I quit my job
And here's what happened
Going Full-Time: Chasing The Dream
I quit my cushy tech job to go all in on my startup dreams.
My parents: “But the economy!!!! What if you get bad luck?”
Me: "But my dreams!!"
Here’s the journey so far…
Beginning of 2025: 0 revenue, 0 customers, 0 learnings.
End of 2025: 500k+ booked revenue, multiple customers w/ waitlist, seemingly infinite learnings.
100% bootstrapped.
0 outside capital.
100% Founder control.
After serving as Chief Product Architect at Dayforce—leading transformation initiatives around AI and developer experience across 1,600 engineers—I walked away to continue pursuing my dreams.
I’ve been bootstrapping my startup on the side of this responsibility for about a year, and 4 months ago I decided to go all in.
And my last week at Dayforce was a few weeks back.
There were a few lasts:
My last leadership team meeting
My last all-hands
My last executive extended leadership huddle
But coming out of this, there is a first as well:
My startup will have a continued relationship with Dayforce as a customer of mine.
I walked out of my 9-5 day job at Dayforce, a 1.8B revenue software giant, and converted them to my customer. I am definitely stoked to say the least.
I’ll share my tactics for this in the future, so subscribe and stay tuned.
Why did I give a 4 month notice?
Mainly because I believe in trying my best to leave any relationship, community, team, or organization I engage with, in a better place than when I found it.
I had a high leverage role, and I cared about my teammates very deeply. So I wanted to give it the right amount of attention to properly wind down, and plan and execute the right succession plan.
On the startup front going into 2026, I believe we are in a great position to grow revenue to the 2-3M range with some key levers in our control.
Let me tell you how I got here.
What was the timeline?
Winding down my first startup, I picked up the role at Dayforce in October 2023.
For about a year, on nights and weekends I went into exploration mode to figure out the problem I wanted to dedicate myself to for the next 10 years (and ideally, forever).
Many projects and some Co-Founder dating later…
September 2024:
I met Bryan Johnson, the Founder who sold Braintree Venmo to Paypal, then went on to try to solve AI Alignment via longevity (and from a genius marketing standpoint, find immortality).
October 2024:
I met my to-be Co-Founder, Jonathan McCoy, and after kicking some tires we decided to go after the vision of solving AI Alignment, with a philosophical and neuroscientific lens on AI Personalization.
Problem: How can AI understand humans to personalize value at the n=1 individual level, agnostic of the application UI or UX?
Answer: Build accurate digital representations of humans to personalize value. We brainstormed the opportunity to help Bryan with AI and hopefully get him as our first reference customer. We were cautiously optimistic.
November 2024:
We started executing, and we started getting the attention of Bryan’s development team in their Don’t Die community app product. We did research on their behalf of the AI Personalization problem. Personalized longevity protocols ended up being a need in their customer base.
I posted a TON in the app (to help build community too!), and successfully got some of Bryan’s attention. I did it in a genuine way.
I just started posting my Daily Meditation Streaks and daily gratitude posts. Things I was already doing, that aligns with the community ethos.
December 2024:
We got on an initial call with Bryan’s development team, starting our very first enterprise sales motion. We were willing to do work for free, to get the reference.
We got buy-in from their team that AI Bryan would be a great direction of collaboration.
Woohoo!
January 2025:
We worked tirelessly, nights and weekends, to get a demo and pitch together for the head honcho himself, Bryan Johnson, to give the official greenlight. By this point we were in the Blueprint Slack coordinating work.
We had the pitch meeting late January. I spent hundreds of hours on the slide deck and demo. I had to do it in front of a ton of cameras live at a Don’t Die Summit Bryan threw.
Wild.
The full story of the pitch is a story for another time.
But it went.
We got the greenlight.
February 2025:
We established regular touchpoints with the Blueprint team. They asked me to come help with their product portfolio. So I did some fractional Chief Product Officer work for them for their digital products, primarily focusing on the AI work but helping them umbrella that into a bigger strategy.
I got the opportunity to get super hands on with their user base which really accelerated our learnings.
March 2025:
We got AI Bryan into a small closed alpha.
I went to test the experience with real users live at a Don’t Die Summit. I learned much about what people (in this longevity x AI bent community) expect around AI Personalization.
This small feedback loop of learning was absolutely gold for us in the early stages.
We reconvened.
We had a roadmap.
