30.5 The Hardest 6 Months - Buying A House, Losing My Job (The Same Day), Zero-to-One-ing A New Company, Throwing A Giant Rock Concert, And Definitely Not Imploding

What a ride.

Man, this was supposed to be an easy one.

30 years old so far has been amazing in so many ways, but also tremendously challenging. And it was all my fault.

I’m writing the first draft of this in the middle of a LONG week in early October. There have been about a dozen long weeks preceding this, and I imagine there will be another dozen taking me to Christmas (there were), where I would gladly take coal if it means a brief respite.

This is going to be more of a story than a reflection, and I think it’s a long one at that.

I’m starting writing this now because this is what I have to imagine is the low before the high.

I’m not one to complain about putting myself in situations worth complaining about (*checks notes* yes I am), but wow (see below).

Happy Birthday Jack

I rang in 30 with a birthday party that almost killed me. No, I didn’t almost die, but it felt like I could have.

I was working full time on growth at a Seed stage startup, hammering out the beginnings of an enterprise customer contract for a company I was starting on the side, and planning a 4 band, 100 person night of rock n roll and celebration.

I gave every last bit of myself to these things.

The day of the party I woke up in a full panic attack (numbness, dizziness, pounding heart, confusion). As people started showing up, I hoped it would subside, but it didn’t. I felt awful the whole time.

I remember wishing that I could switch off and teleport to the next day.

I felt completely overwhelmed by the prospect of showing up, smiling for 100 people, running logistics for all the bands and the sound guy, and playing a full hour of rock n roll as the night cap.

Despite how I felt, months of planning, practice, and coordination made the party a smash hit. 100 people did attend. 4 bands did play. My band, Catnip, headlined, and we shut the place down.

It was so much fun.

I wish I had been there for it instead of on catatonic autopilot, but the amount of gratitude I experienced did sink in.

I won’t harp on it too much as I already harped on it in my turning 30 post, but I’ll say this. I’m someone who is naturally convinced that everyone secretly dislikes him. Maybe this is inconceivable, or maybe I’m right and you’re nodding in agreement right now. Having 100 people come for ME and seemingly WANT to be there suggested an alternative hypothesis. That hypothesis has NOT sunk in yet, but maybe one day.

As soon as the party was over, I had this big catharsis, but I also felt like something changed. More on that later.

I officially started building that second company in probably like March, but I began stressing about building that second company in like December of last year. Not to mention I was worried about my current company firing me for working on two things. And P.S.S. there is also the measuring contest that inevitably occurs when you enter back into the founder arena with a bunch of other high ambition people.

So yeah, July, party’s over, I’m 30 now, finally I get to go back to just having 2 stressful things instead of 3. Time to chill.

Venture Capital

Enter VC.

VC contacted my brother, whose resume reflects his ability way more than my scattered one. Chip on my shoulder, is that you?

I’ve started multiple companies before, but without elaborating too much, I didn’t fail upward or really even have much to show for them.

This has, not colloquially, been the story of my life. Lots of talent and ambition, but some missing ingredient that causes literally everyone who doesn’t intimately know me to overlook me - are you nodding right now?

We shut down the last company (which was actually not un-successful given the market we got sort of red-pilled into chasing—VR WEB3 METAVERSE in 2020 LOL), and I basically looked like a guy who was just “playing founder”.

Idk. Whatever. Doesn’t matter. I feel overlooked, okay.

So VC contacts my brother because he’d been at FAANG before and is currently at a company that is the having their hot girl moment.

We meet with VC, and they want to invest in the new company. Cool cool, but there’s a catch.

1. We need to quit our jobs at some point

2. We can’t pay ourselves more than like $90k if we take the money

We also ended up getting terms from the enterprise CEO that same week:

1. He wanted to invest in the company at whatever valuation the VC got in at.

So 3 horcruxes:

Enterprise

We dealt with the enterprise thing by agreeing that whatever the first investment check values our company at, he’d be able to invest at.

