Today I’m more grateful than anything to have been born here and I’m proud to be an American. The people who came here before us came with and idea that became a country.

Today isn’t about the exact history, dramas, or successes but about the idea of creating a union dedicated to certain rights like life, liberty and the pursuit of happiness under God. My personal opinion is that this structure wasn’t our doing but instead a collective and powerful display of faith in the face of fear. It was that same faith, ingenuity, and grace that helped our ancestors put a man on the moon, defeat evil regimes, be safe harbor to those building better lives, and be a foundational building block that holds the world together. Within that idea, there’s a responsibility on our generation to keep doing the same and to understand the principles we were founded on and choose to live by.

Eat some hotdogs, and remember to have fun responsibly. Right now there are some people who will wake up tomorrow without a hand as a result of playing with fireworks. Choose hands. I hope everyone reading has a happy 4th of July!

This morning I picked up this book off my bookshelf and quickly blew through in a couple hours which I’ve been meaning to read for a long while. It’s by one of my favorite people, Brad Feld, who I was lucky enough to work for briefly while I was in college.

One principle that’s been a guide for me over the past ~2 years is to find people who have what you want and ask them how they got there (and don’t care what anyone else thinks). Brad has what I want; he’s very successful, but continues to be kind, generous with his time and energy, and thoughtful beyond required even in the toughest situations I’ve seen him in. I’m very grateful to have Brad as someone in my world to look at as an example of someone who can be both a good person and successful. When Brad publishes a book that talk about how he got there it seemed smart to read it. He’s also blogged about this stuff for a couple of decades which if you’re ever interested is a treasure trove of wisdom.

A few of the biggest take-aways I had:

1. The universe expands your opportunities proportional your willingness to accept randomness

When I was in college both Brad and David Cohen did these days called “random days.“ I doubt Cohen knows who I am, but I actually met him first at one of these random days during Boulder Startup Week in 2016. It was interesting to me to learn that this is actually how Brad and David met and how Techstars got started.

Your lucky break lives in the tail of the distribution on a random Tuesday from someone you’ve never met before. Your ability to see it is having the willingness to consider that these opportunities that you might have never seen as an option.

2. The energy you give comes back in multiples, you just don’t know from where

The central tenant of this book is giving without expectation. The nuance is that the goal is to not be transactional, but to still expect something to come back you, just without being prescriptive from where. It’s the virtuous cycle of giving time and energy that brings unique opportunities that you wouldn’t find anywhere else.

3. Respond to every email

This is tied to the first two, but Brad includes some great strategies for scaling yourself even when you don’t have time through loaning out your network. It’s the opposite of being stingy with intros — instead he always finds small bits of time and ways to be helpful even when he can’t engage fully.

The book has too much insight to summarize in a post and these are just a snippet, so I encourage you to read it! Huge thank you to Brad for continuing to live by these values.

To illustrate this, let me lay out two very different ways of working very hard:

Scenario A: A CTO of a Series A startup mandates 996 for the engineering team, employees are told that the pace is to be in the office all of the time, always working at 100%+. They don’t make a case for why work so hard outside of that the company is very important and they will all do well if the company succeeds. The employees work around the clock on their jobs and the company grows.

Scenario B: A CTO of a Series A startup mandates normal working, with the exception of certain red-team sprints for critical work-streams that must be completed in order for the company to succeed - employees on those work-streams (which are time-boxed to projects with clear impact) are told that they must deliver these projects at all costs, regardless of hours.

There are pros and cons to both approaches, but which works better depends on how you define output.

Scenario A is better if you define output as

output = raw work completed over time

Scenario B is better if you define output as:

output = impact of the work x effort put into the work

I tend to be much more aligned with Scenario B, it’s not usually politically correct (within a workplace) to say that some work is more important that others, but it’s true! Certain projects, initiatives, and efforts have much higher impact and no employee was built to work on the highest impact thing all of the time. The same employee can spend their effort answering 100 emails or they can have a single call, well prepared, that closes a partnership that doubles the revenue of the company. Not all work is made equal!

I believe that the true model for what work matters is much closer to Scenario B, which requires hiring talented and self-directed employees that understand which work is important as much as how and when to work hard. This never excludes a 996 mentality for work, but most often it necessitates a pattern for employees that oscillates between sprints and jogging, so that when you decide you need to sprint you aren’t already winded.

