A new friend told me she did not like Los Angeles. She could not walk around the city and not feel haunted by the dreams unfulfilled.

I don’t spend a ton of time in LA. Recently, I went to a first house party in the city. Hosted by a director who had seemingly made it with a nice house in the hills. While his 35% rotten tomatoes on his big film may bely the achievement, his proud wifi password bearing the film’s name shows his deserved excitement.

Most girls who I speak with tell me they are actresses. One had been in a film of the director. Another hoped to be in one soon. They spoke with a quiet demeanor. Almost ashamed until they had fulfilled their dreams.

One house party in LA is more than I’ve been to in San Fransisco. Four years of college, four years of the startup, and many overheard meetings in the Blue Bottle at South Park later, I do feel I’ve lived the culture and dreams of that city many times over. Everyone is applying to YC. Everyone believes against all odds they are building a unicorn.

You hear the confidence. Perhaps we take it for granted.

I have a good friend who has raised a ton of venture money. But he’s worried about what is next for his company. “What if I fail?” he asks me. “You’ve already won” I reply.

Another friend last year went through a slog of a raise I feel terribly. He’s so brilliant and kind. I remind him his ability is not tied to the specific outcome, but the ability to make massive outcomes even possible.

In tech, the counterfactuals we become haunted by are the dreams we felt taken away too soon.

In LA, it seems folks are tortured by what they’ll never feel a right to dream to begin with.

It is strange what a different conversation I have with folks in the different towns. I feel more comfortable trying to prove to my friends in tech that they were in fact successful. Perhaps because it is regurgitating the words others tell me when I am worried. When I believe I am going to fail. When those words will fall on my deaf ears.

On Sunset Boulevard in Hollywood, I think of my favorite Avicii song, Sunset Jesus. The first verse goes

California Don’t let me down Seems so golden But there’s struggle all around

I see it in the eyes. I know what it means to fear your dreams are evaporating. I don’t know how it feels to worry you’ll never get the role to start it.

The second verse continues

Staring at the billboard from the bus Looking at the faces Thinking “That could be any one of us” So give me hope, give me hope

I smile reading the lyrics. I describe my first favorite book in life, The Shadow of the Wind, as a love letter to hope. It is no surprise my favorite song could bear the same descriptor. The first line always hits me. Landing in SFO and driving to the city, you see the billboards of every new tech company litter the highway.

You’re a customer of some. Your friend works at another. It could be you.

LA has “For Your Consideration” billboards around awards season. They seem foreign to me. I’m obviously not in the scene. But they seem so unattainable. The same folks every year, no?

The song’s chorus reasons

My dreams are made of gold My heart’s been broken I’m down along the road, but I know My dreams keep fading ‘til I get old

At the final crescendo, there are about 30 seconds of pure euphoric melody. A happy build up to the final drop. A contrast to the lyrics dashed with melancholy. At school, I’d close my eyes during this part. I’d replay the moments in my life that had lead me there.

The inevitable story of my dreams.

Hope was obvious. Hope was my currency. My dreams were there, and I was chasing them linearly.

Perhaps the moral here is I need more friends in Hollywood to fact check my philosophy. My offered sympathy for their community.

I once asked my therapist if it mattered to him that he could never verify if what I told him was indeed factual. He told me the veracity of the claims did not particularly matter. What he paid attention to was what I believed was true. How I told my stories. What closure I longed for.

I feel that way in LA. I like to travel because you feel a stranger. Perhaps that is being in LA for a weekend. With a kindred dreamer, yet a very different spirit.

I know nothing of LA. I don’t know if the city is haunted. I just know the dreams it holds are foreign to me.

I know I should be more grateful to have lived a life where dreams felt so real. Where my friends and I can write something down and see it get translated into the world the next day.

At the party, I asked someone what she thought about the concept of dreams. She lived in LA. She was starting a jewelry brand. Two weeks in.

She paused. My philosophy is usually an unusual turn for most. I appreciated her respect for the question.

“Dreams are real. They’re what we are in now”

She finally decided. With a tepid smile.

“Hope though. You can’t control what you hope for.”

I now paused. Her thoughts struck me.

In high school, I once made the debate team go through an exercise. “Convince me an elephant is purple,” I challenged the group.

My reasoning was simple. We have three root colors (red, yellow, blue). In some cultures in Siberia hundreds of years ago, they had two root colors. Grey could be purple in their eyes.

My whole life, dreams were dangerous. I never realized that. Because I was so intoxicated by their possibility. Perhaps they were the best escape. Sandcastles in the mind. But I loved them. And am grateful for them.

In the words of my other favorite book, The Night Circus, they possessed the potential to turn into nightmares. I see that with my friends. Who can’t be proud of all of they have done because the dreams that suddenly feel unfulfilled torment them.

But hope. Well we controlled hope. With a few lines of code. With the right meetings. Hope could unlock dreams. We had hope today—it gave us the ability to dream about tomorrow.

I don’t know if either me or the jewelry girl are right. I don’t think either of us are wrong. Like the purple elephant, we have our own system of beliefs.

I just find it so fascinating we can go through life with such different associations for such powerful constructs.

Perhaps LA is not haunted by the dreams it has not fulfilled.

Is it haunted instead by the dream it never had? Of the hope it’s people dared to feel?

Or does the sun shine so bright because everyone feels they’re already in their dreams?

SF is haunted by the dreams it almost had. That’s for sure.

It’s why I try to remind myself to be so grateful. We’re lucky to live a life where dreams seem so real and attainable. They may vanish. But they were real, even if just for a second. Few get to experience that.

And is that not the joy of life? To have something that we could feel so closely? More than a whisper.

The dreams hoped for. And the memories of the dreams lived.

“I think audiences get too comfortable and familiar in today’s movies. They believe everything they’re hearing and seeing.”

Christopher Nolan

I

This month, I watched two movies where purpose was obvious. In 2026 SciFi epic Project Hail Mary, Ryan Gosling’s character Grace (and his alien friend Rocky) has a very clear purpose: save humanity. In 2006 Oscar winning German Film The Lives of Others, Stasi agent Gerd Wiesler has a very clear purpose: help two people who will presumably never know he aided their lives. Both characters smile at the end of their films, having accomplished their missions.

II

I’ve long believed we play games with ourselves. I think for those without religion, our purpose is tied to the belief in those games. And our purpose evolves based on the games we play.

It’s not a video game. I don’t believe levels progress linearly. My analogy is closer to Inception. Purposeful ambiguity what the actual real level is. Confidence they’re different. Understanding that some conversations are only meant on certain levels.

Project Hail Mary is 150 minutes. Linearity is a feature—not a bug—of the medium. Grace’s purpose doesn’t waver because the film can’t let it waver. A two-hour narrative needs a through-line or it falls apart. Wiesler evolves in The Lives of Others, but on a track. The script knows where he’s going even when he doesn’t.

III

Movies are built for crowds. Netflix has become famous of late for ensuring the audience forgets no details, and has no blanks to fill in.

Movies are like art galleries. We browse, we connect, we reflect. Because we saw something by other, not because we saw ourselves in other.

Books, in contrast, are mirrors. I firmly believe that. Prose lets us project ourselves into the pages and see others perform our actions to feel the moments we have breathed.

Books wander. in The Art of Hearing Heartbeats, the purpose of the lead characters Mi Mi and Tin Win evolves to the reader. The duality is expressed perhaps best toward the end, when it is reflected “Not all truths are explicable…and not all explicable things are true”. Readers can feel the void of interpretation. Maybe two levels are here in my Inception analogy.

IV

In a way my writing contradicts itself due to this wandering of the levels of the game. To me it is consistent, just when taken non-chronologically. While returning to old levels or exploring depths of new ones, I feel a need to share and rectify.

It’s why I over think my writing. Why I have half a dozen unpublished essays for a Substack with little distribution.

It’s because I view most of my life as actions in the game. Achieving my purpose. Lapses in publishing still fall under a strategy bucket. I just can’t express those actions in the context of the game.

A focus of mine over the last year was to reflect less. I watched more movies. I enjoyed characters in a vacuum in their vacuum. It was an interesting level for me in the game. One that has ended over the last month or so. The game calls for each level to feel the final level while in it. And then to appreciate the next one all the same.

The games are repetitive if we look at them linearly. Like a movie. Which is why, despite the call for ones life to feel like a movie, we end up rejecting this notion. If it was obvious each time there would be no game. It is the pendulum knocking us to different parts of the game which reinvigorates the purpose of it all

.

I love winter. There, I said it. I promise this is not cope. I lived in California for four years, enjoyed Januaries of 65 degrees and sunny, and made the consensual decision to move back to the east coast.