So easy. Definitely not going to regret that ✅

Job quitting

On the quitting our jobs side, I was okay with walking away from my job. We gave it everything at the company for 2 years and it seemed like the market just didn’t want the product. It worked out for me though. I got a full crash course in both MBA-style B2B SaaS as well as product marketing, and I got to do it on a real salary. In this role, I felt like I finally arrived in the Silicon Valley as a contributor and not just an overpaid worker bee.

Very grateful.

My brother was a different story.

When you’re on a rocket ship, you don’t get off. That’s being a guy 101. We’ve all seen Jimmy Neutron. That scene where they leave earth to rescue their parents with “Kids In America” blasting. That is good stuff man. We had the best agitprop back in the day. Wow. As a boy genius, that might have been my brother’s favorite movie, so yeah, he wasn’t leaving until we had real revenue.

To justify to the reader that we aren’t soft, we had previously quit our jobs with 0 revenue building aforementioned VR WEB3 METAVERSE only to ruin our self esteems for $70k/year in San Francisco, so this time we’d avoid that mistake. We decided that if we could ink that $20k/mo deal with the enterprise company and get a few more customers in the pipeline, that would be enough for my brother to leave his job.

Low SF Salary + A House?

On the $90k side, this would complicate some long term plans, but we devised a plan!(!)

We’d been super interested in buying a duplex to start building some house equity. You can’t get a loan to buy a $2MM duplex on two $90k pre-seed salaries (you need a stable income), but you can pay a mortgage on that.

If we could buy a duplex in 1 month (yes, 1 month) and get to revenue in 2 months, then in 3 months we could quit our jobs, with a house, and healthy runway.

It was fool proof. Or maybe it was proof that we were fools. But we are men of action, so we got to work.

My CEO at the time has a dad (uh huh). His dad is a real estate agent. I texted his dad on August 1. By August 5 we’d found a property, but had been assured that because it was such a good deal in such a good location, a developer would come in and scoop it up 100%. It was also owned by someone who died, so there were no records on it (also why it was such a good deal).

We knew we weren’t gonna get it, so we figured there was nothing to lose by getting a rep in. We made an offer on Friday. Real men of action stuff.

The selling agent said he wanted to wait until Monday afternoon to pick who would get it.

Sunday the agent was showing the property, so I did what anyone would do. I showed up with the world’s tiniest violin.

“It would be such a great place for my brother and I to start our respective families”. I’m a musician and heart strings are one of the instruments I’m most proficient at.

I wasn’t lying about the family stuff, but the big bad capitalism devil that is the developer can’t play heart strings, so I really played my angle.

That night there were some grumbles that the market in Japan was going crazy. Speculation that BLACK MONDAY was awaiting us when the markets opened on Monday took Twitter by storm. Crypto markets crashed. I had already sold a bunch to prepare for a pre-approval that came in Friday night. My brother still had to sell some. RIP.

But this created a new dynamic. If everyone was worried about the markets, would we be getting this house?

Monday came and went, and sure enough, there were no competitive offers. Do we own a duplex now?

Yes.

Well sort of.

A day later we’re told that we need to lock in insurance which is usually no big deal.

Usually.

Actually, huge deal. Because California is such a great place, it’s really easy to get insurance. No, that’s actually 100% the opposite of the truth.

Pair this with the house being sold with no information (thus making it even harder to get insurance), and we had the most acute stress I’ve ever experienced as I was rejected by every single insurer in San Francisco.

We’re gonna lose this house.

Over the next 24 hrs I had fully come to terms with remaining a loser (a renter) (that’s a joke), but then I got a text from my brother early the next day. Some guy named AK out of the Central Valley would insure the house. I would die for this man.

We got the house.

Closing was stressful, but after that one week rollercoaster I was prepared for anything. Well, almost anything.

We signed our closing paperwork on August 30th at 10am. On August 30th at 12:13pm the CEO of the company I was daylighting at announced that the company would be shutting down.

