On entrepreneurship, panic attacks, and lightning bolts

We weren't out of the woods, but at least I was out of the corn.

Happy 4th of July! I appreciate you spending a few minutes of your holiday reading my work. I hope it’s a worthwhile escape.

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As the panic attack subsided, I realized I was squatting in a cornfield I didn’t remember walking into. I looked around and said aloud—before a new panic had time to take hold—Turn around, walk straight back, and hope that leads you out. Before this day was over, I’d be in tears again 180 miles away. Then I’d order a glass of champagne. All of which would be fitting considering the journey I was on.

Make no mistake: entrepreneurship is not a job, or a career, it’s a crucible. Anything that doesn’t fit a little doesn’t fit at all and is squeezed out, including every emotion between abject terror and elation. My day—from panic attack to celebration—was evidence of this, was evidence of how the entrepreneurial journey I’d embarked on had ripped out the emotional dial of my life and replaced it with a switch.

Let’s go back.

Six months ago, I’d lost a huge customer because I couldn’t scale my little training company to their global needs, and so had hired a software development firm to build a tool for me so I wouldn’t miss that opportunity a second time. This was back in 2013 when building software required more than a vibe coding tool account and a budget for AI tokens.

Four months ago, the HR Technology Conference leadership had reached out to say they’d seen the software and wanted to feature us as part of their inaugural “Awesome New Startups” showcase; and I’d said “Yes” and promised we’d have a buyable, enterprise-grade version of our tech ready by the fall conference.

Three months ago, I’d started negotiating with LinkedIn about running the TalentConnect Rock Your Profile booth, which I’d run for the last two years.

Two months ago, my team revolted. Lisa, my partner, called me out for not moving fast enough to convert from a consulting firm to a software company as I’d promised… and quit.

Last month, I’d realized that my TalentConnect contract was a trap; supporting it precluded me from adequately investing in software development to make the transition. I’d lost a customer and now my team, and for what? For business I didn’t want. I fired LinkedIn as a client, doubled down on my investment in the existing software platform to get it ready for HRTech, and hired DeveloperTown to serve as sort of a technical cofounder and help us plan version 2.0 of this tool “the right way.”

I told Lisa what I’d done and convinced her to come back.

Yesterday, joined by Ben, a Northwestern grad and the one other person to make the leap from the consulting firm to the software company with us, we had met at DeveloperTown’s offices in Indianapolis to onboard them. I figured the timing was perfect: we could get them under the hood on our v1.0 product and work with them on the HRTech launch, which would give them a natural onboarding ramp. Our marketing materials would, in essence, be our product roadmap, which they’d be positioned to take over in the fall. The day went great.

Now we sat in the DT’s conference room, gearing up to start day two of two. Mike had barely begun outlining the agenda for the day when my email chirped to announce a note from the current developer, letting me know they’d hit a snag and that they’d miss our schedule for being ready for the conference. They were taking full accountability for the delay, they felt horrible, they wanted to know how to make it right. Which, on most days, would have triggered a firm but compassionate response from me.

But this was not most days.

Barely 15 minutes before their email arrived, I’d fielded a phone call from the chair of the HRTech conference, looking to confirm with me that our software would be ready before the press release announcing our inclusion went out. I’d confirmed and the press release went out just a few minutes later. The conference attracted nearly ten thousand attendees; I didn’t want to think about the size of the email distribution list. The developer knew all this; I had only made these commitments based on their assurances… and now our launch was a matter of public record.

I had to fire them.

“Mike?” I said. “I’d like to call an audible for today. I think I need you to take over development of 1.0.”

“Sure, we can do that.”

“In six weeks?”

Mike did the mental calculations. “Yep, let me get another team member in here and we’ll run dual tracks today so we get everything we need to scope this.” The next eight hours flew by as our tiny team ran DeveloperTown through an expanded, accelerated onboarding.

I caught up with Mike on the way out. “Thank you. Based on what you’re seeing, can you give me a ballpark on cost?” Mike gave me the number. It was reasonable, given the ask.

Then, somewhere just south of the Wolters Chalmers exit on I-65, my brain caught up. You don’t have your biggest account anymore. You fired LinkedIn. You won’t have TalentConnect for business development. What you invested in v1.0 just hit a dead end. You’ve already written a check for the pre-2.0 work DeveloperTown has started. Jason, you have no money to replace v1.0 and no immediate way to get it.

My field of vision narrowed. I started seeing spots. Sweat broke out along my hairline, on my palms, under my arms. My breathing got shallow.

I needed to get off the road.

I pulled off at the exit and into the BP gas station at the base of the ramp, mumbling something to Lisa and Ben as I got out of the car. Did I stop the engine? Take the keys? Say anything coherent? I’ve no idea; that moment is lost to time. The next thing I knew, I was surrounded by tall, late summer corn, squatting with my head in my hands. I had no idea how much time had passed. I’d been crying.

I stood up, took a few deep breaths, and headed back to the car, where I explained everything to the team. Lisa insisted I call Mike right away with the bad news.

“Mike, it’s over before it starts. I’m doing the math, and… there’s no more cash. I’m open to ideas, I’m just… anyway, thanks.”

The next 3 hours were marked by silence, testy calls to our respective homes, and an inability to find music to fit the mood. I couldn’t imagine what was going through Lisa’s or Ben’s minds and didn’t want to know.

My own thoughts wandered back and forth between wishing for a miracle and wishing for a lightning bolt to take me out.

I was stuck—that damn press release! And worse, I’d convinced Lisa and Ben to join me on this journey! I felt sick.

As I got off 294 at 88 heading west, my phone registered a missed call. I played the message. It was Mike.

“Hi, Jason, I got your message, it sounds like you might have missed mine. Have a listen, and give me a call to see how you want to handle it.”

What?

Sure enough, I had another message. None of us bothered wondering why my phone hadn’t rung, we just played it:

“Hi, Jason, it’s Mike. Listen, I just spoke with my business partner. In addition to our development firm, we also do investments from time to time. We think you’ve got something special and we were really impressed by your team. Not sure what your cap table looks like, but when you get to the next round, if there’s space we’d be interested in coming in.”

I looked over at Lisa. I don’t think I’ve ever seen eyes open that wide.

I pulled off at 22nd and into the Oakbrook mall without saying a word. The car found a parking spot and, for second time in three hours, I cried.

I knew what that call meant—we all did. I called Mike to confirm that we were in business.

I bought a round of bubbles at Mon Ami Gabi. Not because we’d won, but because we’d won the day. In this new world of entrepreneurship, that alone seemed to be worth celebrating.

Less than two months later, Brand Amper was born on stage at HRTech in front of more than 9,000 people.

Looking out into the cavernous room, I could barely see anyone beyond the stage lights. None of them knew what it had taken for us to get here. None of them cared. But I did, and I couldn’t help smiling to myself.

We weren’t out of the woods, but I was out of the corn, so to speak. The lightning bolt had hit and I’d captured it in a bottle, for now.

I caught a familiar face toward the front, a woman who we were pitching.

She looked… bored.

The switch in my head flipped, and my smile froze. What the hell did I have to be so confident about?

I wasn’t out of the cornfield at all.

with truth+empathy,
Jason