I grew up in Philadelphia. February has always been a special month for me. Summer has always felt a bit weird.

In high school, February was the month Mock Trial and DECA got serious. My big competitions. States. It got dark early. There wasn’t much fomo. Fewer parties to not be invited to. In college, it was February 2020 where I wrote my first business plan for Footprint. It was February 2022 when we raised our seed round. And February 2024 when we did our Series A.

I joked that in a messed up mercantilist way, people got seasonal depression in winter and euphoria in the summer. Given that neither of these permeated my emotions, I chose to reclaim the narrative with my own path.

Summer to a younger Eli represented a time “others were ahead.” They were having fun. They were enjoying the moment.

I’m not proud of that. But it’s how I felt.

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Winter was a time I “was getting ahead”. Putting in the work to have fun many summers from now. Building the thing that would let me enjoy the moment many summers now.

Young Eli is easier to explain. He was keeping (imaginary) score. His goals were easy to explain. He was a bit petty and a bit more vengeful to those not keeping imaginary score.

As I’ve gotten older, I’ve stopped keeping score. As I got healthier, I also started enjoying the moment today.

But I still love winter. Maybe it’s because of the imperfection. The romantic notion of putting on a jacket and walking through the snow. Maybe it’s the flurries of nostalgia. I remember walking through NYC during past fundraises on cold nights. It feels right.

Or maybe it’s because I like the invitation to change. And then the ability to return. I think I wear a few masks. I still greet young Eli at times. Full of unrelenting ambition. Full of unimaginable confidence. Unable to consider a path where things won’t work out. Because I control that. And I simply would not let that happen, no longer how long it takes.

And I’ve also come to love summer. It was different. Uncomfortable at first. The calm. The permission to be present. A drink with a friend when the sun is still out at 8 PM. The splash of water. The humidity. There is something nice about everyone being happy. About everyone enjoying these months. knowing what awaits us a few months from now. Not letting that get in the way of the now, though.

And I greet Eli who lives in the moment. Who enjoys a meal with a friend on a weeknight as a fun luxury. Who knows happiness is not a milestone. Let alone a feeling that any milestone can bring. Happiness is the present. It’s small things. It’s universal.

I still appreciate winter. I’ve just come to understand why everyone loves summer. I wish young Eli appreciated summer more. And I bet it would do people more good to enjoy winter.

I used to want those mindsets to converge. I now think it’s best they’re left to their own devices. They come together in their own way. Because I can move between them with more haste than the seasons may change.

There is something I appreciate about being able to have those different places in my mind to travel.

Summer sunsets hit different because of the days it got dark at 5. I like seasons.

I made a long document in 2023 which no one really cared about. So Alex put it into GPT to create a Shakespearean language version of my doc. That doc was far more read (deservedly so). A snippet of that below (and yes it linked to a Suno version of the song).

In 2025, I used AI to help me create company values tied to the story of the first lunar landing. The slides were dense and really unnecessary.

So this year I kept it simple. The three values I try to embody. And the three values I try to look for in every recruit.

These are the values I try to embody. Or just naturally do. You won’t make it as a startup if you don’t believe. I in my deepest heart believe every prospect we speak to will eventually use our tools. If you don’t you won’t sell. And if you’re not ambitious you’re in the wrong game.

I’ve always loved learning. I have subjected the team to presentations about ports I found interesting (i’m sorry everyone) and tried to tie it back to identity. But I also think curiosity is key. Are you interested in learning about what our customers do? If you are, you’ll be a better seller. Are you curious about the latest AI tools for developrs? If you are, you’ll be a better engineer.

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Empathy is something I strive for. I am forever grateful for the team members who have joined. I care about them. The same goes for customers who have taken a chance on us. I want us to respond right away on Slack to customer questions. I truly believe you’re more likely to if you care about your customers on a human level (we maybe took this a step further than anyone by sharing an office with a customer for 18 months and counting :)). But it helps. I know how important our tool is to them. What would happen if it broke. Or if it hurt conversion. It wouldn’t just impact us, it would hurt their ability to scale.

You have to lead by example. We are not 9-9-6. But people know Alex and I are online pretty much all day. And people respond to us late into the night. Startups are tough. Hours are long. But it’s not pageantry. It’s the truth. We’ll never ask anyone to do something we won’t do today. I still send cold emails and prospect like SDRs. Alex did on-call Christmas week.

We also encourage folks to live their lives. That’s opaque, but we mean it. Take a 3 day weekend to go to a wedding. Leave the office at 6 to get dinner with your family. Human things. I don’t get SF culture around denying these small things. It’s important to me to tell people to take care of themselves. Nothing is worth sacrificing big moments and living quality.

As we grow, I’m trying to be a bit more purposeful. Planning team events with a better cadence (a huge shout out to the team for taking better initiative than I did on organizing happy hours and team lunches over the last year as we’ve grown). Creating new traditions.

But if I’ve learned anything, culture is not forced. It isn’t from coffee walks (though those are great!). It’s from being honest about what you represent and then hiring to match and build out the team of folks who have those traits.

Serve

Marty Supreme is a movie about ping pong. On paper at least. Their marketing motto is “Dream Big,” and no disrespect to the ping pong community, but I was unclear how these two ideas coalesced into the Oscar-buzzed A24 production. But boy they did.

At the end, in the culminating ping pong match, I found myself on the verge of tears as Marty found himself on the verge of match point.

I spent a lot of last year finding happiness and joy in the journey. And I am happy I did. I can now say that my earlier inference about happiness was wrong: happiness does not hinder your ability to dream. But at the same time, dreaming does not need to hinder your ability to reach happiness.

Because I’ve learned that dreaming is not just about the destination. One of my favorite poems is Ithaca. It tells the story of a ship setting sail to the port of, you guessed it, Ithaca. And it argues that regardless of whether the ship reaches Ithaca, that initial dream still dictated the ship’s journey. Even if you docked at a nearby port, you wouldn’t have gotten there if you didn’t set off on the journey in the first place.

Love yourself for setting off on the journey. That is what the poem is telling you. Winning is the journey.

But what happens when you get close to the port? When you can… see Ithaca?

Is that about the journey? In that moment. For a second. Nah. It can’t be. Good luck telling yourself that, all young and naive about to set sail. They might not be able to appreciate a journey, but they also know what you know deep down, too: winning is winning.

Return

How do you show the journey?

I struggle sometimes in trying to over connect the dots of my life into one cohesive narrative with one clear arc. Which has, of late, led to perhaps too many compromises in my writing. Because my life, like my beliefs, has the ability to change from what I initially intended. It’s not that I no longer believe what I believed as a kid. Starry eyed with unfettered ambition. It’s just that I also believe other things.

This summer, I wrote a really long essay about dreams and happiness. I privately shared it with a couple dozen folks. This fall, I wrote about my difficulty in reconciling multiple philosophies on life. In other words: must we have one philosophy which updates as canon, or can we have separate belief systems which may be contradictory?

So once again, how does this lead us to a movie proverbially about ping pong?

Because I found myself in a weird dilemma at the end. Timothée Chalamet’s character Marty had just spent two hours and 15 minutes fighting to get to his zenith. Clawing for a chance to win. And we, the audience, see him down 20-18 in a ping pong match to 21.

At first, I wanted the movie to end mid-match. Winning was not the final score. It was doing everything on earth to have a chance to play. Milestones don’t make us happy. There are always more milestones. It is the beauty of the journey. It is the relentless effort to play in the game. “To be the one who jumps,” as I wrote a few summers ago in Italy.

But then he tied up the score. 20-20. Fuck. After everything. All the setbacks. All the humiliation. All of the idiotic decisions. All the doubt. And endangerment of him and others.

Winning was the final score. Winning was winning. I had never been more invested in a ping pong match.

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Rally

The journey is slow. I’ve always been drawn to it. You just don’t realize when it is about to end. Timmy’s character didn’t realize until 10 minutes before this match that it was to be his match.

In the book Tomorrow, and Tomorrow, and Tomorrow there is a 40-page section towards the end which seems weird and incoherent. Until you realize they were one small part of the journey in one of the protagonists’ search for redemption. We needed to feel the pain and the slog to understand. It couldn’t be linear. The journey rarely coheres.

The match point does not negate the rally. We applaud the participants.

But the rally should not impact the gravity of match point.

Match Point

Yes, you should come to love the journey. If not, there will only be more meaningless milestones. There won’t be happiness. After the movie, I listened to an interview with director Josh Safdie. He called his work a heist movie. “A heist of fate”.