Guess that handles me leaving my job.

After reading a bunch of Russian Novels in 2023, I reconnected a bit with my Catholicism, but this made me a full believer. Jesus Christ I love you and I’m sorry about the rock n roll. You give your hardest battles to your somewhat least deserving, sort of strong-ish soldiers.’

If the company had closed at 9:13am, I’d be legally obligated to tell the lender, threatening the whole deal, but 12:13pm? I didn’t have to tell them shit.

The Tweet Heard Around The World Twitter

It was moving day. Knowing I needed to convince VC that writing a check right now was a good idea without letting up that I needed the money, I felt like I should drum up some excitement around the company.

Game theory 101 for anyone paying attention at home.

I tweeted about how good our tech was, and a recent conversation with an AI girlfriend app who tried our product and was blown away by how fast and cheap it is. I also threw in that we’re bootstrapped just to add some pizzaz and dunk on the losers who had raised VC money (we were raising VC money).

I hit send and started moving into the new house.

I checked twitter an hour later. 10,000 views and my DMs were full.

Look, I’m not a sardonic dunk boy, nor am I a cute tech girl, so 6 likes is my CEILING.

Turns out there is huge demand for real-time AI simulated communication among a ton of consumer apps. Toys, companions, porn, hardware. Am *I* the hot girl at prom now? I didn’t have any testosterone at 16, and therefore didn’t go to prom, but I imagine this is what it would have been like to hit puberty on time.

I gave all these people my Calendly link and continued moving.

What I failed to realized was that it was a 3 day weekend, and not only was that not marked on my Calendly, but I also had my first available meeting slot for 7am on Monday.

Oh my god.

After 3 days of 8am-10pm moving, I had to wake up at 5:30am on Labor Day morning to take calls. We didn’t have internet in the new place yet, so I would go to the office.

I got to the office, ready to buckle down for 6 hours of calls, and…the door was locked. The office is in a federal building.

Oh my god again.

I start walking to Starbucks, praying they’d be open. When I got there, kismet would have it that the building manager for the office was there too and he helped me get into the office.

I’m legitimately going to start going to church.

This week was basically non-stop calls with investors, customers, other founders. It was great. And it all got rounded out with the VC who had wanted to write a check walking away from the deal.

Wait.

Walking away from the deal!? That’s not a happy ending.

Correct, stressful ending.

90k/yr? How about $0k/yr?

The Hard Part

At this point, I had probably $40k of pipeline with a $0 salary, a fat mortgage, a brother who is working a hard job and not able to put much time into the company. What am I supposed to do?

Well, what I didn’t do was panic, and this takes me to the self-reflection part of this story

I was looking down the barrel of the the hardest month of my life on the heels of the hardest month of my life.

I don’t know how, but I found zen during this time.

Do not get me wrong, this was hard. Probably the most stress ever recorded in human history (kind of a lot), for the longest amount of time (a couple months). Ok, on an absolute scale this was really awful/10, but on a relative scale? Dog shit/10.

Huge shout out to Abhishek, Jan, David, Miles, Kartik, Evan, Matt, Ryan, Dan, and a few other people I’m probably forgetting. They all reminded me that not only was this a dream scenario for many founders, but that if anyone could make lemonade it was me, a guy who is only lukewarm to lemonade (more of a gatorade guy).

F*** yeah, let’s cook.

I networked, I kept doing GTM and got even more pipeline, I dusted off the cobwebs and started writing code 50 hrs a week again (I was doing hard 70-80 hr weeks at this point).

Various customers needed various things, and I would basically wake up at 6, go to the gym, wimp out on talking to my gym crush (I did eventually talk to her, I think she has a bf?), then I’d work until 8 or 9 (or 10 or 11…). If I was lucky, I’d play some guitar, but I was rarely lucky.

These were the longest days I’ve worked, and they literally kept stacking and stacking. I went from wishing I could watch 10 minutes of YouTube to forgetting YouTube exists.

