My Next Chapter

From Startup Founder to Sustainable Cashflows

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The last year has been hard.

A year of professional soul searching. 

At the end of 2023, I made the decision to move on from LOTI. The company I founded in the height of COVID with a mission to enable every professional to maximize their ROI of learning on the internet.

I faced the reality that it wasn’t going to become the successful business I worked hard for it to be.

I didn’t come to the decision lightly.

I threw everything at it before recognizing that it was no longer the highest leverage thing I could be doing. 

I contemplated what to do next. 

Start something. Again.

Go back into big tech. 

Join a startup. 

I did every assessment. Spoke to everyone I trusted. Consulted on other businesses, stopped and started different projects, and spent a lot of time self-reflecting. I discovered that what mattered most in this next chapter were team, agency, and ownership. 

A MAIN STREET FOUNDER MINDSET.

I have been drawn to entrepreneurship my whole life. It is what I know from my parents, from the city I grew up in, from the people I surround myself with. 

After being in Silicon Valley, part of big tech, and building startups for the better part of 15 years, I had become disillusioned with the business model of growth = success. Of outcomes being either a 0 or 100. With rarely anything in between. It wasn’t just me. I was seeing a shift happen for many tech entrepreneurs with the end of ZIRP.

I reached out to an old friend who had taken this leap. From the world of venture backed businesses to businesses on Main Street. I wanted to learn what he knew. I wanted to understand why he made his decision. 

We talked about the holding company he had started in 2019 — Enduring Ventures. The ups and downs of it all. The hard lessons he had learned and the successes he was seeing. The work he was doing, and the companies they were buying, reminded me of how I first thought of entrepreneurship. 

It wasn’t about VC dollars and growth at all cost.

It was about consistency, and cash flows. 

It appealed to me. This was the business building I had seen most of my life.

I decided then: I’m going to buy a business to own and operate. 

GOING ALL IN. AGAIN.

Why now? Because ownership creates optionality.

No job is easy. I always want to be doing something that gives me disproportionate upside. 

And well… the cold water doesn’t get warmer if you jump in later.

As I search for the right business, I wanted to be learning. To be operating. 

Everything is downstream of practice and time spent.

So I went back to that same friend and asked if there was an opportunity to join him. To support the work him and his partner were doing. Where I could be helpful. 

There was. 

The answer was their ISP portfolio company. Growth had stagnated and they needed someone to get into the muck on Sales and Marketing. I didn’t know a whole lot about ISPs but I had the confidence and curiosity to help them solve this problem. 

I spent the last few months growing the business, setting it up for greater financial health and success. More recently I’m excited to share that I’ve taken over day x day responsibilities as the interim COO, and joined Enduring Ventures as an Operating Partner. 

But while operating during the day, nights and weekends are reserved for Searching. 

It is still early days as I develop my buying thesis and narrow in on exactly what I’m looking for. But I couldn’t be more excited — much more to come in the future newsletters.

WAIT, BUY WHY.

I know I haven’t written here in a while. This post may feel out of the blue. 

So if you’ve made it this far, thank you. 

What I can promise is that the title of this newsletter — The Infinite Learner — is how I’ll approach this next chapter. Putting myself in uncomfortable situations in order to learn always, in all ways. 

And of course, share this journey and learnings with you. 

This update also serves as a flair that I am open to connecting on the topic of searching, buying, and operating businesses (just hit reply!). And because being an entrepreneur can be lonely — better to have a tribe then to go at it alone.

Over the coming weeks and months you can expect to hear from me more often. I miss writing regularly, and the serendipity that comes along with it.

This is the start of the next chapter. Thanks for coming along.

With gratitude,

David