I fell in love with The Shadow of the Wind when I called it a “love letter to hope”. I badly wanted the protagonist Daniel Sempere to win. To win the girl. I needed that closure. For him. And for me. Yet in Supreme, as I said at the top, I wanted the screen to go black. I didn’t want to know the result. It’s not that I feared Marty losing. It’s that he was winning. In the moment. In the play.

Safdie said that “what grabs” him after Marty triumphs is “the hollowness on stage after he wins. He’s looking around and he’s lonely. To dream is very lonely.”

For yes, winning alone isn’t winning. I don’t disagree with what Safdie said. Maybe because I left out the middle of that quote. About how winning let him release to then win the bigger prize (to not spoil the entire movie, it is a family thing). His life was not complete for winning the moment.

But with all due respect to the director, I just didn’t see it that way. For in that one moment. Winning is winning. I need those two points.

I’ve come to view these two thoughts as independent forces. You can’t converge them into a defining thought. You must love the journey. You must not view happiness as a milestone. But at the same time. You have to run after winning for the biggest dopamine hit in the world. You have to dream big with reckless regard.

And then these two forces can illuminate each other. The journey. The pain and length of it lets you move to the second narrative. It lets you appreciate it.

Winning was not hollow for Marty. That dream alone was hollow. He sees that. But he needs to complete that dream--one way or another-- to process that. You should find those other areas sooner than later. Ideally before match point.

You should learn to love the journey.

The journey is what makes the moment possible.

But match point is match point.

A lot of people come to me when they want to start a company. I ask them why they want to start a company, they respond, and I proceed by asking them the real reason they want to start the company.

Let me be clear: the second answer does not negate the first. Both are true. But I believe it’s important to be honest with oneself. Because in order for you to fulfill the first answer, you’ll need to get to the root of the second. I often believe every story we start in life can only be finished once we settle the second story beneath it.

Let me also be clear: there is nothing wrong with the second answer. The truth doesn’t need to be morally approved by the pope, but it must be understood by you. There also may be better ways to achieve it than starting a company. Which is why being very honest about these questions before starting a company is an exercise worth your time.

Why am I so confident in this? Because I’ve yet to meet a founder who does not have two different answers. So I asked eight founders the below two questions:

1. Why did you say you started your company?

2. Why did you actually start your company?

This is a group of folks for whom I have tremendous respect. The 8 have raised over $500 M from top funds such as GC, a16z, Index, Coatue, First Round, Khosla, and QED.

They clearly all care about their products, their customers, and their team.

They also all care about money, respect, and freedom.

Their answers are below, untouched other than a few edits for typos and brevity.

Founder 1

1. I say I started my company because I love delighting my customers and shipping amazing product

2. I actually built my company to prove that I could do something bigger and better than my dad and my previous cofounder

Founder 2

1. I claim I started my company because I saw a deeply flawed financial system and was inspired to help the underserved gain financial independence.

2. The real reason I started my company is because I wanted the people I admired to respect me. I wanted the status of being a founder and to be invited to the table where decisions were being made.

Both can be true btw. I just think far too many founders are not honest with themselves about the “shadow reason” and delude themselves into thinking the stated reason is the real one which leads to burnout and existential dread.

Founder 3

1.⁠ ⁠Have the biggest possible impact

2.⁠ ⁠⁠Autonomy/flexibility (when I work, who I work with, what I work on). Not always the case in reality but I do believe it’s my biggest why (not wanting to respond to anyone else) + becoming financially independent as early on in life as possible (which is correlated to not responding to anyone else).

Founder 4

1. I say that I was so captured by the scale of the problem that I couldn’t walk away from it. It was so big an obvious that I just had to go after it.

2. I for sure have a deep insecurity about being irrelevant / not leaving any impact and I thought that starting a company (any company) would help me feel better about building towards that. I now realize that it was fairly flawed logic and that the irrelevance piece doesn’t matter as much as whether or not you care about the specific thing you’re trying to leave an impact on (irrespective of the scale of that impact).

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Founder 5

1. To create the world’s first credit building debit card that could help the millions of sub prime Americans who cannot get or do not want a credit card and build a good business at the same time.

2. To see if a quirky crew of consumer product outsiders could actually make a dent in the credit system by creating a more clever credit product that helps instead of hurts. After a few years in and having gotten pretty big, Experian made a bogus debit card that claimed to build your Experian credit score. We were flattered.

Founder 6

1. I said I started my company primarily because I wanted to make a positive impact in the world. That’s true for sure, but there’s some unsaid thing I think every founder actually has, which is a desire to prove to themselves and everyone else that they’re special

2. There’s also a big unsaid thing about like, of course I want to create financial freedom for myself and my family, and I’m also really motivated by doing that for all the people who took a bet on me (primarily early employees, but also angels, investors, etc.)

Eoghan McCabe talks about this in a way that resonates with me: Silicon Valley is really taboo about money, and nobody likes to talk about equity or their intent to create an enormous company and generate wealth, but of course that’s also a huge motivating factor for everyone. He said at Intercom he became more ~candidate~ candid about this over time (“hey I think if we hit our plan, we’ll be able to raise at a $2b valuation”), and that it was super motivating for the team and a thing they appreciated

Founder 7

1. This was an issue I cared deeply about. This was an idea I had spent two years working on. My life had led me to start and build this company. The opportunity was obvious.

2. I thought it would make me famous/rich which would let me meet/date the women I wanted. Which I thought would bring me happiness.

Founder 8

1. To feel a sense of purpose. My inputs are autonomy, impact, and curiosity: I need to bet on myself, solve a real problem that matters, and genuinely enjoy learning about the space. In the year after selling my last co and starting my new one, I got healthy and reflected (a lot). I took the destination off the table to solely focus on the journey, pursuing the same things but for practically opposite reasons. Autonomy provides an internal locus of control instead of feeding my ego, impact is measured one customer at a time instead of long term statistics, and curiosity means enjoying learning for its own sake instead of searching for the next piece of the puzzle.

2. My year gap between companies coincided with tech going red pill, and I let myself get negative and jaded. I watched the legendary founders I used to worship morph into narcissistic villains. Silicon valley has always stood for changing the world, but at some point stopped asking “would the world be better if this works”. The answer isn’t to stop progress in fear of the risks, nor is it to pursue progress no matter the risk. The right answer is to think through the potential negative outcomes, avoid the ones we can, and take responsibility for the mistakes and unexpected outcomes that inevitably come. I rediscovered my belief that most people are and want to be good, and this moment is just a moment when a small cohort of people are reaping the rewards at the peak of their success. Humanity’s greatest feature is that nothing lasts forever. The best is yet to come, and my dream of silicon valley is forever worth fighting for.

I was recently catching up with a friend. She just raised her seed round. She was asking about when they need their product out.

“It’s not existential. It’s been a month since the raise,” I say

“Isn’t every day existential?” she kindly replies

“No. “ I reply, more firmly than the conversation probably required.

As a founder, I think there are only a few true existential moments. The two biggest causes of company failure are running out of money and co-founder disputes.

Thus tier 1 of allowing to feel existential are:

• You’re down to final few months of funding

• You’re going through a co-founder break-up

Tier two look scary and could lead to tier 1 moments, but is not yet truly existential

• Your product isn’t resonating (early days)

  • If you have runway, you can pivot. Or change sales leadership

• Key account is churning

  • Once again, if the answer to above two are no, you have time to explain this away (we had to change X, we were getting undercut on price, etc.)

• Key employee departure

  • Don’t get me wrong. This one is tough. But, doesn’t signal company is going away tomorrow.

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Why does this classification system matter? There are two key reasons:

You work worse when you’re existential

When you feel existential, you think short term. You go into fight or flight. How do I salvage this? Which is the proper response in that moment. When literally one thing matters.

However, this type of thinking is bad if done for extended periods of time. To win with startups, you need to think long term. Not “how will I win today” but “how do I execute on a vision which will beat all of my competitors tomorrow”. You can’t do that if your cortisol is driving the bus.

Statistically your company will fail, so you might as well enjoy the time until then

I don’t mean this in a biting/negative way. It’s not sarcastic. And failure is a subjective term (my first Substack was encouraging people to fail more, and I said starting a company was one of the best ways to do it :)). I’ve been through what I’ll call tier 1.5 problems from my above chart. Derivative issues truly in between the two tiers. And each time, I had a thought:

I really wish I hadn’t spent the last few months stressed about things that weren’t actually life-or-death.

If it truly is the end, it’s a shame you’ll have never gotten to enjoy any part of the journey. And if you figure it out, there was perhaps no need to be so existentially stressed for so long :). And I really mean that. When you have moments of true, existential stress, it simply sucks. You feel it mentally. Physically. Everywhere. Don’t do that to yourself when you don’t need to.

