Ahh, another year as a business owner.

Cash coming in while you sit on a beach, sipping mojitos.

No challenging conversations to have.

Your marketing that used to work, still working.

Jk lol.

Entrepreneurship is sort of like standing in an ice cold pond. Above the water, everything looks great. Underneath, I’m freezing my balls off and just want to go home.

Welcome to my 2023 Annual Review.

This will mark my 10th year of business and my 10th Annual Review. It’s a fun process that I always end up spending too much time doing. Feel free to steal these questions and try it for yourself:

TABLE OF CONTENTS:

Okay, let’s start with the good stuff.

What Went Well Last Year?

Taco Tuesday + Time With Friends

A bunch of local friends got together for Taco Tuesday every week of 2023. I loved having this reccuring time on the calendar. It allowed me to disconnect from work and just be silly. Plus, one less meal to cook each week.

It’s true what they say: happiness is all about your close personal relationships. I used to think I had to win approval through hard work and achievements. Ironically, this mindset ended up isolating me from other people. Over the last few years, prioritizing my friendships has given me a much deeper sense of peace and acceptance.

The most satisfying parts of my year happened when I was doing physical challenges with people I love. Like meeting up with some friends in Joshua Tree to go bouldering:

Or backcountry snowboarding with my buddies:

All in all, this year was a great reminder that life isn’t all about work. It’s not even about doing stuff with people you love. It’s specifically about tacos, rock climbing, and snowboarding. Never forget that.

Launched “Weeks That Work”

A lot of entrepreneurs start their businesses in order to have more freedom, then find themselves overwhelmed and overworked due to a lack of structure. So I partnered with my former client (and overall badass) Gemma Gilbert to create and promote a new online course called Weeks That Work. The goal of the course is to help people build a repeatable weekly structure that supports their business while leaving plenty of time for recovery. We enrolled 87 people in the first cohort of the program, exceeding our goal.

It’s been a blast collaborating with Gemma on this. We decided to keep things simple by splitting the workload and the profit 50/50. This has created a really great partnership where we can each use our talents without having to manage the other person, and without feeling competitive. I’m excited to see the results people get from the program and continue to improve on it for the future. Hopefully this will become a program that we can run together regularly.

Experimented With YouTube

I started to burn out on blogging in 2022. In 2023, I got a good camera and lighting setup together and focused on YouTube for my content creation. I ended up putting out 17 total videos. I also made sure to update my my existing SEO blog posts so that I could keep growing my audience while I learned a new platform.

It took a while to get in the groove of Youtube, and I experimented with different formats. I learned that I’m better at doing short, teaching-style videos than I am at conducting longer interviews. Here’s a video that ended up getting some traction:

I’d like to shoot for weekly videos next year now that I have a system. If you know a good video editor, send them my way. I’d also like to get better at repurposing the same idea in multiple formats: written, video, and audio.

Went To A Retreat In Austin

One of my goals for 2023 was to attend more live events and retreats. I went to a retreat in Austin called “Buddhism + The Enneagram” run by Susan Piver of The Open Heart Project. The retreat combined teachings on the Enneagram (a personality framework) with meditation, journaling, and group discussion. I met a bunch of cool people, including one who I interviewed and another one who became a client. I also got to join Susan, the facilitator, for her early morning swims at Barton Springs. And we popped outside to see the solar eclipse:

While I was in Austin, I stopped at the legendary Franklin BBQ. Not wanting to wait in line, I ordered the 5 pound minimum online a couple days before. I met up with my team coach, Alison, to pick it up, business expensed it, and then ate the leftovers for the rest of the trip.

People wait for hours to eat at Franklin BBQ in Austin

My sister visited me in Austin before the retreat. We went mountain biking, ate at some great restaurants, and attended a honky tonk.

When I left for the retreat in Austin, cash flow was tight in my business. It felt uncomfortable to step away from work for 10 days. But the trip represented a turning point. Feeling refreshed, I had the best quarter of the year financially.

What Didn’t Go As Well Last Year?

Attempting to Scale

Going into January of 2023, I had 20 people signed up for a new program called Full Client Roster. The idea was to teach my most up to date marketing and sales system, but — instead of working with the clients myself — our team coach would work with them 1-1 to implement my system. This would allow us to offer support at a lower price, while theoretically being able to scale up to multiple coaches if the model was successful. This is an idea I’d played with for years and it was time to try it out.

Full Client Roster was a great idea on paper, but it was harder to pull off than I thought

The launch went well, in part because we offered a month-to-month commitment and a “get clients” money-back guarantee for the first month. This structure ended up being an uphill battle to deliver. Our team coach poured her heart into the program - she was doing two calls for each person per month, plus unlimited email support. And we did see some good results: one coach made an extra $5k in the first two weeks, another booked almost 40 consults, and another raised her rates and got her first $4,500 client.

Email from an early Full Client Roster participant

The problem was, one month is not a lot of time for the vast majority of people. Because we originally structured the program as monthly membership, instead of a 3 or 6 month program, many people stopped before they could build consistency and get results in their business. So even though we only processed a couple of refunds, we were still churning about half of the participants each month, meaning I had to replace those people just to get back to a baseline. And on top of that, I was splitting the relatively low ticket price for each person with my team coach. So I had all this time, effort, and stress going into something that wasn’t even bringing in much money for the business compared to just working with clients myself.

