Will Little Subscribe

I turned 40 this summer. I spent my 20s building businesses and my 30s investing in early stage founders. Here are a few things I’ve learned thus far.


FYI - I originally wrote this up as a post on Reddit here.

Greetings to anyone else out there in the Oregon Trail Generation that is crossing (or has recently crossed) the 40 mark. :) We’re old enough to remember an analog world, but young enough to have grown up with the early days of the Internet. It’s been quite a ride thus far.

As Anna Garvey wrote in this brilliant post about the uniqueness of our generation:

We used pay-phones; we showed up at each other’s houses without warning; we often spoke to our friends’ parents before we got to speak to them; and we had to wait at least an hour to see any photos we’d taken. But for the group of kids just a little younger than us, the whole world changed, and that’s not an exaggeration.  In fact, it’s possible that you had a completely different childhood experience than a sibling just 5 years your junior, which is pretty mind-blowing.

The whole article is well worth reading.

I am regularly thankful that I didn’t go through my teenage years with a smartphone and social media, but those came pretty quick in our 20s and we were the guinea pigs. They still mess with my head at 40, and my kids (9, 12, 14) are now part of a new group of young GenZ-ers choosing to limit their own screen time because they don’t like how it makes them feel (!). They’d prefer to read old-school/non-kindle books and play hours of Dungeons and Dragons, which is pretty sweet (and highly recommended).

Anyway, in my 20s I learned to code, built some online businesses, and got lucky that a couple of them were in the right place at the right time and got rolled up by bigger players. In my 30s I started investing in a bunch of founder teams across digital (B2B SaaS, marketplaces, consumer) and brick-and-mortar (education, food service, on-prem VR, etc…).

I’m in the process of writing multiple books on angles/approaches I see relatively open in entrepreneurship and health science space (I did my doctoral work in bioengineering) - and maybe I’ll finish some of them before I turn 50 - but I wanted to take a quick moment and share a few things in case anyone out there finds these useful and/or would like to chat about them:

Most businesses fail because of relational conflict that leads to operational inefficiency

No one really talks about this because it’s super, super awkward and embarrassing. If you Google “reasons why startups fail” you’ll see lists of things like not having market need/demand, running out of cash, getting crushed by competition, etc… but from my experience the root cause of closing doors is always because of founder/team/investor conflict, or simply a lack of healthy communication that leads to slow relational death, operational sluggishness, and/or an inability to pivot.

Therefore, as an entrepreneur one of the most important things you can do before you even think about business stuff is to pick a personal worldview that promotes empathy, generosity, and compassion. Be aware of your biases, personality, wiring, quirks, and dogma that you believe. Actively work on becoming more empathetic, generous, and compassionate (yes, these are worth repeating). Wake up every morning and meditate on these things, and work through conflict graciously...bringing in thoughtful 3rd parties to mediate as needed.  

If you don’t find yourself ever in conflict, you are either not aware of the communication break-downs that are happening around you, or you aren’t being ambitious enough. Likely both.

Build your own financial model from scratch

If you don’t know how to build, forecast, navigate, and maintain a basic income statement, balance sheet, and statement of cash flows, take a few hours to learn. A VC friend and I wrote up a series on startup financial modeling here if you are interested in getting started, otherwise ask your accountant (or friend in finance/business) to give you a primer.

Having your past performance and future projections in one collection of sheets, with all your assumptions and custom formulas baked in, is a pure gold mine. It will help you face the brutal facts of your business, allow you to smartly make capital and resource allocation decisions, and give you the power to run experiments with a simple model to see how tweaking this or that impacts your long-term cash flow.

If you raise money, being able to walk an investor cell-by-cell and sheet-by-sheet through your model is a fantastic way to win their heart (it’s certainly one of my love languages, and I know I’m not alone).

Understand how to create leverage and build assets

If you haven’t yet fully digested all of Naval’s succinct material on the topic of leverage, read the tweets/articles and listen to the full podcast. Long story short, old-school things like money, human resources, and books, and new-school things like blogs, email newsletters, videos/podcasts, and - perhaps most importantly - code .. are tools/things that can make you and your businesses money while you sleep. If you are a person of integrity and can focus on producing assets that create leverage, you will go far in life.

Get into flow often

That state of mind where you lose track of time because you are immersed in an activity, project, book, code, etc… you’ll want to optimize your life to do this as much as possible. Not only will this help you with the three pieces of advice I offered above, but it’s likely to make you a happier person.


I’ll stop there for now. I’d be happy to answer any questions and/or support others who can fill in more color on the above from their own experience. Feel free to chime in over on Reddit here, or shoot me an email at will@wclittle.com.