Startups (and companies generally) are a marathon, where every once and a while you’ll need to sprint up 10 flights of stairs to deliver a single high-impact initiative, deal, or project. It took me a while to learn, but there’s a lot of wisdom in not forcing your team to sprint all of the time. Instead time markets, strategies, and important initiatives around your pace.

Over the past few weeks, I’ve been reading a book by the founder of Blackstone that has been on my bookshelf for a long time.

Last year, I was doing some work in that area generally, and it got me very interested in how the structure of private equity works versus something like venture capital investments, which I’m most familiar with. I really enjoyed a lot of the work. Still, I always found the business of private equity really interesting, and Blackstone is widely considered one of the best to ever do it. So, I bought this book intending to read it back then, but I finally got around to it now.

The premise of the book is basically an autobiography by the founder, covering everything from starting Blackstone to his early career and all the other things he did in life. What I really liked about it is its flow. You get to hear all the major stories, which include really interesting components of the 2008 financial crisis and how they built the business. But then, sprinkled throughout the book, is a series of principles and guidelines for how to work and live.

What I thought was very interesting about that is how, in our current business environment, there is so much movement toward taking shortcuts, making deals that may not always be the best deals, or playing people on deals. But the founder of Blackstone, which is the most successful private equity firm in the world, focuses most of what he talks about on integrity. He admits quite a lot when he is wrong and is able to carry those lessons forward into the functioning of his business. This approach built a reputation for them that has lasted generationally.

It reminds me a lot of the first firm I worked for in college, where the founder had a very similar mindset: reputation was always the foundation of their business. I think that is true for many financial firms.

Strategically, I also thought a lot of the things discussed were quite interesting, including how the financing and deals got done. He is incredibly honest about how every deal is basically a crisis, one where time and all of the details matter extremely highly. It was also fascinating to see how narrow of a margin some of these deals would close by, including the Blackstone IPO, which happened just days before the 2008 financial crisis kicked off.

I want to do more writing about the books I read because I think the insights can be good for other people, especially other entrepreneurs who are building things in areas like fintech. I’ve already recommended this one to a couple of friends who work in that space.

Amazon link

I’ve written on this blog before about my journey with sobriety (and many posts are subtly sobriety adjacent), but I thought it was worth reflecting a bit on the past year of complete, continuous sobriety and how that experience has changed me. I say “continuous“ because of how committed to absolute honesty I am - it would be easy to say I was “sober“ since over a year and a half ago, but it wouldn’t be honest to the slip up I had last June. This is the longest period of sobriety I’ve had since I was a teenager, and I’m extremely happy to have gotten here and grateful for the friends and family who supported me.

As I was thinking about what I’d want to write about, the main topic that came to mind was what it’s like now. If you last interacted with the old me, now close to more than two years ago before I started this journey, you might have had a very different experience than interacting with the current me now. I’ve even spent a lot of time correcting certain attitudes and motives with many folks from my drinking days with the people I was closest with. This has given me a lot of peace in life, confidence in being myself without any mind altering substances, and a foundation that has built many long standing friendships and relationships. I actually don’t want to shut the door on those experiences because the act of showing up differently going forward has built more depth with the people I care about most (in most cases).

That’s something I’m very proud of because it means that my actions today are an opportunity for the current me to correct any mis-attitudes that the old me might have had (which of course wasn’t ever always all bad, but there were some threads that needed correcting).

On an emotional level, I’m extremely grateful because without the filter of mind altering substances I constantly feel grounded. This is especially important during times of high stress or uncertainty. Over the last year life hasn’t been perfectly “happy“ and I’ve realized I don’t even want things to always be amazing. It’s such a blessing to be able to lose people you love and actually show up in a way that is supportive for family or deal with difficult or intense situations with generally more grace, forgiveness, or understanding. These things happen all the time, but how you deal with them is make or break. No one is perfect, but with a sober foundation I have confidence that I can face the hard stuff and come up with the right solutions. It’s not about always winning but about handling the losses in the right ways, not carrying resentments, and having a little faith that maybe it was all for a reason.

As I get deeper into sobriety, I’ve learned too about how my desire to drink was an escape from some emotion that I didn’t want to be feeling. I think the world builds so much stigma about alcohol but I did it with many other things too. At one point a whole pot of coffee before 2pm was a regular thing just to change the feelings that I was feeling about my first company - no wonder I could sometimes get anxious!

