Build, Buy or Apply?

For the first time in my life, I’m struggling to decide what to focus on next for my career. I’m between gigs, which isn’t unfamiliar territory. Most of the time I end a gig because I’m burnt out, done what I wanted to accomplish and know that it’s just time to move on. I’ve only once left a job with another waiting.

In between jobs I’ve taken about five mini retirements like Tim Ferris talked about in The Four Hour Work Week. I’ve taken a few months off to play golf, another few months to learn to sail, seven months off to travel around Argentina and Colombia and a couple months for a cross-country road trip. And just two years ago I took four months off for the birth of our daughter.

Each time I knew I needed a break. I knew where and how I wanted to focus energy, and I set a clear timeline. This time is quite a bit different. Sure, having a family and the responsibility is a major difference but, more than that, I don’t want to take a break. We can afford a few months break, but I feel like that would be lost time.

I want to build and earn and make something. I just don’t know what, yet.


I’m going to explore three paths:

Build: start something from scratch. Go zero to one on something that’s going to generate income.

Buy: purchase something small with solid potential and focus on retooling and growing it to cashflow.

Apply: explore options for joining an existing company/team, but be VERY selective about the roles, people and expectations for my time.

Rather than picking one thing, or simply falling back on the familiar, I’m going to make a series of small bets on each path.


My goals are simple…

1. Stretch and Challenge Myself: I want to push myself to get hands on and develop some new skills. More writing and creative output. More reps at sales and business development. More technical experiments.

2. Diversify Income: I want to have at least three solid income sources validated and able to scale in the next six months.

3. More Product, Less Service: I’m going to build a couple “products” to decouple time from money. I’ve always been in the services business trading time for money, which leads to working on someone else’s schedule. I’d rather have more control over my schedule and the ability to flex around my family’s schedule where needed.

So, what’s first?

For the Build and Buy paths, I’ve been compiling a list of ideas for a while, so I’m doing some triage, research and validation to add structure and clear prioritization.

For the Apply path, I’m in early discussions with a couple firms, and I have a short list of other companies I’m reaching out to as well.

I’ll plan to share weekly updates over the coming months, sharing progress, wins, losses and learning along the way.

Ideas

I’ve kept a running list of ideas for a few years now, and it’s about 60 in total right now. Every time something comes up I add a quick note to the list with a short description and a link to what triggered the idea. Not everything is original, or even good, but it’s fund to read through and see what’s caught my attention over time.

As I’m trying to sort out what’s next, I’m going through the list looking for what’s interesting to me right now, and what could be a fun bet to make by either building and MVP or looking for an active business to buy or invest in.

Most of the ideas fall into these five buckets:

1. Content/Affiliate: the name says it all. There’s about a dozen of these ideas on the list for things like home theater, hangover cures, robo calls and more. I’ve always been intrigued by affiliate marketing, but I’ve never done it. I think it would be fun to experiment here, get hands-on and learn the basics. A simple content site would cost under $100 for the year, so the overhead and barriers to entry are super low.

2. eComm Shop: I need to get better a pure ecom, from front to back, so this is definitely one I’m going to trial. Starting with a dropshipping a is low risk and low cost model to validate a niche and product to focus on scaling. And starting with a focus on organic from the start will be a long-term differentiator against the mostly paid traffic focused crew in that space.

3. Digital Products: I like the idea of creating a digital product to sell. That could be a simple book, a guide or course of some kind. I’m not set on what the topic could be, but I’m thinking something around first time dads, cooking, running a services team/business or lifecycle and email marketing.

4. Services Business: I’m the most iffy on this group, but it’s also the most familiar and confident since I’ve run and grown services teams in agencies, consulting and SaaS platforms all of my career. I need to do the work to pick a lane and go for it I guess.

5. Micro-SaaS: This would be fun, but I have a very tight criteria set for this so I’m not overextended on the purchase and can ensure proper technical product support as a non-technical lead.