This was to be expected. Sometimes the thing that works at scale takes a lot of cash upfront. I still felt the model could work if I had multiple coaches and a large base of clients. So I met with my team and proposed some changes: we improved the program, raised the price, got rid of the guarantee, and required a three month minimum commitment.

Those changes ended up being better for the business and for our clients. We had someone enroll in April who ended up becoming an amazing case study, selling $38k in a single month. After 3 months in Full Client Roster, he then signed on to work with me directly and went on to close a $48k contract. Pretty cool!

Email from Jason, a Full Client Roster participant that’s continued working with me 1-1

But by the time we made those changes, things had already gotten pretty tight financially from the increased expenses. To be honest, I wasn’t feeling excited about the program anymore. And I hadn’t gained any freedom by taking myself out of the coaching side of things. I’d simply substituted something I enjoyed (coaching) for things I didn’t enjoy (admin, managing people, emails, stressing about cash flow). So I decided to take my attention off of Full Client Roster and focus back in on taking on 1-1 clients myself.

I think I needed to go through this process to realize that the dream of having a completely scaleable business was never actually mine - it’s something I felt I should do in order to be a good entrepreneur.

Financial Pressure

As part of my attempts to scale up, I had hired my first full-time employee and increased the hours of my team coach, adding to my monthly burn. So when things didn’t go as planned with Full Client Roster, it created some tight months for the business. With Emma going back to school in 2023, and us fostering a teenager, it was on me to provide. At the same time, a lot of the things that had worked to drive applications in the past started to become less effective.

I like to budget 60 days out for all business expenses, plus a profit and tax reserve. This year I was grateful for that buffer, because I definitely used it. I even had a few times where I needed to bring in money for business expenses due the same month. I still managed to keep our personal income steady, and I ended the year in a good place, but I didn’t like the feeling of having very little margin within the business. The ego boost I had originally gotten from hiring people had turned into extra stress.

At one point I had to text my friend Ben to come over and talk me off of the proverbial ledge. I told him, “I don't want to run this business anymore, bro. Maybe I should just look for jobs or go back to school or something.” Ben wisely told me not to make any big decisions while I was in a cash crunch. He said, “If you feel like you want to burn it all down, stop and just solve the problem in front of you first.” Yup. It’s amazing how those fantasies become less appealing when things start working again.

One of the upsides of feeling some financial pressure this year was that it forced me to innovate. I needed to come up with creative ideas, experiment, and step up my game. For example, I reached out to Gemma and offered to run a workshop for her audience, and that’s when we decided to partner together on Weeks That Work.

I also ended up created a limited time, Pay What You Want offer for some of my courses which ended up bringing in 170 new students (of course, some people paid as low as $1). Other things didn’t work as well, like a paid referral program I tested. But the financial pressure made me more willing to take action and try things that might not work. And I still ended up having my second highest year of revenue as a result.

I experimented with a “Pay What You Want” offer for my birthday

2023 reminded me that it’s okay to feel some stress and pressure as an entrepreneur. Yes, you should do what you can to make things more predictable and have reserves to fall back on in the lean months. But you can’t completely take the ups and downs out of business. And that’s okay. Pressure can create its own opportunities.

Another big learning was the value of repeat clients. Out of the 20 clients I worked with 1:1 this past year (not including Full Client Roster or other courses), 11 of them were returning clients. Some of them did their initial 6 month engagement years ago and returned in 2023 to continue coaching.

If it weren’t for those returning clients, things would have been a lot rougher. When my lead flow slowed down, I was able to reach out to past clients and retain my existing ones. The takeaway? Getting new clients is overrated.

Challenging Conversations

Because of the financial pressure, and winding down Full Client Roster, I decided to bring my full-time employee back down to part-time, and reduce the hours of our team coach. Those were not fun conversations to have. But I had to have them.

2023 included some challenging conversations with Emma and my family as well. I still have work to do when it comes to sticking to my boundaries while at the same time not being a selfish bastard. But progress has been made!

What Am I Focused On This Year?

2023 was a challenging year. One of the things that got me through was the power of partnerships: with my wife, friends, colleagues, and clients. So much more is possible when two people are aligned in their values and goals.

So while I have a bunch of specific goals for the first quarter of 2024, I’ve found that the best thing to do when entering a new year is just to choose one word. One theme that I can use to guide my decisions throughout the year. And that word, for me, is Partnership.

Emma and I fostered a teen this year (heart for confidentiality)

For so much of my life, I’ve been obsessed with self-help and personal development. Of course, there’s nothing wrong with improving yourself. And it’s true that we sometimes need to work on ourselves so we can be better for other people. But I’ve learned that there’s only so much growth that can happen in isolation. Humans evolved to help others, and by doing so, help themselves.

Some of my most fulfilling moments this year happened in partnership with other people: foster parenting with Emma, snowboarding with friends, launching Weeks That Work with Gemma, and seeing clients succeed.

Here’s to more of that in 2024.

Past annual reviews:

Annual Review 2023: Taco Tuesday, Texas BBQ, and A Big Slice Of Humble Pie