The shift towards experiencing these emotions instead of avoiding them though not only made me stop those behaviors but also helped me show up better and really understand myself. I’d recommend this to anyone regardless of how they identify. It increased my quality of life 10x both because of how much better directed my actions are but also because when you focus on feeling those feelings all of a sudden they don’t feel so immediately intense. I know so many people who do this with every other form of coping. Once you solve that root issue though, the desire goes away and it’s amazing. I would encourage anyone who’s thinking about making a change like this to double down and do it.

Why am I writing about it? It’s been something that everyone important in my life knows about, and although I’m aware of the downsides being public, I’m proud of that fact. It’s also become an opportunity for people who I might know to see an example of someone where this works where so much of the world “works” a different way. In a few lucky cases I know that’s been enough for people I know to make a change in their lives and I think the reward of helping other people make that jump is enough to justify any downside.

I hope I never have to re-own resetting this timeline, but even if I do the lessons carry in so many valuable ways. Here’s to another year!

I got into a deep dive and spent a whole afternoon, about six hours, building out this website. It was really impressive. I was able to integrate Stripe, authentication, and all the AI models needed very, very quickly, and get it all deployed. It was super exciting, and I was super grateful to have had the opportunity to do that.

The Classic Mistake

Later that week, though, I looked at what tattoo artists think of AI models in tattoo art. What is funny is that there is so much more a tattoo artist does to convince a person, or to help them iterate towards the idea they would actually want on their skin for their entire life.

What I realized was that, even though I had an idea for a product, I made a very classic mistake. I didn’t really fully understand what the customer wanted or needed, and I wasn’t sitting in the shoes of the customer. As a customer who goes to a tattoo shop, I want the person to help me figure out and validate that what I want is a good or fun idea, help me iterate on the art, and then add it in a way that is a good experience. AI doesn’t necessarily help you do that.

In terms of building something someone actually wants, you would actually probably be much better off creating a website that allows tattoo artists to better manage their inbound via Instagram, rather than creating an AI tattoo generator.

The Chutes and Ladders of Startups

This brings me to what I sort of call the chutes and ladders of startups. You can spend so much time iterating on the wrong idea and concept if you don’t truly understand the end customer or the dynamics of a market. Actually, it is the understanding that predicates any sort of success, because that understanding of the customer and of the market itself is what allows you to create the strategy that will then be successful.

Of course, you also need a bunch of execution, and I kind of bucket insight into execution. But it is actually about having the emotional maturity not to immediately jump to a market problem or get too caught up in excitement. While that excitement can feel good in the moment, it can be intellectually dishonest and lack the insight required to actually go and build the right product for the customer.

The Danger of the Rabbit Hole: Excitement without insight can take you down rabbit holes that will effectively make you spend years working on things that don’t really matter. It can also make you try to take cheat codes that you think are cheat codes, but really are things that have been tried and are not loopholes. Instead, they are holes you can fall into and never come back out of when you’re navigating startup dilemmas.

On the other hand, at times you can find insights that are true hacks in the world that no one else has really found because you are the first person to really think of it and be able to execute on it. Those things can take you much, much further as a result too.

Insight Over Execution

My tattoo shop idea is a very simplified version of this, but this exists at scale for everything in startups. It is why insight is more valuable than most execution, even though there is sort of a trope that execution is what really matters.

You need to be able to build the product.

You need to be able to sell to the customers.

But more than that, you need to be able to understand what the customer and the market needs at a given point in time.

That, in and of itself, ends up being more of an art than a science, and it is one that is extremely, extremely, extremely rare in a person, and hard to replicate.

I had the eulogy I gave for him written down and stored away. It’s definitely emotionally loaded, but has a good message about integrity and I thought it was worth sharing here eventually.

Here it is for anyone to check out, enjoy!

Hey everyone. Over the past few days I’ve heard many great things about my grandfather and I’m grateful for all of the folks and family that came to celebrate his life. In many cases you knew him longer than I did. Many have shared fond memories, kind actions, and celebration of who he was. I’m thankful for my mom, aunts and uncle for giving me an opportunity to talk about him and I wanted to use the time I have to talk about what I’m most grateful for my grandfather for in life. For me, there were countless fishing trips, pontoon trips on the river, and soccer tournaments as a kid, but more than that my Grandfather was one of the strongest role models in my life. Before I talk about that, first, I wanted to by reading the prayer of Saint Francis of Assisi because to me it’s reminds me of many moments with my grandfather:

Prayer of Saint Francis of Assisi

Lord, make me an instrument of your peace

That where there is hatred, I may bring love.