Last time this happened, I got severe alopecia and basically imploded. This time, I was more resilient.

I still have no head hair, so that was handled. I resolved that as long as I didn’t lose my eyebrows, I had nothing to lose by grinding myself to a pulp.

We got a message from the enterprise CEO out of the blue. They wanted to move faster, and they wanted us to not just provide the backend for their product (our product as is), but instead we should *waves hands* build their whole product for them. All of this was great, except I had just gotten 15 new companies in our funnel and I was fully extended. And they wanted it in a week and a half. Neil, my still employed co-founder was leaving for Japan for 10 days in 2 weeks.

Okay, time to prioritize and disappoint some people.

Product, engineering, customer success, sales, and marketing all day every day. The work quality started to go down, but I didn’t have a choice.

I showed up every day for months and I worked.

I got pretty sick for 2 weeks, but didn’t slow down. My shoulder stopped working (medical mystery, doctors couldn’t explain, it randomly started working again), didn’t slow down. The week my brother was in Japan, I told myself I’d slow down, I didn’t slow down. The product went down one day and I couldn’t fix it without my brother, so I would have to wait until 3pm when he woke up in Japan. That night, I woke up at 3am to my heart racing & full 16 beer vertigo (I was sober). I vomited, drank some water, and went back to bed. I didn’t slow down.

Even if I couldn’t hit the gas any harder, the goal was to stay off the brakes.

I felt like someone wiped away all of the indulgences I once needed. No fun. No games. No bikes. No rock n roll (except for an outing for a friend to play on Halloween). I literally couldn’t feel things anymore. I’ve been horribly, keep-an-eye-on-this-guy depressed a few times in life, but this was different. This was not about me. This was, and it sounds ridiculous, more about survival.

I do have a small safety net from my parents/grandpa buying their houses in the bay area decades ago and a decent enough nest egg from 9 years of neurotic ETF investing, but to me going backwards or asking for help from people with no skin in my game is non-negotiable. I don’t even like standing still, let alone regressing.

I would not quit.

The Bite In The Ass

I worked and worked, and eventually decided to raise a small bit of money from the incubator that took a chance on me last time around when I wasn’t anything special. I wanted to work with them again, and I am big on paying back in multiples.

Incubator can’t do big valuations, which would be fine, except we had an investment deal with that enterprise customer.

The one that said they can invest $100k at the best valuation we get. The one that now said they could buy a HUGE chunk of the company for $100k.

This would have been the most stressful thing ever if I didn’t have the 3 other most stressful things ever happening at the same time.

I would need to convince this enterprise CEO not to go with the initial investment agreement. He had a royal flush, and I was convincing him that we should stop playing the game after we had already showed our hands. I deliberated how to do this for a few days before just being honest.

This whole thing was another 2 months of stress and back and forth, evolving into new, left-field proposals and negotiations that are not worth fully explaining. The tl;dr is they wanted a bunch of things that made sense in a vacuum, but compromised my company’s ability to fundraise/operate/exist into the future. It only cost me $35,000 in legal fees to resolve and 100+ hrs of emails and Sunday calls with the CEO (and stress). Literally not a single part of this went smoothly.

I was so stressed that I got sick again, this time for something like a month. Every time I’d start to feel better, I’d get some gut punch email that would turn a 10 hr day into a 14 hr day where I’d zombie my way through whatever work needed to be done, quadruple checking everything because my brain was mush, ending up sick again.

We brought on a co-founder to own GTM while I bounced between Customer Success, Engineering, Hiring, Contracts, Fundraising, and still a decent amount of GTM.

This offloaded a bit of the stress of me not having time to go get customers, but the existential stress of not existing in 4 months persisted.

We got a super lucky chance to hire a physics olympiad turned AI engineer to bring a lot of our AI in-house…and then he ghosted us. But the idea was planted. We’d bring the whole AI stack in house, meaning we could dramatically lower prices, opening a new market of customers who were priced out of the existing market.