April 2025:
We kept executing against our learnings, and things were looking really great to deliver on AI Bryan at a big scale to lock in our first big enterprise customer reference and case study.
We expanded the closed beta a bit, to learn more.
Things were on track to rolling out to 100k+ users.
But then…
May 2025:
Startup life strikes. At a high level, the Blueprint team decided to shift focus from AI Bryan to other things.
Damn. Gotta keep moving forward though.
At least we had the learnings and the customer and user relationships.
We learned the difficulties teams face in building personalized AI experiences firsthand. It is extremely complicated to objectively and measurably improve something that is non-deterministic—and that’s what AI is.
There is also a big core challenge all AI product teams face:
“How do you build and deepen a data moat around economically valuable problems that AI can build, better than your competitors?”
We gained cutting edge and applied knowledge in AI Evals—the process, methodology, and tooling around the domain space of
In other words, we learned how AI Bryan could be designed and built to get a virtuous cycle of data.
This can be applied to any LLM based product.
June 2025:
We focused on other pipeline opportunities, and captured the testimonial from the initial work and put it on the back burner for the future.
We started building our muscle on inbound leads.
Good news—we were getting 10 enterprise leads a month (at least it was something!).
Bad news—none of them closed. Dammit.
Learning—most were not qualified leads, and we needed a better demo to spark the imagination from ideal to real.
We needed to get in front of prospects who really feel the pain of not having a solution for hyper-personalized AI experiences.
July 2025:
In parallel with our learnings from stumbling, we realized we needed to balance our efforts with B2B GTM, to de-risk our startup.
To solve this and the demo problem, we decided to create a synergistic B2C offering that uses the AI Personalization tooling and infrastructure we had built. I built the initial alpha version of Clarity, your thinking partner for navigating life’s complexities—an AI that helps you stay aligned with your best self, checks your biases, and maximizes your agency. More on this later.
Things started clicking on the Founder Brand marketing strategy—I just started documenting my user research (street interviews) and creating content out of that with some added flair.
That has been the highest performing content by far, and one of my highest leverage activities for the business.
August 2025:
I gave my notice at Dayforce, and started succession planning. End of year was what I gave the team. For the next few months, I would work night and day to make sure things were transitioned as smoothly as possible, while still making sure we made progress on the startup.
It was a lot.
I also adjusted to having a dog—which was far easier than expected. Having Kenji actually made me even more on top of my time.
Believe it or not, I was even more productive than before. My theory is that having a dog makes you happier so you’re more productive even if you have less time. 🤷
September 2025:
We got connected with Delphi AI, a leading startup building the future of Digital Minds and one of the hottest AI startups having raised $16M from Sequoia Capital. Individuals can create digital AI versions of themselves, called Delphis, by uploading content and/or syncing their social media.
We helped them with a fascinating evals problem: for each individual, how might we get them to their magic moment of seeing themselves in their Delphi? This is the first foundational step in the ladder towards AI hyper-personalization.
We got a reference and testimonial from Sam, CTO and Co-Founder from Delphi.
October 2025:
We started an engagement for a super exciting project with Mystica in the digital tarot reading space, which is incredibly personalization sensitive. I’ll have more to say about this once we finish delivery and see results in Q1.
November 2025:
Heads down.
Building, fulfilling, delivering, executing against the succession plan.
Trying to keep a semblance of balance and control around my health, and dealing with tons of stress from all directions.
December 2025:
I left Dayforce. I signed them as a customer.
And for the remaining weeks of the year I’ve been spending my December prepping my systems for a productive 2026, and spending some time with family.
The Schedule That Built This
Some ask me how I was able to do so much on the side of a demanding executive job.
Really it just comes down to discipline, commitment, and rigorous time management. The boring stuff.
For the past year, my days looked like this most days:
3 AM - 6 AM: Self-care, workout, startup work
6 AM - 2 PM: Chief Product Architect job at Dayforce
2 PM - 4 PM: Climbing/gym/friends (Combining fitness with social time) or more startup work
4 PM - 7 PM: More startup work, more Dayforce work
8 PM: Sleep
At some point along the way this year, I added Kenji dog dad time throughout the day and adapted.
Dayforce was actually perfect because it was on East Coast time.
I got started early, but I got off early—and that allowed me to go to the gym in the middle of the day for a quick break before continuing to work on my startup.
It also helps that I’m a weirdo early bird. Getting up at 3 AM wasn’t too hard of an adjustment, since getting up around 5 has been the norm for a while now.