That where there is wrong, I may bring the spirit of forgiveness.

That where there is discord, I may bring harmony.

That where there is error, I may bring truth.

That where there is doubt, I may bring faith.

That where there is despair, I may bring hope.

That where there are shadows, I may bring light.

That where there is sadness, I may bring joy.

Lord, grant that I may seek rather to comfort, than to be comforted.

To understand, than to be understood.

To love, than to be loved.

For it is by self-forgetting that one finds.

It is by forgiving that one is forgiven.

It is by dying that one awakens to Eternal Life.

When I was reflecting on what I was most grateful for from my grandfather, the thing that kept coming to mind wasn’t a specific moment or memory. It’s a lesson, but it wasn’t one he explicitly taught me. He never sat me down and gave me some big lecture as a kid saying “this is the way to do it!”. Instead I learned it by watching him, listening carefully, and then thinking to myself “that’s the kind of person I want to be too.”

It’s a lesson about integrity and character.

The definition of character is how people perceive your moral actions. It’s a sort of social currency based on reputation. When people say “he has good character” what they mean is that that person acts in a way that is morally good when other people are paying attention. It’s important, but not the core, to living a successful and happy life. You can have good external character by taking actions that people admire and respect but still fall short in other moments. There are many people out there in the world who want to be perceived as having good character just because they want to be liked by others.

Integrity, on the other hand, is what you do when other people aren’t watching. It can lead to good character, but whereas character is an external perception by other people, integrity is internal and core to who you are.

Integrity is service that puts others before yourself, not because it makes others like you, but purely because it’s the right thing to do. Integrity is having the humility to say “I don’t know, but let’s figure it out” and the courage to face your mistakes and ask “how do I make this right?” Integrity is leading with understanding instead of self-centerness in situations where it isn’t expected of you. It’s the strength to face your flaws and course correct for the benefit of other people in your life. Integrity is about patience and faith that things will work out, even when that is far from certain. It’s a way of living without fear but with a sense of bravery about the unknown and stewardship for the future. Having strong integrity means spending your life creating much more value than you retain, taking less credit, and defaulting to faith when things are uncertain or hard. You can’t force someone to have good integrity or teach it to kids. It’s something they choose on their own after seeing examples of it.

My grandfather had some of the strongest integrity of anyone I know and it reflected in the way people knew his character. What made my grandfather so special is that he had such strong integrity that he was able to show up and face his greatest fears instead of backing away.

The example of this that stood out the most to me was from around the time my grandmother passed, when I came back to see her one last time about a month before she died.

Some of you might not know this but my grandmother passed away last year from late-stage Alzheimer’s. My grandparents knew each other since they were young children, and after 70+ years together my grandmother started to get sick and my grandfather became her caregiver for basic things. It was a big flip in roles. He was an old-school family practice doctor and did everything he could to help her, knew exactly what was happening, all the way to the end. In those moments he made a conscious decision to be there for the person he loved most in this world.

I’m sure he had a lot of fear. Anyone would.

Those last few weeks, after years of disease, she was scared and confused. People with late-stage Alzheimer’s start to lose a lot of sense of themselves and it’s quite scary. Instead of giving into his fear too, my grandfather did everything in his power to do right by her. He held her hand. He would help feed her her favorite foods and get her up and around family at dinner. At night he would pull their hospital beds together so she would feel safe. He worked with the caregivers to make sure she wasn’t in pain. To the very end, she was his partner and he loved her more than anything. When she finally passed, he was there all the way through.

People appreciated his actions, but no one was there to give him some big award. He just did it because it was the right thing to do to honor the person he had spent his life with.

Seeing my grandfather do that showed me that I could have the courage to face my greatest fears too, and helped hammer that lesson home in a way that nothing else could.

