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Personal blog by Mike Kirkup

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Three Yeahs

On Thursday night I was at Startups and Beer, talking with some other founders. Someone asked if I was enjoying building Elderella. I said "yeah." Then "yeah." Then "yeah" again — three of them, one for each of the three ways AI is transforming startups right now.

Mistake #6: Forcing humans to change

Today will be my last blog post on the mistakes I made at Arlo. I plan to continue writing but will have new lessons learned to share from Elderella and other startups I mentor. Arlo provided a lot of lessons learned (many the hard way) and in that sense I owe it a big thank you. At the same time, it has been two months since I last worked on Arlo and I don't want to risk too much hindsight in the…

Arlo Mistake #5 - Avoiding the Hard Integrations

As I outlined in my first mistake post, Arlo started as an internal tool and expanded from there. When we used it internally it had simple integrations with our Customer Relationship Management software (CRM) and Slack for notifications. This allowed our team to stay on top of changes.

Arlo Mistake #4 - Why we were blind to our AI's failures

We lost at least three accounts because our AI failed during customer demos, and we had no idea it would. We were flying blind without evals - the equivalent of shipping code without tests. This is how we learned that customers don't ask for evals; they just expect your product to work.

Announcing Elderella

I'm taking a break from my weekly posts on mistakes made at Arlo to share some exciting news: I am co-founding a new company with Jacqui Murphy called

Arlo Mistake #3 - I Recorded Every Sales Call. I Never Listened to Them.

I have written two so far on product related lessons learned and I feel like it would be a good time to switch over to go to market lessons learned.

Arlo Mistake #2 - Choosing features over product quality

As I mentioned in my last blog post, I made the mistake of building additional features onto our existing product instead of stepping back to truly analyze the workflow of customers. But that initial mistake led to another critical error: getting trapped on the feature treadmill itself.

Arlo Mistake #1 - Starting with a solution and not a problem

While starting with a solution before understanding the problem is a well-known mistake, we entrepreneurs still fall into this trap when it presents itself differently. Here's how I made this mistake at Arlo—and why it cost us months of development time and potential customers.

European Tour of Southwestern Ontario

The final instalment of the Superhero Challenge including the plot twists to keep life exciting right up to the end!

Day One – EnPowered’s First CTO

I have enjoyed bringing everyone along on my journey to find my new role at EnPowered. Today was my first day, and I wanted to share how it went!

I have a new job!

It has been a crazy three weeks since I announced that I was leaving Encircle. I have been truly blown away by the number of people who have reached out to catch up and share some of their ideas for my next adventure. I am excited to have found my new role.

What am I looking for?

Once one gets through the “why” question after announcing a big life change, the next follow up question is “what’s next” or “what are you looking for”. As I outlined in my previous blog post, I honestly don’t know.

Time for a new adventure

After 4 years at Encircle, I have decided it is time for a new adventure. Of course, when one makes a significant life change the obvious question is why? Sometimes there isn’t a clear answer – it is just time for a change. Time to try something new and to stretch my comfort zone.

Tribute to Phil Everson

I can remember the first day I met Phil Everson. I was standing in the Velocity Garage and it was the first day of the co-op term. Hope McCallum lead my marketing team and she had hired this gangly looking guy with red hair who couldn’t stop moving. You could just tell he was full of energy.