#1: What happens when you don't die

En media res.

I learned a few years ago that that means being dropped in the middle of the story. But when you put it in Latin everyone knows it’s legit.

That’s what we’re gonna do with this newsletter. This is the first issue, and I’m gonna start out talking about this week. There’s a whole story to how we got where we are today. You can find some pieces of it around the web and in some books and articles I’ve written about Crash and the previous company I built, Praxis (well, technically the same company, but that’s another story we’ll skip for now).

I want to begin in real time with what I’m currently doing, not told as history. When told as history, it tends to get rosier, clearer, or more poignant than it actually was. We humans can’t help but rewrite our own pasts. That’s largely a good thing, but I want to see what it’s like to tell it live.

I’m sure as I write these each week there will be back-filling of some history bits, but we’ll let that shake out whenever it does. You can ask me stuff you want to know as well, and I’ll try to work it in.

So what happened this week?

I raised some money. That felt very good. August has been hard.

I only decided for sure to raise another round of capital at the beginning of this month, but I spent most of July taking investor meetings (I was in San Francisco for the summer and tried to take advantage of face to face) to explore whether I should, how much to raise, etc. Get my early reps in before it got real.

Raising money is bad for my mental health.

Not so much the stress, but more its propensity to warp my worldview on my own company.

I pulled together a narrative about Crash, framed up by a pitch deck, and got started. All felt very good and clear and made me proud of what we’re building. The longer fundraising goes, the more people I talk to, two things start to break up this tight narrative:

1. Investors poke holes in it.

2. It slowly gets less true each week our team, product, customers, and direction adjusts.

So I can start to feel like I’m dragging around this half-zombie narrative, looking at it unsure whether I still think it’s true, but at the same time feeling like I don’t have enough time to start from scratch and construct a new one before my 15 calls this week with investors, let alone whip back around to earlier investors and say “What I said last week about our strategy is actually not quite right.”

I can start to feel impostor syndrome. And there’s nothing more wounding to my personal pride than the idea that I’m not really creating value but just puffing up about it to swindle people out of money. If I felt that was really true, I’d quit. The way to get clarity about whether or not the decreasingly tight narrative is still true enough to plow forward is usually to reflect on my past for a minute, then tell the truth about the future. If I think about the present, it’s too hard to know exactly what’s going on and evidence can be contradictory.

When I say think about the past, I have to remind myself where I came from. Six years ago when I pitched him the idea for Praxis, my friend David Kirby asked, “Are you looking to raise VC?” I asked what VC stood for.

In other words, I knew nothing. I had a deep burning passion to build something. Every one of my narratives about the process and plan and team and growth ended up changing beyond recognition. And we built something anyway and that led to this.

When I say think about the future, I ask myself what I’m trying to create and whether or not I will live and breath the journey there every day and whether I believe it can be epic. The answer for me is always yes (if I extend my time horizon long enough.:-)

So that calms me and my shaky narrative about the present. Not because it makes me feel more correct, but because it makes me feel more comfortable with the growing probability that I am incorrect.

Still, I was able to get about half of the money we’re raising for this round committed. It was a boost, but it dramatically ups the ante as well. This is the second round in a year that we’re raising “pre-product market fit”, which is a fancy way of saying we’re raising on the vision, market opportunity, and team. Which also means we’re not raising on the tangible traction we’ve achieved in users or revenue. Which means my plan to use the first investment last year to quickly get the product live, grow it, and raise a huge Series A based on explosive growth 18 months later is not happening.

That’s a hard pill to swallow. In perspective, it’s not too abnormal. We went from an idea to a team to a product to early customers and customer outcomes in a year. Sounds good when I put it that way. But it felt like cringey misstep after cringey misstep.

It’s so different from what I thought, planned, and pitched. Yes, I know investors know they’re taking a chance. But I’m an old school kid from the Midwest. I always, always feel a relentless pressure to create a massive win for my investors who took a chance on me, and I feel the constant, subtle, looming reaper of failure over my shoulder. When I look an investor in the eye and say, “Bet on me” and they do, I’ll be damned if I’m gonna fail to live up to that. Again, my investors are pros. They are not putting that pressure on me. Somehow, I can’t help but put it on myself.