No one is born this way. We’re all born with our own imperfections and flaws and will keep making mistakes, big and small, as long as we are alive. It’s part of being human. At some point in our lives, everyone is faced with a choice to put others before ourselves, and not everyone chooses the path of service that my grandfather took. It came through in many ways that people are talking about him today. Throughout his life, my grandfather made a conscious decision to stand up for what was right, take ownership, put in the work even when it isn’t easy, extend a helping hand to those who need it the most, and in the hardest possible moments over many, many years choose that love and service for others over his own desire for his own comfort. That’s the integrity he had which was so core to who he was.

Grandpa, as we say goodbye one last time I wanted to say thank you for all of the good times and being a role model that I could look up too. I wouldn’t have learned that lesson without you. It leaves me with pride for where I came from and a sense of responsibility to make that same choice to deal more kindly with one another and live that good life you showed me.

I think when I was a teenage and into young adulthood I had the equivalent of this sort of delusion. There’s something admirable in “saving the world“ so to speak and to have the ability to “fix“ the worlds problems. It’s pervasive in technology and Silicon Valley to the point where it’s become a meme.

The main problem with this way of thinking is that the delusion is that it’s “up to us“ to somehow fix things. It is seeded on a belief that we are the one’s in control, that there is no God or higher power in the universe, and in the limit *yourself* must be the one to fix the problems in the world. That’s ego in a nutshell, something trying to convince you that you’re the center of the universe. Many ambitious young men believe that they will be the ones to be at the center of it all just like me.

Of all the ways for ego to manifest, I think that this ambition is both one of the most well intentioned but also the most dangerous. I’ve seen it lead people down a path where they see themselves be the fixer long enough that eventually they become the problem.

Two years ago I started to form a belief in something higher, and with this my self-centered model of the world changed dramatically. It’s my responsibility to play a part, but I will never be the orchestrator. These are God’s projects, and at his direction, my hands get to work on them. God will make it work with or without me and I can rest easy on that, but while I am being given the grace to work on these endeavors I will happily take it because it gives me meaning. I’ll take his suggestions as best I can and keep building. It’s what I was built to do.

I call this mind shift alignment. The ability to look at thing things in my life, good and bad, and act in service to something higher even if I don’t quite understand that today. My intuition, experience, and even odd coincidences can help guide me there, and the result is better than anything I could have done on my own. It’s my part to play. There are other projects that aren’t companies too - relationships, family, friends where every single day I’m given this crazy blessing to have the opportunity to show up and do what’s right. I wouldn’t give anything for that and pray I never forget it what a gift that can be.

If prayer is you talking to God, then intuition is God talking to you.

The more I’ve gotten these God shot intuitive moments the less I attribute them to “me“ and more to some higher outside force that acts as a guide. I think for a while I used to like to take credit, but really this was just my ego taking credit for things it didn’t understand.

When I’m making my “own” decisions, I tend to be brought down the wrong path, have the wrong timing, and fail to consider every option. When I’m making decisions from my intuition or “gut” as most people call it, then I rarely (never) make missteps and am often executing at my peak. When building anything (companies, relationships etc) the biggest barrier is lost time—not money or resources. Intuition acts as a shortcut that helps you make the right decisions at the right times to make the right calls.

When you discover this, it becomes imperative that you’re always making decisions from the position of your intuition instead of your rational mind. My mind has trained me that it is most likely wrong, whereas my intuition is almost always right.

The Impact of Feelings and Emotions

I used to not like certain emotions. I thought I wanted to be “happy“ or in some way more free. More recently though I’ve started to think about emotions as “raw intuition“ that hasn’t been fully processed. Most often, when I process those emotions, at the end I find myself receiving some form of intuition that ends up benefits me, helps me solve some previously unsolvable situation, and helps me avoid the pitfalls that would take more time or be exhausting.

For a long time I didn’t think I wanted to feel fear, sadness, or disappointment. The truth is that these serve me quite well! The problem is when I avoid them and let them fester because it delays getting to the right action that comes at the end of letting that intuition be fully formed.

It’s actually great to have fear or anxiety, it means you’re on your way to getting the piece of intuition you need to move beyond that problem. Where things get sticky are when you avoid or deflect and try to not feel that feeling. Often times avoiding it leads me to taking some defective or self serving action. The point is to feel the feelings to help you get to clarity! The more you lean into feeling it and understanding it the sooner you can get to a resulting correct action.

I spent a long time in life trying to not feel feelings rather than understand them, strongly to my detriment. This is understandable! Especially in critical situations these feelings can be overwhelming. The best way to work with feelings is to note them, get curious, and process them thoroughly so you can find those intuitive decisions at the end of the tunnel.