I decided (my stress decided) it was time to raise a seed round. I had a mortgage, and thanks to the enterprise contract legal fees, 2 months less of runway to pay the team with (I had not paid myself up to this point—was burning savings for previous 3 months).

I made a tweet announcing we were raising and a good friend Jan saw the tweet and tagged a guy. We chatted with the guy and he said it was one of the best pitches of the year.

The guy knows everyone, so 2 days later we’re talking to Andreessen Horowitz, the biggest VC firm in the world.

Before the A16z pitch, we were to speak with a smaller VC after coming to their hacker-house for dinner to talk partnerships with one of their companies. The VC we talked to was tired after a long day of calls, so instead of a fun conversations, we got grilled.

That was the day between the talk with the guy and the A16z talk, so we used this grilling to tighten up the pitch. In parallel, Brian, the new co-founder, was having magic moments left and right when trying the parts of the product.

It was all coming together.

He convinced me that a demo where the VC can talk to themself would be insane. I built that and the pitch with A16z went about as well as it could.

“Very impressive”. “You guys are cooking”. “More progress than we’ve ever seen from a company so young.”

I left that call feeling so validated after spending the weeks leading up unsure what my life would amount to if I couldn’t pull this off. (I’m literally writing this part of the story an hour after this part of the story, so I don’t know what happened yet).

(Now I’m writing this a week later)

I had another friend offer a similar thing, so now we had a bunch of warm intros from the guy and my friend.

We ended up pitching something like 7-8 VCs that week.

Because none of our customers had gone live yet, we didn’t get a single yes. We got one “talk to us when you hit 5 figures monthly revenue”, a few “I don’t know about this market”, 3 “please call during Series A”, and then the rest ghosted us.

Momentum gone.

This became the new stressor while the contract was happening in the background. I needed 1 year of runway before I could feel safe pursuing literally anything else.

This was weird though, because the business was seemingly working judging by the funnel and interest (we were early in a new market), but the VCs made us second guess ourselves. Part of me thought to ignore it and keep building the business, but part of me couldn’t help but listen.

The job of a VC is to spend 6 months a year vacationing (kidding!) and the other 6 months deciding if ideas have 10-100x potential. i.e. they decide if you’re building a big business based on evidence you present.

So I was either

1. not presenting the right evidence

2. showing evidence that suggested we were not on the right track

We assumed both were true.

1. Pitch needs tightening. i.e. we need to figure out who we are. This led to great planning talks and us really defining our segment, messaging, and roadmap

2. We needed to prove it by getting pipeline and establishing ourselves

Now yes, this was a Seed round we were asking for, and we had mostly just talked to top VCs, flaunting a not-that-impressive bit of revenue, a handful customers, and a healthy pipeline, but I wanted to be a top company, so those 7 No’s were enough for me to decide I needed to be better.

No more pitching—we’re going to become undeniable.

That week l finished Endurance, a book about getting kicked over and over again in increasingly dire circumstances and continuing to march on. I literally cried a little as it ended because in many ways it felt like a book about me during this chapter of my life.

A Light

The happy ending here is more of a light at the end off the tunnel.

Neil, my CTO, and partner through 90% of this story was still working. Working 2 jobs is a battle in and of itself, so no fault to him, but this put most of the pressure to move the company forward on me, and having been living on savings this whole time, it was war on 2 fronts. The week before Thanksgiving was FINALLY his last week working.

Brian came to town that week, and not only did I finally feel like I could shed some of the increasingly heavy load I’d been shouldering, but I finally had more minds thinking about product, networking, and pushing the ball forward.

We had some amazing chats that belong in a novel. Famous Menlo Park bar with well connected industry veteran who validates we’re doing the right thing over a beer in a corner booth, phone calls where we closed customers from my dingy top floor unit, pitches with firms I could only have dreamed of talking to a few years earlier.