Some days I would get off work at 2 PM, and run out to find strangers to interview for research and content for a few hours before coming back to update some designs and return communications at Dayforce (or several days a month, run an All Hands).
Some days that would be tracking people down in bookstores for user research tests, for people who fit our ideal customer profile for Clarity.
Some days it was recording the podcast or attending the various meetup events to meet other founders, prospects, users, investors, and more.
Every day this year was extremely different.
It was a lot to juggle.
It was a lot of stress.
At the same time…
It was a lot of fun.
It was a lot of growth.
Building In Public: What We’re Building
We have two main investments right now:
Clarity, your thinking partner for navigating life’s complexities. Aimed at personal growth enthusiasts who see the potential of co-evolving towards your best self with AI, by using it to augment your thinking
Clarity API, a developer focused product that fits into any tech stack easily to enrich and maintain episodic timelines for self-serve rich individualized user context to power your AI product experiences.
It’s interesting to trace the journey of how we got here.
Clarity started with wanting to dog-food our own platform to help with the B2B go-to-market motion. It’s much easier to sell a platform when you see an application successful on the platform. It also forces us to have a higher quality bar. Our feedback loops are much smaller.
That was a great choice.
A few months after making that choice, we found signals of traction on the B2C front. There was a clear acquisition story—any user who fit the Venn diagram of our ideal customer profile wanted to try it.
When we surveyed users, there was a revenue story. People would pay for premium features at certain price points.
After three days of continued usage, users who hit day-three retention wanted to refer their friends and family.
You see, in a startup—especially pre-PMF—you’re trying to run experiments to even see if something is worth investing more in.
To do that, you have to put some skin in the game.
Put some money in, see if you can get money (or signs of traction) out.
Then put more money in.
We’re running our experiments, and I’ll share results as we learn more in Q1.
Clarity, Your Thinking Partner — B2C
I built Clarity for my own problems:
Fragmented journaling
Personality quizzes and tests being static while you’re dynamic
AI that is biased and untrustworthy
Wanting to check my own biases and gain clarity in thought for my decision making
Making sure I’m making progress towards my best self
The type of people it fits: anybody who’s personally growth-minded, into therapy, has been to therapy or would consider it, has journaled, does journal regularly, or has taken personality tests.
Clarity is perfect for the person who is infinitely curious about themselves and the world around them.
The kind of person who wants to take action towards their best self and see that progress daily.
We ran into some technology trouble after initial market validation.
The Hard Part
Some of the metrics were looking good…
But the retention story was pretty fucking awful.
We iterated in Base44 first for the initial product concept.
We gained enough proof that we should migrate it into our own tech stack. That has proven challenging because we’re working as an AI-native startup using new tooling with constantly evolving paradigms and updates.
We’ve had to examine the methodologies working out there and figure out what works well for us—with our skill set, at this point in time, for our startup to gain the most leverage in the direction the business needs us to go.
We’re a software company.
We must be investing into core IP.
We want to align that with the identity we’ve set for ourselves: personalization infrastructure solving AI alignment via hyper-personalization through a neuroscientific and philosophical lens at the intersection of technology.
So we started investing in B2C Clarity rebuilding from scratch on our own tech stack.
That has taken a lot of trials and tribulations to figure out how to protect against regressions on the front end—one of the core issues with Base44.
It couldn’t scale to the requests we asked of the system because of the nature of AI development being non-deterministic.
At some point, if you’re trying to build a business—not just a validated concept—you have to think about controlling all the levers of the system you can so you can dial in the user experience.
And that’s what we decided we wanted after we saw the data points we saw. The evidence was there. There would be demand.
I have high confidence we can achieve the initial goal of getting 100, then 1,000 true fans paying to enjoy Clarity.
More to come on this front. Sign up for the waitlist here.
Clarity API — B2B
At the same time, we invested in parallel into our B2B go-to-market motion.
I can say more in Q1, but right now we’re working on fulfillment and delivery of Clarity API—our B2B product—to help serve the right context at the right time to downstream applications and decision makers around customer and user data.
The API is targeted at use cases where customer data is fragmented and decision makers want unified insight to improve business outcomes.
Clarity API is great for high-personalization, sensitive cases—such as when you’d want to scale high-touch services.
We’re positioning Clarity B2B as a revenue-generating product, meaning our customers—CTOs, CEOs, CCOs, CPOs—could easily see and use our product to generate more revenue.