Don’t confuse existential with aggression. I would argue you can work harder when you’re not worried. Stress takes up a lot of mental bandwidth. I am far more productive when I am not stressed. I’m able to work for longer durations without a break. Stress is truly killing you in many ways.

This isn’t just about building companies

I had a conversation with a family member the other week. About how much we have to be grateful for. The typical stuff one does around Thanksgiving. And it’s true. I’m healthy, my family is healthy, I have good friends, etc. I can list the platitudes we know. But I suppose it doesn’t hurt. Because sometimes I lose sight in them. Letting the stressors pile higher than they need to be.

Life is meant to be enjoyed. Stress will be there. It may be real. It may even be existential at time. And you’ll deal with it then. The eventual ephemerality of the lows will be looked back on, as strange as it sounds, with a strange smile. So keep them short. Don’t mourn in advance. Don’t linger on what’s in the past.

In the journey of building. And in life. Just keep in mind that most days are not existential. And that’s why they’re worth enjoying.

You don’t realize you’re burning out

My biggest advice on burnout is you do not realize when you’re burning out.

You don’t wake up one day to a push notification. Oura/Whoop are not that good.

You’ll likely instead do what I have done several times. And what I don’t recommend. You won’t take time off because “you don’t need to”. You’ll push through. And then one day, a stressful event will push you over the edge. And you’ll be a weird combination of numb and stuck.

You’ll go back to 50% productivity. A fight or flight mode to figure this new stressor out.

It is at this moment where you will want a vacation.

But it is too late for that. So instead, it is at this moment where you will wish you had taken a vacation.

I wish I had better advice on diagnosing when you’re in the process of burning out. I really don’t. My advice is to take a break before you feel you need to. It is the safest thing to do.

You’re asking the wrong question

The default question in tech has quietly become: What’s the most amount of work I can get done?

The natural answer is work from 9 AM to 9 PM six days a week (9-9-6). The fundamental issue for me with 9-9-6 is that I simply reject the premise it will lead to more productivity.

Because I’d measure productivity different I think the focus should be on: how do I produce the highest amount of high-quality work?

Anyone can work hard. Very few people consistently work great.

You probably don’t need a sabbatical. But plan things to look forward to.

A three-day weekend with a friend. Or—call me crazy—dinner with a friend on a weeknight (I thought this was a barbarian concept my first few years of the company. Have not regretted doing this once since).

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Burnout produces bad work

I can pretty confidently say my best work has not come in the moments of peak burn out.

Too many times I’ve come back from taking a rare day off and have felt my output in that week was so much higher than the weeks before.

Which…makes sense.

I once had a conversation with my therapist where I said I was feeling good.

My insinuation was that our work was done.

His insinuation back was that this meant it was time to go deeper.

He was right. When you feel good, you can get into more levels. When you’re stressed, you can only discuss the surface. The same is true with burnout. The time to prevent burnout is not when you are burned out. Then, it is too late. The time to do it is before you are burned out. You don’t have to wait until you need to recharge to recharge.

When your phone is at 20% battery, do you wait until it is dead to plug it in?

This isn’t anti-work

Starting a company at 23, I’ve missed plenty of moments with friends and family. That’s part of the deal. You don’t build something meaningful without hard work. Late nights, weekend Slacks, and social life sacrifices.

But I also think you lower your chances of success by performing constant exhaustion. Linear and Ramp are great examples of modern unicorns that reject 9-9-6. And still win.

Burnout isn’t a badge of honor.

Burnout doesn’t announce itself. It quietly renegotiates how much of yourself you’re allowed to use.

Life isn’t a performance. Don’t put on a show. Build something that lasts.

I probably should remind myself of this more, but am very comfortable telling it to others. Quitting your job. Launching a campaign. Walking up to someone at an event. The worst-case scenario is far better than you think.

Two: most people think it is riskier than you think

I feel confident in advice one because of the delta I believe in advice two. If everyone, literally everyone was starting a company, it would be far riskier.

Three: you do have a choice in the matter

This may seem to contrast with my fatalist views. In that I think the choice you will make is pre-determined. However, that is still a choice. If you want to, you can. Even if the choice is predetermined, you still have to be the one to make it. Which starts by acknowledging that there is a choice to make (or not make). and that’s where your agency lives.

Four: ask for things

Four relates to one, so five won’t relate to two. But you can see where I’m going with this. Ask for what you want. And then get creative with the other side about getting it. I say my career started with cold emails. I mean it—you’d be shocked by who replies. By who will entertain your ideas.

Five: you should care about who you work with

If you’re young, you should find the people you look up to the most and join them. I don’t care what they are building. It can be Waymo for armadillos. AI for taxidermists. Just join them and get excited about learning the unsexy things.

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Six: we all have an ego. empathy is nice

We get upset when people don’t do the things we want. The problem is they’re not actors in the movie of our life. They have their own motivations. Everyone is allowed to be a little selfish. And everyone is allowed to not feel compelled to give you what you want. But you can use that. Once you’re solving for their needs, you’re on the same team.

Seven: fundraising is meant to be hard

Investors’ jobs are to pass on deals every week. Don’t take it personally. Everyone feels broken by the process until they don’t.

Eight: fundraising is meant to be easy

Once someone believes in you and your vision, it’s “easy”. In that venture is an alignment game. How do we both feel incentivized to want the same goals? The question will be if you do have the same goals.

Nine: narratives are helpful

We need purpose. Or a belief in a belief which dictates the decisions we make. So we tell ourselves stories. Sometimes they’re devices and we know that.

Ten: narratives can be dangerous

Don’t put yourself in a box. Don’t limit yourself because of the story you’ve always told. Don’t envy what someone else did. Do it.

Eleven: meet strangers

We live in a digital world. Often too much so. Sit down at a coffee shop. Or bar. And say hi. And hear someone’s story. Be a passenger. Learn.

None of this guarantees success. But all of it guarantees movement — and movement tends to be where good things happen.

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I remember getting dinner with a friend in mid 2024. Just two founders of boring software companies from the 2021 bygone era.

“Should we just…start AI companies?”

We felt a real fomo. We felt a real sense of poor luck with timing. Normally, companies compound. The longer you’re in it, the more you’re rewarded. But in a cruel twist of fate, it felt like everyone who started companies after us was leapfrogging us. We started companies in the worse 1-2 year cycle in a decade, and our reward was that those who waited it out got to raise more, scale quicker, and create more disruption? Should we just…follow?

These weren’t our daily musings. And I embellish a tiny bit for dramatic flair. But the desire was real.

We weren’t going to leave our companies.

Though if you read a lot of tweet threads in 2024, we probably should have. Not just because AI companies were growing so quickly, but because, according to “experts”, AI was going to eat the lunch of traditional SaaS companies. Public stocks were falling of those companies viewed as primed to be vibe coded to oblivion.

The term AI-native was coming along as a common descriptor for companies who started with AI. Increasingly, I reject this as a long-term genuine descriptor. Instead, I’d bucket the universe into AI-First and AI-second companies. In AI-First companies, AI is the core product today. Examples include: Hebbia + Rogo (finance), Harvey (law), Cursor + Cognition (code-gen + IDE). AI-Second companies is a term I’d use to refer to software companies who are using AI to enhance the existing product. Ramp is the best example of this type of company. These definitions are not perfect— Handshake potentially straddles both as a cloud-native company who built an AI-first product.

But in 2024, we felt the FOMO of these Ai-first companies.

There were two paths:

• Integrate AI into the product we’d spent years building

• Abandon it to chase AI-native hype.

We chose the former. In hindsight, it was the only path that compounds. 16 months later, the landscape looks nothing like the fear-filled predictions from 2024. I’d argue that depending on category, the companies best positioned to win in AI are the boring software companies. The ones who already had products, distribution, data, and customers. Who could become AI-Second.

Five years from now (probably shorter), I doubt we’ll look at AI companies vs non AI companies. VCs will invest in companies who use AI. Just like today they don’t particularly spend too much time non cloud-native companies.

Companies aren’t started because they are internet-native/cloud-native. It’s because they leverage the technology to drive change in the areas in which they operate. The same will hold true for AI.

Remember in 2021 when everything was a crypto company? And you’d say “but why does my mortgage need to be on the blockchain?” and people would just smile. Yeah—that was a bubble. Now we can say “where will AI play in the underwriting of my mortgage” and the answer may be in half a dozens pots—in the application process, in the CX bot used to get more information for you, in the outbound marketing to land you. I get ahead of myself.