We had the same problems, but my perspective on them was now one of adventure rather than subjugation.

The happy ending here is that week before Thanksgiving we finally got some good news. The contract was getting signed. If what the CEO of the enterprise company had said was true, this should equate to something like 5 figures/month once they were spooled up, meaning financial pressure would ease up.

We got an acquisition offer right before our hockey stick moment that I was so fried for I didn’t realize was an acquisition until my brother told me after. (We didn’t want it, but was validating.)

We kept working and working, and eventually things started to fall into place.

Customers started going live. Conversations turned into more conversations, growth/product ideas became reality became more revenue.

I’m writing this last part the most tired I’ve been, but also the most invigorated. Betting on yourself for 10 years is worth it. Progress will be slow and painful, but once you know what picture the puzzle makes, it gets easier to start placing pieces.

We’ve still got a month or so to fully realize our vision, two if I’m being realistic, but we have a vision, and if we pull it off, we change the way people build and interact with AI apps, and that’s easy to feel confident about.

So what did I learn?

Well I’ll start at the beginning now that I’ve fully forgotten about that.

I started really becoming a man in the traditional, I-do-not-care-about-most-trivial-things-anymore sense at maybe 28 when we shut down the last company, but I hit the first milestone on that 30th birthday night. It was such a crazy catharsis after such an acute stress that my brain emerged different.

I remember the night ended, all 100 people were drunk and happy, and I felt alone.

Something had changed.

This wasn’t one of those epiphanies that you have when reading an inspirational quote that you forget as soon as you close Instagram.

This one stuck.

I was still with friends, socializing at a bar, but I felt like I was an imposter being there. I’ve often felt this way in ebbs and flows, and maybe I’m just depressed, but again, this felt different.

When I was really depressed, I felt like I didn’t belong anywhere. When I was mentally well but unfulfilled, I felt like there was “more” I could be doing, but that “more” was unclear.

But this time I feel like the “more” is clear.

I have a company that is on it’s way to ripping, a rock band that produces the kind of music I’ve dreamed of making (and enables me to sing and dance for 100 people at a time), and a life full of things I used to dream about.

Hard work, humility (not pride), curiosity, forgiveness, gratitude, and perseverance (a LOT of that last one) yield results, and while I’ve always known this, now it’s wisdom because it’s become true for me on the macro.

I’ve missed out on a lot of hedonism over the years, and I used to spend a good amount of time moping, but with clear goals, there’s no time for those things.

Maybe doing everything you set out to do in life isn’t your priority (which is fine), but if it is, go pick the hardest problem you can find and work at it until you forget your old life.

At 22, I thought work was the end of my life. At 30, I’m confident it’s the point (with the right definition).

How you decide to make the most of life is up to you, but I have tried everything, and making stuff that aligns with my competencies is so far the best I’ve found.

So no, working a soul sucking job isn’t the point of life, but finding the things YOU should be doing and going all in on those - yeah, that’s the stuff right there.

I always wanted to become a Youtuber/influencer. I’ve tried my hand at it a few times, but I have a bit too much shame, and I’m a bit too chaotic for it to really work.

What I’ve done instead is find the things that align with who I am and leaned into those.

Writing songs, singing, bringing the energy. These are all trivial to me. I can’t not do them.

Building stuff, organizing people around goals, pushing that goal forward, doing things my way. They are compulsions.

I’m very satisfied with those being my life’s purpose. It took me a long time to commit to them (I’ve always known these are my things), and it took a lot of willpower to ignore the wisdom of the crowd, but I work more than I ever have, and it mostly feels like there’s no other way I can even conceive of spending my time. It’s like eating or sleeping. It’s a need at a base level.

Manhood

On manhood, I thought it would be different.

That socially lubricated 6 beer swagger that I’ve had glimpses of when the stars align on a Friday night. That’s what I thought being a man would be. That’s not being a man, that’s just being drunk.

