More coffee dates

My resolution this year is to say yes to more of those coffee dates you get asked to go on. They start like

Hey! I was wondering if I could grab a coffee with you and get your help with hunting for my next gig, been working as a growth PM for a year now and figured you’d be a good resource for tips on making my next move

Sometimes these are fishing expeditions, driven around getting a new job or introduction, but often, as advertisied, someone out there either looks up to you, respects your opinion or just wants to get your thoughts on something.

I always said no to these in the past. I took pride in it. Worse, sometimes I would just ignore them, or say yes, but then not actually book anything, so why didn’t I say no. I vow to change that this year.

So why did I stop staying yes? These meetups are time consuming, and right around the time I had my first kid, I started saying no. It coincided with a lot of Tim Ferriss reading / listening too, and I am sure the lesson in how to say no, didn’t help.

Why am I saying yes again? Because I couldn’t think of a good reason to say no. Obviously, I will still say no, but in 2023, I'm saying yes more often. To more coffee dates and more opportunities for learning. I'm going to walk away from all of these meetings with at least two new, meaningful connections, and that's something I'm really looking forward to. Tim Ferriss be dammed.

Consistency Is Hard

I will write a book, how hard can it be?

I think back to this article I read So You Want to be a Writer?, that prompted me to publicly commit and write this writing daily and back then, in September I committed to write 80 posts by the end of the year. I have written… 7.

Consistency is hard. I have read many books on habits, on kaizen, on daily improvement, all of that and all I have really learned is that consistency is hard. Am I too hard on myself though? I’ve got a busy day job, a healthy curiosity of side projects to keep my mind sharp, don’t forget the kids and my wife, not to mention my parents that are aging and need more help. Still, excuses.

So, what should I do? Give up? Say I was too ambitious? That is always the case, I am always too ambitious and I love that about me, so no, I will not give up, in fact, I will double down and recommit today to the process and idea of one post a day. It is November 15th, that means that we have 47 days until the end of the year. It’s a far cry from 80, but 47 would be pretty epic.

If we could put a betting market on this, what would my over under be?


When I was younger I spent a lot of time thinking about my legacy. Now, I do too but in a very different way. I came up in the age right after the dot com boom and bust. I learned how to program and build web and mobile apps in 2003. In fact, I remember getting a ride home with a friend of mine in Comp Sci in 3rd year who told me he picked up a book about Rails. I had no idea what he was talking about. I worshiped Musk, Thiel, Levchin, Rose, Ferriss and others. These were my tech idols and gods and I would join them in olympus soon.

That idea changed when I had kids as so many things do. I turned down a lucrative offer from Airbnb as it would have meant a move to San Francisco, something my wife and I didn’t want for our kids. I started realizing that the thing that a lot of people feel like they need and are chasing, I already had. I had a purpose and it was, these kids. This family.

As we move into the holiday season, I get more reflective. Choices I’ve made, doors that were open, now closed, new doors about to open. The constant is children, and family and life and legacy. I love the movie a Christmas Carol, I watch it 3-4 times a year around Christmas time. Different avatars, the best being Mickey’s Christmas Carol. I also love the movie the Family Man as I resonate with that character. I have a fear right now, that I am living in that life. That I will wake up ten years ago, to that time I almost moved to San Francisco and this path, this family filled life will be a dream that I can’t get back to and fades more and more over time. That’s why I have to enjoy each day, each moment here, as I could wake up tomorrow and know the choice I need to make.

There is no right or wrong way to do it, that much is clear. I do my best not to judge and be happy for people in life making choices, good and bad and living with those choices. I just know for me, as hard as it is to say, legacy is real and it trumps ambition.

VR Arcade Phase

VR is in the arcade phase. When I go to play a game, it looks amazing and fun, and when given the option between campaign or arcade, I pick arcade. The games are loud, often involve guns, and much like when I was at birthday parties back in the 90s they get boring after about 15 mins.

There are exceptions. Super Hot never dissapoints and I do love Horizon Workrooms as weird as I feel when I sit down to type at my computer in VR.

So I think about the opportunies that are waiting in the next 5-10 years and all you have to do is look back at video games.

We are in the waiting for Nintendo phase. As soon as someone build Mario for VR, not a port, not a fun arcade game, but something original and something that couldn’t be done on previous systems, that will be when VR goes mainsteam.

Recruiting via Problems

So I was thinking about that problem you are having, have you thought of…

This is when you know you have them. When they are ready to invest, or join your cause.

Like Cobb in Inception, you have planted an idea so deep into their that it is now living rent free in their mind. No, that analogy doesn’t even do it justice. Let’s try again.

You have planted a seed deep into their subconscious and not only is it living rent free in their head, but they are watering the seed. They are taking care of it, giving it sunlight. They want to see the seed grow. You get it, they are thinking about it unprompted and that is really cool.

This is how you recruit and enlist busy, awesome, intelligent and impactful people to your cause. You have conversations, you ask questions, you visualize a shared future together and you plant seeds. So how does this practically work, let’s cookbook it:

  1. Identify 5 people you would love to have on your side, to help you build something. Might be book, might be a movie, might be a company, might be a charity, this strategy works on all of them.
  2. Don’t pitch anything. Ask to get their thoughts and advice on a hard problem you are trying to solve. Could be over email, via Twitter, in person, on the phone, in VR, doesn’t matter. Just make contact
  3. Describe the problem.
  4. Wait for them to start asking questions or trying to help you solve the problem.
  5. Use We and start to build a shared vision of what the future could look like when the problem is solved.
  6. Leave the meeting and send a thank you email.
  7. Wait

Waiting is the crucial part of this. Detach yourself from the outcome and wait to see what you get back. If you get a

No problem Kent, good luck with your project.

Keep waiting.

If you hear nothing, that’s OK. It means you didn’t plan it deep enough, or the person isn’t the right person to help you.

What will happen more often than you think is you will get this email back a few days later:

No problem Kent, good luck with your project. Actually, I was thinking about X, have you considered Y.


No problem Kent, good luck with your project. I was able to find some notes that a competitor of yours gave us when they pitched that you might find useful.

These are gold, this means you have them. You have the chance to turn them into allies, investors, members of the team, advocates and hopefully friends.

If you don’t hear back, remember that people are busy and in a few weeks, send them an update and ask them another question or ask for their advice on something else. The key is that this has to be genuine, people can tell when you are faking these questions, so be real and ask something hard. In fact, the more technical the better. People love solving problems, and giving them a problem where they are expert and can solve it for you, might be the most fun part of their day. You are looking for a similar set of emails to the ones above.

Repeat this process with lots of important, smart, busy people. As many as you can find. People’s most scarce resource in life is time, so don’t waste it. If the meeting can be done in 10 mins, do it in 10 instead of 30. If you can get what you need via email, don’t do a call, etc. The more you do this, and watch the replies that come in, the more you will be able to see which folks in your idea resonating with and who simply isn’t interested. If you are going to work with something, or have them become an investor, or board member, you want them to be thinking about you and your company without telling them to, or without them feeling like they need to.

Get an idea, formulate hard problems around the idea, ask smart people to help you solve those problems, keep the ones that respond without being badgered close as this will be your future team.