We don’t know how the dust will settle with AI. Who will pay for the tokens?! But I don’t see a future where it isn’t the bedrock of many of these processes in the next decade. The technology is simply too good at doing tasks humans do imperfectly, expensively, and time-intensely today. This isn’t 2021 mortgages on the blockchain. It’s real, and not going away.

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Who has the “right” to win

Disclaimer: no one deserves anything. I’m not going to argue that established tech companies have more of a right to win than newer entrants. I candidly have no clue. AI didn’t reset the chessboard; it just added a new piece.

Mercor took off in two years to > $100m arr for model training/data labeling. And then Handshake…a recruiting platform that had been around for over a decade…did the exact same thing in roughly the same space (on top of their initial $100m business!).

Handshake has amazing leadership. And this example is arguably a bit unique—they had a massive audience to tap into for labeling. But that’s kind of the point…companies that have established some form of longevity likely have done it due to a reason.

Sales is about distribution. A younger generation would say it is due to marketing, or hype. I’d modify that to say it is about how you find unfair ways to distribute your product (marketing could be one of those channels). “AI-native” companies have the ability to find a wedge. And then they must fight to retain customers. “SaaS” companies have built-in customers who could use them for AI (see Handshake!).

Ramp, and focusing on the right metrics

Handshake is an interesting example of where my AI-first and AI-second definitions blur. For most software companies, I’d look to Ramp as a north star.

We were an early customer in January 2022, and they’ve consistently delighted since. With all of their innovation, their website copy has essentially stayed the same. Ramp will help finance do two core things:

• Save time

• Save money

Their product already did that before AI. Their bill-pay tool flagged invoices you already paid. Their accounting integrations made it easier to sync data and close books. They auto-fetched and matched receipts from your email to spend. Ramp did this through a platform which brought together corporate cards, expense management, and AR/AP. And with AI, that is still what they offer.

If you look at their products highlighted on the website, seven of the eight SKUs don’t mention AI. Yet when you go to their Ramp Intelligence page, it’s clear to see how they’ve used AI to make their entire platform better.

This is exactly how software companies should think about AI. They should become AI-second. Use AI to double down on what makes your existing product great. We’ve tried to emulate this approach at Footprint. Like Ramp, our two goals since starting the company were to help our customers:

• Reduce fraud

• Improve conversion

We use AI to accelerate the capabilities of our product to do exactly that. Agentic workflows live inside of our core onboarding engine to chase these KPIs of which we measure success. Together, they’re the product.

This isn’t to say that AI-second companies can’t have AI-first products. They can (and should) where it makes sense. Never before have we had technology which can smartly automate manual knowledge work. AI-second companies can benefit from many of the same benefits of AI-first; create magical moments during a sale, deliver products at an easy-to-use entry point to shorten integration timelines, expand TAM by expanding the amount of work thought to potentially do in a space. And conversely, AI-first companies will build AI-second workflows. Both are good uses of AI.

I expect the lines between “ai-native” and not to blur in the coming years. Heck, I think the term “ai-native” will mostly go away. Adapt or die. Not in a scary way; I expect most software companies to embed more AI and become AI-second, and AI-first companies to build out more complex features away from their use of models. AI isn’t the product; how you use it as part of your product is what will matter. You expect companies to be built on cloud today. The same will be with adroit use of AI. The result will be that those who don’t use AI will be penalized, but those who use AI won’t win due to just their use of AI.

Swimming

What are moats when the cost/time to deploy AI features is dramatically reduced? One aforementioned camp will say some form of hype. I’d argue it’s much closer to moats those “dinosaur” public SaaS companies have long experienced. Regulatory moats (you can’t vibe code relationships with regulators or bank approvals). Integrating into workflows. This one may sound paradoxical: AI is often supposed to be replacement. I think that is looking at too small of a picture. The work you’re replacing is still part of someone’s workstream. In law, it’s how you interact with paralegals. In finance, how an MD may interact with an analyst. In our space, it’s how risk and compliance interact with manual review. Will platforms build the tools that those upstream users actually require?

This is why historically…incumbents win. Don’t get me wrong. I’m a Series A founder. I believe every day that the underdog will win :). And yet, statistically, I’m wrong. Look no further than Google and AI. What’s the largest bull case on them now (even more than Gemini 3)? That they built the most profitable machine the internet has seen to date which can fund their compute needs for the foreseeable future. And historically, incumbents benefit the most from innovation. Amazon has built a large enough business they benefit the most from advances in everything from robotics (more efficient warehouse ops with fewer humans) to AI (better route planning can save billions of dollars).

Yes, this is weird framing coming from me. This is not a love letter to big tech winning. But it is definitely a love letter to those boring software companies from the five year vintage of ~2017-2022. The amount you had to fight and claw to build your moats. Well that is your biggest distribution advantage in AI today.

And let me be clear, the incredible AI-first companies being started today also have an incredible chance to win! By building the unsexy old software moats. I’m not here to deny that. Just not say they’re destined more than anyone else. It’s a race of AI-first to build those other features vs cloud-first companies to smartly integrate AI into their platforms.

We’ve seen it the last quarter as we’ve brought our AI products to market. Half of our largest customers began using it in the first week. At Footprint, this played out exactly as the theory predicted. When we launched AI features, our customers adopted it in week one because we weren’t selling AI. We were making their existing workflow better.

So yes, you can look around and be sad. You can look at Harvey and wonder why you don’t quit and build an AI-native company.

Or, you can be Ramp. And realize being “ai-native” is not some gate-kept primitive. You could do it. In fact, I’d argue you’re incredibly well-positioned to do so. Choice is yours.

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“But you do realize, it is your choice.”

“Yes, but we know what I am going to do. What I was always going to do.”

I’m having dinner with a good friend. He’s wiser. Has seen my story play out. Perhaps in himself, certainly in others.

We discuss the future.

II

I certainly go through cycles with myself. On how I view the future. On if I want to view the future. This has been a year for me living more in the present. A respite from my typical reveries. It’s been nice. A vacation of the mind.

We know vacations will end. It’s why we enjoy them. The ephemerality presents an ensconcing excuse to truly let go.

This one lingered. In a good way. I used to write essays about topics I did not understand about the self. The last year and a half was both an expression of not knowing those answers and an embrace of being ok with that.

III

We discussed at dinner a decision which did not seem like a decision to me. Years ago it was obvious. Then at times anathema. But by time it came to make the decision, it was once again a foregone conclusion.

I have changed, no? Well, certainly. But I was always going to change, yes? Evolve into the person who from a new mindset would make the same choice.

Carlos Ruiz Zafron writes in one of my favorite books “The essential part of the matter had been settled before the story had begun, and by then it was too late.” Is that true in life?

I don’t want to be pedantic. I don’t mean to be. Yes, we can chase fatalism to the end. I suppose we were always going to make the choices we did. In a vacuum, that was our natural decision or string of decisions at the time.

I stopped thinking about fatalism a few years ago. A few months after I started thinking about it, after reading Ava’s post on Bookbear express about the subject.

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IV, Option A

I don’t think I was always going to make this decision. The timing worked out. The timing allowed the decision to happen to coincide with the decision a younger me also would have made.

If we make the decision we were always to make, but for reasons different than the initial ones, is that all that fatalistic?

I used to view fatalism as melancholy. Not as a complaint. Over lack of free will. That story, even as much as I believed in the concept of fatalism, never resonated much with me.

My view is that there are likely a few paths which any of us may take. It’s not infinite. It’s more than one. That, perhaps, is pre-determined by who we are.

Which path we go down? That’s a result of the person we are at the few compelling events which actually make us choose.

IV, Option B

That’s one of my explanations. I have another. Where there really is just one path that we were most likely to always go down. But in this one, there may be several reasons we keep following the signs.

One is without question. The natural extension. The second I find difficult to describe. Herman Hesse writes in Siddartha:

“Words do not express thoughts very well. they always become a little different immediately they are expressed, a little distorted, a little foolish. And yet it also pleases me and seems right that what is of value and wisdom to one man seems nonsense to another.”

That’s me here. But I’ll give it a try. To me the other reason is a combination of this Buddist thought of we want to experience the full version of the different parts of ourselves or paths we go down. (That at least was my take-away from the book, but after not finding a quote which backed it up I opted for the above quote). In other words, a younger me would have made a decision for X reason. Older, a bit wiser, I make same choice because I am already on the path, at which point I still find it most optimal to finish the path. Maybe I walk down it differently. Enjoy it in a different way.

And then, whenever the time comes to “change paths”, it is actually just because you reached the conclusion of that path.

V

I accept both of my explanations. Because they resonate me, and that’s enough. And I have the gall to write a substack on philsoophy despite having still not finished The Archetypes and the Collective Unconscious by Carl Jung.

