My Personal Scatter Plot

J Paul Hendricks at Yellowstone fade

I’m a finance tech industry operations and growth veteran that has always had one foot in online business/publishing and saas. This interest in a broad spectrum of industry verticals, revenue models and product/service offerings is an extension of a deeper passion: my belief that we’re in a golden age of bootstrapped business creation.

It has not always been this way. And each of us will face different challenges in pursuit of such business goals. But it has never been easier to build and launch businesses that can generate significant financial rewards and create independence, for owners and their teams.

I want to help others do both, as I continue doing the same myself.

Motivators & Data Points

At a glance, my life is a seemingly random assortment of events, encounters and wholly unlikely endpoints. But there are some ideas that underpin much of what I do and how I do it.

One is that I am especially interested in the bootstrapped approach. In some industry verticals it is, of course, essential to take investor money. But the downsides of outside funding are many. Taking investment too fast (or at all) has led many promising startups astray. When funding is taken, it is best done from strategic investors (that have more to offer than just dollars).

On the other hand, retaining full control means founders can steer their business exactly where their vision leads them. And they can do so without delay or distraction. Hunger makes for leaner, meaner companies. Bootstrapped founders tend to do more with less, and are stronger for it in the end. I know that I am.

Now, I’m now applying my fintech product and business development experience to building and investing in saas and online businesses.

This is how I prefer building businesses myself, and it informs my own investment decisions as well. My endeavors on the startup and online/digital business front are not new. But the last few years have been an amazing time to be building in the SaaS, marketing and media space.

The digital publishing, web 3 and AI revolution are all especially exciting and still accelerating. And I was building when it was still a digital frontier, as the ‘web guy’ at a NYC design studio in the 90s. My business growth and marketing experiments predated even that.

Personal Scatter Plot

But a trading technology shop lured me away and a long, circuitous finance career ensued. I worked in various roles, from tech vendors to a top investment bank and back again. Now, I’m now applying my fintech product and business development experience to building and investing in saas and online businesses.

And I can’t help but view the tectonic shifts in the digital landscape through the lens of my finance industry experience. It’s often exciting, and frequently inane…but it’s always interesting.

Best-Fit Life Line

My life (and business activities) are a kind of personal scatter plot of events and ideas. I’m not sure where, in the end, the best-fit line will point. But my experiences, wins and losses, and the many brilliant people I have learned from all contribute to how I continue to build and grow into the future. These also inform my advisory and consulting services.

One contextual point I’ll note here is my in-progress, mid-life migration out of the finance industry mainstream, and into new business endeavors. For a long time I resisted quitting the cushy paycheck of my capital markets career. But in the last few years I decided to apply my bootstrap beliefs to my life overall (and not just business). Solo and strong!

In my investments, my business and my life, the goal is financial and operational resilience.

My current initiatives include a marketing tech saas product (and another in the pipeline) as well as other online business projects across multiple niche verticals. Part of the reason for the multiple ‘small bets’ approach is about maximizing financial security through multiple revenue streams.

I’ve always put a premium on diversification of income and monetization methods. It’s a natural part of risk management. This is also reflected in my portfolio strategy, investing in other startups and alternative assets alongside my traditional holdings. In my investments, my business and my life, the goal is financial and operational resilience.

Jason Paul Hendricks at Gallatin Range
At the Gallatin Range

These principles are also embedded in how I’ve managed businesses for others, and the guidance I give to my consulting clients. It’s not always what we want to hear but managing risk is part of maximizing returns.

Self-Learning & Relearning

Another idea that has been a foundational part of who I am is about education. Specifically, about continuous self-learning and upskilling.

Learning and upskilling (or reskilling) is something that people deep into a career or midlife often start thinking about. And it’s become a broader focus in recent years with all the economic turmoil. The industrial upheaval that AI presents will now hyper charge these discussions. I have, for a long time, thought about the challenges faced by those educated in the old paradigm but facing the realities of the new global (and digital) economy.

This may also seem odd when you consider that, when I was supposed to “finish school”, I dropped out and moved to New York City to play music (I was always a humanities guy). Ironically, that decision directly connected to me working for over two decades in the finance industry, from startups to the Fortune 500. But it never would have happened without a voracious appetite to learn and grow.

This focus on observation, exploration and learning has served me in many areas of life, not least of which in business. Conceiving or identifying new ideas and opportunities is a fundamental part of entrepreneurship. But the ability to differentiate good ideas (or strategies, plans, etc) from the great ideas is usually not easy.

This hemispheric synchronization informs how I approach an advisorship or consulting engagements as well.

It requires both qualitative and quantitative skills. And the bootstrapped startup space magnifies the importance of both.

Fortunately, working in the trading and finance industry made me process-oriented and data-driven. But the humanities; media, writing and music are in my bones. Alas, the analyst and the artist can co-exist. The intersection of these two has also proved a powerful combination and served my businesses and clients well.

This hemispheric synchronization (to borrow a brain reference) informs how I approach an advisorship or consulting engagements as well. Most business challenges are complex and multi-faceted.

In addition to determination and persistence, finding the optimal solution requires attention to detail, an open mind and a willingness to hear (and execute on) hard truths. I don’t just bring these but also help clients access the same in themselves.

J Paul at Yellowstone Pano
Watching the world change in real time at Yellowstone National Park

Notwithstanding my ravenous consumption of information, some of the most important things I’ve learned came through direct experience. Of course, losses teach us more than wins. And if our most valuable lessons come from mistakes then I truly have a wealth of experience. Of course, I have also been fortunate to have many (much) smarter people in my life. Much of what makes us who we are comes though the examples and wisdom of others around us.

This gives a keyhole view of me. These things, plus some luck and lots of hard work, have all contributed to who I am. And I look forward to sharing more with you, if you are interested. Feel free to reach out and say hi!

— Jason