Behind the scenes - a yearly look inside my solopreneur journey

My 2023 year in review: highlights, lowlights, and what's coming in 2024.

I quit my head of growth job in June of 2021 to focus on my solopreneur business, Delivering Value.

• 2021 was about building - going 0-1 to get the business off the ground.

• 2022 was about experimentation - trying tons of stuff to figure out what worked.

• 2023 was about scaling - building momentum while juggling all the moving parts.

Here’s a look back at 2023. Things that went well, things that didn’t go well, and my focus for next year.

I’ve never been great at separating my personal life from my professional life (that’s even harder as a solopreneur). So it’s only fitting this review covers both.

It’s a pretty honest and vulnerable look behind the curtain.

I did this last year and got great feedback from everyone. I figured I’d run it back.

I hope you enjoy it.

Here’s what went well:

We started our next chapter as a family

2023 was a huge year for our family. We’re growing, thriving, and moving to the suburbs.

Here are some highlights:

We’re expecting our 2nd child. We’re super excited that our family is growing! We have a baby girl joining the Capland crew in June. We’re extremely excited and grateful to have another child joining our family.

Cameron just turned three. Our little dude is healthy and thriving. He’s into playing soccer, he loves hot wheel cars, and he rips around the neighborhood on his scooter.

Being a toddler Dad has tested and challenged me in ways I didn’t anticipate. Every level of parenting gets a little harder. But watching him begin to grow into a little boy is really fun.

We’re moving to the ‘burbs! We’ve lived just outside of Boston (in Medford Mass) since 2016. We love it here, but we need more space. We’re bursting at the seams in our current home.

We’ve always joked that we’d buy my Dad & Stepmom’s home if the timing worked out. A few months ago, the stars aligned and we decided to formally buy their house! It’s an opportunity we can’t pass up.

We’re moving to Acton on January 5th.

I made new entrepreneur friends (and learned tons)

Last year, I learned how important connecting with other advisors, coaches, solopreneurs, and content creators was.

Working in-house, it’s taboo to talk about salary and income. That makes it hard to self-assess sometimes. But as an entrepreneur, you’re comfortable sharing everything and comparing notes.

You learn a ton about what’s working (or not working) chatting with others running similar businesses - shortcutting the learning process.

This year, I doubled-down on those conversations and I connected with other solopreneurs serving the tech community.

People like, Daphne Tideman, Margaret Kelsey, Sam Leal, Anna Furmanov, Mike Rome, Devin Bramhall, and Leah Tharin. And I started meeting more regularly with some of my existing solopreneur friends, like John Bonini and Ramli John.

It can get hard/lonely building on your own. So in addition to helping the business, it’s also nice to build an emotional support system.

Those people have become a huge part of mine.

I became a creator

I’ve always considered myself a growth nerd who coaches and mentors other members of the growth community.

But the reality is, content fuels the growth of my business.

I did a bunch of little things to improve my creator game, like:

• Joining The Lab - a community run by Jay Clouse for creators to surround myself with other like-minded folks.

• Experimenting with Sparkloop to grow my email list faster.

• Migrating my email newsletter tool from HubSpot → Substack (more on why here).

Those helped a little bit.

The biggest impact came from two larger investments 👇

Launched the Delivering Value podcast

I’ve always wanted to start a podcast. So this year, I did!

I love chatting with growth folks and hearing their stories. I wanted to spend more time doing that. Plus, it would give me a reason to connect with people outside my network that I admired, but hadn’t met.

I figured I could monetize the show with sponsors and brand deals. And the podcast would give me tons of new content that would compliment my existing growth engine.

I locked in two amazing sponsors that were aligned with my mission (and audience): Navattic and MadKudu, and later partnered with Appcues - who I’ve collaborated with in the past on a user onboarding course.

Twice a month, I speak with growth leaders about the hardest moments in their careers - and explore what they’d do differently if they could go back in time.

I’ve published 20 episodes (as of Dec 2023) and average 200 streams each. I’m not sure if that’s good or not. But it feels like a decent starting point.

Most importantly, I started creating something that I was proud of.

Open-sourced my coaching curriculum

Like many of you, I listen to Lenny’s podcast. As a coach, I loved his episode with Matt Mochary. Matt shared his coaching curriculum - the Mochary Method. It’s an incredible resource full of actionable tips to help CEOs level-up.

I realized that I had a similar coaching curriculum for Growth Leaders. It lived in my head, and in bits and pieces I’d published on Linkedin, and across the internet.

I spent some time consolidating everything into one resource - a 45 page guide that includes (almost) everything you need to know about leading cross-functional growth teams.

Assembled a team to support my business

I identify as a solopreneur, because I don’t want to build a big business with full-time staff. I’m having fun keeping things lean and seeing how far I can go. But I can’t do it alone. Here’s who supported my business growth this year:

Accountant/ Payroll: At the end of last year, I spoke with my accountant (who’s also my Dad) who told me I paid too much in taxes last year. He recommended I switch from operating as a sole proprietor to an S-Corp.

On Jan 1, 2023 I officially switched from Andrew Capland doing business as Delivering Value to Delivering Value Inc. Now I’m the owner of the business - and a W2 employee. I have a payroll company to help with logistics and taxes.

Podcast editing/production agency: Through the recommendation of Margaret Kelsey, I also hired my podcast agency - Share Your Genius to help with all my post production work. They took care of all the logistics so I could focus on hosting the show. It was a great investment.