I do think that we have free will. We evolve. I dismiss the notion we were always going to—we still made choices.

I do, however, think there are only a few times when we actually actively choose from a set of a few paths we would have embarked upon. And I do believe most of those roads will connect anyways. I think the paths that would have made sense for us. The ones we truly wanted to travel. I believe we’ll end up there. Maybe the one we’re on is shorter than we realized. Maybe the counter factual wasn’t that long of a trip.

So I guess I’m a fatalist. I trust myself. My younger self. The decisions to make decisions.

My hope is that I grow enough so that as I age, more of the roads feel newly intentional. The traversing is less of an exploration of a younger self. That’s growing up. It’s understanding why you went certain ways. It’s enjoying the roads you picked. Finding new reasons. Honoring yourself. Loving yourself. And accepting even if you had a map, there would be no where else to go :).

__

The waiter asks if I’d like anything to go.

I glance at my friend, then at my plate.

“No,” I say. “I think I’ll stay here a bit longer.”

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She told me something startling: “I don’t think people want vulnerable leaders anymore.” Her broader point: people want confidence. They want certainty. They want laps of victory. Bravado.

This wasn’t her assessment as to whether this was right or wrong. Rather her belief of the times.

A few weeks into this Substack, I have to agree.

In the past few weeks, I’ve posted the following posts on Linkedin:

• A picture from James Bond hyping up Footprint’s free gambling giveaway

• A post saying our new AI product is ripping

• A link to my Substack about learning to fail

The James Bond Casino Royale post got 6,000 impressions. The AI one 13,500. The one on Failure…under 2,000 impressions.

Our AI product is doing well. HOWEVER. No one who engaged actually, verifiably knows that (or at least very few). No one even knows what it does (in that we haven’t publicly announced it yet and the post gave no detail, ergo everyone engaging was just fired up about the prospect of an AI product).

I used to publish my investor updates in 2022. I do think it was a different time. In a year where markets were down, I suppose people had to be vulnerable. I once wrote that vulnerability was a strategy credit (credit to Ben Thompson for the term). No one back then was truly up and to the right. So vulnerability became confidence.

In a way, people felt permission to struggle. When I would write about the difficulty to find self worth when the company wasn’t doing well, people felt empowered to resonate.

When so many are (on paper) doing so well, it does seem that folks no longer want that openness. Visibility into highs and lows. That’s at least what they’re saying.

And as a result, LinkedIn has become the new Instagram. Nothing is real. I tell our sales hires my LinkedIn posting philosophy is a quote from the former (disgraced) first lady of the Phillipines (corruption charges): “Perception is real, and the truth is not”. It’s not that I lie on LinkedIn. I promise I don’t! However, this is my way of saying LinkedIn is slop about momentum.

And that’s important. For startups, momentum is everything. It can become a self-fulfilling prophecy. Investors want to invest in hot companies. People want to use the best vendors. Everyone looks to their peers for advice and signal on who those companies are.

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People say be ok with cringe. I don’t disagree. But I feel I must console people about others Linkedin posts the way you’d use to chat about Instagram being fake. On IG, you only see vacations, photos with filters, and smiles. On LinkedIn now, you only see screenshots of revenue charts with no axis (I’m guilty of posting one literally three days ago), posts about the discovery of more intense versions of 9-9-6 (I did a shitpost on this over the weekend and think half of the reactions were encouragement not realizing the satire), and guides about doing things the right way.

I think people still, deep down, like vulnerability. They just won’t say it. But they’ll reflect on it. Feel uncomfortable around it. And that’s ok. People don’t know what vulnerability means. Being confident is a spectrum with a clear axis. The more bravado, the more confident. I used to think vulnerability meant pouring out your feelings. That now rings to me as a more hollow definition. Incomplete. Perhaps close in Merriam Webster. But vulnerability is more of a curve. The emphasis isn’t on the depths, it’s on what it taught you. How it changed you.

That’s why it is much tougher to write about than pure confidence. The latter is easy to max out. The former is more nuanced. And going back to our analogy, people don’t want nuanced Instagram posts. They want obvious posts. The feed wants Surf Lodge in July! And the feed wants your revenue screenshot and claims of certainty you’ll be the quickest company to hit an arbitrary ARR target.

So yes. LinkedIn has become the new Instagram. And maybe that’s fine. Maybe the feed is supposed to lie so we don’t have to. The LinkedIn exec told me people don’t want vulnerable leaders anymore. Maybe she’s right. Online.

But the leaders I respect most are still the ones who’ve looked loss in the eye and kept building. Confidence is what you post. Vulnerability is what gets you through the moments when there’s nothing to post.

When the dopamine wears off. When the numbers stop climbing. Or heck, when they hit new heights. At the end of the day, there is something past signaling strength. There is strength in silence. Strength in embracing what actually got us there.

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Three years in a row, I’ve had the same conversation with a friend starting a company.

Me, with little context, opens the dialogue by saying “I don’t think this person is your co-founder”

“Why,” the friend responds incredulously. Their voicer a mixture of anger and surprise.

“Because this isn’t getting dinner next Friday. It’s a massive decision. If they’re not all in now, they’ll never be.”

Each time, the friend would at some point realize this. Each time they would find a new co-founder. It would work out as it was meant to for everyone involved.

Part of my confidence here comes from having lived this story out myself. I at first thought I was going to start Footprint with someone else. I had know them for a while. On paper, I thought they would be an excellent partner. I even introduced them to Index, who would lead our seed round, as the person with whom I planned on building Footprint.

He told me he needed a bit of time to think. And then a bit more time. I was never forceful. I was afraid of him walking. Afraid of being alone. What would the investors think?

And then after Thanksgiving, he told me he did some reflection, and that he didn’t want to do the company with me. I was devastated. I remember crying on the floor of my apartment. How had I already failed? The company hadn’t even started yet.

I face-timed my good friend George. Former roommates, George was a founder and someone I knew would give me the tough love I needed in the moment. He told me to get on a flight to SF. And ask the smartest people I knew there the smartest people they knew there. Rinse and repeat. Come back when I found the perfect co-founder.

So I essentially did that. Which is how I met my amazing co-founder Alex (more on him below). But getting back to the initial person. Firstly, he is still a good friend. He owed me nothing. And his decision has worked out very well. He stayed on at a company which has grown incredibly. Unsurprisingly, he’s been a star there. Don’t be mad at people who won’t do what is on paper a very silly choice with you.

I tell friends starting a company isn’t a dinner reservation. Who amongst us hasn’t been a bit on the fence on a dinner we commit to a few weeks out. Life got busy. Work has been intense and we’re tired that Friday. We hear about a guest who will be going who we didn’t initially realize would be in attendance. We get a superior invite—a friend snagged a top reservation and you’d be remiss to not attend. Our Hinge absolutely popped that week and someone cute wants to get drinks. You see, there are a dozen plus totally justifiable excuses that may come up for you to decide against going to the dinner you initially RSVP’d yes to.

I typically hear the same reasons from friends about why their co-founder candidate hasn’t fully committed yet. “They want me to raise first” is usually the first one. Or some broader assertion of “they want me to de-risk it.” Other objections may be if they’re meant to be a co-founder and CTO. Some want to see a customer first.

But here is the thing, this isn’t a dinner reservation. This is arguably the biggest decision of your life save marriage. I promise you, if they’re uneasy now, they will be extremely uneasy one month in. When you actually get punched in the face. Startups are never de-risked. You never have enough runway. Nor customers. When things get tough, you want to lean on your co-founders. I’m lucky to be that way with Alex. I have friends who say when they have tough times, they’re worried about confiding in their co-founders. Don’t want to spook them. That thought scares me. The job is lonely enough as it is.

In other words, all of those reasons my friends justified not moving onto a new candidate are disqualifying in my mind. You’re not owed blind allegiance by those you’re soliciting to start a company. However, if you’ve been “working” with someone for a month+, you should know. If you’ve quit your job to go all in, they better quit (and if they say you both shouldn’t quit yet, you should quit and find someone else). There should be a moment of no return for them. No escape latches. It should be the same milestones. Don’t be afraid to ask them to put skin in the game. To commit. Don’t talk them into a job. You’ll need to persuade top candidates of course, but there is a line between convincing someone you’re the right co-founder to build with and convincing someone to do a job they are uneasy about taking on.

My friends will ask me if it’s a bad look to investors to not have the co-founder situation figured out yet. I tell them it’s not ideal, but it’s far from disqualifying. Yes, if you had a locked in co-founder who was best friends since birth, was a math olympiad winner, went to MIT, and lead engineering at pick your tech darling, yes you’d command a higher multiple.