Not to get too psycho-analytical here, but I wonder sometimes if it’s a proxy for making my dad proud. He was in a car accident when I as 3 and spent his remaining life confined to a wheelchair with a closed head injury and no short term memory. I don’t think about it much because it’s always been normal, but at a few moments in life someone has told me, “Your dad would be proud of you” and I broke down. It hit me in a way that surprised me. So when an older dude I respect bets on my company, my desire to get them a win goes a little deeper I suspect than just keeping my end of a business deal. (Of course, this is in combat with another overriding feeling I have had my whole life, which is a dislike for mentors and disdain for anyone or anything that feels like it is hampering my freedom).

And that’s one example of the true nature of startups. It’s like a J.J. Abrams movie. You think it’s about the monster or time portal, but really it’s about daddy issues or some internal conflict.

It’s a mental, emotional, spiritual activity. Every problem with the company is really a problem with me or the team at some point. (Wow, reading that is a little scary!) Companies don’t exist independent of people.

Back to this week

Anyway, I flew back from San Francisco over the weekend, got stranded in the Charlotte airport overnight, and spent Saturday half-sleeping. Sunday I wanted to unwind and prep for a jam-packed week of fundraising calls.

Then Sunday night my closest friend and colleague texted. A dear childhood friend died in tragic circumstances. We met up and talked and walked late into the night. I was good, and a reminder of what really matters.

Of course it threw a wrench in my Monday plans as far as starting fresh and early. But if I’m honest I kind of liked it because I got to feel like my fatigue was the result of doing something more important than startups the night before, and gave me a little moral/mental edge in my calls. Yeah, I told you, it’s all a mental game.

Monday was brutal though, mostly because of a misunderstanding where I thought one of our investors from the last round was sitting this one out, which is a negative signal to other investors. On Tuesday we talked an it turned out I had misinterpreted in his text message what he meant by “help with this round”. That was a game-changer. I needed a win and it set a fire. It helped me get one more funding commitment the next day and narrow my prospect list, as well as revisit a few cold leads.

The rest of this week has been a literal daily roller-coaster. Every other day has felt great, like we’re making a world-beating company, followed by a brutal day where it seems we have so much to figure out and only a vague idea where to start. I try to tell myself that both are true, which seems sort of probable and it helps me stay focused.

Oh, the almost dead part

The subject of this newsletter. Yes, I aid August was hard. Part of the reason is because I spent most of it sleeping less than 4 hours a night, having hot flashes, extreme chaotic mental energy and anxiety, raspy, swollen throat, chest and lung pain, and a rapid heart beat. I lost 15 pounds. (And I am not a guy who should lose 15 pounds). Finally, on a trip to Utah to speak at a conference, I ended up in the ER, sweating with a heartrate of 130bpm.

The good news is I didn’t die.

The better news is it doesn’t look chronic or permanent and it’s treatable.

The bad news is my thyroid hates me.

Apparently, most likely caused by a viral infection, my thyroid started cranking out hormones that act kind of like crack. I was shaky and “up” all the time for over a month. It got bad enough for the ER, but now I’m on meds that are bringing it down and it should gradually subside over the next month.

So not dying was a big deal. It, too, helped provide much needed perspective. Once I started feeling more normal the last few weeks, I got super happy too. I remembered for the first time in a while how fun all of this is.

Yes, it’s a mental grind. But damn, if I zoom out (and stop worrying about what would happen if we fail), it’s really fucking fun to be in these trenches. (Sorry for the F-bomb mother. I know you’re reading this.)

OK, there’s issue #1

I’ve got no idea how these will shake out each week. The style, format, length, and content are all going to evolve.

I ask one favor: If you didn’t like this one, give me like three more tries and let’s see what happens. I never go in to content creation with a plan. I just start making it. I find that getting live reps in is the best way to help something good emerge.

Oh, and feedback.

I do not normally solicit feedback or read comments on stuff I write. But part of the reason I gated this newsletter with monthly charge is so that I can. If you’re willing to spend a few bucks just to read this, I want to know questions or ideas you have.

So let me know if there’s something you want me to discuss. I’ll share pitch decks or my strategy for fundraising if you like. Or more background. Or what I ate for breakfast. Or how I deal with whatever. Just let me know.

Otherwise, I’m going to follow the words of Hemingway every Friday morning and sit down and write the truest sentence I know. Followed by the next.

Thanks,

Isaac