Reactions and Responses

When I first started working on companies, I would have emotional reactions to everything. Some concrete examples of things that are emotionally reactive:

• Firing an underperforming employee before finishing a PIP

• Lashing out at a lead investor for saying that we should have raised at a higher valuation

• Firing a cofounder for being on Twitter too much

In these moments where emotion meets rationality, it is easy to make the wrong decision with the right inputs. This is reactivity. The same feelings though when processed can become a superpower. When you’re afraid of that employee impacting the team, that investor not having the company’s best interest at heart impacting a board, or the cofounder’s ego getting in the way

Sometimes these might be the right actions but the wrong reactions that led to them. There are valid reasons for responding differently:

• Firing the employee can be the right decision, but it’s also important to send the right message to the rest of the team

• Flagging that investor might not have the companies best interest at heart

• Resetting team culture to be low ego and high ownership

Conclusion

Intuition or gut based decision making is a superpower when it comes to building companies and many things in life. There’s a key to working with it that requires you to love and lean into feelings with curiosity rather than aversion or fear. The end result too is not running from feelings like I was but actually using them as leverage and tools to level up how you make decisions and navigate the world.

It feels like every day I see new launches around speculative / crypto driven businesses. I don’t think any of these things are inherently bad - speculation should be legal but I think the industry as a whole is missing tons of guardrails when it comes to marketing what these products truly are to retail investors. Every time I see it, it makes me angry.

The way that these products are being marketed masks the risk to retail investors who do not understand the way that proprietary trading and marketing making works in sophisticated markets. I believe these investors should be allowed to trade in these markets by virtue of freedom, but I don’t think the companies that are winning deserve the right to mask the risk or who they are trading against.

The thing that makes me the most frustrated is because the marketing and dealmaking rules aren’t clear it disadvantages the entrepreneurs trying to do things fairly - it’s impossible to win by playing fair in these markets against large companies that are being sleezy by masking the risk, creating social media hype that doesn’t disclose the way the markets work, and only catering to a small set of professional traders rather than every day users. I’ve lived the reality of competing with cheaters directly and it pisses me off that the cheating is still ongoing. By principle, when I was working in crypto I never did influencer or prop trading deals or traded meaningfully myself. We just let markets play out naturally. It’s disgusting and not something I want to be around. I’m embarrassed I was ever associated with the industry, and embarrassed for some former colleagues for engaging and profiting off of it.

We need better laws.

/endrant

Great song with a good message.

The mere-exposure effect is a psychologicalphenomenon by which people tend to develop a liking or disliking for things merely because they are familiar with them. In social psychology, this effect is sometimes called the familiarity principle. The effect has been demonstrated with many kinds of things, including words, Chinese characters, paintings, pictures of faces, geometric figures, and sounds.^[1] In studies of interpersonal attraction, the more often people see a person, the more pleasing and likeable they find that person.

One core question to digital media: are you reading from the algorithm or is the algorithm writing you?

Just how there might not be “democrats” and “republicans” but instead “cnn viewers / NYT elites” and “Fox News viewers” there might actually be splits in belief based on if you’re a “instagram user” or “TikTok user”

Good food for thought :) .

I think there is this really interesting distinction that most people who work in software don’t quite grasp. There is a sharp difference between a “startup” and just a “business.”

The Startup Delusion

A startup is a business, sure, but it’s a very specific breed. It’s designed to grow extremely fast and capture a massive market. Because of that, these things are super risky. They’re driven mostly by hype and narratives, especially at the very beginning. To be honest, they’re very, very difficult.

When you’re launching a startup, you almost have to be delusionally insane. You have to believe you can capture such a significant part of a market that the risk becomes worth it for the investors, the employees, and yourself. I’ve done a few of these now. In the shortest, most simple way to put it: I’m just sick of trying to be that delusional again.

Trading Hype for Reality

I don’t think I have another startup left in me, and I told my friends that over lunch. Instead, I’d rather go build normal businesses that make money from day one. I like the idea of a model where you can put money into R&D, but you actually know what the investment is and what the ROI looks like. You understand those pieces of risk much better upfront.

There’s still a spectrum of risk, of course. I still want to work on software businesses and similar projects. But the interesting thing about a standard business is that you don’t have those same crushed timelines and wild growth expectations hanging over your head.