But as a founder CEO, investors are betting on your ability to solve difficult problems. Finding an amazing co-founder is perhaps the first of these. And it certainly won’t be the last. They’re underwriting your ability to find someone great. No need to stall VC convos. Obviously don’t rush your decision, but it’s a nice time force to make you focus most efforts on the co-founder search, and they can help make intros.

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Co-founder Equity

Don’t fall into the following trap. “Well I’ve been working on this for a few months now and they’re just going to join as I already have VC interest. Should I get more than 50%?”

No, no you should not.

Some of the best advice Shardul from Index gave me was to go 50-50 with your co-founder. In his words, it’s a good forcing function to find someone amazing. You want someone so good you feel lucky to get them for 50-50! The best way to make your equity valuable is by bringing on a world-class co-founder. 50% of something huge is worth a lot more than 40% of something 80% the size :).

I get a few objections to 50-50:

1. I’ve already done a lot of work

   1. Sure! But you are just getting started. You’ve actually done very little in the grand scheme of things. There will be many moments (especially in months 1-6) where your CTO will empirically do much more work than you. Would it be fair for them as a result to ask for a change of equity? Nope. There are periods where both of you will be producing more. That’s natural.

2. I already have investor interest

   1. Nice! That’s one of the ~three most important roles as a CEO. Should not impact the equity of your CTO

3. I think they’d agree for less than 50-50

   1. Maybe so. But is that a good way to start a 10+ year relationship? In my mind, it is not. And does this mean you’re looking for the person who is good enough and will take 40% instead of the best candidate who you’ll give 50%? As I promise you good enough is not enough here.

A great co-founder/CTO wears three hats

As a co-founder/CEO, you’ll pretty much wear the same hat across a few domains at the start: selling. Whether investors, recruits, or early prospects, your job is to get people excited about what you’re building. It will be a slightly different pitch for each of those buckets, but the same mindset. This will change as you grow and you have to build up new functions (finance, ops, partnerships) and begin managing the sales team as you move away from founder-led sales. But for the first ~two years, you have one job.

Your co-founder/CTO, by contrast, has three jobs in the first year.

They have to be your first IC. Probably a fullstack IC. To build out your MVP. Then they must concurrently be your first EM when your founding engineers join. And when your team and product both grow a bit more, they then will become your first PM.

Not that I was qualified to start a company when I was 23, but this is a good reason why I think it is tougher for a CTO to be right out of college than a CEO. In engineering, someone needs a bit of time to prove as an IC before becoming an EM/managing other engineers. Or to be given products to lead. Selling is more of a “you’re born with it” trait.

Yes, you don’t need all three per se. You can adjust your early hires accordingly. But it’s very helpful! I was lucky that Alex really was a unicorn. A gifted engineer who built our vaulting infrastructure still used to this day in the first two months of the company. An incredible manager who our early engineers compared to “the best TA I’ve ever had.” And someone with incredible product sense. Who can figure out not just what to build through customer interviews, but how to build it.

When I met Alex, he was five years older. He had built a company in high school (an app to track busses in real time in Boston), went to MIT for his undergad and masters iN CS + cryptography under Turing Award winner Shaffi Goldwaser. Started a GC-backed company in the mobile auth space which would get acquirewd by Alkami. And then managing teams there as he built out their MFA product.

Yes, I’m not sure how I got him to build Footprint with me.

However, within a week of meeting him, I asked him to join me 50-50. Within two weeks, we had done reference calls on each other, product whiteboarding sessions, and he had begun joining investor calls as my co-founder. We also did a weekend retreat, where we went through the First Round Co-founder dating questions (I am a fan of these—some are corny but just do it) and got to get meals with each other. I am a huge fan of this as a practice—you have to see if you enjoy spending time with this person. They’re not just check boxes of ability. You’re going to spend an ungodly amount of time with them. You better make sure you enjoy each other’s company!

Polarizing Decisions in Life—not just founders

This framework of polarization is true for many elements of life. To quote one of my favorite books The Shadow of the Wind, “The essential part of the matter had been settled before the story had begun, and by then it was too late.” I think this is true for many things in life. That guy was never going to start Footprint with me. A date who hasn’t texted you back within a few days likely isn’t interested in a second date. I’ve never had a recruit accept an offer more than two-weeks post offer. Once you know someone likely won’t last at your company, you won’t change your mind (but you will likely wait a few months before discussing this with them).

Now not all things need direct polarization. While it would be nice if people came to every dinner and Partiful they rsvp’ed to, you likely don’t find it worthwhile to call people leading up to it confirming they’ll be there. Dinners don’t have much of a social contract.

But for other things. Don’t be afraid of rejection, like I wrote about in a previous post here. You can wait, but you’re just prolonging the inevitable. Which means you’re postponing your actual search.

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Learning to fail is a far more valuable skill than learning to succeed. You can’t truly understand the latter until you’ve mingled with the former.

There was a time I thought Footprint was going to fail. I remember the moment viscerally. Laying in my parents’ bathtub at their apartment. Listlessly. I had sat for so long, the water had gone from hot to lukewarm to cold.

It doesn’t really matter that I was wrong. It doesn’t really matter that, I suppose, I still could have been right – just many years too soon.

What matters is that I had never actually stared at failure. And as a result of that, and a culmination of other unhappy habits, failure was much bigger than the moment. It felt like an invalidation of my life. Milestones were stepping stones to some ultimate goal. Success would beget enough success to find that. Even one disruption to that pre-defined journey would topple the whole tower. I was so afraid of failure because failure was this gigantic obstacle. When you never learn to fail, you overestimate its impact.

Another element to this is changing your definition of dreams. Another way to view failure is the disruption of you accomplishing your dreams. Failure wasn’t just a bad moment, it was a force working against my inertia. But, I think both of these relationships must be evaluated. And the one with failure likely will be a pre-requisite to examine your dance with dreams.

Life feels different now.

I don’t look to our Series B next year as the milestone I need for happiness. Nor the milestone I need for success. I find happiness in the journey. I don’t view the potential to not achieve future milestones as failures which would invalidate the whole journey.

Success in the elements and parts of me which make both today and tomorrow possibilities. I’m also not sure if I would have gotten there if I never had moments where I wasn’t sure about my ability to reach the next milestone. It’s not that the concept of failure makes you accept failure. It changes your relationship to the definition of failure. It’s less nebulous. More tangible. And by being more real, failure can metamorphose from a monster under your bed to a made up phenomenon.

You’ll note that the start to this essay is titled Take Two. You may have wondered why. You may have also not taken stock. Or, you could be wondering why I have switched to second person narration. All would be fair responses!

It’s because this is my second attempt to write about failure.

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Take One

There are a lot of bad reasons to start a company. I’ll write about them soon. But before I try to talk you out of those reasons, some people may be past the starting line. And may be wondering what to do next.

I recently saw a friend at a party. He had wanted to start something. A few weeks in, he had been hit with a realization many feel after the initial honeymoon period: building is tough.

“Will it get easier?” he asked, looking to me for comfort.

I paused.

“Probably not.”

“Why do you sound calm in saying that?” He had noticed the dichotomy between my tone and my words. “Because you’ll learn to fail.”

Let’s be honest, most young people who start companies have never failed. They’ve gone to good schools. Gotten a cushy job out of school. Their imposter syndrome in part stems from having never had a chance to respond to failure. Whether aware or not, they have no clue how to actually face adversity.

Not stemming from a midterm. Or a deadline for a client. They’ve been successful. This was the next step. Everyone in their life also assumed it was their next step. In the eyes of others, they’re the one who is to go do something even more ambitious. More difficult to others, but not to them.

They think a lot about others. The folks whom they would like to continue to view them in such light. And the folks whom they think have done whatever they want to do.

Those who hold you in high regard will likely always do so, regardless of the outcome of your B2B SaaS co (so long as you don’t get 30 Under 30 and promptly head to prison, but even in that scenario they’ll still think you’re smart!). The professional mentors know building is hard. That success is based on luck in many ways. That it is equal measures the painter and the supplies they were given at the shop.

Failure is the guaranteed gift of starting a company. Staring it down. Will you make payroll during a bank run? How will you tell the team you couldn’t raise a round? What happens if you miss numbers a second quarter in a row?

Because when you contemplate these answers, you can go two directions.

One: the world is melting. A crescendo of ensuing bad. My company won’t be successful. I’ll never become rich. It spirals. Will never find happiness. Will never find love.

Or, you can view it through a less binary lens. The things you want for vanity likely won’t be changed that much. The chances of you getting them won’t be all that altered by things which seem big in the moment. Those will happen because of you, the person. Not due to one fund raise. Or one hire. Or one sale.

