Prepping for a new baby as a solo founder

We welcomed our fourth child into the world in June!

It feels like a big accomplishment to me, both just because wow, 4 kids(!) seems like a lot now, and also it's my first kid since being self-employed.

I think it makes the self-employment thing feel really real to me. Health insurance on our own, have to keep the business running, no one really to lean on business-wise.

For our first baby, I had one week leave. I think I spent it all in the hospital.

For our second baby, I had two weeks. We were also selling a house at that time, and I spent a lot of that time going back to the old house prepping it for sale.

For our third baby, I had three months leave (thank you Gatsby!!). It was incredible. Spent it building memories with the family at the pool, at the beach, and it was awesome.

This time around though, I don’t have a team. And I don’t have the budget to hire a team. And I can’t really put things on pause. I don’t work on the weekends normally, and my customers are generally fine with that I think. But I can’t go a week or more without doing support at the very least.

But I'm feeling really good about it so far. And I thought it might be interesting to share what I did to prepare, and how I'm thinking about the transition right now.

The Plan

Obviously we've known about the baby coming for a while, but I didn't do a ton to prepare business wise until 4-6 weeks out. Then I came up with a plan.

I knew that I wanted to have the product pretty stable. I also wanted to make sure it was easy for me to pop in and do support for 30 minutes a day or so. And also wanted people to be able to self serve as much as possible. And I wanted to make sure some marketing initiatives were in play while I was working less to keep that growth...growing.

Four to Six weeks out

About four to six weeks out, I went hard on product improvements. I had some good feature requests that came in, some new APIs that came available that unlocked some things for me, and I also discovered Taskmaster which helped me ship a lot of things in a very short amount of time.

In a little less than 2 weeks, I shipped a bunch of things:

• one time credit purchases (unlocks expansion for the business when people hit credit limits, and a potentially new segment for people that are opposed to subscriptions)
• magic coloring - automagically color in your coloring page. A little odd to me, but often requested for coloring book covers or getting ideas
• bulk photo to coloring page conversion - allows users to upload photos in bulk to convert to coloring pages
• fast photo conversion - added an option for cheaper and faster photo to coloring page conversion
• prompt based editing - a feature to make it easier to edit coloring pages. Just describe your changes in plain text!

Honestly, it's the most I've ever shipped in a two week period. It felt great, and I felt like it was enough to keep all my users / customers busy for a while.

Support

From a support perspective, I wanted to make it as easy as possible for me to keep up with support. I wanted to be able to pop in for a bit, get some done, and get on with the day.

Improved Tooling

I decided to invest some time in my support tooling / workflows. I use Fernand for support (highly recommend!), and they have a feature that lets you customize the sidebar panel, bringing in customer data and the ability to trigger actions.

There are a few things I need to do on a daily basis for users in support, so I decided to add those directly to my support inbox to save me a bunch of clicks. Now I can:

• see how many credits a user has
• see how many credits they have used
• send a password reset email
• delete their account
• add credits to their account

All without ever leaving the support dashboard. With the Fernand PWA, it let me do this all easily from my phone. This made handling support on the go really easy. Most days I didn't need to get my computer out at all, which was great.

Adding a support agent

The other thing in support is that Fernand released an AI agent right before I took my leave. I turned it on and monitored for a few days and while it wasn't perfect, it was good enough for me to leave on. It's trained on my help docs, so it answers those questions easily and immediately. I have had to do some training on it, correcting answers it gives, but overall I think it is a better user experience for people to get an answer right away from the agent and then I can hop in and update it later when I am online.

Marketing

On the marketing front, I wanted to make sure somethings were in play to keep moving while I was offline. I've been revitalizing and upping my email game for a couple of months, and I wanted to keep the momentum going.

Email broadcasts

I queued up a few broadcasts to my list to keep engagement up.

The first campaign was an example of using the photo to coloring page generator to convert art into coloring pages. I wrote up this blog post to go along with it Turn Famous Art into Coloring Pages with AI (and Try It on Your Own Photos Too).

Next up was a product updates email with everything I listed above - those are the easiest ones for me to send.

After that, I queued up an offer to non-customers only on the new credit packs - just letting them know that they could use ColorBliss without a subscription.

These three emails got me through a few weeks of not being hands on with marketing, and helped me establish a pattern I want to keep going. I'm going to try to keep up 1 broadcast a week, rotating between product updates, some kind of "try this with ColorBliss" (I have a few more fun ideas here), and then a more direct offer.

Email sequences

In the background, I also set up a lot more automations and sequences to make sure I'm sending consistently. This was a key mis-step for me in the past, leaving my list cold in between broadcasts and led to a huge tank in deliverability. I'm planning to write a post on how I recovered from that at some point.

Example flows I now have:

• customers get emails when their plan renews or they hit an anniversary
• all signups get emails at 30 days
• all signups get a 90 day sunsetting flow

These things keep my list warm and also prune off people who aren't interested. It seems to be working as far as I can tell so far, and it's helping my email costs stay in check.

Back at it

Baby is six weeks old now and I'm getting back to work. My time tracker shows that I logged about 30 hours of work in July, so I averaged around an hour of work per day. That includes some freelance work, so work on ColorBliss was around 30 minutes per day. I feel like I was able to keep the lights on, it continued to make good money with less time investment by me, my business is a little more efficient than it was before, and I'm excited to get back in and grow the rest of the year!