I applied to be a professor at Diablo Valley College around the same time I started building Shovels. Part of what attracted me to teaching was the responsibility of being at the front of the room. There's a performance to it. The students are depending on what I bring that day, how well prepared I am, and how confident I am on my feet.

It feels like running a business in some ways, except there's no team. It's just me.

I started teaching because I wanted practice speaking in public and explaining complex concepts to a wide range of people. I also wanted to contribute to a broader community and get to know it. Teaching offered all of this.

In the early days, when I didn't know what would become of Shovels, teaching was my insurance plan. Now, it's more of a sanity check. It serves as a reminder of what entrepreneurship is and what it means to people just outside of my tech AI bubble. For my students, I hope my presence in the classroom is equally revealing: a glimpse of the other side, a VC-backed tech founder teaching entrepreneurship to students who aspire to open nail salons and cannabis farms.

Importantly, teaching has offered me a glimpse into myself. I need to communicate better, be more real, use a wider palette of emotion when I speak. I need to strive for honesty and transparency and try to turn that openness into insights.

My teaching commitment plateaued, but Shovels kept growing. As Shovels grew, the challenges became people problems as well as technical problems. I discovered that my own performance and the team's performance are connected. If I want the team to get better, I need to get better too.

But how?

About a year ago, I was pretty anti-coaching. Investors introduced me to coaches, and I interviewed some. I thought they were too expensive and I didn't think they would help. Maybe I was right at the time.

But as the complexity of our problems grew, my thinking changed. I no longer had the answers all the time. I needed to build a culture that was determined to make good decisions. I needed to be the best leader I could be for this company. An entrepreneur I admire referred me to Leaders in Tech, or LIT. I applied, interviewed, and was accepted.

I remember being skeptical when I first read about this program. It wasn't cheap (about $20,000), but it was cheaper than one-on-one coaching. Its name was hokey, but the roster of tech leaders that went through it was wildly impressive. It also helped that the program traced its origins to a popular course at the Stanford Graduate School of Business called Interpersonal Dynamics, or "Touchy Feely" as it was known to students.

The thing that convinced me I would love this was T-groups.

I'm old enough to know how I like to learn. With guitar, I learn best by jamming with different musicians. I've taken lessons, bought lesson books, and watched hours of guitar videos on YouTube. Nothing compares to playing in a band. A band is like a project. Let's learn the songs, memorize whether the verse or the bridge comes after the second chorus, hit those breaks on the intro vamp. There's no better way for me to learn.

Programming was the same for me. Books didn't get me very far with Ruby on Rails. Having a project I was desperate to build did. That's the story of Toofr: I desperately wanted to learn to program, but it didn't make sense until I had to build a website that guessed business email addresses. The project helped me push through the learning curve. The project made it all click!

T-groups are project-based learning for leadership. Learning by doing, with other people. That was much more appealing to me than spending an hour with a coach and filling out personality surveys. I'd learn by watching other leaders, studying their flaws and their feats.

This was all just an assumption. I'd need to attend the opening retreat to see if my assumption was correct.

I arrived on a crisp Friday morning. The drive from Walnut Creek to Santa Cruz was easy. Podcasts and a brainstorming call with my cofounder made the hours fall away. I was quite early, so I sat in the car and finished my conversation. There was a lot to discuss. Our decisions are only getting more complex, the stakes only getting higher. He wished me well, and I thanked him for being supportive of this program. I texted my wife and told her I had arrived safely and would let her know how it was going.

And that was it. My professional and personal obligations were met. Work and home would be fine without me for a few days. I was still early, so I took a seat in the lobby and read the newspaper. When people filed in with name badges, I figured it was time to find the meeting room. I planned to be early, obviously, but I didn't want to be the first one there.

I want things to start on time. It's not just respect; it's a signal that demonstrates preparation and confidence. The LIT kickoff meeting, as I recall, started right on time, and I remember looking around the room and noting that everyone was there. It looked like all of my fellow founders had shown up on time! That was the first little tingle that I'd found "my people."