Focus and Fulfillment

Without those pressures, you just get to focus on building the thing. You have a much higher hit rate. It’s a lot more fun, and you can still make a lot of money. Plenty of medium-sized business owners make a great living building things that are good for the world and provide solid employment.

You don’t need to do it the way the Silicon Valley ecosystem pushes. I think people get lost in the sauce of the ego trip that startups provide. There is so much external validation involved, but after doing this a few times, I’m just tired of that. I’m more excited about the reality of actually building good software.

The point of all this is to say that I think I’m done with starting startups for a very long time. I still love to build, and I’m excited to find people to build businesses with over my life, but I’m ready to gear my life toward something a bit more grounded.

This year, I set out with five specific targets:

1. Double down on Foundation.

2. Find time for mentorship, teaching, and reading every week.

3. Bootstrap one thing to $10,000 MRR.

4. Find a girlfriend.

5. Make friends at the top of my social stack rank.

Here is where things stand.

The Foundation

On the foundation side, I think I’ve done quite well. I’ve been super consistent with the gym, meditation, and prayer. Most importantly, I’ve been keeping my mind in a really good spot. Honestly, I feel better than I ever have. There is this specific sense of peace in my life right now, and it’s great to finally be in that headspace.

Mentorship, Teaching, and Reading

I haven’t been doing this one super well. I have found decent windows for mentoring, especially through various work projects and writing here on the blog, but the reading side has slipped. I haven’t really finished any major books since January. I’d like to reset that and get back into a better rhythm over the coming months.

The $10k MRR Goal

I haven’t successfully hit this or even really structured my time toward it yet. I think Wrench Desk could potentially get there, but with how my life is set up right now, the sales cycles are just really difficult to manage. Because of that, I’m thinking about going back to the drawing board. I want to spend the next month or two hacking on a few other ideas to see what might have better legs.

Relationships and Social

The girlfriend goal is still a work in progress. That one is pretty self-explanatory.

As for making friends at the top of my social stack rank, this has definitely happened. Even with a bunch of changes at work making it harder to spend as much time as I’d like with people, I’ve made my friendships a huge priority. I’m incredibly grateful for everyone who is in my life right now.

Overall, it’s a mixed bag, but that’s exactly why I do these check-ins. It’s time to double down on the reading and get back to hacking. Thanks for following along.

Most people don’t understand cybersecurity all that well. The reality is that anything out there can be hacked. It’s ultimately just a matter of cost. The best defense isn’t about being unhackable. It’s about making it extremely expensive to access certain systems. When you look at the various layers of security, the certifications, and the different postures companies adopt, that’s what it’s really about: How expensive and difficult are we making it to breach this system?

In the short term, these new models change that equation for everyone. But in the long term, I believe they’ll change it so that breaching the most secure systems becomes significantly more expensive.

The reason is that these models enable automated pen-testing frameworks. If you own your own code, you can have these models audit it as part of your continuous integration and testing. We can catch bugs before they ever ship.

We’re seeing a surge in bugs being found right now, and I’m not sure it’s because the world suddenly became less secure. It’s more likely that people have finally discovered how good these models are at finding existing vulnerabilities. Look at what happened with Firefox: their reports for critical vulnerabilities were fairly low, in the tens, for the last five years. Then, over the last two months, that number picked up significantly, and they fixed over 1,000 in just the last month.

To me, that isn’t a statement on the world getting more dangerous; it’s a statement on how insecure the world already was and a sign of where we’re headed.

I’m actually really excited about these automated testing strategies. We might have a temporary period of turbulence as we adjust, but I think we’ll eventually settle into a new equilibrium where things are much more secure than they used to be. There are incredible opportunities right now for building automated pen-testing into almost every digital surface that exists.

As always, the most vulnerable surface will remain the human layer. Hacks are so often the result of someone being exploited, tricked, or targeted because they were being trusting. It warrants a certain level of paranoia, but for me, this shift is much more exciting than it is scary.

One thing I became obsessed with when I realized this is what I call a “key habit.” This is a habit that, when you do it, causes your other positive habits to happen almost automatically. I spent a long time searching for this a decade ago, before eventually going on a “walkabout” through other areas of life that I’ve written about here.

Recently, I’ve come back to that idea: maybe there really is one key habit for me. One thing that, when I do it every day, compounds into everything else so I can do what is important and good without as much friction or thought.

