In the spirit of Seneca, a founding Stoic, I am looking to back founders who have thoughtfully found a problem they can solve and that non-specialists can understand. The challenge can be big (e.g. Glydways) or small (e.g. Magic Mind), but it must be one where their solution

is clearly a financial/experiential win for the customer,
is able to have a moat of IP or recurring revenue stream(s) to build long-term value, and
doesn't rely upon altruism (such as "doing the right thing" for the environment) in order to close sales.

Stoicism is a philosophy of life that maximizes positive emotions, reduces negative emotions, and helps individuals hone their virtues of character. Investing like a Stoic means looking for new products and services that will make people happier, doing so with honesty and integrity, and using pattern recognition developed over decades of experience in business to avoid deals that will likely face strong headwinds.

As a Stoic investor, I am keen to find:

problems not already being tackled by multiple competitors,
solutions that can be explained in under a minute (e.g. KinderFarms, Rorra, and TaxGPT),
investments in which the founder has spoken with lots of target customers and can articulate what they have learned from those conversations,
pitch decks that clearly and concisely tell the story (unless I see that the founder is coachable and can quickly learn and improve their deck),
products and services that I would personally use (e.g. Bellway Fiber, Jamby’s, Siphox, Alto IRA, and ReGelTec, and Finesse, for my daughter),
a technology that exponentially improves upon a mundane part of infrastructure or basic components (e.g. Active Surfaces, Fathom Radiant, Femtosense, Sepion, and Falcomm)
companies where my work experience can add value (e.g. Ernest, Roger, Hedral, and Atmos in construction, Sift Healthcare and Gumption in finance, and CYA in insurance),
companies backed by multiple large customers (e.g. Orbit Fab),
tech that improves or replaces unskilled/low-skilled labor (e.g. Armstrong, Bland AI, and Canvas),
valuations below $15M for greater upside, but this isn't set in stone,
pro-environment companies whose products are better/cheaper/faster than their carbon-spewing competitors (e.g. Harbinger, Carbon Crusher, AmorSui, AgTechLogic, and BeeHero)
founders who are more substance than show, and
companies in areas where I live and/or travel.

Of course, the more of these attributes, the more interested I become. As a retired serial entrepreneur, I will be leveraging my position as an angel investor and mentor to generate opportunities for Seneca to invest in early-stage companies, where I can contribute to their strategy, deck review, product development, coaching, board, and/or fundraising. I am looking for founders who lead their companies by actively focusing on what they can control, diminishing their egos, and practicing resilience - fundamental principles of Stoicism. And if the founder needs assistance making their business investable, I will gladly refer them to the Venture Mentoring Team, which does an amazing job helping very early-stage companies. I will also source opportunities from my many successful entrepreneurial friends and limited partners, so don’t hesitate to reach out.

As an aside, I live in downtown San Diego, travel quite a bit, and enjoy meeting new folks, so if you are a start-up founder or a limited partner of Seneca, please drop me a line and we can have an intro Zoom or a cup of coffee if we’re in the same area. Cheers!

Note: I have invested personally in all of the companies named above.

More important note: I am donating 100% of any and all profits from Seneca's carried interests evenly to the ACLU, Friends of Animals, the Freedom from Religion Foundation, Scholarship America, and the Sierra Club.

Risk Advisory: Once you've made your investment, Stoics know that there's no reason to stress over the outcome, since you likely have no control over it. It could go to zero the next day. If you do have introductions or ideas that could benefit the business, please let me know and let's see what we can do. Continual stress and pessimism shorten lives, and aren't they short enough already? Focus on the positive: you were successful enough to have the money to invest, and it might just be wildly profitable. And if not, you'll possibly save on taxes.

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