I had already met a few of them. They came from all over the country, across many tech industries: finance, biotech, semiconductors, marketplaces. They had raised a lot of money. Some had recently exited or were about to exit, and some had cofounder or investor conflicts. Each came with their own reason for needing some sort of help.

Why else do you spend this money and give up a four-day weekend, 9 a.m. to 10 p.m. every day, to meet a bunch of strangers? You do it because you need it. I didn't know all of this upfront, of course, but even those early conversations dropped clues.

The days were structured like this:

I suppose at this point I should describe what the T-group is like. The kickoff session defined it as a lab for experimentation. There's "no leader, task, structure, plan, or predetermined agenda." My group was a dozen founders and two facilitators. There was one other T-group at the retreat. I think they had 13 founders. Our T-groups were completely separate; only the framework sessions and meals were shared.

I'd never heard of anything like this, and I was fascinated by it. I eagerly found my room, sat, and looked around.

After a few moments, the first person spoke. We discussed norms, whether we'd be allowed to take notes, and how to handle late arrivals after breaks. I didn't know it, but the T-group was launched. All the stuff we'd been told to consider, like how to share and disclose information about ourselves to become "known," was happening in real time.

I was fascinated. I was hooked. The time flew. We had more framework sessions, but I just wanted to get back into T-group so I could learn and watch and participate. Knowing that my tendency is to sit back and let conversations unfold before I speak, I tried being more assertive.

Knowing that I really don't like giving negative feedback (LIT calls it "developmental"), I seized an opportunity to tell the group how I felt about them being late after a break. Was I actually miffed? No, not really. We were becoming more casual, and that was probably okay, but I needed the practice, so I did it. I admonished them. I told them why it mattered to me and how it made me feel.

And then the spotlight shifted to me. It was rough. I shared my discomfort with giving feedback, and one of the facilitators suggested I give developmental feedback to everyone in the room, 11 of my peers and both facilitators. Right then, right there. He presented it as a challenge. I had to accept it. I tried not to hesitate. I just went for it, and when I was done, I let the feelings wash over me. I felt hurt, embarrassed, confused, angry. All the things! Most of all, I felt overwhelmed. Tears welled in my eyes, and I didn't know what to do about it. They fell, and I felt the arm of the facilitator around my shoulder. I appreciated the comfort but it only exacerbated my surprise: who am I, again? A 44-year-old CEO, crying in some group therapy session in Santa Cruz?

I couldn't believe it. But that's the point. And the other point is my T-group was fired up by my performance. They loved it. To be clearer, they loved the emotion. They loved that I showed how I was feeling, rather than just telling them. I learned that I tend to operate on a narrow band of visible emotion. I feel things, but I soften those feelings when I share them. I'm very transparent about facts, but not about feelings. Going forward, I need to do both.

This learning happened halfway through the retreat; it was referenced a few times in our closing remarks a couple of days later. I still think about it a lot.

This was my own experience, the only experience I can share. The others in my group had their own journeys with it. Not everybody cried, but I think most of us did. I wasn't counting. Disclosure is hard for everyone.

The common theme was this: "If I open up, you'll find more reasons to dislike me." And the common experience was the opposite. The more my T-group opened up, the more connected I felt. It's so apparent when someone is speaking their truth, and the feelings of admiration and camaraderie follow naturally.

We never dissected the word "like." It came up a lot. We all used the word, but I still don't know what it means. The LIT-approved word is probably "known" or "connected" because those seem to lead to what we refer to as "like." I don't know. I'm still learning this.

I have another eight months in the LIT program. The time won't be as condensed as it was in Santa Cruz, so I don't know if I'll learn the same way, but I'm excited to get back in T-group and refine my approach to emotional disclosure.

Just writing this, I think, makes me a better leader.