On Coming Up For Air

[Falling is More Productive with Friends • San Francisco is full of Friends • It’s Easier to Go Against the Grain When You Don’t See the Grain • Tech Doesn’t Sell Itself • Diving Deeper]

2025.03.02

LXXXIX

I was traveling this last week & next and have been going out of my way to spend time with both new & old friends. 

It’s been a while since I’ve done this, and it’s quite refreshing.

It’s also quite good timing–BirdDog is at another inflection point (perhaps startups always are) and this has been a good chance to reflect on where we are and what we need to do going forward.

[Falling is More Productive with Friends]

I learned to ski last week. It was hard & I fell many times. 

It reaffirmed a truth I’ve always held close to my heart–failing a lot is how you learn quickly.

It also reaffirmed something I don’t think about enough: community matters.

The guys I was with both taught me how to ski and also helped me when I was falling my way down the mountain. Learning at the pace I did would have been impossible without Kusal, and surviving would have been much more challenging if Eric didn’t help me on the way down. 

Because of them, I was able to do something that is objectively impressive: make it down three miles of blue on my first day skiing. 

[San Francisco is full of Friends]

I’ve said it before, and I’ll say it again–I like San Francisco a lot. The sun, the walkability, & the nature all make it pretty great.

The best part, though, has to be the people. Perhaps this is present elsewhere, but the kind of people I hang around in San Francisco have a very high openness to new experiences. 

I sent a message into a chat I’m in* with a bunch of people who I don’t know saying I was looking to hang out in SF, and a few hours later I had an invite to a(n) (e)bike ride from Presidio across the Golden Gate bridge and back.

I didn’t know anyone, but everyone was very open and friendly. And, perhaps surprisingly, perhaps not, I had some mutuals with some of them. 

We also all got to learn together that the other side of the Golden Gate Bridge is, in fact, out of the Lyft Bike service area, and that there is not a way to reactivate a Lyft bike that is out of the service area once it turns off.**

Thankfully, the UberXL cap of 6 people is a “soft limit” if you get a friendly enough driver.

All of that is to say that what makes San Francisco really great is the people. I crashed a hackathon, met founders in coffee shops, spent a lot of time at some hacker houses, and overall am having an amazing time meeting so many vibrant individuals.

If you’re one of them, I am grateful that you’ve come into my life.

*It has a high concentration of founders and may or may not involve a certain network state. 

**In similar transit related news, if a parking garage in SF says it closes at 9:15pm, it means that the car & garage are inaccessible for 10 hours after 9:15pm.

[It’s Easier to Go Against the Grain When You Don’t See the Grain]

There are pros and cons to such an environment. For me, someone who has been isolating in Michigan for the past n months, it’s pretty much all pros. The big thing that I could see being a con given prolonged exposure, though, is taking the patterns found in the city as ground truth.

As an example, there seems to be a pressure to raise capital here. Nearly every founder I met either has raised millions or wants to raise millions. 

That’s not bad at all, but it has become very clear to Jack and me that we don’t need to do that. While we are lucky that it is a viable option for us, and understand that it is not available everyone, it seems to be something that isn’t even on the table here. And perhaps it isn’t, if you are determined to take a business from 0 to 1 while living in a city like this.

Likewise, there is definitely a certain convergence on the technologies being used to power and build products. Again, not inherently bad at all. Rather, it’s just something that’s maybe hard to notice if you are constantly immersed in the city.

If I was here and I had not already validated our tech stack via “the market,” I might think we are doing something wrong due to how different it is from what I hear others using.

[Tech Doesn’t Sell Itself]

As to the BirdDog inflection point: we firmly believe that our tech is the best on the market for what it is supposed to do, users love it, and it is profitable–however, based on all of that, we think we have less revenue than we should.

On top of that, we had a competitor post about a new function in their product that effectively duplicates what our product does. I’m not so concerned about it in terms of quality, they explained how it works in a blog post and it appears to be an expensive o1 wrapper. I even went as far as to publicly challenge them to a live demo of both of our softwares.*

All of that is to say, in a way, the pressure is on. Even if this competitor is quite far from us, we are making enough noise to get attention. We now have to assume that there is some time period over which a competitor will be able to actually copy us. Not something to keep us up at night, but certainly something to apply at least a little bit more urgency. 

The solution? 

We have a decent motion for selling individual users our product, but we really should be focusing on selling to mid sized or large teams. One 22 year old I met out here closed a property management company on a $240K per annum contract. That is certainly a more complex sale than what we’ve been doing, but I don’t think it is 80x more complex than a $3K per annum contract. The deal only took him 3 weeks.

So, we are focused on greatly increasing our deal size. I won’t bore you on the details in this post, but I will say that in line with some of the above, we are going to create community and buzz around our tool at target orgs to show value and flip the sale on its head.

*Since BirdDog is “punching up”, they have no incentive to say yes or even acknowledge the post. Punching down is rarely a good decision.

[Diving Deeper]

My couple weeks of traveling have happened at a very nice time. 

While it’s much more challenging (if not impossible) to maintain the 7:30am-5:00pm, 7:30pm-10:30pm work cadence I have at home, that is okay. 

It’s been very fun and is a good frame break. Thank you to everyone who has made the last week an absolute joy & thank you to everyone who will make this next week a joy, too.

Sometimes, coming back up for air can help you dive deeper. 

Live Deeply,