If I do this right, the way I want to do it and believe that I can do it, this will be a big year for me. Maybe the biggest.

As I shared a couple of blog posts ago, I turned 41. Age is only a number, but it has become a symbol on a map. It's the sign post on the road, a ticking clock. Turning 41 in 2023 meant a lot to me. It meant roots, friendships, patterns, and routines. It meant kids that are getting older and more independent. It meant a marriage that lasted many times longer than the one between my mom and dad.

I wanted financial stability when my kids were young and we had a mortgage on our house and then a major remodel. Now it's different. I feel like I can dream big again. This past year set the stage. This next year is when I go for it.

Shovels to find product-market fit

For me, this is going to be the year of Shovels. I've already gone all-in on this idea. I've raised $1.3M to date, and likely will raise another $200K more before hitting the upper limit on how much dilution we can take in this round.

While the fundraising is important because we need it, the goal is to build a big business. Big to me, right now, is $10M ARR (annual recurring revenue). That's the target, and I'm willing to fight tooth and nail to get there.

The path that we'll take is selling to the enterprise. We have to sell bigger deals to bigger companies. The ability for me to hire a sales team depends on it. We'll still take the smaller customers -- I want to support climate tech startups -- but we can't spend time handholding them through the process. The product itself will need to do 99% of it.

We have 10 small customers. Our MRR (monthly recurring revenue) is already higher than my last two bootstrapped companies. This business is inherently different.

The big deals are in my pipeline, and I'm attracting an elite team to help me find more. It's all very clear to me. It just makes sense. It's like I can see the future.

When I think about Shovels, I feel a combination of pride, excitement, and anticipation. It's a potent mixture. I think the last time I had it was in college. Everything worked out as planned (I went to grad school at Harvard) and I have many reasons to believe that my dreams for Shovels will come true too.

I'll know if it's working by the start of summer.

Teaching to be rewarding

When I'm not doing business, I'm teaching it.

This spring I'll teach a couple of supervision and management courses that I've never taught before. I'm looking forward to it. I did most of my course preparation last week in Hawaii. Poolside, palm trees swaying in the breeze, the Pacific Ocean in the distance. Kids playing in the pool. It could be worse.

I decided to introduce cases into my teaching. Every week, we'll discuss a case and I'll let the students work on their responses in class. The supervision and management cases are interesting. We'll discuss Uber and Netflix, how cultures form, and how important leadership is throughout the lifecycle of a business. As Shovels grows up, examples like these will take on new meaning. It's the perfect time for me to study management, supervision, and leadership.

I'm living these lessons as I teach them, and for me this has become something of a superpower. I really enjoy interacting with students in class. I like extemporaneous speech. I look forward to grading. Perhaps someday it will get tiring. Maybe I'll find that I can no longer be an entrepreneur while I teach entrepreneurship. I'm not so sure, though. For now, I'm finding that doing and teaching at the same time has a positive amplifying effect on both. If that ever changes, I'll deal with it then.

Friendships to matter

A couple of weeks before I turned 40, I took a group of guys up to Pinecrest. We hiked, we swam, we grilled, and we played Cards Against Humanity. It was awesome.

I remember vividly one moment at the end of the weekend. Only two guys remained, and since I was their ride home, they helped me put the cabin back together. We were sweeping the front deck when my career came up, and I lamented that I wasn't sure exactly what I was going to do next. I had some ideas but I was uncertain which one to pick. I told them I really wanted to be a climate tech CEO.

"That makes all the sense in the world," one of my friends said. The other agreed emphatically. On the drive home, I decided my building permit idea was the best one and hired a couple of programmers on Upwork to start scraping permits in Contra Costa County the following day. This was the start of the chain reaction that would become Shovels. It happened because of my friends.

I'm making more friends as a result of the work I'm doing on Shovels and at DVC. I'm also hearing from more old friends than any time in recent memory. I find it very rewarding, and it tells me that I'm doing something right. My network grows when I'm most productive.

Fitness to keep improving

I'm in the best shape of my life. It's true. I credit a combination of my daily core routine, training for some endurance races, and doing a triathlon which really was about forcing myself to swim laps. Now a typical workout week for me looks like this:

• 5 mornings of 10 minute core. Mondays I do a 5 minute straight arm blank. Tuesday through Friday I do 4 minutes on my elbows. The rest of the workout is various crunches, stretches, squats, and 40 pushups.
• A couple of 5.5 mile runs. Plus one 10+ mile run or a 35 mile bike ride.
• 1 mile swim at a pace of about 2 mins per 100 yards.
• 1 Peloton workout. My favorite is a 20 minute ride followed by a 20 minute full body strength

The morning core routine, which I've now been doing for more years than I can track, is table stakes. It's always there, so I don't think about it. This means I work out twice on most days. It feels normal. In fact, on days when I don't work out at all, I get restless. That's when I head out to the backyard cottage where we have our Peloton stuff and knock one out. I have to exercise every day or I don't feel right.

When I was younger, I remember thinking one sweaty exercise a week was all I needed. Maybe that was true at the time. A few years ago, I got into a rhythm of exercising every third day. One day on, two days off. It felt like work, but I stuck to it. I've been narrowing that gap in off days ever since, and it's now to the point where even on vacation I have to get my workouts in. The only days I didn't exercise in Hawaii were the days spent packing and flying.

I'm proud of my Strava profile. I want to keep it going.

To take chess more seriously

Chess is a different kind of release. It's what I do to ramp into work mode. It's also what I do to reward myself for getting work done.

I happen to be on a really good clip right now. My chess is strong, but I've been playing long enough to know that it's cyclical. This could last another two weeks or maybe another two months. Then I'll hit a losing streak and drop about 200 points. Right now, though, I see the board and accurately anticipate my opponents' moves. I know this because they slow down in response. It's thrilling.

I play 5-0 and 3-0 games. That means five minutes, no increment, or three minutes, no increment. These are fast games. I like using the clock as a weapon. No incremental time after each move (alternatively, you can get 2 or 3 seconds back after each move).

A different personality comes out when I play chess. I talk shit (chat it, actually). I'm hyper-competitive. I allow myself to dislike my opponent. I'm mean!

If I had to critique my entrepreneurship, it's that I tend to be too nice. It's great for building a network, but it's probably bad for sales and negotiation. I want to pull parts of my chess personality into my entrepreneur personality. That's one goal for this year, especially as each new Shovels enterprise deal becomes a negotiation.

That's five good goals for me to keep in mind going into this year.

I'm ready 😁