Better AI Personalization?
Better revenue story.
So now we’re set up in this position where we’re dog-fooding Clarity B2C against Clarity B2B.
They both help grow each other.
Jonathan has handled the migration from the Base44 product concept. I’m going to take that over to focus efforts pushing the application Clarity—to then push the platform Clarity.
It’s an intentional choice so that I dogfood as our ICP AI application developer/PM, and Jonathan takes my requirements to push the platform further.
Fast feedback loops are #1 in my mind right now so we must position to accelerate learning further.
Exactly $0 of our revenue comes from Clarity B2C at the moment.
All of our cash flow, which covers our run rate, is tied to B2B contracts.
However, I’m super wary that cost of acquiring customers with this motion is quite high as it requires very hands on Founder-led sales. So far, it’s taken about 20-60 hours of time to close a customer. I’ll map this out in the future to share how I think more about this.
Looking Back
Looking back, one of the things I’m most grateful for is that I got about 90% of the days to look like the schedule I showed earlier.
Some days I faltered—woke up late at 5:00 or 6:00 AM. (My friends hate me when I say things like this, so please forgive me in advance—this was a real first world problem for me I swear)
Some days I was groggy, and my decision making wasn’t the best.
But most days I came through and put in a productive day’s worth of work on the business and myself.
And that led to one step closer to acquiring the skills I needed to get to this point where I’m fully focused on the startup.
I’m excited now because my schedule looks like this:
3:30-4:00 AM - 9 AM: Self-care, workout, dog dad duties, startup work
9 AM - 4 PM: Startup work, dog dad duties
4 PM - 7 PM: Climbing/gym/friends
4 PM - 7 PM: More startup work, more Dayforce work
7 PM - 8-8:30 PM: Wind down
8:30-9:00 PM: Sleep
Yes, I’m still keeping up with the grind though I’m aiming for a tiny more flexibility in the morning and at night.
I love thinking about the problems that the startup demands. Now I get to spend all my time investing in the business and myself.
We’re a bootstrapped startup. Most businesses fail. Most don’t make a dollar. Most don’t get to profitable.
In reflecting on this year, my mind drifts to a quote I've always loved:
"Luck is when opportunity meets preparation."
You can always increase your surface area of opportunity.
You can always be more prepared.
When I was a kid, I always felt like I was never really talented at anything. But the one thing I had in spades: grit.
I work hard and don't give up easily.
You make your own luck.
So, make your own luck.
What I feel excited about is that I feel like I’ve been playing on hard mode—having to context-switch constantly to juggle demands in my executive role at Dayforce while delivering on the demands of the startup.
Now I get to just fully focus on Clarity? NO context switching across jobs?
LET’S GO.
The Memory That Drives Me
Overall, I’m really excited for this new chapter.
Being in a reflective mood, I can’t help but think back to 2012 when I was a poor, hungry college student dreaming of changing the world.
But before I could get there, I was just making sure I could survive.
I remember when some of my closest family members passed away suddenly within a few months of each other.
My Grandma, Grandpa, and Uncle on my mom’s side.
When I looked at my bank account, I couldn’t afford the plane ticket to fly to Austin to visit their graves and pay them respect.
I always felt like a bad grandson. A bad nephew.
I consoled myself through tough silent tears, telling myself that my family members were survivors too. And they would have understood the need to survive.
Wouldn’t they?
I vowed to myself then—that for me, and anybody I cared about, and the whole world as much as I can:
Everybody should have the chance to become their best selves.
Nobody should have to pick between survival and doing what’s right for them.
Fighting in the war, working manual labor, going through harsh economic times.
My dad became a prisoner of war fighting for his family to have a better life with more opportunity.
All of my family that came before me, had to pick survival.
I now get to pick my best self. I’ll never forget that.
Grandma, Grandpa, Uncle—I won’t let you down.
What’s Next
In the future, I’ll continue to use my newsletter as a place to share and document my journey building my startup dreams in public and becoming my best self along the way.
I’ll continue to deep-dive on the individual front and on the business front. Particularly niche problems like AI development, AI-native development, evals, and more.
And any other skill I have to learn along the way to grow myself into the person I have to become to win with Clarity, solve AI Alignment via Personalization, and help billions of people become their best selves.
Let’s get after it in 2026. 💪
P.S. Want reminders on growth, empathy, and leadership? Follow me on YouTube, LinkedIn, Threads, and Twitter.