The subjective experience is something different and constant. I’m not necessarily more confident, but I’m more unflappable I guess?

I still feel insecure or awkward at times, but EVERYTHING rolls off my back.

I’ve talked about bucking up and refining who you are and believing in your ideas, and now I guess I’m acting on all that. I can bite off more than I can chew and clean up whatever mess is in front of me without needing to complain about it to my brother an hour later.

I can commit to something and see it through til it’s done, not til I’m done. I don’t even think about me anymore.

I have a good memory, so maybe this is the normal male arch and I’m not supposed to remember how emotional I was in my 20s, but it is weird right?

The emotionality is gone.

I don’t think it’s because I’m burned out either. Yes, my brain is overclocked all day every day, but that used to lead to anxiety, and now it yields zen—I do think literally all the time, but I don’t lose sleep over things anymore.

It’s odd.

I also had to figure out who I am again. Authenticity is something I’ve really paid attention to these last 4-5 years, and I think there are levels to it. There’s first realizing you’re acting like someone else, then there’s trying to find out who you are, and then there’s this third, less obvious one of forgetting all that stuff and just being.

I remember losing sleep over deciding if I should be thoughtful and serious or charismatic and relatable. I even probed my buddy Evan about it on a trip we took. Would customers/investors expect serious? What about the cute girl at the bus stop?

Then I recorded a podcast, thought I bombed, only to listen back and realize I was both.

Then I watched my parents dog play with my brother’s girlfriend's cat, and realized we’re the only animals that spend time thinking about how we are instead of just being.

So yeah, I think I need to stop thinking about myself, which many psychologists agree is indistinguishable from mental health problems. Less thinking, more living.

On the business side, I didn’t learn much, but rather reinforced some obvious things.

For starters, shipping a minimum viable product that isn’t actually valuable to anyone is good for demos but bad for customers who want to move fast. A lot of features were missing when we initially took the product to market, and while it took customer feedback to refine those features, we still could have done more upfront.

Another thing. Be more aggressive when things are good, and don’t go looking for a kick when you’re already down.

Not that I had much time over the past 6 months to do more, but there were moments I could have pushed more, and there were also many more moments where I could have afforded to give myself a break. I loved the idea of having 20 customers, but we couldn’t handle 20 customers. That was foolish.

However the biggest thing I learned is when the universe gives you an at bat, you swing as hard as you can.

The path of least regret

I don’t regret any of this because I knew I’d regret it more if I didn’t do all of this. I have had pretty much every role in tech, I’ve started companies, and I was getting a chance to put all that past experience to use to see what I’m made of.

There are ways to live life. Over these last 6 months I felt the most alive I ever have. I was in the cockpit on life, and sure I skipped the Intro To Flying class, but I’d land the plane or die trying.

I was rundown and felt awful the whole time, but I look back with fondness, because the alternative, the coming home from a somewhat fulfilling job and having a beer and lying on the couch, unsure of where I’m going, sounds like death to me.

I’m not sure if I’ll ever have to go through something quite this difficult again—mostly because I can’t imagine a scenario where that’s even possible—so I’m basking in the pain for as long as I can. Time in pain = growth.

I’ve had a chance to write some new music that is all over the map, so going to start putting that out early this year, but otherwise, I’m hoping to slow down soon.

I’m very lonely, spending most of my time working or sitting in the house I own with my guitar staring at the walls. I used to abhor alone time because my thoughts were always so bad. Then I came to love it because it was the best way to face my demons. Now I don’t have any demons left but I miss them because they kept me company.

I have Neil and his girlfriend to hang out with, but obviously having a full time lady is different.

We’ll need to fix that problem soon. I do worry if I find someone now I’ll be incompatible with them in a year, but I don’t want to waste more brainpower on it even though I definitely will.

This is a weird place to end one of these because this story is only halfway o

ver, but it’s shaping up to be a good one.

Thanks for reading, and I’m hoping to have some good news to report back 6 months from now on my 31st.

Jack