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.
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…
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.
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.
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.
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.
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.
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.
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.
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.