In fact, investors like second time founders who have had to answer these questions. Who encountered failure and came back a second time. They have learned many lessons. One is how to genuinely not be scared of failing. When you’re scared of failing, you get desperate. You think short term. You play to not lose. You flail.

When you play to win, you take risks. I think founders—people in general—all take fewer risks than they should. Because they over-estimate the negative ramifications of the risks and under-estimate the positive expected value.

You don’t need to start a company to learn to fail. In fact, contrary to what I said, founders have “failed” at many things before starting companies, they often just didn’t view it that way in their minds. Failure, like happiness, is a construct.

Reflection on Takes One and Two

As you’ll see, Take One is far less personal. I was afraid of the failure I would face if I couldn’t accurately reflect my emotions. Or feelings. But even if I can’t really describe that moment, I want to publish Takes One and Two. To show you that it’s okay to fail. To show you that when you end up in the bathtub, you’ll trust me more because I shared my experience instead of just giving a pedantic lesson about some anonymous conversation I had at a party.

And when you get there, I hope you smile. Heck, I hope you laugh. Promise me you’ll laugh? Then grin. Take stock of whatever objectively dumb thing drove you to question everything. Then take stock that you’re in a lukewarm bath tub and agree that the first success you owe yourself now is draping yourself in a towel. Once ensconced in Turkish cotton (or Egyptian cotton; I don’t judge your bathroom accessories), you may get back to being sad. And mourning. At this point I won’t ask for a wry smile or even a chuckle. But I ask for gratitude to yourself.

You put yourself in a position to fail. Do you realize how few people actually do that? And do you realize how much more confident you’ll be the next time you do that, regardless of outcome? Because you sat in the tub. You saw everything flash.

And flash I did. I saw a future of no love. Of family and friends no longer believing in me. Every stupid belief I saw. It was dumb but it was my truth and I had to laugh about it and cry about it and reflect on it.

That is why failure is a super power.

Don’t desire to get back there. Don’t let it fuel you. Don’t go for revenge. Just learn from the feeling. Not how it brought you down. How it actually did not impact you half as much as you expected. It didn’t destroy you.

I don’t find failure motivating. I used to be afraid of failure. But I wasn’t motivated by not failing, I was motivated to achieve what I thought I would get if I did not fail. This view was wrong. Both in that failure is not some binary thing. Where a bell is rung and you are paraded through the streets. And at the same time, success is not binary. If you don’t fail, that does not guarantee all of your wildest dreams come true.

However, when you’re able to act without fear of failure. Either because you no longer view those milestones of success as so binary, or because you’ve seen failure isn’t so bad. Or both. Well then you’re going to succeed a lot more.

This obviously applies in far more to life than starting a company. A Substack went viral last week encouraging men to walk up to more women in person. The core thesis? Not enough try, too confident they’ll fail and afraid to take the chance.

This is true in sales. In marketing. Heck, in getting adventurous ordering at restaurants. The best things come with risk of failure. Build a portfolio of things that may fail.

We spend most of life avoiding failure as if it’s a threat to our identity. But the truth is, it’s the only thing that ever teaches us who we are. Once you stop fearing failure, you stop mistaking comfort for safety—and that’s when life actually begins.

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Stamps

The term stamp of approval is weighing on my mind as I look for a proper opening here. I’m bad with expressions. My mind begins to cross examine the saying. Should it not be a seal of approval? I guess both are expressions? In ancient times, you’d use a wax seal to formally authenticate an item. And I guess at some point that became stamps?

I digress (purposefully). The parenthetical there reads unnecessary. Performative in a way. Preference for prose over craft. I digress again. I’ve been thinking about the authenticity of the document before and after the seal. How it changes. If we discover a letter from a Roman King, our appreciation for it changes if it has a seal. Without it, how do we know these were the true writings of him?

Let’s say the letter is to his wife. Would the meaning of it now change with the seal? I’d argue yes. What was maybe once a tender expression of love now seems to have subtext. Why did he feel the need to have this epistle officially certified? Was he sending a message not found in the actual words? Did he exude such arrogance he simply thought all of his words needed the seal from the heavens?

And does the meaning change if the queen does not care whether it had the seal or not. For our queen, the letter is a letter. It followed a process, like all letters presumably did to reach her eyes for gazing. Perhaps a courier read it. Perhaps two. She knows that by the time the letter from the king reaches her, it has been read at least once. Sometimes the King feels the need to seal it, sometimes not. She is not sure if he even knows she has her most trusted servants read it. That the seal was broken by the time it reached her. She is not sure if he would care.

This introduces a second element. Does the stamping process change the intention of the writing for the author, and should it change the process of digestion from the audience? And then, does the dance of these two concepts add an extra element of interpretation?

I won’t lie. I have not been thinking a lot about stamps. And I have little knowledge surrounding the process of ancient postal systems. The above was just some historical fiction. A potential re-enactment. A useful literary device until it felt the point had long been proven. Or at the least until it felt my fun little creative exercise would not reach a point if it had not already. Ergo, any continuance of it felt futile.

Ok, so why have I been pretending to think about stamps? Glad you asked!

I’m Eli

I wrote a 6,000 word essay titled I’m Eli. Call me biased, but I think it’s well-written! It describes my life as a performance. It does so in the format of a play, stage directions, playbill, and all. I’ve shared it with about two dozen people. One started therapy after reading it. Several asked to share it with folks they thought would benefit.

As you can probably guess, I’m Eli is about KYC. Like many of you (I’m sure), the thought of poor identity verification practices is so horrifying it causes grief amongst those I consider friends and confidants.

I laughed in a cafe named Hungry Llama while writing the above stanza. it serves a nice purpose. A comedic respite. After my whole stamp salvo. Once again, I laughed. And my rule for writing is similar to my rule for stand-up comedy; if the one with the pen does not enjoy it, no one else will. That does not mean people will like it. However. It increases the chances. And that’s good. I digress.

I’m Eli is not about KYC. Shocker! It’s about life. My reflection on the last decade or so. What possessed me to start a company when I was 23. The dreams I’ve had. How my understanding of happiness has evolved. The dreams I maintain. How happiness became a part of me instead simply a concept I wrote about. KYC.

I like I’m Eli. It’s also a lot. It’s intense. I shared it with an investor I am extremely close with. And he pointed out the dichotomy of publishing it widely. To date, I’ve shared it with people personally. We’ve had one on one conversations about these themes. They read my performance as a medium to have a conversation with someone I knew and cared about.

But to publish I’m Eli. Does the meaning of it change? If the intent goes from I want to help friends to I want to help the world? I’m Eli is about how my life was a performance. Why I stopped seeking validation from others. To find it in myself. Would publishing this be a continuation of the performance? An attempt to validate the last decade? A stamp of approval if you will…

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Stamps Round Two: Authenticity

Yes, my little stamp analogy has come back! It was perhaps an unnecessary detour to talk about authenticity, but it did at least allow me to slip in the following use of the word aqueduct in context in my writing. And personally, I’m thrilled to do so.

After reflecting, I thought the investor was right. Well right enough. I was open to the idea that the seal changed the meaning of the letter. And the ensuing Plato’s cave he put me in (pictured in the icon to this Substack) was enough for me to change course.

This is not my poll on if I should publish the essay. I will at some point. But it’s my way of getting back to stamps. The idea of ancient seals was their uniqueness. I’ve long thought in binary ways. Ideas. Emotions. Moments. They all had to be stamped.

I haven’t written philosophical investor updates in two years. Instead, I began writing updates about the business (boring—this is the only time I’ll call KYC boring, but it is more in the context of writing investor updates about just KYC). My thought was I’d get back to publishing philosophy. Beginning with I’m Eli.

But as I reflected on the investor’s paradox, a middle ground presented. I did not have to wait to publish the most vulnerable essay I had written to once again write openly. With all of the cringe thought leadership I post on Linkedin, anything would be a better start back to the old updates I used to publish.

Why not start by talking about stamps?

Curtains

So I’ve started with this piece. It’s arguably about nothing (well I guess, maybe, stamps?). The other ideas I had to start with will come in the coming weeks. I hear a ton of terrible advice to young founders. On fundraising, picking a co-founder, and starting a company. I plan on writing on those subjects. What you’ll get out of starting a company. What you most certainly won’t get out of it. Why you should start one, and why you maybe shouldn’t.

But I didn’t feel entitled to start sharing those until I introduced myself. That was the other point of I’m Eli. To give me more credibility as a deep thinker. I thought my own stamp of approval would matter. Now I guess you’ll just have to take my word for it.

See you next week.