Executive assistant: I hired a new executive assistant in June - Crystal. She owns most of the operational stuff with the business (managing the client roster, contracts, scheduling, call-prep, podcast guest logistics, special projects, et).

That allows me to focus more of my time growing the business and working with clients. She handles the rest! 

Having an exec assistant makes a huge difference. Last year, I felt like a freelancer doing some coaching. This year, I feel like a business owner of a coaching business.

It’s a small difference in words. A huge difference in operations.

The business made 38% more revenue than last year

Everything above allowed Delivering Value to have a great year! The expenses did increase slightly with the additional resources (above). But they also enabled me to make more!

The business made 38% more revenue than 2022, and 30% more profit. My revenue breakdown looked like this:

1:1 Coaching: 36%
PLG Advising: 46%
Creator Sponsorships & Courses: 18%

Here’s what didn’t go as well:

In my daily/weekly operating system, I focus on things that have gone well vs getting stuck on what’s not working. But I cannot share the wins without acknowledging some of the speed bumps and self-doubt along the way.

Here are a few of those.

Business slumped over the summer

I had a great year in terms of revenue and profit. But I made most of the money in Q1 and Q4. Things looked pretty bad over the summer.

There were a lot of layoffs and budget cuts in the tech world. My business was directly impacted by those too. I was stressed.

I had a few weeks when I thought this solopreneur journey might be over. I considered getting a full-time startup job.

Eventually things picked up again. But it was a good learning experience.

I realized my revenue was too reliant on client work. Support services (like advising and coaching) are the first things to get cut when budgets get tight.

I needed to explore ways to diversify and de-risk.

That’s part of my plan for 2024 (more below).

I closed my group coaching program

I thought group coaching would be a big part of my business in 2023 (and beyond).

In January, I launched a 6-month group program for heads of growth called “Increase your Influence.”

Four amazing folks signed up for the pilot. I was pumped!

The first few calls were really high energy too. I pulled in great folks for the AMA’s (Sam Richard, Ben Williams, and Benyamin Elias were the first 3 guests).

But I quickly realized the main challenge for this type of group experience was how different their individual goals/challenges were.

On paper, everyone had similar titles, roles, and company types. But in practice, they were focused on completely different things at any given moment. 

That made it tough for them to collaborate and relate to each others challenges. I found myself reframing situations to be helpful and relevant to the rest of the group.

Most coaching blogs recommend group programs to scale revenue when your roster is full. That’s probably true. But sometimes you need to follow your energy and intuition. Mine was telling me that I didn’t love running the group. It drained my energy.

After 6 months, the program ended. I decided not to continue it.

I struggled to define what was “enough”

Even with the sketchy summer months, this year went objectively really well. But instead of being satisfied, I couldn’t stop thinking about missed opportunities.

• Am I doing enough?

• Should I be doing more?

• Will I regret not working harder?

• Could I be making double if I grinded?

I still don’t know the answers to those. They buzzed around my head all year.

Throughout this process, I’ve realized that my biggest fear is wasting this opportunity.

That motivates me to work hard each month. But it also prevents me from being satisfied with everything I’ve accomplished. A constant work in progress.

Here’s what I’m focused on for 2024:

Resetting our family life

With all the change happening in our family - I feel stressed and unsettled. I’m looking forward to settling into a new routine.

We’re moving on January 5th, so right now our home is an absolute mess. Our stuff is half packed. We have boxes everywhere.

We’re also prepping for life with 2 kiddos.

I remember what it's like having an infant. It's intense! Especially that first year. When you're not sleeping much and they get sick every 2-3 weeks.

I’ll need to adjust my life, and my work schedule, to leave more slack in the line to be successful in 2024.

Scaling (and monetizing) as a creator

Starting in 2024, I’d like to increase revenue from the creator side of my business with the goal of it (eventually) contributing 60% of my revenue in 2025.

That doesn’t mean my coaching or advising practice is going away. I love that work (and I currently have 2 open roster spots in Jan if you’re looking for some help).

I’m just diversifying after what happened this past summer.

In practice, this looks like creating more high-quality content across my owned channels.

Here’s my 2 priorities to turn this idea into a reality 👇

Priority 1: Publish more longer-form content (here on Substack)

I’m making an investment into publishing more longer form content (like this article) so I can control who sees it - not the algorithms.

In November, I moved my email platform from HubSpot to SubStack (to unlock it’s distribution powers) and will start publishing content more more regularly.

My short term goal is to create valuable content and increase my audience size. My longer term goal is to find some newsletter sponsors aligned with my mission.

Priority 2: Create a video first podcast

Right now, I have a audio podcast that I publish along with a video recording of the conversion. The content is good, but the video is boring.

I plan to transition towards a video first show in 2024. Something more engaging and entertaining. With higher quality editing and production.

I’d also like to experiment with (at least one) mini-series under the Delivering Value podcast umbrella. Specifically, I want to partner with existing growth teams to share behind the scenes content evangelizing what they’re doing - and why.

To bring those ideas to life, I’m increasing my partnership with Share Your Genius.

They’ll help me create a video first show - and improve the distribution.

That will make the show more fun to create. More interesting to my audience. And more valuable to my sponsors.

I also see tons of potential to scale my podcast into a huge part of the future of my business. I can’t wait!

2023 was all about scaling. Next year is going to be about innovating and finding new balance.