With AI it’s the question, not the answer
With AI and operations, your answer will only be as good as your own experience.
My name is Rob. I write about operations and startups — and how to make both work.
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.
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.
Dilution
There is a cost of doing business — any business — and that cost always comes in the form of dilution.
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.
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.
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.
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.
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.
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.
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?”
Nurture vs Nature
This is a slight departure but for good reason. Both my kids graduated from high school today with a flourish.
Get aligned
Co-founders need to be aligned. Unified. Clear on objectives. To have a voice.
Deferral
Choosing the path to start your own company means a lot of things but mostly it means deferral.
The best laid plans
Startups, by their nature, are designed to be an uncontainable, uncontrollable and unstructured mess.
Should you say yes?
How often do you say “yes” to customer requests?
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.
What do you do for a living?
This is the hardest question to answer for founders.
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.
From anarchy to…less anarchy?
“Just f@cking do it.”
Identity
Title or outcome.
High effort or none at all
What gives a startup the highest chance for success?
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.
Is your story better than your product?
“We need you to remove your product right away. It is hurting our business.”
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.