The Headspace That Changes Everything

If I boil it all down, the most important habit I have is this: every morning, I get on my knees and say a prayer. A lot of that prayer comes down to:

• Making myself more humble.

• Allowing myself to get out of my own head.

• Thinking about other people rather than just myself.

• Practicing gratitude.

Starting the day from that headspace is what makes the other pieces of my life fall into place. As a result, I show up better for the people in my life. I tend to go to the gym. I tend to eat right, avoid alcohol, and maintain all those other small things that add up to be very big things. It fundamentally changes how I live and how I appear to the world.

Heart Space Over Urgency

This habit has been working for me for a little over a year now. What I’ve realized is that many of the things I thought I “had” to do don’t actually require such urgency.

What I do need is to find myself in that right space, approaching life from a higher degree of thinking. It isn’t just about following steps; it’s about getting myself into the right head and heart space so I can show up the right way every single day.

The Limits of “What” vs. the Power of “Why”

Current models are incredibly good at writing lines of code and describing exactly what those lines do. However, they struggle—and often fail—to answer the fundamental questions of the user experience:

• How is this going to make the user feel?

• What is actually useful to the person on the other side of the screen?

• What parts of this interface will be frustrating, broken, or otherwise undesirable?

There is something I can tell a model that it can’t quite grasp itself. I can provide the instructions for what to do, but behind those instructions, there is the why of what to do. In many ways, this bridges my heart and my head in terms of what actually matters for the customer of whatever software we’re building.

Why This is a Risk for Vibe Coding

One of the things that makes me a little bearish, frankly, on the vibe coding concept is that the skill of understanding human impact is one that takes a long time to build. It’s a skill I’ve only ever seen humans truly possess. While I’ve seen the models get a little bit better at guessing what a specific use case might look like, they are definitely nowhere near getting the full thing done.

Furthermore, these advancements don’t actually necessarily speed me up as a developer anymore. I think the biggest speed increase I got was when GPT-4 came out. It could knock out almost perfect code; I could provide a few files, give specific instructions, and it would write the code pretty much bug-free as long as I was descriptive enough about exactly what I was asking it to write.

Today’s models are basically that, except with agentic harnesses; they are better at exploring codebases and understanding where to make changes, so I can be a little less specific in my descriptions. But the thing I’ve realized is that if I don’t understand how the product works myself anyways, I have a really hard time actually creating the experience that is necessary for end users.

The Plateau of Usefulness

I don’t know exactly where we go from here, but my intuition is that the models themselves are starting to slow down in terms of their usefulness, especially to engineers. They might still be quite useful to many other disciplines going forward, especially as other people ramp up on them.

I’m not saying Twitter is inherently bad, but the way it’s structured today is definitely a problem. The algorithm is built to reward attention-seeking behavior rather than reality-seeking behavior. It turns out that the things that get the most attention are often the least real, and the systems we have in place, like Community Notes, are just completely insufficient for telling the truth.

Marketing vs. Merit

You end up with this huge bucket of consumers who believe whatever is happening on their feed. This forces companies to be extremely reactive because the Twitter zeitgeist can actually move the needle.

A perfect example of this is the debate between Claude and OpenAI’s Codex. If you talk to programmers who use both, most will tell you that Codex is the better product. But because the Anthropic team was able to manufacture this super viral loop on X, it almost destroyed the concept that the best product wins. Maybe the best product wins in the long term, but in the short term, the best-marketed product is winning. I don’t think that’s actually good for the world.

The Viral Loop Problem

The way people have figured out how to “hack” these algorithms for viral marketing moments isn’t a great mode for building products. It damages the world way more than we realize. On some platforms, maybe a viral loop is fine, but if Twitter is supposed to be our digital town square, we need a correct way of moderating which voices are heard. We need to know that those voices are being truthful.

The Reality of Groupthink

I don’t think it’s been all bad, and I think Elon actually has good intentions for the platform. But it’s become so political that everything has just averaged out to groupthink. Whether it’s on the left or the right, these algorithms pump narratives at us that are really hard to distinguish from reality.

In the long term, that’s just not good for society. It leads me back to the same conclusion: this is exactly why we need to regulate social media. We can’t keep letting the loudest, most viral voice dictate the reality of our businesses and our lives.