Why hardware is so hard
Hardware can be a business moat but it also is very difficult to do propoerly. Here are 7 things that can derail it. Building hardware is hard.
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Love the work.
In order to get the right work, you need to love the work you do. There is something about being in the flow of work that you love.
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Check your ego
Ego is something that can be used as a weapon as an entrepreneur. The challenge is that too much ego repels but too little ego is forgetable. Find balance.
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For the love of it
When I was a kid I only loved Elvis Presley and baseball.
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Don’t fail fast, learn fast
As entrepreneurs we are told to fail fast but this is the wrong approach and gives us a reason to give up too early. Instead we should be learning fast.
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The message is the medium - How to use communications tools and avoid burnout
I used to think I had a screen problem and then everyone started working from home.
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The video call culture
I prefer video calls.
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Change in real time
COVID-19 has forced a decade of change in a short 2 months and those changes are just the beginning of how we reshape our economy.
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Was this a glitch in the Matrix?
Sometimes I honestly think we are living in a massive life simulation.
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The Canadian Innovation New Deal
Now is the time to pull out all the stops for Canada to regain its brand supremacy. We need to get behind the innovation is a real and meaninful way.
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What we can learn from American Idol
American Idol from home is a prime example of how to do performances and interviews from remote locations during self isolation.
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The first half century
Age was never something that shook me.
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Transparent leadership
Being a leader in good times is easy. It is by leading in uncertain time that you earn your leadership stripes and being transparent is step one.
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The right grey hairs
When I was in my 20’s and knew everything I would wonder why anyone would listen to ANYONE with grey hair.
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Survivors Remorse
Nearly 6 million Canadians have either lost their job or been impacted because of the pandemic so far.
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Delivery IS the product
Winning customers online starts when they buy your products and ends when the products arrive at their door and that delivery speed is the differentiator.
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Data is the New Electricity...not Oil
Data has been called the new oil but given that oil is used by all but controlled by few, we need to rethink this analogy. Data should be like electricity.
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The brotherhood and sisterhood of The Boss
I remember the first time I heard a Bruce Springsteen song.
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Get to the root
This world is way too complex.
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Are all habits bad?
So many books have been written about building habits.
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Why it’s hard to work from home
There used to be a stigma about working from home.
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Seeking deeper fulfillment
My mother was someone that I admired greatly.
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There HAS to be a plan
I’ve spent most of my life trying to avoid plans.
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The power of the very next
In 2016 my son Jack had a headache.
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The Great Leveling
I have been unemployed and it sucks.
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The End of Celebrity
In our old life celebrities brought with them intrigue, a glimpse to a better life, tossed with a little envy and a departure from day to day reality.
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Video: Why you should be where people love or where people hate - with Density founder Andrew Farah
There is a word that keeps cropping up when it comes to mobile anything - density.